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Lignin Hydrotreatment to Low-Molecular-Weight Compounds

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Advances in Solar Energy

Part of the book series: Advances in Solar Energy ((AISE,volume 4))

Abstract

Lignin hydrotreating has been studied for a number of reasons. Most of the early work was directed toward the elucidation of lignin’s highly complex polymeric structure. Other workers have been interested in processing lignin into one or two low-molecular-weight products that could be profitably sold. The major reason for this review of the literature is our desire to convert lignin into a mixture of phenols that could be used as an intermediate in the production of a fuel; e.g., a phenol mixture could be converted to methyl aryl ethers and then used as a gasoline octane enhancer. Consequently, this review emphasizes research on the conversion of lignin into phenols or fuel additives.

Because of the distinct differences in the lignin hydrotreating research carried out in Eastern Europe compared to the rest of the world, the eastern work is reviewed separately. Nearly all the Eastern European studies used highly condensed acid hydrolysis lignins with aqueous alkaline solvents and unsupported catalysts. This work has not been extensively reviewed before, and an extra effort was made to translate papers previously unreviewed. The literature from the rest of the world has been reviewed, and so the emphasis here is on more recent citations.

Some complete processes for conversion of lignin to low-molecular-weight compounds have been developed, and these have been reviewed separately.

A substantial amount of work has been published on the hydrotreating of lignin model compounds. This type of research is very useful in developing an understanding of the processes involved in converting lignin to low-molecular-weight compounds and was also given careful attention. Literature coverage goes through 1985.

It is concluded that, whereas it is unprofitable to try to convert lignin to one or two products, the hydrotreating of lignin to a useful mixture should be possible. Continued research is necessary to improve yields and to allow the use of emerging lignins. However, experimental design must be carefully considered and more extensively reported so that research may be compared between different laboratories. Model compound work should be continued to further increase our understanding of the mechanisms involved in obtaining low-molecular-weight products from lignin and also to allow development of new catalysts.

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References

  • Adkins, H. (5 Oct. 1944), “Hydrogenation of Lignin”, U.S. Pat. 2,331,154.

    Google Scholar 

  • Adkins, H. (1937), “Reactions of Hydrogen with Organic Compounds Over Copper Chromium Oxide and Nickel Catalysts,” University of Wisconsin Press, pp. 12–14.

    Google Scholar 

  • Adkins, H., R. L. Frank and E. S. Bloom (1941), “Products of the Hydrogenation of Lignin,” J. Am. Chem. Soc. 63, pp. 549–555.

    Google Scholar 

  • Akhmina, E. I., E. S. Benzmozgin, A. G. Nemchenko, T. A. Podgornaya, S. I. Sukhanovskii and Yu. D. Yudkevich (1965), “Contact Pyrolysis of Lignin Settling Tar to Obtain Demethylated Phenols,” Khim. i Tekhnol. Topliva i Produktov ego Perera botki, Sb. (Moscow-Liningrad: Khimiya) 1965, pp. 12–16 (Russ.).

    Google Scholar 

  • Albright and Tai (1983). In “Pyrolysis: Theory and Industrial Practice.” Albright, Crynes, and Corcoran, eds., NY: Academic Press.

    Google Scholar 

  • Alpert, S. B. and S. C. Schuman (15 Sept. 1970), “Production of Chemicals from Lignin.” CA 851708 A 7038, CA 17512 (680416). Patent assignee: Hydrocarbon Research, Inc.

    Google Scholar 

  • Alpert, S. B. and S. C. Schuman (23 May 1972), “Lignin Sulphonate Conversion— By Treatment with Hydrogen-Rich Gas in a Liquid Hydrocarbon.” CA 900973 A 7223, US 22056(700323). Patent assignee: Hydrocarbon Research, Inc.

    Google Scholar 

  • Arakin, I. E. (1973), “New Methods of Wood Delignification.” Bumazh. Prom. No. 4, pp. 8–9, (Russ.).

    Google Scholar 

  • Arlt, H. G., S. K. Gross and C. Schuerch (1958), “The Lignin Fraction Obtained from the Alkaline Hydrogenation of Maple Wood,” Tappi, pp. 64–70.

    Google Scholar 

  • Babicki, R. and Z. Piotrowski (1973), “Laboratory Thermolysis of Hemicyclia Sepiaria Wood from Ceylon.” Pr. Inst. Technol. Drewna 20, No. 3/4, pp. 3–10, (Pol.; Russ. and Engl. sum.).

    Google Scholar 

  • Bailey, A. J. (1940), “The Industrial Hydrogenation of Lignin.” Pacific Chem. Met. Inds. 4, pp. 13–14, 16.

    Google Scholar 

  • Bailey, A. J. (1943), “Volatile Hydrogenation Derivatives of Lignin,” J. Am. Chem. Soc. 65, pp. 1165–1168.

    Google Scholar 

  • Baker, S. B. and H. Hibbert (1948), “Lignin and Related Compounds.” LXXXVI. “Hydrogenation of Dimers Related to Lignin,” J. Am. Chem. Soc. 70, pp. 63–67.

    Google Scholar 

  • Balandin, A. A., N. A. Vasyunina, S. V. Chepigo and G. S. Barysheva (1959), “Hydrolytic Hydrogenation of Cellulose,” Doklady Akad. Nauk S.S.S.R. 128, pp. 941–994. (Russ.)

    Google Scholar 

  • Belorizky-Perret, N. (1965), “Substituted Derivatives and Hydrogenation of Benzofurans, Lignin Model Compounds,” Ph.D. Thesis, Universite de Grenoble, 61 p. + 15 plates. (Fr.).

    Google Scholar 

  • Benigni, J. D. and I. S. Goldstein (1971), “Hydrogenation of Kraft Lignin,” J. Polymer Sci. (C. Polymer Symp.) 36, pp. 477–488.

    Google Scholar 

  • Bergstrom, H. O. V. and K. N. Cederquist (19 Feb. 1935), “Treating Lignin-Containing Materials Such as Wood, Peat, Bog-Moss and Lignite or Lignin,” Swed. Pat. 82, 615.

    Google Scholar 

  • Beri, R. M. (Feb/March 1977), “Wood as Raw Material for Chemical Industries,” Indian Pulp Paper 31 5, pp. 3–5.

    Google Scholar 

  • Bhaskaran, T. A. and C. Schuerch (Oct. 1969), “Study of Nonvolatile Hy-drogenated Maple Wood Lignin,” Tappi 52 10, pp. 1948–1952.

    Google Scholar 

  • Bhattacharya, A., E. Sondheimer and C. Schuerch (1959), “Lignin from the Alkaline Hydrogenation of Sugar Maplewood.” II. “The Acidic and Water-Soluble Fractions,” Tappi 42, pp. 446–448.

    Google Scholar 

  • Bhattacharys, A. and C. Schuerch (1960), “Lignin from the Alkaline Hydrogenation of Sugar Maplewood.” III. “Chromatographic Separation of Higher-Molecular-Weight Fraction and a Structural Study,” Tappi 43, pp. 840–844, CA 55.10880g.

    Google Scholar 

  • Bisenietse, S. K., A. V. Riikuris and V. N. Sergeeva (1974), “Composition and Properties of Tar Formed During Thermolysis of Lignocellulose.” (2). “Study of the Ether-Soluble Fraction of Tar Formed During Vacuum Thermolysis of Corncob and Birchwood Lignocellulose,” Khim. Drev. (Riga) 15, pp. 130–134, (Russ.).

    Google Scholar 

  • Bisenietse, S. K., M. L. Stendzenietse and A. V. Riikuris (Nov/Dec. 1978), “Composition and Properties of Tar Formed During Thermolysis of Lignocellulose.” (9). “Oligomeric Compounds in Ether-Soluble Fraction of Tars From Birchwood Lignocellulose Pyrolysis,” Khim. Drev. (Riga) 6, pp. 87–90, (Russ.).

    Google Scholar 

  • Bjorkman, A. (1950), “Studies on Hydrogenation of Sulfite Waste Liquor,” Trans. Roy. Inst. Technol., Stockholm 31, 40 pp.

    Google Scholar 

  • Bolker, H. I. and C. M. Li (1973), “Delignihcation of Wood by Hydrogenolysis with a Soluble Catalyst,” Can. Wood Chem. Symp. (Chem. Inst. Can./CPPA, Chateau Frontenac), Extended Abstrs. Papers Presented Vol. 4, pp. 39–41.

    Google Scholar 

  • Bond, G. C. (1974), “Heterogeneous Catalysis, Principles and Applications,” Oxford University Press.

    Google Scholar 

  • Boocock, D. G. B., D. Mackay, M. McPherson, S. Nadeau and R. Thurier (1979), “Direct Hydrogenation of Hybrid Poplar Wood to Liquid and Gaseous Fuels,” Can. J. Chem. Eng. 57, No. 1, pp. 98–101, (Fr. sum.).

    Google Scholar 

  • Borchers, B., F. Fischer and R. Schiene (5 Oct. 1975), “Apparatus and Method for Manufacturing Phenols from Lignin and Ligninized Materials by Continuous Pressure Hydrogenation in a Contact Tube,” Ger. (East) Pat. 115,482. 5 pp.

    Google Scholar 

  • Bowen, A. R. and A. W. Nash (1926), “The Thermal Decomposition of Cellulose and Lignin in Presence of Catalysts and Hydrogen Under Pressure,” Fuel in Science and Practice 5, pp. 138–142.

    Google Scholar 

  • Bower, J. R., L. M. Cooke and H. Hibbert (1943), LXX. “Hydrogenolysis and Hydrogenation of Maple Wood,” J. Am. Chem. Soc. 65, pp. 1192–1195.

    Google Scholar 

  • Bower, J. R., J. L. McCarthy and H. Hibbert (1941), “Lignin and Related Compounds.” LXIII. “Hydrogenation of Wood,” 2. J. Am. Chem. Soc. 63, pp. 3066–3068,

    Google Scholar 

  • Brauns, F. E. and D. A. Brauns (1960), “The Chemistry of Lignin,” NY: Academic Press.

    Google Scholar 

  • Bredenberg, J. B., M. Huuska and P. Toropainen (1984), “Hydrogenolysis and Hydrocracking of the Carbon-Oxygen Bond. 6. Catalytic Hydrogenolysis of Methoxyphenols.” Proceedings of the 9th Iberoamerican Symposium on Catalysis, Lisbon, 1, 8 pp.

    Google Scholar 

  • Bredenberg, J. B., M. Huuski, J. Raty and M. Korpio (1982), “Hydrogenolysis and Hydrocracking of the Carbon-Oxygen Bond. 1. Hydrocracking of Some Simple Aromatic O-Compounds.” J. of Catalysis 77, pp. 242–247.

    Google Scholar 

  • Bredenberg, J. B. and R. Ceylan (March 1983), “Hydrogenolysis and Hydrocracking of the Carbon-Oxygen Bond.” 3. “Thermolysis in Tetralin of Substituted Anisoles,” Fuel 62, pp. 342–344.

    Google Scholar 

  • Brewer, C. P., L. M. Cooke and H. Hibbert (1948), “Lignin and Related Compounds.” LXXXIV. “High-Pressure Hydrogenation of Maple Wood: Hydrol Lignin.” J. Am. Chem. Soc. 70, pp. 57–59.

    Google Scholar 

  • Brezny, R., V. Mihalov and V. Kovacik (1983), “Low-Temperature Thermolysis of Lignins.” (1) “Reactions of beta-O-4 Model Compounds,” Holzforschung 37, No. 4, pp. 199–204, (Engl.; Ger. sum.).

    Google Scholar 

  • Bridger, G. L. (1938), “Phenols from Cornstalk Alkali Lignin. Preparation by Destructive Distillation and Separation by Fractional Distillation,” Ind. Eng. Chem. 30, pp. 1174–1180.

    Google Scholar 

  • Bronovitskii, V. E., I. K. Cheremukhin, M. A. Volochkovich and L. L. Kalinskaya (1967), “Method of Obtaining Low Molecular Products from Hydrolysis Lignin,” USSR pat. 198,906, filed June 1, 1966, Publ. Izobret. No. 14, p. 165, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E., D. R. Ikramova and L. L. Kalinskaya (1973), “Hydrogenolysis of Lignin and Model Compounds in the Presence of Ethanolamine as an Inhibitor,” Khim. Tekhnol. Tsellyulozy Volokna, No. 6, pp. 345–371, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E. and L. L. Kalinskaya (1967a), “Behavior of (Lignin) Model Compounds During Hydrogenolysis,” Uzbek. Khim. Zh. 11, No. 5, pp. 79–81, (Russ.; Uzbek sum.).

    Google Scholar 

  • Bronovitskii, V. E. and L. L. Kalinskaya (1967b), “The Composition of Phenolic Fraction From Hydrogenolysis Products of Cotton and Spruce Lignins,” Uzbek. Khim. Zh. 11, No. 2, pp. 31–34, (Russ.). (National Lending Library transl. in Engl. (8 p.) available from IPC.)

    Google Scholar 

  • Bronovitskii, V. E. and L. L. Kalinskaya (1970), “Oxidation of Lignin in Aqueous Alkali Solution,” Khim. Prirod. Soed. 6, No. 5, pp. 512–517, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E. and L. L. Kalinskaya (1972), “Hydrogenolysis of Willstatter’s Lignin,” Khim. Prirod. Soed. 8, No. 1, pp. 106–112, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E., L. L. Kalinskaya and D. I. Ikramova (1968a), “Composition of the Acid Fractions of Hydrogenolysis Products of Lignin and its Model Compounds,” Uzbek. Khim. Zh. 12, No. 1, pp. 67–69, (Russ.; Uzbek sum.).

    Google Scholar 

  • Bronovitskii, V. E., L. L. Kalinskaya and D. R. Ikramova (1971a), “Hydrogenolysis of Lignin,” Gidroliz. Lesokhim. Prom. 24, No. 8, p. 14, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E., L. L. Kalinskaya and D. R. Ikramova (1971b), “Nature of Neutral Products in Hydrogenolyzates of Acid Lignins and Model Compounds,” Izv. VUZ, Lesnoi Zh. 14, No. 6, pp. 165–168, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E., L. L. Kalinskaya and L. G. Kuznetsova (1966), “Behavior of Lignin Model Compounds During the Process of Hydrogenolysis,” Struktura i Modifik. Khlopk. Tsellyulozy No. 3, pp. 353–364, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E. and A. Nam (1973a), “Action of Alkalies on Lignin,” Deposited Publ, VINITI 5735–73, 9 pp.

    Google Scholar 

  • Bronovitskii, V. E. and A. Nam (1973b), “Action of Alkalies on Lignin. I.,” Khimiya i tekhnol. tsellyulozy i volokna, (Vyp. 6), pp. 372–378.

    Google Scholar 

  • Bronovitskii, V. E. and A. Nam (1973c), “Action of Alkalies on Lignin. II.,” Khimiya i tekhnol. tsellyulozy i volokna, (Vyp 6), pp. 379–386.

    Google Scholar 

  • Bronovitskii, V. E. and A. Sharipdzhanov (1967), “Stabilization of Low-Density Polyethylene with Resins from Lignin Hydrogenolysis,” Uzbek. Khim. Zh. 11, No. 6, pp. 76–78, (Russ.; Uzbek sum.).

    Google Scholar 

  • Bronovitskii, V. E. and A. Sharipdzhanov (1971), “Stabilization of Polyethylene with Hydrogenolysis Products of Lignin,” Plas. Massy, No. 1, pp. 34–36, (Russ.).

    Google Scholar 

  • Bronovitskii, V. E., F. Kh. Salyamova and M. A. Volochkovich (1968b), “Method of Preparation of a Cation Exchanger,” USSR pat. 228,943, filed March 9, 1965, Izobret. No. 32, p. 75.

    Google Scholar 

  • Bronovitskii, V. E., F. Salyamova and M. A. Volochkovich (1967), “Cation Exchange Resins from Products of Lignin Hydrogenolysis,” Uzbek. Khim. Zh. 11, No. 4, pp. 68–70, (Russ.; Uzbek sum.).

    Google Scholar 

  • Bronovitskii, V. E., M. A. Volochkovich, L. L. Kalinskaya and A. Nam (1968c), “Low Molecular Weight Compounds From Lignin,” Uzbek. Khim. Zh. 12, No. 3, pp. 71–74, (Original in Russ.). (National Lending Library transl. in Engl. (9 p.) available from IPC.)

    Google Scholar 

  • Browning, B. L. (1967), Methods of Wood Chemistry, Vols. I and II, NY: Interscience.

    Google Scholar 

  • Bungay, H. R. (1981), Energy: The Biomass Option, NY: Wiley-Interscience.

    Google Scholar 

  • Ceylan, R. and J. B. Bredenberg (1982), “Hydrogenolysis and Hydrocracking of the Carbon-Oxygen Bond.” (2). “Thermal Cleavage of the Carbon-Oxygen Bond in Guaiacol,” Fuel 61, pp. 377–382, (Engl.).

    Google Scholar 

  • Chem Systems, Inc. (1984), “Technical and Economic Assessment of Processes for the Production of Butanol and Acetone-Phase Two: Analysis of Research Advances,” Final Report for Contract No. AI01–81CS66001. DOE/CS/66001–5.

    Google Scholar 

  • Chervenak, M. D. and A. G. Comolli (17 Jan. 1980), “Catalytic Hydrogenation in Fluidized Bed Reactors—With Improved Sepn. of Vapour and Liq. Phases.” Patent Assignee: Hydrocarbon Research, Inc.

    Google Scholar 

  • Chudakov, M. I. (1968), “Industrial Utilization of Lignin,” Khim. Drev. (Riga), No. 1, pp. 311–322 (Russ.).

    Google Scholar 

  • Chum, H. L., S. K. Parker, D. A. Feinberg, J. D. Wright, P. A. Rice, S. A. Sinclair and W. G. Classer (1985a), “The Economic Contribution of Lignins to Ethanol Production from Biomass.” TR-231–2488, Golden, CO: Solar Energy Research Institute.

    Google Scholar 

  • Chum, H. L., L. J. Douglas, D. A. Feinberg and A. A. Schroeder (1985b), “Evaluation of Pretreatments of Biomass for Enzymatic Hydrolysis of Cellulose,” TR-231–2183, Golden, CO: Solar Energy Research Institute.

    Google Scholar 

  • Chum, H. L., D. K. Johnson, M. Ratcliff, S. Black, H. A. Schroeder and K. Wallace (1985c), “Comparison Between Lignins Produced by Steam Explosion and Organosolv Pretreatments,” in Proc. 1985 International Symposium on Wood and Pulping Chemistry, Preprints published by Canadian Pulp and Paper Association, pp. 223–226.

    Google Scholar 

  • Chum, H. L., D. K. Johnson, M. Ratcliff, S. Black, H. A. Schroeder, K. Wallace, D. Robert and K. V. Sarkanen (1985d), “Lignin Characterization Research: A Progress Report,” in Biochemical Conversion Program Semiannual Report, SERI/CP 231–2726, Golden, CO: Solar Energy Research Institute.

    Google Scholar 

  • Clark, E. L. (Feb. 1970), “Novel Hydrorefining Technique Could Give Pulp Yields as High as 90%,” Pulp Paper 44, No. 2, pp. 107–108.

    Google Scholar 

  • Clark, I. T. and J. Green (1968), “Production of Phenols by Cooking Kraft Lignin in Alkaline Solutions,” Tappi 51, No. 1, pp. 44–48.

    Google Scholar 

  • Clark, I. T., J. R. Hicks and E. E. Harris (1951), “Hydrogenation of Douglas Fir Lignin,” Tappi 34, pp. 6–11.

    Google Scholar 

  • Clayton, D. W. and B. I. Fleming (1981), “Reductive Delignification: Past Experience and Current Concepts,” Paperi Puu 63, No. 4a, pp. 275–278, 281–282, 287–288, (Engl.; Finn. sum.).

    Google Scholar 

  • Connors, W. J., L. N. Johanson, K. V. Sarkanen and P. Winslow (1980), “Thermal Degradation of Kraft Lignin in Tetralin,” Holzforschung 34, pp. 29–37.

    Google Scholar 

  • Cooke, L. M., J. L. McCarthy and H. Hibbert (1941a), “Lignin and Related Compounds.” LXI. “Hydrogenation of Ethanolysis Fraction from Maple Wood.” 2, J. Am. Chem. Soc. 63, pp. 3052–3056.

    Google Scholar 

  • Cooke, L. M., J. L. McCarthy and H. Hibbert (1941b), “Lignins and Related Compounds.” LX. Hydrogenation Studies on Maple Ethanolysis Products. 1, J. Am. Chem. Soc. 63, pp. 3056–3061.

    Google Scholar 

  • Coscia, C. J., W. J. Schubert and F. F. Nord (1961a), “Investigation on Lignins and Lignification.” XXIV. “Application of Hydrogenation, Hydrogenolysis, and Vapor Phase Chromatography in the Study of Lignin Structure,” J. Org. Chem. 26, pp. 5085–5091.

    Google Scholar 

  • Coscia, C. J., W. J. Schubert and F. F. Nord (1961b), “Lignins and Lignification.” XXIII. “Hydrogenation and Hydrogenolysis of Native and Milled-Wood Lignins,” Tappi 44, pp. 360–363.

    Google Scholar 

  • Coughlin, R. W., D. W. Sundstrom, H. E. Klei and E. Avni (1984), “Conversion of Lignin to Useful Chemical Products,” Bioconversion Systems (Wise, D. L., ed.) pp. 41–58 CRC Press: Boca Raton, Fl.

    Google Scholar 

  • Coughlin, R. W. and E. Avni (1984), “Chemical Processing of Renewable Materials,” BiotechnoL Bioeng. Symp. No. 14/Simp./Biotechnol. for Fuels and Chemicals (Gatlinburg) 6th: 21–35 (May 15–18, 1984).

    Google Scholar 

  • Coughlin, R. W. and F. Davoudzadeh (1983), “Lignin Depolymerizes Coal at 300° C,” Nature 303, No. 5920, pp. 789–791.

    Google Scholar 

  • Cowley, S. (1985), Heterogeneous Catalysis Course at SERI, Summer 1985.

    Google Scholar 

  • Davoudzadeh, F., B. Smith, E. Avni and R. W. Coughlin (1985), “Depolymerization of Lignin at Low Pressures Using Lewis Acid Catalysis and Under High Pressure Using Hydrogen Donor Solvents,” Holzforschung 39, No. 3, pp. 159–166.

    Google Scholar 

  • Domburgs, G., I. Kirshbaums and V. N. Segeeva (1971), “Pyrolysis of Alkali Lignin in a Gas Flow,” Khim. Drev., No. 7, pp. 43–50 (Russ.).

    Google Scholar 

  • Domburgs, E., I. Kirshbaums and V. N. Sergeeva (1971), “Rapid Pyrolysis of Alkali Lignin in Vacuo,” Khim. Drev., No. 7, pp. 51–54 (Russ.).

    Google Scholar 

  • Domburgs, G., I. Z. Kirshbaums and V. N. Sergeeva (1969), “Rapid Thermal Decomposition of Aspen Alkali Lignin in Air at Normal Pressure,” Khim. Drev., No. 3, pp. 133–137 (Russ.).

    Google Scholar 

  • Domburgs, G. and V. N. Sergeeva (1967), “Effect of the Degree of Sample Dilution with Aluminum Oxide on the Display of Lignin Thermal Effects,” Khim. Drev., No. 3, pp. 377–381 (Russ.).

    Google Scholar 

  • Domburgs, G. E., V. N. Sergeeva and L. Ya. Salna (1967), “Possibility of Studying Lignin Thermolysis by Electron Paramagnetic Resonance,” Izv. Akad. Nauk Latv. SSR, Ser. Khim. No. 4, pp. 509–510, (Russ.) (National Lending Library transl. in Engl. (2 p.).)

    Google Scholar 

  • Domburgs, G., V. N. Sergeeva and G. Zeibe (1971), “Thermographic Study of Model Compounds of Lignin.” I. “Thermal Decomposition of Phenylpropanoic Monomers With a Side Chain of Different Structures,” Khim. Drev., No. 7, pp. 59–65 (Russ.).

    Google Scholar 

  • Donath, E. E., Issued April 24, 1967, “Hydrorefining Process for Vegetable Fibers and Stabilized Products Obtained,” Fr. pat. 1, 483,142, 3 claims, 11 p. (Fr.).

    Google Scholar 

  • Donath, E. E., Issued Sept. 24, 1969, “Hydrogenation Process for Treating a Lignin-Containing Material,” Brit. pat. 1,165,141, 11 claims, 7 p.

    Google Scholar 

  • Dzhon, L. S. and S. Dobrev (1970), “Effect of Some Factors on the Destructive Hydrogenation of Hydrolysis Lignin in the Presence of Limonite Concentrate as Catalyst,” Tseluloza 1, No. 2, pp. 19–23, (Bulg., Russ., Ger., & Engl. sum.).

    Google Scholar 

  • Eachus, S. W. and C. W. Dence (1975), “Hydrogenation of Lignin Model Compounds in the Presence of a Homogeneous Catalyst,” Holzforschung 29, No. 2, pp. 41–48, (Engl.; Ger. sum.).

    Google Scholar 

  • Efendieva, N. F. and N. N. Shorygina (1974), “Hydrogenolysis of the Lignocarbohydrate Complex Isolated from Milled Sprucewood,” Izv. Akad. Nauk SSSR, Ser. Khim. No. 2, pp. 458–461, (Russ.).

    Google Scholar 

  • Emmett, P. H. (1965), “Catalysis Then and Now,” Franklin Publishing Co.

    Google Scholar 

  • Enkvist, T. (1975), “Phenolics and Other Organic Chemicals from Kraft Black Liquors by Disproportionation and Cracking Reactions,” J. Appl. Polymer Sci. (Appl. Polymer Symp.) 28, pp. 285–295.

    Google Scholar 

  • Enkvist, T. and T. Lindfors (1966), “More Organic Chemicals from the Spent Liquors of the Pulping Industry,” Finska Kemistsamfundefs Medd. 75, No. 1, pp. 1–21.

    Google Scholar 

  • Enkvist, T., J. Turunen and T. Ashorn (1962), “The Demethylation and Degradation of Lignin or Spent Liquors by Heating with Alkaline Reagents,” Tappt 45, pp. 128–135.

    Google Scholar 

  • Evans, R. J., T. A. Milne and M. N. Soltys (1986), “Direct Mass-Spectrometric Studies of the Pyrolysis of Carbonaceous Fuels.” III. “Primary Pyrolysis of Lignin.” J. Analyt. and Applied Pyrolysis 9, pp.207–236.

    Google Scholar 

  • Faix, O. and W. Schweers (1975), “Comparative Studies Dealing with Polymeric Models of Lignin (DHP’s) Having Different Compositions.” (6). “Ethanolysis, Nitrobenzene Oxidation, and Hydrogenolysis,” Holzforschung 29, No. 2, pp. 48–55, (Ger.; Engl. sum.).

    Google Scholar 

  • Faix, O. (1973), “Comparative Studies on Synthetic Lignins (DHP) of Various Composition with the Aid of Isotope and Spectroscopic Methods as Well as Through Chemical Decomposition,” Mitt. Bundesforsch. Reinbek/Hamburg 92, 205p., (Ger.).

    Google Scholar 

  • Fengel, D. and G. Wegener (1983), “Wood: Chemistry, Ultra-Structure, Reactions.” de Gruyter: New York.

    Google Scholar 

  • Fierz-David, H. E. and M. Hannig (1925), “The Distillation of Cellulose, Wood and Similar Substances linder Hydrogen Pressure with Catalysts,” Helvetica Chim. Acta 8, pp. 900–923 (Ger.).

    Google Scholar 

  • Fischer, F. (1980), “Lignin. Chemistry (Makes) Contributions to the Use of a Secondary Raw Material,” Zellstoff Papier 29, No. 1, pp. 13–18, (Ger.).

    Google Scholar 

  • Fischer, F. and H. Schrader (1920), “The Dry Distillation of Lignin and Cellulose,” Ges. Abh. Kenntnis Kohle, No. 5, pp. 106–116 (Ger.).

    Google Scholar 

  • Fischer, F. and O. Wienhaus (1980), “Differential Thermal Analysis of Spruce Lignins,” Wiss. Z. Tech. Univ. Dresden 29, No. 3/4, pp. 923–927, (Ger.).

    Google Scholar 

  • Fisher, J. H. and H. B. Marshall (27 Nov. 1951), “Vanillin Production from Waste Sulfite Liquor,” U. S. Patents 2, 576,752–3.

    Google Scholar 

  • Fisher, J. H. and C. A. Sankey (27 Nov. 1951), “Vanillin Production from Waste Sulfite Liquor,” U S. Patent 2, 576,754.

    Google Scholar 

  • Foster, N. C. (1979), “Adhesive Formulation via Thermolytic Modification of Lignin,” Univ. of Washington, Ph.D. Thesis, 191 p. (Avail. from Univ. Microfilms, Ann Arbor, MI 48106).

    Google Scholar 

  • Fruendenberg, K., W. Lautsch and G. Piazolo (1943), “Lignin.” LV. “Hydrogenation of Lignin and Lignin-Containing Substances with Agents Which Yield Hydrogen, Especially Alcohols,” Ber. 76B, pp. 486–498.

    Google Scholar 

  • Freudenberg, K. and W. Lautsch (4 Dec. 1945), “Products from Lignin by Hydrogenation,” U.S. Pat. 2,390,063.

    Google Scholar 

  • Freundenberg, F., W. Lautsch, G. Piazolo and A. Scheffer (1941), “Lignin.” XLII. “The Pressure Hydrogenation of Lignin and the Lignin-Containing Waste Liquors of the Spruce,” Ber. 74B, pp. 171–183.

    Google Scholar 

  • Fukuzumi, T., K. Naito and T. Shibamoto (1976), “Catalytic Hydrogenation of Lignin-Carbonyl Model Compound at Moderate Temperature and Pressure,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 22, No. 8, pp. 457–460, (Jap.; Engl. sum.)..

    Google Scholar 

  • Gaslini, F. (2 Aug. 1960), “Hydrogenation of Lignin and Lignocellulosic Materials with Separation of Cellulose Fibers,” U.S. Pat. 2,947,739.

    Google Scholar 

  • Gates, B. C., J. R. Katzer and G. C. A. Schuitt (1979), “Chemistry of the Catalytic Process,” McGraw-Hill.

    Google Scholar 

  • Gendler, J. L., D. T. A. Huibers and H. J. Parkhurst, Jr. (1983), “Hydroxy-Aromatics from Lignin Hydrogenolysis,” Wood & Agr. Residues (Soltes, E. J., ed.) Proc. ACS Conf. (Kansas City) pp. 391–400 (Sept. 12–17, 1982; publ. 1983 Acad. Press).

    Google Scholar 

  • Giesen, J. (24 Jan. 1955a), “Degradation of Lignin and Lignin-Containing Material,” Ger. Pat. 922,710. Also German Pat 933,988, 6 Oct., 1955. Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (16 March 1955b), “Formation of Phenols by Splitting of Sulfite Spent Liquor Lignin,” Swiss Pat. 305,712. Also German Pat. 936,270, 7 Dec. 1955; US Pat. 2,809,216, 8 Oct., 1957. Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (18 Dec. 1956a), “Degradation of Lignin and Lignin-Containing Material.” US Pat. 2,774,795. Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (18 Jan. 1956b), “Decomposition of Lignin and Lignin-Containing Materials,” Brit. Pat. 743,592. US Pat. 2,290,009, 23 Apr., 1957. Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (28 Feb. 1957a), “Cleavange of Lignin,” Swiss Pat. 318,446. Also German Pat. 1,039,527. Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (15 Mar. 1957b), “Isolation of Lignin from Black Liquor,” Swiss Pat. 318,820, assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (4 July 1961), “Process for Cleavage of Lignin to Produce Phenols,” US Pat. 2,991,314, Assigned to Inventa A. -G. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Giesen, J. (20 Jan 1959), “Making Phenols by Catalytic Hydrogenation of Lignin,” US Pat. 2.870,133, assigned to Inventa Akt.- Ges. fĂĽr Forschung und Patentverwertung.

    Google Scholar 

  • Godard, H. P., J. L. McCarthy and H. Hibbert (1940), “Hydrogenation of Wood,” J. Am. Chem. Soc. 62, p. 988.

    Google Scholar 

  • Godard, H. P., J. L. McCarthy and H. Hibbert (1941), “Lignin and Related Compounds.” LXII. “High-Pressure Hydrogenation of Wood Using Copper Chromite Catalyst.” 1, J. Am. Chem. Soc. 63, pp. 3061–3066.

    Google Scholar 

  • Goheen, D. W. (1966a), “Hydrogenation of Lignin by the Noguchi Process,” Advan. Chem. Ser. 59, pp. 205–225.

    Google Scholar 

  • Goheen, D. W. (1971), “Low Molecular Weight Chemicals (From Lignin),” In Lignins (Wiley-Interscience), pp. 797–831.

    Google Scholar 

  • Goheen, D. W. (24 May 1966b), “Hydrogenation Sulfonated Lignin to Phenolic Substances,” US Pat. 3,253,044, 4 pp. Assigned to Crown Zellerbach Corp.

    Google Scholar 

  • Goheen, D. W. (1981), In Organic Chemicals from Biomass, I. S. Goldstein, Ed., Boca Raton, FL: CRC Press, Inc.

    Google Scholar 

  • Goldstein, I. S. (1975), “Perspectives on Production of Phenols and Phenolic Acids from Lignin and Bark,” J. Appl. Polymer Sci. (Appl. Polymer Symp.) 28, pp. 259–267.

    Google Scholar 

  • Goldstein, I. S., ed. (1981), Organic Chemicals from Biomass, Boca Raton, FL: CRC Press, Inc.

    Google Scholar 

  • Goldstein, I. S. and J. D. Benigni (4 Dec. 1969), “Hydrolysis of Lignin,” Ger. Offen., 1,926,673, 15 pp.

    Google Scholar 

  • Gromovs, V. and M. Pormale (1961), “Hydrotropic and Alkaline Pulping of Deciduous Woods with Simultaneous Hydrogenation of Lignin.” II. “Fractionation of the Products of Hydrogenation of Lignin and Separation of Phenols,” Latvijas PSR Zinatnu Akad. Vestis, pp. 85–92. (Russ.)

    Google Scholar 

  • Gugnin, Yu. A. (1970), “The Accelerating Effect of Polysulfldes and Hydrazine on (Wood) Pulping,” Izv. VUZ, Lesnoi Zh. 13, No. 2, pp. 115–118. (Russ.).

    Google Scholar 

  • Hachihama, Y. and S. Jodai (1950), “Building Stone of Lignin,” Mem. Inst. Sci. Ind. Research Osaka Univ. 7, pp. 165–166.

    Google Scholar 

  • Hachihama, Y. and S. Jodai (1941), “Catalytic Hydrogenation of Lignin,” J. Soc. Chem. Ind. Japan 44, pp. 773–776.

    Google Scholar 

  • Hachihama, Y. and S. Jodai (1942), “Catalytic Hydrogenation of Lignin.” IV. “Catalytic Hydrogenation of Softwood Lignin,” J. Soc. Chem. Ind. Japan 45, pp. 302–303.

    Google Scholar 

  • Hachihama, Y. and S. Jodai (1943), “Studies on Lignin and Related Compounds.” IX. “Carbonyl and Neutral Constituents of the Hydrogenation Products of Softwood Lignin,” J. Soc. Chem. Ind., Japan 46, pp. 507–509.

    Google Scholar 

  • Hachihama, Y. and S. Jodai (1943), “Studies on Lignin and Related Compounds.” VI-VIII. VI. “Comparison of Behaviors of Lignins Isolated from Softwood, Hardwood and Grass in Course of Hydrogenation.” VII. “Phenols in the Hydrogenation Products of Hardwood and Grass Lignins.” VIII. “Phenols in Hydrogenation Products of Lignin,” J. Soc. Chem. Ind., Japan 46, pp. 132–139.

    Google Scholar 

  • Hachihama, Y., S. Jodai and M. Umezu (1940), “Lignin and Related Compounds.” I. “Hydrogenation of Soft Wood Lignin,” J. Soc. Chem. Ind., Japan 43, p. 127.

    Google Scholar 

  • Halmeroski, J. and T. Enkvist (1956), “Some Comparative Pressure Hydrogenations of Sulfate Lignins,” Suomen Kemistilekti 29B, pp. 53–58.

    Google Scholar 

  • Harris, E. E. and H. Adkins (1938), “Reactions of Lignin With Hydrogen,” Paper Trade J.107, pp. 38–40.

    Google Scholar 

  • Harris, E. E., J. DTanni and H. Adkins (1938), “Reaction of Hard Wood Lignin with Hydrogen,” J. Am. Chem. Soc.60, pp. 1467–1470.

    Google Scholar 

  • Harris, E. E., J. Saeman and E. C. Sherrard (1940), “Hydrogenation of Lignin in Aqueous Solutions,” Ind. Eng. Chem 32, pp. 440–441.

    Google Scholar 

  • Harris, E. E., J. F. Saeman and C. B. Bergstrom (1949), “Lignin Hydrogenation Products,” Ind. Eng. Chem.41, pp. 2063–2067.

    Google Scholar 

  • Hastbacka, K. and J. B. Bredenberg (March 1973), “Hydrocracking of Lignin Tar and Lignin Model Compounds,” Paperi Puu 55, No. 3, pp. 129–131, 133–134. (Engl.; Finn. sum.).

    Google Scholar 

  • Heitz, M., B. Massoussa and B. Loubinoux (Sept. 20–22, 1982), “Preparation of Chemical Products from Lignins,” Colloque Sci. Ind. Bois(Grenoble) 3 (Transform. Biol. Chim.), pp. 185–212, (Fr.).

    Google Scholar 

  • Heuser, E. and F. Herrmann (1924), “Fusion of Lignin, Cellulose and Wood with Caustic Potash,” Celluloschemie 5, pp. 1–6.

    Google Scholar 

  • Heuser, E. and C. Skiöldebrand (1919), “Researches on the Lignin of Wood.” I. “Destructive Distillation of Lignin,” Z. angew. Chem.32, No. 1, pp. 41–45;

    Google Scholar 

  • Heuser, E. and C. Skiöldebrand (1919), “Researches on the Lignin of Wood.” I. “Destructive Distillation of Lignin,” J. Soc. Chem. Ind.38, p. 215A.

    Google Scholar 

  • Heuser, E. and A. Winsvold (1921), “Formation of Oxalic Acid from Lignin,” Cellulosechem.2, p. 113.

    Google Scholar 

  • Heuser, E. and A. Winsvold (1923), “Lignin,” Ber.56B, pp. 902–909.

    Google Scholar 

  • Heuser, E. and A. Winsvold (1923), “Lignin,” Cellulosechem.4, pp. 49–58, 62–68.

    Google Scholar 

  • Hoffmann, P. and W. Schweers (1975a), “Hydrogenolysis of Lignin.” (6). “Use of a Semimicro Process in Studies on the Hydrogenolysis System,” Holzforschung 29, No. 1, pp. 18–24, (Ger.; Engl. sum.).

    Google Scholar 

  • Hoffmann, P and W. Schweers (1975b), “Hydrogenolysis of Lignin.” (7). “Comparison of Some Solvents and Catalysts for Hydrogenolysis of Spruce Lignin,” Holzforschung 29, No. 3, pp. 73–79, (Ger.; Engl. sum.).

    Google Scholar 

  • Hoffmann, P. and W. Schweers (1975c), “Hydrogenolysis of Lignin.” (9). “Comparative Hydrogenolysis of Different Lignin Preparations from Some Species,” Paperi Puu 57, No. 11, pp. 771–774, 777–778, 783–785, (Engl.; Finn. sum.).

    Google Scholar 

  • Hoffmann, P. and W. Schweers (1975d), “Hydrogenolysis of Lignin.” (8). “Comparative Hydrogenolyses of Monomeric Model Compounds of Lignin and Lignosulfonate,” Paperi Puu 57, No. 9, pp. 581–584, 589–592, (Engl.; Finn. sum.). 4637.

    Google Scholar 

  • Hoffmann, P. and W. Schweers, Special Issue (1976), “Hydrogenolysis of Lignin.” (10). “Comparative Hydrogenolyses of Lignins, Lignosulfonic Acid, and Lignosulfonate Model Compounds Under Irradiation With gamma-Rays,” Paperi Puu 58, No. 4a, pp. 227–230, 233–234, 237–238, 243–244. (Engl.; Finn. sum.).

    Google Scholar 

  • Hrutfiord, B. F. (1971), “Reduction and Hydrogenolysis (of Lignin),” In Lignin (Wiley-Interscience), pp. 487–509.

    Google Scholar 

  • Huibers, D. T. A. and H. J. Parkhurst (Inventor) (9 Mar 1983), “Phenol Productions From Lignin—by Hydrocracking in Ebullated Catalyst Bed,” GB 2104545 A, 8310 (Basic) DE 3228897 A 830317 8312, FR 2511697 A 830225 8313, SE 8204813 A 830328 8315, JP 58043932 A 830314 8316, NO 8202840 A 830321 8318, FI 8202896 A 830429 8323, ZA 8205692 A 830518 8336, US 4420644 A 831213 8401, CA 1179374 A 841211 8503, GB 2104545 B 850116 8503, Priority Data: US 295459 (810824) Applications: GB 8222421 (820803), Patent Assignee: Hydrocarbon Research. Inc.

    Google Scholar 

  • Huibers, D. T. A. and M. W. Jones (1980), “Fuels and Chemical Feedstock from Lignocellulosic Biomass,” Can. J. Chem.58, No. 6, pp. 718–722, (Engl.; Fr. sum.).

    Google Scholar 

  • Hurff, S. J. and M. T. Klein (1983), “Reaction Pathway Analysis of Thermal and Catalytic Lignin Fragmentation by Use of Model Compounds.” I&EC Fundam.2, No. 4, pp. 426–430, (Engl.).

    Google Scholar 

  • Hwang, B. H. and A. Sakakibara (1981), “Hydrogenolysis of Protolignin.” (18). “Isolation of a New Dimeric Compound with a Hererocycle Involving alpha-beta-Diether,” Holzforschung 35, No. 6, pp. 297–300, (Engl.; Ger. sum.).

    Google Scholar 

  • Hwang, B. H. and A. Sakakibara (1980), “Dimeric Hydrogenolysis Product from Protolignin of Fraxinus Mandshurica Rupr. Var. Japonica Max,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 26, No. 5, pp. 363–364, (Engl.).

    Google Scholar 

  • Hwang, B. H. and A. Sakakibara (1979), “Hydrogenolysis of Protolignin.” (15). “Further Isolation of Some Compounds from Hardwood Lignin,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 25, No. 10, pp. 647–652, (Engl.; Jap. sum.).

    Google Scholar 

  • Hwang, B. H., A. Sakakibara and K. Miki (1981), “Hydrogenolysis of Protolignin.” (17). “Isolation of Three Dimeric Compounds with gamma-O-4, beta-l and beta-0–4 Linkages from Hardwood Lignin,” Holzforschung 35, No. 5, pp. 229–232, (Engl.; Ger. sum.).

    Google Scholar 

  • Hwang, B. H. (1981), “Chemical Structures of Protolignin.” (1). “Isolation of a New Dimeric Compound with beta-Aryl Ether Linkage,” J. Tappik 13, No. 2, pp. 10–18, (Engl.; Korean sum.).

    Google Scholar 

  • Hwang, B. H. (1981), “Study on Hydrogenolysis of Protolignin of Fraxinus Mandshurica,” J. Tappik 13, No. 1, pp. 27–28, (Korean).

    Google Scholar 

  • Hwang, B. H. (1983), “Chemical Structures of New Lignols with Ether Linkage,” Int. Symp. Wood & Pulping Chem. (Japan) 1, pp. 95–100, (Engl.).

    Google Scholar 

  • Hydrocarbon Research, Ind., “Coal Hydrogenation—in Two Stages Using Ebullated Bed Catalyst,” CA 902529 A 000000 7226 (Basic) Priority Data: CA 17208 (680410), Hydrocarbon Research, Inc. Drying of Carbonaceous Solids. US 3519552 A 000000 7027 (Basic) Priority Data: US 707061 (680221).

    Google Scholar 

  • Hydrocarbon Research, Ind., (12 Oct. 1976), “Passivating Particulate Low-Rank Coals—by Drying and Coating with Heavy Hydrocarbon Oil,” US 3985516 A 7643 (Basic) Priority Data: US 606256 (750820), Hydrocarbon Research, Inc. Pharmaceuticals prepd from lignin—by oxygenating and then selectively hydrogenating the lignin (deriv). JP 75002501 B 27 (Jan. 1975), 7508 (Basic) Priority Data: JP 6962249 (690806).

    Google Scholar 

  • Ikramova, D. R., V. E. Bronovitskii and L. L. Kalinskaya (1970), “Hydrogenolysis of Lignin in the Presence of Monoethanolamine,” Uzbek, Khim. Zh.14, No. 5, pp. 97–100, (Russ.; Uzbek sum.).

    Google Scholar 

  • International Hydrogenation Patents Co., Ltd. (16 Nov. 1938), “Utilizing Sulfite Cellulose Waste Liquor,” Fr. Pat. 834, 204, (Fr.).

    Google Scholar 

  • Inventa A. -G. fĂĽr Forschung und Patentverwertung (16 Sept. 1955a), “Degradation of Lignin and Lignin-Containing Material,” Swiss Pat. 308,262.

    Google Scholar 

  • Inventa A. -G. fĂĽr Forschung und Patentverwertung (1 Oct. 1955b), “Degradation of Lignin and Lignin-Containing Material,” Swiss Pat. 308,560.

    Google Scholar 

  • Inventa A. -G. fĂĽr Forschung und Patentverwertung (24 Oct. 1956), “Decomposing Lignin.” Brit. pat. 759,811.

    Google Scholar 

  • Iotech Corporation Ltd. (1982), “Optimization of Steam Explosion Pretreatment,” Final Report for Contract No. DE-AC02–79ET3050.

    Google Scholar 

  • Iotech Corporation Ltd. (1982), “Steam Explosion as a Pretreatment for Biomass Conversion.” Final Report for Contract No. IB-1–9343-1.

    Google Scholar 

  • Jegers, H. E. and M. T. Klein (1985), “Primary and Secondary Lignin Pyrolysis Reaction Pathways,” IE&C Process Design Devt.24, No. 1, pp. 173–183.

    Google Scholar 

  • John, L. S. and S. T. Dobrev (1973), “Infrared Spectroscopy and Gas Chromatographic Study of Phenols and Neutral Substances in the Products of Hydrolysis Lignin Hydrogenation,” Tseluloza Khartiya 4, No. 4, pp. 22–26, (Bulg.).

    Google Scholar 

  • Karaseva, N. M. and E. Z. Karaseva (1975), “Thermolysis of Wood in a Furnace with Repeated Circulation of the Heat Carrier,” Khim. Tverd. Topliva (Moscow), No. 5, pp. 93–97, (Russ.).

    Google Scholar 

  • Karig, F. and E. Stahl (1974), “Influence of Thermolysis Conditions on Functional Groups During Thermofractography of Lignins,” Holzforschung 28, No. 6, pp. 201–203, (Ger.; Engl. sum.).

    Google Scholar 

  • Karpunin, I. I. (1981), “Transformations of Lignin During Alkaline Delignification and Hydrogenation of Wood in Aqueous Media,” Zh. Prikl. Khim.54, No. 10, pp. 2282–2289, (Russ.).

    Google Scholar 

  • Kashima, K. and T. Osada (1961), “The Hydrocracking of Lignin,” Kogyo Kagaku Zasshi 64, pp. 916–919, Noguchi Institute, Tokyo.

    Google Scholar 

  • Kashima, K., T. Osada, H. Tabata, H. Watanabe and T. Kubo (1963), “Studies on the Hydro-Cracking of Lignin by the Continuous Process,” J. Jap. Tappi 17, No. 1, pp. 25–34, (Original in Jap.; Engl. transl. available from NTC).

    Google Scholar 

  • Kashima, K., H. Tabata and H. Watanabe (1961), “Decomposition of Lignin by High Pressure Hydrogen Addition.” II. “Acidic Constituents of Lignin Liquefied,” Kogyo Kagaku Zasshi 64, pp. 919–921.

    Google Scholar 

  • Kashima, H., H. Tabata, H. Watanabe and T. Kubo (1962), “The Hydrocracking of Lignin,” Kami-pa Gikyoshi 16, 901–905.

    Google Scholar 

  • Kato, Y. and K. -i. Sugino (13 June 1939), “Utilization of Lignin.” Japan. Pat. 130,526, (Japan.).

    Google Scholar 

  • Kirshbums, I. Z. and G. Domburga (1970), “Yield and Composition of Monohydric Phenols During Accelerated Pyrolysis of Alkali Lignin,” Latv. PSR Zinat. Akad. Vestis 1970, No. 2, pp. 43–47 (Russ.).

    Google Scholar 

  • Kislitsyn, A. N., Z. M. Rodionova and V. I. Savinykh (1971), “Character of Bond Rupture During Thermolysis of Lignin,” Sb. Tr. Tsentr. Nauch.-Issled. Proekt. Inst. Lesokhim. Prom., 21, pp. 11–18, (Russ.).

    Google Scholar 

  • Klein, M. T. and P. S. Virk (1981), “Modeling of Lignin Thermolysis,” ACS Div. Fuel Chem. Preprints of Papers 26, No. 3, pp. 77–88, (Engl.).

    Google Scholar 

  • Klein, M. T. and P. S. Virk (Feb. 1981), “Model Pathways in Lignin Thermolysis,” Massachusetts Inst. Technol. Energy Lab. Kept. MIT-EL 81–005: 96p.

    Google Scholar 

  • Klein, M. T. and P. S. Virk (1983), “Model Pathways in Lignin Thermolysis.” (1). “Phenethyl Phenyl Ether,” I&EC Fundam.22, No. 2, pp. 35–45, (Engl.).

    Google Scholar 

  • Kleinert, Th. (1952), “Hydrogenation of Lignin with Cyclohexanol,” Monatsh 83, pp. 623–628.

    Google Scholar 

  • Klemola, A. and J. M. Pepper (1969), “2-(2-Methoxy-4-n-Propylphenoxy)Propan-1-oL as a New Spruce Lignin Hydrogenolysis Product.” Chem. Commun., No. 18, p. 1048.

    Google Scholar 

  • Klemola, A. (1970), “Hydrogenation of Lignin,” Soum. Kemistilehti A 43, pp. 265–271, (Finn.).

    Google Scholar 

  • Kosyukova, L. V. (1975), “Gas Chromatographic Analysis of Phenols of Wood Thermolysis Tars,” Khromat. Anal. Khim. Drev., pp. 256–260. (Russ.).

    Google Scholar 

  • Kringstad, K. (1978), “Challenge of Lignin,” Future Sources Org. Raw Matls. (St.- Pierre, L. E., & Brown, G. R., eds.)/Invited Lectures IUPAC World Conf. (Toronto)/Chemrawn I: 627–636 (c1980 Pergamon Press).

    Google Scholar 

  • Kurschner, K. (June, Sept., Dec, 1967), “New Results in Basic Research on Wood,” Holztechnol 8, No. 2, pp. 99–103;

    Google Scholar 

  • Kurschner, K. (June, Sept., Dec, 1967), “New Results in Basic Research on Wood,” Holztechnol 8, No. 3, pp. 153–157;

    Google Scholar 

  • Kurschner, K. (June, Sept., Dec, 1967), “New Results in Basic Research on Wood,” Holztechnol 8, No. 4, pp. 233–236, (Ger.; Russ. & Engl. sum.).

    Google Scholar 

  • Lai, Y. Z. and K. V. Sarkanen (1971), “Isolation and Structural Studies in Lignins. Occurrence, Formation, Structure and Reactions,” (Sarkanen, K. V. and Ludwig, C. H., eds.), New York: Wiley-Interscience.

    Google Scholar 

  • Lautsch, W. and K. Freudenberg (30 Sept. 1943), “Phenol or its Derivatives from Lignin or Ligneous Materials,” Ger. Pat. 741, 686. Deutsche Revisionsund Truhand A. -G. W.

    Google Scholar 

  • Lautsch, W. (1941), “Oxidative and Hydrogenating Degradation of Wood, Lignin and Sulfur-Containing Waste Liquor from Spruce,” Cellulosechem 19, pp. 69–87.

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind.20, No. 3, pp. 25–27;

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind.20, No. 4, pp. 132–133;

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind. 135; No. 5, pp. 35–36;

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind. 135; No. 6, pp. 36–37;

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind. 135; No. 8, p. 68;

    Google Scholar 

  • Leary, R. (March-June, Aug., Sept. 1967), “The Silvichemical File,” Can. Pulp Paper Ind. 135;No. 9, pp. 64–65.

    Google Scholar 

  • Lee, Y. W. and J. M. Pepper (1978), “Lignin and Related Compounds.” (7). “Isolation of a Trimeric Lignin Compound by Hydrogenolysis of Spruce Wood,” Tetrahedron Letters No. 51: 5061–5062.

    Google Scholar 

  • Leger, F. and H. Hibbert (1938), “Lignin and Related Compounds.” XXXIV. “Acetovanilline and Acetosyringone as Degradation Products of Lignin Sulforic Acids.” J. Am. Chem. Soc.60, p. 565.

    Google Scholar 

  • Leopold, B. (1952), “Lignin” III. “Oxidation of Wood from Piceables with Nitrobenzene and Alkali,” Acta Chem. Scand.6, p. 39–72.

    Google Scholar 

  • Levin, E. D., A. V. Rachinskii and S. M. Repyakh (1975), “Hydrocracking with Residueless Processing of Resinous Wastes from the Silvichemical Industry,” Izv. VUS, Lesnoi Zh.18, No. 6, pp. 105–108 (Russ.).

    Google Scholar 

  • Lin, S. Y. and K. P. Kringstad (1970), “Stabilization of Lignin and Lignin Model Compounds to Photodegradation,” Tappi 53, No. 9, pp. 1675–1677.

    Google Scholar 

  • Lin, S. Y. (1983), “Lignin Utilization: Potential and Challenge,” Progress in Biomass Conversion 4, NY: Academic Press, pp. 33–78.

    Google Scholar 

  • Loubinoux, B., M. Heitz, G. Coudert and G. Guillaumet (1980), “Hydrogenolysis of Lignins (with) Nickel Boride Catalyst,” Tetrahedron Letters 21, No. 51, pp. 4991–4994.

    Google Scholar 

  • Loubinoux, B. (15 Jan. 1982), “Lignin Hydrogenolysis and its Use in the Production of 4-Ethyl-2-Methoxyphenol and 2,6-Dimethoxy-4-Ethylphenol,” Fr. Damande FR 2,486,524(CL C07C43/23), 15 pp.

    Google Scholar 

  • Lundquist, K. (1970), “Acid Degradation of Lignin.” II. “Separation and Identification of Low-Molecular-Weight Phenols,” Acta Chem. Scand. 24, No. 3, pp. 889–907 (Engl.).

    Google Scholar 

  • Madan, R. N. and J. S. Upadhyaya (1982), “Plants and Silvichemicals and Their Importance in Human Affairs,” Pulp Paper World 2, No. 5–6, pp. 21–27, (Engl.).

    Google Scholar 

  • Manville, J. F. and J. M. Pepper (July4–6, 1973), “Hydrogenolysis Pulping,” Can. Wood Chem. Symp. (Chem. Inst. Can./CPPA, Chateau Frontenac), Extended Abstrs. Papers Presented 4, pp. 31–37.

    Google Scholar 

  • Matsukura, M. and A. Sakakibara (1973), “Hydrogenolysis of Protolignin.” (8). “Isolation of a Dimer with beta-beta Prime C-C Linkage and a Biphenyl,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 19, No. 4, pp. 171–176, (Engl.; Jap. sum.).

    Google Scholar 

  • Matsukura, M. and A. Sakakibara (1971), “Isolation of New Dimeric and Trimeric Compounds with Carbon-to-Carbon Linkages from Hydrogenolysis Products of Protolignin,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 17, No. 6, pp. 263–264, (Engl.).

    Google Scholar 

  • Matsukura, M. and A. Sakakibara (1971), “Isolation of Further Dimeric Compounds with Carbon-to-Carbon Linkage from Hydrogenolysis Products of Protolignin,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 17, No. 6, pp. 265–266, (Engl.).

    Google Scholar 

  • Matsukura, M. and A. Sakakibara (1973), “Hydrogenolysis of Protolignin.” (5). “Isolation of Some Dimeric Compounds with Carbon-to-Carbon Linkage.” (6). “Isolation of a New Trimeric Compound with Carbon-to-Carbon Linkage,” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 19, No. 3, pp. 131–135, 137–140, (Engl.; Jap. sum.).

    Google Scholar 

  • Matsukura, M. and A. Sakakibara (1969), “Hydrogenolysis of Protolignin.” IV. “Isolation of a Dimeric Material of the “Condensed Type,” J. Japan Wood Res. Soc. 15, No. 7, pp. 297–302, (Engl.: Jap. sum.).

    Google Scholar 

  • Meier, D. and W. Schweers (1981), “Properties and Decomposition of Lignins Isolated by Means of Alcoholic Water Mixtures.” (4). “Production of Monomeric Phenols by Catalytic Hydrogenolysis,” Holzforschung 35, No. 2, pp. 81–85, (Ger.; Engl. sum.).

    Google Scholar 

  • Melms, F. and K. Schwenzon (1967), “Applications of Spent Sulfite Liquor,” (Verwertungsgebiete fĂĽr Sulfit ablauge). Leipzig, Deutscher Verlag fĂĽr Grundstoffindustrie, 541 p. (Ger.).

    Google Scholar 

  • Merewether, J. W. T., L. A. M. Samsuzzaman and R. G. Cooke (1972), “Studies on a Lignin-Carbohydrate Complex.” (3). “Nature of the Complex,” Holzforschung 26, No. 6, pp. 193–197, (Engl.; Ger. sum.).

    Google Scholar 

  • Miller, J. G. and C. Schuerch (1968), “Synthesis of 2,4’-Dihydroxy-3,5’-Dimethoxy- 5-Ethylbibenzyl and its Formation in Lignin Hydrogenation,” Tappi 51, No. 6, pp. 273–277.

    Google Scholar 

  • Miyazaki, M., K. Oda, T. Ishihara, J. Tanaka, N. Furuya, A. Yamaguchi, S. Takahashi, T. Hiroi, K. Shimizu and A. Sakakibara (1966), “Studies on Hydrogenation of Lignin in Continuous Equipment,” Bull. Govt. Forest Expt. Sta. (Tokyo) 195, pp. 57–159, (Jap.; Engl. sum.).

    Google Scholar 

  • Moldavskii, B. L. and K. Vainshtein (1935), “Hydrogenation of a Lignin,” Khim. Tverdogo Topliva 6, pp. 656–662.

    Google Scholar 

  • Monsanto Chemical Co. (5 Aug. 1953), “Vanillin from Lignin,” Brit. Pat. 695,301.

    Google Scholar 

  • Moore, R. G. D. and H. Hibbert (1936), “Lignin and Related Compounds.” XXVIII. “The Behavior of Lignin Toward Activated Hydrogen,” Can. J. Research 14, pp. 404–407.

    Google Scholar 

  • Morgen, L. M. (1966), “Phenols as Thermolysis Products of Cotton Hull Lignin,” Struktura i Modifik. Khlopk. Tsellyulozy, No. 3, pp. 365–373, (Russ.).

    Google Scholar 

  • Morikawa, K., T. Kimoto and A. Ryonosuke (1941), “Direct Determination of Oxygen in Organic Compounds by Hydrogenation.” III. “Reduction Mechanism on the Nickel-Thoria Catalyst,” Bull. Chem. Soc. Japan 16, pp. 229–232.

    Google Scholar 

  • Morita, M. and S. Sato (Feb. 15, 1980), “Liquefaction of Coal and Lignin,” Jap. pat. Kokai 21,478/80. 6 p. C1.C10G1/06. Filed: Jap. appln. 84,440/79 (July 4, 1977).

    Google Scholar 

  • Morohoshi, N. and A. Sakakibara (1971a), “Distribution of Condensed Type (Structures) in Lignin: Comparison of Lignin Fractions in Hydrogenolysis Products of MWL, LCC (Lignin-Carbohydrate Complex), and Wood Residue.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 17, No. 8, pp. 354–361. (Original in Jap.; Engl. Transi, available from IPC).

    Google Scholar 

  • Morohoshi, N. and A. Sakaibara (1971b), “Studies on Hydrogenolysis of Milled Wood Lignin: Properties of Fractions Separated by Gel Filtration.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 17, No. 8, pp. 347–353. (Jap.; Engl. sum.).

    Google Scholar 

  • Murashkevich, T. V., A. P. Runtso and A. I. Skrigan (1970), “Synthesis of Resins from Total Phenols Isolated During Pyrolysis of Wood Hydrolysis Lignin,” Issled. Prir. Sn. Polim Mater. Ikh Ispol’z, pp. 176–179 (Russ.).

    Google Scholar 

  • Murashrevich, T. V., A. I. Skrigan and A. I. Khat’ko (1970), “Pyrolytic Decomposition of Hydrolysis Lignin,” Vestsi Akad. Navuk Belarus. SSR, Ser. Khim. Navuk, No. 1, pp. 80–84 (Russ.).

    Google Scholar 

  • Naham, L. S. (1965), “Delignification of Wood by Hydrogenation in the Presence of Dicobalt Octacarbonyl,” Ind. Eng. Chem., Prod. Res. Develop. No. 4, pp. 71–74.

    Google Scholar 

  • Nahum, L. S. (April 1969), “Estimation of Double Bond Content in Lignin from Results of the Oxo Reaction of Wood and Lignin Model Compounds.” Tappi 52, No. 4, pp. 712–714.

    Google Scholar 

  • Nakatsubo, F. and T. Higuchi (1975), “Synthesis of l,2-Diarylpropane-l,3-Diols and Determination of Their Configurations.” Holzforschung 29, No. 6, pp. 193–198, (Engl.; Ger. sum.).

    Google Scholar 

  • Nakatsubo, F., K. Sato and T. Higuchi (1975), “Synthesis of Guaiacylglycerol-Beta-Guaiacyl Ether.” Holzforschung 29, No. 5, pp. 165–168. (Engl.; Ger. sum.).

    Google Scholar 

  • Nimz, H., K. Das and N. Minemur (1971), “Low-Molecular-Weight Degradation Products of Lignin.” I.” Degradation of Beechwood Lignin with Thioacetic Acid,” Chem. Ber. 104, No. 6, pp. 1871–1876 (Ger.).

    Google Scholar 

  • Nippon Kaihatsu Consultant K. K. (Apr. 10, 1981a), “Catalytic Cracking of Heavy Oil and the Catalyst.” Jpn. Patent Kokai Tokkyo Koho 81 37,046. 4 pp.

    Google Scholar 

  • Nippon Kaihatsu Kogyo K. K. (Jan. 12, 1981b), “Catalytic Cracking of Heavy Petroleum Oils.” Jap. pat. Kokai 2,389/81. 5 p. C1.C1OG11/02. Filed: Jap. appln. 77,546/79 (June 21, 1979).

    Google Scholar 

  • Noguchi Research Foundation, (Sept. 4, 1963), “Liquefaction of Lignin.” Japan. Pat. 17,018 (′63). 2 pp. M. Oshima, Y. Maeda, and H. Kajima, inventors.

    Google Scholar 

  • O’Neil, D. J. (1978), “Integrated Chemical System for Whole-Tree Utilization of Paraquat-Treated Pines.” Lightwood Res. Coord. Council Proc. Ann. Mtg. (Atlantic Beach, FL): 54–65 (Jan. 10–11, 1978). (Avail,. from SE Forest Expt. Sta., Box 2570, Asheville, NC 28802).

    Google Scholar 

  • Oelert, H. H. and H. El Saied (1977), “Conversion of Agricultural Waste Products to Oil.” Erdol Kohle Erdgas Petrochemie 30, No. 3, pp. 138, (Ger.).

    Google Scholar 

  • Ohta, M. and A. Sakakibara (Oct. 1969), “Hydrogenolysis of Protolignin.” III.” Isolation of Diguaiacylpropanol, and Chromatographic Detection of Some Monomers.” J. Japan Wood Res. Soc. 15, No. 6, pp. 247–250, (Engl.; Jap. sum.).

    Google Scholar 

  • Oiwa, S., H. Kashima, M. Fukushima and M. Morita (Sept. 8, 1959), “Liquefation of Lignin.” Japan. Pat. 7920 (′59). Assigned to Noguchi Research Institute, Inc.

    Google Scholar 

  • Okay, A. (1962), “Lignin and Lignification.” XXV. “Hydrogenation of Milled-Wood Lignins from White Pine and Blue Spruce.” J. Org. Chem. 27, pp. 1783–1786.

    Google Scholar 

  • Okay, A. (1963), “Investigations of Lignins and Lignification.” XXIX. “Hydrogenation Products of Spruce Milled-Wood Lignin and of Related Model Compounds.” Holzforschung 17, pp. 105–110. (Eng.)

    Google Scholar 

  • Oshima, M., K. Kashima, T. Kubo, H. Tabata and H. Watanabe (1966), “Studies of the Hydrocracking of Lignin.” (1) “The Hydrocracking of Desulfonated Sulfite Waste Lignin.” (2) “Components of Lignin Hydrocracking Products.” (3) “Hydrocracking of Various Types of Lignin.” (4) “Evaluation of Catalysts.” Bull Chem. Soc. Japan 39, No. 12, pp. 2750–2767 (1966). (Engl.).

    Google Scholar 

  • Oshima, M., Y. Maeda and K. Kashima (14 Dec. 1965), “Liquefying Lignin,” U.S. Pat. 3,233,698, 9 pp. (Noguchi Institute).

    Google Scholar 

  • Oshima, M., Y. Maeda and H. Kajima (4 Sept. 1963), “Liquefaction of Lignin,” Japan. Pat. 17,018(′63), 2 pp. (Noguchi Institute).

    Google Scholar 

  • Oshima, M., Y. Maeda and H. Kajima (1 Aug. 1963), “Liquefaction of Lignin,” Japan. Pat. 13,864(′63), 3 pp. (Noguchi Institute).

    Google Scholar 

  • Oshimo, M., Y. Maeda and K. Kashima (26 Oct. 1961), “Liquefaction of Lignin Compounds.” Ger. Pat. 1,115,737. 6 pp. (Noguchi Institute).

    Google Scholar 

  • Osuskii, A. and J. Yu. Kubin (1965), “Hydrolysis Lignin, Its Activation With Alkali Under Pressure and its Uses.” Perspekt. Grundlagenforsch. Holzes, Bratislava, 1963, pp. 221–224. (Russ.; Slovak. & Ger. sum.).

    Google Scholar 

  • Panasyuk, V. G. (1957), “Thermal Treatment of Hydrolytic Lignin.” IV. “Mechanism of Vacuum-Thermal Process of Liquid-Phase Decomposition of Lignin and the Effect of Physical Factors,” J. Appl. Chem. USSR 30, pp. 1258–1265 (English translation).

    Google Scholar 

  • Panasyuk, V. G. (1957), “Thermal Treatment of Hydrolytic Lignin.” III. “Phenols From the Decomposition of Hydrolytic Lignin,” J. Appl. Chem. USSR 30, pp. 1114–1120 (English translation).

    Google Scholar 

  • Panasyuk, V. G. (1957), “Thermal Treatment of Hydrolytic Lignin.” I. “Vacuum-Thermal Decomposition of Wood Hydrolytic Lignin in a Liquid Phase,” Zhur. Priklad. Khim. 30, pp. 598–603, (Russ.).

    Google Scholar 

  • Panasyuk, V. G. (1958a), “Thermal Treatment of Hydroytic Lignin.” VI. “Comparison of Different Methods of Thermal Decomposition of Hydrolytic Lignin,” Zhur. Priklad. Khim. 31, pp. 1605–1607, (Russ.).

    Google Scholar 

  • Panasyuk, V. G. (1958b), “Thermal Solution of Cotton-Seed-Hull Lignin,” Zhur. Priklad. Khim. 31, pp. 1409–1414, (Russ.).

    Google Scholar 

  • Panasyuk, V. G. and N. S. Maksimenko (1958), “Thermal Decomposition of Hydrolytic Lignin from Cotton-Seed Hulls,” Gidrolz i Lesokhim Prom. 11, No. 1, pp. 16–17, (Russ.).

    Google Scholar 

  • Panasyuk, V. G., L. V. Panasyuk, N. S. Marksimenko and F. S. Lapshin (1959), “Thermal Decomposition of Hydrolytic Lignin Under Vacuum,” Gidrolis i Lesokhim. Prom. 12, No. 7, pp. 16–17, (Russ.).

    Google Scholar 

  • Parker, P. E. (1967), “Alkaline Hydrogenation of Lignin in Maplewood.” Ph.D. Thesis State Univ. College of Forestry at Syracuse Univ., 131 p., Diss. Abstr. 27, 9, pp. 3044B (March, 1967).

    Google Scholar 

  • Parkhurst, H. J., D. T. A. Huibers, Jr. and M. W. Jones (1980), “Production of Phenol From Lignin.” ACS Div. Petroleum Chem. Preprints 25, No. 3, pp. 657–667.

    Google Scholar 

  • Pearl, I. A. (1942), “Vanillin From Lignin Materials,” J. Am. Chem. Soc. 64, p. 1429.

    Google Scholar 

  • Pearl, I. A. (1944), “Reduction of Aromatic Nitro Compounds with Sulfite Waste Liquor,” J. Org. Chem. 9, p. 429.

    Google Scholar 

  • Pearl, I. A. (1950), “Lignin and Related Products III. The Oxidation of Sulfite Spent Liquor with Cupric Oxide Under Pressure,” J. Am. Chem. Soc. 72, p. 2309.

    Google Scholar 

  • Pearl, I. A. (4 Oct. 1949), “Vanillin Acid from Lignin,” U.S. Pat. 2,483,559.

    Google Scholar 

  • Pearl, I. A., (March 1974), “Annual Review of Lignin Chemistry. IPC” (Appleton, Wis.), 90 p.

    Google Scholar 

  • Pepper, J. M., C. J. Brounstein and D. A. Shearer (1951), “Studies on Lignin by Means of Catalytic Hydrogenation of Aspenwood and Wheat Straw.” J. Am. Chem. Soc. 73, pp. 3316–3319.

    Google Scholar 

  • Pepper, J. M. and R. W. Fleming (1978), “Lignin and Related Compounds.” (5). “Hydrogenolysis of Aspen Wood Lignin Using Rhodium-on-Charcoal as Catalyst.” Can. J. Chem. 56, No. 7, pp. 896–898, (Fr. sum.).

    Google Scholar 

  • Pepper, J. M. and Y. W. Lee (1969), “Lignin and Related Compounds.” (1). “Comparative Study of Catalysts for Lignin Hydrogenolysis.” Can. J. Chem. 47, No. 5, pp. 723–727.

    Google Scholar 

  • Pepper, J. M. and Y. W. Lee (1970), “Lignin and Related Compounds.” II. “Studies Using Ruthenium and Raney Nickel as Catalysts for Lignin Hydrogenolysis.” Can. J. Chem. 48, No. 3, pp. 477–479.

    Google Scholar 

  • Pepper, J. M. and W. Steck (1963), “The Effect of Time and Temperature on the Hydrogenation of Aspen Lignin.” Can. J. Chem. 41, pp. 2857–2875.

    Google Scholar 

  • Pepper, J. M., W. F. Steck, R. Swaboda and J. C. Karapally (1966), “Hydrogenation of Lignin by Using Nickel and Palladium Catalysts.” Advan. Chem. Ser. 59, pp. 238–248.

    Google Scholar 

  • Pepper, J. M. and P. Supathna (1978), “Lignin and Related Compounds.” (6). “Study of Variables Affecting the Hydrogenolysis of Spruce Wood Lignin Using a Rhodium-on-Charcoal Catalyst.” Can. J. Chem. 56, No. 7, pp. 899–902.

    Google Scholar 

  • Petrocelli, F. P. and M. T. Klein (1985), “Chemical Modeling Analysis of the Yields of Single-Ring Phenolics from Lignin Liquefaction.” Ind. Eng. Chern. Prod. Res. Dev. 24, pp. 635–641.

    Google Scholar 

  • Phillips, M. (1929), “Chemistry of Lignin.” II. “Destructive Distillation of Lignin From Corn Cobs,” J. Am. Chem. Soc. 51, pp. 2420–2426.

    Google Scholar 

  • Phillips, M. (1933), “Dry Distillation of Residue of Waste Sulfite Liquor,” Ind. Eng. Chem. 25, pp. 991–993.

    Google Scholar 

  • Phillips, M. (1931), “Chemistry of Lignin.” V. “Distillation of Alkali Lignin with Zinc Dust in an Atmosphere of Hydrogen.” J. Am. Chem. Soc. 53, pp. 768–774.

    Google Scholar 

  • Phillips, M. and M. J. Goss (1932), “Chemistry of Lignin.” VII. “Distillation of Alkali Lignin in Reduced Atmosphere of Carbon Dioxide,” Ind. Eng. Chem. 24, pp. 1436–1441.

    Google Scholar 

  • Phillips, M. and M. J. Goss (1932), “Lignin.” VI. “Distillation of Alkali Lignin with Zinc Dust in an Atmosphere of Hydrogen.” J. Am. Chem. Soc. 54, pp. 1518–1521.

    Google Scholar 

  • Pines, H. (1981), “The Chemistry of Catalytic Hydrocarbon Conversions,” McGraw-Hill.

    Google Scholar 

  • Ploetz, T., H. Richtzenhain, W. Deiters and J. Giesen (Jan. 1963), “Low-Boiling Cleavage Product Preparation from Lignin.” German Pat. 1,142,853, 316 pp. Assigned to Reldmuehie A. -G.

    Google Scholar 

  • Pressure Chemical Co. (1968), “New “Selective” Hydrogenation Pulping Process.” Pulp Paper Mag. Can 69, No. 15, p. 30.

    Google Scholar 

  • Prosinski, S., Z. Czechowski and M. Kielczewski (1970), “Thermolysis of Oakwood Lignin and Some Properties of the Products Obtained.” Koks. Smola. Gaz 15, No. 11, pp. 322–323, (Pol.; Russ., Engl., Fr. & Ger. sum.).

    Google Scholar 

  • Rachinskii, A. V., N. M. Dorzet, L. M. Levina, N. A. Chuprova, Z. P. Belikova, S. M. Repyakh, G. V. Nikolaeva, G. V. Tikhomirova and E. D. Levin (1975), “Chromatographic Analysis of Condensing Products of Wood Pyrolysis.” Khromat. Anal. Khim. Drev., pp. 249–255. (Russ.).

    Google Scholar 

  • Rachinskii, A. V. and E. D. Levin (1974), “Composition of Hydrocracking Products of the Oil from Lignin Pyrolysis Tar.” Izv. VUZ, Lesnoi Zh. 17, No. 1, pp. 111–113, (Russ.).

    Google Scholar 

  • Rachinskii, A. V. and E. D. Levin (1975), “Effect of Technological Factors on Product Yield from the Hydrocracking of the Total Oil Obtained from Lignin Pyrolysis Tar.” Izv. VUZ, Khim. i Khim. Tekhnol. 18, No. 4, pp. 645–648, (Russ.).

    Google Scholar 

  • Reale, M. J., D. D. Clarke, W. J. Schubert and F. F. Nord (1966), “Lignins and Lignification.” XXXI. “Characterization of Metasequoia Milled Lignin. Holzforschung 20, pp. 31–36, (Engl.).

    Google Scholar 

  • Richterova, V. (May 15, 1982), “Semichemical Pulp and Lignin.” Czecholsl. pat. 195,751. Issued May 15, 1982. 3 pp. C1.D213C3/00. Filed: Czechosl. appln. 2,646/67 (April 11, 1967).

    Google Scholar 

  • Rieche, A., L. Redinger and K. Lindenhayn (1964), “Hydrogenolysis of Lignin and Analysis of Phenolic Products.” Monatsber. Dent. Akad. Wiss. Berlin 6, pp. 430–439. (Ger.).

    Google Scholar 

  • Rieche, A., L. Redinger and K. Lindenhayn (1966), “Hydrogenation of Lignin.” Brennst. Chem 47, pp. 326–330, (Ger.).

    Google Scholar 

  • Riikuris, A. V. and S. K. Bisenietse (1974), “Composition and Properties of Tar Formed During Thermolysis of Lignocellulose.” (3). “Potentiometric Titration in a Non-Aqueous Medium of Lignin and of Products of Thermal Degradation of Corncob and Birchwood Lignocellulose.” Khim. Drev. (Riga) 15, pp. 135–143, (Russ.).

    Google Scholar 

  • Riikuris, A. V. and S. K. Bisenietse (1976), “Composition and Properties of Tar Formed During Thermolysis of Lignocellulose.” (7). “Determination of Acid Groups in Compounds Isolated from Tar Formed During the Thermolysis of Birchwood and in Model Aromatic Hydroxy Acids.” Khim. Drev. (Riga) No. 1, pp. 78–83, (Russ.).

    Google Scholar 

  • Rudnick, L. R. (Oct. 11, 1983), “Coal Liquefaction and Resid. Processing with Lignin.” U.S. Pat. 4,409,089. 5 pp. Assigned to Mobil Oil Corp.

    Google Scholar 

  • Rydholm, S. A. (1965), “Pulping Processes,” NY: Wiley.

    Google Scholar 

  • Sakakibara, A. (1983), “Chemical Structure of Lignin Related Mainly to Degradation Products.” Recent Adv. Lignin Biodegradation Res. (T. Higuchi, H. -M. Chang & T. K. Kirk, eds.) pp. 12–33 (c1983. Uni Publ. Co., Tokyo). (Engl.).

    Google Scholar 

  • Sakakibara, A. (1976), “Degradation Products of Protolignin and the Structure of Lignin.” Recent Adv. Phytochem., 11 (Proc. 16th Ann. Mtg. Phytochem. Soc. N. Am., Aug. 1976 Vancouver) pp. 117–139 (Plenum Press, 1977).

    Google Scholar 

  • Sakakibara, A. (1981), “Hydrogenolysis of Lignin.” IUFRO 17th World Congress (Kyoto), Sept. 6–12, 5, pp. 367–375.

    Google Scholar 

  • Sakakibara, A. (Dec. 23, 1963), “Phenols From Lignin or Lignin-Containing Material.” Japan. Pat. 26,668. 23 Dec, 1963. 3 pp. Issued to the Forestry Institute.

    Google Scholar 

  • Sakakibara, A. (1980), “Structural Model of Softwood Lignin.” Wood Sci. Technol. (NY) 14, No. 2, pp. 89–100.

    Google Scholar 

  • Sakakibara, A., Y. Edashige, T. Uematsu and H. Takeyama (1983), “Hydrogenolysis Pulping.” Japan Tappi 37, No. 4, pp. 343–348, (Jap.; Engl. sum.).

    Google Scholar 

  • Sakakibara A., M. Ohta, I. Wada and M. Matsukura (1969), “Hydrogenolysis of Protolignin.” J. Japan Wood Res. Soc. 15, No. 2, p. 84, (Engl.).

    Google Scholar 

  • Sakakibara, A., K. Sudo, M. Kishi, M. Aoyama, and B. H. Hwang (1980), “Hydrogenolysis of Protolignin.” (16). “Isolation of beta-0–4 and beta-beta Type Compounds.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 26, No. 9, pp. 628–632, (Engl.; Jap. sum.).

    Google Scholar 

  • Sakakibara, A. and A. Tadasi (1961), “Pressure Hydrogenolysis of Lignin.” III. “Selection of Catalysts for Obtaining Phenols.” Nippon Mokuzai Gakkaishi 7, pp. 19–23.

    Google Scholar 

  • Sakakibara, A., J. Tanaka and N. Furuya (1966), “Studies on Hydrogenolysis of Lignin.” (6). “Factors Affecting Hydrogenolysis of Lignosulfonic Acids with Iron Pentacarbonyl Catalyst.” J. Japan Wood Res. Soc. 12, No. 5, pp. 245–250, (Jap.; Engl. sum.).

    Google Scholar 

  • Salyamova, F. and V. E. Bronovitskii (1970), “Cation-Exchange Resins from Lignin.” Uzbek Khim. Zh. 14, No. 3, pp. 72–73, (Russ.; Uzbek sum.).

    Google Scholar 

  • Sangalova, N. A., M. I. Kravchenko and I. P. Uvarov (1968), “Sedimenation Tars from Thermolysis of Hydrolysis Lignin.” Sb. Tr. TNII Lesokhim. Prom. 19, pp. 46–51, (Russ.).

    Google Scholar 

  • Sano, Y. and A. Sakakibara (1980), “Hydrogenolysis of Lignin with Mixture of Alcohol, Sodium Hydroxide and Water.” Res. Bull. Coll. Expt. Forest Hokkaido Univ. 37, No. 1, pp. 241–259, (Jap.; Engl. sum.).

    Google Scholar 

  • Sarkanen, K. V. and C. H. Ludwig, eds. (1971), “Lignins: Occurrence, Formation, Structure and Reactions.” Wiley-Interscience (N.Y., London, Sydney, Toronto), cl971, 916 p.

    Google Scholar 

  • Sarkanen, K. V. (1980), “Acid-Catalyzed Delignihcation of Lignocellulosics in Organic Solvents,” Progress in Biomass Conversion 2, pp. 127–144.

    Google Scholar 

  • Sarkanen, K. V. (1979), “Lignin and Phenolic Polymers.” IUPAC Intern. Cong. (27th) Pure Appl. Chem., pp. 299–306 (Aug. 27–31, 1979; cl980).

    Google Scholar 

  • Satterfield, R. N. (1981), “Heterogeneous Catalysis, In Practice,” McGraw-Hill.

    Google Scholar 

  • Saur, M., V. Medonos and V. Ruzicka (1983), “Pyrolysis of a Sodium Salt of Kraft Lignin in Hydrogen Atmosphere.” Chem. Prumysl 33, No. 12, pp. 652–655, (Czech).

    Google Scholar 

  • Schulz, L. (16 Jan. 1940), “Vanillin,” U.S. Pat. 2,187,366.

    Google Scholar 

  • Schultz, T. P. (1981), “Systematic Study of Reductive Degradation of HCL Lignin Into Useful Chemicals.” North Carolina State Univ. (Raleigh), Ph.D. Thesis: 135 p. (Avail. from Univ. Microfilms, Ann Arbor, MI 48106; no. 8128503.).

    Google Scholar 

  • Schultz, T. P., C. L. Chen, I. S. Goldstein and F. P. Scaringelli (1981), “Analysis of Lignin Hydrogenation Products by Gas Chromatography.” J. Chromat. Sci. 19, No. 5, pp. 235–237.

    Google Scholar 

  • Schultz, T. P., C. -L. Chen and I. S. Goldstein (1982), “Attempted Depolymerization of HCL Lignin by Catalytic Hydrogenolysis.” J. Wood Chem. Technol. 2, No. 1, pp. 33–46.

    Google Scholar 

  • Schultz, T. P., R. J. Preto, J. L. Pittman and I. S. Goldstein (1982), “Hydrotreating of Hydrochloric Acid Lignin in a Hydrogen-Donor Solvent.” J. Wood Chem. Technol. 2, No. 1, pp. 17–31.

    Google Scholar 

  • Schuman, S. C. and S. Field (Sept. 15, 1970), “Hydrogenation of Sulfite Waste Liquor.” Can. pat. 851,709. Issued Sept. 15, 1970. 30 claims, Assignee: Hydrocarbon Research, Inc.

    Google Scholar 

  • Schweers, W. (1966), “Hydrogenolysis of Lignin.” Paperi Puu 48, No. 4a, pp. 161–174, (Original in Ger.; Engl. transl. available from NTC).

    Google Scholar 

  • Schweers, W. (1969a), “Hydrogenolysis of Lignin.” (3). “Comparative Hydrogenations of 4-Alkylphenols and of 4-Alkylguaiacols.” Holzforschung 23, No. 4, pp. 120–127, (Ger.; Engl. sum.).

    Google Scholar 

  • Schweers, W. (1969b), “Hydrogenolysis of Lignin.” (2). “Hydrogenation of Various Lignins with Complex Compounds of the Transition Metals iron, Cobalt, and Nickel Used as Catalysts.” Holzforschung 23, No. 1, pp. 5–9, (Ger.; Engl. sum.).

    Google Scholar 

  • Schweers, W. (1975), “Research Problems in Wood Chemistry in Connection with Problems of Raw Material and Energy.” Papier 29, No. 1, pp. 1–8, (Ger.; Engl. & Fr. sum.).

    Google Scholar 

  • Schweers, W. and O. Beinhoff (1974), “Hydrogenation of Lignin.” (5). “Comparative Hydrogenation of 4-Alkylsyringols.” Holzforschung 28, No. 1, pp. 20–24, (Ger.; Engl. sum.).

    Google Scholar 

  • Schweers, W., W. Lange and O. Beinhoff (1972), “Hydrogenolysis of Lignin.” (6). “Synthesis and Characterization of 3,5-Dimethoxyalkylcyclohexanes.” Holzforschung 26, No. 5, pp. 161–164, (Ger.; Engl. sum.).

    Google Scholar 

  • Schweers, W. and M. Rechy (1973), “Report on the (Lectures and) Round-Table Discussion on the “Chemistry of Wood Digestion” Held on June 25, 1973 in Baden-Baden.” (3). “Pulping Wood with Phenols (III). Pulping Pine-and Beech Wood,” Papier 27, No. 12, pp. 636–639 (Ger.).

    Google Scholar 

  • Seidel, E. M. (1967), “New Developments in Silvichemicals.” Econ. Botany 21, No. 1, pp. 31–41.

    Google Scholar 

  • Sergeeva, V. N. and J. Surna (1960), “Thermal Decomposition of Sulfuric Acid Lignin in a Stream of Hydrogen.” Trudy Inst. Lesokhoz. Problem i Khim. Drevesiny, Akad. Nuak Latv. S.S.R. 21, pp. 107–117. (Russ.)

    Google Scholar 

  • Sharipdzhanov, A. and V. E. Bronovitskii (1970), “Stabilization of Polypropylene with the Products of Lignin Hydrogenolysis.” Uzbek. Khim. Zh. 14, No. 4, pp. 60–61, (Russ.; Uzbek sum.).

    Google Scholar 

  • Sharipdzhanov, A., V. E. Bronovitskii and Kh. U. Usmanov (Jan. 1971), “Stabilizer for Low-Pressure Polyethylene.” USSR Pat. 292,943. From Otkry-tiya, Izobret., Prom. Obraztsy, Tovarnye Znaki 1971, 48(5), 92.

    Google Scholar 

  • Sharipdzhanov, A. and Kh. U. Usmanov (Oct. 24, 1977), “Solution for Forming Films.” USSR Pat. 732,307. Issued May 5, 1980. Filed: USSR appln. 2,535,949/23–05.

    Google Scholar 

  • Sherrard, E. C. and E. E. Harris (Feb. 7, 1939), “Catalytic Hydrogenation of Lignin,”. U.S. Pat. 2,146,655.

    Google Scholar 

  • Sherrard, E.C. and E. E. Harris (Oct. 25, 1940a), “Treating Lignin.” Brit. Pat. 528,268. 25.

    Google Scholar 

  • Sheppard, E.C., E. E. Harris, J. P. Saeman (Jan. 12, 1942), “Hydrogenation and (or) Hydrolysis of Lignin.” Brit. Pat. 542,471.

    Google Scholar 

  • Sherrard, E. C. and E. E. Harris (Sept. 7, 1944), “Simultaneous Production of Pulp and Hydrogenated Products from Lignocellulose.” U.S. Pat. 2,328,749.

    Google Scholar 

  • Sherrard, E. C., E. E. Harris and J. F. Saeman (Nov. 5, 1940b), “Hydrogenation of Lignin and Waste Pulp Liquors.” U.S. Pat. 2,220,624.

    Google Scholar 

  • Shimada, M., T. Fukuzuka and T. Higuchi (1971), “Ester Linkages of P-Coumaric Acid in Bamboo and Grass Lignins.” Tappi 54, pp. 72–78, (Engl.).

    Google Scholar 

  • Shimada, M. (1972), “Biochemical Studies on Bamboo Lignin and Methoxylation in Hardwood and Softwood Lignins.” Wood Res. (Kyoto) 53, pp. 1965, (Engl.).

    Google Scholar 

  • Shishkin, V. A. and Yu. L. Yur’ev (1975), “Catalytic Cracking of Sedimentation Tar Oils from Pyrolysis of Hydrolysis Lignin.” Izv. VUZ, Lesnoi Zh. 18, No. 3, pp. 113–116, (Russ.).

    Google Scholar 

  • Shorygina, N. N. and T. Ya. Kefeli (1950), “Cleavage of Lignin with Metallic Sodium in Liquid Ammonia. IV.,” Zhur. Obshchei Khim. 20, pp. 1199–1208 (Russ.).

    Google Scholar 

  • Shorygina, N. N. and T. Ya. Kefeli (1947), “The Decomposition of Lignin by Metallic Sodium in Liquid Ammonia,” J. Gen. Chem. (U.S.S.R.) 17, pp. 2058–2065 (Russ.).

    Google Scholar 

  • Shorygina, N. N. and T. Ya. Kefeli (1948), “Reaction of Lignin with Metallic Sodium in Liquid Ammonia. II.,” Zhur. Obshchei Khim. 18, pp. 528–533 (Russ.).

    Google Scholar 

  • Shorygina, N. N., T. Ya. Kefeli and A. F. Semechkina (1949), “Cleavage of Lignin by Metallic Sodium in Liquid Ammonia,” Doklady Akad. Nauk, U.S.S.R. 64, pp. 689–692 (Russ.).

    Google Scholar 

  • Shorygina, N. N., T. Kefeli and A. F. Semechkina (1949), “Cleavage of Lignin by Metallic Sodium in Liquid Ammonia III.,” Zhur. Obshchei Khim. 19, pp. 1558–1566 (Engl. translation).

    Google Scholar 

  • Singerman, G. M. (1980), “Methyl Aryl Ethers From Coal Liquids as Gasoline Extenders and Octane Improvers,” Gulf Research and Development Co., Pittsburgh, PA 15230, report prepared under contract No. DE-AC01–79C50022.

    Google Scholar 

  • Sjöström, E. (1981), “Wood Chemistry-Fundamentals and Application,” NY: Academic Press.

    Google Scholar 

  • Smilga, A. K., P. P. Erin’sh, G. F. Zakis and M. P. Gavars (1975), “Calculation Method for Obtaining Differential Infrared Spectra of Lignin.” Khim. Drev. (Riga) No. 1, pp. 50–55, (Russ.).

    Google Scholar 

  • Snajberk, K. and E. Zavarin (August 1970), “Hydrogenolysis of White Fir Lignin Using Metallic Nickel Catalyst Generated in Situ.” Tappi 53, No. 8, pp. 1507–1509.

    Google Scholar 

  • Snell, G. J. and D. T. A. Huibers (Oct. 11, 1983), “Lignin Cracking Using Fast Fluidized Bed Reactions.” U.S. Pat. 4,409,416. 6 pp.

    Google Scholar 

  • Sobolev, I., H. G. Arlt and C. Schuerch (1957), “Alkaline Hydrogenation Pulping.” Ind. Eng. Chem. 49, pp. 1399–1400.

    Google Scholar 

  • Sobolev, I. and C. Schuerch (1958), “Alkaline Hydrogenation Pulping.” Tappi 41, pp. 545–551.

    Google Scholar 

  • Sogo, M., T. Ishihara and K. Hata (1966), “Chemical Studies on Bark.” (13). “Hydrogenolysis of Outer Bark Lignin of Pinus Densiflora.” J. Japan Wood Res. Soc. 122, pp. 96–101, (Eng.; Jap. sum.).

    Google Scholar 

  • Sokolova, I. V., V. D. Nimirovskii and M. N. Raskin (1982), “Animated Products of Lignin Degradation.” Khim. Drev. 54–56. (Russ.)

    Google Scholar 

  • Soltes, E. J. (1983), “Hydrocarbons from Lignocellulosic Residues.” J. Appl. Polymer Sci. (Appl. Polymer Symp.) 37, No. 2, pp. 775–786 (Engl.).

    Google Scholar 

  • Soltes, E. J. and T. J. Elder (1981) in “Organic Chemicals from Biomass”, I. S. Goldstein Ed., CRC: Boca Raton, Fla., p. 63.

    Google Scholar 

  • Sorensen, N. A. and J. Mehlum (26 Jun 1956), “Vanillin,” U.S. Pat. 2,752,394.

    Google Scholar 

  • Stavitskii, V. D. (1979), “Lignin-Tar Binder.” Avtomobi Unye Dorogi No. 1, pp. 20–22 (Russ.).

    Google Scholar 

  • Stromskaya, G. I., E. I. Chupka and S. V. Stromskii (1977), “Reduction of Lignin and Lignin Model Compounds with Amalgams.” Khim. Drev. (Riga) No. 1, pp. 78–82, (Russ.).

    Google Scholar 

  • Sudo, K. -I., B. H. Hwang and A. Sakakibara (1979), “Hydrogenolysis of Protolignin.” (14). “Isolation of a Dimeric Compound with alpha-0-gamma Linkage.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 25, No. 1, pp. 61–66, (Engl.; Jap. sum.).

    Google Scholar 

  • Sudo, K., B. H. Hwang and A. Sakakibara (1978), “Isolation of alpha-0-gamma Compound From Hydrogenolysis Products of Lignin.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 24, No. 6, pp. 242–245, (Engl.).

    Google Scholar 

  • Sudo, K., D. J. Mullord and J. M. Pepper (1981), “Lignin and Related Compounds.” (8). “Lignin Monomers and Dimers From Hydrogenolysis of Aspen Poplar Wood Using Rhodium-on-Charcoal Catalyst.” Can. J. Chem. 59, No. 7, pp. 1029–1031, (Engl.; (Fr. sum.).

    Google Scholar 

  • Sudo, K. and J. M. Pepper (1982), “Lignin and Related Compounds.” (9). “Isolation of a Dimer with a Benzylisochroman Structure From Hydrogenolysis Products of Aspen (Populus Tremuloides) Lignin.” Can. J. Chem. 60, No. 2, pp. 229–230, (Fr. sum.).

    Google Scholar 

  • Sudo, K. and A. Sakakibara, A. (1972), “Isolation of a New Trimeric Hydrogenolysis Product with Diphenyl Linkage from Ezomatsu (Picea Jezoensis) Wood Lignin.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 18, No. 10, pp. 517–518, (Engl.).

    Google Scholar 

  • Sudo, K. -I. and A. Sakakibara (1973), “Isolation of New Dimeric and Trimeric Condensed Type Compounds From Hydrogenolysis Products of Protolignin.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 19, 4, pp. 201–202 (Engl.).

    Google Scholar 

  • Sudo, K. -I. and A. Sakakibara (1973), “Hydrogenolysis of Protolignin.” (7). “Isolation of D,L-Syringaresinol, Biphenyl, and Diarylpropane from Hardwood Lignin.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 19, No. 4, pp. 165–169, (Engl.; Jap. sum.).

    Google Scholar 

  • Sudo, K. -I. and A. Sakakibara (1974), “Hydrogenolysis of Protolignin.” (II). “Isolation of a Dimer With C(beta)-C(6) and a Trimer with Two C(beta)-C(5) Linkages.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 20, No. 8, pp. 396–401, (Engl.; Jap. sum.).

    Google Scholar 

  • Sudo, K. -I. and A. Sakakibara (1974), “Hydrogenolysis of Protolignin.” (9). “Isolation of a Trimeric Compound Linked with Biphenyl and C(beta)-C(5) Linkages.” (10). “Isolation of Two Dimeric Compounds With beta-Axyl Ether Linkage.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 20, No. 7, pp. 327–335, (Engl.; Jap. sum.).

    Google Scholar 

  • Sudo, K. and A. Sakakibara (1975), “Hydrogenolysis of Protolignin.” (12). “Isolation of Dimeric and Trimeric Compounds with Carbon-to-Carbon Linkages.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 21, No. 3, pp. 164–169, (Engl.: Jap. sum.).

    Google Scholar 

  • Sudo, K. -I. and A. Sakakibara (1977), “Hydrogenolysis of Protolignin.” (13). “Isolation of Trimeric Biphenyl- and Lignin-Type Compounds.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 23, No. 3, pp. 151–155 (Engl; Jap. sum.).

    Google Scholar 

  • Sugo, M., T. Ishihara and K. Hata (1966), “Bark.” XIII. “Hydrogenolysis of Outer Bark Lignin of Pinus Densiflora.” Nippon Mokuzai Gakkaishi 12, pp. 96–101. (Engl.).

    Google Scholar 

  • Sukhanovskii, S. I., E. I. Akhima, E. I. Evstiteeva, T. A. Podgornaya, A. I. Kalvins, K. Abele, I. Alsups, A..I. Kul’kwits and O. Kiselis (1964), “Thermal Decomposition of Hydrolysis Lignin by Noncondensable Gases in a Retort with Internal Heating,” Khim. Pererabotka i Zashchita Drevesing, Akad. Nauk Latv. SSSR, Inst. Khim. Drevesing, pp. 87–101 (Russ.).

    Google Scholar 

  • Sukhanovskii, S. I., E. I. Akhmina, T. A. Podgornaya, E. S. Bezinozgin, A. G. Nemchenko and Yu. D. Yudkevich (1964), “Contact Pyrolysis of the Residual Resin After Thermolysis of Hydrolytic Lignin,” Gidrolizn. i Lesokhim. Prom. 17, No. 5, pp. 17–18 (Russ.).

    Google Scholar 

  • Sundstrom, D. W. and H. E. Klei (1982), “Uses of Byproducts from Alcohol Fuel Processes,” Biotechnol. Bioeng. Symp., No. 12, pp. 45–56.

    Google Scholar 

  • Suty, L. and E. Golis (1972), “Chemical Structure of Beech Lignin and its Changes During Aqueous Hydrolysis.” Cellulose Chem. Technol. 6, pp. 485–491.

    Google Scholar 

  • Tegai, F., E. M. Ryzhkov, V. I. Mev’shov and V. M. Kirilets (1985), “Liquefaction of Hydrolysis Lignin by Supercritical Dissolution in Lower Aliphatic Alcohols.” 1. “Liquefaction in Isopropyl Alcohol and Group Composition of the Liquid Product,” Khim. Drev. (Riga), No. 2, pp. 81–85 (Russ.).

    Google Scholar 

  • Tomlinson, G. H. and H. Hibbert (1936), “Lignin and Related Compounds” XXIII. “The Preparation and Methylation of Spruce Lignin Sulfonic Acids,” J. Am. Chem. Soc. 58, p. 345.

    Google Scholar 

  • Vasyunina, N. A., A. A. Balandin, S. V. Chepigo and G. S. Barysheva (1960), “Catalytic Hydrogenation of Lignin.” Izvest. Akad. Nauk S.S.S.R., Otdel Khim. Nauk, p. 1312.

    Google Scholar 

  • Vincent, G. G. (1980), “Oxygen-Containing Aromatic Compounds Obtained From Lignin.” Proc. Bio-Energy ′80 World Cong. (Atlanta), pp. 299–300, (Engl.) (Avail. from Bio-Energy Council, Washington, DC 20006).

    Google Scholar 

  • Vogelzang, M., C. Li, G. Schnit, B. Gates and L. Petrakis (1983), “Hydrogenation of 1-Naphthol: Activities and Stabilities of Molybdena and Related Catalysts.” J. of Catalysts 84, pp. 170–177.

    Google Scholar 

  • Voss, W. (1968), “Use of Wood as a Raw Material for the Chemical Industry.” Wiss. Z. Tech. Univ. Dresden 17, No. 5, pp. 1405–1413 (1968). (Ger.).

    MathSciNet  Google Scholar 

  • Vuori, A. and J. B. Bredenberg (1984a), “Hydrogenolysis and Hydrocracking of the Carbon-Oxygen Bond.” 5. “Hydrogenolysis of 4-Propylguaiacol by Sulfided Cobalt Oxide/Molybdenum Oxide/gamma-Aluminum Oxide.” Holzforschung 38, No. 5, pp. 253–262, (Engl.; Ger. sum.).

    Google Scholar 

  • Vuori, A. and J. B. Bredenberg (1984b), “Hydrogenoiysis and Hydrocracking of the Carbon-Oxygen Bond.” 4. “Thermal and Catalytic Hydrogenoiysis of 4-Propylguaiacol,” Holzforschung 38, No. 3, pp. 133–140 (Engl.; Ger. sum.).

    Google Scholar 

  • Vuori, A. and J. B. Bredenberg (1985), “Thermolysis of Substituted Anisoles,” Paper presented at ACS Div. of Fuel Chem., Miami Beach, Florida, April 28-May 3, 1985, Preprints Vol. 30, No. 1, pp. 366–378.

    Google Scholar 

  • Vuori, A., T. Karinen and J. B. Bredenberg (1984), “Thermolysis of Anisole,” Finn. Chem. Lett. No. 4–5, pp. 89–94.

    Google Scholar 

  • Wada, I., M. Ohta and A. Sakakibara (1969), “Hydrogenoiysis of Protolignin.” II. “Isolation of Some Hydrogenoiysis Products.” J. Japan Wood Res. Soc. 15, No. 5, pp. 218–221, (Engl.; Jap. sum.).

    Google Scholar 

  • Wada, I. and A. Sakakibara (1969), “Hydrogenoiysis of Protolignin.” I. “Hydrogenoiysis Products Under Various Reaction Conditions.” J. Japan Wood Res. Soc. 15, No. 5, pp. 214–218, (Engl.; Jap. sum.).

    Google Scholar 

  • Weigold, H. (1982), “Behavior of Co-Mo-A12O3 Catalysts in the Hydrodeoxygenation of Phenols,” Fuel 61, pp. 1031–1036.

    Google Scholar 

  • Weisser, O. and S. Landa (1973), “Sulfide Catalysts, Their Properties and Applications,” Pergamon Press: New York.

    Google Scholar 

  • Wenzl, H. F. J. (1970), “Chemical Technology of Wood.” Acad. Press (N.Y. and London), 692 p. (Transl. from Ger. by F. E. & D. A. Brauns).

    Google Scholar 

  • Wienhaus, O., F. Fischer and R. Schiene (1976), “Hydrogenoiysis of Lignin— A Promising Degradation Process to Obtain Fundamental Organic Chemicals.” Zellstoff Papier 25, No. 4, pp. 109–116 (Ger.).

    Google Scholar 

  • Wienhaus, O., R. Schiene and F. Fischer (1980), “Hydrogenoiysis and Pyrolysis of Lignins.” Zellstoff Papier 29, No. 3, pp. 125–128, (Ger.).

    Google Scholar 

  • Yamamoto, K. (1939), “Catalytic Reduction of Cresols at High Temperatures and High Pressures,” J. Chem. Soc., Japan 60, pp. 451–453.

    Google Scholar 

  • Yamashina, H. and A. Sakakibara (1974), “Hydrogenoiysis of Protolignin.” (II). “Isolation of Degradation Products from Hardwood Lignin.” Res. Bull. Coll. Expt. Forests Hokkaido Univ. 31, No. 1, pp. 51–62, (Jap.; Engl. sum.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1977), “Hydrogenoiysis of Protolignin in Compression Wood.” (4). “Isolation of a Diphenyl Ether and Three Dimeric Compounds with Carbon-to-Carbon Linkage.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 23, No. 8, pp. 383–387, (Engl.; Jap. sum.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1977), “Hydrogenoiysis of Protolignin in Compression Wood.” (3). “Isolation of Four Dimeric Compounds with Carbon-to-Carbon Linkage.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 23, No. 2, pp. 114–119, (Engl.; Jap. sum.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1975), “Hydrogenoiysis of Protolignin in Compression Wood.” (I). “Isolation of Two Dimers With C(beta)-C(5) and C(beta)-C(3) Linkages Composed of p-Hydroxyphenyl and Guaiacyl Nuclei and Two p-Hydroxyphenyl Nuclei, Respectively.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 21, No. 6, pp. 370–375, (Engl.; Jap. sum.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1975), “Isolation of a New Dimeric “Condensed Type” Compound from Hydrogenolysis Products of Compression Wood Lignin.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 21, No. 11, pp. 639–640 (Engl.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1976), “Hydrogenolysis of Protolignin in Compression Wood.” (2). “Isolation of Two Dimers with beta-Aryl Ether Linkages and Phenylisochroman Structure.” J. Japan Wood Res. Soc. (Mokuzai Gakkaishi) 22, No. 11, pp. 606–612, (Engl.; Jap. sum.).

    Google Scholar 

  • Yasuda, S. and A. Sakakibara (1981), “Hydrogenolysis of Protolignin in Compression Wood.” (5). “Isolation of Two Trimeric Compounds With gamma-Lactone Ring.” Holzforschung 35, No. 4, pp. 183–187, (Engl.; Ger. sum.).

    Google Scholar 

  • Zarubin, M. and D. Tishchenko (1960), “Alkali Hydrolysis of Scholler Lignin Yielding Low-Molecular-Weight Substances,” Zhur. Priklad. Khim. 33, pp. 2576–2581 (Russ.).

    Google Scholar 

  • Zarubin, M. and D. Tishchenko (1959), “Low-Molecular Substances from Highly Condensed Hydrolytic Lignin by Alkali Hydrolysis,” Zhur. Priklad. Khim. 32, pp. 395–399 (Russ.).

    Google Scholar 

  • Ziemelis, U. K., L. K. Dubava, G. E. Domburg, V. P. Paicha and R. V. Luksa (1979), “Rapid Thermolysis of Hyrolysis Lignin.” Gidroliz. Lesokhim. Prom. 2, pp. 8–10, (Russ.).

    Google Scholar 

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Chum, H.L., Johnson, D.K., Black, S., Ratcliff, M., Goheen, D.W. (1988). Lignin Hydrotreatment to Low-Molecular-Weight Compounds. In: Böer, K.W. (eds) Advances in Solar Energy. Advances in Solar Energy, vol 4. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9945-2_2

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