Abstract
The use of lignocellulosic biomass as a renewable feedstock for the production of chemicals requires the development of new chemical processing technologies. Since many traditional solvents and catalyst systems are incompatible with carbohydrates and lignins, we are exploring the use of new solvent systems that can sustain catalytic reactions. More specifically, we are studying the use of ionic solvents that are liquid at room temperature, and that are known to have unique solvent properties. In order better to understand the fundamental chemistry of processing lignocellulosic biomass using ionic solvent systems, we are exploring chemical reactions with simple carbohydrate and lignin building blocks.
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References
Armor, J.N. (1999) Striving for catalytically green processes in the 21π century, Appl. Catal. A 189, 153–162.
Bozell, J.J., Hames, R.H., and Dimmel, D.R. (1995) Cobalt-Schiff Base Complex Catalyzed Oxidation of Para-Substituted Phenolics. Preparation of Benzoquinones, J. Org. Chem. 60, 2398–2404.
Collins, P.M. and Ferner, RJ. (1995) Monosaccharides-Their Chemistry and Their Roles in Natural Products, John Wiley & Sons, New York.
Anastas, P.T., Bartlett, L.B., Kirchhoff, M.M., and Williamson T.C. (2000) The role of catalysis in the design, development, and implementation of green chemistry, Catal. Today 55, 11–22.
Welton, T. (1999) Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis, Chem. Rev. 99, 2071–2083.
Huddleston, J.G., Willauer, H.D., Swatloski, R.P., Visser, A.E., and Rogers, R.D. (1998) Room temperature ionic liquids as novel media for ‘clean’ liquid-liquid extraction, Chem. Commun. 1765–1766.
Ilankumaran, P. and Verkade, J.G. (1999) Highly Selective Acylation of Alcohols Using Enol Esters Catalyzed by Iminophosphoranes, J. Org. Chem. 64, 9063–9066.
Bredenkamp, M.W. and Spies, H.S.C. (2000) Tin-Mediated Equilibration of the Benzoate Esters of Methyl 4,6-O-Benzylidene-D-D-Glucopyranoside, Tetrahedron Lett. 41, 543.
Barrett, A.G.M. and Braddock, D.C. (1997) Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid, Chem. Commun. 351–352.
Sakamoto, K., Hamada, Y., Akashi, H., Orita, A., and Otera, J. (1999) Novel Dimeric Organotin Cations: Highly Effetive Alcohol Acetylation Catalysts, Organometallics 18, 3555–3557.
Jyojima, T., Miyamoto, N., Ogawa, Y., Matsumura, S., and Toshima, K. (1999) Novel Stereocontrolled Glycosidations of Olivoses Using Montmorillonite K-10 as an Environmentally Benign Catalyst, Tetrahedron Lett. 40, 5023–5026.
Saravanan, P. and Singh, V.K. (1999) An Efficient Method for Acylation Reactions, Tetrahedron Lett. 40, 2611–2614.
Schlotterbeck, A., Lang, S., Wray, V., and Wagner, F. (1993) Lipase-catalyzed monoacylation of fructose, Biotechnol. Lett. 15, 61–64.
Steverick-de Zoete, M.C., Kneepkens, M.F.M., de Waard, P., Woudenberg-van Oosterom, M., Gotlieb, K.F., and Slaghek, T.M. (1999) Enzymatic synthesis and NMR studies of acylated sucrose acetates, Green Chem. June, 153–156.
Ward, O.P., Fang, J., and Li, Z. (1997) Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid, Enzym. Microb. Technol. 20, 52–56.
Choudary, B.M., Kantam, M.L., Neeraja, V., Bandyopadhyay, T., and Reddy, P.N. (1999) Vanadyl(IV) acetate, a reusable catalyst for acetylation of alcohols, J. Mol. Cat. A: Chem. 140, 25–29.
Pasquali, M., Marchetti, F., and Floriani, C. (1979) Deoxygenation of Oxovanadium(IV) Complexes: A Novel Synthetic Route to Dichlorovanadium(IV) Chelate Complexes, Inorg. Chem. 18, 2401–2404.
Schmidt, H. and Render, D. (1998) The preparation and synthetic potential of chlorovanadhim(V and IV) complexes supported by enamines and bis(enamines), Inorg. Chim. Acta 267, 229–238.
Monteiro, A.L., Zinn, F.K., de Souza, R.F., and Dupont, J. (1997) Asymmetric hydrogenation of 2-arylacrylic acids catalyzed by immobilized Ru-BINAP complex in 1-n-buty1-3-methylimidazolium tetrafluoroborate molten salt, Tetrahedron: Asymm. 8, 177–179.
Collet, A. (1987) Cyclotriveratrylenes and cryptophanes, Tetrahedron 43, 5725–5759.
Al-Farhan, E., Keehn, P.M., and Stevenson, R. (1992) Cyclo-oligomerization of Veratryl Alcohol with Trifluoroacetic Acid, Tetrahedron Lett. 33, 3591–3594.
Jimenez, F.G., Perezamador, M.C., and Alcayde, J.R. (1969) Ring B conformation in 9,10-dihydroanthracenes by nuclear magnetic resonance, Can. J. Chem. 47, 4489–4491.
Konishi, H., Sakakibara, H., Kobayashi, K., and Morikawa, O. (1999) Synthesis of the parent resorcin[4]arene, J. Chem. Soc., Perkin Trans. 1, 2583–2584.
Cruz-Almanza, R., Shiba-Matzumoto, I., Fuentes, A., Martinez, M., Cabrera, A., Cardenas, J. and Salmon, M. (1997) Oligomerization of benzylic alcohols and its mechanism, J. Mol. Cat. A: Chem. 126, 161–168.
Falana, O.M., Al-Farhan, E., Keehn, P.M., and Stevenson, R. (1994) High Yield Synthesis of the Parent C-Unsubstituted Calix[4]resorcinarene Octamethyl Ether, Tetrahedron Lett. 35, 65–68.
Banks, R.E., François, P.-Y., and Preston, P.N. (1992) Polymerization of benzyl alcohol in anhydrous hydrogen fluoride: and efficient synthesis of poly(phenylenemethylene), Polymer 33, 3974–3975.
Percec, V., Cho, C.G., and Pugh, C. (1991) Cyclotrimerization versus Cyclotertramerization in the Electrophilic Oligomerization of 3,4-Bis(methyloxy)benzyl Derivatives, Macromolecules 24, 3227–3234.
Carmichael, A.J., Earle, M.J., Holbrey, J.D., McCormac, P.B., and Seddon, K.R. (1999) The Heck Reaction in Ionic Liquids: A Multiphasic Catalyst System, Org. Lett. 1, 997–1000.
Ellis, B., Keim, W., and Wasserscheid, P. (1999) Linear dimerisation of but-1-ene in biphasic mode using buffered cbloroaluminate ionic liquid solvents, Chem. Commun. 337–338.
Keim, W., Vogt, D., Waffenschmidt, H., and Wasserscheid, P. (1999) New Method to Recycle Homogeneous Catalysts from Monophasic Reaction Mixtures by Using an Ionic Liquid Exemplified for the Rh-Catalysed Hydroformylation of Methy1-3-pentenoate, J. Cat. 186, 481–484.
Zim, D., de Souza, R.F., Dupont, J., and Monteiro, A.L. (1998) Regioselective Synthesis of 2-Arylpropionic Esters by Palladium-Catalyzed Hydroesterification of Styrene Derivatives in Molten Salt Media, Tetrahedron Lett. 39, 7071–7074.
Simon, L.C., Dupont, J., de Souza, R.F. (1998) Two-phase n-butenes dimerization by nickel complexes in molten salt media, Appl. Cat. A 175, 215–220.
Chauvin, Y., Olivier, H., Wyrvalski, C.N., Simon, L.C., and de Souza, R. F. (1997) Oligomerization of n-Butenes Catalyzed by Nickel Complexes Dissolved in Organochloroaluminate Ionic Liquids, J. Catal. 165, 275–278.
Suarez, P.A.Z., Dullius, J.E.L., Einloft, S., de Souza, R.F., Dupont, J. (1997) Two-phase catalytic hydrogenation of olefins by Ru(II) and Co(II) complexes dissolved in 1-n-buty1-3-methylimidazolium tetrafluoroborate ionic liquid, Inorg. Chim. Acta 255, 207–209.
Einloft, S., Dietrich, F.K., de Souza, R.F, and Dupont, J. (1996) Selective two-phase catalytic ethylene dimerization by Ni(II) complexes/AlEtCl2 dissolved in organoaluminate ionic liquids, Polyhedron 15, 3257–3259.
Suarez, P.A.Z., Dullius, J.E.L., Einloft, S., de Souza, R.F., and Dupont, J. (1996) The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes, Polyhedron 15, 1217–1219.
Chauvin, Y., Einloft, S., and Olivier, H. (1995) Catalytic Dimerization of Propene by Nickel-Phosphine Complexes in 1-Buty1-3-methylimidazolium Chloride/AlEtxCl3-x (x=0,1) Ionic Liquids, Ind. Eng. Chem. Res. 34, 1149–1155.
Sheldon, R.A., Arends, I.W.C.E., and Lempers, H.E.B. (1998) Liquid phase oxidation at metal ions and complexes in constrained environments, Catal. Today 41, 387–407.
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Moens, L., Khan, N. (2003). Application of Room-Temperature Ionic Liquids to the Chemical Processing of Biomass-Derived Feedstocks. In: Rogers, R.D., Seddon, K.R., Volkov, S. (eds) Green Industrial Applications of Ionic Liquids. NATO Science Series, vol 92. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0127-4_9
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DOI: https://doi.org/10.1007/978-94-010-0127-4_9
Publisher Name: Springer, Dordrecht
Print ISBN: 978-1-4020-1137-5
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