Abstract
Macrocyclic complexes were synthesized and ionically bonded with montmorillonite clay. Such catalysts are found to have excellent thermal stability and can be used for the industrially important catalytic reactions. The oxidation of cyclohexane without any promoter or solvent has been carried out using molecular oxygen. Based on the catalytic mechanism, experimental data were fitted to determine various rate constants.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Reichle WT (1986) Synthesis of anionic clay minerals (mixed metal hydroxides, hydrotalcite). Solid State Ionics 22:135–141
Vaccari A (1998) Preparation and catalytic properties of cationic and anionic clays. Catal Today 41:53–71
Vaughan DEW (1988) Pillared clays – a historical perspective. Catal Today 2:87–198
Vaccari A (1999) Clays and catalysis: a promising future. Appl Clay Sci 14:161–198
Rhodes CN, Brown DR (1993) Surface properties and porosities of silica and acid-treated montmorillonite catalyst supports: influence on activities of supported ZnCl2 alkylation catalysts. J Chem Soc Faraday Trans 9:1387–1391
Liu GH, Ko AN, Chang YC (1995) Synthesis and properties of pillared montmorillonite formed by intercalation of transition metal macrocyclic complexes. Micropor Mater 5:61–67
Mishra T, Parida K (1998) Transition metal oxide pillared clay: 5. Synthesis, characterization and catalytic activity of iron–chromium mixed oxide pillared montmorillonite. Appl Catal A Gen 174:91–98
Vicente MA, Belver C, Trujillano R, Rives V, Alvarez AC, Lambert JF, Korili SA, Gandia LM, Gil A (2004) Preparation and characterization of Mn and Co supported catalysts derived from Al pillared clays and Mn and Co complexes. Appl Catal A 267:47–58
Akcay M (2004) The catalytic acylation of alcohols with acetic acid by using Lewis acid character pillared clays. Appl Catal A 269:157–160
Belver C, Bañares-Muñoz MA, Vicente MA (2004) Fe-saponite pillared and impregnated catalysts I. Preparation and characterization. Appl Catal A 50:101–112
Carriazo JG, Guelou E, Barrault J, Tatibouet JM, Moreno S (2003) Catalytic wet peroxide oxidation of phenol over Al–Cu or Al–Fe modified clays. Appl Clay Sci 22:303–308
Barrault J, Tatiboue JM, Papayannakos N (2000) Catalytic wet peroxide oxidation of phenol over pillared clays containing iron or copper species. C R Acad Sci Paris Serie IIc Chim Chem 3:777–783
Ovejero G, Sotelo JL, Martinez F, Melero JA, Gordo L (2001) Wet peroxide oxidation of phenolic solutions over different iron-containing zeolitic materials. Ind Eng Chem Res 40(18):3921–3928
Guo J, Dahhan MA (2003) Catalytic wet oxidation of phenol by hydrogen peroxide over pillared clay catalyst. Ind Eng Chem Res 42(12):2450–2460
Carriazo JG, Guelou E, Barrault J, Tatiboue JM, Moreno S (2003) Catalytic wet peroxide oxidation of phenol over Al–Cu or Al–Fe modified clays. Appl Clay Sci 22:303–308
Mei JG, Yu SM, Cheng J (2004) Heterogeneous catalytic wet peroxide oxidation of phenol over delaminated Fe–Ti-PILC employing microwave irradiation. Catal Commun 5:437–440
Guo J, Dahhan MA (2005) Catalytic wet air oxidation of phenol in concurrent downflow and upflow packed-bed reactors over pillared clay catalyst. Chem Eng Sci 60:735–746
Jinjun L, Zheng J, Zhengping H, Xiuyan X, Yahui Z (2005) Pillared laponite clays-supported palladium catalysts for the complete oxidation of benzene. J Mol Catal A Chem 225: 173–179
Timofeeva MN, Khankhasaeva ST, Badmaeva SV, Chuvilin AL, Burgina EB, Ayupov AB, Panchenko VN, Kulikova AV (2005) Synthesis, characterization and catalytic application for wet oxidation of phenol of iron-containing clays. Appl Catal B 59:243–248
Martinez F, Melero JA, Botas J, Pariente MI, Molina R (2007) Treatment of phenolic effluents by catalytic wet hydrogen peroxide oxidation over Fe2O3/SBA-15 extruded catalyst in a fixed-bed reactor. Ind Eng Chem Res 46(13):4396–4405
Ramirez JH, Lampinen M, Vicente MA, Costa CA, Madeira LM (2008) Experimental design to optimize the oxidation of orange II dye solution using a clay-based Fenton-like catalyst. Ind Eng Chem Res 47(2):284–294
Polubesova T, Chen Y, Navon R, Chefetz B (2008) Interactions of hydrophobic fractions of dissolved organic matter with Fe3+- and Cu2+–montmorillonite. Environ Sci Technol 42(13):4797–4803
Gokulakrishnan N, Pandurangan A, Sinha PK (2009) Catalytic wet peroxide oxidation technique for the removal of decontaminating agents ethylenediaminetetraacetic acid and oxalic acid from aqueous solution using efficient Fenton type Fe-MCM-41 mesoporous materials. Ind Eng Chem Res 48(3):1556–1561
Chen TJ, Li G, Ding X, Sheng G, Mai JFB, O’Shea KE (2008) Characterization and the photocatalytic activity of TiO2 immobilized hydrophobic montmorillonite photocatalysts. Degradation of decabromodiphenyl ether (BDE 209). Catal Today 139:69–76
Achma RB, Ghorbel A, Sayadi S, Dafinov A, Medina F (2008) A novel method of copper-exchanged aluminum-pillared clay preparation for olive oil mill wastewater treatment. J Phys Chem Solids 69:1116–1120
Onda A, Suzuki Y, Kajiyoshi K, Yanagisawa K (2006) Catalytic performance of autoclave liners in the wet oxidation of naphthalene. Ind Eng Chem Res 45(7):2194–2198
Gu C, Li H, Teppen BJ, Boyd S (2008) Octachlorodibenzodioxin formation on Fe(III)–montmorillonite clay. Environ Sci Technol 42(13):4758–4763
Anisia KS, Kumar A (2007) Oxidation of cyclohexane with molecular oxygen in presence of characterized macrocyclic heteronuclear FeCu complex catalyst ionically bonded to zirconium pillared montmorillonite clay. J Mol Catal A Chem 271:164–179
Kalilur Rahiman A, Rajesh K, Shanmuga Bharathi K, Sreedaran S, Narayanan V (2009) Catalytic oxidation of alkenes by manganese(III) porphyrin-encapsulated Al, V, Si-mesoporous molecular sieves. Inorg Chim Acta 362:1491–1500
Liu YX, Zhang X, Guo L, Wu F, Deng NS (2008) Photodegradation of bisphenol A in the montmorillonite KSF suspended solutions. Ind Eng Chem Res 47(19):7141–7146
Remili C, Kaci M, Kachbi S, Bruzaud S, Grohens Y (2009) Photo-oxidation of poly styrene/clay nanocomposites under accelerated UV exposure: effect on the structure and molecular weight. J Appl Poly Sci 112:2868–2875
Bottino FA, Pasquale GD, Fabbri E, Orestano A, Pollicino A (2009) Influence of montmorillonite nano-dispersion on polystyrene photo-oxidation. Polym Degrad Stabil 94:369–374
Menesi J, Korosi L, Bazso E, Zllmer V, Richardt A, Dekany I (2008) Photocatalytic oxidation of organic pollutants on titania–clay composites. Chemosphere 70:538–542
Barros VB, Faria AL, MacLeod TCO, Morales LAB, Assis MD (2008) Ironporphyrin immobilized onto montmorillonite as a biomimetical model for azo dye oxidation. Int Biodeterior Biodegrad 61:337–344
Lan Y, Li C, Mao J, Jun Sun A (2008) Influence of clay minerals on the reduction of Cr6+ by citric acid. Chemosphere 71:781–787
Jiang J, Ma K, Zheng Y, Cai S, Li R, Ma J (2009) Cobalt salophen complex immobilized into montmorillonite as catalyst for the epoxidation of cyclohexene by air. Appl Clay Sci 45: 117–122
Sis BE, Khalili B, Abdollahifar A, Hashemi M (2007) Transition metal free oxidation of alcohols to carbonyl compounds using hydrogen peroxide catalyzed with LiCl on montmorillonite K10. Acta Chim Slov 54:635–637
Schuster H, Rios LA, Weckes PP, Hoelderich WF (2008) Heterogeneous catalysts for the production of new lubricants with unique properties. Appl Catal A Gen 348:266–270
Rode CV, Kshirsagar VS, Nadgeri JM, Patil KR (2007) Cobalt–salen intercalated montmorillonite catalyst for air oxidation of p-cresol under mild conditions. Ind Eng Chem Res 46:8413–8419
Anisia KS, Kumar A (2008) Synthesis of heterogeneous copper complex catalyst for oxidation of cyclohexane using molecular oxygen. Can J Chem Eng 86:1054–1061
Lal S, Anisia KS, Jhansi M, Kishore L, Anil Kumar (2007) Development of heterogeneous catalyst by ionically bonding macrocyclic Zr–Zr complex to montmorillonite clay for depolymerization of polypropylene. J Mol Catal A Chem 265:15–24
Dhakshinamoorthy A, Pitchumani K (2006) Clay-anchored non-heme iron–salen complex catalyzed cleavage of C=C bond in aqueous medium. Tetrahedron 62:9911–9918
Cardoso B, Pires J, Carvalho AP, Biernacka IK, Silva AR, Castro B, Freire C, (2005) Mn(III) salen complex immobilised into pillared clays by in situ and simultaneous pillaring/encapsulation procedures application in the heterogeneous epoxidation of styrene. Micropor Mesopor Mater 86:295–302
Dasa P, Biernacka IKZ, Silva AR, Carvalho AP, Pires J, Freire C (2006) Encapsulation of chiral Mn(III) salen complexes into aluminium pillared clays: application as heterogeneous catalysts in the epoxidation of styrene. J Mol Catal A Chem 248:135–143
Kameyama H, Narumi F, Hattori T, Kameyamaa H (2006) Oxidation of cyclohexene with molecular oxygen catalyzed by cobalt porphyrin complexes immobilized on montmorillonite. J Mol Catal A Chem 258:172–177
Ramaswamy V, Malwadkar S, Chilukuri S (2008) Cu–Ce mixed oxides supported on Al-pillared clay: effect of method of preparation on catalytic activity in the preferential oxidation of carbon monoxide. Appl Catal B 84:21–29
Tandon PK, Singh SB, Srivastava M (2007) Synthesis of some aromatic aldehydes and acids by sodium ferrate in presence of copper nano-particles adsorbed on K 10 montmorillonite using microwave irradiation. Appl Organometal Chem 21:264–267
Faria AL, MacLeod TCO, Assis MD (2008) Carbamazepine oxidation catalyzed by iron and manganese porphyrins supported on aminofunctionalized matrices. Catal Today 133–135: 863–869
Bhor MD, Nandurkar NS, Bhanushali MJ, Bhanage BM (2008) Ultrasound promoted selective synthesis of 1,10-binaphthyls catalyzed by Fe impregnated pillared montmorillonite K10 in presence of TBHP as an oxidant. Ultrason Sonochem 15:195–202
Dhakshinamoorthy A, Pitchumani K, (2009) Clay-supported ceric ammonium nitrate as an effective, viable catalyst in the oxidation of olefins, chalcones and sulfides by molecular oxygen. Catal Commun 10:872–878
Das P, Kuźniarska-Biernacka I, Silva AR, Carvalho AP, Pires J, Freire C (2006) Encapsulation of chiral Mn(III) salen complexes into aluminium pillared clays: application as heterogeneous catalysts in the epoxidation of styrene. J Mol Catal A Chem 248:135–143
Vedrine JC, Millet JMM, Volta J (1996) Molecular description of active sites in oxidation reactions: acid–base and redox properties, and role of water. Catal Today 32:115–123
Corma A, Gracia H (2003) Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem Rev 103:4307–4365
Ghorbel A, Hoang-Van C, Teichner SJ (1973) Catalytic activity of amorphous alumina prepared in aqueous media: I. Catalytic activity in isomerization of butene-1. J Catal 30:298–308
Adeeva V, Deehan JW, Janchen J, Lei GD, Schunemaron V, Vandevan LJM, Sachtler WMH, Vansanten RA (1995) Acid sites in sulfated and metal promoted zirconium dioxide catalysts. J Catal 151:364–372
Ponec V (2001) Alloy catalysts: the concepts. Appl Catal A 222:31–45
Huber GW, Dumesic JA (2005) An overview of aqueous – phase catalytic process for the production of hydrogen and alkanes in a biorefinery. Catal Today 111:119–132
Davda RR, Shabaker JW, Huber GW, Cortright RD, Dumesic JA (2003) Aqueous-phase reforming of ethylene glycol on silica-supported metal catalysts. Appl Catal B 43:13–26
Davda RR, Shabaker JW, Huber GW, Cortright RD, Dumesic JA (2003) Aqueous-phase reforming of ethylene glycol on silica-supported platinum catalysts. Catal Lett 88:1–8
Lotero E, Liu Y, Lopez DE, Suwannakern K, Bruce DA, Godwin JG (2005) Synthesis of biodiesel with acid catalysis. Ind Eng Chem Res 44:5353–5363
Srivastava A, Prasad R (2000) Triglycerides based diesel fuels. Renew Sustain Energy Rev 4:111–133
Wasmus S, Kuver A (1999) Methanol oxidation and direct methanol fuel cells: a selective review. J Electroanal Chem 461:14–31
Hamnett A (1997) Mechanism and electro catalysis in the direct methanol fuel cells. Catal Today 38:445–457
Wang CY (2004) Fundamental model for fuel cell engineering. Chem Rev 104:4727–4766
Jones CJ (2001) d- and f-Block chemistry. Royal Society of Chemistry, UK
Gavrilova AL, Bosnich B (2004) Principles mononucleating and binucleating ligand design. Chem Rev 104:349–383
Sargeson AM (1966) Conformations of Coordinated Chelates In: Karlin RL (ed) Transition metal chemistry (New York), vol 3. Marcel Dekker, New York, NY, pp 303–343
Senkler GH Jr, Mislow KJ (1972) Barrier to pyramidal inversion in ethylmethylphenylarsine. J Am Chem Soc 94:291–296
Emmert C, Vereslet M, Tuchagues JP (1996) Pentadentate dinucleating ligands affording bis(μ-carboxylato-O,O)diiron(II) complexes. J Chem Soc Chem Commun 66:617–619
Tsukada N, Tamura O, Inoue Y (2002) Synthesis and structures of palladium and platinum a-frame complexes bridged by a novel binucleating ligand, N,N'-bis[(2-diphenylphosphino)phenyl]-formamidine. Organometallics 21:2521–2528
van Koningsbruggen PJ, Gatteschi D, de Graaff RAG, Haasnoot JG, Reedijk J, Zanchini C (1995) Isotropic and anisotropic magnetic exchange interactions through μ-N1,N2 1,2,4-triazole and μ-sulfato bridges: X-ray crystal structure, magnetic properties, and single-crystal EPR study of (μ-4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-N',N1,N2,N'')(μ-sulfato-O,O')[(sulfato-O)aquacopper(II)] triaquacopper(II) hydrate. Inorg Chem 34:5175–5182
Incarvito C, Rheingold AL, Qin CJ, Bosnich ALB (2001) Bimetallic reactivity on the use of oxadiazoles as binucleating ligands. Inorg Chem 40:1386–1390
Brooker S, Kelly RJ, Moubaraki B, Murray KS (1996) First dicopper(II) complex to contain bridging macrocyclic pyridazine units: structure, electrochemistry and magnetochemistry of [Cu2L(MeCN)2(ClO4)2][ClO4]2. J Chem Soc Chem Commun 2579–2580
Rooker S, de Geest DJ, Kelly RJ, Plieger PG, Moubaraki B, Murray KS, Jameson GJ (2002) Exchange-coupled high-spin, low-spin and spin-crossover dicobalt (II) complexes of a pyridazine-containing Schiff-base macrocycle: control of cobalt (II) spin state by choice of axial ligands. Chem Soc Dalton Trans 2080–2087
Tikkanen WR, Kruger C, Bomben KD, Jolly WL, Kaska WC, Ford PC (1984) Synthesis, characterization, and X-ray molecular structures of mono- and dinuclear copper complexes with 2,7-bis(2-pyridyl)-1,8-naphthyridine. Inorg Chem 23:3633–3638
Gajda T, Kramer R, Jansco A (2000) Structure, equilibrium and ribonuclease activity of copper (II) and zinc (II) complexes formed with a dinucleating bis-imidazole ligand. Eur J Inorg Chem 1635–1644
Kersting B (1998) Preparation, structures, and properties of dinuclear Ni and Pd complexes of tridentate amine-chalcogenolate ligands. Eur J Inorg Chem 1071–1077
Kersting B, Siebert D (1998) First examples of dinickel complexes containing the N3Ni(2-SR)3NiN3 core. Synthesis and crystal structures of [L2Ni2][BPh4]2 and [L3Ni2][BPh4]2 (L = 2,6-di(aminomethyl)-4-tert-butyl-thiophenolate). Inorg Chem 37:3820–3828
Kersting B, Siebert D (1999) Preparation, structure, and properties of a mixed-valent NiIINiIII amine–selenolate complex. Eur J Inorg Chem 189–193
Gange RR, Spiro CL, Smith TJ, Hamann CA, Thies WR, Shiemke AK (1981) The synthesis, redox properties and ligand binding of heterobinuclear transition-metal macrocyclic ligand complexes. Measurement of an apparent delocalization energy in a mixed-valent CuICuII complex. J Am Chem Soc 103:4073–4081
Farrugia LJ, Win GX (2003) Ver 1.64: an integrated systems of windows programs for the solution, refinement and analysis of single-crystal X-ray diffraction data. Department of Chemistry, University Of Glasgow, UK
Berezin IV, Denisov ET, Emanuel NM (1966) The oxidation of cyclohexane. Transl. by Allen KA. Pergamon Press, Oxford
Emanuel NM, Denisov ET, Maizus ZK (1967) Liquid phase oxidation of hydrocarbons. Plenum press, New York, NY
Suresh AK, Sharma MM, Sridhar T (2000) Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons. Ind Eng Chem Res 39:3958–3997
Schuchardt U, Cardoso D, Sercheli R, Pereira R, da Cruz RS, Guerreiro MC, Mandelli D, Spinacé EV, Pires EL (2001) Cyclohexane oxidation continues to be a challenge. Appl Catal A 211:1–17
Carvalho WA, Varaldo PB, Wallau M, Schuchardt U (1997) Mesoporous redox molecular sieves analogous to MCM-41. Zeolites 18:408–416
Arends WCE, Sheldon RA, Wallau M, Schuchardt U (1997) Oxidative transformations of organic compounds mediated by redox molecular sieves. Angew Chem Int Ed Engl 36:1144–1163
Lin SS, Weng HS (1994) Liquid phase oxidation of cyclohexane over CoAlPO-5. Appl Catal A Gen 118:21–31
Sakthivel A, Selvam P (2002) Mesoporous (Cr) MCM-41: a mild and efficient heterogeneous catalyst for selective oxidation of cyclohexane. J Catal 211:134–143
Steeman JWM, Kaarsemaker S, Hoftyzer PJ (1961) A pilot plant study of the oxidation of cyclohexane of air under pressure. Chem Eng Sci 14:139–149
Suresh AK, Sridhar T, Potter OE (1988) Autocatalytic oxidation of cyclohexane – modeling reaction kinetics. AIChE J 38:69–80
Mauryaa MR, Chandrakar AK, Chand S (2007) Oxovanadium (IV) and copper (II) complexes of 1,2-diaminocyclohexane based ligand encapsulated in zeolite-Y for the catalytic oxidation of styrene, cyclohexene and cyclohexane. J Mol Catal A Chem 270:225–235
Ebadi A, Safari N, Peyrovi MH (2007) Aerobic oxidation of cyclohexane with γ-alumina supported metallophthalocyanines in the gas phase. Appl Catal A 321:135–139
Silva AC, Fernandez TL, Carvalho NMF, Herbst MH, Bordinhao J, Horn A Jr, Wardell JL, Oestreicher EG, Antunes OAC (2007) Oxidation of cyclohexane catalyzed by bis-(2-pyridylmethyl)amine Cu(II) complexes. Appl Catal A 317:154–160
Alegria ECB, Kirillova MV, Martins LMDRS, Pombeiro AJL (2007) Pyrazole and trispyrazolylmethane rhenium complexes as catalysts for ethane and cyclohexane oxidations. Appl Catal A 317:43–52
Guan Huang G, Guo C, Tang S (2007) Catalysis of cyclohexane oxidation with air using various chitosan-supported metallotetraphenylporphyrin complexes. J Mol Catal A 261:125–130
Carvalho NMF, Horn A Jr, Antunes OAC (2006) Cyclohexane oxidation catalyzed by mononuclear iron (III) complexes. Appl Catal A 305:140–145
Esmelindro MC, Oestreicher EG, Marquez-Alvarez H, Dariva C, Egues SMS, Fernandes C, Bortoluzzi AJ, Drago V, Antunes OAC (2005) Catalytic oxidation of cyclohexane by a binuclear Fe(III) complex biomimetic to methane monooxygenase. J Inorg Biochem 99:2054–2061
Patcas F, Patcas FC. (2006) Reaction pathways and kinetics of the gas-phase oxidation of cyclohexane on NiO/γ-Al2O3 catalyst. Catal Today 117:253–258
Anand R, Hamdy MS, Gkourgkoulas P, Maschmeyer Th, Jansen JC, Hanefeld U (2006) Liquid phase oxidation of cyclohexane over transition metal incorporated amorphous 3D-mesoporous silicates M-TUD-1 (M = Ti, Fe, Co and Cr). Catal Today 117:279–283
Wen Y, Potter OE, Sridhar T (1997) Uncatalyzed oxidation of cyclohexane in a continuous reactor. Chem Eng Sci 52:4593–4605
Tolman CA, Druliner JD, Krusic PJ, Nappa MJ, Sieldel WC, Williams ID, Ittel SD (1988) Catalytic conversion of cyclohexylhydroperoxide to cyclohexanone and cyclohexanol. J Mol Catal 48:129–148
Tolman CA, Druliner JD, Nappa MJ, Herron N (1989). Alkane oxidation studies in DuPont’s Central Research Department, Chap X. In: Hill CL (ed) Activation and functionalization of alkanes. Wiley, New York, NY
Spielman M (1964) Selectivity in hydrocarbon oxidation. AIChE J 10:496–501
Alagy J, Trombouze P, Van Landeghem H (1974) Designing a cyclohexane oxidation reactor. Ind Eng Chem Proc Des Develop 13:317–323
Pohorecki R, Baldgya J, Moniuk W, Podgorska W, Zdrojkowski A, Wierzchowski PT (2001) Kinetic model of cyclohexane oxidation. Chem Eng Sci 56:1285–1291
Pohorecki R, Baldgya J, Moniuk W, Kryysztoforski A, Wojcik Z (1992) Liquid phase oxidation of cyclohexane – modeling and industrial scale process simulation. Chem Eng Sci 47:2559–2564
Steeman JWM, Kaarsemaker S, Hoftyzer PJ (1961) A pilot plant study of the oxidation of cyclohexane of air under pressure. Chem Eng Sci 14:139–149
Saunby JB, Kiff BW (1976) Liquid-phase oxidation – hydrocarbons to petrochemicals. Hydrocarbon Process 55:247
Modén B, Zhan B, Dakka J, Santiesteban JG, Iglesia E (2006) Kinetics and mechanism of cyclohexane oxidation on MnAPO-5 catalysts. J Catal 239:390–401
Nunes GS, Mayer I, Toma HE, Araki K (2005) Kinetics and mechanism of cyclohexane oxidation catalyzed by supramolecular manganese (III) porphyrins. J Catal 236:55–61
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer Science+Business Media, LLC
About this chapter
Cite this chapter
Lal, S., Anisia, K., Kumar, A. (2010). Heterogeneous Complex Catalysts Having Ionically Macrocyclic Complex Bonded to Montmorillonite Clay for Industrial Reactions. In: Gil, A., Korili, S., Trujillano, R., Vicente, M. (eds) Pillared Clays and Related Catalysts. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-6670-4_16
Download citation
DOI: https://doi.org/10.1007/978-1-4419-6670-4_16
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4419-6669-8
Online ISBN: 978-1-4419-6670-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)