Transiting from Adipic acid to bioadipic acid. 1, petroleum-based processes

Industrial and Engineering Chemistry Research

Volumn 54, Issue 1, 2015, Pages 1-46

  Bart, Jan C J ^a   Cavallaro, Stefano ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE; BIOMIMETIC MATERIALS; BIOMIMETICS; BYPRODUCTS; CATALYSTS; GREENHOUSE GASES; METAL HALIDES; NITROGEN OXIDES; OXIDANTS; TEMPERATURE; TOXIC MATERIALS;

COMMODITY CHEMICALS; CONCENTRATED NITRIC ACID; FOSSIL RAW MATERIALS; HOMOGENEOUS CATALYST; MULTISTEP PROCESS; REACTION CONDITIONS; REACTION PATHWAYS; RESEARCH AND DEVELOPMENT;

CHEMICAL REACTIONS;

EID: 84949133875     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie5020734     Document Type: Review

References (444)

1. Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry, 3rd Edition; VCH: New York, 1997 (translated by C. R. Lindley).
2. Castellan, A.; Bart, J. C. J.; Cavallaro, S. Industrial production and use of adipic acid. Catal. Today 1991, 9, 237-254.
3. Furman, M. S. Production of Cyclohexanone and Adipic Acid (in Russ.); Khimiya: Moscow, 1967.
4. Potnis, S. P.; Balakrishnan, P. V. Manufacture of adipic acid. Chem. Process. Eng. (Bombay) 1968, 2, 42-46.
5. (a) Vesel'chakova, T. L.; Preobrazhenskii, V. A.; Gol'dman, A. M.; Furman, M. S. Modern methods of preparing adipic acid. Khim. Prom. 1971, 47, 163-168.
6. (b) Vesel'chakova, T. L.; Preobrazhenskii, V. A.; Gol'dman, A. M.; Furman, M. S. Khim. Prom. 1971, 47, 243-250.
7. Luedeke, V. D. Adipic acid. In Encyclopedia of Chemical Processing and Design; McKetta, J. J., Ed.: Marcel Dekker: New York, 1977; Vol. 2, pp 128-146.
8. Danly, D. E.; Campbell, C. R. Adipic Acid. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Edition; Mark, H. F., Othmer, D. F., Overberger, C. G., Seaborg, G. T., Grayson, M., Eckroth, D., Eds.: John Wiley & Sons: New York, 1978; Vol. 1, pp 510-531.
9. Davis, D. D.; Kemp, D. R. Adipic acid. In Kirk-Othmer Encyclopedia of Chemical Technology; Kroschwitz, J. I., Howe-Grant, M., Eds.: John Wiley & Sons: New York, 1991; Vol. 1; pp 466-493.
10. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Why is it interesting to study cyclohexane oxidation. Synlett 1993, 10, 713-718.
11. Schuchardt, U.; Cardoso, D.; Sercheli, R.; Pereira, R.; da Cruz, R. S.; Guerreiro, M. C.; Mandelli, D.; Spinacé, E. V.; Pires, E. L. Cyclohexane oxidation continues to be a challenge. Appl. Catal., A 2001, 211, 1-17.
12. Brégault, J.-M.; Launay, F.; Atlamsani, A. Catalytic oxidative carbon-carbon bond cleavage of ketones with dioxygen: Assessment of some metal complexes. Some alternatives for preparing α,ω-dicarboxylic acids. C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 11-26.
13. (a) Musser, M. T. Adipic acid. In Ullmann's Encyclopedia of Industrial Chemistry ; Wiley-VCH Verlag: Weinheim, Germany, 2005; Vol.1, pp 537-548.
14. (b) Cornils, B.; Lappe, P. Dicarboxylic Acids, Aliphatic. In Ullmann's Encyclopedia of Industrial Chemistry ; Wiley-VCH Verlag: Weinheim, Germany, 2005; Vol. 1, pp 1-19.
15. Cavani, F.; Alini, S. Synthesis of adipic acid: On the way to more sustainable production. In Sustainable Industrial Chemistry; Cavani, F., Centi, G., Perathoner, S., Trifirò, F., Eds.: Wiley-VCH: Weinheim, Germany, 2009; pp 367-425.
16. Steinbüchel, A. Microorganisms for the preparation of polymers. Chem. Labor. Biotechnol. 1995, 46, 277-278.
17. Polen, T.; Spelberg, M.; Bott, M. Toward biotechnological production of adipic acid and precursors from biorenewables. J. Biotechnol. 2012, 167, 75-84.
18. ICIS Pricing and ICIS News ; http://www.icispricing.com/il-shared/Samples/Subpage121.asp. (http://www.icispricing.com/il-home.asp).
19. Adipic Acid 2011 World Market Outlook and Forecast; Merchant Research & Consulting, Ltd.: Birmingham, U.K., 2011.
20. Diamond, G. Production of bio-based chemicals for renewable feedstocks - An American opportunity. In Proceedings of Biomass 2011: Replace the Whole Barrel, Supply the Whole Market, National Harbor, MD, July 26, 2011 http://www.rennovia.com).
21. 2O projects under the CDM: Adipic acid - A case of carbon leakage? Stockholm Institute Working Paper WP-US-1006; Stockholm Institute: Somerville, MA, 2010.
22. Cavani, F.; Teles, J. H. Sustainability of catalytic oxidation: An alternative approach or a structural evolution? ChemSusChem 2009, 2, 508-534.
23. Berezin, I. V.; Denisov, E. T.; Emanuel, N. M. The Oxidation of Cyclohexane; Pergamon Press: Oxford, U.K., 1966.
24. Emanuel, N. M.; Denisov, E. T.; Maizus, Z. K. Liquid Phase Oxidation of Hydrocarbons; Pergamon Press: New York, 1967.
25. Tolman, C. A. Resume. Research accomplishments and interests, 1997 http://copland.udel.edu/~tolman/resume.html).
26. Rao, D. G.; Tirukkoyilur, R. S. Liquid-phase oxidation of cyclohexane to adipic acid in a single stage. Ind. Eng. Chem., Prod. Res. Dev. 1986, 25, 299-304.
27. Wen, Y.; Potter, O. E.; Sridhar, T. Uncatalyzed oxidation of cyclohexane in a continuous reactor. Chem. Eng. Sci. 1997, 52, 4593-4605.
28. Alagy, J.; Trambouze, P.; Van Landergham, H. Designing a cyclohexane oxidation reactor. Ind. Eng. Chem. Process Des. Dev. 1974, 13, 317-323.
29. Kharkova, T. V.; Arest-Yakubovich, I. L.; Lipes, V. V. Kinetic model of the liquid-phase oxidation of cyclohexane: I. Homogeneous proceeding of the process. Kinet. Katal. 1989, 30, 954-958.
30. Tanaka, K. Adipic acid in one step. CHEMTECH 1974, 4, 555-559.
31. Suresh, A. K.; Sridhar, T.; Potter, O. E. Autocatalytic oxidation of cyclohexane - Modeling reactor kinetics. AIChE J. 1988, 34, 69.
32. Suresh, A. K.; Sharma, M. M.; Sridhar, T. Engineering aspects of industrial liquid phase air oxidation of hydrocarbons. Ind. Eng. Chem. Res. 2000, 39, 3958-3997.
33. Onopchenko, A.; Schulz, J. G. D. Electron transfer with aliphatic substrates. Oxidation of cyclohexane with cobalt(III) ions alone and in the presence of oxygen. J. Org. Chem. 1973, 38, 3729-3733.
34. Tanaka, K. Adipic acid. Hydrocarbon Process. 1974, 53 (Nov.), 114-120.
35. Hendry, D. G.; Gould, C. W.; Schuetzle, D.; Syz, M. G.; Mayo, F. R. Autoxidation of cyclohexane and its autoxidation products. J. Org. Chem. 1976, 41, 1-10.
36. Shen, H.-C.; Weng, H.-S. Liquid-phase oxidation of cyclohexane to dibasic acids with immobilized cobalt catalyst. Ind. Eng. Chem. Res. 1988, 27, 2254-2260.
37. Besmar, U. N.; Lyon, J. B.; Miller, F. J.; Musser, M. T. (E. I. Du Pont de Nemours & Co.). Preparation of cyclohexanone and cyclohexanol, U.S. Patent 4,720,592, 1988.
38. Spinacé, E. V.; Pastore, H. O.; Schuchardt, U. Cyclohexane oxidation catalyzed by titanium silicalite (TS-1): Overoxidation and comparison with other oxidation systems. J. Catal. 1995, 157, 631-635.
39. Kulsrestha, G. N.; Shankar, U.; Sharma, J. S.; Singh, J. One-step oxidation of cyclohexane to adipic acid. J. Chem. Technol. Biotechnol. 1991, 50, 57-65.
40. Bart, J. C. J.; Cavallaro, S. Transiting from adipic acid to bio-adipic acid. 2, Biosynthetic pathways. Ind. Eng. Chem. Res. 2015, DOI: 10.1021/ie502074d.
41. The Flixborough cyclohexane disaster: Report of court of enquiry. Her Majesty 's Stationery Office: London, 1975.
42. Mecklenburgh, J. C. Lessons from the post-enquiry discussion of Flixborough. Int. Chem. Eng. Symp. Ser. 1976, 45, 445.
43. Horn, H. J.; Holland, E. G.; Hazleton, L. W. Safety of adipic acid as compared to citric and tartaric acid. J. Agr. Food Chem. 1957, 5, 759-762.
44. Steeman, J. W. M.; Kaarsemaker, S.; Hoftijzer, P. J. Pilot plant study of the oxidation of cyclohexane with air under pressure. Chem. Eng. Sci. 1961, 14, 139-150.
45. Pohorecki, R.; Baldyga, J.; Moniuk, W.; Krzysztoforski, A.; Wojcik, Z. Liquid-phase oxidation of cyclohexane modeling and industrial scale production simulation. Chem. Eng. Sci. 1992, 47, 2559-2564.
46. Pohorecki, R.; Baldyga, J.; Moniuk, W.; Wierzchowski, P. T. Optimization of a complex industrial process. Role of process modelling. In Proceedings of the 6th Congress on Structural and Multidisciplinary Optimization, Rio de Janeiro, Brazil, May 30-June 3, 2005.
47. Ogata, Y. Organic Chemistry: A Series of Monographs ; Wasserman, H., Ed.: Academic Press: New York, 1965.
48. Döbler, C.; Mehltretter, G.; Beller, M. Atom-efficient oxidation of alkenes with molecular oxygen: Synthesis of diols. Angew. Chem., Int. Ed. 1999, 38, 3026-3028.
49. Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J. Org. Chem. 1996, 61, 8310-8311.
50. Strukul, G., Ed. Catalytic Oxidations with Hydrogen Peroxide as Oxidant ; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
51. 2. Coord. Chem. Rev. 1992, 117, 185-213.
52. Huckins, R. W.; Huckins, H. A. A new hydrogen peroxide process to lower complexity and cost. In Proceedings of the 2002 TAPPI Fall Technical Conference and Trade Fair, San Diego, CA, Sept. 8-22, 2002.
53. Huckins, H. (Princeton Advanced Technology, Inc.). Method for producing hydrogen peroxide from hydrogen and oxygen, PCT Int. Publ. No. 03/082458 A1, 2003.
54. x/t-BuOOH-induced activation of dioxygen for the oxygenation of cyclohexene. J. Mol. Catal. A: Chem. 1999, 137, 127-233.
55. Raja, R.; Thomas, J. M.; Xu, M.; Harris, K. D. M.; Greenhill- Hooper, M.; Quill, K. Highly efficient one-step conversion of cyclohexanone to adipic acid using single-site heterogeneous catalysts. Chem. Commun. 2006, 448-450.
56. Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol.1.
57. Hamilton, G. A.; Ribner, B. S.; Hellman, T. M. Mechanism of alkane oxidation by ozone. Adv. Chem. Ser. 1968, 77, 15-25.
58. Razumovkii, S. D.; Zaikov, G. E.; Mushenko, D. V.; Klimenko, V. L.; Tsyskovskii, V. K.; Yur'ev, Yu. N. (Institute of Chemical Physics USSR Academy of Sciences). Dicarboxylic acids, Br. Patent GB 1,361,749 A, 1974.
59. Einaga, H.; Futamura, S. Oxidation behaviour of cyclohexane on alumina-supported manganese oxides with ozone. Appl. Catal., B 2005, 60, 49-55.
60. Syroezhko, A. M.; Proskuryakov, V. A.; Begak, O. Yu. Mechanism of cyclohexane ozonolysis. Considering alternative pathways. Russ. J. Appl. Chem. 2002, 75, 1448-1452.
61. 2O) - Waste to value. Stud. Surf. Sci. Catal. 2000, 130, 743-748.
62. Panov, G. I.; Dubkov, K. A.; Starokon, E. V.; Parmon, V. N. Noncatalytic liquid phase oxidation of alkenes with nitrous oxide. 1. Oxidation of cyclohexene to cyclohexanone. React. Kinet. Catal. Lett. 2002, 76, 401-406.
63. Van Deyck, F.; Weiss, F.-J.; Verberckt, R.; Thomas, E.; Mangelschots, B.; Pijl, P. (BASF AG). Verfahren zur Entfernung von Distickstoffoxid aus Wasserstoff, Stickstoffmonoxid und Distickstoffoxid enthaltenden Gasen, Ger. Offenl. DE 3244370 A1, 1984.
64. Parmon, V. N.; Panov, G. I.; Uriarte, A.; Noskov, A. S. Nitrous oxide in oxidation chemistry and catalysis: Application and production. Catal. Today 2005, 100, 115-131.
65. Parshall, G. W.; Ittel, S. D.; Homogeneous Catalysis, 2nd Edition; John Wiley & Sons: New York, 1992; p 246.
66. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
67. Partenheimer, W. Methodology and scope of metal/bromide autoxidation of hydrocarbons. Catal. Today 1995, 23, 69-158.
68. Loder, D. J. (E.I. Du Pont de Nemours & Co.). Catalytic oxidation of alkyl substituted aromatic compounds, U.S. Patent 2,245,528, 1941.
69. Saffer, A.; Barker R. S. (Mid-Century Corporation). Preparation of aromatic polycarboxylic acids, U.S. Patent 2,833,816, 1958.
70. Ishimoto, S.; Nakagawa, K.; Togawa, H.; Chubachi, S. (Teijin). Adipic acid production, Germ. Offenl. DE 1935312 A, 1970;
71. U.S. Patent 3,649,685, 1972.
72. Hayashi, O., Ed. Molecular Mechanisms of Oxygen Activation; Academic Press: New York, 1974.
73. Ingelman-Sundberg, M. In Cytochrome P-450 - Structure, Mechanism and Biochemistry; de Montellano, O., Ed.: Plenum Press: New York, 1986; pp 119-160.
74. Barton, D. H. R.; Halley, F.; Ozbalik, N.; Schmilt, M.; Young, E.; Balavoine, G. Functionalisation of saturated hydrocarbons. 14. Further studies on the mechanism of Gif-type systems. J. Am. Chem. Soc. 1989, 111, 7144-7149.
75. Barton, D. H. R.; Boivin, J.; Gastiger, M.; Morzycki, J.; Hay-Motherwell, R. S.; Motherwell, W. B.; Ozbalik, N.; Schwarzentruber, K. M. Functionalization of saturated hydrocarbons. Part 4. The Gif system for selective oxidation using molecular oxygen. J. Chem. Soc., Perkin Trans. 1 (1972-1999) 1986, 6, 947-955.
76. Barton, D. H. R.; Doller, D. The selective functionalization of saturated hydrocarbons: Gif chemistry. Acc. Chem. Res. 1992, 504-512.
77. Barton, D. H. R. Gif chemistry: The present situation. Tetrahedron 1998, 54, 5805-5817.
78. Schuchardt, U.; Spinacé, E. V.; Mano, V. In Dioxygen Activation and Homogeneous Catalytic Oxidation; Simandi, L. I., Ed.: Elsevier: Amsterdam, 1991; p 41.
79. Hill, C. L.; Prosser-McCartha, C. M. Homogeneous catalysis by transition metal oxygen anion clusters. Coord. Chem. Rev. 1995, 143, 407-455.
80. Neumann, R.; Khenkin, A. M. Molecular oxygen and oxidation catalysis by phosphovanadomolybdates. Chem. Commun. 2006, 2529-2538.
81. Parton, R. F.; Peere, G. J.; Neys, P. E.; Jacobs, P. A.; Claessens, R.; Baron, G. V. Cyclohexane oxidation with tertiary-butylhydroperoxide catalysed by iron-phthalocyanines homogeneously and occluded in Y zeolite. J. Mol. Catal. A 1996, 113, 445-454.
82. Balkus, K. J.; Eissa, M.; Lavado, R. The oxidation of cyclohexane using perfluorinaed ruthenium phthalocyanines. Stud. Surf. Sci. Catal. 1995, 94, 713-719.
83. Notari, B. Microporous crystalline titanium silicalites. Adv. Catal. 1996, 41, 253-334.
84. Tatsumi, T.; Nakamura, M.; Negishi, S.; Tominaga, H. Shape selective oxidation of alkanes with H 2O2 catalyzed by titanosilicalite. J. Chem. Soc. Chem. Commun. 1990, 476-477.
85. Clerici, M. G. Oxidation of saturated hydrocarbons with hydrogen peroxide, catalyzed by titanium silicalite. Appl. Catal. 1991, 68, 249-261.
86. Vanoppen, D. L.; De Vos, D. E.; Genet, M. J.; Rouxhet, P. G.; Jacobs, P. A. Cobalt containing molecular sieves as catalysts for autoxidation of pure cyclohexane. Angew. Chem., Int. Ed. 1995, 34, 560-563.
87. Dugal, M.; Sankar, G.; Raja, R.; Thomas, J. M. Designing a heterogeneous catalyst for the production of adipic acid by aerial oxidation of cyclohexane. Angew. Chem., Int. Ed. 2000, 39, 2310-2313.
88. Raja, R.; Sankar, G.; Thomas, J. M. Designing a molecular sieve catalyst for the aerial oxidation of n-hexane of adipic acid. Angew. Chem., Int. Ed. 2000, 39, 2313-2316.
89. Pârvalescu, V. I.; Dumitriu, D.; Poncelet, G. Hydrocarbons oxidation with hydrogen peroxide over germanic faujasites catalysts. J. Mol. Catal. A: Chem. 1999, 140, 91-105.
90. Brégeault, J.-M.; Vennat, M.; Salles, L.; Piquemal, J.-Y.; Mahha, Y.; Briot, E.; Bakala, P. C.; Atlamsani, A.; Thouvenot, R. From polyoxometalates to polyoxoperoxometalates and back again; potential applications. J. Mol. Catal. A: Chem. 2006, 250, 177-189.
91. Venturello, C.; D'Aloisio, R.; Bart, J. C. J.; Ricci, M. A new peroxotungsten heteropoly anion with special oxidizing properties: Synthesis and structure of tetrahexylammonium tetra-(diperoxotungsto)phosphate(3-). J. Mol. Catal. 1985, 32, 107-110.
92. Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. Hydrogen peroxide oxidation catalyzed by heteropolyacids combined with cetyl-pyridinium chloride: Epoxidation of olefins and allylic alcohols, ketonization of alcohols and diols, and oxidative cleavage of 1,2-diols and olefins. J. Org. Chem. 1988, 53, 3587-3593.
93. Venturello, C.; Ricci, M. (Montedison S.p.A.). Process for preparing carboxylic acids from ole fins or vicinal dihydroxy compounds, Eur. Patent EP 0,122,804A1, 1984.
94. 2 catalyzed by bis-quaternary phosphonium peroxotungstates (or peroxomolybdates) under halide- and organic solvent-free conditions. J. Mol. Catal. A: Chem. 2005, 229, 13-17.
95. (a) Steinmetz, G. R.; Lafferty, N. L.; Sumner, C. E., Jr. (Eastman Kodak Company). Process for preparation of adipic acid, U.S. Patent 4,902,827, 1990.
96. (b) Steinmetz, G. R.; Lafferty, N. L.; Sumner, C. E., Jr. The cobalt/zirconium-catalyzed oxidation of cyclohexane to adipic acid. J. Mol. Catal. 1988, 49, L39
97. Raja, R.; Ratnasamy, P. Oxidation of cyclohexane over copper phthalocyanines encapsulated in zeolites. Catal. Lett. 1997, 48, 1-10.
98. Kholdeeva, O. A.; Trukhan, N. N. Mesoporous titanium silicates as catalysts for the liquid-phase selective oxidation of organic compounds. Russ. Chem. Rev. 2006, 75, 411-432.
99. Dassel, M. W.; Rostami, A. M.; Dudgeon, D. J.; DeCoster, D. C.; Vassiliou, E. (Twenty-first Century Research Corporation). Methods and devices for separating catalyst from oxidation mixtures, PCT Int. Publ. No. WO 99/42430 A1, 1999.
100. Dassel, M. W.; Rostami, A. M.; DeCoster, D. C.; Vassiliou, E. (RPC, Inc.). Methods for removing catalyst after oxidation of hydrocarbons, U.S. Patent 6,294,689 B1, 2001.
101. Langhendries, G.; De Vos, D. E.; Sels, B. F.; Vankelecom, L.; Jacobs, P. A.; Baron, G. V. Clean catalytic technology for liquid-phase hydrocarbon oxidation. Clean Prod. Process. 1998, 1, 21-29.
102. Otake, M. Emerging Japanese catalytic technologies. CHEMTECH 1995, 25, 36-41.
103. Gibson, C. A. (Union Carbide Corporation). Catalytic conversion of phenol to cyclohexanol and/or cyclohexanone, U.S. Patent 3,998,884, 1976.
104. Parton, R. F. M. J.; Tinge, J. T.; Hoeksema, B. (DSM IP Assets B.V.). Catalyzed phenol hydrogenation, PCT Int. Publ. No. WO 2011/073233 A1, 2011.
105. Dodgson, I.; Griffin, K.; Barberis, G.; Pignataro, F.; Tauszik, G. A low cost pienol to cyclohexanone process. Chem. Ind. 1989, 830-833.
106. Fisher, W. B.; VanPeppen, J. F. Cyclohexanol and cyclohexanone. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Edition; Mark, H. F., Othmer, D. F., Overberger, C. G., Seaborg, G. T., Grayson, M., Eckroth, D., Eds.; John Wiley & Sons: New York, 1979; Vol. 7, pp 410-416.
107. Musser, M. T. Cyclohexanol and cyclohexanone. In Ullmann's Encyclopedia of Industrial Chemistry, 7th Edition; Wiley-Interscience: New York, 2007.
108. Chary, K. V. R.; Naresh, D.; Viswanathan, V.; Sadakane, M.; Ueda, W. Vapour phase hydrogenation of phenol over Pd/C catalysts: A relationship between dispersion, metal area and hydrogenation activity. Catal. Commun. 2007, 8, 471-477.
109. Mahata, M.; Viswanathan, V. Gas phase hydrogenation of phenol over supported palladium catalysts. Catal. Today 1999, 49, 65-69.
110. Joris, G. G.; Vitrone J. (Allied Chemical & Dye Corp.). Hydrogenation of phenol, U.S. Patent 2,829,166, 1958.
111. Mittag, R. Uerdinger Berichtüber die katalytischen Oxidation mit Luftsauerstoff in der Flüssigphase: 4. Oxidation von Cyclohexan. Technische Öl Mission 1941, 22.
112. Hamblet, C. H.; McAlevy, A. (E. I. Du Pont de Nemours & Co.). Adipic acid process, U.S. Patent 2,439,513, 1948.
113. Leitner, H. In Ullmann's Encyclopädie der technischen Chemie, 4th Edition; Wiley-VCH Verlag Chemie: Weinheim, Germany, 1974; Vol. 7, pp 106-115.
114. Feng, M. Preparation of adipic acid from butadiene. Hecheng Xianwei Gongye 1999, 22, 22-25.
115. Platz, R.; Kummer, R.; Schneider, H.-W.; Schwirten, K. (BASF AG). Verfahren zur Herstellung von Pent-3-ensäure und deren Alkylestern. Germ. Offenl. 2,630,086, 1978.
116. Schneider, H.-W.; Kummer, R. (BASF AG). Verfahren zur Gewinnung von Adipinsäuredimethylester, α-Methylglutarsäuredimethylester und Äthylbernsteinsäurediester aus solche enhaltenden Reaktionsgemischen, Ger. Offenl. 2,646,955, 1978.
117. Kummer, R.; Schneider, H.-W.; Taglieber, V.; Weiss, F.-J. (BASF AG). Preparation of butanedicarboxylic esters, U.S. Patent 4,310,686, 1982.
118. Kummer, R.; Schneider, H.-W.; Weiss, F.-J. (BASF AG). Manufacture of butanedicarboxylic acid esters, U.S. Patent 4,169,956, 1979.
119. Röper, M. Co-activation by homogeneous catalysts. Stud. Surf. Sci. Catal. 1991, 64, 381-429.
120. Von Kutepow, N. (BASF AG). Adipic acid from butadiene, Ger. Offenl. DE 2037782 A, 1972.
121. Bruner, H. S. (E.I. Du Pont de Nemours & Co.). Process for the manufacture of adipic acid, U.S. Patent 5,166,421, 1992.
122. Bruner, H. S., Jr.; Lane, S. L.; Murphree, B. E. (E.I. Du Pont de Nemours & Co. and DSM). Manufacture of adipic acid, U.S. Patent 5,710,325, 1998.
123. Forster, D.; Hershman, A.; Morris, D. E. Mechanistic pathways in the catalysis of olefin hydrocarboxylation by rhodium, iridium, and cobalt complexes. Catal. Rev.: Sci. Eng. 1981, 23, 89-105.
124. Process Evaluation and Research Planning Service. Sec. Quarterly Rept. 1978/79; Chemical Systems, Inc.: New York, Oct. 1978.
125. http://www.chemweek.com/sections/business-finance/europ-mideast6951.html.
126. Burke P. M. (E. I. Du Pont de Nemours & Co.). Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids, U.S. Patent 4,788,333, 1988.
127. Burke P. M. (E. I. Du Pont de Nemours & Co.). Process for the manufacture of 3-pentenoic acid, U.S. Patent 5,145,995, 1992.
128. Reppe, W.; Kroper, H.; Pistor, H. J.; Weissbarth, O. Carbonylization IV. Reaction of carbon monoxide and water with cyclic ethers. Justus Liebigs Ann. Chem. 1953, 582, 87-116.
129. Reppe, W. Neue Entwicklungen auf dem Gebiete der Chemie des Acetylens und Kohlenoxyds; Springer Verlag: Heidelberg, Germany, 1949.
130. Aliev, Ya.Yu.; Romanova, I. B. Catalytic carbonylation of organic compounds with carbon monoxide. Neftekhim., Akad. Nauk Turkm. SSR 1963, 204-213.
131. Kesling, H. S. Oxidative carbonylation. A new synthesis gas route to adipic and sebacic acids. ACS Symp. Ser. 1987, 328, 77-95.
132. Burk, M. J.; Schilling, C. H.; Burgard, A. P.; Trawick, J. D. (Genomatica, Inc.). Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol, U.S. Patent 7,803,589 A1, 2010.
133. Romani, R.; Feltri, M. (Società Rhodiatoce). Continuous process for producing adiponitrile, U.S. Patent 3,299,116, 1967.
134. (a) Drinkard, W. C.; Lindsey, R. V., Jr. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,496,215, 1970.
135. (b) Drinkard, W. C., Jr.; Kassal, R. J. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,496,217, 1970.
136. Drinkard, W. C., Jr.; Lindsey, R. V., Jr. (E. I. Du Pont de Nemours & Co.), U.S. Patent No. 3,536,748, 1970.
137. Drinkard, W. C., Jr.; Lindsey, R. V., Jr. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,538,142, 1970.
138. (e) Downing, R. G.; Fouty, R. A. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,564,040, 1971.
139. (f) Drinkard, W. C., Jr.; Lindsey, R. V. (E. I. Du Pont de Nemours&Co.), U.S. Patent 3,676,475, 1972.
140. (g) Chia, Y.-T.; Drinkard, W. C., Jr.; Squire, E. N. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,766,237, 1973.
141. (h) Drinkard, W. C., Jr. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,766,241, 1973.
142. Walter, J. W. (E. I. Du Pont de Nemours & Co.), U.S. Patent 3,773,809, 1973.
143. Tolman, C. A. Steric and electronic effects in olefin hydrocyanation at Du Pont: A scientific and industrial success story. J. Chem. Educ. 1986, 63, 199-201.
144. Bini, L.; Müller, C.; Wilting, J.; von Chrzanowski, L.; Spek, A. L.; Vogt, D. Highly selective hydrocyanation of butadiene toward 3-pentenenitrile. J. Am. Chem. Soc. 2007, 129, 12622-12623.
145. Shimizu, A. Production processes of adiponitrile. Shokubai 1998, 40, 269-273.
146. Magnussen, P.; Schumacher, V.; Gebert, W.; Reitz, H.; Praetorius, W. (BASF AG). Continuous preparation of adipic acid, U.S. Patent 4,360,695, 1982.
147. Brookhart, M.; Sabo-Etienne, S. Catalytic tail-to-tail dimerization of methyl acrylate using Rh(III) catalysts. J. Am. Chem. Soc. 1991, 113, 2777-2779.
148. Nugent, W. A.; McKinney, R. J. Linear dimerization of acrylates by palladium and rhodium catalysts: Effect of Lewis and protic acid additives. J. Mol. Catal. 1985, 29, 65-76.
149. Nugent, W. A.; Hobbs, F. W. A regiospecific, convergent route to 2,3-disubstituited cyclopentanones. J. Org. Chem. 1983, 48, 5364-5366.
150. 2COMe). J. Chem. Soc., Chem. Commun. 1989, 1850-1852.
151. 12-based catalysts for dimerization reactions of methyl acrylate and cyclotrimerization reactions of methyl propiolate. J. Mol. Catal. 1990, 59, L1-L8.
152. Nagahara, H.; Fukuoka, Y. (Asahi Chemical Industry Co., Ltd). Production of adipic acid, Jpn. Patent JP 60-239438A, 1985.
153. Gerry, R. T. In Chemical Economics Handbook; Stanford Research Institute (SRI): Menlo Park, CA, 1987.
154. Hughes, C. S. In Chemical Economics Handbook; Stanford Research Institute (SRI): Menlo Park, CA, 1987.
155. Fodor, L.; Sutradhar, B. C. (E. I. Du Pont de Nemours & Co.). Process for oxidation of cyclohexane, U.S. Patent 6,703,529, 2004.
156. Hamblet, C. H.; McAlevy, A. (E. I. Du Pont de Nemours & Co.). Adipic acid process, U.S. Patent 2,557,282, 1951.
157. Sampson, O. A. (E. I. Du Pont de Nemours & Co.). Preparation of dicarboxylic acids by nitric acid oxidation, U.S. Patent 3,359,308, 1967.
158. Castellan, A.; Bart, J. C. J.; Cavallaro, S. Nitric acid reaction of cyclohexanol to adipic acid. Catal. Today 1991, 9, 255-283.
159. Castellan, A.; Bart, J. C. J.; Cavallaro, S. Synthesis of adipic acid via the nitric acid oxidation of cyclohexanol in a two-step batch process. Catal. Today 1991, 9, 285-299.
160. Castellan, A.; Bart, J. C. J.; Cavallaro, S. Synthesis of adipic acid via nitric acid oxidation of cyclohexanol in a two-step continuous process. Catal. Today 1991, 9, 301-322.
161. Kennedy, G. L., Jr. Toxicity of adipic acid. Drug Chem. Toxicol. 2002, 25, 191-202.
162. Lewis, R. J. Carcinogenically Active Chemicals ; Van Nostrand Reinhold: New York, 1991; pp 68-69.
163. Krzysztoforski, A.; Balcerzak, K.; Ciborowski, S.; Gucwa, A. J.; Janitz, G. J. ; Kasznia, A.; Maciejczyk, S.; Maciejczyk, H.; Pochwalski, M.; Pohorecki, R.; Rygiel, S.; Schimmelpfenning, Z.; Szparski, J.; Uszynski, A.; Wais, J.; Lubiewa-Wielezynski, W.; Wójcikz; Vieweger, T. Z. M. (Zakłady Azotowe). Verfahren zur Oxydation von Cyclohexan in flüssiger Phase, Ger. Offenl. DE 3733782 A1, 1989.
164. Duynstee, E. F. J.; Hennekens, T. L. J. P. On the origin of the byproducts in the autoxidation of cyclohexane to cyclohexanol and cyclohexanone. Recl. Trav. Chim. Pays-Bas 1970, 89, 769-780.
165. Carrà, S.; Santacesaria, E. Engineering aspects of gas-liquid catalytic reactions. Catal. Rev. Sci. Eng. 1980, 22, 75-140.
166. Rapoport, M.; White, J. O. (E.I. Du Pont de Nemours & Co.). Process for the oxidation of cyclohexane, U.S. Patent 3,957,876, 1976.
167. Barnette, W. J.; Schmitt, D. L.; White, J. O. (E. L. Du Pont de Nemours & Co.). Cyclohexane oxidation in the presence of binary catalysts, U.S. Patent 3,987,100, 1976.
168. Lyon, J. B.; Stowe, G. T. (E. I. Du Pont de Nemours & Co.). Production of cyclohexyl hydroperoxide, U.S. Patent 4,675,450, 1987.
169. Russell, J. L. (Halcon International, Inc.). Process for preparation of borate esters, U.S. Patent 3,665,028, 1972.
170. Russell, J. L. (Halcon International, Inc.). Cyclohexane oxidation, U.S. Patent 3,932,513, 1976.
171. Winnick, C. N.; Teaneck, N. J. (Halcon International, Inc.). Oxidation of hydrocarbons to borate esters, U.S. Patent 3,243,449, 1966.
172. Bashkirov, A. N.; Kamzolkin, V. V.; Sokova, K. M.; Andreeva, T. P. Mechanism of liquid phase oxidation of paraffin hydrocarbons. Dokl. Akad. Nauk SSSR 1958, 118, 149-152.
173. Randal, G.; New, A.; Carrs, B.; Gardner, C.; Jubb, A. H. (ICI). Improvements in the production of adipic acid, Br. Patent 972,656, 1964.
174. Ciborowski, S. Hydroperoxides in hydrocarbons liquid-phase oxidation. In Dioxygen activation and homogeneous catalytic oxidation; Studies in Surface Science and Catalysis Series, Vol. 66; Simandi, L., Ed.: Elsevier: Amsterdam, 1991.
175. Alagy, J.; Asselineau, L.; Busson, C.; Cha, B.; Sandler, H. Selectively oxidize cyclohexane. Hydrocarbon Process. 1968, 47, 131-135.
176. Loder, D. J. (E. I. Du Pont de Nemours & Co.). Production of cyclic alcohols and ketones, U.S. Patent 2,223,494, 1940.
177. Zamaraev, K. New possibilities of NMR in mechanistic studies of homogeneous and heterogeneous catalysis. J. Mol. Catal. 1993, 82, 275-324.
178. 2Ni-substituted Keggin-type heteropolyanion. J. Mol. Catal. A: Chem. 1997, 117, 159-168.
179. 6- for oxygenation of cyclohexane with 1 atm molecular oxygen. Chem. Commun. 2000, 381-382.
180. 6-, including radical-chain mechanism. Chem. Lett. 1998, 12, 1263-1264.
181. Bonchio, M.; Carraro, M.; Scorrano, G.; Kortz, U. Microwaveassisted fast cyclohexane oxygenation catalyzed by iron-substituted polyoxotungstates. Adv. Synth. Catal. 2005, 347, 1909-1912.
182. Mizuno, N.; Nozaki, C.; Kiyoto, I.; Misono, M. Highly efficient utilization of hydrogen peroxide for selective oxygenation of alkanes catalyzed by diiron-substituted peroxometalate precursor. J. Am. Chem. Soc. 1998, 120, 9267-9272.
183. 11-. Angew. Chem., Int. Ed. 1995, 34, 1587-1589.
184. Murahashi, S. I.; Komiya, N.; Hayashi, Y.; Kumano, T. Copper complexes for catalytic, aerobic oxidation of hydrocarbons. Pure Appl. Chem. 2001, 73, 311-314.
185. Komiya, N.; Naota, T.; Oda, Y.; Murahashi, S.-I. Aerobic oxidation of alkanes and alkenes in the presence of aldehydes catalyzed by copper salts and copper-crown ether. J. Mol. Catal. A: Chem. 1997, 117, 21-37.
186. Silvia, A. C.; Lopez Fernández, T.; Carvalho, N. M. F.; Herbst, M. M.; Bordinhão, J.; Horn, A.; Wardell, J. L.; Oestreicher, E. G.; Antunes, O. A. C. Oxidation of cyclohexane catalyzed by bis-(2-pyridyl) amine Cu(II) complexes. Appl. Catal., A 2007, 317, 154-160.
187. Arends, I. W. C. E.; Sheldon, R. A.; Wallau, M.; Schuchardt, U. Oxidation transformations of organic compounds mediated by redox molecular sieves. Angew. Chem., Int. Ed. 1997, 36, 1144-1163.
188. Wang, H.-L.; Li, R.; Zheng, Y.-F.; Chen, H.-N.; Jin, J.; Wang, F.- S.; Ma, J.-T. Bismuth-containing SBA-15 mesoporous silica catalysts for solvent-free liquid-phase oxidation of cyclohexane by molecular oxygen. Helv. Chim. Acta 2007, 90, 1837.
189. Sankar, G.; Raja, R.; Thomas, J. M. Redox solid catalysts for the selective oxidation of cyclohexane in air. Catal. Lett. 1998, 55, 15-23.
190. Zhao, R.; Wang, Y.; Guo, Y.; Guo, Y.; Liu, X.; Zhang, Z.; Wang, Y.; Zhan, W.; Lu, G. A novel Ce/AlPO-5 catalyst for solvent-free liquidphase oxidation of cyclohexane by oxygen. Green Chem. 2006, 8, 459-466.
191. Yuan, H.-X.; Xia, Y.-H.; Zhan, H.-J.; Lu, X.-H.; Su, K.-X. Catalytic oxidation of cyclohexane to cyclohexanone and cyclohexanol by oxygen in a solvent-free system over metal-containing ZSM-5 catalysts. Appl. Catal., A 2006, 304, 178-184.
192. Kesavan, V.; Sivanand, P. S.; Chandrasekaran, S.; Koltypin, Y.; Gedanken, A. Catalytic aerobic oxidation of cycloalkanes with nanostructured amorphous metals and alloys. Angew. Chem., Int. Ed. 1999, 38, 3521-3523.
193. Berezin, I. V.; Kazanskaya, N. F. Sequence in the formation of the products in the liquid-phase oxidation of cyclohexane in a steel vessel. Dokl. Akad. Nauk SSSR 1959, 126, 594-597.
194. Brunner, E.; Grosskinsky, O.-A.; Herrmann, G.; Krokoszinski, R.; Magnussen, P. (BASF AG). Continuous preparation of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone by saturation of cyclohexane with oxygen and reaction in a tubular reactor, Ger. Patent DE 3403410 A1, 1985.
195. Wen, Y.; Potter, O. E.; Sridhar, T. Uncatalyzed oxidation of cyclohexane in a continuous reactor. Chem. Eng. Sci. 1997, 52, 4593-4605.
196. Ciborowski, S.; Zimowski, A. (Zakłady Azotowe w Tarnowie-Moscicachi, S.A.). Catalytic oxidation of cyclohexane, Pol. Patent PL 168,539B1, 1996.
197. (a) Pires, E. L.; Wallau, M.; Schuchardt, U. Selective oxidation of cyclohexane over rare earth exchanged zeolite Y. Stud. Surf. Sci. Catal. 1997, 110, 1025-1027.
198. (b) Pires, E. L.; Wallau, M.; Schuchardt, U. J. Mol. Catal. A: Chem. 1998, 136, 69-74.
199. Costantini, M.; Crenne, N.; Jouffret, M.; Nouvel, J. (Rhône-Poulenc S.A.). Preparation of cycloalkanones and cycloalkanols, U.S. Patent 3,923,895, 1975.
200. Brunie, J.-C.; Crenne, N. (Rhône-Poulenc S.A.). Process for the preparation of mixtures of cycloalkanols and cycloalkanones, U.S. Patent 3,927,105, 1975.
201. Tolman, C. A.; Druliner, J. D.; Krusic, P. J.; Nappa, M. J.; Seidel, W. C.; Williams, I. D.; Ittel, S. D. Catalytic conversion of cyclohexyl hydroperoxide to cyclohexanone and cyclohexanol. J. Mol. Catal. 1988, 48, 129-148.
202. Baur, H. A. C.; Kragten, U. F. (Stamicarbon B.V.). Process for preparing a cycloalkanone and/or cycloalkanol, Eur. Patent EP 0,367,326 A1, 1989.
203. Chen, J. D.; Dakka, J.; Sheldon, R. L. Selective decomposition of cyclohexyl hydroperoxide to cyclohexanone catalyzed by chromium aluminophosphate-5. Appl. Catal. 1994, 108, L1-L6.
204. Reimer, R. A. (E. I. Du Pont de Nemours & Co.). High rate process for preparation of cyclohexanol and cyclohexanone, U.S. Patent 5,206,441, 1993.
205. Oczkowicz, S.; Rygiel, S.; Wais, J.; Kozioł, A.; Gruszka, M.; Kondrat, A.; Pohorecki, R.; Wierzchowski, P.; Moniuk, W.; Krzystoforski, A.; Mijał, W.; Wójcik, W.; Zyliński, M. (Zakłady Azotowe w Tarnowie-Moscicachi, S.A.). Method for production of cyclohexanol and cyclohexanone, Pol. Patent PL 358,357 A1, 2003.
206. Balcerzak, I.; Ciborowski, S.; Szarlik, S.; Pochwalski, M.; Uszynski, A.; Rygiel, S.; Wais, J.; Gucwa, A. J. (Zakłady Azotowe w Tarnowie-Moscicachi, S.A.). Method for selective preparation of cyclohexanone and cyclohexanol by oxidation of cyclohexane, Pol. Patent PL 152,389 B1, 1990.
207. Oczkowicz, S. (Zakłady Azotowe w Tarnowie-Moscicachi, S.A.). Cyclohexane oxidation reactor, PCT Int. Publ. WO 2005/077526 A1, 2005 and references therein.
208. Holleman, A. F.; van der Laan, F. H.; Slijper, H. J. Preparation of cyclohexanol, cyclohexanone, and derivatives. Recl. Trav. Chim. Pays-Bas 1905, 24, 19-24.
209. Ellingboe, E. K. (E. I. Du Pont de Nemours & Co.). Oxidation of cyclohexane, U.S. Patent 2,228,261, 1941.
210. Cavanaugh, R. M.; Nagle, W. M. (E. I. Du Pont de Nemours & Co.). Preparation of adipic acid, U.S. Patent 2,343,534, 1944.
211. Cavanaugh, R. M. (E. I. Du Pont de Nemours & Co.). Oxidation of ketones, U.S. Patent 2,291,211, 1942.
212. Ohashi, K.; Mizutani, K. Synthesis of intermediates for nylon. I. Synthesis of adipic acid. J. Soc. Chem. Ind. Jpn. 1991, 44, 840-844.
213. Parshall, G. W. Industrial applications of homogeneous catalysis. A review. J. Mol. Catal. 1978, 4, 243-270.
214. Lindsay Smith, J. R.; Richards, D. I.; Thomas, C. B.; Whittaker, M. The role of vanadium (V) in the oxidation of cyclohexanol to adipic acid by nitric acid. J. Chem. Soc., Perkin Trans. 2 1985, 1677-1682.
215. Castellan, A. Procedimento per la produzione di acido adipico mediante ossidazione nitrico del cicloesanolo e a cicloesanone in due stadi, Ital. Pat. Appl. 41003A/86, 1986.
216. 2 emissions for products of the organic chemical industry. Energy 2003, 28, 721-740.
217. Thiemens, M. H.; Trogler, W. C. Nylon production: An unknown source of atmospheric nitrous oxide. Science 1991, 251, 932-934.
218. Intergovernmental Panel on Climate Change (IPCC). IPCC Guidelines for National Greenhouse Gas Inventories, Prepared by the National Greenhouse Gas Inventories Programme; Eggleston, H. S., Buendia, L., Miwa, K., Ngara, T., Tanabe, K., Eds.: Institute for Global Environmental Strategies (IGES): Kanagawa, Japan, 2006.
219. 2O emissions in the adipic acid industry. Chemosphere Global Change Sci. 2000, 2, 425-434.
220. 2O): The dominant ozone-depleting substance emitted in the 21st century. Science 2009, 326, 123-125.
221. Trogler, W. C. Physical properties and mechanisms of formation of atmospheric nitrous oxide. Coord. Chem. Rev. 1999, 187, 303-327.
222. Zeng, H. C.; Pang, X. Y. Catalytic decomposition of nitrous oxide on alumina-supported ruthenium catalysts Ru/Al2O3. Appl. Catal., B 1997, 13, 113-122.
223. Ovchinnikova, E. V.; Chumachenko, V. A.; Piryutko, L. V.; Kharitonov, A. S.; Noskov, A. S. Mitigation of nitrogen oxide gases in adipic acid production. Two-stage catalytic purification technology. Katal. Promyshl. 2009, 47-56.
224. 2O-decomposition from adipic acid plant. Appl. Catal., B 2007, 70, 323-329.
225. 2O, U.S. Patent 7,951,742, 2011.
226. 2O emission from adipic acid and nitric acid. In Good Practice Guidelines and Uncertainty Management in National Greenhouse Gas Inventories; IPCC Plenary (16th) Montréal, 2010; pp 183-195.
227. Enviromental Protection Agency (EPA). Executive summary of the inventory of U.S. greenhouse gas emissions and sinks: 1990-2009; EPA: Washington, DC, 2011; Document No. 403S11001.
228. Panov, G. I.; Sheveleva, G. A.; Kharitonov, A. S.; Romannikov, V. N.; Vostrikova, L. A. Oxidation of benzene to phenol by nitrous oxide over Fe-ZMS-5 zeolites. Appl. Catal., A 1992, 82, 31-36.
229. Häfele, M.; Reitzmann, A.; Roppelt, D.; Emig, G. Hydroxylation of benzene with nitrous oxide on H-Ga-ZMS5 zeolite. Appl. Catal., A 1997, 150, 153-164.
230. Sobolev, V. I.; Rodkin, M. A.; Uriarte, A. K.; Panov, G. I. Process for making phenol or phenol derivatives, U.S. Patent 6,156,938, 2000.
231. Suzuki, E.; Nakashiro, K.; Ono, Y. Hydroxylation of benzene with dinitrogen monoxide over H-ZMS5 zeolite. Chem. Lett. 1988, 953-956.
232. Loder, D. J. (E. I. Du Pont de Nemours & Co.). Oxidation of cyclic compounds, U.S. Patent 2,223,493, 1940.
233. Scientific Design Co. Production of adipic acid, Br. Patent 941,662, 1963.
234. Halcon International, Inc. Process for oxidation of cyclohexane and for the production of adipic acid, Br. Patent 956,779/80, 1964.
235. Barker, R. S.; Cohen, M. A. (Halcon International, Inc.). Adipic acid production by the two-step oxidation of cyclohexane with oxygen, U.S. Patent 2,234,271, 1966.
236. Atlamsani, A.; Brégeault, J.-M.; Ziyad, M. Oxidation of 2-methylcyclohexanone and cyclohexanone by dioxygen catalyzed by vanadium-containing heteropolyanions. J. Org. Chem. 1993, 58, 5663-5655.
237. Shimizu, A.; Tanaka, K.; Ogawa, H.; Matsuoka, Y.; Fujimori, M.; Nagamori, Y.; Hamachi, H.; Kimura, K. An industrial process for adipic acid production by the liquid-phase oxidation of cyclohexanone with molecular oxygen. Bull. Chem. Soc. Jpn. 2003, 76, 1993-2001.
238. Shilov, A. E.; Shul'pin, G. B. Activation of C-H bonds by metal complexes. Chem. Rev. 1997, 97, 2879-2932.
239. Davis, D. D. (E. I. Du Pont de Nemours & Co.). Process for the preparation of dicarboxylic acids, U.S. Patent 3,306,932, 1967.
240. Doumani, T. F.; Coe, C. S.; Attané, E. C., Jr. (Union Oil Company of California). Production of cycloalkylnitrites, U.S. Patent 2,465,984, 1949.
241. Markownikoff, W. B. Derivatives of the naphthene or cyclohexane series. II. Justus Liebigs Ann. Chem. 1898, 302, 1-42.
242. (a) Nametkin, S. S. Action of nitric acid on saturated hydrocarbons. J. Russ. Phys. Chem. Soc. 1908, 40, 1570.
243. (b) Nametkin, S. S. Ber. Dtsch. Chem. Ges. 1909, 42, 1372-1377.
244. Aschan, O. Formation of adipic acid from the 80 °C boiling fraction of Russian petroleum. Ber. Dtsch. Chem. Ges. 1899, 32, 1769-1772.
245. Muzart, J. Chromium-catalyzed oxidation in organic synthesis. Chem. Rev. 1992, 92, 113-140.
246. Pillai, U. R.; Sahle-Demessie, E. A highly efficient oxidation of cyclohexane over VPO catalysts using hydrogen peroxide. Chem. Commun. 2002, 2142-2143.
247. II system in the oxidation of cyclohexane with hydrogen peroxide under an inert atmosphere. New J. Chem. 1991, 15, 955.
248. Shul'pin, G. B.; Süss-Fink, G.; Lindsay-Smith, J. R. Oxidation of the system Hydrogen peroxide-Manganese (IV) complex-acetic acid. Part II. Tetrahedron 1999, 55, 5345-5358.
249. Kirillov, A. M.; Kopylovich, M. N.; Kirillova, M. V.; Karabach, E. Yu.; Haukka, M.; Guedes da Silva, M. F. C.; Pombeiro, A. J. L. Mild peroxidative oxidation of cyclohexane catalyzed by mono-, di-, tri-, tetraand polynucleo copper triethanolamine complexes. Adv. Synth. Catal. 2006, 348, 159-174.
250. 2 in air. Tetrahedron Lett. 1996, 37, 6487-6490.
251. Carvalho, W. A.; Wallau, M.; Schuchardt, U. Iron and copper immobilised on mesoporous MCM-41 molecular sieves as catalysts for the oxidation of cyclohexane. J. Mol. Catal. A: Chem. 1999, 144, 91-99.
252. 2 oxidation and epoxidation of hydrocarbons and alcohols over titanium aluminophosphates TAPO-5, TAPO-11, and TAPO-36. J. Catal. 1998, 177, 231-239.
253. Carvalho, W. A.; Varaldo, P. B.; Wallau, M.; Schuchardt, U. Mesoporous redox molecular sieves analogous to MCM-41. Zeolites 1997, 18, 408-416.
254. Raja, R.; Sankar, G.; Thomas, J. M. Powerful redox molecular sieve catalysts for the selective oxidation of cyclohexane in air. J. Am. Chem. Soc. 1999, 121, 11926-11927.
255. Corma, A.; Camblor, M. A.; Esteve, P.; Martínez, A.; Pérez-Pariente, J. Activity of Ti-Beta catalyst for the selective oxidation of alkenes and alkanes. J. Catal. 1994, 145, 151-158.
256. Notari, B. Synthesis and catalytic properties of titaniumcontaining zeolites. Stud. Surf. Sci. Catal. 1988, 37, 413-425.
257. Maldotti, A.; Bartocci, C.; Amadelli, R.; Polo, E.; Battioni, P.; Mansuy, D. Oxidation of alkanes by dioxygen catalysed by photoactivated iron porphyrins. J. Chem. Soc., Chem. Commun. 1991, 1487-1489.
258. Hari, P. R.; Rao, P.; Ramaswamy, A. V. Oxyfunctionalization of alkanes with hydrogen peroxide catalyzed by vanadium silicates. J. Chem. Soc., Chem. Commun. 1992, 1245-1246.
259. Sakthivel, A.; Selvan, P. Mesoporous (Cr) MCM-41: A mild and efficient heterogeneous catalyst for selective oxidation of cyclohexane. J. Catal. 2002, 211, 134-143.
260. Ziolek, M. Catalytic liquid-phase in heterogeneous system as green chemistry goal - Advantages and disadvantages of MCM-41 used as catalyst. Catal. Today 2004, 90, 145-150.
261. Huybrechts, D. R. C.; Buskens, P. L.; Mathijs, G. M. K.; Martens, L. R. M. (Exxon Chemical). Catalysts and their use in oxidation of saturated hydrocarbons, U.S. Patent 5,739,076, 1998.
262. Mizuno, N.; Kiyoto, I.; Nozaki, C.; Misono, M. Remarkable structure dependence of intrisic catalytic activity for selective oxidation of hydrocarbons with hydrogen peroxide catalysed by iron substituted silicotungstates. J. Catal. 1999, 181, 171-174.
263. Simões, M. M. Q.; Conceic¸ão, C. M. M.; Gamelas, J. A. F.; Domingues, P. M. D. N.; Cavaleiro, A. M. V.; Cavaleiro, J. A. S.; Ferrer-Correia, A. J. V.; Johnstone, R. A. W. Keggin-type peroxotungstates as catalysts in the oxidation of cyclohexane by dilute aqueous hydrogen peroxide. J. Mol. Catal. A: Chem. 1999, 144, 461-468.
264. (9+x)- (x = predominantly 1) and oxidation catalysis by the catalyst precursor. J. Mol. Catal. 1994, 88, L125-L131.
265. Luna, F. J.; Ukawa, S. E.; Wallau, M.; Schuchardt, U. Cyclohexane oxidation using transition metal-containing aluminophosphates (MAPO-VFI). J. Mol. Catal. A: Chem. 1997, 117, 405-411.
266. Thomas, J. M.; Raja, R.; Sankar, G.; Bell, R. G.; Lewis, D. W. Benign by design. New catalysts for an environmentally conscious age. Pure Appl. Chem. 2001, 73, 1087-1101.
267. Thomas, J. M.; Raja, R.; Sankar, G.; Johnson, B. F. G.; Lewis, D. W. Solvent-free routes to clean technology. Chem. - Eur. J. 2011, 7, 2972-2978.
268. II) substituted "sandwich" type polyoxometalates: Preparation, characterization, and catalytic activity in oxidations of alkanes and alkenes by peroxides. Inorg. Chem. 1995, 34, 5753-5760.
269. Murahashi, S.-I.; Oda, Y.; Naota, T.; Kuwabara, T. Ruthenium catalyzed cytochrome P-450 type oxidation of alkanes with alkyl hydroperoxides. Tetrahedron Lett. 1993, 34, 1299-1302.
270. Murahashi, S.-I; Oda, Y.; Komiya, N.; Naota, T. Ruthenium catalyzed oxidation of alkanes with peracids. Tetrahedron Lett. 1994, 35, 7453-7456.
271. Thomas, J. M.; Raya, R. Innovations in oxidation catalysis leading to a sustainable society. Catal. Today 2006, 117, 22-31.
272. Miller, S. A. Cyclohexane, cyclohexanol, and cyclohexanone. Chem. Process Eng. (London) 1969, 50, 63-72.
273. Nakano, T.; Ishii, Y. (Daicel Chemical Industries). Oxidation catalytic system and oxidation process, Eur. Patent Appl. EP 0,858,835 A1, 1998.
274. Vassiliou, E.; Dassel, M. W.; Rostami, A. M.; Dudgeon, D. J.; DeCoster, D. C. (Twenty-first Century Research Corporation). Process for treating cobalt catalyst in oxidation mixtures of hydrocarbons to dibasic acids, PCT Int. Publ. WO 99/40058A1, 1999.
275. Vassiliou, E.; Dassel, M. W.; Aldrich, S. M.; Rostami, A. M.; DeCoster, D. C. (RPC, Inc.). Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent-tohydrocarbons ratio, U.S. Patent 6,037,491, 2000.
276. Costantini, M.; Fache, E. (Rhodia Fiber and Resin Intermediates). Hydrocarbons, alcohol and/or ketone oxidation method, PCT Int. Publ. WO 2000/059858, 2000.
277. Costantini, M.; Fache, E. (Rhodia Fiber and Resin Intermediates). Co/Cr catalyzed oxidation of cyclohexane, U.S. Patent 6,147,256, 2000.
278. Tanaka, K.; Shimizu, A. (Asahi Chemical Corp.). Methods for producing adipic acid, Jpn. Patent JP2001/253845A, 2001.
279. Bonnet, D.; Amoros, D.; Simonato, J.-P.; Augier, F.; Broglio, M.-I. (Rhodia Polyamide Intermediates). Methods for making carboxylic acids, PCT Int. Publ. WO 2004/041768 A1, 2004.
280. Onopchenko, A.; Schulz, J. G. D. (Gulf Research & Development Co.). Process for converting cyclohexane to adipic acid, U.S. Patent 4,032,569, 1997.
281. Kollar, J. (Gulf Research & Development Co.). Preparation of dibasic acids, U.S. Patent 3,231,608, 1966.
282. DeCoster, D. C.; Vassiliou, E.; Dassel, M. W.; Aldrich, S. M.; Rostami, A. M. (RPC, Inc.). Methods and devices for controlling the reaction rate and/or reactivity of hydrocarbon to an intermediate oxidation product by adjusting the oxidant consumption rate, U.S. Patent 6,288,274 B1, 2001.
283. Schulz, J. G. D.; Onopchenko, A. (Gulf Research & Development Co.). Process for converting cyclohexane to adipic acid, U.S. Patent 4,263,453, 1981.
284. Park, C.-M.; Goroff, N. S. (Amoco Corp.). One-step air oxidation of cyclohexane to produce adipic acid, U.S. Patent 5,221,800, 1993.
285. Kulsrestha, G. N.; Saxena, M. P.; Gupta, A. K.; Goyal, H. B.; Prasad, R.; Prasada Rao, T. S. R. (Council of Scientific & Industrial Research). Catalyst and a process for preparing carboxylic acids using the catalyst, U.S. Patent 5,547,905, 1996.
286. Kollar, J. (BASF). A process for the preparation of adipic acid and other aliphatic dibasic acids, PCT Int. Publ. WO94/07833, 1994.
287. Kollar, J. (Redox Technologies, Inc.). Process for the preparation of adipic acid and other aliphatic dibasic acids, U.S. Patent 5,321,157, 1994.
288. 3 route over Co/Mn cluster complexes. J. Catal. 2002, 212, 39-45.
289. Rostami, A. M.; DeCoster, D. C.; Vassiliou, E.; Dassel, M. W.; Aldrich, S.M. (RPC, Inc.). Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio, Can. Patent CA 2,297,740 A1, 1999.
290. Aldrich, S. M.; DeCoster, D. C.; Vassiliou, E.; Dassel, M. W.; Rostami, A. M. (RPC, Inc.). Methods and devices for oxidizing a hydrocarbon to form an acid, U.S. Patent 6,359,173 B1, 2002.
291. 2. Org. Process Res. Dev. 1998, 2, 255-260.
292. Barton, D. H. R.; Li, T.; MacKinnon, J. Synergistic oxidation of cyclohexane and hydrogen sulfide under Gif conditions. Chem. Commun. 1997, 557-558.
293. n (n = 2 or 3). J. Org. Chem. 1996, 61, 4520-4526.
294. Lin, S.-S.; Weng, H.-S. Liquid-phase oxidation of cyclohexane over CoAPO-5: Synergism effect of coreactant and solvent effect. Appl. Catal., A 1994, 118, 21-31.
295. Kraushaar-Czarnetzki, B.; Hoogervorst, W. G. M.; Stork, W. H. J. Oxidation of saturated hydrocarbons involving CoAPO molecular sieves as oxidants and as catalysts. Stud. Surf. Sci. Catal. 1994, 84, 1869-1876.
296. Lin, S.-S.; Weng, H.-S. Liquid-phase oxidation of cyclohexane using CoAPO-5 as the catalyst. Appl. Catal., A 1993, 105, 289-308.
297. Thomas, J. M.; Raja, R.; Sankar, G.; Bell, R. G. Redox molecular sieve catalysts for the aerobic selective oxidation of hydrocarbons. Stud. Surf. Sci. Catal. 2000, 130, 887-892.
298. Kraushaar-Czarnetzki, B.; Hoogervorst, W. G. M. (Shell). Catalytic oxidation of hydrocarbons, Eur. Patent Appl. 0,519,569 A2, 1992.
299. Vanoppen, D. L.; Jacobs, P. A. Cobalt-containing molecular sieves as catalysts for the low conversion autoxidation of pure cyclohexane. Part II. A kinetic study. Catal. Today 1999, 49, 177-183.
300. Chen, J. D.; Dakka, J.; Neeleman, E.; Sheldon, R. A. Chromium-substituted aluminophosphate-5: A recyclable catalyst for the selective oxidation of secondary alcohols. J. Chem. Soc., Chem. Commun. 1993, 1379-1380.
301. Thomas, J. M.; Raya, R. Catalytically active centres in porous oxides: design and performance of highly selective new catalysts. Chem. Commun. 2001, 675-687.
302. Costantini, M.; Fache, E.; Laurent, G. (Rhône-Poulenc Fiber and Resin Intermediates). Method for oxidising hydrocarbons, alcohols or ketones using heterogeneous catalysts, PCT Int. Publ.WO96/31455, 1996.
303. Laha, S. C.; Gläser, R. Characterization and catalytic performance of Cr-MCM-41 and Cr-MCM-48 prepared by either classical or microwave heating. Microporous Mesoporous Mater. 2007, 99, 159-166.
304. Lü, G.; Ji, D.; Qian, G.; Qi, Y.; Wang, X.; Suo, J. Gold nanoparticles in mesoporous materials showing catalytic selective oxidation of cyclohexane using oxygen. Appl. Catal., A 2005, 280, 175-180.
305. Thibault-Starzyk, F.; Parton, R. F.; Jacobs, P. A. Oxidation of cyclohexanone and cyclohexane to adipic acid by iron-phthalocyanine on zeolite Y. Stud. Surf. Sci. Catal. 1994, 84, 1419-1424.
306. Ishii, Y.; Nakano, T. (Daicel Chemical Industries, Ltd.). Oxidation catalyst system and process for oxidation with the same, Eur. Patent EP 0,824,962 A1, 1997.
307. Yuan, Y.; Ji, H.; Chen, Y.; Han, Y.; Song, X.; She, Y.; Zhong, R. Oxidation of cyclohexane to adipic acid using Fe-porphyrin as a biomimetic catalyst. Org. Process Res. Dev. 2004, 8, 418-420.
308. Bonnet, D.; Ireland, T.; Fache, E.; Simonato, J.-P. Innovative direct synthesis of adipic acid by air oxidation of cyclohexane. Green Chem. 2006, 8, 556-559.
309. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv. Synth. Catal. 2001, 343, 393-427.
310. Daicel Chemical employs NHPI catalyst method for adipic acid. Focus Catal. 2004, 2004 (1), DOI: 10.1016/S1351-4180(04)00095-9.
311. Punta, C.; Gambarotti, C. N-hydroxy derivatives: key organocatalysts for the selective free radical aerobic oxidation of organic compounds. In Ideas in Chemistry and Molecular Sciences: Advances in Synthesis Chemistry; Pignataro, B., Ed.; Wiley-VCH Verlag: New York, 2010; pp 2-24.
312. Baucherel, X.; Sheldon, R. A. (ICI). Catalytic oxidation process, PCT Int. Publ. WO 02/100810 A1, 2002.
313. Baucherel, X.; Gonsalvi, L.; Arends, I. W. C. E.; Elwood, S.; Sheldon, R. A. Aerobic oxidation of cycloalkanes, alcohols and ethylbenzene catalysed by the novel carbon radical chain promoter NHS (N-hydroxysaccharin). Adv. Synth. Catal. 2004, 346, 286-296.
314. Sawatari, N.; Yokota, T.; Sakagushi, S.; Ishii, Y. Alkane oxidation with air catalyzed by lipophilic N-hydroxyphthalimides without any solvent. J. Org. Chem. 2001, 66, 7889-7891.
315. Yang, G.; Zhang, Q.; Miao, H.; Tong, X.; Xu, J. Selective organocatalytic oxygenation of hydrocarbons by dioxygen using anthraquinones and N-hydroxyphthalimide. Org. Lett. 2005, 7, 263-266.
316. Tong, X.; Xu, J.; Miao, H. Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system. Adv. Synth. Catal. 2005, 347, 1953-1957.
317. 2. Chem. Lett. 1997, 10, 1045-1046.
318. Srinivas, P.; Mukhopadhyay, M. Oxidation of cyclohexane in supercritical carbon dioxide medium. Ind. Eng. Chem. Res. 1994, 33, 3118-3124.
319. Srinivas, P.; Mukhopadhyay, M. Influence of thermodynamic state on cyclohexane oxidation kinetics in carbon dioxide medium. Ind. Eng. Chem. Res. 1997, 36, 2066-2074.
320. 2 and in liquid solvents over Mn-APO-5 molecular sieve. Green Chem. 2002, 4, 426-430.
321. Armbruster, U.; Martin, A. Partial oxidation of cyclohexane in supercritical carbon dioxide.DGMK Tagungsber. 2002-2004, 273-276.
322. Beckman, E. J. Oxidative reactions in CO2: Academic exercise or future green processes. Environm. Sci. Technol. 2003, 37, 5289-5296.
323. Ingelman-Sundberg, M. In Cytochrome P-540 - Structure, Mechanism and Biochemistry; De Montellano, O., Ed.; Plenum Press: New York, 1986; pp 119-160.
324. Murahashi, S.-I.; Komiya, N. New types of catalytic oxidations in organic synthesis. Catal. Today 1998, 41, 339-349.
325. Sheldon, R. A., Ed. Metalloporphyrins in Catalytic Oxidation; Marcel Dekker: New York, 1994.
326. Montanari, F.; Casella, L. Metalloporphyrins in Catalytic Oxidation; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994; pp 87-120.
327. Mansuy, D. Biomimetic catalysts for selective oxidation in organic chemistry. Pure Appl. Chem. 1990, 62, 741-746.
328. Groves, J. T.; Nemo, T. E.; Myers, R. S. Hydroxylation and epoxidation catalyzed by iron-porphine complexes, Oxygen transfer from iodosylbenzene. J. Am. Chem. Soc. 1979, 101, 1032-1033.
329. Cook, B. R.; Reinert, T. J.; Suslick, K. S. Shape selective alkane hydroxylation using metalloporphyrin catalysts. J. Am. Chem. Soc. 1986, 108, 7281-7286.
330. Battioni, P.; Renaud, J.-P.; Bartoli, J. F.; Mansuy, D. Hydroxylation of alkanes by hydrogen peroxide: An efficient system using manganese porphyrins and imidazole as catalyst. J. Chem. Soc., Chem. Commun. 1986, 341-343.
331. Murahashi, S.-I.; Naota, T.; Komiya, N. Metalloporphyrin catalyzed oxidation of alkanes in molecular oxygen in the presence of acetaldehyde. Tetrahedron Lett. 1995, 36, 8059-8062.
332. Ratnasamy, P.; Raja, R. A process for the preparation of adipic acid, Eur. Patent EP 97/0,784,045 A1, 1997.
333. Raja, R.; Thomas, J. M. Catalyst design strategies for controlling reactions in microporous and mesoporous molecular sieves. J. Mol. Catal. A: Chem. 2002, 181, 3-14.
334. Nakamura, M.; Tatsumi, T.; Tominaga, H.-O. Synthesis and catalytic capability of zeolite-encapsulated iron and manganese tetramethylporphine complexes. Bull. Chem. Soc. Jpn. 1990, 63, 3334-3336.
335. Herron, N.; Stucky, G. D.; Tolman, C. A. Shape selectivity in hydrocarbon oxidations using zeolite encapsulated iron phthalocyanine catalysts. J. Chem. Soc., Chem. Commun. 1986, 1521-1522.
336. 2+-perfluorophthalocyanine incorporated inside Y faujasite and mesoporous MCM-41 as heterogeneous catalysts for the oxidation of cyclohexane. Appl. Catal., A 1999, 181, 305-312.
337. Langhendries, G.; Baron, G. V.; Neys, P. E.; Jacobs, P. A. Liquidphase hydrocarbon oxidation using supported transition metal catalysts: Influence of the solid support. Chem. Eng. Sci. 1999, 54, 3563-3568.
338. Barton, D. H. R.; Bévìre, S. D.; Hill, D. R. The functionalization of saturated hydrocarbons. Part XXIX. Application of tert-butyl hydroperoxide and dioxygen using soluble Fe(III) and Cu(II) chelates. Tetrahedron 1994, 50, 2665-2670.
339. Schuchardt, U.; Pereira, R.; Rufo, M. Iron(III) and copper(II) catalysed cyclohexane oxidation by molecular oxygen in the presence of tert-butyl hydroperoxide. J. Mol. Catal. A: Chem. 1998, 135, 257-262.
340. Klein, S.; Martens, J. A.; Parton, R.; Vercruysse, K.; Jacobs, P. A.; Maier, W. F. Amorphous microporous mixed oxides as selective redox catalysts. Catal. Lett. 1996, 38, 209-214.
341. Klein, S.; Thorimbert, S.; Maier, W. F. Amorphous microporous titania-silica mixed oxides: preparation, characterization, and catalytic redox properties. J. Catal. 1996, 163, 476-488.
342. 2 over chromium aluminophosphate-5 molecular sieves. J. Catal. 1995, 153, 1-8.
343. Thomas, J. M.; Raja, R.; Sankar, G.; Bell, R. G. Molecular-sieve catalysts for the selective oxidation of linear alkanes by molecular oxygen. Nature 1999, 398, 227-230.
344. Usui, Y.; Sato, K. A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide. Green Chem. 2003, 5, 373-375.
345. Gonzalez, M. A.; Howell, S. G.; Sikdar, S. K. Photocatalytic selective oxidation of hydrocarbons in the aqueous phase. J. Catal. 1999, 183, 159-162.
346. Frei, H.; Blatter, F.; Sun, H. Photocatalyzed oxidation of hydrocarbons in zeolite cages. CHEMTECH 1996, 26, 24-30.
347. (a) Nekhaev, A. I.; Zaikin, V. G.; Bagrii, E. I. Photoinitiated liquid-phase oxidation of saturated hydrocarbons by oxygen or air. Neftekhimiya 1998, 38, 22-26.
348. (b) Nekhaev, A. I.; Zaikin, V. G.; Bagrii, E. I. Chem. Abstr. 1998, 129, 95187.
349. 2 in a zeolite under visible light with complete selectivity. J. Am. Chem. Soc. 1996, 118, 6873-6879.
350. Sheldon, R. A.; Van Santen, R. A., Eds.; Catalytic Oxidation Principles and Applications; World Scientific Publishing: Singapore, 1995.
351. Herron, N. The selective partial oxidation of alkanes using zeolite based catalysts. A completely inorganic cytochrome P450 mimic. New J. Chem. 1989, 13, 761-766.
352. 2 over VS-2. Res. Chem. Intermed. 1998, 24 (5), 529-541.
353. Tolman, C. A.; Druliner, J. D.; Nappa, M. J.; Herron, N. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; John Wiley & Sons, Ltd.: Chichester, U.K., 1989; pp 303-360.
354. Herron, N.; Tolman, C. A. A highly selective zeolite catalyst for hydrocarbon oxidation. A completely inorganic mimic of the alkane ω-hydroxylases. J. Am. Chem. Soc. 1987, 109, 2837-2839.
355. Modén, B.; Zhan, B.-Z.; Dakka, J.; Santiesteban, J. G.; Iglesia, E. Reactant selectivity and regiospecificity in the catalytic oxidation of alkanes on metal-substituted aluminophosphates. J. Phys. Chem. C 2007, C111, 1402-1411.
356. Thomas, J. M.; Raja, R.; Sankar, G.; Bell, R. G. Molecular-sieve catalysts for the regioselective and shape selective oxyfunctionalization of alkanes in air. Acc. Chem. Res. 2001, 34, 191-200.
357. Zhan, B.-Z.; Modén, B.; Dakka, J.; Santiesteban, J. G.; Iglesia, E. Catalytic oxidation of n-hexane on Mn-exchanged zeolites: Turnover rates, regioselectivity, and spatial constraints. J. Catal. 2007, 245, 316-325.
358. Nagahara, H.; Ono, M.; Konishi, M.; Fukuoka, Y. Partial hydrogenation of benzene to cyclohexene. Appl. Surf. Sci. 1997, 121, 448-451.
359. Nagahara, H.; Konishi, M. (Asahi Chemical Industry Co., Ltd.). Production of cyclolefin, Jpn. Patent 62-45541 A, 1985.
360. Yamashita, K.; Obana, H.; Katsuta, I. (Asahi Kasei Kogyo K.K.). Method for partially hydrogenating a monocyclic aromatic hydrocarbon, Eur. Patent EP 0,552,809 A1, 1993.
361. Hu, S.-C.; Chen, Y.-W. Partial hydrogenation of benzene: A review. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396.
362. 2 over peroxytungstate organic complex catalysts. Green Chem. 1999, 1, 275-276.
363. Blach, P.; Böstrom, Z.; Franceschi-Messant, S.; Lattes, A.; Perez, E.; Rico-Lattes, I. Recyclable process for sustainable adipic acid production in microemulsions. Tetrahedron 2010, 66, 7124-7128.
364. Li, H.; Zhu, W.; He, X.; Zhang, Q.; Pan, J.; Yan, Y. Oxodiperoxo tungsten complex-catalyzed synthesis of adipic acid with hydrogen peroxide. React. Kinet. Catal. Lett. 2007, 92, 319-327.
365. Ren, S.; Chie, Z.; Cao, L.; Xie, X.; Qin, G.; Wang, J. Clean synthesis of adipic acid catalyzed by complexes derived from heteropoly acid and glycine. Catal. Commun. 2009, 10, 464-467.
366. Sato, K.; Aoki, M.; Noyori, R. A. A "green" route to adipic acid. Direct oxidation of cyclohexenes with 30% hydrogen peroxide. Science 1998, 281, 1646-1647.
367. Antonelli, E.; D'Aloisio, R.; Gambaro, M.; Fiorani, T.; Venturello, C. Efficient oxidative cleavage of olefins to carboxylic acids with hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis-(oxodiperoxotungsto)phosphate(3-) under two-phase conditions. Synthetic aspects and investigation of the reaction course. J. Org. Chem. 1998, 63, 7190-7206.
368. Bonsignore, S.; Soncino, P. (Enichem S.p.A./Eniricerche S.p.A.). Tungsten- or molybdenum-based supported compositions, process for obtaining them and use thereof as heterogeneous catalysts, Eur. Patent EP 0,593,129 A1, 1997.
369. 2 in the presence of a TAPO-5 catalyst. Angew. Chem., Int. Ed. 2003, 42, 1520-1523.
370. 2: A comparative study of catalytic activity and stability. Appl. Catal., A 2008, 345, 195-200.
371. Venturello, C.; D'Aloisio, R. Quaternary ammonium tetrakis-(diperoxotungsto)phosphates(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide. J. Org. Chem. 1988, 53, 1553-1557.
372. 3-. J. Am. Chem. Soc. 1995, 117, 681-691.
373. Bailey, A. J.; Griffith, W. P.; Parkin, B. C. Heteropolyperoxo- and isopolyperoxo-tungstates and -molybdates as catalysts for the oxidation of tertiary amines, alkenes and alcohols. J. Chem. Soc., Dalton Trans. 1995, 1833-1837.
374. Noyori, R.; Aoki, M.; Sato, K. Green oxidation with aqueous hydrogen peroxide. Chem. Commun. 2003, 1977-1988.
375. Reed, S. M.; Hutchison, J. E. Green chemistry in the organic teaching laboratory: An environmentally benign synthesis of adipic acid. J. Chem. Educ. 2000, 77, 1627.
376. Raston, C. L.; Scott, J. L. Teaching green chemistry. Third-year-level module and beyond. Pure Appl. Chem. 2001, 73, 1257-1260.
377. Ito, S.; Iwamoto, T. Introduction of environmental-friendly chemical reaction experiments to chemistry students in the science department of Tohoku University specific for adipic acid. Kagaku to Kyoiku (Chemistry and Education) 2002, 50, 433-436.
378. Zhu, W.; Li, H.; He, X.; Zhang, Q.; Shu, H.; Yan, Y. Synthesis of adipic acid catalyzed by surfactant-type peroxotungstates and peroxomolybdates. Catal. Commun. 2008, 9, 551-555.
379. 2 oxidation of organic substrates. Aust. J. Chem. 2002, 53, 69-74.
380. Knops-Gerrits, P. P.; Thibault-Starzyk, F.; Jacobs, P. A. Adipic acid synthesis via oxidation of cyclohexene over zeolite occluded manganese diimine complexes. Stud. Surf. Sci. Catal. 1994, 84, 1411-1418.
381. Lapisardi, G.; Chiker, F.; Launay, F.; Nogier, J.-P.; Bonardet, J.-L. A "one-pot" synthesis of adipic acid from cyclohexene under mild conditions with new bifunctional Ti-AlSBA mesostructured catalysts. Catal. Commun. 2004, 5, 277-281.
382. Kholdeeva, O. A.; Derevyankin, A.Yu.; Shmakov, A. N.; Trukhan, N. N.; Paukshtis, E. A.; Tuel, A.; Romannikov, V. N. Alkene and thioether oxidations of H2O2 over Ti-containing mesoporous mesophase catalysts. J. Mol. Catal. A 2000, 158, 417-421.
383. Blasco, T.; Corma, A.; Navarro, M. T.; Pérez-Pariente, J. Synthesis, characterization, and catalytic activity of Ti-MCM-41 structures. J. Catal. 1995, 156, 65-74.
384. Besson, M.; Bonnet, M. C.; Gallezot, P.; Tkatchenko, I.; Tuel, A. Catalysis for fine chemicals: towards specificity with polyphasic media. Catal. Today 1999, 51, 547-560.
385. 2 and t-butyl hydroperoxide. Catal. Lett. 1998, 50, 107-114.
386. 2 catalyzed by titanium-containing mesoporous molecular sieves. Chem. Commun. 1998, 325-326.
387. Lapisardi, G.; Chiker, F.; Nogier, J. P.; Bonardet, J. L. Preparation, characterisation and catalytic activity of new bifunctional Ti-AlSBA-15 materials. Application to a "one-pot" green synthesis of adipic acid from cyclohexene and organic hydroperoxides. Microporous Mesoporous Mater. 2005, 78, 289-295.
388. Cheng, C.-Y.; Lin, K.-J.; Prasad, M. R.; Fu, S.-J.; Chang, S.-Y.; Shyu, S.-G.; Sheu, H.-S.; Chen, C.-H.; Chuang, C.-H.; Lin, M.-T. Synthesis of a reusable oxotungsten-containing SBA-15 mesoporous catalysts for the organic solvent-free conversion of cyclohexene to adipic acid. Catal. Commun. 2007, 8, 1060-1064.
389. 2. Catal. Lett. 2002, 81, 131-136.
390. Trukhan, N. N.; Romannikov, V. N.; Paukshtis, E. A.; Shmakov, A. N.; Kholdeeva, O. A. Oxidation of 2,3,6-trimethylphenol over Ti- and V-containing mesoporous mesophase catalysts: structure-activity/ selectivity. J. Catal. 2001, 202, 110-117.
391. Wilhoit, E. D. (E. I. Du Pont de Nemours & Co.). Process for the preparation of dicarboxylic acid, U.S. Patent 5,236,561, 1993.
392. Haas, G. R.; Kolis, J. W. Oxidation of alkenes in supercritical carbon dioxide catalyzed by molybdenum hexacarbonyl. Organometallics 1998, 17, 4454-4460.
393. Krishna, R. R.; Chawla, H. P. S.; Dev, S. Chromic acid oxidation of some oxiranes. Indian J. Chem. 1984, 23B, 1190-1196.
394. Tojo, M.; Fukuoka, Y. (Asahi Kasei Kogyo K.K.). Process for producing cyclic alcohol, U.S. Patent 4,661,639, 1987.
395. Kozhevnikov, I. V.; Matveev, K. I. Homogeneous catalysts based on heteropoly acids (review). Appl. Catal. 1983, 5, 135-150.
396. Antonetti, C.; Raspolli Galletti, A. M.; Accorinti, P.; Alini, S.; Babini, P.; Raabova, K.; Rozhko, E.; Caldarelli, A.; Righi, P.; Cavani, F.; Concepcion, P. Two alternative routes for 1,2-cyclohexanediol synthesis by means of green processes: cyclohexene dihydroxylation and catechol hydrogenation. Appl. Catal., A 2013, 466, 21-31.
397. Usui, Y.; Sato, K.; Tanaka, M. Catalytic dihydroxylation of olefins with hydrogen peroxide: An organic solvent- and metal-free system. Angew. Chem., Int. Ed. 2003, 42, 5623-5625.
398. Cavani, F.; Raabova, K.; Rozhko, E.; Righi, P.; Alini, S.; Accorinti, P.; Babini, P. Two-step process for a sustainable production of adipic acid from cyclohexene. Prepr. - Am. Chem. Soc., Div. Pet. Chem. 2012, 57, 261-262.
399. Cavani, F. Catalytic selective oxidation faces the sustainability challenge; turning points, objectives reached, old approaches revisited and solutions still requiring investigation. J. Chem. Technol. Biotechnol. 2010, 85, 1175-1183.
400. Schindler, G.-P.; Bartl, P.; Hoelderich, W. F. Oxidative cleavage of cyclohexane derivatives over titanium-containing Y zeolites. Appl. Catal., A 1998, 166, 267-279.
401. Chen, H.; Dai, W.-L.; Gao, R.; Cao, Y.; Li, H.; Fan, K. New green manufacture of glutaric acid from the oxidation of cyclopentane-1,2-diol with aqueous hydrogen peroxide. Appl. Catal., A 2007, 328, 226-236.
402. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. A direct conversion of vic-diols into 1,2-diketones with aqueous hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP). Tetrahedron Lett. 1995, 36, 1523-1526.
403. Venturello, C.; Ricci, M. Oxidation cleavage of 1,2-diols to carboxylic acids by hydrogen peroxide. J. Org. Chem. 1986, 51, 1599-1602.
404. 2 catalyzed by heteropolyacids. J. Mol. Catal. A: Chem. 1996, 114, 217-220.
405. Rozhko, E.; Raabova, K.; Macchia, F.; Malmusi, A.; Righi, P.; Accorinti, P.; Alini, S.; Babini, P.; Cerrato, G.; Manzoli, M.; Cavani, F. Oxidation of 1,2-cyclohexanediol to adipic acid: A study into selectivity-affecting parameters. ChemCatChem 2013, 5, 1998-2008.
406. Felthouse, T. R.; Fraundorf, P. B.; Friedman, R. M.; Schosser, C. L. Expanded lattice ruthenium pyrochlore oxide catalysts. J. Catal. 1991, 127, 393-420.
407. Brégeault, J.-M. Transition-metal complexes for liquid-phase catalytic oxidation: Aspects of industrial reactions and of emerging technologies. J. Chem. Soc., Dalton Trans. 2003, 3289-3302.
408. Lissel, M.; Dehmlow, E. V. Oxidative Spaltung von Ketonen mit Kaliumsuperoxide. Anwendungen der Phasentransfer-katalyse 8. Tetrahedron Lett. 1978, 19, 3689-3690.
409. Spinacé, E. V.; Pastore, H. O.; Schuchardt, U. Cyclohexane oxidation catalyzed by titanium silicate (TS-1): Overoxidation and comparison with other oxidation systems. J. Catal. 1995, 157, 631-635.
410. Lee, J.; Wang, C. C. Dehydrogenate cyclohexanol. Hydrocarbon Process. 1992, 71, 67-68.
411. Béziat, J.; Besson, M.; Gallezot, P. Liquid phase oxidation of cyclohexanol to adipic acid with molecular oxygen on metal catalysts. Appl. Catal., A 1996, 135, L7-L11.
412. VanPeppen, J. F.; Fisher, W. B.; Chan, C. H. Phenol hydrogenation process. In Catalysis of Organic Reactions; Augustine, R. L., Ed.; Marcel Dekker: New York, 1980; pp 141-158.
413. Kim, Y.; Kim, H.; Lee, J.; Sim, K.; Han, Y.; Park, H. A modified Wacker catalysis using heteropolyacid: Interaction of heteropolyanion with Cu(II) in cyclohexene oxidation. Appl. Catal., A 1997, 155, 15-26.
414. Pestchanker, M. J.; Giordano, O. S. A novel application of the base induced mesyl elimination. Tetrahedron Lett. 1990, 31, 463-464.
415. Imre, L.; Schomäcker, R.; Daun, J. (Bayer AG). Process for the preparation of carbonyl compounds by catalytic oxidation of olefins and catalysts in microemulsion, Eur. Patent EP 0,717,025 A2, 1996.
416. Cavani, F.; Raabova, K.; Bigi, F.; Quarantelli, C. A rationale of the Baeyer-Villiger oxidation of cyclohexanone to ε-caprolactone with hydrogen peroxide: Unprecedented evidence for a radical mechanism controlling reactivity. Chem. - Eur. J. 2010, 16, 12962-12969.
417. Ishii, Y.; Adachi, A.; Imai, R.; Ogawa, M. Hydrogen peroxide oxidation of cyclohexanone and cyclohexanone peroxide in the presence of metal oxides. Chem. Lett. 1978, 611-614.
418. Ghiron, A. F.; Thompson, R. C. Kinetic study of the oxygentransfer reactions from the oxo diperoxo complexes of molybdenum-(VI) and tungsten(VI) to (thiolato)- and (sulfenato)cobalt(III) complexes. Inorg. Chem. 1988, 27, 4766-4771.
419. Vennat, M.; Herson, P.; Brégeault, J.-M.; Shul'pin, G. B. Vanadium-catalyzed aerobic cleavage of C-C bonds in substituted cyclohexanones to afford carboxylic acids: Two model complexes with tetrahedral geometry around vanadium(V). Eur. J. Inorg. Chem. 2003, 908-917.
420. El Aakel, L.; Launay, F.; Atlamsani, A.; Brégeault, J.-M. Efficient and selective catalytic oxidative cleavage of α-hydroxy ketones using vanadium-based HPA and dioxygen. Chem. Commun. 2001, 2218-2219.
421. El Aakel, L.; Launay, F.; Brégeault, J.-M.; Atlamsani, A. Nafion-supported vanadium oxidation catalysts: redox versus acid-catalysed ring opening of 2-substituted cycloalkanones by dioxygen. J. Mol. Catal. A.: Chem. 2004, 212, 171-182.
422. Crezee, E.; Barendregt, A.; Kapteijn, F.; Moulijn, J. A. Carbon coated monolithic catalysts in the selective oxidation of cyclohexanone. Catal. Today 2001, 69, 283-290.
423. Costantini, M.; Krumenacker, L. (Rhône-Poulenc Chimie de Base). Procédé de préparation d'acide adipique, Fr. Patent 2,541,993, 1983.
424. Fumagalli, C.; Minisci, F.; Pirola, R. (Lonza S.p.A.). Process for the production of carboxylic acids, PCT Int. Publ. WO 01/87,815 A2, 2001.
425. Brégeault, J.-M.; Bassam, E. A.; Martin, J. (Rhône-Poulenc Chimie). Preparation of aliphatic carboxylic acids by oxidation of monocyclic ketones, U.S. Patent 4,983,767, 1991.
426. Kusonoki, M.; Ogawa, M. (Showa Denko K.K.). Dibasic acids from oxidation of cyclohexanone, Jpn. Tokkyo Koho JP 44,005,858, 1969.
427. Kamath, S. S.; Chandalia, S. B. Liquid-phase oxidation of cyclohexanone to adipic acid by air in acetic acid solution. J. Appl. Chem. Biotechnol. 1973, 23, 469-478.
428. Khenkin, A. M.; Neumann, R. Low temperature activation of dioxygen and hydrocarbon oxidation catalyzed by a phosphovanadomolybdate: Evidence for a Mars-van Krevelen type mechanism in a homogeneous liquid phase. Angew. Chem., Int. Ed. 2000, 39, 4088-4090.
429. 40, catalysed oxidation of aromatic and alkyl aromatic compounds: Evidence for aerobic Mars-van Krevelen-type reaction in the liquid homogeneous phase. J. Am. Chem. Soc. 2001, 123, 8531-8542.
430. Cavani, F.; Ferroni, L.; Frattini, A.; Lucarelli, C.; Mazzini, A.; Raabova, K.; Alini, S.; Accorinti, P.; Babini, P. Evidence for the presence of alternative mechanisms in the oxidation of cyclohexanone to adipic acid with oxygen, catalyzed by Keggin polyoxometalates. Appl. Catal., A 2011, 391, 118-124.
431. Besson, M.; Blackburn, A.; Gallezot, P.; Kozynchenko, O.; Pigamo, A.; Tennison, S. Oxidation with air of cyclohexanone to carboxylic diacids on carbon catalysts. Top. Catal. 2000, 13, 253-257.
432. Besson, M.; Gauthard, F.; Horvath, B.; Gallezot, P. Catalytic oxidation with air of cyclohexanone to dicarboxylic acids on synthetic carbons. Effect of supported metals and solvents. J. Phys. Chem. B 2005, B109, 2461-2467.
433. Shen, H.-C.; Weng, H.-S. The liquid-phase oxidation of cyclohexanone to dibasic acids with immobilized cobalt catalyst. Ind. Eng. Chem. Res. 1988, 27, 2246-2253.
434. Shen, H.-C.; Weng, H.-S. Liquid-phase oxidation of cyclohexanone over cerium oxide catalyst. Ind. Eng. Chem. Res. 1990, 29, 713-719.
435. Draths, K. M.; Frost, J. W. Environmentally compatible synthesis of adipic acid from D-glucose. J. Am. Chem. Soc. 1994, 116, 399-400.
436. Niu, W.; Draths, K. M.; Frost, J. W. Benzene-free synthesis of adipic acid. Biotechnol. Prog. 2002, 18, 201-211.
437. Thomas, J. M.; Raja, R.; Johnson, B. F.; O'Connell, T. J.; Sankar, G.; Khimyak, T. Bimetallic nanocatalysts for the conversion of muconic acid to adipic acid. Chem. Commun. 2003, 1126-1127.
438. Launay, F.; Roucoux, A.; Patin, H. Ruthenium colloids: A new catalyst for alkane oxidation by t-HBP in a biphasic water-organic phase system. Tetrahedron Lett. 1998, 39, 1353-1356.
439. Venturello, C.; Alneri, E.; Ricci, M. A new, effective catalytic system for epoxidation of olefins by hydrogen peroxide under phase transfer conditions. J. Org. Chem. 1983, 48, 3831-3833.
440. Jiang, H.; Gong, H.; Yang, Z. H.; Zhang, X. T.; Sun, Z. L. Clean synthesis of adipic acid by direct oxidation of cyclohexene in the absence of phase transfer agents. React. Kinet. Catal. Lett. 2002, 75, 315-321.
441. Lambert, A.; Plucinshi, P.; Kozhevnikov, I. V. Polyoxometalatecatalyzed epoxidation of 1-octene with hydrogen peroxide in microemulsions coupled with ultrafiltration. Chem. Commun. 2003, 714-715.
442. Kaur, J.; Kozhevnikov, I. V. Polyoxometalate-catalysed epoxidation of propylene with hydrogen peroxide: Microemulsion versus biphasic process. Catal. Commun. 2004, 5, 709-713.
443. Neumann, R.; Khenkin, A. M. Peroxometalate catalyzed oxidations with hydrogen peroxide in biphasic reaction media: Reactions in inverse emulsions. J. Org. Chem. 1994, 59, 7577-7579.
444. Holmberg, K. Organic reactions in microemulsions. Curr. Opin. Colloid Interface Sci. 2003, 8, 187-196.