Production of chemicals from cellulose and biomass-derived compounds: Advances in the oxidative functionalization of levulinic acid

ACS Symposium Series

Volumn 954, Issue , 2007, Pages 262-279

  Saladino, R ^a   Pagliaccia, T ^a   Argyropoulos, D S ^b   Crestini, C ^c  

^a UNIVERSITY OF TUSCIA   (Italy)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36749103109     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2007-0954.ch017     Document Type: Conference Paper

References (86)

1. F.W. Lichtenthaler (Ed.), Carbohydrates as Organic Raw Materials, VCH Publ., Weinheim/ New York, 1991.
2. G. Descotes (Ed.), Carbohydrates as Organic Raw Materials II, VCH Publ., Weinheim/New York, 1993.
3. Van Bekkum, H.; Roper, H.; Voragen, A.G.J. (Eds.), Carbohydrates as Organic Raw Materials III, VCH Publ., Weinheim/New York, 1996.
4. Eierdanz, H. (Ed.), Perspektiven nachwachsender Rohstofe in der Chemie, VCH Publ., Weinheim New York, 1996.
5. Lichtenthaler, F.W.; Mondel, S. Perspectives in the use of low molecular weight carbohydrates as organic raw material. Pure Appl. Chem., 1997, 69, pp 1853-1866.
6. Hugill, A. Introductory Dedicational Metaphor, in Sugar and all That. A History of Tate and Lyle, Gentry Books, London, 1978.
7. For some representative examples of pyrolysis of lignocellulosic materials see: (a) Shafizadeh, F.; Chin, P.P.S. Pyrolytic production and decomposition of 1,6-anhydro 3,4-dideoxy-β-Dglycero-hex-3-enopyranos-2- ulose. Carbohydr. Res. 1976, 46, pp 149-154.
8. (b) Shafizadeh, F.; Ward, D.D.; Pang, D. Michael addition reaction of levoglucosenone, Carbohydr. Res. 1982, 102, pp 217-230.
9. For some representative examples of production of low molecular weight chemicals from cellulose and cellulose wastes see: (a) Seri, K.; Sakaki, T.; Shibata, M.; Inoue, Y.; Ishida, H. Lanthanum(III)-catalyzed degradation of cellulose at 250°C. Bioresource Technology 2002, 81, pp 257-260, and references cited therein.
10. (b) Sheldon, R.A.; Kochi, J.K. Metal Catalyzed Oxidation of Organic Compounds, Academic Press, New York, NY 1981.
11. (c) Shafizadeh, F.; Chin, P. S.Preparation of 1,6-anhydro-3,4-dideoxy-D- glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereof. Carbohydr. Res. 1977, 58, p 79.
12. For some example of patent claim the production of levulinic acid from cellulose and biomass-derived compounds see: (a) Taraban'ko, V. E.; Shambazov, V.K.; Kuznetsova, S.A.; Kuznetsov, B.N. Processing of wood from small-leaf trees in production of vanillin and syringyl aldehyde and levulinic acid. Russ. (2003). Application: RU 2002-124176 20020911.
13. (b) Taraban'ko, V.E.; Kozlov, I.A.; Pervyshina, E.P.; Chernyak, M.Yu.; Kuznetsov, B.N. Chemical method of processing conifer wood by catalytic oxidation and acid hydrolysis yielding vanillin, levulinic acid and hydroxymethylfurfural. Russ. (2000). Application: RU 99-124884 19991125.
14. (c) Taraban'ko, V.E.; Pervyshina, E.P.; Kuznetsov, B.N. Manufacture of vanillin and syringaldehyde by catalytic oxidation of smallleaved wood species with oxygen in alkaline medium and extraction of levulinic acid from the residue. Russ. (1998). Application: RU 97-101245 19970124.
15. (d) Asahi Chemical Industry Co.,Ltd., Japan, Levulinic acid and esters. Jpn. Kokai Tokkyo Koho (1982), 7 pp., Application: JP 80-79672 19800613.
16. For some recent examples of patent claim the production of important industrial compounds from levulinic acid see: (a) Ochneva, V. A.; Trostyanetskaya, V. L.; Alenkin, A.V.; Silaeva, N.A.; Shapovalova, T.A.; Tudorovskii, E.L. Method for preparing 4,4′-azobis-(4-cyanopentanoic acid) as a radical polymerization initiator, Russ. (2004). Application: RU 2002-131371 20021122.
17. (b) Shibuya, N.; Sato, A. Preparation of 4,4′-azobis-4-cyanovaleric acid. Jpn. Kokai Tokkyo Koho (1998), 4 pp. Application: JP 97-32994 19970131.
18. (c) Narutomi, T.; Okamura, K.; Minami, S. Continuous manufacture of 5-aminolevulinic acid with methane-forming bacteria, (1994) 5 pp. Application: JP 92-33222619921119.
19. (d) Natsuume, T.; Ueda, T. Stabilized ferrous compound composition. U.S. (1987), 8 pp. Application: US 85-807245 19851210.
20. For some examples of studies on the formation of levulinic acid see: (a) Horvat, J.; Klaic, B.; Metelko, B.; Sunjic, V. Tetrahedron Lett. 1985, 26, 2111.
21. (b) Horvat, J.; Klaic, B.; Metelko, B.; Sunjic V. Croat. Chem. Acta1986, 59, p 429.
22. Fugalli S. La Chimica e L'Industria 2004, 86, pp 6-59.
23. (a) Fitzpatrick, S.W. Production of levulinic acid from carbohydrates-containing materials, Biofine Incorporated US patent 5,608,105, 1997.
24. (b) Fitzpatrick, S. W. Lignocellulose degradation to furfural and levulinic acid, Biofine Incorporated US patent 4,897,497, 1990.
25. For some recent examples of patent claim the production of important industrial compounds from levulinic acid see: (a) Ochneva, V.A.; Trostyanetskaya, V.L.; Alenkin, A. V.; Silaeva, N.A.; Shapovalova, T.A.; Tudorovskii, E. L. Method for preparing 4,4′-azobis-(4-cyanopentanoic acid) as a radical polymerization initiator, Russ. (2004). Application: RU 2002-131371 20021122.
26. (b) Shibuya, N.; Sato, A. Preparation of 4,4′-azobis-4-cyanovaleric acid. Jpn. Kokai Tokkyo Koho (1998), 4 pp. Application: JP 97-32994 19970131.
27. (c) Narutomi, T.; Okamura, K.; Minami, S. Continuous manufacture of 5-aminolevulinic acid with methane-forming bacteria, (1994) 5 pp. Application: JP 92-332226 19921119.
28. (d) Natsuume, T.; Ueda, T. Stabilized ferrous compound composition. U.S. (1987), 8 pp. Application: US 85-807245 19851210.
29. Timokhin, B.V.; Baransky, V.A.; Eliseeva, G.D. Levulinic acid in organic synthesis. Russian Chemical Reviews 1999, 68, pp 73-84.
30. Cubbon, R. C. P.; Hewlett, C. Organic peroxides containing functional groups. Ill Reaction of hydrogen peroxide and tert-butyl hydroperoxide with 4-oxovaleric acid. J. Chem. Soc. C: Organic 1968, p 2986.
31. (a) Cannon, G.; Garst, J.E. Preparation and Baeyer-Villiger reaction of certain 2-carbalkoxycyclopropyl methyl ketones. Pharm. Sci. 1975, 64, p 1059.
32. (b) Hamprecht, G.; Ruchardt, C. Tert-alkylperoxy-γ-lactones and 3-(tert-alkylperoxy)phthalides. Tetrahedron Lett. 1968, 28, p 3195.
33. Jpn. Patent 4513; Ref. Zh. Khim. 16N 34P 1964.
34. Gubelt, G.; Warkentin, J. Oxidation with lead tetraacetate. IV. Cyclization of phenylhydrazones of levulinic acid, levulinanilide, 5-ketohexanoic acid, 4-keto-1-pentanol, and of levulinic acid oxime. Canadian Journal of Chemistry 1969, 47(21), pp 3983-7.
35. For some representative examples see: (a) Cai, N.-C.; Wang, Y.-P.; Wang, E-F.; Peng, Z.-H. Degradation of levulinic acid in the new photodegradation reaction system. Wuhan Daxue Xuebao, Ziran Kexueban 1999, 45(6), pp 814-816.
36. (b) Venkateswarlu, K. Ch.; Rao, M.A. Kinetics and mechanism of oxidation of 4-oxopentanoic acid by cerium(IV) in acid medium. Acta Ciencia Indica, Chemistry 1996, 22(4), pp 135-139.
37. (c) Arora, S.D.; Prakash, A.; Mehrotra, R.N. Kinetics and mechanism of oxidations by metal ions. Part 16. Oxidation of 4-oxopentanoic acid by aquomanganese(III) ions. Transition Metal Chemistry 1993, 18(4), pp 401-5.
38. (d) Mehrotra, R.N. Kinetics and mechanisms of oxidations by metal ions. V. Oxidation of 4-oxopentanoic acid by the aquavanadium(V) ion. Bulletin of the Chemical Society of Japan 1985, 58(8), pp 2389-94.
39. (e) Joshi, U.R.; Limaye, P.A. Syntheses of biochemicals and industrial chemicals from levulinic acid .III. Application of Kolbe electroorganic process to derivatives of levulinic acid. Journal of the University of Poona, Science and Technology 1981,54, pp 67-77.
40. (f) Singh, B.; Singh, B.B.; Singh, S. Kinetics and mechanism of alkaline hexacyanoferrate(III) oxidation of levulinic acid. Journal of the Indian Chemical Society 1980, 57(6), pp 662-3.
41. Smith, S.; Dunlop, A.P. Preparation of succinic acid US Patent 2,676,186; Ref. Zh. Khim. 16N 34P 1955.
42. Panwar, K.S.; Gaur, Jifendra N. Photo-induced oxidation of some organic carbonyl compounds by vanadium(V). Talanta 1967, 14(1), pp 127-9.
43. (a) Singh, B.; Sahai, S. Mechanism of ruthenium(III) catalysis in oxidation of levulinic acid by N-bromoacetamide in perchloric acid. J. Indian Chemical Society 1991, 68, pp 208-209.
44. (b) Pandey, S.K.; Yadav, S.P.S.; Prasad, M.; Prasad, J. Mechanism of Ru(III) catalysis in oxidation of levulinic acid by acidic solution of N-bromobenzamide. Asian J. Chemistry 1999, 11, pp 203-206.
45. Beattie, I.R.; Jones, P.J. Methyltrioxorhenium. An air-stable compound containing a carbon-rhenium bond. Inorg. Chem. 1979, 18, p 2318.
46. Romão C.C.; Kühn, F.E.; Herrmann W.A. Rhenium(VII) oxo and imido complexes: synthesis, structures, and applications Chem. Rev. 1997, 97, pp 3197-3246.
47. Herrmann W.A.; Fischer, R.W.; Marz, D.W. Methyltrioxorhenium as catalyst for olefin oxidation Angew. Chem., Int. Ed. Engl. 1991, 30, p 1638.
48. Herrmann W. A.; Fischer, R. W.; Marz, D. W. Methyltrioxorhenium as catalyst for olefin oxidation Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
49. Zhu, Z.; Espenson, J.H. Oxidation of alkynes by hydrogen peroxide catalysed by methylrhenium trioxide J. Org. Chem. 1995, 60, p 7728.
50. (a) Saladino, R.; Fiani, C.; Belfiore, M.C.; Gualandi, G.; Penna, S.; Mosesso, P. Methyltrioxorhenium catalysed synthesis of highly oxidised aryltetralin lignans with anti-topoisomerase II and apoptogenic activities Bioorg. Med. Chem. 2005, 13, pp 5949-5960.
51. (b) Crestini, C.; Pro, P.; Neri, V.; Saladino, R. Methyltrioxorhenium: A new catalyst for the activation of hydrogen peroxide to the oxidation of lignin and lignin model compounds" Bioorg. Med Chem. 2005, 13, pp 2569-2578
52. 2 J. Chem. Soc., Perkin Trans 1 2000, pp 581-586.
53. Brown, K.N.; Espenson, J.H. Stepwise oxidation of thiophene and its derivatives by hydrogen peroxide catalysed by methyltrioxorhenium(VII) Inorg. Chem. 1996, 35, p 7211.
54. Kunkely, H.; Vogler, A. Photoreactivity of the triphenylphosphine adduct of methyl(trioxo)rhenium(VII) induced by ligand-to-metal charge transfer exitation J. Organom. Chem. 2000, 606, pp 207-209.
55. (a) Zauche, T.H.; Espenson, J.H. Kinetics and mechanism of the oxidation of secondary hydroxylamines to nitrones with hydrogen peroxide, catalysed by methylrhenium trioxide Inorg. Chem. 1997, 36, pp 5257-5261.
56. (b) Goti, A.; Nannelli, L. Synthesis of nitrones by methyltrioxorhenium catalysed direct oxidation of secondary amines Tetrahedron Lett. 1996, 37, pp 6025-6028.
57. (a) Herrmann W.A.; Fischer, R.W.; Correira, J.D.G. Multiple bonds between main-group elements and transition metals. Part 133. Methyltrioxorhenium as a catalyst of the Baeyer-Villiger oxidation J. Mol Catalysis. 1994, 94, pp 213-223.
58. 2 catalytic system Tetrahedron Letters 2001, 42/32, pp 5401-5404.
59. Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Methyltrioxorhenium- catalyzed C-H insertion reactions of hydrogen peroxide Tetrahedron Lett. 1995, 36, 6415.
60. 2 in air 1996, 37, pp 6487-6490.
61. J. Finlay, A. McKervey, H.Q.N. Gunaratne Oxidations Catalysed by Rhenium(V) Oxo Species 1. Conversion of Furans to Enediones using Methyltrioxorhenium and Urea Hydrogen Peroxide. Tetrahedron Lett. 1998, 39, pp 5651-5654.
62. Herrmann, W.A.; Fischer, R.W.; Scherer, W.; Rauch, M.U. Methyltrioxorhenium(VII) as catalyst for epoxidations: structure of the active species and mechanism of catalysis Angew. Chem., Int. Ed. Engl. 1993, 32, pp 1157-1160.
63. Herrmann, W.A.; Waguer, W.; Volkhardt, U. Organic derivatives of rhenium oxides and their preparation and use for the metathesis of olefins. US Patent 5,342,985 August 30, 1994.
64. Fischer, R. W., Herrmann, W.A.; Kratzer, R. Direct synthesis of organorhenium oxides from compounds containing rhenium US Patent 6,180,807 B1, 2001.
65. Thomas, J.M. and Thomas W.J. Principles and Practice of heterogeneous catalysis; VCH: New York, 1997.
66. Herrmann, W.A.; Fritz-Meyer-Weg, D.M.; Wagner, M.; Kuchler, J.G.; Weichselbaumer, G.; Fischer, R. Use of organorhenium compound for the oxidation of multiple C-C bonds, oxidation processes based thereon and novel organorhenium compounds U.S. Patent 5,155,247, Oct. 13, 1992.
67. Copèret, C.; Adolfsson, H.; Sharpless, K.B. A simple and efficient method for epoxidation of terminal alkenes J. Chem. Soc. Chem. Commun. 1997, p 1915.
68. Donbrow, M. in Microcapsules and Nanoparticles in Medicine and Pharmacy; CRC Press: Boca Raton, FL, 1992.
69. Saladino, R.; Neri, V.; Pelliccia, A.R.; Caminiti, R.; Sadun, C. Preparation and structural characterization of polymer-supported methylrhenium trioxide systems as efficient and selective catalysts for the epoxidation of olefins J Org. Chem. 2002, 67, pp 1323-1332.
70. 2 and polymer supported methylrhenium trioxide systems Tetrahedron 2003, 59, pp 7403-7408.
71. 2 systems for the oxidation of cardanol derivatives Pure Appl. Chem. 2003, 2, pp 261-268.
72. Saladino, R.; Neri, V.; Cardona, F.; Goti, A. Oxidation of N,N-disubstituted hydroxylamines to nitrones with hydrogen peroxide catalyzaed by polymersupported methylrhenium trioxide systems Adv. Synth. Catal., 2004, 346, pp 639-647.
73. a) Saladino, R.; Andreoni, A.; Neri, V.; Crestini, C. Tetrahedron 2005, 61, pp 1069-1075.
74. b) Saladino, R.; Neri, V.; Mincione, E.; Filippone, P. Selective oxidation of phenol and anisole derivatives to quinones with hydrogen peroxide and polymer-supported methylrhenium trioxide systems Tetrahedron 2002, 58, pp 8493-8500.
75. Bianchini, G.; Crucianelli, M.; De Angelis, F.; Neri, V.; Saladino, R. A Novel Catalyzed C-H Insertion Reactions of Hydrogen Peroxide by Poly(4-vinylpyridine)/Methyltrioxorhenium Tetrahedron Lett. 2004, 45, pp 2351-2353.
76. Bianchini, G.; Crucianelli, M.; De Angelis, F.; Neri, V.; Saladino, R. Highly efficient C-H insertion reactions of hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorhenium systems in ionic liquids Tetrahedron Lett. 2005, 46, pp 2427-2432.
77. PL Patent 87-269352 19871210, 1992.
78. Slavtcheff, S.C.; Barrow, R.S.; Kanga, D.V.; Cheney, C.M.; Znaider, A. Cosmetic composition for treatment of pimples and redness CA Patent 94-2113232, 19940111, and US Patent 5482710,19930730, 1995.
79. Jin, Y.; Kim, D.H. Synlett 1998, 11, pp 1189-1190.
80. Tanzawa, T.; Schartz, J. Catalytic conversion of hydroxy carboxylic acids to olefins by tungsten(VI) complexes: a new acyl group transfer catalyst. Organometallics 1990, 9, pp 3026-3027.
81. For examples of reviews on β-lactone derivatives see: (a) Lowe, C.; Vederas, J.C. Org. Prep. Proe. Int. 1995, 27, pp 305-346.
82. (b) Pommier, A.; Pons, J.M. Recent Advances in β-lactone Chemistry Synthesis 1995, 7, pp 729-744.
83. Ferriera, P.; Xue, W.M.; Bencze, E.; Herdtweck, E.; Kühn, F.E. J. Inorg. Chem. 2001, 40, 5834-5841, and references cited therein.
84. See for example: Takas, J.; Kiprof, P.; Riede, J.; Herrmann, W.A. Organometallics 1990, 9, pp 782-787.
85. Stankovic, S.; Espenson, J.H. J. Org. Chem. 2000, 65, pp 5528-5530.
86. Mander, L.N. ; Sethi, S.P. Tetrahedron Lett. 1984, 25, pp 5953-5956.