Catalytic upgrading of fermentation-derived organic acids

Biotechnology Progress

Volumn 15, Issue 5, 1999, Pages 845-854

  Varadarajan, Sriram ^a   Miller, Dennis J ^a  

^a Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BUTANEDIOL; BIOFUEL; CARBOXYLIC ACID; CATALYSIS; FERMENTATION; TETRAHYDROFURAN;

BIOCATALYSTS; BIOCONVERSION; BIOMASS; CATALYSIS; CHEMICAL INDUSTRY; CHEMICAL REACTIONS; CONDENSATION REACTIONS; DEHYDRATION; FEEDSTOCKS; HYDROGENATION; ORGANIC ACIDS; PETROLEUM PRODUCTS;

CATALYTIC CONVERSION; CHEMICAL PRODUCTION; LACTIC ACID; SUCCINIC ACID;

FERMENTATION;

EID: 0033198626     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp9900965     Document Type: Article

References (105)

1. Lee, J. Biological conversion of lignocellulosic biomass to ethanol. J. Biotechnol. 1997, 56, 1.
2. Grewal, H.; Kalra, K. Fungal Production of Citric Acid. Biotechnol. Adv. 1995, 13, 209.
3. Pazouki, M.; Panda, T. Recovery of citric acid - a review. Bioprocess Eng. 1998, 19, 435.
4. Milson, P. E.; Meers, J. L. Gluconic and Itaconic Acids. Comprehensive Biotechnology; Moo-Young, M., Blanch, H. W., Drew, H. W., Wang, D. I. C., Eds.; Pergamon Press: New York, 1985; Vol. 3, Chapter 35.
5. Cheryan, M.; Parekh, S.; Shah, M.; Witjitra, K. Production of acetic acid by Clostridium thermoaceticum. Adv. Appl. Microbiol. 1997, 43, 1.
6. Boyaval, P.; Corre, C. Production of propionic acid. Lait 1995, 75, 453.
7. Jin, Z. W.; Yang, S. T. Extractive fermentation for enhanced propionic acid production from lactose by Propionibacterium acidipropionici. Biotechnol. Prog. 1998, 14, 457.
8. Rehberger, J. L.; Glatz, B. A. Response of cultures of propionibacterium to acid and low pH: Tolerance and inhibition. J. Food Prot. 1998, 61, 211.
9. Vandak, D.; Zigova, J.; Sturdik, E.; Schlosser, S. Evaluation of solvent and pH for extractive fermentation of butyric acid. Process Biochem. 1997, 32, 245.
10. Hwang, S.; Hansen, C. L. Modeling and optimization in anaerobic bioconversion of complex substrates to acetic and butyric acids. Biotechnol. Bioeng. 1997, 54, 451.
11. Du, J. X.; Cao, N. J.; Gong, C. S.; Tsao, G. T.; Yuan, N. J. Fumaric acid production in airlift loop reactor with porous sparger. Appl. Biochem. Biotechnol. 1997, 63-65, 541.
12. Pouton, C. W.; Akhtar, S. Biosynthetic polyhydroxyalkanoates and their potential in drug delivery. Adv. Drug Delivery Rev. 1996, 18, 133.
13. Litchfield, J. H. Microbiological production of lactic acid. Adv. Appl. Microbiol. 1996, 42, 45.
14. Datta, R.; Tsai, S. P. Lactic acid production and potential uses: A technology and economics assessment. ACS Symp. Ser. #666 1997, 224.
15. Thayer, A. Polylactic acid is basis of Dow, Cargill venture. Chem. Eng. News (Dec. 8, 1997), 75 (49), 14.
16. Gokarn, R. R.; Eitemann, M. A.; Sridhar, J. Production of succinate by anaerobic microorganisms. ACS Symp. Ser. #666 1997, 237.
17. Nghiem, N. P.; Davison, B. H.; Suttle, B. H.; Richardson, G. R. Production of succinic acid by Anaerobiospirillum succiniciproducens. Appl. Biochem. Biotechnol. 1997, 63-65, 565.
18. Holten, C. H. Lactic Acid; Verlag Chemie: Copenhagen, Denmark, 1971.
19. Lipinsky, E. S.; Sinclair, R. G. Is Lactic Acid a Commodity Chemical? Chem. Eng. Prog. 1986, 82 (8), 25.
20. Datta, R. Hydroxycarboxylic acids. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J., Howe-Grant, M., Eds.; Wiley: New York, 1997; Vol. 13, p 1042.
21. Fisher, C. H.; Filachione, E. M. Properties and Reactions of Lactic Acid - A Review. U.S. Dep. Agric., Bur. Agric. Ind. Chem. 1950, AIC-279.
22. Genin, G. Lactic Acid and Its Applications. Lait 1951, 31, 204.
23. Nielsen, J. I.; Veibel, S. The Reactivity of Lactic Acid and Some of Its Simple Derivatives. Acta Polytech. Scand. 1967, #63.
24. Lunt, J. Large-scale production, properties, and commercial applications of polylactic acid polymers. Polym. Degrad. Stab. 1998, 59, 145.
25. Gunter, G. C.; Miller, D. J.; Jackson, J. E. Formation of 2,3-pentanedione from lactic acid over supported phosphate catalysts. J. Catal. 1994, 148, 252.
26. Domalski, E. S. Selected Values of Heat of Combustion and Heat of Formation of Organic Compounds Containing the Elements C, H, N, O, P, and S. J. Chem. Phys. Ref. Data 1972, 1 (2), 221.
27. Thauer, R.; Jungerman, K.; Decker, K. Energy Conservation in Chemotropic Anaerobic Bacteria. Bacteriol. Rev. 1977, 41, 100.
28. 4. J. Chem. Phys. Ref. Data 1985, 14 (1), 1.
29. Lebedev, B. V.; Kulagina, T. G.; Kiparisova, E. G. Thermodynamics of dl-Lactide, Ethylene Oxalate, and 2,5-Dioxo-piperazine in the Range 0-330 K. Zh. Fiz. Khim. 1982, 56, 2665.
30. Alen, R.; Sjostrom, E. Condensation of Glycolic, Lactic, and 2-Hydroxybutanoic Acids during Heating and Identification of the Condensation Products by GLC-MS. Acta Chem. Scand. 1980, B34, 633.
31. Barcza, L.; Mihalyi, K. Dimerization of Lower Fatty Acids in Aqueous Solution. Z. Phys. Chem. 1977, 104, 213.
32. Sorenson, W. R.; Campbell, T. W. Preparative Methods of Polymer Chemistry; Interscience Publishing: New York, 1968.
33. Mok, W.; Antal, M. J., Jr.; Jones, M. Formation of Acrylic Acid from Lactic Acid in Supercritical Water. J. Org. Chem. 1989, 54, 4596.
34. Keeler, R. Don't Let Food Go to Waste - Make Plastic Out of It. Res./Dev. 1991 (Feb.), 52.
35. Holmen, R. E. Acrylates by Catalytic Dehydration of Lactic Acid and Acrylates. U.S. Patent #2859240, 1958.
36. Sawicki, R. A. Catalyst for Dehydration of Lactic Acid to Acrylic Acid. U.S. Patent #4729978, 1988.
37. Paparizos, C.; Dolhyj, S.; Shaw, W. G. Catalytic Conversion of Lactic Acid and Ammonium Lactate to Acrylic Acid. U.S. Patent #4786756, 1988.
38. McCrackin, P. J.; Lira, C. T. Conversion of Lactic Acid to Acrylic Acid in Supercritical Water. Ind. Eng. Chem. Res. 1993, 32, 2608.
39. Walkup, P. C.; Rohrmann, C. A.; Hallen, R. T.; Eakin, D. E. Production of esters of lactic acid, esters of acrylic acid, lactic acid, and acrylic acid. U.S. Patent #5252473, 1993, #5071754, 1991.
40. Burns, R.; Jones, D. T.; Ritchie, P. D. Studies in Pyrolysis Part I. The Pyrolysis of Derivatives of Alpha-Acetoxypropionic Acid and Related Substances. J. Chem. Soc. 1935, 400.
41. Smith, L. T.; Fisher, C. H.; Ratchford, W. P.; Fein, M. L. Pyrolysis of Lactic Acid Derivatives. Ind. Eng. Chem. 1942, 34, 473.
42. Fisher, C. H.; Ratchford, W. P.; Smith, L. Methyl Acrylate Production. Ind. Eng. Chem. 1944, 36, 229.
43. Ratchford, W. P.; Fisher, C. H. Methyl Acrylate by Pyrolysis of Methyl Acetoxypropionate. Ind. Eng. Chem. 1945, 37, 382.
44. Komora, L.; Macho, V.; Sojka, J.; Polieva, M.; Palaczka, E. Alpha-Hydroxy Carboxylic Acids, Their Nitrates, Alpha-Beta Unsaturated Acids, and (or) Their Esters. Ger. Offen. 2144304, 1972.
45. Mercados Quimicos Industriales S. A., Alpha-Beta Unsaturated Acids and Their Esters. Span. ES 515891, 1983.
46. Hashimoto, M.; Honda, T. Alpha,Beta-Unsaturated Carboxylic Acids or Their Esters. Ger. Offen. DE 3141173, 1982.
47. Odell, B.; Earlam, G.; Cole-Hamilton, D. J. Hydrothermal Reactions of Lactic Acid Catalyzed by Group VIII Metal Complexes. J. Organomet. Chem. 1985, 290, 241.
48. Velenyi, L. J.; Dolhyi, S. R. Preparation of Aliphatic Carboxylic Acids and Aldehydes by Upgrading Alpha-Hydroxy Carboxylic Acids. U.S. Patent 4663479, 1987.
49. Bowden, E.; Adkins, H. Hydrogenation of Optically Active Compounds over Nickel and Copper-Chromium Oxide. J. Am. Chem. Soc. 1934, 56, 689.
50. Adkins, H.; Billica, H. R. Effect of Ratio of Catalyst and Other Factors upon the Rate of Hydrogenation. J. Am. Chem. Soc. 1948, 70, 3118.
51. Adkins, H.; Billica, H. R. The Hydrogenation of Esters to Alcohols at 25-150 °C. J. Am. Chem. Soc. 1948, 70, 3121.
52. Broadbent, H. S.; Campbell, G. C.; Bartley, W. J.; Johnson, J. H. Rhenium and Its Compounds as Hydrogenation Catalysts. III. Rhenium Heptoxide. J. Org. Chem. 1959, 24, 1847.
53. Carnahan, J. E.; Ford, T. A.; Gresham, W. F.; Grigsby, W. E.; Hager, G. F. Ruthenium-catalyzed hydrogenation of acids to alcohols. J. Am. Chem. Soc. 1955, 77, 3766.
54. Kitson, M.; Williams, P. S. Alcohols production by hydrogenation of carboxylic acids. U.S. Patent 4777303, 1988.
55. Kitson, M.; Williams, P. S. Catalyzed hydrogenation of carboxylic acids and their anhydrides to alcohols and /or esters. U.S. Patent 4985572, 1991.
56. Kitson, M.; Williams, P. S. Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters. U.S. Patent 5149680, 1992.
57. Kipax, J.; Harris, N.; Turner, K.; Anthony, B.; Rathnell, C. Ger. Patent DE 3443277 A1, 1985.
58. Maresca, L. M. Stabilizing a poly(aryl ether ketone). U.S. Patent #4611033, 1986.
59. Parliment, T. H., Flavoring with alpha,beta-keto-amines. U.S. Patent #4618501, 1985.
60. Wadley, D. C.; Tam, M. S.; Kokitkar, P. B.; Jackson, J. E.; Miller, D. J. Lactic Acid Conversion to 2,3-Pentanedione and Acrylic Acid over Silica-Supported Sodium Nitrate: Reaction Optimization and Identification of Sodium Lactate as the Active Catalyst. J. Catal. 1997, 165, 162.
61. Tam, M. S.; Craciun, R.; Miller, D. J.; Jackson, J. E. Reaction and Kinetic Studies of Lactic Acid Conversion over Alkali-Metal Salts. Ind. Eng. Chem. Res. 1998, 37, 2360.
62. Miller, D. J.; Jackson, J. E.; Langford, R. H.; Gunter, G. C.; Tam, M. S.; Kokitkar, P. B. Process for the Preparation of 2,3-Pentanedione. U.S. Patent 5731471, 1998.
63. 31P NMR Spectroscopic Analyses of Surface Species in Phosphate-Catalyzed Lactic Acid Conversion. J. Catal. 1996, 164, 207.
64. Miller, D. J.; Perry, S. M.; Fanson, P. T.; Jackson, J. E. Condensed Phase Preparation of 2,3-Pentanedione. U.S. Patent 5831130, 1998.
65. Smits, P. C.; Kuster, B.; van der Wiele, K.; van der Baan, H. S. The Selective Oxidation of Aldoses and Aldonic Acids to 2-Ketoaldonic Acids with Lead-Modified Platinum-on-Carbon Catalysts. Carbohydr. Res. 1986, 153, 227.
66. Sugiyama, S.; Shigemoto, N.; Masaoka, N.; Suetoh, S.; Hideaki, K.; Miyaura, K.; Hayashi, H. Vapor-Phase Oxidation of Ethyl Lactate to Pyruvate over Various Oxide Catalysts. Bull. Chem. Soc. Jpn. 1893, 66, 1542.
67. Jain, C. L.; Shankar, R.; Bakore, G. V. A Product Study of the Oxidation of Lactic Acid by One and Two Electron Oxidants Ind. J. Chem. 1969, 7, 159.
68. Kiyoura, T. Process for producing salts of pyruvic acid. U.S. Patent 4242525, 1980.
69. Christidis, Y.; Vallejos, J. Process for the manufacure of alkyl pyruvates. U.S. Patent 5053527, 1991.
70. Fumagalli, C. Succinic Acid and Anhydride, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J., Howe-Grant, M., Eds.; John Wiley and Sons: New York, 1997; Vol. 22.
71. Szmant, H. H. Organic Building Blocks of the Chemical Industry; J. W. Wiley and Sons: New York, 1989.
72. Chem. Mark. Rep. 1999, 255 (5), 34.
73. Felthouse, T.; Burnett, J.; Mitchell, S.; Mummey, M. Maleic Anhydride, Maleic Acid, and Fumaric Acid. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J., Howe-Grant, M., Eds.; John Wiley and Sons: New York, 1997; Vol. 15, p 893.
74. Turek, T.; Trimm, D. L. The Catalytic Hydrogenolysis of Esters to Alcohols. Catal. Rev.-Sci. Eng. 1994, 36, 645.
75. Thomas, D. J.; Stammbach, M. R.; Cant, N. W.; Wainwright, M. S.; Trimm, D. L. Hydrogenolysis of Dimethyl Succinate over Raney Copper Catalyst: A Correction. Ind. Eng. Chem. Res. 1990, 29, 204.
76. Turek, T.; Trimm, D. L.; Black, D. StC.; Cant, N. W. Hydrogenolysis of Dimethyl Succinate on Copper-Based Catalysts. Appl. Catal., A 1994, 116, 137.
77. Messori, M.; Vaccari, A.; Reaction Pathway in Vapor Phase Hydrogenation of Maleic Anhydride and Its Esters to Gamma-Butyrolactone. J. Catal. 1994, 150, 177.
78. Castiglioni, G.; Vaccari, A.; Fierro, G.; Inversi, M.; LoJacono, M.; Minelli, G.; Pettiti, I.; Porta, P.; Gazzano, M. Structure and Reactivity of Copper-Zinc-Cadmium Chromite Catalysts. Appl. Catal., A 1995, 123, 123.
79. Zhang, Q.; Wu, Z.; Xu, L. High-Pressure Hydrogenolysis of Diethyl Maleate on Cu-Zn-Al-O Catalysts. Ind. Eng. Chem. Res. 1998, 37, 3525.
80. Hermann, U.; Emig, G. Liquid-Phase Hydrogenation of Maleic Anhydride and Intermediates on Copper-Based and Noble Metal Catalysts. Ind. Eng. Chem. Res. 1997, 36, 2885.
81. Hermann, U.; Emig, G. Liquid-Phase Hydrogenation of Maleic Anhydride to 1,4-Butanediol in a Packed Bubble Column Reactor. Ind. Eng. Chem. Res. 1998, 37, 759.
82. Inagaki, H.; Nighimura, S.; Yoshinori, H.; Wada, K. Hydrogenation Reaction of Carbonyl Compounds Catalyzed by Cationic Ruthenium Complexes, in Science and Technology in Catalysis; Kodansha, Ltd.: Tokyo, 1994; p 327.
83. Hort, E. V.; Anderson, L. R. Pyrrole and Pyrrole Derivatives, in Encyclopedia of Chemical Technology, 3rd ed.; Mark, H. F., Othmer, D. H., Overberger, C. G., Seaborg, G. T., Eds.; John Wiley and Sons: New York, 1984; Vol. 19, p 510.
84. Barabas, E. S. N-Vinyl Amide Polymers, in Encyclopedia of Polymer Science and Engineering, 2nd ed.; Kroschwitz, J. L., Ed.; John Wiley and Sons: New York, 1989; Vol. 17, p 197.
85. U.S. International Trade Commission, ITC 1.14. Synthetic Organic Chemicals Production and Sales. 1991; p 990.
86. Commercial Literature, International Specialty Products, Inc. 1993.
87. Matson, M. S. Preparation of 2-Pyrrolidone. U.S. Patent #4904804, 1984.
88. Hollstein, E. J. Preparation of 2-Pyrrolidinone. U.S. Patent #3812149, 1974.
89. Hollstein, E. J.; Butte, W. A., Jr. Preparation of 2-Pyrrolidinone. U.S. Patent #3812148, 1974.
90. 6-N-alkylsuccinimides. U.S. Patent 4780547, 1988.
91. Olsen, R. J. Process for Making N-Alkylpyrrolidones. U.S. Patent #4,814,464, 1989.
92. Koehler U.; Siegel, H. Preparation of N-substituted pyrrolidones. U.S. Patent #5101045, 1991.
93. Johnson, W. S.; Daub, G. H. The Stobbe Condensation. Organic Reactions; John Wiley and Sons: New York, 1951; Vol. VI, Chapter 1.
94. Tate, B.; Berg, R. Synthesis of Citraconic Anhydride. U.S. Patent #3835162, 1974.
95. Terajima, A.; Ito, Y.; Matsuda, F.; Sahai, K.; Tsunemato, D.; Kamijo, T.; Harada, H. Preparation of (R)-2-(1-Naphthylmethyl) Succinic Acid as an Intermediate for Renin-inhibitory Peptides. Jpn. Kokai Tokkyo Koho 02157243, 1990.
96. Iizuka, K.; Kamijo, T.; Kubota, T.; Akaha, K.; Umeyama, H.; Kiso, Y. Preparation of Dipeptides Containing Statine and its Analogues as Antihypertensives. Jpn. Kokai Tokkyo Koho 62056458, 1987.
97. Iizuka, K.; Kamijo, T.; Kubota, T.; Akaha, K.; Umeyama, H.; Kiso, Y. Renin-inhibiting Histidine Derivatives as Antihypertensives. Eur. Patent Appl. 200406, 1986.
98. Banerjee, S.; Bagavant, G. Stereochemistry of Cyclohexylidene (Arylidene) succinates Formed in the Stobbe Condensation. Ind. J. Chem. 1981, 20B, 362.
99. Andersson, J. On the Preparation of Dibenzylidenesuccinic Acid by the Stobbe Condensation. Acta Chem. Scand. 1977, B31, 340.
100. El-Hashash, M. A.; Mohamed, M. M. Studies on Stobbe Condensation of 4-Isopropylacetophenone with Diethyl Succinate. Ind. J. Chem. 1980, 19B, 107.
101. Menon, C. S.; Zee-Cheng, R. K. Y.; Cheng, C. C. Synthesis of Dimethoxybenz[g] isoquinolines. J. Heterocycl. Chem. 1977, 14, 905.
102. Varadarajan, S. Chemical products from hydrogenation of succinate esters. M.S. Thesis, Michigan State University, 1996.
103. Scholten, J. J. F.; Konvalinka, J. A. Reaction of Nitrous Oxide with Copper Surfaces. Trans. Faraday Soc. 1969, 65, 2465.
104. Evans, J. W.; Wainwright, A. J.; Bridgewater, A. J.; Young, D. J. On the determination of Copper Surface Area by Reaction with Nitrous Oxide. Appl. Catal. 1983, 7, 75.
105. Daubert, T. E.; Danner, R. P. Physical and Thermodynamic Properties of Pure Chemicals; New York, Hemisphere Publishing Co., 1992.