Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1994-12-16
1996-04-23
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07C 5116
Patent
active
055105254
ABSTRACT:
A process for direct oxidative carbonylation of lower alkanes to acids having one greater carbon atom. The process uses a metal salt catalyst promoted by halide ions and/or a metal with oxygen as the oxidant in an aqueous medium. The process is especially effective for conversion of methane to acetic acid.
REFERENCES:
patent: 1916041 (1933-06-01), Dreyfus
patent: 2922809 (1960-01-01), Oberdorfer, Jr.
patent: 2926191 (1960-02-01), Lawson-Hall et al.
patent: 3215733 (1965-11-01), MacLean et al.
patent: 3284492 (1966-11-01), Fremery et al.
patent: 3876694 (1975-04-01), Gaenzler et al.
patent: 4101450 (1978-07-01), Hwang et al.
patent: 4414409 (1983-11-01), Waller
patent: 4469886 (1984-09-01), Pesa et al.
patent: 4494604 (1985-01-01), Shaw et al.
patent: 4613693 (1986-09-01), Ray
patent: 4665213 (1987-05-01), Alper et al.
patent: 4681707 (1987-07-01), Alper et al.
patent: 4681751 (1987-07-01), Gosser
patent: 4739107 (1988-04-01), Drent
patent: 4814538 (1989-03-01), Devries et al.
patent: 4895682 (1990-01-01), Ellis, Jr. et al.
patent: 4996357 (1991-02-01), Kojima et al.
patent: 5024984 (1991-06-01), Kaminsky et al.
patent: 5087786 (1992-02-01), Nubel et al.
patent: 5220080 (1993-06-01), Lyons et al.
patent: 5233113 (1993-08-01), Periana et al.
patent: 5258549 (1993-11-01), Pimblett
patent: 5281752 (1994-01-01), Fujiwara et al.
patent: 5286900 (1994-02-01), Hansen et al.
Baerns, M., van der Wiele, K., and Ross, J. R. H., Methane Activation--A Bibliography, Catal. Today, 4, 471-474, (1989).
Pitchai, R. and Klier, K., Partial Oxidation of Methane, Catal. Rev.-Sci. Eng., 28(1), 13-88, (1986).
Hunter, N. R., Gesser, H. D., Morton, L. A. Yarlagadda, P. S., and Fung, D. P. C., Methanol Formation at High Pressure by the Catalyzed Oxidation of Natural Gas and by the Sensitized Oxidation of Methane, Appl. Catal., 57, 45-54, (1990).
Burch, R., Squire, G. D., Tsang, S. C., Direct Conversion of Methane into Methanol, J. Chem. Soc., Faraday Trans. 1, 85(10), 3561-3568, (1989).
Kowalak, S. and Moffat, J. B., Partial Oxidation of Methane Catalyzed by H-Mordenite and Fluorinated Mordenite, Appl. Catal., 36, 139-145, (1988).
Stolarov, I. P., Vargaftik, M. N., Shishkin, D. I., and Moiseev, I. I., Oxidation of Ethane and Propane With Co(II) Catalyst, J. Chem. Soc., Commun., 938-939, (1991).
Vargaftik, M. N., Stolarov, I. P., and Moiseev, I. I., Highly Selective Partial Oxidation of Methane to Methyl Trifluoroacetate, J. Chem. Soc., Chem. Commun., 1049-1050, (1990).
Herron, N., The Selective Partial Oxidation of Alkanes Using Zeolite Based Catalysts, New J. Chem., 13, 761-766, (1989).
Lyons, J. E., Ellis, Jr., P. E., and Durante, V. A., Active Iron Oxo Centers for the Selective Oxidation of Alkanes, Stud. Surf. Sci. Catal., 67, 99-116, (1991).
Periana, R. A., Taube, D. J., Evitt, E. R., Loffler, D. G., Wentrcek, P. R., Voss, G. and Masuda, T., A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol, Science, 259, pp. 340-343, (1993).
Horvath, I. T., Cook, R. A., Millar, J. M. and Kiss, G., Low-Temperature Methane Chlorination with Aqueous Platinum Chlorides in the Pressence of Chlorine, Organometallics, 12, pp. 8-10, (1993).
Merzouki, M., Taouk, B., Monceaux, L., Bordes, E. and Courtine, P., Catalytic Properties of Promoted Vanadium Oxide in the Oxidation of Ethane in Acetic Acid, New Developments in Selective Oxidation by Heterogeneous Catalysis; Studies in Surface Science and Catalysis, Ruiz, P. and Delmon, B., Eds., vol. 72, pp. 165-179, (1992).
Thomas, C. L., Catalytic Processes and Proven Catalysts, Academic, New York, 104, (1970).
Happel, J., Study of Knietic Structure Using Marked Atoms, Catal. Rev., 6, (2), 221-260, (1972).
Laine, R. M., and Wilson, Jr., R. B., Recent Developments in the Homogeneous Catalysis of the Water-Gas Shift Reaction, in Aspects of Homogeneous Catalysis, Ugo, R., Ed., D. Reidel, Dordrecht, 5, 217-240, (1984).
Ford, P. C., The Water Gas Shift Reaction: Homogeneous Catalysis by Ruthenium and Other Metal Carbonyls, Acc. Chem. Res., 14, 2, 31-37, (1981).
Fu, L., Chuang, K. T. and Fiedorow, R., Selective Oxidation of Hydrogen to Hydrogen Peroxide, New Developments in Selective Oxidation by Heterogeneous Catalysis; Studies in Surface Science and Catalysis, Ruiz, P. and Delmon, B., Eds., vol. 72, pp. 33-41, (1992).
Nicoletti, J. W. and Whitesides, G. M., Liquid-Phase Oxidation of 2-Propanol to Acetone by Dioxygen Using Supported Platinum Catalysts, J. Phys., Chem., 93, 759-767, (1989).
Sen, A. and Lin, M., A Novel Hybrid System for the Direct Oxidation of Ethane to Acetic and Glycolic Acids in Aqueous Medium, J. Chem. Soc., Chem. Commun., 6, 508-510, (1992).
Sen, A., Lin, M., Kao, L. C., and Hutson, A. C., J. Am. Chem. Soc. 114, 6385, (1992).
Jones, W. D., Development of Catalytic Processes for the Synthesis of Organic Compounds the Involve C-H Bond Activation, Chap. 5, 113-148, Selective Hydrocarbond Activation, Principles and Progress, Edited by Davies, J. A., Watson, P. L., Greenberg, A. and Lichman, J. F., VCH, (1990).
Lin, M. and Sen, A., A Highly Catalytic System for the Direct Oxidation of Lower Alkanes by Dioxygen in Aqueous Medium. A Formal Heterogeneous Analog of Alkane Monooxtgenases, J. Am. Chem. Soc., 114, 7307-7308, (1992).
Kunai, A, Wani, T, Uehara, Y, Iwasaki, Kuroda, Y, Ito, S, and Sasaki, K., Catalytic Oxidation of Benzene. Catalyst Design and Its Performance, Bull. Chem. Soc. Jpn., 62, 2613-2617, (1989).
Kuroda, Y., Kunaai, A., Hamada, M., Kitano, T., Ito, S. and Sasaki, K., Catalytic Oxidation of Naphthalene on Palladium in Cooperation with Copper (I)/(II) Redox Couple, Bull. Chem. Soc. Jpn., 64, 3089-3093, (1991).
Groh, S. E. and Nelson, M. J., Mechanisms of Activation of Carbon-Hydrogen Bonds by Metalloenzymes, Chap. 10, 305-378, in Selective Hydrocarbon Activation, Davies, J. A., Watson, P. L., Liebman, J. F., Greenberg, A., Eds. VCH, New York, (1990).
Ortiz de Montellano, P. R., Oxygen Activation and Transfer, Chap. 7, 217-271, in Cytochrome P-450: Structure, Mechanism and Biochemistry, Ortiz de Montellano, P. R., Ed., Plenum, New York, (1986).
Guengerich, F. P. and MacDonald, T. L., Chemical Mechanisms of Catalysis by Cytochromes P-450: A Unified View, Acc. Chem. Res., 17, 9-16, (1984).
Groves, J. T., Key Elements of the Chemistry of Ctochrome P-450, J. Chem. Ed., 62, 11, 928-931, (1985).
Walling, C., Fenton's Reagent Revisited, Acc. Chem. Res. 8, 125-131, (1975).
Bakak, A. and Espenson, J. H., Kinetics of the Capture of Methyl Radicals by Carbon Monoxide in Aqueous Solution, J. Chem. Soc., Chem. Commun., 21, 1497-1498, (1991).
Lin, M. and Sen, A., Oxidation and Oxidative Carbonylation of Methane and Ethane by Hexaoxo-.mu.-peroxodifulfate (2-) Ion in Aqueous Medium, J. Chem. Soc., Chem. Commun. 12, 892-893, (1992).
Kung, H. H., Selective Oxidation Catalysis II, Stud. Surf. Sci. Catal., 45, 200-226, (1989).
Nishiguchi, T., Nakata, K., Takaki, K. and Fujiwara, Y. Chem. Lett., 1141-1142, (1992).
Lin, M. and Sen, A., J. Chem. Soc., Chem. Commun., 892-893 (1992).
Lin, M. and Sen, A., J. Am. Chem. Soc., 114, 7307-7308, 1992.
Wade, L. E., Gengelbach, R. B., Trumbley, J. L., Kirk-Othmer Encyclopedia of Chemical Technology, vol. 15, 398-415, Wiley, New York (1978).
Wagner, F. S., Kirk-Othmer Encyclopedia of Chemical Technology, vol. 1, 124-147, Wiley, New York (1978).
Forster, D., Adv. Organomet, Chem, 17, 255-267, (1979).
Whitesides, G. M., et al., Organometallics 4, 1819-1830, (1985).
Sen, A., Lin, M., Kao, L-C & Hutson, A. C., J. Am. Chem. Soc. 114, 6385-6392 (1992).
Luinstra, G. A., Labinger, J. A., Bercaw, J. E., J. Am. Chem. Soc. 115, 3004-3005 (1993).
Kushch, L. A., Lavrushko, V. V., Misharin, Yu. S., Moravsky, A. P. & Shilov, A. E. Nouv. J. Chem. 7, 729-733 (1983).
Lin, M., Sen, Ayusman, Direct catalytic conversion of methane to acetic acid in an aqueous medium, Letters To Nature vol. 368, 613-615 (1994).
Lin Minren
Sen Ayusman
Conrad, III Joseph M.
Dees Jos,e G.
Gas Research Institute
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