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Production of Maleic Anhydride

  • Chapter
Maleic Anhydride

Abstract

The first commercial process for MA production was put into use by National Aniline and Chemical in 1928.* It used the Weiss and Downs process employing benzene as a raw material.(1) In 1930, Monsanto made available MA which was a by-product of their phthalic anhydride manufacture. Petrotex also used their butene-based process in the early 1960s, which was later abandoned in favor of a benzene-based process in 1967. Benzene is still the most popular feed today. Reportedly 90% of world capacity for MA uses benzene.(2) Even when benzene was a coal-derived chemical, it was abundant. With the development of the petrochemical industry, benzene was available in larger quantities at lower prices. As a result it became a more attractive raw material. However, the petrochemical industry has in recent years made C4 hydrocarbons available. There is stoichiometric advantage in using C4 hydrocarbons over benzene since in the latter two carbons or one-third of the molecule is wasted. Thus, ideally 100 lb of benzene would yield 125.6 lb of MA whereas 100 lb of butane would give 168.9 lb of MA. This intrinsic advantage of C4-hydrocarbon-based raw material has shown greater activity for MA production in recent years.

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References

  1. W. Haynes, American Chemical Industry, Vol. 5, D. Van Nostrand, New York (1954).

    Google Scholar 

  2. Journal of Commerce, Jan. 17, 1979.

    Google Scholar 

  3. I. G. Farbenindustrie A.G., Fr. Pat. 721,763 (1932).

    Google Scholar 

  4. O. Drossback (to I. G. Farbenindustrie A.G.), U.S. Pat. 1,880,901 (1932).

    Google Scholar 

  5. K. Vaidyanathan, Chem. Age India 19(5), 363 (1968).

    CAS  Google Scholar 

  6. J. M. Church and P. Bitha, Ind. Eng. Chem. Prod. Res. Dev. 2(1), 61 (1963).

    Article  CAS  Google Scholar 

  7. A. Boehringer (to C. H. Boehringer), Brit. 297, 667 (1929).

    Google Scholar 

  8. J. D. Bacha, J. S. Matthews and C. M. Selwitz (to Gulf Research and Development), U.S. Pat. 4,065,470 (1977).

    Google Scholar 

  9. N. Nagamuri and M. Matsumoto, Japan Pat. 10,665 (1957).

    Google Scholar 

  10. W. G. Parks and R. W. Yule, Ind. Eng. Chem. 33, 891 (1941).

    Article  CAS  Google Scholar 

  11. American Cyanamid Co., Brit. Pat. 754,665 (1956).

    Google Scholar 

  12. S. Morita, Bull. Chem. Soc. Jap. 33, 309 (1960).

    Article  CAS  Google Scholar 

  13. C. K. Clark and J. E. Hawking, Ind. Eng. Chem. 33(9), 1177 (1941).

    Article  CAS  Google Scholar 

  14. E. R. Neilsen (to Quaker Oats), U.S. Pat. 2,421,428 (1947).

    Google Scholar 

  15. C. D. Hurd and H. G. Glass, J. Am. Chem. Soc. 61, 3490 (1939).

    Article  CAS  Google Scholar 

  16. R. Kempf, Ber. Dtsch. Chem. Ges. 39, 3715 (1906)

    Article  Google Scholar 

  17. J. Pelouze, Anal. Pharmacie 11, 263 (1834).

    Article  Google Scholar 

  18. Kirk Othmer Encyclopedia of Chemical Technology, “Maleic Acid, Fumaric Acid, Maleic Anhydride,” Vol. 12, J. Wiley, New York (1967).

    Google Scholar 

  19. P. L. Morse, Maleic Anhydride Report No. 46, Standford Research Institute, Palo Alto, California (1969)

    Google Scholar 

  20. R. H. Perry, C. H. Chilton, and S. D. Kirkpatrick, Chemical Engineers Handbook, 4th ed., McGraw-Hill, New York (1963).

    Google Scholar 

  21. D. M. Comidine, Chemical and Process Technology Encyclopedia, McGraw-Hill, New York (1974).

    Google Scholar 

  22. P. Kullavanijya, Ph.D. thesis, “Statistical Study of the Benzene Oxidation Process in a Fluidized Bed Reactor,” Ohio State University (1966).

    Google Scholar 

  23. A. Weisburger, Technique in Organic Chemistry, Vol. 2, Interscience, New York (1956).

    Google Scholar 

  24. M. Ito, Yuki Gosei Kogatu Kyokai Shi 34(7), 505 (1975).

    Article  Google Scholar 

  25. Handbook of Industrial Chemicals, J. A. Kent, ed., Van Nostrand Reinhold, New York (1974).

    Google Scholar 

  26. R. O. Kerr (to PPG), U.S. Pat. 3,074,969 (1963).

    Google Scholar 

  27. R. O. Kerr, W. R. Decker, and C. M. Dorsett (to PPG), U.S. Pat. 3,163,613 (1964).

    Google Scholar 

  28. Process Development Digest (Chem. Systems Inc.) 1(2), 1 (1977).

    Google Scholar 

  29. S. K. Bhattacharya and N. Venkataraman, J. Appl. Chem. 8, 728 (1958).

    Article  Google Scholar 

  30. J. M. Weiss and C. R. Downs, J. Am. Chem. Soc. 45, 1003 (1923).

    Article  CAS  Google Scholar 

  31. J. M. Weiss and C. R. Downs, J. Am. Chem. Soc. 45, 2341 (1923).

    Article  CAS  Google Scholar 

  32. J. M. Weiss and C. R. Downs, Ind. Eng. Chem. 12, 228 (1920).

    Article  CAS  Google Scholar 

  33. D. M. Newitt and J. H. Burgoyna, Proc. Royal Soc. London A153, 448 (1936).

    Article  CAS  Google Scholar 

  34. V. V. Pigulerskii and E. V. Yarzhemskaya, J. Gen. Chem. USSR 5, 1620 (1935).

    Google Scholar 

  35. W. Griedrichson, G. Peocler, and O. Goehre (to BASF A.G.), Fr. Pat. 1,495,765 (1966).

    Google Scholar 

  36. R. H. Bretton S. Wan, and B. F. Dodge, Ind. Eng. Chem. 44(3),594 (1952).

    Article  CAS  Google Scholar 

  37. CRC Handbook of Chemistry and Physics, Chemical Rubber Co., Cleveland, Ohio (1970).

    Google Scholar 

  38. R. O. Kerr, Benzene and Its Derivatives, E. G. Hancock, ed., J. Wiley, New York (1975).

    Google Scholar 

  39. J. M. Feder (to Scientific Design Co.), U.S. Pat. 3,054,806 (1962).

    Google Scholar 

  40. W. M Cooper (to Monsanto), U.S. Pat. 2,951,555 (1960).

    Google Scholar 

  41. I. Nagai, Kobunshi Ronbunshu 19(216), 249 (1970).

    CAS  Google Scholar 

  42. J. M Weiss, U.S. Pat. 2,462,444 (1949).

    Google Scholar 

  43. J. M. Weiss, Brit. Pat. 609,533 (1948).

    Google Scholar 

  44. J. N. Ospenson (to California Spray Chemical). U.S. Pat. 2,734,854 (1956).

    Google Scholar 

  45. L. K. Beach (to Esso Research), U.S. Pat. 2,729,600 (1956).

    Google Scholar 

  46. Ugine, Fr. Pat. 1,317,308 (1963).

    Google Scholar 

  47. H. Hafercorn (to Veba Chemie A.G.), Gen. Offen. 2,411,101 (1975).

    Google Scholar 

  48. J. D. Gardner and J. F. Manning (to Chevron Research), U.S. Pat. 3,939,103 (1976).

    Google Scholar 

  49. Z. Nusa, S. Hillers, M. V. Shimanskaya, and J. Zile, Latv. PSR Sinat. Akad. Vestis. Kin. 3, 356 (1971); Chem. Abstr. 75, 129295e (1971).

    Google Scholar 

  50. I. Sakiabi and T. Nomura (to Takeda Chem.), Japan Pat. 71 21,849 (1971); Chem. Abstr. 75, 152295n (1971).

    Google Scholar 

  51. T. Matsuura, T. Terahata, S. Tazawa, and H. Imai (to Mitsubishi Chem.), Japan Pat. 72 13,025 (1972); Chem. Abstr 77, 47888a (1972).

    Google Scholar 

  52. J. B. Feder (to Halcon International), Gen. Offen. 2,008,619 (1970)

    Google Scholar 

  53. Montecantini, Brit. Pat. 858,622 (1 961)

    Google Scholar 

  54. N. Ayukawa, T. Ohtsuka, M. Koshimura, and T. Yamamoto (to Nippon Oils and Fats), Jap. Pat. 92,015 (1974); Chem. Abstr. 82 86823y (1975)

    Google Scholar 

  55. N. Ayukawa, T. Ohtsuka, H. Bessy, T. Yamada, S. Sumita, N. Nakayama, and Y. Murata (to Nippon Oils and Fats), Japan Patent 92,014 (1974); Chem. Abstr. 82, 112412 (1975).

    Google Scholar 

  56. A. M. Smith and E. B. Recla (to Allied Chem.), U.S. Pat. 3,850,758 (1973).

    Google Scholar 

  57. R. Matsura, T. Terahata, S. Tazawa, and H. Imai (to Mitsubishi Chem.), Japan Pat. 73,87,613 (1973); Chem. Abstr. 79, 927993 (1973).

    Google Scholar 

  58. Monsanto Co., Brit. Pat. 1,204,846 (1968).

    Google Scholar 

  59. W. G. Bowman (to Petrotex), U.S. Pat. 3,115,503 (1963).

    Google Scholar 

  60. B. Lewis and G. Von Elbe, Combustion, Flames, and Explosions of Gases, Academic Press, New York (1961).

    Google Scholar 

  61. Hydrocarbon Proc. 48(11), 197 (1969).

    Google Scholar 

  62. Hydrocarbon Proc. 44(11), 237 (1965).

    Google Scholar 

  63. Hydrocarbon Proc. 48(11). 198 (1969).

    Google Scholar 

  64. Hydrocarbon Proc. 54(11), 160 (1975).

    Google Scholar 

  65. A. Di Cio and G. Zettel, Hydrocarbon Proc. 50(9),167 (1971).

    Google Scholar 

  66. S. Ushimo, Chem. Eng. 78(21), 107 (1971).

    Google Scholar 

  67. Hydrocarbon Proc. 50(11). 176 (1971).

    Google Scholar 

  68. S. Ueno and S. Kamimura, Sekiyu Gakkai Shi 16(8),632. (1973).

    CAS  Google Scholar 

  69. Hydrocarbon Proc. 50(1 1) 175 (1971).

    Google Scholar 

  70. W. K. Ashcroft and I. M. Clifford, Chem. Prod., 11, Jan. (1961).

    Google Scholar 

  71. E. Weyens, Hydrocarbon Proc. 53(11) 132 (1974).

    CAS  Google Scholar 

  72. Chemical Economics Handbook, Vol. 8, 672.5032 c SRI, Menlo Park, California (July, 1976).

    Google Scholar 

  73. S. R. Rafikov, P. V. Suvorov, and A. V. Solmin, Izvest. Akad. Nauk SSSR Ser. Khim., 58 (1957).

    Google Scholar 

  74. J. D. Butler and B. G. Weston, J. Catal. 2, 8 (1963).

    Article  CAS  Google Scholar 

  75. J. K. Dixon and J. E. Longfield, Catalysis, Vol. 7, P. Emmett, ed., Reinhold, New York (1960).

    Google Scholar 

  76. C. G. B. Hammar, Sven. Kern. Tidskv. 64, 165 (1952).

    CAS  Google Scholar 

  77. B. Dmuchovsky, M. C. Freerks, E. D. Pierron, R. H. Munch, and F. B. Zienty, J. Catal. 4, 291–300 (1965).

    Article  CAS  Google Scholar 

  78. J. Mars and D. W. Van Krevelen, Chem. Eng. Sci. 3, Spec. Suppl., 41 (1954).

    Google Scholar 

  79. J. N. Holsen, Ph.D. thesis, “An Investigation of the Catalytic Vapor Phase Oxidation of Benzene,” Washington University, St. Louis, Missouri (1954).

    Google Scholar 

  80. R. Hayasky, R. R. Hudgins, and W. F. Graydon, Can. J. Chem. Eng., 220 (1963).

    Google Scholar 

  81. G. Boocock and R. J. Cuetanovik, Can. J. Chem. 39, 2436 (1961).

    Article  CAS  Google Scholar 

  82. T. C. Bisset and K. A. Benson, Ind. Eng. Chem. Prod. Res. Dev. 2, 57 (1963).

    Article  Google Scholar 

  83. M. Ai, P. Boutry, and R. Montarnal, Bull. Soc. Chim. Fr. 8–9, 2775 (1970).

    Google Scholar 

  84. L. K. Beach (to Standard Oil Development), U.S. Pat. 2,537,568 (1951)

    Google Scholar 

  85. R. Sampson and D. Shooter, Oxidation and Combustion Review, Vol. 1, C. F. H. Tippel, ed., Elsevier, Amsterdam (1965).

    Google Scholar 

  86. M. Akimoto and E. Echigoya, Bull. Chem. Soc. Jap. 48(12),3518 (1975)

    Article  CAS  Google Scholar 

  87. M. Akimoto and E. Echigoya, J. Catal. 31, 278 (1973).

    Article  CAS  Google Scholar 

  88. J. M. Weiss and C. R. Downs, U.S. Pat. 1,318,632 (1920).

    Google Scholar 

  89. J. L. Ragle, J. Chem. Phys. 38, 2020 (1963)

    Article  CAS  Google Scholar 

  90. A. Bielanski and A. Inglot, Bull. Polish Acad. Sci. 22, 773 (1974)

    CAS  Google Scholar 

  91. A. Bielanski and A. Inglot, Bull. Polish Acad. Sci. 22, 784 (1974).

    Google Scholar 

  92. I. I. Ioffe, Z. I. Ezhkova, and A. G. Lyubarskii, Kinet. Catal. 3, 194 (1962).

    CAS  Google Scholar 

  93. R. H. Munch and E. D. Pierron, J. Catal. 3, 406 (1964).

    Article  CAS  Google Scholar 

  94. M. Ai and T. Ikawa, J. Catal. 40, 203 (1975).

    Article  CAS  Google Scholar 

  95. M. Ai, Bull. Chem. Soc. Jap. 50(2), 355 (1977).

    Article  CAS  Google Scholar 

  96. M. Akimoto and E. Echigoya, J. Catal. 31, 191 (1973).

    Article  Google Scholar 

  97. M. Akimoto and E. Echigoya, J. Chem. Soc. Faraday Trans. 73 (2), 193 (1977).

    CAS  Google Scholar 

  98. M. Akimoto and E. Echigoya, J. Catal. 35, 278 (1974).

    Article  CAS  Google Scholar 

  99. P. L. Morse, Maleic Anhydride Report 46A1, Standford Research Institute, Palo Alto, California (1973).

    Google Scholar 

  100. BASF, Brit. Pat. 1,291,354 (1972).

    Google Scholar 

  101. M. Ai, P. Boutry, R. Montarnal, and G. Thomas, Bull. Soc. Chim. Fr. 8–9, 2783 (1970).

    Google Scholar 

  102. M. Ai, J. Catal. 40, 318 (1975).

    Article  CAS  Google Scholar 

  103. M. Ai, J. Catal. 40, 327 (1975).

    Article  CAS  Google Scholar 

  104. M. Ai, Bull. Chem. Soc. Jap. 50(10),2579 (1977).

    Article  CAS  Google Scholar 

  105. M. Ai, J. Catal. 49, 313 (1977).

    Article  CAS  Google Scholar 

  106. M. Akimoto and E. Echigoya, Bull. Jap. Petroleum Inst. 16(1), 8 (1974).

    Article  CAS  Google Scholar 

  107. Chemical Marketing Reporter, p. 5, Aug. 20 (1979).

    Google Scholar 

  108. Standard Oil, Ohio, Brit. Pat. 1,528,317 (1978).

    Google Scholar 

  109. Standard Oil, Ohio, Brit. Pat 1,528,318 (1978).

    Google Scholar 

  110. K. Wohlfahrt and G. Emig, Hydrocarbon Proc. 60(6),83 (1980).

    CAS  Google Scholar 

  111. Federal Register 45(77), 26660–84, April 18 (1980).

    Google Scholar 

  112. G. M. Rinaldi and T. W. Hughes, Proceedings of the Special Conference on Control Specific (Toxic) Pollutants, Florida, 1979, E. R. Frederick ed., APCA, Pittsburgh, Pennsylvania (1979), pp. 405–414.

    Google Scholar 

  113. G. Franz, F. Nierlick, and H. J. Ratajczak (to Chemische Werke Huls AG.), Gen. Offen. 2,902,986 (1980).

    Google Scholar 

  114. G. Emig, F. Trifro, and H. Hofmann, Chem.-Ztg. 104(5),165 (1980);

    CAS  Google Scholar 

  115. G. Emig, F. Trifro, and H. Hofmann, Chem. Abstr. 93, 132825c (1980).

    Google Scholar 

  116. D. A. DeMaio, Chem. Eng. 87(10), 104 (1980).

    CAS  Google Scholar 

  117. Chemical Marketing Reporter, Dec. 8 (1980).

    Google Scholar 

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Trivedi, B.C., Culbertson, B.M. (1982). Production of Maleic Anhydride. In: Maleic Anhydride. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-0940-7_2

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