Resorcinol pp 125-134 | Cite as

m-Aminophenol

  • Hans Dressler
Part of the Topics in Applied Chemistry book series (TAPP)

Abstract

m-Aminophenol (MAP), 6–1, is an important starting material for dyes, including a variety of leuco (or latent) dyes used in imaging technology, optical bleaches and fluorescent agents (see Chapter 10), drugs (see Chapter 8), agricultural chemicals (see Chapter 7), and high-performance polymers (see Chapter 9). Although the synthesis of m-aminophenol(s) by the reaction of resorcinol with ammonia or (di)alkylamines has been known for about 100 years,1,2 the preferred manufacturing process had been for many years a route involving the sulfonation of nitrobenzene to m-nitrobenzenesulfonic acid, the reduction of the nitro group to give m-aminobenzenesulfonic acid, followed by the caustic fusion of sodium m-aminobenzenesulfonate to yield sodium m-aminophenolate. The m-aminophenol was isolated/purified by neutralization, filtration, and recrystallization; the overall yield of m-aminophenol from nitrobenzene was estimated by SRI International to be 58%.3 (Doubtless, process improvements were made by the producers using this process.) The nitrobenzene/sulfonation/reduction/caustic fusion route is still being used commercially, notably by ACNA in Italy, the largest producer of MAP, as well as a few smaller manufacturers. Sumitomo Chemical Co. used this process as well into the early 1980s and had licensed their knowhow to Hindustani Organic Chemicals, Ltd. of India which started up a plant on this basis with a capacity for MAP of 1.5 mill. 1b /yr in 1970.4 The output of the Indian plant was said to be devoted to making sodium p-aminosalycilate (PAS; see Chapter 8), a tuberculostatic agent.

Keywords

Butyl Ether Gallium Oxide Diisopropyl Ether Extractive Distillation Tetraethylene Glycol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Ger. Pat. 49,060 (Aug. 21, 1889; to A. Leonhardt & Co.).Google Scholar
  2. 2.
    Ger. Pat. 121,683 (May 13, 1901; to Badische Anilin-Und Soda-Fabrik).Google Scholar
  3. 3.
    SRI (Stanford Research Institue)-PEP (Process Economics Program) Report No. 171B, Pesticides and Intermediates—Supplement B, by Y.-C. Yen and D. J. Lin, with contributions by C.-W. Lee, Sept. 1986, p. 169.Google Scholar
  4. 4.
    Jap. Chem. Week, Sept. 17, 1970, p. 33.Google Scholar
  5. 5.
    Chem. Week, Aug. 20, 1986, p. 73.Google Scholar
  6. 6.
    Ger. Offen. DE 2,140,786 (Feb. 22, 1973; R. Berthold, A. Topp, and G. Schaeffer to Farbwerke Hoechst A.-G.); C.A., 78, 124270 (1973).Google Scholar
  7. 7.
    Ger. Offen. DE 2,426,186 (Dec. 18, 1975; H. J. Quadbeck-Seeher and H. Hoch to BASF A.-G.); C.A., 84, 89816 (1976).Google Scholar
  8. 8.
    Jpn. Kokai Tokkyo Koho JP 55,053,250 (Apr. 18, 1980; to Mitsui Petrochemical Industries, Ltd.); C.A., 93, 114135 (1980).Google Scholar
  9. 9.
    Jpn. Kokai Tokkyo Koho JP 80,004,338 (Jan. 12, 1980; T. Nagaoka, S. Shimizu, and H. Hayashi to Mitsui Petrochemical Industries, Ltd.); C.A., 93, 7837 (1980).Google Scholar
  10. 10.
    Jpn. Kokai Tokkyo Koho JP 80,015,412 (Feb. 2, 1980; T. Nagaoka, S. Shimizu, and H. Hayashi to Mitsui Petrochemical Industries, Ltd.); C.A., 93, 167890 (1980).Google Scholar
  11. 11.
    Jpn. Kokai Tokkyo Koho JP 80,053,246 (Apr. 18, 1980; to Mitsui Petrochemical Industries, Ltd.); C.A., 94, 15389(1981).Google Scholar
  12. 12.
    Jpn. Kokai Tokkyo Koho JP 61,007,239 [86,007,239] (Jan. 13, 1986; F. Matsunaga, E. Kato, T. Kimura, and Y. Isoda to Mitsui Petrochemical Industries, Ltd.; Honshu Chemical Industry Co., Ltd.); C.A., 104, 186128(1986).Google Scholar
  13. 13.
    Jpn. Kokai Tokkyo Koho JP 60,215,654 [85,215,654] (Oct. 29, 1985; M. Tanaka, K. Taniguchi, and K. Saeki to Mitsui Petrochemical Industries, Ltd.); C.A., 106, 49767 (1987).Google Scholar
  14. 14.
    Eur. Pat. Appl. EP 197,633 (Oct. 15,1986; H. Harada, H. Maki, and S. Sasaki to Sumitomo Chemical Co., Ltd.); C.A., 106, 66891 (1987).Google Scholar
  15. 15.
    U.S. Pat. 4,585,896 (Apr. 29, 1986; H. Harada, H. Maki, and S. Sasaki to Sumitomo Chemical Co., Ltd.).Google Scholar
  16. 16.
    Jpn. Pat. JP 86,051,577 (Nov. 10, 1986; to Mitsui Petrochemical Industries, K.K.).Google Scholar
  17. 17.
    Jpn. Pat. JP 86,007,239 (Jan. 13, 1986; F. Matsunaga, E. Kato, T. Kimura, and Y. Isoda to Mitsui Petrochemical Industries, Ltd.; Honshu Chemical Industry Co., Ltd.).Google Scholar
  18. 18.
    Jpn. Kokai Tokkyo Koho JP 81,073,048 (June 17, 1981; to Mitsui Petrochemical Co., Ltd.); C.A., 95,150185 (1981).Google Scholar
  19. 19.
    Eur. Pat. Appl. EP 449,546 (Oct. 2, 1991; H. Dressier to INDSPEC Chemical Corp.); equiv. U.S. Pat. 5, 130,489 (July 14, 1992; same assignment).Google Scholar
  20. 20.
    Ger. Offen. DE 2,900,193 (July 24, 1980; H. J. Kollinger and H. Scheuermann to BASF A.-G.); C.A., 93, 186187 (1980).Google Scholar
  21. 21.
    Jpn. Kokai Tokkyo Koho JP 81,073,048 (June 17, 1981; to Mitsui Petrochemical Industries, Ltd.); C.A., 95, 150185 (1981).Google Scholar
  22. 22.
    Eur. Pat. Appl. EP 181,505 (May 21, 1986; N. Yonese and M. Kondo to Kanzaki Paper Manufacturing Co., Ltd.); also, U.S. Pat. 4,713,488 (Dec. 15, 1987; same assignment).Google Scholar
  23. 23.
    Jpn. Kokai Tokkyo Koho JP 62,048,654 [87,048,654] (March 3, 1987; H. Harada, H. Maki, and S. Sasaki to Sumitomo Chemical Industries, K.K.); C.A., 107, 58645 (1987).Google Scholar
  24. 24.
    Jpn. Kokai Tokkyo Koho JP 62,258,345 [87,258,345] (Nov. 10, 1987; H. Harada, H. Maki, and S. Sasaki to Sumitomo Chemical Co., Ltd.); C.A., 109, 149059 (1988).Google Scholar
  25. 25.
    Jpn. Kokai Tokkyo Koho JP 62,258,346 [87,258,346] (Nov. 10, 1987; H. Harada. H. Maki, and S. Sasaki to Sumitomo Chemical Co., Ltd.); C.A., 109, 149060 (1988).Google Scholar
  26. 26.
    Jpn. Kokai Tokkyo Koho JP 02,101,053 [90,101,053] (Apr. 12, 1990; T. Deu, K. Tsuzukibashi, Y. Suzuki, S. Sanpei, K. Hatano, and T. Kurihara to Koriyama Kasei Co., Ltd.); C.A., 113, 40149 (1990).Google Scholar
  27. 27.
    Jpn. Kokai Tokkyo Koho JP 03,063,250 [91,063,250] (March 19, 1991; H. Maki, M. Kawasaki, H. Shimizu, and T. Ito to Sumitomo Chemical Co., Ltd); C.A., 115, 73626 (1991).Google Scholar
  28. 28.
    Jpn. Kokai Tokkyo Koho JP 03,020,251 [91,020,251] (Jan. 29, 1991; M. Kondo, Y. Kurano, S. Yamamoto, and M. Tanaka to Mitsui Petrochemical Industries, Ltd.); C.A., 114, 228523 (1991).Google Scholar
  29. 29.
    Jpn. Kokai Tokkyo Koho JP 03,099,043 [91,099,043] (Apr. 24, 1991; M. Kondo and N. Hirowatari to Mitsui Petrochemical Industries, Ltd.); C.A., 115, 182822 (1991).Google Scholar
  30. 30.
    Jpn. Kokai Tokkyo Koho JP 04,077,460 [92,077,460] (March 11, 1992; M. Nakatsuka, A. Otsuji, and T. Yamaguchi to Mitsui Toatsu Kagaku K.K.); C.A., 117, 89957 (1992).Google Scholar
  31. 31.
    Jpn. Kokai Tokkyo Koho JP 04,300,856 [92,300,856] (Oct. 23, 1992; M. Nakatsuka, A. Otsuji, and T. Yamaguchi to Mitsui Toatsu Chemicals, Inc.); C.A., 118, 128198 (1992).Google Scholar
  32. 32.
    Eur. Pat. Appl. EP 514,687 (Nov. 25, 1992; M. Hauptreif and H. Reichelt to BASF A.G.); C.A., 118, 193632(1992).Google Scholar
  33. 33.
    U.S. Pat. 4,212,823 (July 15, 1980; W. H. Mueller to Hoechst A.-G.).Google Scholar
  34. 34.
    Ger. Offen. DE 3,120,245 (Dec. 9, 1982; W. Reimann and W. H. Mueller to Hoechst A.-G.); C.A., 98, 143117 (1983).Google Scholar
  35. 35.
    PCT Int. Appl. WO 92,018,445 (Oct. 29, 1992; S. E. Jacobson to E. I. duPont de Nemours and Co.); C.A., 118, 24107 (1992).Google Scholar
  36. 36.
    U.S. Pat. 5,149,874 (Sept. 22, 1992; S. E. Jacobson to E. I. duPont de Nemours and Co.).Google Scholar
  37. 37.
    Jpn. Kokai Tokkyo Koho JP 62,061,956 [87,061,956] (March 18, 1987; H. Harada, H. Maki, and S. Sasaki to Sumitomo Chemical Co., Ltd.); C.A., 107, 115359 (1987).Google Scholar
  38. 38.
    Jpn. Kokai Tokkyo Koho JP 02,209,851 [90,209,851] (Aug. 21, 1990; T. Ogino and H. Ishida to Mitsui Petrochemical Industries, Ltd.); C.A., 114, 6015 (1991).Google Scholar

Copyright information

© Springer Science+Business Media New York 1994

Authors and Affiliations

  • Hans Dressler
    • 1
  1. 1.Formerly of INDSPEC Chemical CorporationPittsburghUSA

Personalised recommendations