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Phenol process celebrates its 60th anniversary: The role of chemical principles in technological breakthroughs

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Abstract

This article provides an overview of the chemical principles of achieving the highest possible selectivity in the modern process of simultaneous phenol and acetone production on the basis of the achievements in technology developed by ILLA International, LLC, that has been successfully implemented in many plants all over the world. The article also demonstrates solutions by which the ILLA’s process has the potential to become virtually wasteless.

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References

  1. Nemtsov, M.S., Vospominaniya i razmyshleniya (Memories and Thoughts), St. Petersburg: RIO “SPb GIPT,” 2006, pp. 53–62.

    Google Scholar 

  2. Hock, H. and Lang, S., Berichte, 1944, vol. 77, nos. 3–4, pp. 257–264.

    Google Scholar 

  3. Stephens, H.N., J. Am. Chem. Soc., 1926, vol. 48, pp. 1824–1826.

    Article  CAS  Google Scholar 

  4. Stephens, H.N. and Roduta, F.L., J. Am. Chem. Soc., 1935, pp. 2380–2381.

  5. Kruzhalov, V.D. and Golovanenko, B.I., Sovmestnoe proizvodstvo fenola i acetone (Joint Phenol and Acetone Production), Moscow: Goskhimizdat, 1963.

    Google Scholar 

  6. Zakoshansky, V.M., Phenol and Acetone: An Analysis of the Process Technologies, and of the Kinetics and the Mechanisms of Corresponding Major Reactions, St. Petersburg: Khimizdat, 2009.

    Google Scholar 

  7. Emanuel, N.M., Denisov, E.T., and Maizus, Z.K., Tsepnye reaktsii okisleniya uglevodorodov v zhidkoi faze (Chain Oxidation Reactions of Hydrocarbons in Liquid Phase), Moscow: Nauka, 1965.

    Google Scholar 

  8. Knorre, D.G., et al., Usp. Khim., 1957, vol. 26, no. 4, pp. 416–458.

    CAS  Google Scholar 

  9. George, P. and Robertson, A., Trans. Faraday. Soc., 1946, vol. 42, nos. 3–4, pp. 217–229.

    Article  CAS  Google Scholar 

  10. Emanuel, N.M. and Gal, D., Okislenie etilbenzola. Modelnaya reaktsiya (Oxidation of Ethylbenzene. A Model Reaction), Moscow: Nauka, 1984.

    Google Scholar 

  11. Zakoshansky, V.M., et al., Abstract of Papers, Proc. of AIChE 1st Int. Aromatics Producers Conf., New Orleans, La., March 10–14, 2002, pp. 131–138.

  12. Zakoshansky, V.M. and Budarev, A.V., Ros. Khim. Zh., 2008, vol. 52, no. 4, pp. 72–88.

    Google Scholar 

  13. Zakoshansky, V.M. and Budarev, A.V., Ros. Khim. Zh., 2008, vol. 52, no. 6, pp. 152–168.

    Google Scholar 

  14. Antonovsky, V.L. and Makalets, B.I., Dokl. Akad. Nauk SSSR, 1961, vol. 140, no. 5, pp. 1070–1072.

    Google Scholar 

  15. Zakoshansky, V.M., Griaznov, A.K., and Vasilieva, I.I., High Selective Method of Phenol and Acetone Production, US Patent no. 6 057 483, 2000.

  16. Zakoshansky, V.M., Fedoseyev, F.G., Karasev, V.N., Eigin, S.V., Anfinogenova, T.S., and Moskovich, Yu.L., Method for Joint Phenol, Acetone, and α-Methylstyrene Production, 1987, RF Patent no. 1361937.

  17. Moskovich, Yu.L., Eigin, S.V., Zakoshansky, V.M., et al., Method for Joint Phenol, Acetone, and α-Methylstyrene Production, RF Patent 1391030, 1987.

  18. Zakoshansky, V.M., Moskovich, Yu.L., Gurfein, N.S., et al., Method for Joint Phenol, Acetone, and α-Methylstyrene Production, RF Patent no. 1563181, 1990.

  19. Zakoshansky, V.M., Method for the Decomposition of Cumene Hydroperoxide by Acidic Catalyst to Phenol and Acetone, US Patent no. 5 254 751, 1993.

  20. Griaznov, A.K. et al., Method for Automatic Control over a Cumene Hydroperoxide Cleavage Process, RF Patent no. 1699135, 1991.

  21. Yuriev Yu.N. and Zakoshansky V.M., Abstracts of Papers, Proc. of the Conf. on the Phenol and Acetone production “Regularities of Acidic Cumene Hydroperoxide Decomposition Reaction,” Novokuibyshevsk, 1982, pp. 73–74.

  22. Zakoshansky, V.M., Griaznov, A.K., and Vasilieva, I.I., Highly Selective Method for the Production of Phenol and Acetone from Cumene, RF Patent no. 2142932, 1999.

  23. Zakoshansky, V.M., Vasilieva, I.I., Griaznov, A.K., Yuriev, Yu.N., van Barnefeld, H., Gerlich, O., Kleine-Boymann, M., Kleinloh, W., and Michalic, C., Process for the Production of Phenol and Acetone from Cumene, US Patent no. 6 225 513, 2001.

  24. Zakoshansky, V.M., Vasilieva, I.I., Griaznov, A.K., Youriev, Yu.N., van Barnefeld, H., Gerlich, O., Kleine-Boymann, M., Kleinloh, W., and Michalic, C., Improved Method for Producing Phenol and Acetone from Cumol, EP Patent no. 0944567, 1999.

  25. Zakoshansky, V.M., Kataliz v promyshlennosti, 2004, no. 5, pp. 3–24.

  26. Zakoshansky, V.M., Abstracts of Papers, Proc. of AIChE 3rd Int. Conf. on Aromatics and Derivatives Formation of Key by-Products in Phenol Production Process, New Orleans, La., April 25–29, 2004, pp. 504–512.

  27. Zakoshansky, V.M., Zh. Obshch. Khim., 1989, vol. 59, no. 5, pp. 1122–1126.

    Google Scholar 

  28. Zakoshansky, V.M. et al., in Neftepererabotka i neftekhimiya: Collected works by CNIITEneftekhim, Moscow: CNIITEneftekhim, 1989, pp. 182–187.

    Google Scholar 

  29. Chulkov, V.P., Zakoshansky, V.M., et al., in Neftepererabotka i neftekhimiya: Collected works by CNIITEneftekhim, Moscow: CNIITEneftekhim, 1989, pp. 187–192.

    Google Scholar 

  30. Vasilieva, I.I., Zakoshansky, V.M., and Koshelev, Yu.N., in Neftepererabotka i neftekhimiya: Collected works by CNIITEneftekhim, no. 12, 2009, pp. 34–38.

  31. Vasilieva, I.I., Zakoshansky, V.M., and Koshelev, Yu.N., Abstracts of Papers, Proc. of the 13th Int. Sci. and Techn. Conf. “Reaktiv-2000,” Tula: TPGU, 2000, pp. 215–216.

    Google Scholar 

  32. Vasilieva, I.I., Zakoshansky, V.M., Koshelev, Yu.N., and Chulkov, V.P., Zh. Obshch. Khim., 2001, vol. 74, no. 1, pp. 107–110.

    Google Scholar 

  33. Zakoshansky, V.M., Kataliz v promyshlennosti, 2002, no. 1, pp. 29–41.

  34. Zakoshansky, V.M., Neftekhimiya, 2007, vol. 47, no. 4, pp. 301–313.

    Google Scholar 

  35. Zakoshansky, V.M., Artemov, A.V., and Antonovsky, V.L., Current State and Means of Intensification of Phenol and Acetone Production by Cumene Method: Topical Review, Ser. Neftepererabotka i slantsepererabotka, issue 6, Moscow: CNIITEneftekhim, 1988.

    Google Scholar 

  36. Zakoshansky, V.M., Kataliz v promyshlennosti, 2002, no. 5, pp. 9–22.

  37. Zakoshansky, V.M., Dobrotvorsky, A.M., Pinson, V.V., and Chulkov, V.P., Zh. Obshch. Khim., 1986, vol. 56, no. 3, pp. 665–670.

    Google Scholar 

  38. VNIINEFTEKHIM Research Institute. “Development of a Cumene Hydroperoxide Cleavage Process in an Acetone-Excessive Medium,” Report prepared by VNIINEFTEKHIM Research Institute, Leningrad, 198.

  39. Marshall Jr., B.K., De Caria, A.J., Hertzog, R.R., Sifniades, S., and Fisher, W.B., Decomposition of Cumene Oxidation Product, US Patent no. 7166752, 2007.

  40. Zakoshansky, V.M., Yuriev, Yu.N., Idlis, G.S., and Aleksandrov, A.S., Zh. Fiz. Khim., 1984, vol. 58, no. 5, pp. 1265–1267.

    Google Scholar 

  41. Kislina, I.S. et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1992, no. 1, pp. 72–77.

  42. Maiorov, V.D. et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, no. 5, pp. 1001–1006.

  43. Zakoshansky, V.M., in Protsessy neftepererabotki i neftekhimii: Collected works by VNIINeftekhim, St. Petersburg: GIORD, 2005, pp. 108–131.

    Google Scholar 

  44. Zakoshansky, V.M., Griaznov, A.K., Vasilieva, I.I., et al., Utility-Saving and Highly Selective Method for Preparing Phenol and Acetone, RF Patent no. 2141938, 1999.

  45. Sifniades, S., Tunick, A.A., and Koff, F.W., Decomposition of Cumene Oxidation Product, US Patent no. 4 358 618, 1982.

  46. Hood, H.E., Process for Producing Phenol from Cumene, US Patent 5 430 200, 1995.

  47. Hood, H.E., Process for Producing Phenol from Cumene, US Patent no. 5371 305, 1994.

  48. Blackborn, R.L., Allan, E.D., Le, L.B., and Patel, S., Cumene Hydroperoxide Cleavage Process, US Patent no. 5 463 136. 1995.

  49. Yasaka, N. and Shirahata, T., Process for the Production of Phenol, US Patent no. 5 998 677, 1999.

  50. Schmidt, R.J., Schulz, R.C., Bullen, P.J., et al., Decomposition of Cumene Hydroperoxide, US Patent no. 7 141 700, 2006.

  51. Schmidt, R.J., Schulz, R.C., Bullen, P.J., et al., Decomposition of Cumene Hydroperoxide, US Patent no. 7 141 701, 2006.

  52. Karnozhitsky, V., Organicheskie perekisi (Organic Peroxides), Moscow: Inostrannaya Literatura, 1961.

    Google Scholar 

  53. Zakoshansky, V.M. and Vassilieva, I.I., Method of Purifying Cumene Hydroperoxide Decomposition Products from Hydroxyacetone and from Other Carbonyls, US Patent no. 6 066 767, 2000.

  54. Zakoshansky, V.M., Vasilieva, I.I., and Koshelev, Yu.N., Abstracts of Papers, Proc. of AIChE 3rd Int. Aromatics Conf. on Aromatics and Derivatives, New Orleans, La., April 25–29, 2004, pp. 483–490.

  55. Koshelev, Yu.N., Zakoshansky, V.M., Vasilieva, I.I., and Malov, Yu.I., Method for Removal of Impurities from Penol, RF Patent no. 2266275, 2005.

  56. Zakoshansky, V.M., Malinovsky, A.S., Tsederbaum, V.G., et al., Method for Removing Organic Impurities from Phenol, RF Patent no. 2111203, 1998.

  57. Zakoshansky, V.M., Vasilieva, I.I., and Griaznov, A.K., Method for Purification of Phenol, US Patent no. 5 502 259, 1996.

  58. Schmidt, R.J. et al., Abstracts of Papers, Proc. of AIChE 7th Int. Conf. on Refinery Processing, New Orleans, La., April 25–29, 2004, pp. 49–503.

  59. Blackborn, R.L., Allan, E.D., Le, L.B., and Patel, S., Cumene Hydroperoxide Cleavage Process, US Patent no. 5 463 136, 1995.

  60. Gabutdinov, M.S., Kalashnikov, Ju.S., Shafigullin, A.S., et al., Method of Decomposing Cumene Hydroperoxide with Acid Catalyst to Phenol and Acetone, RF Patent no. 2114816, 1998.

  61. Zakoshansky, V.M. and Vasilieva, I.I., Wasteless Economic Method of Production of Phenol and Acetone, US Patent no. 6 252 124, 2001.

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  1. ILLA International, LLC, 4756 Doncaster Court, Long Grove, IL, 60047-6929, USA

    V. Zakoshansky

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  1. V. Zakoshansky
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Correspondence to V. Zakoshansky.

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Zakoshansky, V. Phenol process celebrates its 60th anniversary: The role of chemical principles in technological breakthroughs. Russ J Gen Chem 79, 2244–2266 (2009). https://doi.org/10.1134/S1070363209100260

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