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Abstract

The conversion of alcohols to hydrocarbons, especially to low molecular weight olefins, is not novel. Small-scale units (2000–10,000 t/yr) for production of ethylene from ethanol were common up to the 1960’s. However, the availability and low cost of natural gas and naphtha have shifted the feedstock away from ethanol to these materials, as well as favored large-scale olefin production (100,000–500,000 t/yr) through thermal cracking of hydrocarbons. In fact, the low price of these petrochemical olefins rendered feasible the reverse process: the production of the corresponding alcohols via catalytic hydration of these olefins.

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References

  1. J. P. Leonard and L. H. Weiss, Energ. Prog., 1:41 (1981).

    CAS  Google Scholar 

  2. H. Bahrmann, W. Lipps, and B. Cornils, Chem. Ztg., 106:249 (1982).

    CAS  Google Scholar 

  3. O. Winter and M. T. Eng, Hydrocarbon Process., 55(11):125 (1976).

    Google Scholar 

  4. N. K. Kochar and R. L. Marcell, Chem. Eng., 87(2):80 (1980).

    CAS  Google Scholar 

  5. N. R. Luchi and S. C. Trindade, Hydrocarbon Process., 61(5):179 (1982).

    Google Scholar 

  6. S. Fathi-Afshar and D. F. Rudd, Biotechnol. Bioeng., 22:677 (1980).

    Article  CAS  Google Scholar 

  7. B. O. Palsson, S. Fathi-Afshar, D. F. Rudd, and E. N. Lightfoot, Science, 213:513 (1981).

    Article  CAS  Google Scholar 

  8. E. S. Lipinsky, Science, 213:1465 (1981).

    Article  Google Scholar 

  9. N. Bondt, J. R. Deiman, P. van Troostwyk, and A. Lauwerenburg, Ann, chim. et phys., 21:48 (1797).

    Google Scholar 

  10. M. E. Winfield, in “Catalysis” (P. H. Emmett, ed.), Reinhold, New York, Vol. VII, 93 (1960).

    Google Scholar 

  11. S. A. Miller, “Ethylene and Its Industrial Derivatives,” Ernest Benn Limited, London, p 68 (1969).

    Google Scholar 

  12. N. K. Kochar, R. Merims, and A. S. Padia, Chem. Eng. Prog., 77(6):66 (1981).

    CAS  Google Scholar 

  13. H. V. Barracos, C. M. Da Silva, R. C. DeAssis, Ger. Offen. 2,834,699 (Feb. 22, 1979 ); assigned to Petroleo Brasileir S. A., PETROBRAS.

    Google Scholar 

  14. U. Tsao and H. B. Zasloff, U.S. Patent 4,134,926 (Jan. 16, 1979); assigned to LuMmus Co.

    Google Scholar 

  15. U. Tsao and J. W. Reilly, Hydrocarbon Process., 57(2):133 (1978).

    Google Scholar 

  16. H. Knözinger, Angew. Chem., 80:778 (1968).

    Article  Google Scholar 

  17. H. Knözinger, in “The Chemistry of the Hydroxyl Group” (S. Patal, ed.), Wiley-Interscience, London, Part II, p 641 (1971).

    Google Scholar 

  18. B. Notari, Chim. Ind. (Milan), 51:1200 (1968).

    Google Scholar 

  19. J. M. Winterbottom, in “Catalysis (Specialist Periodical Report),” C. Kemball and D. A. Dowden, ed., The Royal Society of Chemistry, London, Vol. IV, p. 141 (1981).

    Google Scholar 

  20. H. Vinek, H. Noller, M. Ebel, and K. Schwarz, J. Chem. Soc., Faraday Trans. 1, 73:734 (1977).

    Article  CAS  Google Scholar 

  21. H. Noller and K. Thomke, J. Mol. Catal., 6:375 (1979).

    Article  CAS  Google Scholar 

  22. N. Noller and W. Kladnig, Catal. Rev.-Sci. Eng., 13:149 (1976).

    Article  CAS  Google Scholar 

  23. I. Carrizosa and G. Munuera, J. Catal., 49:189 (1977).

    Article  CAS  Google Scholar 

  24. S. Siddhan and K. Narayanan, J. Catal., 59:405 (1979).

    Article  CAS  Google Scholar 

  25. V. A. Dzis’ko, M. S. Borisova, N. V. Akimova, and A. D. Makarov, Kinet. Catal., 5:681 (1964).

    Google Scholar 

  26. L. Beranek, Catal. Rev.-Sci. Eng., 16:1 (1977).

    Article  CAS  Google Scholar 

  27. M. Ai and S. Suzuki, Bull. Chem. Soc. Japan, 46:321 (1973).

    Article  CAS  Google Scholar 

  28. M. Ai, J. Catal., 40:318 (1975).

    Article  CAS  Google Scholar 

  29. M. Ai, Bull. Chem. Soc. Japan, 49:1328 (1976).

    Article  CAS  Google Scholar 

  30. M. Ai, J. Catal., 49:313 (1977).

    Article  CAS  Google Scholar 

  31. K. R. Bakshi and G. R. Gavalas, J. Catal., 38:312 (1975).

    Article  CAS  Google Scholar 

  32. K. R. Bakshi and G. R. Gavalas, J. Catal., 38:326 (1975).

    Article  CAS  Google Scholar 

  33. M. Balikova and L. Beranek, Collect. Czech. Chem. Commun., 42:2352 (1977).

    CAS  Google Scholar 

  34. J. Sedlacek, J. Catal., 57:208 (1979).

    Article  CAS  Google Scholar 

  35. W. S. Brey and K. A. Krieger, J. Am. Chem. Soc., 71:3637 (1949).

    Article  CAS  Google Scholar 

  36. K. W. Toptshieva and B. W. Romanarsky, Kinet. Katal., 6:279 (1965).

    Google Scholar 

  37. J. B. Butt, H. Bliss, and C. A. Walker, AIChE J., 8:42 (1962).

    Article  CAS  Google Scholar 

  38. J. M. Parera, Ind. Eng. Chem., Prod. Res. Dev., 15:234 (1976).

    Article  CAS  Google Scholar 

  39. J. B. Peri, J. Phys. Chem., 69:220 (1965).

    Article  CAS  Google Scholar 

  40. F. Figueras, L. de Mourgues, and Y. Trambouze, J. Catal., 14:107 (1969).

    Article  Google Scholar 

  41. J. R. Jain and C. N. Pillai, J. Catal., 9:322 (1967).

    Article  CAS  Google Scholar 

  42. J. E. Dabrowski, J. B. Butt, and H. Bliss, J. Catal., 18:297 (1970).

    Article  CAS  Google Scholar 

  43. H. Knözinger and A. Scheglila, Z. phys. Chem., Neue Folge, 63:197 (1969).

    Article  Google Scholar 

  44. H. Knözinger and H. Stolz, Ber. Bunsenges. Phys. Chem., 74:1056 (1970).

    Google Scholar 

  45. V. Jiratova and L. Beranek, Appl. Catal., 2:125 (1982).

    Article  CAS  Google Scholar 

  46. H. Knözinger and R. Köhne, J. Catal., 5:264 (1966).

    Article  Google Scholar 

  47. J. E. Stauffer and W. L. Kranich, Ind. Eng. Chem., Fundam., 1:107 (1962)

    Article  CAS  Google Scholar 

  48. H. J. Solomon, H. Bliss, and J. B. Butt, Ind. Eng. Chem., Fundam. 6:325 (1967).

    Article  CAS  Google Scholar 

  49. P. K. Gupta and M. Ravindram, Hung. J. Ind. Chem., 6:115 (1978).

    CAS  Google Scholar 

  50. H. Knözinger, K. Kochloefl, and W. Meye, J. Catal., 28:69 (1973).

    Article  Google Scholar 

  51. W. J. Hatcher, Jr. and L. Y. Sadler III, J. Catal., 38:73 (1975).

    Article  CAS  Google Scholar 

  52. L. de Mourgues, F. Peyron, Y. Trambouze, and M. Prettre, J. Catal., 7:117 (1966).

    Google Scholar 

  53. L. de Mourgues, D. Barthomeuf, F. Figueras, M. Perrin, Y. Trambouze, and M. Prettre, Proc. Int. Congr. Catal., 4th, 2:187 (1971).

    Google Scholar 

  54. W. S. Brey, Jr., B. H. Davis, P. G. Schmidt, and C. G. Moreland, J. Catal., 3:303 (1964).

    Article  CAS  Google Scholar 

  55. B. H. Davis and W. S. Brey, Jr., J. Catal., 25:81 (1972).

    Article  CAS  Google Scholar 

  56. A. J. Lundeen and R. van Hoozer, J. Am. Chem. Soc., 85:2180 (1963).

    Article  CAS  Google Scholar 

  57. A. J. Lundeen and R. van Hoozer, J. Org. Chem., 32:3386 (1967).

    Article  CAS  Google Scholar 

  58. P. Canesson and M. Blanchard, J. Catal., 42:205 (1976).

    Article  CAS  Google Scholar 

  59. K. Thomke, Z. phys. Chem., Neue Folge, 105:75 (1977).

    Article  CAS  Google Scholar 

  60. K. Thomke, Z. phys. Chem., Neue Folge, 105:87 (1977).

    Article  CAS  Google Scholar 

  61. K. Arata and H. Sawamura, Bull. Chem. Soc., Japan, 48:3377 (1975).

    Article  CAS  Google Scholar 

  62. B. H. Davis and P. Ganeson, Ind. Eng. Chem., Prod. Res. Dev., 18:191 (1979).

    Article  CAS  Google Scholar 

  63. T. Takeshita, R. Ohnishi, and K. Tanabe, Catal. Rev., 8:29 (1974).

    Article  Google Scholar 

  64. T. Yamagushi and K. Tanabe, Bull. Chem. Soc., Japan, 47:424 (1974).

    Article  Google Scholar 

  65. I. Mochida, A. Kato, and T. Seiyama, J. Catal., 22:23 (1971).

    Article  CAS  Google Scholar 

  66. J. B. Moffat, Catal. Rev.-Sci. Eng., 18:199 (1978).

    Article  CAS  Google Scholar 

  67. L. K. Freidlin, V. Z. Sharf, and Z. T. Tukhtamuradov, Kinet. Katal. 5:347 (1964).

    CAS  Google Scholar 

  68. J. B. Moffat and A. S. Riggs, J. Catal., 28:157 (1973).

    Article  CAS  Google Scholar 

  69. J. B. Moffat and A. S. Riggs, J. Catal., 42:388 (1976).

    Article  CAS  Google Scholar 

  70. H. Knözinger, H. Buehl, and E. Ress, J. Catal., 12:121 (1968).

    Article  Google Scholar 

  71. A. Tada and K. Mizushima, Nippon Kagaku Kaishi, 278 (1972).

    Google Scholar 

  72. S. S. Jewur and J. B. Moffat, J. Catal., 57:167 (1979).

    Article  CAS  Google Scholar 

  73. J. Haber and U. Szybalska, Discuss. Faraday Soc., 72:263 (1981).

    Article  Google Scholar 

  74. C. L. Kibby and W. K. Hall, J. Catal., 29:144 (1973).

    Article  CAS  Google Scholar 

  75. A. Tada and M. Yoshida, Nippon Kagaku Kaishi, 856 (1973).

    Google Scholar 

  76. A. Tada, M. Yoshida, and M. Hirai, Nippon Kagaku Kaishi, 1379 (1973).

    Google Scholar 

  77. S. Kikkawa, Y. Shimizu, and S. Higuchi, Chem. Lett., 849 (1979).

    Google Scholar 

  78. Y. Ono, T. Mori, and T. Keii, Proc. Int. Congr. Catal., 7th., p 1414 (1981).

    Google Scholar 

  79. Y. Ono and T. Mori, J. Chem. Soc., Faraday Trans I, 77:2209 (1981).

    Article  CAS  Google Scholar 

  80. Y. Ono, T. Baba, J. Sakai, and T. Keil, J. Chem. Soc., Chem. Commun., 400 (1981).

    Google Scholar 

  81. T. Okuhara, A. Kasai, N. Hayakawa, M. Misono, and Y. Yoneda, Chem. Lett., 391 (1981).

    Google Scholar 

  82. N. Hayakawa, T. Okuhara, M. Misono, and Y. Yonada, Nippon Kagaku Kaishi, 356 (1982).

    Google Scholar 

  83. R. Rudham and A. Stockwell, in “Catalysis (Specialist Periodical Reports),” C. Kemball, ed., The Chemical Society, London, Vol. 1, p 87 (1977).

    Google Scholar 

  84. M. S. Spencer and T. V. Whittam, in “Catalysis (Specialist Periodical Report),” C. Kemball and D. A. Dowden, ed., The Chemical Society, London, Vol. 3, p 189 (1980).

    Google Scholar 

  85. D. Barthomeuf, Stud. Surf. Sci. Catal., 5 (Catalysis by Zeolites), Elsevier, Amsterdam, p 55 (1980).

    Google Scholar 

  86. N. Y. Chen, J. Phys. Chem., 80:60 (1976).

    Article  CAS  Google Scholar 

  87. D. H. Olson, W. O. Haag, and R. M. Lago, J. Catal., 61:390 (1980).

    Article  CAS  Google Scholar 

  88. E. M. Flanigen, J. M. Bennett, R. W. Grose, J. P. Cohen, R. L. Patton, R. M. Kirchner, and J. V. Smith, Nature (London), 271:512 (1978).

    Article  CAS  Google Scholar 

  89. M. Ralek and O. Grubner, Proc. Int. Congr. Catal., 3rd, 1302 (1965).

    Google Scholar 

  90. E. G. Derouane, J. B. Nagy, P. Dejaifve, J. H. C. van Hooff, B. P. Spekman, J. C. Vedrine, and C. Naccache, J. Catal., 53:40 (1978).

    Article  CAS  Google Scholar 

  91. V. J. Frilette, W. O. Haag, and R. M. Lago, J. Catal., 67:218 (1981).

    Article  Google Scholar 

  92. S. L. Meisel, J. P. McCullough, C. H. Lechthaler, and P. B. Weisz, Chemtech, 6:86 (1976).

    CAS  Google Scholar 

  93. C. D. Chang and A. J. Silvestri, J. Catal., 47:249 (1977).

    Article  CAS  Google Scholar 

  94. C. D. Chang, W. H. Lang, and R. Smith, J. Catal., 56:169 (1979).

    Article  CAS  Google Scholar 

  95. N. Y. Chen and W. J. Reagan, J. Catal., 59:123 (1979).

    Article  CAS  Google Scholar 

  96. Y. Ono and T. Mori, J. Chem. Soc., Faraday Trans. I, 77:2209 (1981).

    Article  CAS  Google Scholar 

  97. P. Dejaifve, J. C. Vedrine, V. Bolis, and E. G. Derouane, J. Catal., 63:331 (1980).

    Article  CAS  Google Scholar 

  98. J. R. Anderson, T. Mole, and V. Christov, J. Catal., 61:477 (1980).

    Article  CAS  Google Scholar 

  99. W. W. Kaeding and S. A. Butter, J. Catal., 61:155 (1980).

    Article  CAS  Google Scholar 

  100. P. G. Rodewald, U.S. Patent 4,700,219 (July 11, 1978); assigned to Mobil Oil Corp.

    Google Scholar 

  101. Y. Matsumura, K. Hashimoto, S. Watanabe, and S. Yoshida, Chem. Lett., 121 (1981).

    Google Scholar 

  102. J. C. Oudejans, P. F. van den Oosterkamp, and H. van Bekkum, Appl. Catal., 3:109 (1982).

    Article  CAS  Google Scholar 

  103. R. A. Rajadhyaksha and J. R. Anderson, J. Catal., 63:510 (1980).

    Article  CAS  Google Scholar 

  104. E. N. Givens, C. J. Plank, and E. J. Rosinski, U.S. Patent 4,079,095 (March 14, 1978); assigned to Mobil Oil Corp.

    Google Scholar 

  105. F. A. Wunder and E. I. Leupold, Angew. Chem., 92:125 (1980).

    Article  CAS  Google Scholar 

  106. U. Dettmeier, H. Litterer, H. Baltes, W. Herzog, E. I. Leupold, and F. A. Wunder, Chem. Ing. Tech., 54:590 (1982).

    Article  CAS  Google Scholar 

  107. F. A. Wunder, E. I. Leupold, and H. Litterer, Eur. Pat. Appl. EP 43 494 (Jan. 13, 1982 ).

    Google Scholar 

  108. T. Inui, T. Ishihara, N. Morinaga, G. Takeuchi, E. Araki, T. Kanie, and Y. Takegami, Nippon Kagaku Kaishi, 221 (1982).

    Google Scholar 

  109. T. Inui, E. Araki, T. Sezume, T. Ishihara, and Y. Takegami, React. Kinet. Catal. Lett., 18:1 (1981).

    Article  CAS  Google Scholar 

  110. S. T. Wilson, B. M. Lok, C. A. Messina, T. R. Cannan, and E. M. Flanigen, J. Am. Chem. Soc., 104:1146 (1982).

    Article  CAS  Google Scholar 

  111. K. Jerabek, L. Baranek, and K. Setinek, Proc. Int. Congr. Catal., 5th, 2:1193 (1973).

    CAS  Google Scholar 

  112. A. Martinec, K. Setinek, and L. Beranek, J. Catal. 51:86 (1978).

    Article  CAS  Google Scholar 

  113. K. M. Dooley, J. A. Williams, B. C. Gates, and R. L. Albright, J. Catal., 74:361 (1982).

    Article  CAS  Google Scholar 

  114. R. B. Diemer, K. M. Dooley, B. C. Gates, and R. L. Albright, J. Catal., 74:373 (1982).

    Article  CAS  Google Scholar 

  115. R. Thornton and B. C. Gates, J. Catal., 34:275 (1974).

    Article  CAS  Google Scholar 

  116. B. C. Gates, J. S. Wisnouskas, and H. W. Heath, Jr., J. Catal., 24:320 (1972).

    Article  CAS  Google Scholar 

  117. C. A. Cooper, R. L. McCullough, B. C. Gates, and J. C. Seferis, J. Catal., 63:372 (1980).

    Article  CAS  Google Scholar 

  118. R. L. Kabel and L. N. Johanson, AIChE J., 8:621 (1962).

    Article  CAS  Google Scholar 

  119. S. P. Sivanand, B. V. Kamath, R. S. Singh, and D. K. Chakrabarty, J. Catal., 69:502 (1981).

    Article  CAS  Google Scholar 

  120. V. L. Magnotta, B. C. Gates, and G. C. A. Schuit, J. Chem. Soc., Chem. Commun., 342 (1976).

    Google Scholar 

  121. V. L. Magnotta and B. C. Gates, J. Catal., 46:266 (1974).

    Article  Google Scholar 

  122. T. J. Huang and S. Yurchak, U.S. Patent 3,855,343 (Dec. 17, 1974); assigned to Mobil Oil Corp.

    Google Scholar 

  123. G. A. Olah, J. Kaspi, and J. Bukala, J. Org. Chem., 42:4187 (1977).

    Article  CAS  Google Scholar 

  124. D. E. Pearson, J. Chem. Soc., Chem. Commun., 397 (1974).

    Google Scholar 

  125. D. E. Pearson, U.S. Patent 4,133,838 (Jan. 9, 1979); assigned to Pearson Research Corp.

    Google Scholar 

  126. D. E. Pearson, J. S. Sawyer, and J. H. Cleveland, Ind. Eng. Chem., Prod. Res. Dev., 19:245 (1980).

    Article  CAS  Google Scholar 

  127. D. E. Pearson, R. D. Tanner, I. D. Picciotto, J. S. Sawyer, and J. H. Cleveland, Jr., Ind. Eng. Chem., Prod. Res. Dev., 20:734 (1981).

    Article  CAS  Google Scholar 

  128. E. Cherbuliez, C. Gandillon, A. DePicciotto, and J. Rabinowitz, Helv. Chim. Acta, 42:2277 (1959).

    Article  CAS  Google Scholar 

  129. M. I. Vinnik and P. A. Obraztsov, Kinet. Katal., 19:239 (1978).

    CAS  Google Scholar 

  130. E. K. Jones, Adv. Catal., 8:219 (1956).

    Article  CAS  Google Scholar 

  131. A. G. Oblad, G. A. Mills, and H. Heinemann, in “Catalysis” (P. H. Emmett, ed.), Reinhold, New York, Vol. VI, p 341 (1958).

    Google Scholar 

  132. R. G. Downing and D. E. Pearson, J. Am. Chem. Soc., 83:1718 (1961)

    Article  CAS  Google Scholar 

  133. G. A. Olah, A. P. Fung, and D. Meidar, Synthesis, 280 (1981).

    Google Scholar 

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Kut, O.M., Tanner, R.D., Prenosil, J.E., Kamholz, K. (1984). Catalytic Conversion of Alcohols to Olefins. In: Herman, R.G. (eds) Catalytic Conversions of Synthesis Gas and Alcohols to Chemicals. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2737-0_19

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