Chemistry, catalysts, and processes for isoparaffin-olefin alkylation: Actual situation and future trends

Catalysis Reviews

Volumn 35, Issue 4, 1993, Pages 483-570

  Corma, Avelino ^a   Martínez, Agustín ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ALKYLATION; CATALYSIS; CATALYSTS; CHEMICAL REACTORS; PARAFFINS; ZEOLITES;

LIQUID CATALYSTS; SOLID CATALYSTS;

OLEFINS;

EID: 0027868735     PISSN: 01614940     EISSN: 15205703     Source Type: Journal    
DOI: 10.1080/01614949308013916     Document Type: Article

References (141)

1. V.N. Ipatieff, A.V. Grosse, J. Am. Chem. Soc, 1935, 57-1616
2. W.L. Lafferty, R.W. Stokeld, Adv. Chem. Ser, 1971, 103-130
3. R.C. Weast, M.J. Astle, W.H. Beyer, Handbook of Chemistry and Physics, 1986, (eds.), 67th ed CRC Press, Boca Raton, FL
4. H.H. Hyman, M. Kilpatrick, J.J. Katz, J. Am. Chem. Soc, 1957, 79-3668
5. M.A. Paul, F.A. Long, Chem. Rev, 1957, 57-1
6. J.H. Simons, R.D. Dresdner, J. Am. Chem. Soc, 1944, 66-1070
7. C.A. Zimmerman, J.T. Kelly, J.C. Dean, Ind. Eng. Chem Prod. Res. Dev, 1962, 1-124
8. M.C. Simmons, T.R. Kelly, Gas Chromatogr, 1991, Second Int. Symp Academic Press, New York
9. M.H. Gorin, C.S. Kuhn, C.B. Miles, Ind. Eng. Chem, 1946, 38-795
10. E.J. Prosen, K.S. Pitzer, E.D. Rossini, J. Res. Natl. Bur. Stand, 1945, 34-255, 1641, (RP)
11. J.F. Mosby, L.F. Albright, Ind. Eng. Chem Prod. Res. Dev, 1966, 5-183
12. K.W. Li, R.E. Eckert, L.F. Albright, Ind. Eng. Chem Prod. Des. Dev, 1970, 9-434
13. C.R. Cupit, J.E. Gwyn, E.C. Jernigan, Petro/Chem. Eng, 1962, 34-49
14. UOP HF alkylation process, B.R. Shah, Handbook of Petroleum Refining Processes, 1986, (R. A. Meyers, Ed.), McGraw-Hill, New York, Part 1, 1.1
15. L. Schmerling, Chemistry of Petroleum Hydrocarbons, 1955, 3, in (B. T. Brooks et al eds.), Reinhold, New York
16. C.R. Cupit, J.E. Gwyn, E.C. Jernigan, Petro/Chem. Eng, 1961, 33-47
17. L.R. Durret, L.M. Taylor, C.F. Wantland, J. Dvoretzky, Anal. Chem, 1963, 35-67
18. L.F. Albright, K.E. Kranz, Prepr. Am. Chem. Soc. Div. Pet. Chem, 1991, New York City Meeting, August 25–30
19. L.F. Albright, M.A. Spalding, J. Faunce, R.E. Eckert, Ind. Eng. Chem Res, 1988, 27-91
20. S. Miron, R.J. Lee, J. Chem. Eng. Data, 1963, 8-150
21. L.F. Albright, Industrial and Laboratory Alkylations, 1977, 55, ACS Symp. Ser ACS, Washington, DC
22. F.C. Whitmore, J. Am. Chem. Soc, 1932, 54-3274
23. S.F. Birch, A.E. Dunstan, Trans. Faraday Soc, 1939, 35-1013
24. L. Schmerling, Ind. Eng. Chem, 1953, 45-1447
25. L. Schmerling, J. Am. Chem. Soc, 1944, 66-1472
26. L. Schmerling, J. Am. Chem. Soc, 1946, 68-275
27. P.D. Barlett, F.E. Condon, A. Schneider, J. Am. Chem. Soc, 1944, 66-1531
28. J.E. Hofman, J. Org. Chem, 1964, 29-3627
29. T. Hudson, G.E. Hays, Industrial and Laboratory Alkylations, 1977, 55, ACS Symp. Ser ACS, Washington, DC
30. R.J. Shlegeris, L.F. Albright, Ind. Eng. Chem Prod. Res. Dev, 1969, 8-92
31. J.E. Hofman, A.J. Schrieschein, J. Am. Chem. Soc, 1962, 84-953
32. L.F. Albright, L. Houle, A.M. Sumutka, L.E. Eckert, Ind. Eng. Chem Prod. Res. Dev, 1972, 11-446
33. T.D. Stewart, W.H. Calkinks, J. Am. Chem. Soc, 1948, 70-1006
34. B.M. Doshi, L.F. Albright, Ind. Eng. Chem. Process Des, 1975, 15-53
35. K.W. Li, R.E. Eckert, L.F. Albright, Ind. Eng. Chem Process Des. Dev, 1970, 9-441
36. L.F. Albright, B.M. Doshi, M.A. Ferman, A. Ewo, Industrial and Laboratory Alkylations, 1977, 55-96, ACS Symp. Ser
37. M. McCaulay, 1966, 3-280, 211, US Pat
38. N.C. Deno, Chem. Eng. News, 1964, October 5
39. D.H. Putney, Adv. Pet. Chem. Refin, 1959, 2-315
40. D.J. Am Ende, personal communication, 1990
41. E.K. Jones, Adv. Catal, 1958, 10-165
42. K. Kranz, 1989, report from Stratco Inc Leawood, Kan
43. J.O. Iverson, L. Schmerling, Adv. Pet. Chem. Refin, 1958, 1-336
44. A. Schneider, R.M. Kennedy, J. Am. Chem. Soc 73, 1951, 5013, 5017, 5024
45. L.E. Chapin, G.C. Liolios, T.M. Robertson, Hydroc. Proc, 1985, 67, September
46. H.V. Hammershaimb, B.R. Shah, Hydrocarbon Proc 73, 1985, June
47. NPRA Q&A—Conclusion, Oil Gas J, 1992, April 27
48. G.M. Kramer, J. Org. Chem, 1965, 26-2671
49. L.F. Albright, Oil Gas J, 1990, November 12
50. F.B. Sprow, Ind. Eng. Chem Process Des. Dev, 1969, 8-254
51. L. Lee, P. Harriott, Ind. Eng. Chem Process Des. Dev, 1977, 16-3
52. H. Lerno, V.A. Citarella, Hydrocarbon Process, 1991, November
53. L.F. Albright, Oil Gas J, 1990, November 26
54. R.L., van Zele, R. Diener, Hydrocarbon Process, 1990, 77, June July
55. K.R. Masters, E.A. Prohaska, Hydrocarbon Process, 1988, 48, August
56. L.F. Albright, B.M. Doshi, M.A. Ferman, A. Ewo, Industrial and Laboratory Alkylations, 1977, 55-109, ACS Symp. Ser
57. L.F. Albright, M.A. Spalding, J.A. Nowinski, R.H. Ybarra, R.E. Eckert, Ind. Eng. Chem Res, 1988, 27-381
58. L.F. Albright, M.A. Spalding, J.A. Nowinski, R.H. Ybarra, R.E. Eckert, Ind. Eng. Chem Res, 1988, 27-391
59. J.E. Sobel, 1975, US Patent 3928486
60. H.L. Hoffman, Hydrocarbon Process, 1991, February
61. Continuous isobutane-butene alkylation with zeolite catalysts, F.W. Kirsch, J.D. Potts, Prepr. Am. Chem. Soc Div. Pet. Chem, 1970, September
62. Reactivity and functionality of a zeolite alkylation catalyst, F.W. Kirsch, J.L. Lauer, J.D. Potts, Prepr. Am. Chem. Soc. Div. Pet. Chem, 1971, B24, March - April
63. F.W. Kirsch, J.D. Potts, D.S. Barmby, J. Catal, 1972, 27-142
64. W.E. Garwood, W.K. Leaman, C.G. Myers, C.J. Plank, 1966, 3251902, US Patent
65. P.D. Caesar, W.O. Haag, 1972, 3647916, US Patent
66. F.W. Kirsch, D.S. Barmby, J.D. Potts, 1974, 3839228, US Patent
67. C.H.L. Yang, 1975, 3893942, US Patent
68. T.J. Huang, S. Yurchak, Industrial and Laboratory Alkylations, 1977, 55-75, ACS Symposium Series
69. K.M. Minachev, E.S. Mortinov, S.M. Zen'kovski, N.V. Mostovoy, Industrial and Laboratory Alkylations, 1977, 55-89, ACS Symp. Ser
70. J. Weitkamp, Proc. Int. Conf. Zeolites, 1980, 5-858
71. Y.F. Chu, A.W. Chester, Zeolites, 1986, 6-195
72. A. Corma, M. Faraldos, A. Mifsud, Appl. Catal, 1989, 47-125
73. A. Corma, M. Faraldos, A. Martínez, A. Mifsud, J. Catal, 1990, 122-230
74. R.M. Kennedy, Catalysis, 1958, 6, 1, (P. H. Emmett ed.) Reinhold New York
75. C.R. Cupit, J.E. Gwyn, E.C. Jernigan, Petro/Chem. Eng, 1961, 204
76. L. Schmerling, Friedel-Crafts and Related Reactions, 1964, 2-2, 1075, (G. A. Olah ed.) Interscience New York
77. V.N. Ipatieff, L. Schmerling, Adv. Catal, 1948, 1-27
78. J. Weitkamp, Catalysis by Zeolites, 1980, 65, in (B. Imelik et-al ed.) Elsevier Amsterdam
79. J.A. Kovalinka, J.J. Sholten, J.C. Rasser, J. Catal, 1977, 48-365
80. G.A. Olah, Chem. Brit, 1972, 8-281
81. S.N. Khadzhiev, I.M. Gerzeliev, Prepr. ACS Pet. Div, 1991, 799, NY Meeting August
82. M. Daage, F. Fajula, Bull. Soc. Chim. Fran, 1984, 5-153
83. G.Y. Gardos, L. Péchy, A. Rédey, C.H. Okonji, Hung. J. Ind. Chem Veszprém, 1980, 8-363
84. G.Y. Gárdos, L. Péchy, A. Rédey, I. Sokorai, Hung. J. Ind. Chem Veszprém, 1980, 8-371
85. G.Y. Gárdos, A. Rédey, S. Kristof, Geterog. Katal, 1983, 5-447
86. W.M. Meier, D.H. Olson, Atlas of Zeolite Structure Types, 1987, 2nd ed Butterworths
87. C.H.L. Yang, 1974, 3851004, US Patent
88. P.E. Eberly, Jr., C.H.N. Kimberlin, 1974, 3840613, US Patent
89. C. Marcilly, J.F. Le Page, 1972, 2-210, 440, French Patent
90. J.E. Sobel, 1971, 3763261, US Patent
91. C.L. Thomas, 1970, 3541180, US Patent
92. Y. Matsunaga, Can. J. Chem, 1958, 37-994
93. T.J. Huang, 1983, 4384161, US Patent
94. M.M.J. Treacy, J.M. Newsam, Nature, 1988, 332-249
95. A. Corma, V. Fornés, F. Melo, J. Pérez-Pariente, Symp. Adv. FCC Preprints, 1987, ACS Petrol. Division New Orleans Meeting September
96. L. Boneto, M.A. Camblor, J. Pérez-Pariente, A. Corma, Appl. Catal, 1992, 82-37
97. J. Pérez-Pariente, E. Sastre, V. Fornés, J.A. Martens, P.A. Jacobs, A. Corma, Appl. Catal, 1991, 69-125
98. J.P. Gilson, J.M. Nanne, G.J. Den Otter Eur, 1990, 398415, Patent
99. N.A. Briscoe, J.L. Casci, J.A. Daniels, D.W. Jhonson, M.D. Shannon, A. Stewart, Stud. Surf. Sci. Catal., 1989, 151, (P. A. Jacobs and R. A. van Santen eds.) 49A
100. R.L. Wadlinger, G.T. Kerr, E.J. Rosinski, 1967, 3308069, US Patent
101. M.A. Camblor, A. Mifsud, J. Pérez-Pariente, Zeolites, 1991, 11-792
102. B. Juguin, F. Raatz, C. Marcilly, 1988, 2631956, French Patent
103. R.A. Innes, S.I. Zones, G.J. Nacamuli, 1990, 4891458, US Patent
104. A. Huss, Jr., G.W. Kirker, K.M. Keville, R.T. Thomson, 1991, 4992615, US Patent
105. T.S. Chou, A. Huss, Jr., C.R. Kennedy, R.S. Kurtas, 1990, World Patent 90/00533
106. J.E. Child, A. Huss, Jr., C.R. Kennedy, D.O. Marler, S.A. Tabak, 1991, 5012033, US Patent
107. A.K. Roebuck, B.L. Evering, Ind. Eng. Chem Prod. Res. Dev, 1970, 9-76
108. Y. Chauvin, D. Commerenc, A. Hirschauer, F. Hugues, L. Saussine, 1989, 2626572, French Patent
109. R.J. Gillespie, Acc. Chem. Res, 1968, 1-202
110. R. Bogoczek, J. Surowiec, Chem. Ing. Tech, 1987, 59-2
111. A. Krzywicki, M. Marczewski, S. Malinowski, React. KinetCatal. Lett, 1978, 8-25
112. G.A. Fuentes, J.V. Boegel, B.C. Gates, J. Catal, 1982, 78-436
113. H. Hattori, O. Takahashi, M. Takagi, K. Tanabe, J. Catal, 1981, 68-132
114. K. Tanabe, H. Hattori, Chem. Lett, 1976, 6-625
115. O. Takahashi, H. Hattori, J. Catal, 1981, 68-144
116. J.D. Kemp, 1974, 3852371, US Patent
117. J.D. Kemp, 1976, 3979476, US Patent
118. T.S. Chou, A. Huss, Jr., C.R. Kennedy, R.S. Kurtas, S.A. Tabak, World Patent 90/00534, 1990
119. J.E. Child, T.S. Chou, A. Huss, Jr., C.R. Kennedy, F.P. Ragonese, S.A. Tabak, 1990, 4956518, US Patent
120. Y. Ono, S. Sakuma, K. Tanabe, N. Kitajima, Chem. Lett, 1978, 1061
121. Y. Ono, K. Tanabe, N. Kitajima, Chem. Lett, 1978, 625
122. H.R. Appell, 1960, 2925447, US Patent
123. N.C. Neckers, D.A. Kooistra, W.G. Green, J. Am. Chem. Soc, 1972, 94-9284
124. B. Sket, M. Zupan, Macromol. Sci Part A, 1983, 19-643
125. V.L. Magnota, B.C. Gates, J. Sci. Polym. Chem. Ed, 1977, 15-1341
126. K.M. Dooley, B.C. Gates, J. Sci. Polym. Chem. Ed, 1984, 22-859
127. K. Kelley, 1958, 2843642, US Patent
128. T.J. Huang, S. Yurchak, 1974, 3855342, US Patent
129. J. Klein, H. Widdecke, Erdöl v. Kohle, 1983, 36-307
130. J. Surowiec, Chem. Ing. Tech, 1985, 57-884
131. D.L. King, H.D. Cooper, M.A. Faber, 1989, 4863343, US Patent
132. T. Yamaguchi, Appl. Catal, 1990, 61-1
133. T. Hosoi, T. Okada, S. Nojima, I. Imai, 1989, 01245853, Jpn. Patent
134. A. Kayo, T. Yamaguchi, K. Tanabe, J. Catal, 1983, 83-99
135. T. Yamaguchi, T. Jin, K. Tanabe, J. Phys. Chem, 1986, 90-3148
136. T. Jin, T. Okada, S. Nojima, T. Imai, 1989, 01245853, Jpn. Patent
137. S. Baba Y. Shibata H. Takaoka T. Kimura and K. Takasak Jpn. Patent 61153140 (1986).
138. F. W. Kirsch J. D. Potts and D. S. Barmby US Patent 3655813 (1972).
139. F. W. Kirsch D. S. Barmby and J. D. Potts US Patent 3706814 (1972).
140. T. L. Holmes and S. L. Thomson US Patent 3976713 (1976).
141. R. F. Zabranski and R. F. Anderson US Patent 4008291 (1977).