Butene oligomerization by phosphoric acid catalysis: Separating the effects of temperature and catalyst hydration on product selectivity

Industrial and Engineering Chemistry Research

Volumn 45, Issue 18, 2006, Pages 6127-6136

  De Klerk, Arno ^a   Leckel, Dieter O ^a   Prinsloo, Nicolaas M ^a  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; COMPOSITION; FISCHER-TROPSCH SYNTHESIS; HYDRATION; PHOSPHORIC ACID; POLYMERIZATION;

OLIGOMERIZATION; SOLID PHOSPHORIC ACID (SPA); TRIPHOSPHORIC ACID;

BUTENES;

BUTENES; CATALYSIS; CATALYST SELECTIVITY; COMPOSITION; FISCHER-TROPSCH SYNTHESIS; HYDRATION; PHOSPHORIC ACID; POLYMERIZATION;

EID: 33748764366     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie060207m     Document Type: Article

References (87)

1. Ipatieff, V. N.; Corson, B. B.; Egloff, G. Polymerization, a new source of gasoline. Ind. Eng. Chem. 1935, 27, 1077.
2. Egloff, G.; Morrell, J. C.; Nelson, E. F. Motor fuels from polymerization. Pet. Refin. 1937, 16, 497.
3. Leprince, P. Oligomerization. In Petroleum refining Vol. 3: Conversion processes; Leprince, P., Ed.; Editions Technip: Paris, 2001; p 321.
4. Dancuart, L. P.; De Haan, R.; De Klerk, A. Processing of primary Fischer-Tropsch products. Stud. Surf. Sci. Catal. 2004, 152, 482.
5. De Klerk, A.; Engelbrecht, D. J.; Boikanyo, H. Oligomerization of Fischer-Tropsch olefins: Effect of feed and operating conditions on hydrogenated motor-gasoline quality. Ind. Eng. Chem. Res. 2004, 43, 7449.
6. Weinert, P. C.; Egloff, G. Catalytic polymerization and its commercial application. Pet. Process. 1948, June, 585.
7. Langlois, G. E.; Walkey, J. E. Improved process polymerizes olefins for high-quality gasoline. Pet. Refin. 1952, 31 (8), 79.
8. McMahon, J. F.; Bednars, C.; Solomon, E. Polymerization of olefins as a refinery process. In Advances in Petroleum Chemistry and Refining; Kobe, K. A., McKetta, J. J., Eds.; Wiley: New York, 1963; Vol. 7, p 285.
9. Villadsen, J.; Livbjerg, H. Supported liquid-phase catalysts. Catal. Rev.-Sci. Eng. 1978, 17, 203.
10. Bell, R. N. Composition of strong phosphoric acids. Ind. Eng. Chem. 1948, 40, 1464.
11. Huthi, A.-L.; Gartaganis, P. A. The composition of the strong phosphoric acids. Can. J. Chem. 1956, 34, 785.
12. Ohashi, S.; Sugatani, H. The composition of strong phosphoric acids. Bull. Chem. Soc. Jpn. 1957, 30, 864.
13. Jameson, R. F. The composition of the "strong" phosphoric acids. J. Chem. Soc. 1959, 752.
14. Fontana, B. J. The vapor pressure of water over phosphoric acids. J. Am. Chem. Soc. 1951, 73, 3348.
15. Brown, E. H.; Whitt, C. D. Vapor pressure of phosphoric acids. Ind. Eng. Chem. 1952, 44, 615.
16. MacDonald, D. I.; Boyack, J. R. Density, electrical conductivity, and vapor pressure of concentrated phosphoric acid. J. Chem. Eng. Data 1969, 14, 380.
17. Cavani, F.; Girotti, G.; Terzoni, G. Effect of water in the performance of the "solid phosphoric acid" catalyst for alkylation of benzene to cumene and for oligomerisation of propene. Appl. Catal., A 1993, 97, 177.
18. Zhirong, Z.; Zaiku, X.; Yongfu, C.; Refeng, W.; Yaping, Y. Free phosphoric acid of diatomite-phosphate solid acid and its catalytic performance for propylene oligomerization. React. Kinet. Catal. Lett. 2000, 70, 379.
19. Prinsloo, N. M. Solid phosphoric acid oligomerisation: Manipulating diesel selectivity by controlling catalyst hydration. Fuel Process. Tecknol. 2006, 87, 437.
20. Bethea, S. R.; Karchmer, J. H. Propylene polymerization in packed reactor. Liquid phosphoric acid catalyst. Ind. Eng. Chem. 1956, 48, 370.
21. Krawietz, T. R.; Lin, P.; Lotterhos, K. E.; Torres, P. D.; Barich, D. H. ; Clearfield, A.; Haw, J. F. Solid phosphoric acid catalyst: A multinuclear NMR and theoretical study. J. Am. Chem. Soc. 1998, 120, 8502.
22. 2 catalyst. Kinet. Catal. 1989, 30, 974.
23. Ohtsuka, H.; Aomura, K. Activation of solid phosphoric acid by heat treatment. Bull. Jpn. Pet. Inst. 1962, 4, 3.
24. Egloff, G.; Weinert, P. C. Polymerisation with solid phosphoric acid catalyst. Proc. World Pet. Congr., 3rd 1951, 4, 201.
25. Ipatieff, V. N. Catalytic polymerization of gaseous olefins by liquid phosphoric acid. I. Propylene. Ind. Eng. Chem. 1935, 27, 1067.
26. De Jager, H.-J.; Heyns, A. M. Kinetics of acid-catalyzed hydrolysis of a polyphosphate in water. J. Phys. Chem. A 1998, 102, 2838.
27. Smith, J. P.; Brown, W. E.; Lehr, J. R. Structure of crystalline phosphoric acid. J. Am. Chem. Soc. 1955, 77, 2728.
28. Ross, W. H.; Jones, R. M. The solubility and freezing-point curves of hydrated and anhydrous orthophosphoric acid. J. Am. Chem. Soc. 1925, 47, 2165.
29. Munson, R. A. Self-dissociative equilibria in molten phosphoric acid. J. Phys. Chem. 1964, 68, 3374.
30. Munson, R. A. Kinetics of the ortho-pyro interconversion in 100% phosphoric acid. J. Phys. Chem. 1965, 69, 1761.
31. Thilo, E. Condensed phosphates and arsenates. Adv. Inorg. Chem. Radiochem. 1962, 4, 1.
32. Jameson, R. F. Polyphosphoric acid. I. Chemistry. In Phosphoric Acid; Slack, A. V., Ed.; Marcel Dekker: New York, 1968; pp 983-1006.
33. Van Wazer, J. R. Principles of phosphorus chemistry. I. Some generalities concerning multiple bonding. J. Am. Chem. Soc. 1956, 78, 5709.
34. Mabis, A. J.; Quimby, O. T. Analysis of sodium pyro- and tripolyphosphate mixtures by X-ray diffractometer using an internal standard. Anal. Chem. 1953, 25, 1814.
35. Van Wazer, J. R.; Griffith, E. J.; McCullough, J. F. Analysis of phosphorus compounds. Automatic pH titration of soluble phosphates and their mixtures. Anal. Chem. 1954, 26, 1755.
36. Corbridge, D. E. C.; Lowe, E. J. Quantitative infrared analysis of condensed phosphates. Anal. Chem. 1955, 27, 1383.
37. Higgins, C. E.; Baldwin, W. H. Dehydration of orthophosphoric acid. Anal. Chem. 1955, 27, 1780.
38. Callis, C. F.; Van Wazer, J. R.; Shoolery, J. N. Analysis of phosphorous compounds. Use of nuclear magnetic resonance spectra in differential determination of the oxyacids of phosphorus. Anal. Chem. 1956, 28, 269.
39. Guffy, J. C.; Miller, G. R. Nuclear Magnetic Resonance method for analysis of phosphoric acids. Anal. Chem. 1959, 31, 1895.
40. Beukenkamp, J.; Rieman, W.; Lindenbaum, S. Behavior of the condensed phosphates in anion-exchange chromatography. Anal. Chem. 1954, 26, 505.
41. Grande, J. A.; Beukenkamp, J. Gradient elution chromatography of phosphates. Anal. Chem. 1956, 28, 1497.
42. Shintani, H.; Dasgupta, P. K. Gradient anion chromatography with hydroxide and carbonate eluents using simultaneous conductivity and pH detection. Anal. Chem. 1987, 59, 802.
43. Stover, F. S.; Bulmahn, J. A.; Gard, J. K. Polyphosphate separations and chain length characterization using minibore ion chromatography with conductivity detection. J. Chromatogr., A 1994, 688, 89.
44. Baluyot, E. S.; Hartford, C. G. Comparison of polyphosphate analysis by ion chromatography and by modified end-group titration. Chromatogr., A 1996, 739, 217.
45. Svoboda, L.; Schmidt, U. Single-column ion chromatography of linear polyphosphates. J. Chromatogr., A 1997, 767, 107.
46. Sekiguchi, Y.; Matsunaga, A.; Yamamoto, A.; Inoue, Y. Analysis of condensed phosphates in food products by ion chromatography with an on-line hydroxide eluent generator. J. Chromatogr., A 2000, 881, 639.
47. Flory, P. J. Random reorganization of molecular weight distribution in linear condensation polymers. J. Am. Chem. Soc. 1942, 64, 2205.
48. Van Wazer, J. R. Structure and properties of the condensed phosphates. II. A theory of the molecular structure of sodium phosphate glasses. J. Am. Chem. Soc. 1950, 72, 644.
49. Parks, J. R.; Van Wazer, J. R. Structure and properties of the condensed phosphates. XII. Reorganization theory and some applications. J. Am. Chem. Soc. 1957, 79, 4890.
50. Bell, R. N. Hydrolysis of dehydrated sodium phosphates. Ind. Eng. Chem. 1947, 39, 136.
51. Friess, S. L. The energies of acid-catalyzed hydrolysis of triphosphoric and pyrophosphoric acids. J. Am. Chem. Soc. 1952, 74, 4027.
52. Campbell, D. O.; Kilpatrick, M. L. A kinetic study of the hydrolysis of pyrophosphates. J. Am. Chem. Soc. 1954, 76, 893.
53. Van Wazer, J. R.; Griffith, E. J.; McCullough, J. F. Structure and properties of the condensed phosphates. VII. Hydrolytic degradation of pyro-and tripolyphosphate. J. Am. Chem. Soc. 1955, 77, 287.
54. Osterheld, R. K. Kinetics of the aqueous reversion of pyrophosphate. J. Phys. Chem. 1958, 62, 1133.
55. Keisch, B.; Kennedy, J. W.; Wahl, A. C. The exchange of oxygen between phosphoric acid and water. J. Am. Chem. Soc. 1958, 80, 4778.
56. Abbot, G. A. The rate of hydration of pyrophosphoric acid in aqueous solution. J. Am. Chem. Soc. 1909, 31, 763.
57. Clapp, C. H.; Westheimer, F. H. Monomeric methyl metaphosphate. J. Am. Chem. Soc. 1974, 96, 6710.
58. Clapp, C. H.; Satterthwait, A.; Westheimer, F. H. Monomeric methyl metaphosphate. II. Electrophilic aromatic substitution. J. Am. Chem. Soc. 1975, 97, 6873.
59. Florián, J.; Warshel, A. Phosphate ester hydrolysis in aqueous solution: Associative versus dissociate mechanism. J. Phys. Chem. B1998, 102, 719.
60. Guthrie, J. P. Hydration and dehydration of phosphoric acid derivatives: Free energies of formation of the pentacoordinate intermediates for phosphate ester hydrolysis and of monomeric metaphosphate. J. Am. Chem. Soc. 1977, 99, 3991.
61. Westheimer, F. H. Pseudo-rotation in the hydrolysis of phosphate esters. Acc. Chem. Res. 1968, 1, 70.
62. Wróblewski, A. E.; Verkade, J. G. 1-Oxo-2-oxa-1-phosphabicyclo-[2.2.2]octane: A new mechanistic probe for the basic hydrolysis of phosphate esters. J. Am. Chem. Soc. 1996, 118, 10168.
63. Dejaegere, A.; Karplus, M. Hydrolysis rate difference between cyclic and acyclic phosphate esters: Solvation versus strain. J. Am. Chem. Soc. 1993, 115, 5316.
64. 31P NMR. J. Org. Chem. 2005, 70, 8303.
65. Mayes, P. A. Bioenergetics. In Harper's Review of Biochemistry, 19th ed. ; Martin, D. W., Jr., Mayes, P. A., Rodwell, V. W., Eds.; Lange Medical Publications: Los Altos, CA, 1983; pp 63-69.
66. Ipatieff, V. N.; Corson, B. B. Gasoline from ethylene by catalytic polymerization. Ind. Eng. Chem. 1936, 28, 860.
67. Deeter, W. F. Propene polymerization for motor-gasoline production. Oil Gas J. 1950, March 23, 252.
68. Ipatieff, V. N.; Schaad, R. E. Mixed polymerization of butenes by solid phosphoric acid catalyst. Ind. Eng. Chem. 1938, 30, 596,
69. ASTM DS 4B, Physical constants of hydrocarbons and non-hydrocarbon compounds, 2nd ed.; ASTM: Philadelphia, PA, 1991.
70. Schmerling, L.; Ipatieff, V. N. The mechanism of the polymerization of alkenes. In Advances in Catalysis and Related Subjects; Frankenburg, W. G., Komarewsky, V. I., Rideal, E. K., Eds.; Academic Press: New York, 1950; Vol. II, p 21.
71. De Klerk, A. Isomerization of 1-butene to isobutene at low temperature. Ind. Eng. Chem. Res. 2004, 43, 6325.
72. Ipatieff, V. N.; Pines, H. Alkylation accompanying depolymerization. J. Am. Chem. Soc. 1936, 58, 1056.
73. Buchanan, J. S.; Santiesteban, J. G.; Haag, W. O. Mechanistic considerations in acid-catalyzed cracking of olefins. J. Catal. 1996, 158, 279.
74. De Klerk, A. Reactivity differences of octenes over Solid Phosphoric Acid. Ind. Eng. Chem. Res. 2006, 45, 578.
75. CRC Handbook of Chemistry and Physics; Weast, R. C., Ed.; CRC Press: Boca Raton, FL, 1988; p D-103.
76. Langlois, G. E.; Walkey, J. E. An improved process for polymerization of olefins with phosphoric acid on quartz catalyst. Proc. World Pet. Congr., 3rd 1951, 4, 191.
77. Ipatieff, V. N.; Egloff, G. Polymer gasoline has higher blending value than pure iso-octane. Oil Gas J. 1935, May 16, 31.
78. Egloff, G. Polymer gasoline. Ind. Eng. Chem. 1936, 28, 1461.
79. Shanley, W. B.; Egloff, G. Midget Poly units. Oil Gas J. 1939, May 18, 116.
80. Dry, M. E. High yield high quality diesel from Fischer-Tropsch process. ChemSA 1984, 10, 286.
81. De Klerk, A. Distillate production by oligomerization of Fischer-Tropsch olefins over Solid Phosphoric Acid. Energy Fuels 2006, 20, 439.
82. Quann, R. J.; Green, L. A.; Tabak, S. A.; Krambeck, F. J. Chemistry of olefin oligomerization over ZSM-5 catalyst. Ind. Eng. Chem. Res. 1988, 27, 565.
83. O'Connor, C. T. Oligomerization. In Handbook of Heterogeneous Catalysis; Ertl, G., Knözinger, H., Weitkamp, J., Eds.; VCH: Weinheim, 1997; pp 2380-2387,
84. 10 to higher olefins over synthetic zeolite ZSM-5. ACS Symp. Ser. 1983, 218, 383.
85. Guisnet, M.; Magnoux, P. Organic chemistry of coke formation. Appl. Catal., A 2001, 212, 83.
86. Louw, E. Report: U232 low reactor temp test run; Sasol internal communication.
87. Terblans, J. C.; Khan, F.; Prinsloo, N. M. Unit 232 low reactor temperature test run; Sasol internal communication.