Metathesis of olefins on metal oxides

Metal Oxides: Chemistry and Applications

Volumn , Issue , 2005, Pages 517-541

  Fierro, J L G ^a   Mol, J C ^b  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

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EID: 85128440855     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (111)

1. Banks, R.L. and Bailey, G.C. Olefin disproportionation - Anew catalytic process. Ind. Eng. Chem. Prod. Res. Develop. 1964, 3, 170-174.
2. Mol, J.C. Industrial applications of olefin metathesis. J. Mol. Catal. A: Chem. 2004, 213, 39-45.
3. Parkinson, G. Integration's the word in petrochemicals. Chem. Eng. 2001, 108, 27-35.
4. Bartlett, B., Hossain, M., and Tysoe, W.T. Reaction pathway and stereoselectivity of olefin metathesis at high temperature. J. Catal. 1998, 176, 439-447.
5. Dinger, M.B. and Mol, J.C. High turnover numbers with ruthenium-based metathesis catalysts. Adv. Synth. Catal. 2002, 344, 671-677.
6. Ivin, K.J. and Mol, J.C. Olefin Metathesis and Metathesis Polymerization. Academic Press, London, 1997.
7. Chaumont, P. and John, C.S. Olefin disproportionation technology (FEAST). A challenge for process development. J. Mol. Catal. 1988, 46, 317-328.
8. Mol, J.C. Application of olefin metathesis in the oleochemistry: an example of green chemistry. Green Chem. 2002, 4, 5-13.
9. Mol, J.C. Catalytic metathesis of unsaturated fatty acid esters and oils. Top. Catal. 2004, 27, 97-104.
10. Novak, B.M., Risse, W., and Grubbs, R.H. The development of well-defined catalysts for ring-opening olefin metathesis polymerization (ROMP). Adv. Polym. Sci. 1992, 102, 47-72.
11. Schrock, R.R. In Metathesis Polymerization of Olefins and Polymerization of Alkynes Imamoglu, Y., Ed. Kluwer, Dordrecht, 1998, Chap. 1, pp. 1-27.
12. Buchmeiser, M.R. Homogeneous metathesis polymerization by well-defined group VI and group VIII transition-metal alkylidenes: fundamentals and applications in the preparation of advanced materials. Chem. Rev. 2000, 100, 1565-1604.
13. Choi, S.H., Gal, Y.S., Jin, S.H., and Kim, H.K. Poly(1, 6-heptadiyne)-based materials by metathesis polymerization. Chem. Rev. 2000, 100, 1645-1681.
14. Schrock, R.R. In Ring-Opening Polimerization, Brunelle, D.J., Ed. Hanser, Munich, 1993, pp. 129.
15. Grubbs, R.H. and Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54, 4413-4450.
16. Phillips, A.J. and Abell, A.D. Ring-closing metathesis of nitrogen-containing compounds: applications to heterocycles, alkaloids, and peptidomimetics. Aldrich Chim. Acta 1999, 32, 75-89.
17. Wright, D.L. Application of olefin metathesis to organic synthesis. Curr. Org. Chem. 1999, 3, 211-340.
18. Fürstner, A. Olefin metathesis and beyond. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
19. Schuster, M. and Blechert, S. Olefin metathesis in organic chemistry. Angew. Chem. Int. Ed. 1997, 36, 2036-2056.
20. Schrock, R.R. and Hoveyda, A.H. Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts. Angew. Chem. Int. Ed. 2003, 42, 4592-4633.
21. Hoveyda, A.H. and Schrock, R.R. Catalytic asymmetric olefin metathesis. Chem. Eur. J. 2001, 7, 945-950.
22. Casey, C.P., Tuinstra, H.E., and Saemen, M.C. Reactions of (CO)5WC(Tol)2 with alkenes. A model for structural selectivity in olefin metathesis reaction. J. Am. Chem. Soc. 1976, 98, 608-609.
23. Casey, C.P., Burkhardt, T.J., Bunnell, C.A., and Calabrese, J.C. Synthesis and crystal structure of diphenylcarbene(pentacarbonyl)tungsten(0). J. Am. Chem. Soc. 1977, 99, 2127-2134.
24. Katz, T.J. and Rothchild, R. Mechanism of olefin metathesis of 2, 2'-divinylphenyl. J. Am. Chem. Soc. 1976, 98, 2519-2526.
25. Katz, T.J. and McGinnis, J. Metathesis of cyclic and acyclic olefins. J. Am. Chem. Soc. 1977, 99, 1903-1912.
26. Schrock, R.R. Multiple metal-carbon bonds. 5. Reaction of niobium and tantalum neopentylidene complexes with carbonyl function. J. Am. Chem. Soc. 1976, 98, 5399-5400.
27. Mol, J.C. Metathesis of functionalized acyclic olefins. J. Mol. Catal. 1991, 65, 145-162.
28. Mol, J.C. Olefin metathesis over supported rhenium oxide catalysts. Catal. Today 1999, 51, 289-299.
29. Mol, J.C. Olefin metathesis over supported rhenium oxide catalysts. Catal. Today 1999, 52, 377.
30. Sibeijn, M., Spronk, R., van Veen, J.A.R., and Mol, J.C. IR studies of Re2O7 metathesis catalysts supported on alumina and phosphated alumina. Catal. Lett. 1991, 8, 201-208.
31. Vuurman, M., Stufkens, D.J., Oskam, A., and Wachs, I.E. Structural determination of surface rhenium oxide on various oxide supports (Al2O3, ZrO2,TiO2, and SiO2). J. Mol. Catal. 1992, 76, 263-285.
32. Hietala, J., Root, A., and Knuuttila, P. The surface acidity of pure and modified aluminas in Re/Al2O3 metathesis catalysts as studied by 1H-NMR spectroscopy and its importance in the ethenolysis of 1, 5-cyclooctadiene. J. Catal. 1994, 150, 46-55.
33. Spronk, R., Van Veen, J.A.R., and Mol, J.C. The effect of the calcination temperature on the activity of Re2O7/γ-Al2O3 catalysts for the metathesis of propene. J. Catal. 1993, 144, 472-483.
34. Xiaoding, Xu and Mol, J.C. Re2O7/SiO2-Al2O3-SnR4 or -PbR4, a highly active catalyst for the metathesis of functionalized alkenes. J. Chem. Soc., Chem. Commun. 1985, 631-633.
35. Xiaoding, Xu, Boelhouwer, C., Benecke, J.I., Vonk, D., and Mol, J.C. Re2O7/Al2O3.B2O3 metathesis catalysts. J. Chem. Soc., Faraday Trans. 1 1986, 82, 1945-1953.
36. Sheu, F.C., Hong, C.T., Hwang, W.L., Shih, C.J., Wu, J.C., and Yeh, C.T. Propylene metathesis over Re2O7/Al2O3 •B2O3 catalysts. Catal. Lett. 1992, 14, 297-304.
37. Mol, J.C. and Andreini, A. Activity and selectivity of rhenium-based catalysts for alkene metathesis. J. Mol. Catal. 1988, 46, 151-156.
38. Andreini, A., Xu, X., and Mol, J.C. Activity of Re2O7/SiO2.Al2O3 catalysts for propene metathesis and the influence of alkyltin promoters. Appl. Catal. 1986, 27, 31-40.
39. Fridman, R.A., Nosakova, S.M, Liberov, G., and Bashkirov, A.N. Disproportionation of olefins on aluminum-molybdenum and aluminum-rhenium catalysts, promoted by tin tetraalkyl derivatives. Izv. Akad. Nauk. SSSR, Ser. Khim. 1977, 26, 678-679.
40. Mol, J.C. Metathesis of unsaturated fatty-acid esters and fatty oils. J. Mol. Catal. 1994, 90, 185-199.
41. Moloy, K.G. Evidence for intrinsically distinct active-sites on rhenium-based metathesis catalysts - Norbornene metathesis with Re2O7/Al2O3. J. Mol. Catal. 1994, 91, 291-302.
42. McCoy, J.R. and Farona, M.F. Olefin metathesis over a Re2O7/Al2O3 metathesis catalyst - Mechanism for initial metallacarbene formation. J. Mol. Catal. 1991, 66, 51-58.
43. Williams, K.P.J. and Harrison, K. Raman-spectroscopic studies of the effects of tin promotion on a rhenium alumina dismutation catalyst. J. Chem. Soc., Faraday Trans. 1990, 86, 1603-1606.
44. Xu, X., Andreini, A., and Mol, J.C. The role of SnR4 compounds in the metathesis of alkenes catalyzed by Re2O7/γ-Al2O3: An ESR study. J. Mol. Catal. 1985, 28, 133-140.
45. Buffon, R., Schuchardt, U., and Abras, A. Mössbauer and solid-state NMR spectroscopic studies of tin-modified rhenium-based metathesis catalysts. J. Chem. Soc., Faraday Trans. 1995, 91, 3511-3517.
46. Buffon, R., Jannini, M.J.D.M., and Abras, A. Effects of the addition of Nb2O5 to rhenium-based olefin metathesis catalysts. J. Mol. Catal. A: Chem. 1997, 155, 173-181.
47. Spronk, R., Andreini, A., and Mol, J.C. Deactivation of rhenium-based catalysts for the metathesis of propene. J. Mol. Catal. 1991, 65, 219-235.
48. Mol, J.C. and Wachs, I. Unpublished results.
49. Marvey, B.B., du Plessis, J.A.K., Vosloo, H.C.M., and Mol, J.C. Metathesis of unsaturated fatty acid esters derived from South African sunflower oil in the presence of a 3 wt% Re2O7/SiO2-Al2O3/SnBu4 catalyst. J. Mol. Cat. A: Chem. 2003, 201, 297-308.
50. Herrmann, W.A., Wagner, W., Flessner, U.N., Volkhardt, U., and Komber, H. Methyltrioxorhenium as catalyst for olefin metathesis. Angew. Chem., Int. Ed. Engl. 1991, 30, 1636-1638.
51. Morros, L.J., Downs, A.J., Greene, T.M., McGrady, G.S., Herrmann, W.A., Sirsch, P., Scherer, W., and Gropen, O. Matrix photochemistry of methyltrioxorhenium(VII), CH3ReO3: formation of the methylidene tautomer H2C=Re(O)2OH and its potential relevance to olefin metathesis. Organometallics 2001, 20, 2344-2352.
52. Chabanas, M., Coperet, C., and Basset, J.M. Re-based heterogeneous catalysts for olefin metathesis prepared by surface organometallic chemistry: reactivity and selectivity. Chem. Eur. J. 2003, 9, 971-975.
53. Xu, X.D., Mol, J.C., and Boelhouwer, C. Surface acidity of some Re2O7-containing metathesis catalysts - An in situ Fourier Transform infrared study using pyridine adsorption. J. Chem. Soc., Faraday Trans. I 1986, 82, 2707-2718.
54. Schekler-Nahama, F., Clause, O., Commereuc, D., and Saussey, J. Influence of Lewis acidity of rhenium heptoxide supported on alumina catalyst on the catalytic performances in olefin metathesis. Appl. Catal. A: Gen. 1998, 167, 237-245.
55. Buffon, R., Marochio, I.J., Rodella, C.B., and Mol, J.C. Germanium and silicon compounds as promoters for Re2O7/SiO2-Al2O3 metathesis catalysts. J. Mol. Cat. A: Chem. 2002, 190, 171-176.
56. Amigues, P., Chauvin, Y., Commereuc, D., Hong, C.T., Lai, C.C., and Lin, Y.H. Metathesis of ethylene-butene mixtures to propylene with rhenium on alumina catalysts. J. Mol. Catal. 1991, 65, 39-50.
57. Moulijn, J.A. and Mol, J.C. Structure and activity of rhenium-based metathesis catalysts. J. Mol. Catal. 1988, 46, 1-14.
58. Spronk, R. and Mol, J.C. Regeneration of rhenium-based catalysts for the metathesis of propene. Appl. Catal. 1991, 76, 143-152.
59. Engelhardt, J., Goldwasser, J., and Hall, W.K. The isomerization and metathesis of n-butenes IV. Reactions of cis-2-butene over a molybdena-alumina catalyst of varying extents of reduction. J. Mol. Catal. 1982, 15, 173-185.
60. Thomas, R. and Moulijn, J.A. A comparative study of γ-alumina supported molybdenum and tungsten oxide; relation between metathesis activity and reducibility. J. Mol. Catal. 1982, 15, 157-172.
61. Grünert, W., Stakheev, A.Y., Feldhaus, R., Anders, K., Shipro, E.S., and Minachev, Kh.M. Reduction and metathesis activity of MoO3/Al2O3 catalysts II. The activation of MoO3/Al2O3 catalysts. J. Catal. 1992, 135, 287-299.
62. Handzlik, J. and Ogonowski, J. Activity of molybdena-alumina metathesis catalysts treated with tetramethyltin. Catal. Lett. 2002, 83, 287-290.
63. Thomas, R., Moulijn, J.A., de Beer, V.H.J., and Medema, J. Structure/metathesis-activity relations of silica supported molybdenum and tungsten oxide. J. Mol. Catal. 1980, 8, 161-174.
64. Ono, T., Anpo, M., and Kubokawa, Y. Metathesis activity and structure of MoO3 highly dispersed on SiO2. Chem. Express 1986, 1, 181-184.
65. Ono, T., Anpo, M., and Kubokawa, Y. Catalytic activity and structure of molybdenum trioxyde highly dispersed on silica. J. Phys. Chem. 1986, 90, 4780-4784.
66. Shelimov, B.N., Elev, I.V., and Kazansky, V.B. Use of photoreduction for activation of silica-molybdena catalysts for propylene metathesis: comparison with thermal reduction. J. Catal. 1986, 98, 70-81.
67. Mol, J.C. Activity and stability of laser-photoreduced supported molybdenum oxide metathesis catalysts. Catal. Lett. 1994, 23, 113-118.
68. Shelimov, B.N., Elev, I.V., and Kazansky, V.B. Spectroscopic study of formation of active metal-carbene species in photoreduced silica-molybdena catalysts for olefin metathesis. J. Mol. Catal. 1988, 46, 187-200.
69. Elev, I.V., Shelimov, B.N., and Kazansky, V.B. Study of the mechanism of the reaction of metathesis of olefins and the formation of active sites on photoreduced molybdenum-silica catalysts. Kinet. Kataliz 1989, 30, 895-900.
70. Vikulov, K.A., Shelimov, B.N., Kazansky, V.B., and Mol, J.C. The deactivation mechanism of photoreduced and cyclopropane-treated molybdena/silica catalysts for olefin metathesis. J. Mol. Catal. 1994, 90, 61-67.
71. Van Schalkwyk, C., Spamer, A., Moodley, D.J., Dube, T., Reynhardt, J., and Botha, J.M. Application of a WO3/SiO2 catalyst in an industrial environment: part I. Appl. Catal. A: Gen. 2003, 255, 121-131.
72. Spamer, A., Dube, T.I., Moodley, D.J., van Schalkwyk, C., and Botha, J.M. Application of a WO3/SiO2 catalyst in an industrial environment: part II. Appl. Catal. A: Gen. 2003, 255, 133-142.
73. Factors that could influence the activity of a WO3/SiO2 catalyst: part III. Appl. Catal. A: Gen. 2003, 255, 143-152.
74. Andreini, A. and Mol, J.C. Activity of supported tungsten oxide catalysts for the metathesis of propene. J. Colloid Interface Sci. 1981, 84, 57-65.
75. Basrur, A.G., Patwardhan, S.R., and Vyas, S.N. Propene metathesis over silica-supported tungsten oxide catalyst - Catalyst induction mechanism. J. Catal. 1991, 127, 86-95.
76. Andreini, A. and Mol, J.C. Activity of supported tungsten oxide catalysts for the metathesis of propene. J. Chem. Soc., Faraday Trans. 1 1985, 81, 1705-1714.
77. Ahn, H.G., Yamamoto, K., Nakamura, R., and Niiyama, H. A novel metathesis catalyst consisting of non-transition elements - The metathesis of alkenes over tetramethyltin dehydroxylated alumina. Chem. Lett. 1992, (3), 503-506.
78. Yoshida, Y., Kimura, K., Inaki, Y., and Hattori, T. Catalytic activity of FSM-16 for photometathesis of propene. Chem. Commun. 1997, (1), 129-130.
79. Tanaka, T., Matsuo, S., Maeda, T., Yoshida, H., Funabiki, T., and Yoshida, S. Olefin metathesis over UV-irradiated silica. Appl. Surf. Sci. 1997, 121, 296-300.
80. Jannini, M.J.D.M., Buffon, R., de Wit, A.M., and Mol, J.C. Metathesis of terminal olefins over tin-modified silica-alumina. J. Mol. Catal. A: Chem. 1998, 133, 201-203.
81. Nédez, C., Théolier, A., Lefebvre, F., Choplin, A., Basset, J.M., and Joly, J.F. Surface organometallic chemistry of tin - Reactivity of tetraalkyltin complexes and tributyltin hydride toward silica. J. Am. Chem. Soc. 1993, 115, 722-729.
82. Nédez, C., Lefebvre, F., Choplin, A., Niccolai, G.P., Basset, J.M., and Benazzi, E. Surface organometallic chemistry of tin - reaction of hydridotris(butyl)tin with the surface of partially dehydroxylated aluminas. J. Am. Chem. Soc. 1994, 116, 8638-8646.
83. Buffon, R., Jannin, M.J.D.M., Abras, A., Mol, J.C., de Wit, A.M., and Kellendonk, F.J.A. Olefin metathesis overtin-modified non-transition metal oxides. J. Mol. Catal. A: Chem. 1999, 149, 275-282.
84. Anselme, G., Ranaivonjatovo, H., Escudié, J., Couret, C., and Satgé, J. A stable compound with a formal tin carbon double-bond - The bis(2, 4, 6-triisopropylphenyl) (fluorophenylidene) stannate. Organometallics 1992, 11, 2748-2750.
85. Adams, C.T. and Brandenberger, S.G. Mechanism of olefin disproportionation. J. Catal. 1969, 13, 360-367.
86. Katz, T.J. and Hersch, W.H. Stereochemistry of olefin metathesis reaction. Tetrahedron. Lett. 1977, 6, 585-588.
87. Tebbe, F.N., Parshall, G.W., and Ovenall, D.W. Titanium-catalyzed olefin metathesis. J. Am. Chem. Soc. 1979, 102, 5074-5075.
88. Wengrovius, J.H., Schrock, R.R., Churchill, M.R., Missert, J.R., and Youngs, W.J. Multiple metal-carbon bonds. 16. Tungsten-oxo alkylidene complexes as olefin metathesis catalysts and the crystal structure of W(O)(CHCMe3)(PEt3)Cl2. J. Am. Chem. Soc. 1980, 102, 4515-4516.
89. Howard, T.R., Lee, J.B., and Grubbs, R.H. Titanium metallacarbene- metallacyclobutane reactions: stepwise metathesis. J. Am. Chem. Soc. 1980, 102, 6876-6878.
90. McQuillin, F.J. and Powell, K.C. Stereoselectivity in the carbonyl insertion reaction between tetracarbonyldichlorodirhodium and substituted cyclopropanes. J. Chem. Soc., Dalton Trans. 1972, 19, 2129-2133.
91. Millman, W.S., Crespin, M., Cirrillo, A.C., Jr., Abdo, S., and Hall, W.K. Studies of the hydrogen held by solids. XXII. The surface chemistry of reduced molybdena- alumina catalysts. J. Catal. 1979, 60, 404-416.
92. Bartlett, B.F. and Tysoe, W.T. Molybdenum metal catalyzed reaction of ethene. Catal. Lett. 1997, 44, 37-42.
93. Clark, A. and Cook, C. Mechanism of propylene disproportionation. J. Catal. 1969, 15, 420-427.
94. Hughes, W.B. Kinetics and mechanism of homogeneous olefin disproportionation reaction. J. Am. Chem. Soc. 1969, 92, 532-539.
95. Crain, D.L. Mechanism of olefin disproportionation. J. Catal. 1969, 13, 110-118.
96. Biefeld, G.C., Eick, H.A., and Grubbs, R.H. Crystal structure of bis(triphenylphosphine) tetramethyleneplatinum(II). Inorg. Chem. 1973, 12, 2166-2170.
97. Wang, L.P., Millman, W.S., and Tysoe, W.T. The hydrogenation of CO over molybdenum/alumina in the presence of ethylene: coupling of olefin metathesis and CO hydrogenation. Catal. Lett. 1988, 1, 159-167.
98. Kazuta, M. and Tanaka, K. Synthesis of active sites for alkene metathesis reaction on molybdenum oxide films by reaction with alkylidene radicals. Catal. Lett. 1988, 1, 7-10.
99. Vikulov, K.A., Elev, I.V., Shelimov, B.N., and Kazansky, V.B. First IR spectroscopic observation of the stable Mo=CH2 carbene complex on the surface of an active catalyst for olefin metathesis - photoreduced silica-molybdena with chemisorbed cyclopropane. Catal. Lett. 1989, 2, 121-124.
100. Tanaka, K. Catalysts working by self-activation. Appl. Catal. A: Gen. 1999, 188, 37-52.
101. Kazuta, M. and Tanaka, K. Synthesis of active-sites for alkene metathesis reaction on molybdenum- and tungsten-oxide films. J. Catal. 1990, 123, 164-172.
102. Kazuta, M. and Tanaka, K. Preparation of very active molybdenum oxide films for use in the alkene metathesis reaction. J. Chem. Soc., Chem. Commun. 1987, (8), 616-617.
103. Tanaka, K., Tanaka, H., Takeo, H., and Matsumura, C. Intermediates forthe degenerate and productive metathesis of propene elucidated by the metathesis reaction of (Z)-propene-1-d1. J. Am. Chem. Soc. 1987, 109, 2422-2425.
104. Folga, E. and Ziegler, T. Density functional-study on molybdacyclobutane and its role in olefin metathesis. Organometallics 1993, 12, 325-337.
105. Fox, H.H., Schofield, M.H., and Schrock, R.R. Electronic structure and Mo(VI) alkylidene complexes and an examination of reactive intermediates using the SCF-XA-SW method. Organometallics 1994, 13, 2804-2815.
106. Aagaard, O.M., Meier, R.J., and Buda, F. Ruthenium-catalyzed olefin metathesis: a quantum molecular dynamics study. J. Am. Chem. Soc. 1998, 120, 7174-7182.
107. Adhart, C., Hinderling, C., Baumann, H., and Chen, P. Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry. J. Am. Chem. Soc. 2000, 122, 8204-8214.
108. Handzlik, J. and Ogonowski, J. Theoretical study on ethene metathesis proceeding on MoVI and MoIV methylidene centers of heterogeneous molybdena-alumina catalysts. J. Mol. Catal. A: Chem. 2001, 175, 215-225.
109. Van Santen, R.A. The cluster approach to molecular heterogeneous catalysis. J. Mol. Catal. A: Chem. 1997, 115, 405-419.
110. Handzlik, J. and Ogonowski, J. DFT study of ethene metathesis proceeding on monomeric MoVI centres of MoO3/Al2O3 catalyst: the role of the molybdacyclobutane intermediate. J. Mol. Catal. A: Chem. 2002, 184, 371-377.
111. Handzlik, J. Theoretical study of propene metathesis proceeding on monomeric Mo centers of molybdena-alumina catalysts. J. Catal. 2003, 220, 23-34.