Expanded product, plus kinetic and mechanistic, studies of polyoxoanion-based cyclohexene oxidation catalysis: The detection of ∼70 products at higher conversion leading to a simple, product-based test for the presence of olefin autoxidation

Journal of Molecular Catalysis A: Chemical

Volumn 191, Issue 2, 2003, Pages 217-252

  Weiner, Heiko ^a   Trovarelli, Alessandro ^b   Finke, Richard G ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF UDINE   (Italy)

Author keywords

Catalysis with molecular oxygen; Cyclohexene autoxidation catalysis; Detection of autoxidation; Free radical chain mechanisms; Homogeneous catalysis; Kinetic and mechanistic studies; Oxidation catalysis; Polyoxoanions in catalysis

Indexed keywords

CATALYSIS; COMPLEXATION; GAS CHROMATOGRAPHY; OXIDATION; REACTION KINETICS; SOLVENTS; TRANSITION METALS;

CATALYST VARIATION;

OLEFINS;

2 CYCLOHEXEN 1 OL; 2 CYCLOHEXEN 1 YL HYDROPEROXIDE; 2 CYCLOHEXENONE; ALKENE; ANION; CHLORINATED HYDROCARBON; CYCLOHEXANE OXIDE; CYCLOHEXENE DERIVATIVE; FREE RADICAL; HYDROPEROXIDE; OXYGEN; POLYOXOANION; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHLORINATION; COMPLEX FORMATION; DERIVATIZATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; REACTION ANALYSIS;

EID: 0347721772     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(02)00344-8     Document Type: Article

References (162)

1. (a) R.A. Sheldon, J.K. Kochi, Metal catalyzed oxidations of organic compounds in liquid phase, Oxidation Combustion Rev. 5 (1973) 135;
2. (b) R.A. Sheldon, J.K. Kochi, Metal catalyzed oxidations of organic compounds in liquid phase: a mechanistic approach, Adv. Catal. 25 (1976) 272-413.
3. R.A. Sheldon, J.K. Kochi, Metal catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
4. (a) V.D. Luedecke Adipic Acid, in: J.J. McKetta, W.A. Cunningham (Eds.), Encyclopedia of Chemical Processing and Design, vol. 2, Marcel Dekker, New York, 1977, pp. 128-146;
5. (b) G.W. Parshall, S.D. Ittel (Eds.), Homogeneous Catalysis, Central Research and Development E.I. du Pont de Nemours and Company/Wiley, Wilmington/New York, 1992, pp. 283-264;
6. (c) B.C. Gates (Ed.), Catalytic Chemistry, Wiley, New York, 1992, p. 63.
7. (a) E.H. Farmer, A. Sundralingam, J. Chem. Soc. 121 (1942);
8. (b) J.L. Bolland, Q. Rev., Chem. Soc. 3 (1949) 1;
9. (c) D. Swern, J.E. Coleman, J. Am. Oil Chem. Soc. 32 (1955) 700;
10. (d) J.L. Skellon, Chem. Ind. (London) (1951) 629; (1953) 1047;
11. (d) J.L. Skellon, Chem. Ind. (London) (1951) 629; (1953) 1047;
12. (e) L. Bateman, L.Q. Rev., Chem. Soc. 8 (1954) 147;
13. (f) G.A. Russell, J. Chem. Educ. 36 (1959) 111;
14. (g) E.T. Denisov, N.M. Emanuel, Russ. Chem. Rev. 29 (1960) 6;
15. (h) W.O. Lundberg, Autoxidation and Antioxidants, vols. 1 and 2, Wiley, New York, 1962;
16. (i) N.M. Emanuel, Oxidation of Hydrocarbons in the Liquid Phase, Pergamon, Oxford, 1965, p. 45;
17. (j) G. Scott, Atmospheric Oxidation and Antioxidants, Elsevier, Amsterdam, 1965;
18. (k) I.V. Berezin, E.T. Denisov, N.M. Emanuel, The Oxidation of Cyclohexane, Pergamon, Oxford, 1965;
19. (l) N.M. Emanuel, E.T. Denisov, Z.K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum Press, New York, 1967;
20. (m) F.R. Mayo, Oxidation of Organic Compounds, Advance Chemical Series 75, 76, 77, American Chemical Society, Washington, DC, 1968;
21. (n) F.R. Mayo, Accts. Chem. Res. 1 (1968) 193;
22. (o) L. Reichand, S.S. Stivala, Autoxidation of Hydrocarbons and Polyolefins, Marcel Dekker, New York, 1969;
23. (p) E.S. Huyser, Free Radical-Chain Reactions, Wiley/Interscience, New York, 1970, p. 39;
24. (q) J. Betts, Q. Rev., Chem. Soc. 25 (1971) 265;
25. (r) W.G. Lloyd, Methods Free-Radical Chem. 4 (1973) 1;
26. (s) J.A. Howard, Free Radicals, vol. 2, Wiley, New York, 1973, p. 3;
27. (t) E.T. Denisov, N.I. Mitskevich, V.E. Agabekov, Liquid Phase Oxidation of Oxygen-Containing Compounds, Consultants Bureau, Plenum Press, New York, 1977;
28. (u) R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981;
29. (v) C.L. Hill (Ed.), Activation and Functionalization of Alkanes, Wiley/Interscience, New York, 1989, pp. 243-279;
30. (w) C.A. Tolmann, J.D. Druliner, M.J. Nappa, N. Herron, Alkane Oxidation Studies in du Pont's Central Research Department, Wiley/Interscience, New York, 1989, pp. 303-360;
31. (x) W. Partenheimer, Catal. Today 23 (1995) 69.
32. (a) F. Haber, J. Weiss, Naturwissenschaften 20 (1931) 948;
33. (b) V.P. Kurkov, J.Z. Pasky, J.B. Lavingo, J. Am. Chem. Soc. 90 (1968) 4743;
34. (c) W.F. Brill, B.J. Barone, J. Org. Chem. 29 (1964) 140;
35. (d) D.E. van Sickle, F.R. Mayo, R.M. Arluck, J. Am. Chem. Soc. 87 (1965) 4824. Note the mechanism in this paper for the formation of higher MW peroxidic products on p. 4827;
36. (e) D.E. van Sickle, F.R. Mayo, E.S. Gould, R.M. Arluck, J. Am. Chem. Soc. 89 (1967) 977;
37. (f) M. Koelewijn, Recl. Trav. Chim. Pays-Bas 91 (1972) 759;
38. (g) F.R. Mayo, J. Am. Chem. Soc. 80 (1958) 2497;
39. (h) D.E. van Sickle, F.R. Mayo, R.M. Arluck, J. Am. Chem. Soc. 87 (1965) 4832;
40. (i) E.S. Gould, M. Rado, J. Catal. 13 (1969) 238;
41. (j) K. Kaneda, T. Itoh, Y. Fujiwara, S. Teranishi, Bull. Chem. Soc. Jpn. 46 (1973) 3810;
42. (k) R. Criegee, in: K. Wiberg (Ed.), Oxidations in Organic Chemistry, Academic Press, New York, 1965, p. 302;
43. (l) R. Criegee, H. Pilz, H. Flygare, Chem. Ber. 72 (1939) 1799;
44. (m) W.J. Brill, J. Am. Chem. Soc. 85 (1963) 141;
45. (n) A. Fusi, R. Ugo, F. Fox, A. Pasini, C. Cenini, J. Organomet. Chem. 26 (1971) 417. See p. 418 for a reference to non-volatile polymer products from cyclohexene autoxidation;
46. (o) J.E. Lyons, Tet. Lett. 32 (1974) 2737 (and references [1-7] therein to cyclohexene oxidation products including dimers and polymers);
47. (p) T. Mlodnicka, J. Mol. Catal. 36 (1986) 205;
48. (q) R.K. Jensen, S. Korcek, L.R. Mahoney, M. Zinbo J. Am. Chem. Soc. 101 (1979) 7574.
49. (a) C. Walling, Acc. Chem. Res. 31 (1998) 155;
50. (b) P.A. MacFaul, D.D.M. Wayner, K.U. Ingold, Acc. Chem. Res. 31 (1998) 159;
51. (c) M.W. Grinstaff, M.G. Hill, J.A. Labinger, H.B. Gray, Science 264 (1994) 1311;
52. (d)P.A. MacFaul, K.U. Ingold, D.D.M. Wayner, L. Que Jr., J. Am. Chem. Soc. 119 (1997) 10594;
53. (e) D.W. Snelgrove, P.A. MacFaul, K.U. Ingold, D.D.M. Wayner, Tet. Lett. 37 (1996) 823;
54. (f) P.A. MacFaul, I.W.C.E. Arends, K.U. Ingold, D.D.M. Wayner, J.C.S. Perkin Trans. 2 (1997) 135;
55. (g) F. Minisci, F. Fontana, S. Araneo, F. Recupero, S. Banfi, S. Quici, J. Am. Chem. Soc. 117 (1995) 226;
56. (h) F. Minisci, F. Fontana, S. Araneo, E Recupero, L. Zhao, SYNLET, 1996, p. 119;
57. (i) M. Newcomb, P.A. Simakov, S.-U. Park, Tet. Let. 37 (1996) 819;
58. (j) K.U. Ingold, P. MacFaul, in: B. Meunier (Ed.), Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Imperial College Press, 2000, Chapter 2, pp. 45-89.
59. C.L. Hill, C.M. Prosser-McCharta, Homogeneous catalysis by transition metal oxygen anion clusters, Coord. Chem. Rev. 143 (1995) 407.
60. (a) I.V. Kozhevnikov, Russ. Chem. Rev. 56 (1987) 811;
61. (b) Y. Ishii, M. Ogawa, in: S. Oae (Ed.), Reviews on Heteroatom Chemistry, MYU Tokyo, 1990, p. 121;
62. (c) M. Misono, N. Nojiri, Appl. Catal. 64 (1990) 1;
63. (d) C.L. Hill, in: G. Strukul (Eds.), Metal Catalysis in Hydrogen Peroxide Oxidations, Kluwer Academic Publishers, Dordrecht, 1992, Chapter 8, pp. 253-280;
64. (e) Y. Ono, in: J.M. Thomas, K.I. Zamaraev (Eds.), Perspective in Catalysis, Blackwell, Oxford, UK, 1992, pp. 431-464;
65. (f) V. Kozhevnikov, Usp. Khim. 62 (1993) 510;
66. (g) M. Misono, Stud. Surf. Sci. Catal. 75 (1993) 1;
67. (h) T. Okuhara, M. Misono, Yuki Gosei Kagaku Kyokaishi 51 (1993) 128;
68. (i) C.L. Hill, G.-S. Kim, C.M. Prosser-McCartha, D. Judd, Mol. Eng. 3 (1993) 263;
69. (j) M.H. Dickmann, M.T. Pope, Chem. Rev. 94 (1994) 569;
70. (k) R.J.J. Jansen, H.M. Vanveldhuizen, M.A. Schwegler, H. Vanbekkum, Recueil des travaux chimiques des pays bas, J. Royal Netherlands Chem. Soc. 113 (1994) 115;
71. (l) N. Mizuno, M. Misono, J. Mol. Cat. 86 (1994) 319.
72. (a) C. Venturello, R. D'Aloiso, J.C. Bart, M. Ricci, J. Mol. Catal. 32 (1985) 107;
73. (b) C. Venturello, M. Gambaro, Synthesis 4 (1989) 295;
74. (c) Y. Sakata, Y. Ishii, J. Org. Chem. 56 (1991) 6233;
75. (d) S. Sakaue, Y. Sakata, Y. Nishiyama, Y. Ishii, Chem. Lett. (1992) 289;
76. (e) L. Salles, C. Aubry, F. Robert, G. Chottard, R. Thouvenot, H. Ledon, J.-M. Brégault New, J. Chem. 17 (1993) 367;
77. (f) A.C. Dengel, W.P. Griffith, B.C. Parkin, J. Chem. Soc. Dalton Trans. (1993) 2683;
78. (g) L. Salles, C. Aubry, R. Thouvenot, F. Robert, C. Dorémieux-Morin, G. Chottard, H. Ledon, Y. Jeannin, J.-M. Brégeault, Inorg. Chem. 33 (1994) 871;
79. (h) F.P. Ballistreri, G.A. Tomaselli, R.M. Toscano, V. Conte, F. Difuria, J. Mol. Catal. 89 (1994) 295.
80. (a) J.E. Lyons, P.E. Ellis Jr., H.K. Myers Jr., G. Suld, W.A. Langdale, US Patent 4,803,187 (1989);
81. (b) N.I. Kuznetsova, E.N. Yurchenko, React. Kinet. Catal. Lett. 39 (1989) 399;
82. (c) D.E. Katsoulis, M.T. Pope, J. Chem. Soc., Dalton Trans. (1989) 1483;
83. (d) L.I. Kuznetsova, M.A. Fedotov, E.N. Yurchenko, React. Kinet. Catal. Lett. 41 (1990) 333;
84. (e) P.E. Ellis Jr., J.E. Lyons, U.S. Patent 4,898,989 (1990);
85. (f) M.A. Fedotov, O.M. Il'inich, L.I. Kuznetsova, G.L. Semin, Y.S. Vetchinova, K.I. Zamaraev, Catal. Lett. 6 (1990) 417;
86. (g) J.E. Lyons, P.E. Ellis Jr., V.A. Durante, in: R.A. Grasselli, A.W. Sleight (Eds.), Studies in Surface Science and Catalysis, Elsevier, Amsterdam, 1991, pp. 99-116;
87. (h) R. Neumann, M. Levin, in: L.I. Simandi (Ed.), Dioxygen Activation and Homogeneous Catalytic Oxidation, Elsevier, Amsterdam 1991, pp. 121-127;
88. (i) E.N. Yurchenko, T.D. Gutsul, L.I. Kuznetsova, Koord. Khim. 18 (1992) 939;
89. (j) N. Mizuno, M. Tateishi, T. Hirose, M. Iwamoto, Chem. Lett. (1993) 1985;
90. (k) N. Mizuno, T. Hirose, M. Tateishi, M. Iwamoto, Chem. Lett. (1993) 1839;
91. (l) N. Mizuno, T. Hirose, M. Tateishi, M. Iwamoto, J. Mol. Catal. 88 (1994) L125.
92. (a) R. Neumann, M. Dahan, Nature 388 (1997) 363;
93. (b) R. Neumann, M. Dahan, J. Am. Chem. Soc. 120 (1998) 11969.
94. (a) H. Weiner, Y. Hayashi, R.G. Finke, Inorg. Chim. Acta 291 (1999) 426;
95. (b) H. Weiner, R.G. Finke, J. Am. Chem. Soc. 121 (1999) 9831.
96. (a) D.K. Lyon, W.K. Miller, T. Novet, P.J. Domaille, E. Evitt, D.C. Johnson, R.G. Finke, J. Am. Chem. Soc. 113 (1991) 7209;
97. (b) D. Mansuy, J.-F. Bartoli, D.K. Lyon, R.G. Finke, J. Am. Chem. Soc. 113 (1991) 7222;
98. (c) W.M. Droege, R.G. Finke, J. Mol. Catal. 69 (1991) 323;
99. (d) Polyoxometalates: from platonic solids to anti-retroviral activity, in: A. Müller, M.T. Pope (Eds.), Proceedings of the Meeting at the Center for Interdisciplinary Research in Bielefeld, Germany, 15-17 July, Kluwer Scientific Publishers, Dordrecht, The Netherlands, 1992;
100. (e) R.G. Finke, Polyoxometalate Chemistry, in: A. Müller, M.T Pope (Eds.), Proceedings of the Meeting at the Center for Interdisciplinary Research in Bielefeld, Germany; Kluwer Academic Publishers, Dordrecht, The Netherlands, pp. 363-390.
101. C.L. Hill, I.A. Weinstock, On the trail of dioxygen activation, Nature 388 (1997) 332.
102. (a) N. Mizuno, D.K. Lyon, R.G. Finke, US Patent 5,250,739 (1993);
103. (b) N. Mizuno, D.K. Lyon, R.G. Finke, J. Catal. 128 (1991) 84;
104. (c) Y. Lin, R.G. Finke, J. Am. Chem. Soc. 116 (1994) 8335;
105. (d) Y. Lin, R.G. Finke, Inorg. Chem. 33 (1994) 4891.
106. (a) G.A. Russell, J. Am. Chem. Soc. 79 (1957) 3871;
107. (b) K.U. Ingold, Accounts Chem. Res. 2 (1969) 1;
108. (c) K.U. Ingold, Pure Appl. Chem, 15 (1967) 49;
109. (d) J.A. Howard, K.U. Ingold, Can. J. Chem. 46 (1968) 2655, 2661; see also [3];
110. (e) J.E. Bennett, D.M. Brown, B. Mile, Trans. Faraday Soc. 66 (1970) 386, 397;
111. (f) J.E. Bennett, D.M. Brown, B. Mile, Chem. Commun. (1969) 504;
112. (g) K. Adamic, J.A. Howard, K.U. Ingold, Chem. Commun. (1969) 505.
113. (a) J.E Roth, CHEMTECH June (1991) 357;
114. (b) T. Hayashi, K. Tanaka, M. Haruta, J. Catal. 178 (1998) 566.
115. 62], J. Mol. Catal. 191 (2003) 253-279.
116. H. Weiner, Y. Hayashi, R.G. Finke, Inorg. Chem. 38 (1999) 2579 (see Fig. 1).
117. (a) N. Mizuno, H. Weiner, R.G. Finke, J. Mol. Catal. 114 (1996) 15;
118. (b) H. Weiner, R.G. Finke, Co-oxidative Epoxidations of Olefins with Molecular Oxygen and Aldehyde Reductants. Part II. Development and Kinetic and Mechanistic Studies of a Radical-Initiated, High Yield and High Selectivity but Uncatalyzed Process, in preparation.
119. (a) J.K. Kochi (Ed.), Free Radicals, vol. II, Wiley, New York, 1973, Chapters II-IV, pp. 5-37;
120. (b) E.S. Huyser, Free Radical Chain Reactions, Wiley/Interscience, New York, 1970, p. 39;
121. (c) J.A. Howard, in: K. Kochi (Eds.), Free Radicals, vol. 2, Wiley, New York, 1973, p. 3.
122. J.A. Howard, in: K. Kochi (Ed.), Free Radicals, vol. 2, Wiley, New York, 1973, p. 11.
123. (a) J. Halpern, T. Okamoto, A. Zakhariev, J. Mol. Cat. 2 (1976) 65;
124. (b) J. Halpern, Inorg. Chim. Acta 50 (1981) 11.
125. (a) G.M. Bulgakova, A.N. Shupik, I.P. Skibida, K.I. Zamaraev, Z.K. Maizus, Docl. Akad. Nauk SSSR 199 (1971) 376;
126. (b) A.V. Tobolsky, India Rubber World 118 (1948) 363.
127. (a) E.G. Janzen, Accounts Chem. Res. 4 (1971) 31;
128. (b) E.G. Janzen, L.D. Haire, Adv. Free Radical Chem. 1 (1990) 253.
129. (a) R. Criegee, H. Pilz, H. Flygare, Ber. 72 (1939) 1799;
130. (b) A.A. Fruner, J. Org. Chem. 42 (1977) 3194;
131. (c) A.J. Bloodworth, H.J. Eggelte, J. Chem. Soc., Perkin Trans. 1 (1981) 1375;
132. (d) G.O. Schlenck, K.H. Schulte-Elte, Ann. 618 (1958) 185.
133. (a) L. Bertrand, J.A. Franklin, P. Goldfinger, G. Huybrechts, J. Phys. Chem. 72 (1968) 3926;
134. (b) L. Bertrand, L. Exsteen-Meyers, J.A. Franklin, G. Huybrechts, J. Olbregts, Int. J. Chem. Kinetics 3 (1971) 89;
135. (c) V.W. Day, T.A. Eberspacher, W. Klemperer, B. Zhong, J. Am. Chem. Soc. 116 (1994) 3119.
136. (a) M. Pohl, D.K. Lyon, K. Mizuno, K. Nomiya, R.G. Finke, Inorg. Chem. 34 (1995) 1423;
137. (b) M. Pohl, Y. Lin, T.J.R. Weakley, K. Nomiya, M. Kaneko, H. Weiner, R.G. Finke, Inorg. Chem. 34 (1995) 767;
138. (c) T. Nagata, M. Pohl, H. Weiner, R.G. Finke, Inorg. Chem. 36 (1997) 1366;
139. (d) H. Weiner, J.D. Aiken III, R.G. Finke, Inorg. Chem. 35 (1996) 7905.
140. (a) R. Criegee, H. Pilz, H. Flygare, Ber. 72 (1939) 1799;
141. (b) L. Bateman, H. Hughes, J. Chem. Soc. (1952) 4594;
142. (c) For an alternative route to cyclohexene hydroperoxide see: A.A. Frimer, J. Org. Chem. 19 (1977) 3194;
143. (d) O.L. Magelli, C.S. Shepard, in: D. Swern (Ed.), Organic Peroxides, vol. I, Wiley/Interscience, New York, 1970, pp. 1-19;
144. (e) R. Hiatt, in: Organic Peroxides, Wiley/Interscience, New York, 1970, pp. 1-39 and 114-115;
145. (f) A.G. Davies, Organic Peroxides, Butterworths, London, 1961, pp. 1-41;
146. (g) A.G. Tobelsky, R.B. Mesrobian, Organic Peroxides, Interscience, New York, 1954, pp. 1-11.
147. (a) L.W. Fine, M. Grayson, V.H. Suggs, J. Organomet. Chem. 22 (1970) 219;
148. (b) R.M. Johnson, I.W. Siddigi, The Determination of Organic Peroxides, Pergamon Press, New York, 1970, pp. 15-28.
149. (a) A.C. Melnyk, N.K. Kildahl, A.R. Rendina, D.H. Busch, J. Am. Chem. Soc. 101 (1979) 3232;
150. (b) For initial rate method see: R.G. Wilkins (Ed.), Kinetics and Mechanism of Reactions of Transition Metal Complexes, 2nd ed., VCH, New York, 1991, pp. 3-4.
151. D.C. Harris Quantitative Chemical Analysis, 3rd ed., Freeman, New York, 1991, pp. 410-419.
152. A.E. Pierce, Silylation of organic compounds, in: Identification of Organic Compounds with the Aid of Gas Chromatography, Pierce Chemical Company/McGraw-Hill, Rockford, IL/New York, 1968/1973, p. 163.
153. (a) M.N. Sheng, J.G. Zajacek, Hydroperoxide oxidations catalyzed by metals, in: F.R. Mayo (Ed.), Oxidation of Organic Compounds, Advances in Chemistry Series 76, vol. 2, ACS, Washington, DC, 1968, pp. 418-431;
154. (b) J. Kollar, US Patent 3,351,635 (1967);
155. (c) H.P. Wulff, US Patent 3,923,843 (1975);
156. (d) R.A. Sheldon, Aspects Homog. Catal. 4 (1981) 3;
157. (e) B.H. Isaacs, US Patent 4,590,172 (1986);
158. (f) M.K. Trost, R.G. Bergmann, Organometallics 10 (1991) 1172;
159. (g) K.A. Jorgensen, Chem. Rev. 89 (1989) 431;
160. (h) A.O. Chong, B. Sharpless, J. Org. Chem. 42 (1977) 1587;
161. (i) T Iwahama, G. Hatta, S. Sakaguchi, Y. Ishii, Chem. Comm. (2000) 163.
162. M.A. Wateky, R.G. Finke, J. Am. Chem. Soc. 119 (1997) 10382.