The effect of zirconium in metal/bromide catalysts during the autoxidation of p-xylene: Part I. Activation and changes in benzaldehyde intermediate formation

Journal of Molecular Catalysis A: Chemical

Volumn 206, Issue 1-2, 2003, Pages 105-119

  Partenheimer, Walt ^a  

^a DUPONT COMPANY   (United States)

Author keywords

Activation; Activator; Aerobic; Autoxidation; Bromide; Catalyst precipitation; Cerium; Cobalt; Dioxygen; Homogeneous liquid phase catalysis; Lewis acid strength; Manganese; Oxidation; p Xylene; PET; Polyester; Selectivity; Terephthalic acid

Indexed keywords

CATALYST ACTIVITY; CONCENTRATION (PROCESS); COORDINATION REACTIONS; OXIDATION; XYLENE; ZIRCONIUM;

WATER SYSTEMS;

CATALYSIS;

ACETIC ACID; BENZALDEHYDE; BENZYL HYDROPEROXIDE; BROMIDE; CERIUM; COBALT; HYDROPEROXIDE DERIVATIVE; LEWIS ACID; MANGANESE; METAL COMPLEX; PARA XYLENE; UNCLASSIFIED DRUG; WATER; ZIRCONIUM;

ACIDITY; ADDITION REACTION; ARTICLE; AUTOOXIDATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141563358     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(03)00407-2     Document Type: Article

References (47)

1. (a) R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, NY, 1981 (Chapter 1); (b) For a good history of autoxidation see references quoted in: H. Weiner, A. Trovarelli, R.G. Finke, J. Mol. Catal. A 191 (2003) 217.
2. (a) R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, NY, 1981 (Chapter 1); (b) For a good history of autoxidation see references quoted in: H. Weiner, A. Trovarelli, R.G. Finke, J. Mol. Catal. A 191 (2003) 217.
3. (a) K. Weissermel, H.J. Arpe, Industrial Organic Chemistry, third ed., Verlag Chemie, Weinheim, New York, NY, 1997; (b) A.K. Sureh, M.M. Sharma, T. Sridharv, Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons, Ind. Engl. Chem. Res. 39 (2000) 3958.
4. (a) K. Weissermel, H.J. Arpe, Industrial Organic Chemistry, third ed., Verlag Chemie, Weinheim, New York, NY, 1997; (b) A.K. Sureh, M.M. Sharma, T. Sridharv, Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons, Ind. Engl. Chem. Res. 39 (2000) 3958.
5. W.C. Fischer, R. Roehrscheid, Oxidation of alkyl-substituted aromatic compounds with air, in: Applied Homogeneous Catalysis with Organometallic Compounds, second ed., vol. 1, 2002, pp. 443-467.
6. W. Partenheimer, The methodology and scope of metal/bromide autoxidation of hydrocarbons, Catal. Today 23 (1995) 70-158.
7. A.W. Chester, P.S. Landis, E.J.Y. Scott, Oxidize aromatics over doped cobalt, Chemtech (1978) 366.
8. W. Partenheimer, W.P. Schammel, Oxidation process for the manufacture of aromatic acids from alkylaromatic compounds, US Patent 4,786,753 (1988).
9. W. Partenheimer, A method for the preparation of pyromellitic acid from durene via liquid phase oxidation, in: D.W. Blackburn (Ed.), Catalysis of Organic Reactions, Marcel Dekker, New York, 1994 (Chapter 14).
10. I. Ichikawa, US Patent 3,299,125 (1967).
11. A.W. Chester, E.J.Y. Scott, P.S. Landis. Zirconium cocatalysis of the cobalt-catalyzed autoxidation of alkylaromatic hydrocarbons, J. Catal. 46 (1977) 308.
12. G.S. Bezhanishvili, N.G. Digurov, N.N. Lebedev, D.I. Mendeleev, Kinetics of the oxidation of toluene over a cobalt bromide catalyst with the addition of zirconyl chloride, Trans. Kinet. Katal. 24 (4) (1983) 1000.
13. W. Partenheimer, W.P. Schammel, US Patent 4,786,753 (1988).
14. G.L. Wamfler, G.E. Croft, US Patent 3,920,735 (1975).
15. J. Darin, A. Bemis, US Patent 4,895,978 (1990).
16. F.G. Belmonte, K.A. Fjare, W. Partenheimer, US Patent 5,112,992 (1992).
17. W. Partenheimer, V.V. Grushin, Synthesis of 2,5-diformylfuran and furan-2,5-dicarboxylic acid by catalytic air-oxidation of 5-hydroxymethylfurfural. Unexpectedly selective aerobic oxidation of benzyl alcohol to benzaldehyde with metal/bromide catalysts, Adv. Synth. Catal. 343 (2001) 102.
18. W. Partenheimer, Valuable oxygenates by aerobic oxidation of polymers using metal/bromide homogeneous catalysts, Catal. Today, in press.
19. G.R. Steinmetz, N.L. Lafferty, C.E. Sumner Jr., The cobalt/zirconium catalyzed oxidation of cyclohexane to adipic acid, J. Mol. Catal. 49 (1988) L39.
20. W. Partenheimer, Novel catalytic characteristics of the Co/Mn/Cl/Br liquid phase oxidation catalyst, in: F.E. Herkes (Ed.), Catalysis of Organic Reactions, Marcel Dekker, New York.
21. W. Partenheimer, Kinetic modeling studies to determine the feasibility of preparing benzaldehydes and benzylic alcohols from metal/bromide catalyzed autoxidations, in: North American Catalysis Society Meeting, Chicago, IL, 19 May 1997.
22. F. Minisci, C. Punta, F. Recuperoa, F. Fontana, G.F. Pedullia, A new, highly selective synthesis of aromatic aldehydes by aerobic free-radical oxidation of benzylic alcohols, catalysed by n-hydroxyphthalimide under mild conditions. Polar and enthalpic effects, Chem. Commun. (7) (2002) 688-689.
23. (a) G. Cao, M. Pisu, M. Morbidelli, A lumped kinetic model for liquid-phase catalytic oxidation of p-xylene to terephthalic acid, Chem. Eng. Sci. 49 (1994) 5775; (b) T.I.A. Gerber, A. Wiechers, A.T. Noah, B. Zeelie, The partial air oxidation of alkyl aromatic compounds catalysed by cobalt/bromide in carboxylic acids: mechanistic considerations, S. Afr. Tydskr. Chem. 51 (1998) 178.
24. (a) G. Cao, M. Pisu, M. Morbidelli, A lumped kinetic model for liquid-phase catalytic oxidation of p-xylene to terephthalic acid, Chem. Eng. Sci. 49 (1994) 5775; (b) T.I.A. Gerber, A. Wiechers, A.T. Noah, B. Zeelie, The partial air oxidation of alkyl aromatic compounds catalysed by cobalt/bromide in carboxylic acids: mechanistic considerations, S. Afr. Tydskr. Chem. 51 (1998) 178.
25. R.K. Gipe, W. Partenheimer, Catalysts by rational design: prediction and confirmation of the properties of the Co/Ce/Br liquid-phase autoxidation catalyst based on the kinetic similarity to the Co/Mn/Br catalyst, in: R.K. Grasselli, S.T. Oyama, A.M. Gaffney, J.E. Lyons (Eds.), Studies in Surface Science and Catalysis, Elsevier, Amsterdam, 1997, p. 1117.
26. S.A. Chavan, S.B. Halligudi, D. Srinivas, P. Ratnasamy, Formation and role of cobalt and manganese cluster complexes in the oxidation of p-xylene, J. Mol. Catal. A 161 (2000) 49.
27. E.J.Y. Scott, The kinetics of the reaction of cobalt(II) and cobalt(III) acetates with benzyl hydroperoxide in acetic acid at 25 °C, J. Phys. Chem. 74 (1970) 1174.
28. W. Partenheimer, A chemical model for the Amoco 'MC' oxygenation process to produce terephthalic acid, in: D.W. Blackburn (Ed.), Catalysis of Organic Reactions, Marcel Dekker, New York, 1990 (Chapter 20).
29. W. Partenheimer, The structure of metal/bromide catalysts in acetic acid/water mixtures and its significance in autoxidation, J. Mol. Catalysis 174 (2001) 29.
30. (a) P.D. Metelski, A. Adamian, J.H. Espenson, Mechanistic role of benzylic bromide in the catalytic autoxidation of methylarenes, Inorg. Chem. 39 (2000) 2434; (b) G.M. Dugmore, G.J. Powels, B. Zeelie, Mechanistic aspects of benzylic bromide catalyzed oxidation of alkylbenzenes in carboxylic acids, J. Mol. Catal. A: Chem. 99 (1995).
31. (a) P.D. Metelski, A. Adamian, J.H. Espenson, Mechanistic role of benzylic bromide in the catalytic autoxidation of methylarenes, Inorg. Chem. 39 (2000) 2434; (b) G.M. Dugmore, G.J. Powels, B. Zeelie, Mechanistic aspects of benzylic bromide catalyzed oxidation of alkylbenzenes in carboxylic acids, J. Mol. Catal. A: Chem. 99 (1995).
32. L.W. Hessel, C. Romers, The crystal structure of anhydrous manganic acetate, Recueil 88 (1969) 545.
33. T.P. Kenigsberg, E.D. Skakovskii, N.G. Ariko, N.I. Mitskevich, Role of complex formation in the oxidative transformations of methyl benzenes and acetic acid under conditions of metal bromide catalysis, Kinetika i Kataliz 31 (1990) 1135-1140.
34. C.F. Hendriks, H.C.A. von Beek, P.M. Heertjes, Ind. Eng. Chem. Prod. Res. Dev. 18 (1979) 43.
35. C.F. Hendriks, H.C.A. van Beek, P.M. Heertjes, The kinetics and autoxidation of aldehydes in the presence of cobalt(II) and cobalt(III) acetate in acetic acid solution, Ind. Eng. Chem. Prod. Res. Dev. 17 (1978) 260.
36. R.W. Brandon, C.S. Elliott, Tetrahedron Lett. 44 (1967) 4375.
37. F.A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, fourth ed., Wiley/Interscience, 1980, p. 158.
38. F. Basolo, R.G. Pearson, Mechanisms of Inorganic Reactions: A Study of Metal Complexes in Solution, second ed., Wiley, New York, 1967, p. 63.
39. N.M. Emanuel, E.T. Devisov, Z.K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum Press, New York, NY, 1967 (translated from the Russian).
40. (a) X.-D. Jiao, P.D. Metelski, J.H. Espenson, Equilibrium and kinetics studies of reactions of manganese acetate, cobalt acetate, and bromide salts in acetic acid solutions, Inorg. Chem. 40 (2001) 3228; (b) P.D. Metelski, J.H. Espenson, Kinetic and mechanism of reactions between methyl aromatic compounds and the dibromide radical, J. Phys. Chem. A 105 (2001) 5881.
41. (a) X.-D. Jiao, P.D. Metelski, J.H. Espenson, Equilibrium and kinetics studies of reactions of manganese acetate, cobalt acetate, and bromide salts in acetic acid solutions, Inorg. Chem. 40 (2001) 3228; (b) P.D. Metelski, J.H. Espenson, Kinetic and mechanism of reactions between methyl aromatic compounds and the dibromide radical, J. Phys. Chem. A 105 (2001) 5881.
42. G.H. Jones, A mechanistic study of the origins of synergy and antagonism in the Co/Br and Mn/Br catalysed autoxidation of p-xylene, J. Chem. Res. 5 (1982) 207.
43. Y. Kamiya, T. Nakjima, K. Sakoda, Bull. Chem. Soc. Jpn. 39 (1966) 2211.
44. (a) Y.V. Geletii, I.V. Zakharov, Catalytic route of hydrocarbon oxidation by dioxygen in the presence of transition metal ions in protic media, Oxid. Commun. 6 (1984) 23; (b) I.V. Zakharov, Y.V. Geletii, Route of autoxidation of organic compounds through a metal ion and bromide catalysis, Neftekhimiya 26 (1986) 776.
45. (a) Y.V. Geletii, I.V. Zakharov, Catalytic route of hydrocarbon oxidation by dioxygen in the presence of transition metal ions in protic media, Oxid. Commun. 6 (1984) 23; (b) I.V. Zakharov, Y.V. Geletii, Route of autoxidation of organic compounds through a metal ion and bromide catalysis, Neftekhimiya 26 (1986) 776.
46. W. Partenheimer, Nature of the Co-Mn-Br catalyst in the methylaromatic compounds process: kinetic and thermodynamic studies, in: S.T. Oyama, J.W. Hightower (Eds.), Catalytic Selective Oxidation, American Chemical Society, 1993 (Chapter 7).
47. M.C. Day, J. Selbin, Theoretical Inorganic Chemistry, second ed., Reinhold, New York, p. 120.