Process for oxidative functionalization of polymers containing a

Details Process for oxidative functionalization of polymers containing a Process for oxidative functionalization of polymers containing a

1997-06-04

1998-09-29

Lipman, Bernard

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

525387, C08F 800

Patent

active

058147080

ABSTRACT:
This invention provides a method by which an alkylstyrene containing polymer may be exclusively functionalized at the primary benzylic carbon site of the styrenic monomer. The process of this invention comprises the treatment of an alkylstyrene containing polymer dissolved in a non-polar liquid medium with an organic hydroperoxide oxidizing reagent in the presence of a catalytically sufficient amount of a chromium compound, to oxidize a portion of the aromatic alkyl groups of the polymer to an oxygen containing functional group.

REFERENCES:
patent: 2911387 (1959-11-01), Vandenberg
patent: 3423382 (1969-01-01), Chibnik
patent: 3864293 (1975-02-01), Miyoshi et al.
patent: 4517318 (1985-05-01), Miyoshi et al.
patent: 4593074 (1986-06-01), Dean
patent: 5162445 (1992-11-01), Powers et al.
patent: 5214108 (1993-05-01), Harrell
patent: 5376732 (1994-12-01), Stover et al.
Bird, C.W. et al., "A Convenient Synthesis by p-Hydroxybenzaldehydes", Org. Prep. and Procedures Int., 12, 201 (1980).
Lee, H. et al., "Benzylic Oxidation with 2,3-Dichloro-5,6-Dicyanobenzoquinone in Aqueous Media. A Convenient Synthesis of Aryl Ketones and Aldehydes", J. Org. Chem., 48, 479 (1983).
Chidambaram, N. et al., "tert-Butyl Hydroperoxide Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidation", J. Org. Chem., 52, 5048 (1978).
Capdeville, P. et al., "A New Oxidizing Copper Reagent: CuO.sub.2 H Preparation and Preliminary Study of Reactivity", Tetrahedron Lett., 31, 3891 (1990).
Hay, A.S. et al., "Autooxidation Reactions Catalyzed by Cobalt Acetate Bromide", Canadian J. Chem., 43, 1306 (1965).
Muzart J. et al., "Practical Chromium VI Oxide-Catalzed Benzylic Oxidations using 70% tert-Butylhydroperoxide", Tetrahedron Letts. 3(8), 595 (1992).
Zhang, S. et al., "Selective Indirect Electrooxidation of the Side Chain of Aromatic Compounds", Chin. Chem. Lett., 3(8), 595 (1992).
Shul'pin, B.G. et al., "Photoinduced Reactions of Organic Compounds with Transition Metal Complexes. Oxidation of Alkanes and Alkylbenzenes with Oxo Compounds of Chromium (VI) Under Irradiation with Light", Zh. Obscheh, Khim., 59(11), 2604, (1989).
Hronec, M. et al., "Kenetics and Mechanism of Cobalt-Catalyzed Oxidation of p-Xylene in the Presence of Water", Ind. Eng. Chem. Process Des. Dev., 23, 787-794 (1985).
Henricks, C. et al., "The Oxidation of Substitute Toluences by Cobalt (III) Acetate in Acetic Acid Solution", Ind. Eng. Chem. Prod. Res. Dev., 17(3), 256-260 (1978).
Hanotier, J. et al., "Effect of Strong acids on the Oxidation of Alkylarenes by Manganic and Cobaltic Acetates in Acetic Acid", J. Chem. Soc., Perkins Trans., 2, 381-383 (1973).
Okada, T., et al., "The Liquid-Phase Oxidation of Methylbenzenes by the Cobalt-Copper-Bromide System", Bull. Chem. Soc. Jpn. , 54, 2724-2727.
Harustiak, M. et al., "Kinetics and Mechanism of Cobalt Bromide Catalyzed Oxidation of p-Xylene in the Presence of Phase Transfer Catalysts", J. Mol. Catal., 53(1), 209-217.
Ferrari, L. et al., "Cobalt-Catalyzed Oxidation of Poly(4-Methylstyrene)", Macromolecules, 24, 6340-6342 (1991).
Glagoleva, Yu.A. et al., "Investigation of the Thermal-Oxidation Degradation of Certain Methyl-Substituted Polymers", Vysokomol. Soyed., A12: No. 9, 1994-2000, (1970)., 2263-2270.
Ferrari, Lorenzo P. et al., "Cobalt-Catalyst Oxidation of Poly(4-methylstyrene)", Macromolecules, 24, 6340-6342 (1991).
Weissermel, K. et al., "Industrial Organic Chemistry", Verlag Chemie, 1978, pp. 341-346. (Abstract Only).
J.K. Kochi, "Free Radicals", vol. 1ed. J.K. Kochi, Wiley & Sons, (1973110, pp.643-50.
Rabek, J.F. et al., Macromolecules, 19 (1986), pp. 1674-9. "Charge-Transfer Complexes Between Molecular Oxygen and Polystyrenes".
Weir, N.A. et al., "The Kinetics of Photo-Initiated Oxidation of Poly(p-Methylsyrene) in Solution", Polymer Degradation and Stability, 2 (1980), pp. 225-238.
Boerio, F.J. et al., "Selective Oxidation of Para-Substituted Polystyrenes During Surface-Enchanced Raman Scattering", Macromolecules, 22 (1989)-pp. 3955-3960.
Berko, Henry et al., "Photo-Oxidative Degradation of Copolymers of Acrylonitrile with Styrene, a-methylstyrene and p-methylstyrene", Polymer Degradation and Stability, 37 (1992)-pp. 85-90.

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