Process for selective reduction of unsaturated organic compounds

Chemistry of hydrocarbon compounds – Adding hydrogen to unsaturated bond of hydrocarbon – i.e.,...

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585271, 585275, 585700, C07C 500, C07C 502, C07C 504, C07C 200

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052547612

ABSTRACT:
A reducible unsaturated organic compound is reduced with diimide in an aqueous emulsion comprised of water, an organic phase which contains the compound to be reduced, and an effective stabilizing amount of an anionic surfactant. The organic compound is preferably an unsaturated organic compound containing a carbon-to-carbon multiple bond, which is preferably a carbon-to-carbon double bond. Diimide is formed by reaction of hydrazine with an oxidant in the aqueous emulsion described above. The preferred oxidant is hydrogen peroxide. A product is obtained in high yield and purity in most cases. This process is especially useful for the selective reduction of a compound having two or more carbon-to-carbon double bonds of different reactivities or a carbon-to-carbon double bond and a functionality (e.g., an O--O or S--S linkage) which is reducible by catalytic hydrogenation but not diimide.

REFERENCES:
patent: 4452950 (1984-05-01), Wideman
patent: 4469849 (1984-09-01), Murrer et al.
patent: 5039737 (1991-08-01), Parker et al.
Hunig et al., "The Chemistry of Diimine", Angewandte Chemie, International Edition, vol. 4, No. 4, Apr. 1965, pp. 271-280.
Organic Syntheses, Collective Volume V, H. E. Baumgarten, ed.; Pub. by John Wiley & Sons, New York, 1973; pp. 281-284.
Organic Reactions, vol. 40, L. A. Paquette et al, ed: Pub. by John Wiley & Sons, New York, 1991; pp. 91-155.
D. K. Parker et al, "A New Process for the Preparation of Highly Saturated Nitrile LRubber in Latex Form: (Chemistat"), paper No. 58, presented at the 139th meeting of the Rubber Division, American Chemical Society, Toronto, Ontario, Canada, May 21-24, 1991 (33 pages).

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