Oxidative cleavage of polyethylenically unsaturated compound to

Details Oxidative cleavage of polyethylenically unsaturated compound to Oxidative cleavage of polyethylenically unsaturated compound to

1993-10-27

1995-01-10

Prescott, Arthur C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

562543, 562544, C07C 5116

Patent

active

053809319

ABSTRACT:
A method of oxidatively cleaving polyethylenically unsaturated compound having a pair of carbon atoms ethylenically bonded to other carbon atoms but singly bonded to each other or a pair of carbon atoms ethylenically bonded to other carbon atoms but separated from each other by a saturated carbon atom to produce a carboxylic acid is disclosed. A hydroperoxide such as hydrogen peroxide is used as the oxidant and a salt of vanadic acid such as sodium metavanadate is used as a catalyst to oxidatively cleave such an unsaturated compound in a polar organic solvent. Ethylenically unsaturated compounds that do not contain carbon-carbon double bonds separated by one or two carbon-carbon single bonds, such as a monoethylenically unsaturated carboxylic acid present in a mixture with the polyethylenically unsaturated compound, are not oxidized or only minimally oxidized.

REFERENCES:
patent: 2133008 (1938-10-01), Ralston et al.
patent: 2203628 (1940-06-01), Hopff et al.
patent: 2203680 (1940-05-01), Ellingboe
patent: 2226357 (1940-12-01), Olin et al.
patent: 2676186 (1954-04-01), Dunlop et al.
patent: 3031482 (1962-04-01), Stein et al.
patent: 3890246 (1975-06-01), Grasselli et al.
patent: 4052418 (1977-10-01), Suresh et al.
patent: 4098817 (1978-07-01), Barone
patent: 4099018 (1978-07-01), Stapp
patent: 4293443 (1981-10-01), Suresh et al.
patent: 4309310 (1982-01-01), Callahan
patent: 4331608 (1982-05-01), Kawamoto et al.
patent: 4532079 (1985-07-01), Venturello et al.
patent: 4606863 (1986-08-01), Nakazawa et al.
patent: 4833272 (1989-05-01), Nakazawa et al.
patent: 4868328 (1989-09-01), Drent
patent: 4931590 (1990-06-01), Kummer et al.
patent: 5041470 (1991-08-01), Gelorme et al.
Hudlicky, "Oxidations", Oxidations in Organic Chemistry, American Chemical Society, 77-90 (1990).
Ishii et al., "Hydrogen Peroxide Oxidation Catalyzed by Heteropoly Acids Combined with Cetylpyridinium Chloride: Epoxidation of Olefins and Allylic Alcohols, Ketonization of Alcohols and Diols, and Oxidative Cleavage of 1,2-Diols, and Olefins", J. Org. Chem., 53, 3587-3593 (1988).
Oguchi et al., "Oxidative Cleavage of Olefins into Carboxylic Acids with Hydrogen Peroxide by Tungstic Acid", Chemistry Letters, The Chemical of Society of Japan, 857-860 (1989).
Sheldon et al., "Metal Catalysts in Peroxide Reactions", Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, 49-56 (1981).
Zaldman et al., "Double Bond Oxidation of Unsaturated Fatty Acids", JAOCS, 65, 611-615 (1988).

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