Process for the production of oxiranes

Details Process for the production of oxiranes Process for the production of oxiranes

1990-04-03

1993-10-26

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30114

Patent

active

052568024

ABSTRACT:
Oxiranes are made from ketones by heating a ketone which is preferably an alkyl ketone to a temperature of from about 60.degree. to about 90.degree. C. (preferably about 80.degree. C.) in the presence of a sulfonium salt, a quaternary ammonium salt and a potassium hydroxide solution which is at least 61% potassium hydroxide. It is preferred that no organic solvent be included in the reaction mixture. The potassium hydroxide is generally included in an amount such that for every mole of ketone, from about 3 to about 4 moles of potassium hydroxide are present. The sulfonium salt is generally used in an amount of at least 1.1 moles for each mole of ketone. The quaternary ammonium salt is generally used in an amount of from about 1 to about 5 mol % based on moles of ketone present.

REFERENCES:
patent: 3998856 (1976-12-01), Rosenberger
Shiraki et al, Anion-catalyzed Phase-transfer Catalysis II, Bull. Chem. Soc. Japan, vol. 58, pp. 3041-3042, 1985.
Merz et al, Phase-transfer-catalyzed Production of Sulfur Ylides in an Aqueous System, Angew. Chem. Int. Ed., vol. 12, pp. 845-846, 1973.
Melvin Hatch, The Synthesis of Oxiranes from Aqueous Solutions of Simple Alkyl, Allyl, and Benzylsulfonium Salts, Jour. Org. Chem. vol. 34, pp. 2133-3137, 1968.
Bouda et al, Aldehydes and Ketones Epoxidation With Trimethylsulfonium Bromide In a Slightly Hydrated Solid-Liquid Medium, Synthetic Communications vol. 7(5), pp. 503-513 (1987).

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