| 摘要 |
Organic carbonyl compounds are obtained by ozonizing organic compounds having carbon-carbon unsaturation in a participating solvent to yield at least one derivative containing a peroxy group which is then reduced with a sulphide of formula RSR1 wherein R and R1 may be alkyl, alkenyl, aryl, aralkyl, alkanyl or in which R and R1 are bridged to form a cyclic compound which may include a second sulphur atom e.g. tetrahydrothiophene or dithiane. The solvents used are substantially inert to ozonization under the conditions used and are preferably alkyl alcohols, glycols and aliphatic carboxylic acids having 1-12 carbon atoms. The solvents may be mixed with common inert ozonization solvents such as water, acetone and hexane. The ozonization may be a batch or continuous process and commonly comprises passing a stream of oxygen containing ozone through a solution of the unsaturated compound at temperatures below 50 DEG C., e.g. 25 DEG to 70 DEG C. The product may be obtained by distillation, extraction or cyrstallization, or by conversion to a solid condensation product using reagents such as 2,4-dinitrophenylhydrazine, semicarbazide and hydroxylamine. In the case of naphthalene and phenanthrene the aldehyde product forms a complex with dimethyl sulphoxide, formed from the oxidation of CH3SCH3, but can be recovered by treatment with hydrochloric acid. Specified starting materials are naphthalene, phenanthrene, styrene, isosafrole, 4 - vinylpyridine, 4 - nitro-styrene, indene, cyclohexene, 1-octene, 1-do-decene, maleic acid, diethyl fumarate, dimethyl maleate and diethyl maleate.
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