Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1993-01-27
1994-03-08
Prescott, Arthur C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07C 5116
Patent
active
052929418
DESCRIPTION:
BRIEF SUMMARY
FILED OF THE INVENTION
This invention relates to a method for ozonizing unsaturated fatty acids or lower alkyl esters thereof at their unsaturated bond and a method for oxidative decomposition of the thus ozonized products into short chain monobasic or dibasic acids or esters thereof.
BACKGROUND OF THE INVENTION
It is known in the prior art to cause ozone to act on unsaturated fatty acids such as oleic acid, thereby effecting continuous ozonization of their double bond (Japanese Patent Publication No. 4714/1961 or U.S. Pat. No. 2,813,113 and Japanese Patent Publication No. 9206/1968).
The prior art continuous ozonization methods of unsaturated fatty acids which use an apparatus having a plurality of reaction zones and rely on the counterflow gas-liquid contact process of contacting unsaturated fatty acid solution with ozone-containing gas in a counterflow manner, however, are dangerous because excess ozone can be locally supplied to form peroxides. The counterflow gas-liquid contact process of this type is difficult to quickly remove reaction heat from the apparatus or reactor tower.
German Patent No. 2,713,863 discloses a method for continuously producing an ozonide (or ozonized product) by ozonizing a high molecular weight olefin, oleic acid or linoleic acid in the presence of water and an organic acid or alcohol. Since this method supplies the reactant and an ozone-containing gas in parallel flow relationship, but does not form a thin film flow of the reactant, it is necessary to efficiently remove reaction heat generated during ozonization and to add large amounts of water and organic acid or alcohol for keeping the resulting ozonide (or ozonized product) stable, thus resulting in low yields per unit time. Moreover, although a plurality of static mixers are provided in the reactor tower for mixing organic acid and water, it is difficult to maintain a stable emulsion. As emulsion particles become larger, local heating occurs inevitably.
Also known in the prior art is oxidative decomposition by causing oxygen to act on ozonized products of unsaturated fatty acids (Japanese Patent Publication No. 4717/1961).
Although the oxidative decomposition reaction of ozonized products of unsaturated fatty acids is said to take place at a temperature of 75.degree. to 125.degree. C. according to the Publication, the actual temperature was limited up to 100.degree. C. Thus the oxidative decomposition reaction took a long time, resulting in low yields. If reaction were performed at high temperatures of 100.degree. C. or higher, especially 125.degree. C. or higher, abrupt oxidation would occur, imposing a safety problem. Also, part of the final product could be oxidized into carbon dioxide and water while forming by-products, leaving a problem in yields.
Therefore, there is a need for the development of a commercially advantageous method for the oxidative decomposition of ozonized products of unsaturated fatty acids.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a method for ozonizing an unsaturated fatty acid or a lower alkyl ester thereof which ensures efficient removal of reaction heat, safety, and increased yield per unit time in commercial scale production.
Another object of the present invention is to provide a method for oxidative decomposition of an ozonized product of an unsaturated fatty acid or a lower alkyl ester thereof which is capable of effectively and safely oxygenating and decomposing an ozonized product of an unsaturated fatty acid or a lower alkyl ester thereof in a commercial scale.
Making extensive investigations for achieving these objects, the inventors have found that by supplying a solution of an unsaturated fatty acid or a lower alkyl ester thereof as a thin film stream, and contacting a gas containing ozone in oxygen gas or a mixture of oxygen gas and air or inert gas with the thin film stream, the unsaturated fatty acid or lower alkyl ester thereof can be efficiently ozonized without a risk of excess ozone supply, that is, in a safe manner, and removal of
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Iino Yurie
Kigawa Hitoshi
Yamaya Hiroshi
Lion Corporation
Prescott Arthur C.
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