Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1991-09-09
1995-03-21
Prescott, Arthur C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07C 5116
Patent
active
053997492
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates processes for making carboxylic acids by treating alkenes and other organic compounds containing carbon-carbon double bonds with ozone to form ozonides and oxidizing the ozonides to form a carboxyl group on each carbon atom in the original carbon-carbon double bond. The oxidation step utilizes diatomic oxygen, which may be mixed with other gases, as oxidant and is speeded by use of a heterogeneous catalyst.
STATEMENT OF RELATED ART
The general chemical course of the reactions involved in a process according to this invention is well known. The part of the overall process involving oxidation of ozonides has been reported to be catalyzed with "Lindlar Catalyst", which is a special preparation of palladium on calcium carbonate, selenium oxide, metal soaps, ester soaps, manganese diacetate, a cation exchange resin catalyst, and salts of metals with two or more stable valence states (in addition to zero valence).
In what is believed to be one of the examples of this related art most pertinent to the present invention, U.S. Pat. No. 3,979,450 according to an abstract thereof teaches making dicarboxylic acids by ozonizing a cycloolefin dissolved in a lower monocarboxylic acid, treating the resulting product with aqueous hydrogen peroxide, passing the resulting mixture through a solid acid catalyst at 30.degree.-60.degree. C., completing the oxidation in a separate reaction zone at 50.degree.-80.degree. C. in the absence of catalyst, and decomposing the oxidation product by heating at 90.degree.-110.degree. C.
U.S.S.R. patent publication 330154 according to an abstract thereof teaches ozonizing oleic acid in solution in a lower carboxylic acid, then passing the ozonilysate and hydrogen peroxide through a column of solid, acidic catalyst at 50.degree.-80 C. to produce azelaic and pelargonic acids.
Catalysis of the decomposition of hydroperoxides by zeolites and clays has been reported, but the type of decomposition reported is not believed to lead to carboxylic acid products. For example, published European Patent Application 0 203 632 according to an abstract thereof teaches that crystalline zeolites in which a portion of the silicon atoms in the crystal lattice are replaced by aluminum and boron atoms are effective catalysts for the selective decomposition of cumene hydroperoxide to phenol and acetone; and published German Patent Application DE 32 22 143 according to an abstract thereof teaches that NaA, NaX, and NaY zeolites modified with cobalt catalyze the decomposition of cyclohexyl hydroperoxide to cyclohexanone and cyclohexanol. These hydroperoxides are distinct chemical entities from ozonides, however.
DESCRIPTION OF THE INVENTION
In this description, except in the claims and the operating examples or where explicitly otherwise indicated, all numbers describing amounts of ingredients or reaction conditions are to be understood as modified by the word "about" in describing the broadest embodiments of the invention. Operation within the exact numerical limits given is generally preferred.
SUMMARY OF THE INVENTION
A major embodiment of the present invention is a process in which organic molecules containing a structural unit of the formula --CH.dbd.CH-- are each converted into two or more molecules containing a structural unit of the formula --COOH by reaction with ozone to form one or more ozonides and subsequent or simultaneous reaction of the ozonide(s) with gaseous diatomic oxygen. (In this description, any oxygen containing product of direct reaction between ozone and organic molecules containing carbon-carbon double bonds is to be understood as an ozonide.) The diatomic oxygen may be mixed with other non-oxidizing gases, as in normal air or oxygen enriched air. The improvement in the process is that the reagents are in fluid form and are in contact, during at least part of the reaction with the diatomic oxygen gas, with a solid phase selected from X and Y type zeolites, preferably X type zeolites, most preferably sodium or potassium zeolite X. (An
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Henkel Corporation
Jaeschke Wayne C.
Prescott Arthur C.
Szoke Ernest G.
Wisdom, Jr. Norvell E.
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