Process for producing alkylthio- and arylthio-substituted carboxylic acids and their thioesters
AssigneeElf Atochem North America, Inc.
InventorsMichael J. Lindstrom, Bernard Buchholz, Robert B. Hager
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Abstract
A process is provided for producing alkylthio-substituted carboxylic acids and arylthio-substituted carboxylic acids and their corresponding alkylthio-substituted thioesters and arylthio-substituted thioesters. The process comprises reacting a mercaptan with a lactone in the presence of an acidic catalyst at temperatures of about 100.degree. C. to about 350.degree. C. The process for preparing the thio-substituted carboxylic acids and thio-substituted thioesters may be a continuous process or a batch process.
Claims27
A process for producing a thio-substituted carboxylic acid selected from the group consisting of an alkylthio-substituted carboxylic acid and an arylthio-substituted carboxylic acid comprising reacting in the presence of a catalytic amount of an acidic catalyst a lactone selected from the group consisting of an alkyl lactone and an aryl lactone and a mercaptan selected from the group consisting of an alkyl mercaptan and an aryl mercaptan, where the lactone to mercaptan mole ratio is about 5:1 to about 15:1, at a temperature of about 100.degree. C. to about 350.degree. C.
A process for producing a thio-substituted thioester selected from the group consisting of an alkylthio-substituted thioester and an arylthio-substituted thioester comprising reacting in the presence of a catalytic amount of an acidic catalyst a lactone selected from the group consisting of an alkyl lactone and an aryl lactone and a mercaptan selected from the group consisting of an alkyl mercaptan and an aryl mercaptan, where the lactone to mercaptan mole ratio is about 0.1:1 to about 2:1, at a temperature of about 100.degree. C. to about 350.degree. C.
A process for preparing a compound having a formula ##STR8## by reacting in the presence of a catalytic amount of an acidic catalyst at a temperature of about 100.degree. C. to about 350.degree. C. a mercaptan having a formula RSH with a lactone having a formula ##STR9## wherein R is a radical selected from the group consisting of substituted or unsubstituted alkyl of 1 to 25 carbons, substituted or unsubstituted cycloalkyl of 5 to 25 carbons, substituted or unsubstituted aryl of 6 to 25 carbons, substituted or unsubstituted aralkyl of 7 to 26 carbons, substituted or unsubstituted alkyl hydroxy of 1 to 25 carbons, substituted or unsubstituted alkoxy alkyl of 2 to 25 carbons, halogen-substituted aliphatic of 1 to 25 carbons, where the substituents for R are hydroxy, halogen, alkyl of 1 to 6 carbons or aryl of 6 to 12 carbons;
- A is selected from the group consisting of --YCR.sup.1 R.sup.2 (CR.sup.3 R.sup.4).sub.x -- and ##STR10## wherein Y is the bond location to the carbonyl carbon;
- R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl of 1 to 25 carbons, substituted or unsubstituted aryl of 6 to 25 carbons, substituted or unsubstituted aralkyl of 7 to 26 carbons, substituted or unsubstituted alkoxy alkyl of 2 to 25 carbons, halogen-substituted alkyl of 1 to 25 carbons, substituted or unsubstituted alkoxy of 2 to 25 carbons, substituted or unsubstituted thioalkoxy of 1 to 25 carbons, dialkylamino of 2 to 25 carbons and diarylamino of 12 to 25 carbons, where the substituents for any of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydroxy, halogen, alkyl of 1 to 6 carbons or aryl of 6 to 12 carbons, with the proviso that R.sup.1 and R.sup.3 may together comprise a ring and R.sup.2 and R.sup. 4 may together comprise a ring;
- R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl of 1 to 25 carbons, substituted or unsubstituted aryl of 6 to 25 carbons, substituted or unsubstituted aralkyl of 7 to 26 carbons, substituted or unsubstituted alkoxy alkyl of 2 to 25 carbons, halogen-substituted alkyl of 1 to 25 carbons, substituted or unsubstituted alkoxy of 1 to 25 carbons, substituted or unsubstituted thioalkoxy of 1 to 25 carbons, dialkylamino of 2 to 25 carbons and diarylamino of 12 to 25 carbons, where the substituents for any of R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are hydroxy, halogen, alkyl of 1 to 6 carbons or aryl of 6 to 12 carbons;
- x is an integer from 2 to 5;
- y is an integer from 1 to 5;
- and
- Z is selected from the group consisting of --OH and --SR.
Dependencies are inferred from the claim text.