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US4172207A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for mercaptoalkanedicarboxylic acid esters

Assignee: Individual
•
Filing: 1977-02-22
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Granted: 1979-10-23
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Expires: 1997-02-22
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Abstract

Abstract A process is provided for the preparation of mercaptoalkane 1,2-dicarboxylic acid esters from readily available starting materials such as hydrogen sulfide and unsaturated alkene 1,2-dicarboxylic acid compounds. Isolation of the intermediate mercaptoalkanedicarboxylic acid can be avoided when a mercaptoalkanedicarboxylic acid ester is the desired product.

Inventors

  • 👤 Gerry P. Mack

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 16:49
CPC Classifications
C; C07; C07C; C07C327/00; C07C323/00

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 156 words
A process for producing a mercaptoalkane-1,2-dicarboxylic acid alkyl ester having 2 to 3 carbon atoms in the alkane group and 1 to about 24 carbon atoms in the alkyl group comprising the steps of first, forming a reaction mixture comprising hydrogen sulfide, acetic anhydride, and an alkene 1,2-dicarboxylic acid compound selected from the group consisting of alkene 1,2-dicarboxylic acids, alkene-1,2-dicarboxylic anhydrides, alkene-1,2-dicarboxylic esters, alkene-1,2-dicarboxylic amides, and alkene-1,2-dicarboxylic imides; second, heating the reaction mixture at 30° to 230° C. to form an S-acetylthio-1,2-alkanedicarboxylic acid compound in the reaction mixture; third, heating the reaction mixture comprising S-acetylthioalkane-1,2-dicarboxylic acid compound with a selective deacetylating agent to form a mercaptoalkane-1,2-dicarboxylic acid compound in the mixture; fourth, adding as needed alcohol having 1 to about 24 carbon atoms to the reaction mixture and heating to convert to mercaptoalkane-1,2-dicarboxylic acid esters mercaptodicarboxylic acid compounds in the mixture that are not mercaptodicarboxylic esters, and fifth, recovering mercaptoalkane-1,2-dicarboxylic acid ester from the reaction mixture.
Claim 2
Dependent Claim 156 words
A process for producing a mercaptoalkane-1,2-dicarboxylic acid alkyl ester having 2 to 3 carbon atoms in the alkane group and 1 to about 24 carbon atoms in the alkyl group comprising the steps of first, forming a reaction mixture comprising hydrogen sulfide, acetic anhydride, and an alkene 1,2-dicarboxylic acid compound selected from the group consisting of alkene 1,2-dicarboxylic acids, alkene-1,2-dicarboxylic anhydrides, alkene-1,2-dicarboxylic esters, alkene-1,2-dicarboxylic amides, and alkene-1,2-dicarboxylic imides; second, heating the reaction mixture at 30° to 230° C. to form an S-acetylthio-1,2-alkanedicarboxylic acid compound in the reaction mixture; third, heating the reaction mixture comprising S-acetylthioalkane-1,2-dicarboxylic acid compound with a selective deacetylating agent to form a mercaptoalkane-1,2-dicarboxylic acid compound in the mixture; fourth, adding as needed alcohol having 1 to about 24 carbon atoms to the reaction mixture and heating to convert to mercaptoalkane-1,2-dicarboxylic acid esters mercaptodicarboxylic acid compounds in the mixture that are not mercaptodicarboxylic esters, and fifth, recovering mercaptoalkane-1,2-dicarboxylic acid ester from the reaction mixture.
Claim 3
Dependent Claim 28 words
A process according to claim 1 in which the alkene-1,2-dicarboxylic acid compound is an alkene-1,2-dicarboxylic acid alkyl ester having 1 to 24 carbon atoms in each alkyl group.
Claim 4
Dependent Claim 28 words
A process according to claim 1 in which the alkene-1,2-dicarboxylic acid compound is selected from the group consisting of maleic acid, maleic anhydride, itaconic acid, and itaconic anhydride.
Claim 5
Dependent Claim 14 words
A process according to claim 1 in which the selective deacetylating agent is ammonia.
Claim 6
Dependent Claim 14 words
A process according to claim 1 in which the selective deacetylating agent is water.
Claim 7
Dependent Claim 21 words
A process according to claim 1 in which the selective deacetylating agent is an alcohol having 1 to 24 carbon atoms.
Claim 8
Dependent Claim 24 words
A process according to claim 1 in which an acidic catalyst is used in at least one of the second, third, and fourth steps.
Claim 9
Dependent Claim 24 words
A process according to claim 1 in which an alkaline catalyst is used in at least one of the second, third, and fourth steps.
Claim 10
Dependent Claim 22 words
A process according to claim 1 in which the selective deacetylating agent is a solution of ammonia in isopropyl alcohol and water.
Claim 11
Dependent Claim 96 words
A process for producing a mercaptoalkane-1,2-dicarboxylic acid having 2 to 3 carbon atoms in the alkane group comprising the steps of forming a reaction mixture comprising hydrogen sulfide, acetic anhydride, and an alkene-1,2-dicarboxylic acid compound selected from the group consisting of alkene-1,2-dicarboxylic acids, alkene-1,2-dicarboxylic anhydrides, and alkene-1,2-dicarboxylic esters; heating the reaction mixture at 30° to 230° C. to form an S-acetylthio-1,2-alkanedicarboxylic acid compound in the reaction mixture; heating the reaction mixture comprising S-acetylthioalkane-1,2-dicarboxylic acid compound with a selective deacetylating agent to form a mercaptoalkane-1,2-dicarboxylic acid in the mixture; and recovering mercapto-1,2-alkanedicarboxylic acid from the reaction mixture.
Claim 12
Dependent Claim 96 words
A process for producing a mercaptoalkane-1,2-dicarboxylic acid having 2 to 3 carbon atoms in the alkane group comprising the steps of forming a reaction mixture comprising hydrogen sulfide, acetic anhydride, and an alkene-1,2-dicarboxylic acid compound selected from the group consisting of alkene-1,2-dicarboxylic acids, alkene-1,2-dicarboxylic anhydrides, and alkene-1,2-dicarboxylic esters; heating the reaction mixture at 30° to 230° C. to form an S-acetylthio-1,2-alkanedicarboxylic acid compound in the reaction mixture; heating the reaction mixture comprising S-acetylthioalkane-1,2-dicarboxylic acid compound with a selective deacetylating agent to form a mercaptoalkane-1,2-dicarboxylic acid in the mixture; and recovering mercapto-1,2-alkanedicarboxylic acid from the reaction mixture.
Claim 13
Dependent Claim 14 words
A process according to claim 10 in which the mercaptoalkane-1,2-dicarboxylic acid is thiomalic acid.
Claim 14
Dependent Claim 18 words
A process according to claim 10 in which the selective deacetylating agent comprises water and an acidic catalyst.

References Cited (Backward Citations)

GB542641A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-10-22 1983-04-23 1983-10-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-10-22 1987-04-23 1987-10-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-10-22 1991-04-23 1991-10-23 $7700.00 Window Closed / Lapsed

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