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US4117017A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparation of thiols using a benzopinacol initiator

Assignee: WR Grace and Co
•
Filing: 1977-04-18
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Granted: 1978-09-26
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Expires: 1997-04-18
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Abstract

Abstract This invention relates to a process for preparing thiols and polythiols by the addition of a thiolcarboxylic acid, e.g., thiolacetic acid, to ethylenically unsaturated compounds in the presence of an initiator comprising a pinacol of the general formula: ##STR1## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy to obtain a thiol ester which is thereafter hydrolyzed to yield the corresponding thiol.

Inventors

  • 👤 Charles Robert Morgan
  • 👤 Richard Wayne Bush

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 09:34
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/12; C07; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C319/00; C07C319/02; C08G75/02; C08G75/04; C08G75/045

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 195 words
The process of forming a primary thiol which comprises reacting at a temperature in the range 50°-150° C an ethylenically unsaturated compound, said unsaturation being in the terminal or pendant position or a combination thereof, with a thiolcarboxylic acid of the general formula: ##STR7## wherein R is phenyl or an alkyl radical containing 1-6 carbon atoms in the presence of 0.01-5% by weight of the ethylenically unsaturated compound and the thiolcarboxylic acid, of an initiator comprising a pinacol of the general formula: ##STR8## wherein R 1 and R 3 are aromatic radicals of the structure --C 6 H 4 Z, where Z is independently selected from the group consisting of H, Cl, Br, I, alkyl, aryl, and alkoxy; and R 2 and R 4 are members independently selected from the group consisting of R 1 and R 3 (as defined above), alkyl, aralkyl, alkoxyalkyl, haloalkyl and R 2 and R 4 together form a cycloalkyl group; and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy to obtain a thiol ester and, thereafter, hydrolyzing said thiol ester with an alkali metal hydroxide to obtain the corresponding primary thiol.
Claim 2
Dependent Claim 195 words
The process of forming a primary thiol which comprises reacting at a temperature in the range 50°-150° C an ethylenically unsaturated compound, said unsaturation being in the terminal or pendant position or a combination thereof, with a thiolcarboxylic acid of the general formula: ##STR7## wherein R is phenyl or an alkyl radical containing 1-6 carbon atoms in the presence of 0.01-5% by weight of the ethylenically unsaturated compound and the thiolcarboxylic acid, of an initiator comprising a pinacol of the general formula: ##STR8## wherein R 1 and R 3 are aromatic radicals of the structure --C 6 H 4 Z, where Z is independently selected from the group consisting of H, Cl, Br, I, alkyl, aryl, and alkoxy; and R 2 and R 4 are members independently selected from the group consisting of R 1 and R 3 (as defined above), alkyl, aralkyl, alkoxyalkyl, haloalkyl and R 2 and R 4 together form a cycloalkyl group; and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy to obtain a thiol ester and, thereafter, hydrolyzing said thiol ester with an alkali metal hydroxide to obtain the corresponding primary thiol.
Claim 3
Dependent Claim 12 words
The process of claim 1 wherein the thiolcarboxylic acid is thiolacetic acid.
Claim 4
Dependent Claim 10 words
The process of claim 1 wherein the pinacol is benzopinacol.

References Cited (Backward Citations)

US2398479A Cited
US2411983A Cited
US2551813A Cited
US3050452A Cited
US3270063A Cited
US3522313A Cited
US3607945A Cited
US3823191A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-09-25 1982-03-27 1982-09-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-09-25 1986-03-27 1986-09-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-09-25 1990-03-27 1990-09-26 $7700.00 Window Closed / Lapsed

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