US3989738A
Expired / Lapsed
US
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Method of preparing phenolic antioxidants by condensing active methylene compounds with 3,5-di-tert alkyl-4-hydroxybenzylpyridinium salts
Assignee: Goodyear Tire and Rubber Co
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Filing: 1975-07-21
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Granted: 1976-11-02
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Expires: 1995-07-21
Abstract
Abstract 3,5-Di-tert alkyl-4-hydroxybenzylpyridinium salts are reacted under basic conditions with compounds containing active methylene groups to form phenolic antioxidants. For example, 3,5-di-tert.butyl-4-hydroxybenzylpyridinium chloride is reacted with 2-nitropropane to produce 1,1-dimethyl-2-(3,5-di tert.butyl-4-hydroxyphenyl)-1-nitroethane.
Inventors
- 👤 Richard H. Kline
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 20:50
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; C07C; C07C201/00; C07C201/06; C07C201/12; C07C45/00; C07C45/61; C07C45/67; C07C45/68
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
190 words
A process of producing a phenolic antioxidant comprising reacting in solution, in the presence of a base, a combination comprised of a pyridinium salt having the structure ##SPC3## and an active methylene compound having the structure ##EQU1## wherein R is a tertiary alkyl radical having 4 to 8 carbon atoms, R.sup. 1 is selected from the group consisting of hydrogen, methyl and ethyl and X is a halogen radical selected from the group consisting of chloro, bromo and iodo, wherein R.sup. 5 is selected from the group consisting of hydrogen and alkyl radicals containing 1 to 4 carbon atoms, and wherein R.sup. 2 and R.sup. 3 are selected from the group consisting of --COOR.sup. 4, --COR.sup. 4, --CN and --NO.sub. 2, wherein R.sup. 4 is an alkyl radical containing from 1 to 4 carbon atoms, with the proviso that when R.sup. 2 is NO.sub. 2, R.sup. 3 can also be hydrogen or an alkyl radical containing 1 to 4 carbon atoms, wherein the reaction temperature is from 0° C. to the boiling point of the solvent and wherein the molar ratio of I to II is from 2.5/1 to 1/10.
Claim 2
Dependent Claim
190 words
A process of producing a phenolic antioxidant comprising reacting in solution, in the presence of a base, a combination comprised of a pyridinium salt having the structure ##SPC3## and an active methylene compound having the structure ##EQU1## wherein R is a tertiary alkyl radical having 4 to 8 carbon atoms, R.sup. 1 is selected from the group consisting of hydrogen, methyl and ethyl and X is a halogen radical selected from the group consisting of chloro, bromo and iodo, wherein R.sup. 5 is selected from the group consisting of hydrogen and alkyl radicals containing 1 to 4 carbon atoms, and wherein R.sup. 2 and R.sup. 3 are selected from the group consisting of --COOR.sup. 4, --COR.sup. 4, --CN and --NO.sub. 2, wherein R.sup. 4 is an alkyl radical containing from 1 to 4 carbon atoms, with the proviso that when R.sup. 2 is NO.sub. 2, R.sup. 3 can also be hydrogen or an alkyl radical containing 1 to 4 carbon atoms, wherein the reaction temperature is from 0° C. to the boiling point of the solvent and wherein the molar ratio of I to II is from 2.5/1 to 1/10.
Claim 3
Dependent Claim
53 words
The process according to claim 1 wherein R is a tert.butyl radical, R.sup. 1 is hydrogen, X is C1, R.sup. 2 is COOR.sup. 4 or NO.sub. 2, R.sup. 3 is COOR.sup. 4 or CH.sub. 3, R.sup. 4 is CH.sub. 3 or C.sub. 2 H.sub. 5 and R.sup. 5 is hydrogen or CH.sub. 3.
Claim 4
Dependent Claim
19 words
The process according to claim 1 wherein the molar ratio of I to II is from 1/2 to 1/3.
Claim 5
Dependent Claim
19 words
The process according to claim 1 wherein the molar ratio of I to II is from 2/1 to 2.5/1.
References Cited (Backward Citations)
US3678095A
Cited
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| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
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