US4091225A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antioxidant ester substituted phenols and process for their preparation
Assignee: Goodyear Tire and Rubber Co
•
Filing: 1974-01-22
•
Granted: 1978-05-23
•
Expires: 1994-01-22
Abstract
Abstract This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.
Inventors
- 👤 Dane K. Parker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 18:02
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C37/00; C07C37/001; C07C37/002; C07C67/00; C07C67/03; C09; C09K; C09K15/00; C09K15/04; C09K15/06; C09K15/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
260 words
A process comprising (a) reacting in an inert atmosphere a compound having the general structural formula ##STR9## with a compound having the general formula ##STR10## in the presence of a basic catalyst while dissolved in an organic solvent to yield an aldehyde having the structural formula ##STR11## (b) separating and reducing the aldehyde to form an alcohol having the general structural formula ##STR12## (c) separating the alcohol and reacting it with an ester forming compound selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate and a compound of the general formula ##STR13## while in the presence of a transesterification catalyst to yield (d) an ester with the structural formula ##STR14## wherein R 1 and R 2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R 3 is selected from the group consisting of hydrogen, methyl and ethyl, A is selected from the group consisting of chloro and bromo, R 4 and R 5 are the same or different radicals selected from the group consisting of methyl, ethyl, n-propyl and n-butyl and R 6 is selected from the group consisting of methyl, ethyl, propyl and butyl, aralkyl radicals having from 7 to 12 carbon atoms, vinyl, 2-propenyl and aryl radicals having the general formula ##STR15## wherein X is selected from the group consisting of hydrogen, amino, nitro, chloro, bromo and alkyl radicals having from 1 to 17 carbon atoms and wherein R 7 is an alkyl radical having from 1 to 10 carbon atoms.
Claim 2
Dependent Claim
260 words
A process comprising (a) reacting in an inert atmosphere a compound having the general structural formula ##STR9## with a compound having the general formula ##STR10## in the presence of a basic catalyst while dissolved in an organic solvent to yield an aldehyde having the structural formula ##STR11## (b) separating and reducing the aldehyde to form an alcohol having the general structural formula ##STR12## (c) separating the alcohol and reacting it with an ester forming compound selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate and a compound of the general formula ##STR13## while in the presence of a transesterification catalyst to yield (d) an ester with the structural formula ##STR14## wherein R 1 and R 2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R 3 is selected from the group consisting of hydrogen, methyl and ethyl, A is selected from the group consisting of chloro and bromo, R 4 and R 5 are the same or different radicals selected from the group consisting of methyl, ethyl, n-propyl and n-butyl and R 6 is selected from the group consisting of methyl, ethyl, propyl and butyl, aralkyl radicals having from 7 to 12 carbon atoms, vinyl, 2-propenyl and aryl radicals having the general formula ##STR15## wherein X is selected from the group consisting of hydrogen, amino, nitro, chloro, bromo and alkyl radicals having from 1 to 17 carbon atoms and wherein R 7 is an alkyl radical having from 1 to 10 carbon atoms.
Claim 3
Dependent Claim
127 words
Compounds having the general formula ##STR16## wherein R 1 and R 2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R 3 is selected from the group consisting of hydrogen, methyl and ethyl, R 4 and R 5 are the same or different radicals selected from the group consisting of methyl, ethyl, n-propyl and n-butyl and R 6 is selected from the group consisting of methyl, ethyl, propyl and butyl, aralkyl radicals having from 7 to 12 carbon atoms, vinyl, 2-propenyl and aryl radicals having the general formula ##STR17## wherein X is selected from the group consisting of hydrogen, amino, nitro, chloro, bromo and alkyl radicals having from 1 to 17 carbon atoms.
Claim 4
Dependent Claim
127 words
Compounds having the general formula ##STR16## wherein R 1 and R 2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R 3 is selected from the group consisting of hydrogen, methyl and ethyl, R 4 and R 5 are the same or different radicals selected from the group consisting of methyl, ethyl, n-propyl and n-butyl and R 6 is selected from the group consisting of methyl, ethyl, propyl and butyl, aralkyl radicals having from 7 to 12 carbon atoms, vinyl, 2-propenyl and aryl radicals having the general formula ##STR17## wherein X is selected from the group consisting of hydrogen, amino, nitro, chloro, bromo and alkyl radicals having from 1 to 17 carbon atoms.
Claim 5
Dependent Claim
22 words
A process as described in claim 1 wherein the solvent is selected from the group consisting of benzene, toluene, xylene and cyclohexane.
Claim 6
Dependent Claim
33 words
A process as described in claim 1 above wherein compounds having the general formula (I) are selected from the group consisting of 3,5-di-t-butyl-4-hydroxy-benzyl chloride; 3,5-di-t-butyl-4-hydroxy-benzyl bromide; α-methyl-3,5-di-t-butyl-4-hydroxy-benzyl chloride; α-methyl-3,5-di-t-butyl-4-hydroxy-benzyl bromide; and 3,5-di-t-hexyl-4-hydroxy-benzyl chloride.
Claim 7
Dependent Claim
31 words
A process as described in claim 1 above wherein compounds having the general structural formula (II) are selected from the group consisting of isobutyraldehyde; for; 2-ethyl hexanal; 2-ethyl butyraldehyde; 2-methyl butyraldehyde.
Claim 8
Dependent Claim
32 words
A process as described in claim 1 wherein compounds having the general formula (V) are selected from the group consisting of methyl methacrylate, methyl acrylate, methyl benzoate, methyl isobutyrate and ethyl acetate.
Claim 9
Dependent Claim
25 words
A process as described in claim 1 wherein the transesterification catalyst is selected from the group consisting of tetraisopropyl titanate, tetrabutyl titanate, and polyisopropyl titanate.
Claim 10
Dependent Claim
14 words
A process as described in claim 1 wherein the compound produced is 2,2-dimethyl-3-(3,5-di-t-butyl-4-hydroxy-phenyl)propyl methacrylate.
Claim 11
Dependent Claim
14 words
A process as described in claim 1 wherein the compound produced is 2,2-dimethyl-3-(3,5-di-t-butyl-4-hydroxy-phenyl)propyl acetate.
References Cited (Backward Citations)
US2822348A
Cited
US2683721A
Cited
US3085003A
Cited
US3116305A
Cited
US3644482A
Cited
GB1283103A
Cited
US3649667A
Cited
BE817837A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |