US4536593A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters
Assignee: BASF Corp
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Filing: 1983-07-05
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Granted: 1985-08-20
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Expires: 2003-07-05
Abstract
Abstract If the transesterification of esters of the formula ##STR1## with alcohols of the formula III A--(OH) m is catalyzed by successive treatment with catalytic amounts (a) of a tin compound of a metal of the fourth main group or the fourth sub-group of the periodic system and (b) of an acid earth, compounds of the formula I ##STR2## are obtained in virtually quantitative yield. The products thus obtained contain no troublesome by-products and do not have to be additionally purified. R is methyl or ethyl, A is a radical derived from an m-hydric aliphatic alcohol, n is 0 to 2, and m is 1 to 4.
Inventors
- 👤 Ivan Orban
- 👤 Eduard Troxler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:21
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/66; C07C69/73; C07C69/732; C07C69/76; C07C69/84; C07C69/88
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
123 words
A process for the preparation of a compound of formula I ##STR11## in which n is a number from 0 to 2, m is a number from 1 to 4 and A is a radical which has 2 to 18 carbon atoms and is derived from an m-hydric aliphatic alcohol, by transesterifying about m mols of an ester of formula (II) ##STR12## in which R is methyl or ethyl, with an alcohol of formula III A--OH).sub.m (III) which comprises catalysing the transesterification by successive treatment under atmospheric pressure in the presence of an inert solvent with a catalytic amount of (a) a tin compound of formula V ##STR13## in which R 2 is C 4 -C 18 -alkyl, and (b) an acid earth.
Claim 2
Dependent Claim
123 words
A process for the preparation of a compound of formula I ##STR11## in which n is a number from 0 to 2, m is a number from 1 to 4 and A is a radical which has 2 to 18 carbon atoms and is derived from an m-hydric aliphatic alcohol, by transesterifying about m mols of an ester of formula (II) ##STR12## in which R is methyl or ethyl, with an alcohol of formula III A--OH).sub.m (III) which comprises catalysing the transesterification by successive treatment under atmospheric pressure in the presence of an inert solvent with a catalytic amount of (a) a tin compound of formula V ##STR13## in which R 2 is C 4 -C 18 -alkyl, and (b) an acid earth.
Claim 3
Dependent Claim
90 words
The process according to claim 1 for the preparation of a compound of the formula I by transesterifying an ester of the formula II with an alcohol of the formula III, wherein, in the formulae I, II and III, n is the number 2, m is the number 1, 2 or 4; when m is 1, A is C 2 -C 18 -alkyl; when m is 2, A is C 2 -C 6 -alkylene or a ##STR14## group, and; when m is 4, A is pentaerythrityl, and R is methyl.
Claim 4
Dependent Claim
17 words
The process according to claim 1, wherein an acid aluminium silicate is employed as the acid earth.
Claim 5
Dependent Claim
30 words
The process according to claim 1, wherein the tin compound is employed in an amount of not less than 0.03% by weight, based on the ester of the formula II.
Claim 6
Dependent Claim
30 words
The process according to claim 1, wherein the acid earth is employed in an amount of between 0.3 and 6% by weight, based on the ester of the formula II.
Claim 7
Dependent Claim
24 words
The process according to claim 1, wherein the treatment with the tin compound is carried out at a temperature between 130° and 190° C.
Claim 8
Dependent Claim
24 words
The process according to claim 1, wherein the treatment with the acid earth is carried out at a temperature between 50° and 150° C.
Claim 9
Dependent Claim
72 words
The process according to claim 1 for the preparation of octadecyl 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate by transesterifying methyl 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate with octadecanol, which comprises catalysing the transesterification by treatment with (a) 0.25 to 0.5% by weight, based on the methyl 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate, of dibutyl-tin oxide at a temperature between 150° and 175° C. and (b) 1 to 5% by weight, based on the methyl 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate of an aluminium hydrosilicate at a temperature between 90° and 120° C.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-19 | 1989-02-18 | 1989-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-19 | 1993-02-18 | 1993-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-19 | 1997-02-18 | 1997-08-20 | $7700.00 | Window Closed / Lapsed |