US4716244A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters
Assignee: BASF Corp
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Filing: 1986-04-21
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Granted: 1987-12-29
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Expires: 2006-04-21
Abstract
Abstract If the transesterification of esters of formula II ##STR1## with alcohols of formula III A--OH) m is catalysed by treatment with catalytic amounts of an organic or inorganic zinc salt and the resultant melt is subsequently distilled in a short-time distillation apparatus under specific conditions, then compounds of the formula ##STR2## are obtained in virtually quantitative yield, in which formulae I, II and III n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, B is methyl or tert-butyl and R is methyl or ethyl. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.
Inventors
- 👤 Ivan Orban
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 08:00
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/02; C07C69/00; C07C69/66; C07C69/73; C07C69/732; C07C67/03; C07C69/76; C07C69/84; C07C69/88; Y; Y10; Y10S; Y10S203/00; Y10S203/06
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
166 words
A process for the preparation of a compound of formula I ##STR5## wherein n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, and B is methyl or tert-butyl, by transesterification of about m moles of an ester of formula II at a temperature of 110° to 220° C. and under a pressure of 1000 to 2 mbar, ##STR6## wherein R is methyl or ethyl, with an alcohol of formula III A--OH).sub.m (III) which process comprises (a) carrying out the transesterification in the presence of an organic or inorganic zinc salt in an amount of 0.05 to 2.0 mol%, based on the ester of formula II, and (b) distilling the resultant melt in a short-time distillation apparatus under a pressure in the range from 0.5 to 6 mbar and at a temperature in the range from 230° to 270° C., and granulating the melt obtained.
Claim 2
Dependent Claim
166 words
A process for the preparation of a compound of formula I ##STR5## wherein n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, and B is methyl or tert-butyl, by transesterification of about m moles of an ester of formula II at a temperature of 110° to 220° C. and under a pressure of 1000 to 2 mbar, ##STR6## wherein R is methyl or ethyl, with an alcohol of formula III A--OH).sub.m (III) which process comprises (a) carrying out the transesterification in the presence of an organic or inorganic zinc salt in an amount of 0.05 to 2.0 mol%, based on the ester of formula II, and (b) distilling the resultant melt in a short-time distillation apparatus under a pressure in the range from 0.5 to 6 mbar and at a temperature in the range from 230° to 270° C., and granulating the melt obtained.
Claim 3
Dependent Claim
12 words
A process according to claim 1, wherein the catalyst is zinc acetate.
Claim 4
Dependent Claim
80 words
A process according to claim 1 for the preparation of a compound of formula I by esterification of an ester of formula II with an alcohol of formula III. in which formulae I, II and III n is 2 and m is 1 or 2, A is C 2 -C 18 alkyl if m is 1, A is a --CH 2 ) 2 O--CH 2 ) 2 O--CH 2 ) 2 group if m is 2, and R is methyl.
Claim 5
Dependent Claim
29 words
A process according to claim 1, which comprises employing the catalyst in the transesterification in an amount of 0.1 to 0.5 mol%, based on the ester of formula II.
Claim 6
Dependent Claim
43 words
A process according to claim 1, which comprises carrying out the distillation of the melt in the short-time distillation apparatus under a pressure in the range from 1 to 3 mbar and at a temperature in the range from 240° to 260° C.
Claim 7
Dependent Claim
20 words
A process according to claim 1 for the preparation of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate by transesterification of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate with stearyl alcohol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-28 | 1991-06-29 | 1991-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-28 | 1995-06-29 | 1995-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-28 | 1999-06-29 | 1999-12-29 | $7700.00 | Window Closed / Lapsed |