GB1081789A - Transesterification process - Google Patents

Transesterification process

Info

Publication number
GB1081789A
GB1081789A GB3438466A GB3438466A GB1081789A GB 1081789 A GB1081789 A GB 1081789A GB 3438466 A GB3438466 A GB 3438466A GB 3438466 A GB3438466 A GB 3438466A GB 1081789 A GB1081789 A GB 1081789A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
reaction
equal
formula
hydroxyphenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3438466A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
National Starch and Chemical Investment Holding Corp
Original Assignee
JR Geigy AG
National Starch and Chemical Investment Holding Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JR Geigy AG, National Starch and Chemical Investment Holding Corp filed Critical JR Geigy AG
Publication of GB1081789A publication Critical patent/GB1081789A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids

Abstract

The invention relates to a process for the preparation of compounds of the general formula <FORM:1081789/C2/1> which comprises treating at least a molar equivalent of an ester of the formula <FORM:1081789/C2/2> with an alkanol of the formula [HO]n-R in, e.g., pentaerythritol, ethylene glycol, neopentyl glycol or 1,1,1-trimethylolpropane, in the presence of an effective amount of a lower, e.g. sodium or lithium, alkoxide of an alkaline metal at a temperature from 80 DEG to 200 DEG C. at a pressure at least as low as the vapour pressure at the reaction temperature of the lower alkanol formed during the reaction, where n is 1 to 6 and R is a non-hydroxylated radical having a valence equal to n and being a straight or branch chain aliphatic hydrocarbon containing from 1 to 30 carbon atoms, cycloaliphatic hydrocarbons containing from about 5 to about 7 carbon atoms and straight and branch chain aliphatic mercaptohydrocarbons containing from 4 to 40 carbon atoms and from 1 to 3 non-terminal sulphide links, the group R in each case containing a number of carbon atoms at least equal to the valence n. In an example methyl 3-[3,5-di-t.-butyl-4-hydroxyphenyl]propionate and pentaerythritol were heated together under a nitrogen atmosphere and an initial portion of sodium methoxide catalyst was added, and as the reaction progressed, five equal portions of catalyst were added during the transesterification reaction, to produce tetra-[3-(3,5-di-t.-butyl-4-hydroxyphenyl)propionyloxymethyl] -methane.
GB3438466A 1965-08-02 1966-08-01 Transesterification process Expired GB1081789A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US47675265A 1965-08-02 1965-08-02

Publications (1)

Publication Number Publication Date
GB1081789A true GB1081789A (en) 1967-08-31

Family

ID=23893116

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3438466A Expired GB1081789A (en) 1965-08-02 1966-08-01 Transesterification process

Country Status (7)

Country Link
AT (1) AT267509B (en)
BE (1) BE684921A (en)
CH (1) CH471769A (en)
DE (1) DE1543644A1 (en)
ES (1) ES329760A1 (en)
GB (1) GB1081789A (en)
NL (1) NL6610810A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017614A1 (en) * 1979-03-09 1980-10-15 Ciba-Geigy Ag Process for the preparation of esters of mercaptoalcanols with hydroxyphenylcarboxylic acids
US4536593A (en) * 1982-07-13 1985-08-20 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters
US4594444A (en) * 1983-12-22 1986-06-10 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters
US4716244A (en) * 1985-05-02 1987-12-29 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters
US4739102A (en) * 1986-04-30 1988-04-19 Ciba-Geigy Corporation Individual beta-form crystals of terakis-(3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionyloxymethyl)-methane and process for its manufacture
US5089655A (en) * 1988-09-07 1992-02-18 Yoshitomi Pharmaceutical Industries, Ltd. Individual α-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane and process for its production
US5117040A (en) * 1989-06-08 1992-05-26 Yoshitomi Pharmaceutical Industries, Ltd. Alpha crystals of tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxymethyl]methane which have good flowability and method of producing same
US6878843B2 (en) 2000-06-23 2005-04-12 Ciba Specialty Chemicals Corp. Method for preparing hydroxyphenyl carboxylic acid esters
CN112694446A (en) * 2020-12-22 2021-04-23 利安隆（中卫）新材料有限公司 Preparation method of benzotriazole ultraviolet absorbent
CN114341246A (en) * 2019-07-08 2022-04-12 弗劳恩霍夫应用研究促进协会 Use of a phenol-substituted sugar derivative as a stabilizer, a plastic composition, a method of stabilizing a plastic material and a phenol-substituted sugar derivative

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017614A1 (en) * 1979-03-09 1980-10-15 Ciba-Geigy Ag Process for the preparation of esters of mercaptoalcanols with hydroxyphenylcarboxylic acids
US4536593A (en) * 1982-07-13 1985-08-20 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters
US4594444A (en) * 1983-12-22 1986-06-10 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters
US4716244A (en) * 1985-05-02 1987-12-29 Ciba-Geigy Corporation Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters
US4739102A (en) * 1986-04-30 1988-04-19 Ciba-Geigy Corporation Individual beta-form crystals of terakis-(3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionyloxymethyl)-methane and process for its manufacture
US5089655A (en) * 1988-09-07 1992-02-18 Yoshitomi Pharmaceutical Industries, Ltd. Individual α-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane and process for its production
US5117040A (en) * 1989-06-08 1992-05-26 Yoshitomi Pharmaceutical Industries, Ltd. Alpha crystals of tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxymethyl]methane which have good flowability and method of producing same
US6878843B2 (en) 2000-06-23 2005-04-12 Ciba Specialty Chemicals Corp. Method for preparing hydroxyphenyl carboxylic acid esters
CZ301602B6 (en) * 2000-06-23 2010-04-28 Ciba Specialty Chemicals Holding Inc. Process for preparing esters of hydroxyphenylcarboxylic acids
CN114341246A (en) * 2019-07-08 2022-04-12 弗劳恩霍夫应用研究促进协会 Use of a phenol-substituted sugar derivative as a stabilizer, a plastic composition, a method of stabilizing a plastic material and a phenol-substituted sugar derivative
CN112694446A (en) * 2020-12-22 2021-04-23 利安隆（中卫）新材料有限公司 Preparation method of benzotriazole ultraviolet absorbent

Also Published As

Publication number Publication date
CH471769A (en) 1969-04-30
BE684921A (en) 1967-02-01
DE1543644A1 (en) 1969-09-11
NL6610810A (en) 1967-02-03
AT267509B (en) 1969-01-10
ES329760A1 (en) 1967-09-01

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