GB1081789A - Transesterification process - Google Patents
Transesterification processInfo
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000005809 transesterification reaction Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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.
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)
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 |
-
1966
- 1966-07-26 CH CH1080966A patent/CH471769A/en not_active IP Right Cessation
- 1966-08-01 DE DE19661543644 patent/DE1543644A1/en active Pending
- 1966-08-01 AT AT739066A patent/AT267509B/en active
- 1966-08-01 NL NL6610810A patent/NL6610810A/xx unknown
- 1966-08-01 BE BE684921D patent/BE684921A/xx unknown
- 1966-08-01 GB GB3438466A patent/GB1081789A/en not_active Expired
- 1966-08-01 ES ES0329760A patent/ES329760A1/en not_active Expired
Cited By (11)
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 |
---|---|
DE1543644A1 (en) | 1969-09-11 |
NL6610810A (en) | 1967-02-03 |
CH471769A (en) | 1969-04-30 |
BE684921A (en) | 1967-02-01 |
AT267509B (en) | 1969-01-10 |
ES329760A1 (en) | 1967-09-01 |
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