GB797270A - Improvements in transesterification catalysts - Google Patents
Improvements in transesterification catalystsInfo
- Publication number
- GB797270A GB797270A GB39609/56A GB3960956A GB797270A GB 797270 A GB797270 A GB 797270A GB 39609/56 A GB39609/56 A GB 39609/56A GB 3960956 A GB3960956 A GB 3960956A GB 797270 A GB797270 A GB 797270A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- methyl
- methylene
- butyl
- butylphenol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Transesterification reactions are catalysed by a phenol represented by either of the formul <FORM:0797270/IV (b)/1> and <FORM:0797270/IV (b)/2> where R1 is alkyl, cycloalkyl or aryl; R2 and R3 each are hydrogen, alkyl, cycloalkyl or aryl; and R4 is alkylene, cycloalkylene or arylene. The proportion of catalyst generally ranges from about 0.1 to about 5 per cent based on the weight of the carboxylic acid used to prepare the ester. Phenols specified include: 2,21-methylene - bis - (4 - methyl - 6 - t - butylphenol); 2,21 - methylene - bis - (4 - ethyl - 6 - t - butyl - phenol); 2,4 - dinonylphenol; 2,6 - dinonyl-phenol; 2,4,6 - trinonylphenol; 2,6 - di - t - butyl 4 - cresol; 2,4 - didodecylphenol; bis-(2-hydroxy - 3 - t - butyl - 5 - methylbenzyl) durene; 2,6 - dicyclohexyl - 4 - cresol; 2 - cyclohexylphenol; 2,21 - methylene - bis - (6 - cyclopentylphenol); 2,21 - methylene - bis - (4 - methyl-6-cyclopentylphenol); 2 - phenylphenol; 2,6-diphenyl - 4 - cresol; 2,21 - propylene - bis - (4-methyl - 6 - phenylphenol); 2,4 - dinonyl - 6 - methylphenol; 2,4 - di - t - butyl - 6 - methylphenol. In Example (2) n-hexyl stearate is prepared by reacting methyl stearate with n-hexanol in the presence of 2,21-methylene-bis-(4 - methyl - 6 - t - butylphenol. In Example (1) bis-(b -hydroxyethyl) adipate is prepared from adipic acid and ethylene glycol conventionally prior to conversion to a polyester by the process of the invention (see Group IV (a)).ALSO:Polyesters are prepared from esters of dicarboxylic or polycarboxylic acids with glycols or polyhydroxy compounds using as catalyst a phenol represented by either of the formulae <FORM:0797270/IV (a)/1> where R1 is alkyl, cycloalkyl or aryl; R2 and R3 each are hydrogen, alkyl, cycloalkyl or aryl; and R4 is alkylene, cycloalkylene or arylene. The proportion of catalyst is generally about 0.1 to 5 per cent based on the weight of the carboxylic acid used to prepare the ester. Phenols specified include: 2,21 - methylene - bis (4 - methyl - 6 - t - butylphenol); 2,21 - methylbis - (4 - ethyl - 6 - t - butylphenol); 2,4-dinonylphenol; 2,6 - dinonylphenol; 2,4,6-trinonylphenol; 2,6 - di - t - butyl - 4 - cresol; 2,4-didodecylphenol: bis - (2 - hydroxy - 3 - t - butyl5 - methylbenzyl) durene; 2,6 - dicyclohexyl-4-cresol; 2 - cyclohexylphenol; 2,21 - methylene-bis - (4 - methyl - 6 - cyclopentylphenol); 2,21-methylene - bis - (6 - cyclopentylphenol); 2-phenolphenol; 2,6 - diphenyl - 4 - cresol; 2,21-propylene - bis - (4 - methyl - 6 - phenylphenol); 2,4 - dinonyl - 6 - methylphenol; 2,4 - di - t - butyl - 6 - methylphenol. Dicarboxylic acids which may be used in the starting material esters are succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dilinoleic, octadecanedicarboxylic acid, phthalic, maleic, fumaric and derivatives such as -ethylsuberic or a ,a 1-diethyl adipic acid. Polycarboxylic acids include tricarballylic, aconitic, citric and linoleic. Suitable glycols include ethylene, propylene, butylene, pentylene, 2,2-dimethyl-1,3-propylene, hexylene, dilinoleyl and 1,12-octadecylene glycols. Polyhydroxy compounds, such as glycerol, sorbitol, pentaerythritol and triethanolamine may be used and also alkylene oxide polymers, such as diethylene, triethylene, dipropylene, polyethylene, polypropylene, polybutylene glycols and poly - 3 - chloro-1,2-propylene ether glycol. In examples, polyesters are prepared from: (1) - bis - (b - hydroxyethyl) adipate using as catalysts 2,21-methylene - bis - (4 - methyl - 6 - t - butylphenol), a mixture of dinonyl- and trinonylphenol, and 2,6 - di - t - butyl - 4 - methylphenol; (4) a reaction product of adipic acid, diethylene glycol and 2 - methylol - 2 - methyl - 1,3 - propanediol using 2,21 - methylene - bis - (4 - methyl - 6 - t - butylphenol) as catalyst.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US797270XA | 1956-04-09 | 1956-04-09 | |
US1164109XA | 1956-04-09 | 1956-04-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB797270A true GB797270A (en) | 1958-06-25 |
Family
ID=26762365
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB39609/56A Expired GB797270A (en) | 1956-04-09 | 1956-12-31 | Improvements in transesterification catalysts |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1164109A (en) |
GB (1) | GB797270A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3179530A (en) * | 1961-04-26 | 1965-04-20 | Pittsburgh Plate Glass Co | Catalyst systems for alkyd resins |
CN115612076A (en) * | 2022-10-14 | 2023-01-17 | 金华市龙达塑胶助剂有限公司 | Medical PVC sheet lubricant and preparation process thereof |
-
1956
- 1956-12-31 GB GB39609/56A patent/GB797270A/en not_active Expired
-
1957
- 1957-01-09 FR FR1164109D patent/FR1164109A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3179530A (en) * | 1961-04-26 | 1965-04-20 | Pittsburgh Plate Glass Co | Catalyst systems for alkyd resins |
CN115612076A (en) * | 2022-10-14 | 2023-01-17 | 金华市龙达塑胶助剂有限公司 | Medical PVC sheet lubricant and preparation process thereof |
Also Published As
Publication number | Publication date |
---|---|
FR1164109A (en) | 1958-10-06 |
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