GB646968A - Improvements in the manufacture of esters of aromatic dicarboxylic acids - Google Patents
Improvements in the manufacture of esters of aromatic dicarboxylic acidsInfo
- Publication number
- GB646968A GB646968A GB448348A GB448348A GB646968A GB 646968 A GB646968 A GB 646968A GB 448348 A GB448348 A GB 448348A GB 448348 A GB448348 A GB 448348A GB 646968 A GB646968 A GB 646968A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methanol
- hydroxy compound
- mono
- anhydride
- per cent
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In the preparation of a di-ester of an aromatic dicarboxylic acid with a distillable aliphatic mono-hydroxy compound by reaction between the anhydride of the acid and the hydroxy compound in presence of an esterification catalyst, the quantity of hydroxy compound is limited so as to avoid substantial reduction in conversion, based on the hydroxy compound, below the peak conversion obtainable and the di-ester and mono-ester produced are separately recovered, and the mono-ester is employed as part of a further batch together with fresh anhydride and hydroxy compound. Di-esters of phthalic acid and hydrogenated phthalic acids such as di-and tetra-hydrophthalic acids with methanol, ethanol, propanols, butanols and glycol ethers such as ethylene glycol mono-methyl ether are referred to. For dimethyl phthalate, the amount of methanol used is at most twice the theoretical, generally less than 50, e.g. 20-30 per cent excess over the theoretical. About 1-3 per cent of sulphuric acid, based on the weight of phthalic anhydride, is suitable. Other acid substances such as sodium bisulphate may be used. The anhydride may first be heated with the theoretical amount of methanol, e.g. at 90-100 DEG C. for up to 3 hours, unchanged methanol distilled off by raising the temperature 10-30 DEG C., and additional methanol then added slowly with distillation of water and some methanol. Recycled mono-methyl phthalate, e.g. 30-35 moles per cent of the anhydride, reduces the amount of methanol used after the first batch. The reaction product is washed with aqueous alkali such as 10-30 per cent caustic soda to separate dimethyl phthalate from an aqueous layer which is acidified to give monomethyl phthalate for recycling. Reduced pressure may be used for distilling water and excess hydroxy compound where the latter is glycol mono-methyl ether. Aqueous alcohols, e.g. 90-95 per cent ethanol, may be used. Examples describe the preparation of dimethyl and diethyl phthalates. Specification 625,203 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB448348A GB646968A (en) | 1948-02-16 | 1948-02-16 | Improvements in the manufacture of esters of aromatic dicarboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB448348A GB646968A (en) | 1948-02-16 | 1948-02-16 | Improvements in the manufacture of esters of aromatic dicarboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB646968A true GB646968A (en) | 1950-11-29 |
Family
ID=9778024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB448348A Expired GB646968A (en) | 1948-02-16 | 1948-02-16 | Improvements in the manufacture of esters of aromatic dicarboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB646968A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1026299B (en) * | 1954-09-30 | 1958-03-20 | Usines De Melle S A | Process for stabilizing esters used as plasticizers |
| WO2004078699A1 (en) * | 2003-03-05 | 2004-09-16 | Council Of Scientific And Industrial Research | Method of producing dimethyl phthalate from naphthalene based chemicals |
| CN111574363A (en) * | 2020-05-26 | 2020-08-25 | 杭州潜阳科技有限公司 | Production process of dimethyl phthalate |
-
1948
- 1948-02-16 GB GB448348A patent/GB646968A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1026299B (en) * | 1954-09-30 | 1958-03-20 | Usines De Melle S A | Process for stabilizing esters used as plasticizers |
| WO2004078699A1 (en) * | 2003-03-05 | 2004-09-16 | Council Of Scientific And Industrial Research | Method of producing dimethyl phthalate from naphthalene based chemicals |
| CN111574363A (en) * | 2020-05-26 | 2020-08-25 | 杭州潜阳科技有限公司 | Production process of dimethyl phthalate |
| CN111574363B (en) * | 2020-05-26 | 2023-09-26 | 杭州潜阳科技有限公司 | Production process of dimethyl phthalate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2491660A (en) | Preparation of esters of terephthalic acid | |
| US2010154A (en) | Ether acid ester of polyhydric alcohols | |
| GB646968A (en) | Improvements in the manufacture of esters of aromatic dicarboxylic acids | |
| US2875244A (en) | Dicarboxylic acids from dicyclopentadienes | |
| US3652652A (en) | 3-methallyllevulinates and preparation thereof | |
| US1706639A (en) | Alkoxy esters of polybasic organic acids | |
| US2714602A (en) | Hydroxylation of vinylcyclohexene | |
| US2618651A (en) | Preparation of dimethyl and diethyl phthalate from phthalic anhydride | |
| US2578647A (en) | Method of preparing esters of 1, 2, 4-butanetriol | |
| US2816921A (en) | Production of alpha-alkoxy alkanoic acids | |
| US2466738A (en) | Reaction of enol esters with anhydrides | |
| GB953775A (en) | Processes for the preparation of sorbic acid and alkyl esters of sorbic acid | |
| GB625203A (en) | Improvements in or relating to the manufacture of aliphatic diesters of aromatic dicarboxylic acids | |
| US2014310A (en) | Esters of 2-butyloctanol | |
| DE1618861B2 (en) | PROCESS FOR MANUFACTURING UNSATATULATED ESTERAL ALCOHOLS | |
| US2782224A (en) | Production of terephthalic acid and esters | |
| US2020356A (en) | Process for the manufacture of dicarboxylic acid esters | |
| US2374484A (en) | Esters of nitrohydroxy compounds | |
| GB418723A (en) | A manufacture of primary diterpene-alcohols | |
| US1999976A (en) | Process for the preparation of higher alkyl esters of the carboxylic acids | |
| GB643033A (en) | Improvements in or relating to high boiling esters of unsaturated aliphatic alcoholsand process of preparing same | |
| US2025947A (en) | Composition of matter and method of producing | |
| DE838000C (en) | Process for the preparation of carboxylic acid esters of aliphatic ªÏ-chloro alcohols | |
| US2468762A (en) | Acylation of aromatic alkoxy compounds | |
| GB654842A (en) | Improvements in or relating to the production of mixed esters of dicarboxylic acids |