GB901271A - Ester preparation - Google Patents
Ester preparationInfo
- Publication number
- GB901271A GB901271A GB32505/59A GB3250559A GB901271A GB 901271 A GB901271 A GB 901271A GB 32505/59 A GB32505/59 A GB 32505/59A GB 3250559 A GB3250559 A GB 3250559A GB 901271 A GB901271 A GB 901271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methanol
- mixture
- polyalkyl
- production
- monomethyl
- 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
- C07C69/78—Benzoic acid esters
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Methyl esters of aromatic polycarboxylic acids are produced by mixing a polyalkyl aromatic hydrocarbon (wherein the alkyl groups contain 1 to 4 carbon atoms) with a molar excess of methanol, and reacting the mixture with molecular oxygen, e.g. in the form of air, in the presence of a catalyst comprising a salt of a polyvalent metal; the reaction being carried out at a temperature of at least 140 DEG C. and under pressure-conditions (200 to 1000 p.s.i.g.) so that the methanol is maintained to a maximum extent in the liquid phase. Preferably 1.5 to 3 mols of methanol should be used per mol-equivalent of alkyl groups to be oxidised. All the methanol need not be added to the fresh feed, but some of it may be introduced during the course of the reaction. The following polyalkyl hydrocarbons may be used as starting materials:-the xylenes, mesitylene, durene, pentamethylbenzene, hexamethylbenzene, the corresponding ethyl-, propyl- and butyl-benzenes, and polyalkyl-substituted di- and tri-benzyls. Suitable catalysts are the naphthenates, acetates, bromides and chlorides of cobalt and manganese. Promoters such as hydrobromic acid, hydrochloric acid, or sulphuric acid may be added. The Specification includes two flow-sheets, one of which illustrates the production of a mixture of dimethyl terephthalate and monomethyl terephthalate by a continuous two-stage process starting with p-xylene. The mixture is then submitted to a conventional esterification process whereby the monomethyl ester is converted into the diester. Example 1 describes the production of a mixture of dimethyl phthalate and monomethyl phthalate from o-xylene. Appreciable quantities of methyl orthotoluate and phthalide are obtained as by-products. Example 3 and 4 describe the production of trimethyl trimesate and dimethyl terephthalate from mesitylene and p-di-isopropyl benzene respectively.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US772500A US3047612A (en) | 1958-11-07 | 1958-11-07 | Ester preparation by oxidation of hydrocarbons |
Publications (1)
Publication Number | Publication Date |
---|---|
GB901271A true GB901271A (en) | 1962-07-18 |
Family
ID=25095275
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32505/59A Expired GB901271A (en) | 1958-11-07 | 1959-09-24 | Ester preparation |
Country Status (4)
Country | Link |
---|---|
US (1) | US3047612A (en) |
DE (1) | DE1418175A1 (en) |
GB (1) | GB901271A (en) |
NL (1) | NL110864C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3399227A (en) * | 1963-07-31 | 1968-08-27 | Standard Oil Co | Recovery of purified dimethyl terephthalate from mother liquor stripper bottoms |
US3944601A (en) * | 1972-12-20 | 1976-03-16 | Standard Oil Company | Quality of phthalic acids improved by strong inorganic acids |
GB1467903A (en) * | 1973-05-28 | 1977-03-23 | Teijin Hercules Chem Co Ltd | Process for the preparation of dimethyl terephthalate |
JPS5095176A (en) * | 1973-12-26 | 1975-07-29 | ||
DE3407925C1 (en) * | 1984-03-03 | 1985-09-05 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of dimethyl terephthalate from p-xylene and methanol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2415800A (en) * | 1945-03-12 | 1947-02-11 | Shell Dev | Controlled oxidation of alkylated aromatic hydrocarbons |
US2833816A (en) * | 1954-05-03 | 1958-05-06 | Mid Century Corp | Preparation of aromatic polycarboxylic acids |
US2879289A (en) * | 1956-06-27 | 1959-03-24 | Du Pont | Oxidation of alkyl benzenes in the presence of alkanols |
-
0
- NL NL110864D patent/NL110864C/xx active
-
1958
- 1958-11-07 US US772500A patent/US3047612A/en not_active Expired - Lifetime
-
1959
- 1959-09-24 GB GB32505/59A patent/GB901271A/en not_active Expired
- 1959-11-04 DE DE19591418175 patent/DE1418175A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
US3047612A (en) | 1962-07-31 |
NL110864C (en) | |
DE1418175A1 (en) | 1968-10-17 |
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