GB770224A - Improvements in or relating to the preparation of terephthalic acid - Google Patents
Improvements in or relating to the preparation of terephthalic acidInfo
- Publication number
- GB770224A GB770224A GB32987/54A GB3298754A GB770224A GB 770224 A GB770224 A GB 770224A GB 32987/54 A GB32987/54 A GB 32987/54A GB 3298754 A GB3298754 A GB 3298754A GB 770224 A GB770224 A GB 770224A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diacetylbenzene
- oxidized
- oxygen
- acid
- catalyst
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Terephthalic acid is prepared by oxidizing in the liquid phase p-diacetylbenzene or a mixture of p-diacetylbenzene with a minor proportion of one or more other substances, with oxygen or an oxygen-containing gas in the presence of a saturated aliphatic carboxylic acid containing from 2 to 8 carbon atoms per molecule and a catalyst comprising a compound of a metal capable of exhibiting variable valency characteristics. The diacetylbenzene may be prepared by oxidizing p-di-alkyl-benzenes such as p-diethyl-benzene, p-di-sec.-butylbenzene, or p-di-isopropylbenzene, with oxygen or an oxygen-containing gas in the presence of a catalyst comprising a compound of a metal capable of exhibiting variable valency characteristics. Both oxidations may be continuous. p-Diacetylbenzene is oxidized by passing the oxidizing gas such as oxygen or air into a solution consisting of p-diacetylbenzene dissolved in the ratio of from 10 : 1 to 1 : 20 by weight in a saturated aliphatic carboxylic acid such as acetic, propionic or butyric acid, and containing the catalyst which is a manganese compound such as manganese acetate in the proportion of from 0.1 to 5 per cent by weight of the p-diacetylbenzene. A promoter such as barium acetate may be present. The reaction is conducted at from 90 DEG to 180 DEG C. under atmospheric pressure or at from 120 DEG to 300 DEG C. under pressures from 10 to 45 kg/sq. cm. The terephthalic acid with some catalyst precipitates from the reaction mixture is filtered off and the filtrate containing p-diacetylbenzene and p-acetylbenzoic acid is recycled. The p-diacetylbenzene is prepared by passing the oxidizing gas such as oxygen or air into p-di-isopropylbenzene or its solution in a hydrocarbon such as tert.-butyl-benzene or in a halogenated hydrocarbon such as monochlorobenzene, in the presence of the catalyst which may be a cobalt compound such as cobalt naphthenate or cobalt acetate or a manganese compound, at atmospheric pressure between 90 DEG and 150 DEG C. or at superatmospheric pressure. Crude p-diacetylbenzene crystallizes from the reaction mixture on cooling, is filtered off and the filtrate containing p-di-isopropylbenzene and p-isopropylacetylbenzene may be recycled or large amounts of p-isopropylacetylbenzene may be separately oxidized to diacetylbenzene. The reaction products may also be separated by distillation. The crude p-diacetylbenzene which may contain catalyst may be purified before further oxidation by recrystallization or by complex formation with orthophosphoric acid. In a modified process, p-di-isopropylbenzene is oxidized to terephthalic acid in the two stages described but without isolation of the p-diacetylbenzene. Thus p-di-isopropylbenzene is oxidized as before but a saturated aliphatic carboxylic acid containing 2 to 8 carbon atoms per molecule is used as solvent, when the p-diacetylbenzene does not separate from the reaction mixture. The catalyst for the oxidation of p-diacetylbenzene is added and the mixture oxidized as described, the terephthalic acid precipitating from the mixture as before. In examples: (1) portions of p-di-isopropylbenzene are oxidized by air at various flow-rates and temperatures without a solvent and in the presence of cobalt naphthenate with stirring for various reaction times and the products separated by distillation to give p-diacetylbenzene, the p-isopropylacetylbenzene fractions being combined and oxidized with air and a cobalt naphthenate catalyst to p-diacetyl benzene, the combined p-diacetylbenzene products dissolved in propionic acid with manganese acetate and air passed through to give p-acetylbenzoic acid and terephthalic acid with some formaldehyde; (2) p-di-isopropylbenzene is oxidized with oxygen in the presence of cobalt naphthenate to give p-isopropylacetylbenzene and p - diacetylbenzene which is oxidized as in (1) above to p-acetylbenzoic acid and terephthalic acid; (3) p-diisopropylbenzene is dissolved in propionic acid and cobalt acetate added, oxygen is passed through until absorption has ceased when manganese acetate is added and oxygen passed through the mixture to give terephthalic acid. Specification 737,439 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL770224X | 1953-11-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB770224A true GB770224A (en) | 1957-03-20 |
Family
ID=19828087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32987/54A Expired GB770224A (en) | 1953-11-17 | 1954-11-15 | Improvements in or relating to the preparation of terephthalic acid |
Country Status (3)
Country | Link |
---|---|
FR (1) | FR1126928A (en) |
GB (1) | GB770224A (en) |
NL (1) | NL182865C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3014961A (en) * | 1958-07-09 | 1961-12-26 | Buna Chem Werke Veb | Process for the preparation of terephthalic acid and isophthalic acid |
-
0
- NL NLAANVRAGE7511054,A patent/NL182865C/xx active
-
1954
- 1954-11-15 FR FR1126928D patent/FR1126928A/en not_active Expired
- 1954-11-15 GB GB32987/54A patent/GB770224A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3014961A (en) * | 1958-07-09 | 1961-12-26 | Buna Chem Werke Veb | Process for the preparation of terephthalic acid and isophthalic acid |
Also Published As
Publication number | Publication date |
---|---|
NL182865C (en) | |
FR1126928A (en) | 1956-12-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB633354A (en) | Process for the production of dibasic carboxylic acids | |
US2723994A (en) | Oxidation of xylene and toluic acid mixtures to phthalic acids | |
US2415800A (en) | Controlled oxidation of alkylated aromatic hydrocarbons | |
US3595908A (en) | Two-step oxidation of paraxylene for the production of terephthalic acid | |
US2746990A (en) | Preparation of terephthalic acid | |
US2452741A (en) | Production of dibasic acids | |
US2376674A (en) | Method for oxidation of aromatic hydrocarbons | |
GB655074A (en) | An improved process for the preparation of terephthalic acid | |
US3406196A (en) | Oxidation of polyalkyl aromatics to polycarboxylic acids | |
GB770224A (en) | Improvements in or relating to the preparation of terephthalic acid | |
US2545870A (en) | Catalytic oxidation of alkyl benzenes to produce aryl alkyl ketones and carbinols | |
US3030413A (en) | Methylated benzene oxidation | |
US3481975A (en) | Method of preparing dicarboxylic acids | |
GB1429471A (en) | Process for the production of phthalic acids | |
US2945058A (en) | Manufacture of crotonic acid | |
US2821551A (en) | Process for production of aromatic carboxylic acids | |
GB1188268A (en) | Processes for the Autoxidation of Substituted Benzenes | |
GB709674A (en) | Oxidation of hydrocarbons | |
US3042722A (en) | Oxidation of cyclic olefins | |
US2673218A (en) | Process for preparing sulfonyl dibenzoic acids and derivatives thereof | |
GB857098A (en) | Improvements in and relating to the oxidation of alkyl substituted aromatic compounds | |
GB1151281A (en) | Process for the Preparation of Benzene Carboxylic Acids | |
GB1423042A (en) | Preparation of monomethyl terephthalate and dimethyl tereph thalate | |
GB343947A (en) | Improvements in or relating to the production of organic compounds containing oxygen | |
GB762849A (en) | Process for the preparation of terephthalic acid |