GB733322A - Process for the manufacture of polybasic aromatic carboxylic acids - Google Patents
Process for the manufacture of polybasic aromatic carboxylic acidsInfo
- Publication number
- GB733322A GB733322A GB13609/53D GB1360953D GB733322A GB 733322 A GB733322 A GB 733322A GB 13609/53 D GB13609/53 D GB 13609/53D GB 1360953 D GB1360953 D GB 1360953D GB 733322 A GB733322 A GB 733322A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- oxidation
- product
- benzene
- 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
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups
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
Polybasic aromatic carboxylic acids are manufactured, by condensing in known manner benzene or one of its homologues with ethylene chloride in the presence of a Friedel-Craft's catalyst to give a product of high molecular weight, and oxidizing this product to give polybasic carboxylic acids. Aluminium chloride may be used as catalyst, and the chain length of the compounds, in which benzene rings are linked by -CH2-CH2- groups, is dependent on the molecular ratio ethylene chloride: benzene. The chain length increases as the ratio approaches 1, but it is kept below 1 for the production of dicarboxylic acids, and at such a figure that products with an average molecular weight of at least 800 are obtained. The temperature of the reaction is adjusted to give a steady evolution of hydrogen chloride. The reaction product may be oxidized in three ways: (1) with air at 100-150 DEG C. in the presence of a heavy metal catalyst, (2) boiling nitric acid plus vanadic acid as catalyst, (3) bichromate-sulphuric acid mixture at 100-150 DEG C. The acids in the oxidation product can be separated by fractional crystallization, or distillation of esters. Besides minor amounts of benzoic acid, terephthalic and isophthalic acids are obtained. If toluene is used, oxidation of the condensation product yields tricarboxylic acids. A slight excess of ethylene chloride leads to cross-linking between the chains, and to more tricarboxylic acids on oxidation. Further reaction of this condensation product with toluene before oxidation, reduces the formation of benzoic acid and increases the yield of dicarboxylic acids. In examples (1) benzene is condensed with ethylene chloride and a mixture of iso- and terephthalic acids obtained after oxidation with nitric acid, (2) the condensation product from (1) is oxidized with oxygen using cobalt nitrate and copper nitrate as catalysts.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE733322X | 1952-05-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB733322A true GB733322A (en) | 1955-07-06 |
Family
ID=6640549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13609/53D Expired GB733322A (en) | 1952-05-16 | 1953-05-15 | Process for the manufacture of polybasic aromatic carboxylic acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB733322A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7741509B2 (en) | 2007-01-30 | 2010-06-22 | Eastman Chemical Company | Conversion of terephthalic acid to Di-n-butyl terephthalate |
US7799942B2 (en) | 2005-08-12 | 2010-09-21 | Eastman Chemical Company | Production of terephthalic acid di-esters |
-
1953
- 1953-05-15 GB GB13609/53D patent/GB733322A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7799942B2 (en) | 2005-08-12 | 2010-09-21 | Eastman Chemical Company | Production of terephthalic acid di-esters |
US7741509B2 (en) | 2007-01-30 | 2010-06-22 | Eastman Chemical Company | Conversion of terephthalic acid to Di-n-butyl terephthalate |
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