GB810461A - Production of trichloroacetic acid and its functional derivatives - Google Patents
Production of trichloroacetic acid and its functional derivativesInfo
- Publication number
- GB810461A GB810461A GB19817/55A GB1981755A GB810461A GB 810461 A GB810461 A GB 810461A GB 19817/55 A GB19817/55 A GB 19817/55A GB 1981755 A GB1981755 A GB 1981755A GB 810461 A GB810461 A GB 810461A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- per cent
- parts
- trichloroacetic acid
- mixture
- 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
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Trichloroacetic acid and functional derivatives thereof which are hydrolysable to the acid by reaction with water are prepared by passing gaseous chlorine into a heated mixture of 15 to 75 per cent by weight of glacial acetic acid and 85 to 25 per cent by weight of acetic anhydride until substantially the whole of the reaction mixture has been converted to trichloroacetic acid and said functional derivatives, at least the latter part of the chlorination being carried out in the presence of 0.01 to 2 per cent by weight, calculated on the sum of the weights of glacial acetic acid and acetic anhydride, of an acid of phosphorus. This acid is preferably orthophosphoric acid used in an amount of from 0.01 to 1 per cent, although other phosphorus oxyacids, a list of which is given, can also be used. In a preferred embodiment the acid is present throughout the chlorination but it may equally well be added when about 80 per cent of the reaction mixture has been converted to trichloroacetic acid and derivatives thereof or at the stage when formation of monochloroacetic acid is substantially complete. The process of the invention may be combined with the additional step of adding water to the reaction product at a temperature above the melting point thereof to convert the functional derivatives to trichloroacetic acid, or with the additional step of treating the product with an alkali or with a salt of a weak or easily displaced acid to form a salt of trichloroacetic acid, or with the additional step of esterifying the product. In examples: (1) chlorine is introduced into a mixture of 25 parts of acetic anhydride and 75 parts of glacial acetic acid at 70 DEG to 110 DEG C. until the monochloroacetic acid stage has been reached, the temperature is raised to 150 DEG C. and 85 per cent phosphoric acid is added periodically until the product has a trichloroacetic acid content of 97 to 98 per cent, a figure which may be changed to approximately 100 per cent by addition of water at 100 DEG C. to hydrolyse the functional derivatives (mainly trichloroacetyl chloride); (2) a process similar to (1) is performed, except that the phosphoric acid is present throughout; (3) a mixture of 42 parts of acetic anhydride and 58 parts of glacial acetic acid is converted to trichloroacetic acid by a process similar to (1); (4) a mixture of 60 parts of acetic anhydride and 40 parts of glacial acetic acid is converted to trichloroacetic acid by a process similar to (1), phosphoric acid being added after 90 per cent conversion; (5) a mixture of 85 parts of acetic anhydride and 15 parts of glacial acetic acid is converted to trichloroacetic acid by a procedure similar to (1); (6) the reaction product, prior to hydrolysis, of (2) is heated with soda ash at 60 DEG C. to give sodium trichloroacetate containing a small amount of sodium dichloroacetate, and the preparation of other alkali metal, alkaline earth metal and ammonium salts is also referred to; and (7) the reaction product, prior to hydrolysis, of (2) is heated with isopropyl alcohol to give isopropyl trichloroacetate, and reference is also made to the formation of esters with other saturated or unsaturated, primary, secondary or tertiary, substituted or unsubstituted aliphatic, aromatic or heterocyclic alcohols. Specification 706,440 and U.S.A. Specification 2,674,620 are are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US810461XA | 1954-07-08 | 1954-07-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB810461A true GB810461A (en) | 1959-03-18 |
Family
ID=22161774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19817/55A Expired GB810461A (en) | 1954-07-08 | 1955-07-08 | Production of trichloroacetic acid and its functional derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB810461A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3179562A (en) * | 1961-08-23 | 1965-04-20 | Du Pont | Treatment of diabetes with alpha, alpha substituted acetic acid derivatives |
CN103086870A (en) * | 2011-10-27 | 2013-05-08 | 山西三维丰海化工有限公司 | Novel process for producing trichloro-acetic chloride |
-
1955
- 1955-07-08 GB GB19817/55A patent/GB810461A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3179562A (en) * | 1961-08-23 | 1965-04-20 | Du Pont | Treatment of diabetes with alpha, alpha substituted acetic acid derivatives |
CN103086870A (en) * | 2011-10-27 | 2013-05-08 | 山西三维丰海化工有限公司 | Novel process for producing trichloro-acetic chloride |
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