WO2015022707A2 - Process for the synthesis of trifluoromethanesulfonic acid - Google Patents
Process for the synthesis of trifluoromethanesulfonic acid Download PDFInfo
- Publication number
- WO2015022707A2 WO2015022707A2 PCT/IN2014/000527 IN2014000527W WO2015022707A2 WO 2015022707 A2 WO2015022707 A2 WO 2015022707A2 IN 2014000527 W IN2014000527 W IN 2014000527W WO 2015022707 A2 WO2015022707 A2 WO 2015022707A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- trifluoromethanesulfonic acid
- bar
- temperature
- carried out
- reaction mixture
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Definitions
- the present invention provides a process for preparation of trifluoromethanesulfonic acid.
- halogenated compounds such as fluoroalkanesulfonic acids
- the trifluoromethanesulfonic acid derivatives are also used as a component of lithium batteries, thus finds use in various electronic items.
- the Russian Patent No. 2,135,463 patent provides a process for hydrolysis of trifluoromethylsulfonyl fluoride in an aqueous-alcoholic mixture at a temperature of 80°C to 120°C, followed by release of trifluoromethanesulfonic acid in the form of azeotrope with water.
- the azeotrope is treated with oleum, followed by distillation of an anhydrous trifluoromethanesulfonic acid mixture.
- the U.S Patent No. 4,927,962 provides a method to obtain trifluoromethanesulfonic acid by interaction of trifluoromethylsulfonyl fluoride with aqueous potassium hydroxide solution. Further, in addition, the obtained potassium salt of trifluoromethanesulfonic acid requires purification from fluoride ion by treatment with silicon dioxide in sulfuric acid, followed by acid decomposition of selected salt with mixture of 98% H 2 S0 4 and 26% fuming H 2 S0 4 .
- the present invention provides a process for the preparation of trifluoromethanesulfonic acid, comprising; a) treating trifluoromethylsulfonyl fluoride with water, b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 110°C.
- the present invention provides a process for the preparation of trifluoromethanesulfonic acid, comprising: a) treating trifluoromethylsulfonyl fluoride with water , b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 1 10°C.
- the trifluoromethylsulfonyl fluoride may be prepared by any method known in the art, for example, by method known in U.S Patent No. 4,927,962.
- the step a) may be carried out at a temperature of about 60°C to about 110°C, for example, about 75°C to about 100°C, for about 30 minutes to about 120 hours, for example for about 2 hour to about 95 hours.
- the trifluoromethanesulfonic acid may be isolated from step a) reaction mixture by layer separation, distillation, decantation and evaporation or mixture thereof.
- the trifluoromethanesulfonic acid may be further purified by any of the method known in the art.
- the pressure during step a) of the reaction may be increased from about 1 bar to about 7 bar, for example, from about 2 bar to about 6 bar.
- the preparation of trifluoromethanesulfonic acid may be carried out in a continuous mode.
Abstract
The present invention provides a process for preparation of trifluoromethanesulfonic acid.
Description
PROCESS FOR THE SYNTHESIS OF TRIFLUOROMETHANESULFONIC
ACID
FIELD OF THE INVENTION The present invention provides a process for preparation of trifluoromethanesulfonic acid.
BACKGROUND OF THE INVENTION The halogenated compounds, such as fluoroalkanesulfonic acids, have wide applications as super acids mainly in pharmaceutical, agrochemical and fine chemical industries. The trifluoromethanesulfonic acid derivatives are also used as a component of lithium batteries, thus finds use in various electronic items.
The Russian Patent No. 2,135,463 patent provides a process for hydrolysis of trifluoromethylsulfonyl fluoride in an aqueous-alcoholic mixture at a temperature of 80°C to 120°C, followed by release of trifluoromethanesulfonic acid in the form of azeotrope with water. The azeotrope is treated with oleum, followed by distillation of an anhydrous trifluoromethanesulfonic acid mixture.
The U.S Patent No. 4,927,962 provides a method to obtain trifluoromethanesulfonic acid by interaction of trifluoromethylsulfonyl fluoride with aqueous potassium hydroxide solution. Further, in addition, the obtained potassium salt of trifluoromethanesulfonic acid requires purification from fluoride ion by treatment with silicon dioxide in sulfuric acid, followed by acid decomposition of selected salt with mixture of 98% H2S04 and 26% fuming H2S04. Thus, there is still need in the art for a simple, cost effective and commercially viable method for hydrolysis of trifluoromethylsulfonyl fluoride which avoids the prototype
process, organic solvents such as alcoholic solvents, its multistage, the presence of solid and gaseous wastes and the exclusion of formation of salts and solid waste.
OBJECT OF THE INVENTION
It is an object of the present invention to provide process for the preparation of trifluoromethanesulfonic acid, comprising; a) treating trifluoromethylsulfonyl fluoride with water, b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 110°C.
SUMMARY OF THE INVENTION
In an aspect, the present invention provides a process for the preparation of trifluoromethanesulfonic acid, comprising; a) treating trifluoromethylsulfonyl fluoride with water, b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 110°C.
DETAILED DESCRIPTION OF THE INVENTION
In an embodiment, the present invention provides a process for the preparation of trifluoromethanesulfonic acid, comprising:
a) treating trifluoromethylsulfonyl fluoride with water , b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 1 10°C.
The trifluoromethylsulfonyl fluoride may be prepared by any method known in the art, for example, by method known in U.S Patent No. 4,927,962.
The step a) may be carried out at a temperature of about 60°C to about 110°C, for example, about 75°C to about 100°C, for about 30 minutes to about 120 hours, for example for about 2 hour to about 95 hours. The trifluoromethanesulfonic acid may be isolated from step a) reaction mixture by layer separation, distillation, decantation and evaporation or mixture thereof. The trifluoromethanesulfonic acid may be further purified by any of the method known in the art.
The pressure during step a) of the reaction may be increased from about 1 bar to about 7 bar, for example, from about 2 bar to about 6 bar.
Preferably, the preparation of trifluoromethanesulfonic acid may be carried out in a continuous mode.
While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.
EXAMPLES
Example 1
Preparation of Trifluoromethanesulfonic acid
Water (950 g) was taken in the re-boiler and water was circulated at the rate of 6LPH. The circulation rate was increased to 13 LPH. The temperature of column and the re- boiler was raised to 80°C. The trifluoromethylsulfonyl fluoride was added to the reaction vessel at a rate of 10 g/h. In all 91 1 g of trifluoromethylsulfonyl fluoride was added over a period of 90 hours. The trifluoromethanesulfonic acid, so obtained, was isolated from the reaction mixture.
Yield: 22%
Claims
1. A process for the preparation of trifluoromethanesulfonic acid, comprising; a) treating trifluoromethylsulfonyl fluoride with water , b) isolating trifluoromethanesulfonic acid from reaction mixture of step a), wherein step a) is carried out at a temperature of about 60°C to about 110°C.
2. The process of claim 1, wherein step a) is be carried out at a temperature of about 60°C to about 110°C.
3. The process of claim 2, wherein step a) is be carried out at a temperature of about 75°C to about 100°C.
4. The process of claim 1 , wherein pressure during step a) is increased from about
1 bar to about 7 bar.
5. The process of claim 4, wherein pressure during step a) is increased from about
2 bar to about 6 bar.
6. The process of claim 1, wherein trifluoromethanesulfonic acid may be isolated from step a) reaction mixture by layer separation, distillation, decantation, removal and evaporation or mixture thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2433/DEL/2013 | 2013-08-16 | ||
| IN2433DE2013 | 2013-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2015022707A2 true WO2015022707A2 (en) | 2015-02-19 |
| WO2015022707A3 WO2015022707A3 (en) | 2015-04-09 |
Family
ID=52468760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2014/000527 WO2015022707A2 (en) | 2013-08-16 | 2014-08-14 | Process for the synthesis of trifluoromethanesulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2015022707A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358818A (en) * | 2017-11-30 | 2018-08-03 | 江西国化实业有限公司 | A kind of preparation method of trifluoromethanesulfonic acid |
| CN115228105A (en) * | 2022-07-22 | 2022-10-25 | 江西国化实业有限公司 | Safe purification equipment for trifluoromethanesulfonic acid production |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4927962A (en) * | 1987-08-31 | 1990-05-22 | Central Glass Company, Limited | Process of preparing fluorocarbon carboxylic or sulfonic acid from its fluoride |
| DK173212B1 (en) * | 1995-02-14 | 2000-03-27 | Topsoe Haldor As | Process for the preparation of fluorinated sulfonic acids |
| DK173229B1 (en) * | 1995-02-08 | 2000-04-17 | Topsoe Haldor As | Process for the preparation of fluorinated alkylsulfonyl acid compounds by hydrolysis of fluorinated alkylsulfonyl fluoride |
| RU2135463C1 (en) * | 1997-12-16 | 1999-08-27 | Пермский филиал российского научного центра "Прикладная химия" | Method of synthesis of trifluoromethane sulfoacid |
| CN101402591B (en) * | 2008-11-09 | 2012-09-05 | 中国船舶重工集团公司第七一八研究所 | Process for preparing high-purity trifluoromethyl sulphonic acid |
-
2014
- 2014-08-14 WO PCT/IN2014/000527 patent/WO2015022707A2/en active Application Filing
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358818A (en) * | 2017-11-30 | 2018-08-03 | 江西国化实业有限公司 | A kind of preparation method of trifluoromethanesulfonic acid |
| CN115228105A (en) * | 2022-07-22 | 2022-10-25 | 江西国化实业有限公司 | Safe purification equipment for trifluoromethanesulfonic acid production |
| CN115228105B (en) * | 2022-07-22 | 2023-10-24 | 江西国化实业有限公司 | Safety purifying equipment for production of trifluoromethanesulfonic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015022707A3 (en) | 2015-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3381923B1 (en) | Novel method for preparing lithium bis(fluorosulfonyl)imide | |
| WO2018096138A1 (en) | Solvent-free alkane sulfonation | |
| KR101975467B1 (en) | Method for preparing lithium sulfate | |
| JP2012505814A5 (en) | ||
| WO2015022707A2 (en) | Process for the synthesis of trifluoromethanesulfonic acid | |
| US2964535A (en) | Purification of nu-methyl pyrrolidone | |
| WO2014148945A1 (en) | A method for concentrating rare-earth metals in phosphogypsum | |
| ES2608041T3 (en) | Procedure for the production of di- and polyamines of the diphenylmethane series | |
| WO2016009448A1 (en) | Process for the preparation of dibenzenesulfonimide | |
| BR112021001628B1 (en) | PROCESSES FOR RECOVERY AND PRODUCTION OF 3-METHYL-BUT-3-EN-1-OL | |
| JP6414655B2 (en) | Diamine compound and method for producing the same | |
| JP5756999B2 (en) | Method for producing bis (perfluoroalkanesulfone) imide salt | |
| JP2017524723A5 (en) | ||
| JP4345088B2 (en) | DMSO recovery method | |
| JP2015017069A (en) | Diamine compound and method of producing the same | |
| EP3154933A1 (en) | Process for the preparation of 2-(trihalomethyl) benzamide | |
| JP6395069B2 (en) | Diamine compound and method for producing the same | |
| CN101379026B (en) | Process for production of O-methyl-N-nitroisourea | |
| JP2000211916A (en) | Treatment of organic solution containing lithium hexafluorophosphate or lithium tetrafluoroborate | |
| CN105460909B (en) | The post-processing approach of hydroxylamine hydrochloride mother liquid recovery process | |
| US9376379B2 (en) | Process for the synthesis of tetrafluoroethanesulfonic acid | |
| JP6164588B2 (en) | Diamine compound and method for producing the same | |
| US950936A (en) | Process of making the n-propyl ester of p-aminobenzoic acid. | |
| US3984466A (en) | Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid | |
| US3313851A (en) | Recovery of cyclohexylamine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NENP | Non-entry into the national phase in: |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 14836134 Country of ref document: EP Kind code of ref document: A2 |