CN101492403A - Method for catalysis preparation of trifluoromethyl sulphinyl chlorine - Google Patents
Method for catalysis preparation of trifluoromethyl sulphinyl chlorine Download PDFInfo
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- CN101492403A CN101492403A CNA2008102043167A CN200810204316A CN101492403A CN 101492403 A CN101492403 A CN 101492403A CN A2008102043167 A CNA2008102043167 A CN A2008102043167A CN 200810204316 A CN200810204316 A CN 200810204316A CN 101492403 A CN101492403 A CN 101492403A
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- trifluoromethyl sulphinyl
- trifluoromethyl
- sulphinyl chlorine
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Abstract
The invention relates to a method for preparing trifluoromethyl sulphinyl chloride by catalysis. In the method, trifluoromethyl sodium sulphinate and thionyl chloride are used as raw materials to react for 1 to 8 hours under the temperature of 20 DEG C to 100 DEG C under the action of catalyst and then are distilled under normal pressure; and distilled fraction is rectified for collecting the fraction under 41 DEG C to 43 DEG C to obtain the trifluoromethyl sulphinyl chloride. Compared with the prior art, by using a catalyst method to synthesize the trifluoromethyl sulphinyl chloride, the invention has reasonable technology and simple and convenient operation, avoids the side reaction and produces few impurities; the invention has low cost, high content (more than 95 percent) and the yield of 75 percent; the obtained products have stable performance; the quality is not influenced when the product is preserved under normal temperature; and the product is used for synthesizing fipronil with the yield of 80 percent and the content more than 95 percent.
Description
Technical field
The present invention relates to the intermediate of sterilant, relate in particular to a kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine.
Background technology
Trifluoromethyl sulphinyl chlorine is the intermediate of synthetic pesticide fluorine worm nitrile, and the quality of trifluoromethyl sulphinyl chlorine directly has influence on the synthetic yield and the quality of fluorine worm nitrile, and therefore, trifluoromethyl sulphinyl chlorine content must be more than 95%.
At present, preparation trifluoromethyl sulphinyl chlorine technology has following two kinds:
1. trifluoromethanesulpacidc acidc sodium acyl chlorides legal system trifluoromethyl sulphinyl chlorine, reaction equation is as follows:
F
3CSO
2Na+CLSOCL→F
3CSOCL+SO
2+NaCL
Trifluoromethyl sulphinyl chlorine was made in 35 degree reactions by trifluoromethanesulpacidc acidc sodium and sulfur oxychloride in 3 hours, and crude product obtains product by rectifying.This reaction side reaction is more, causes impurity to generate, and impurity has F
3SCL etc., content has only 85%, and yield 55% is because impurity is many, some impurity rectifying rear impurity can not be removed, and the finished product that obtains is very unstable, can not place, and placing has precipitation to generate for a long time, directly have influence on the synthetic of fluorine worm nitrile, cause the decline of yield, the reduction of content.
2. sulfinyl thing oxidation method for preparing trifluoromethyl sulphinyl chlorine, reaction equation is as follows:
Trifluoromethyl benzyl-sulfinic acid thing is dissolved in the methylene dichloride, feeds chlorine at normal temperature and obtain trifluoromethyl sulphinyl chlorine yield 80%, because the preparation of trifluoromethyl benzyl-sulfinic acid thing is very difficult, cost is very high.
Summary of the invention
Purpose of the present invention is exactly the method that the catalysis preparation of trifluoromethyl sulphinyl chlorine of a kind of product purity height, stable performance is provided for the defective that overcomes above-mentioned prior art existence.
Purpose of the present invention can be achieved through the following technical solutions:
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine, it is characterized in that, this method is a raw material with trifluoromethanesulpacidc acidc sodium, sulfur oxychloride, under the effect of catalyzer, in 20～100 degree reactions 1～8 hour, air distillation, the cut that distills out are carried out rectifying and are collected 41～43 degree cuts, obtain trifluoromethyl sulphinyl chlorine.
The mol ratio of described trifluoromethyl sulphinyl sodium, sulfur oxychloride and catalyzer is 1: 5～10: 0.01～0.1.
Preferred 1: 7: 0.05 of the mol ratio of described trifluoromethyl sulphinyl sodium, sulfur oxychloride and catalyzer.
Described catalyzer comprises aluminum chloride, zinc chloride or iron trichloride.
Reaction scheme of the present invention is as follows:
Compared with prior art, the synthetic trifluoromethyl sulphinyl chlorine technology of catalyst method of the present invention is reasonable, simple, convenient, has avoided side reaction, impurity generates few, cost is low, content height (more than 95%), yield 75%, the product performance that obtain are stable, normal temperature is placed quality not to be influenced, and is used for synthetic fluorine worm nitrile yield and can reaches 80%, and content is greater than 95%.
Embodiment
The invention will be further described below in conjunction with specific embodiment.
Embodiment 1
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine may further comprise the steps:
Trifluoromethanesulpacidc acidc sodium 156 grams, sulfur oxychloride 833 grams, aluminum chloride 6.7 gram inputs have in 1000 milliliters the there-necked flask of stirring and prolong, start and stir, and are warming up to 50 degree, be incubated after 4 hours, carry out air distillation, the cut that distills out carries out rectifying and collects 41～43 degree cuts, obtains 120.4 gram trifluoromethyl sulphinyl chlorines, content is more than 95%, yield 75%.The rectifying mother liquor can be applied mechanically at the bottom of the tower.
Embodiment 2
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine may further comprise the steps:
Trifluoromethanesulpacidc acidc sodium 156 grams, sulfur oxychloride 833 grams, zinc chloride 6.8 gram inputs have in 1000 milliliters the there-necked flask of stirring and prolong, start and stir, be warming up to 50 degree insulations and carry out air distillation after 4 hours, the cut that distills out carries out rectifying and collects 41～43 degree cuts, obtains 115.6 gram trifluoromethyl sulphinyl chlorines, content is more than 95%, yield 72%.The rectifying mother liquor can be applied mechanically at the bottom of the tower.
Embodiment 3
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine may further comprise the steps:
Trifluoromethanesulpacidc acidc sodium 156 grams, sulfur oxychloride 833 grams, iron trichloride 8.1 gram inputs have in 1000 milliliters the there-necked flask of stirring and prolong, start and stir, be warming up to 50 degree insulations and carry out air distillation after 4 hours, the cut that distills out carries out rectifying and collects 41～43 degree cuts, obtains 112.4 gram trifluoromethyl sulphinyl chlorines, content is more than 95%, yield 70%.The rectifying mother liquor can be applied mechanically at the bottom of the tower.
Embodiment 4
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine may further comprise the steps:
Trifluoromethanesulpacidc acidc sodium 156 grams, sulfur oxychloride 595 grams, aluminum chloride 1.34 gram inputs have in 1000 milliliters the there-necked flask of stirring and prolong, start and stir, be warming up to 20 degree insulations and carry out air distillation after 8 hours, the cut that distills out carries out rectifying and collects 41～43 degree cuts, obtains 118 gram trifluoromethyl sulphinyl chlorines, content is more than 95%, yield 74%.The rectifying mother liquor can be applied mechanically at the bottom of the tower.
Embodiment 5
A kind of method of catalysis preparation of trifluoromethyl sulphinyl chlorine may further comprise the steps:
Trifluoromethanesulpacidc acidc sodium 156 grams, sulfur oxychloride 833 grams, aluminum chloride 13.4 gram inputs have in 1000 milliliters the there-necked flask of stirring and prolong, start and stir, be warming up to 100 degree insulations and carry out air distillation after 1 hour, the cut that distills out carries out rectifying and collects 41～43 degree cuts, obtains 120 gram trifluoromethyl sulphinyl chlorines, content is more than 95%, yield 75%.The rectifying mother liquor can be applied mechanically at the bottom of the tower.
Claims (4)
1. the method for a catalysis preparation of trifluoromethyl sulphinyl chlorine, it is characterized in that, this method is a raw material with trifluoromethanesulpacidc acidc sodium, sulfur oxychloride, under the effect of catalyzer, in 20～100 degree reactions 1～8 hour, air distillation, the cut that distills out are carried out rectifying and are collected 41～43 degree cuts, obtain trifluoromethyl sulphinyl chlorine.
2. the method for catalysis preparation of trifluoromethyl sulphinyl chlorine according to claim 1 is characterized in that, the mol ratio of described trifluoromethyl sulphinyl sodium, sulfur oxychloride and catalyzer is 1: 5～10: 0.01～0.1.
3. the method for catalysis preparation of trifluoromethyl sulphinyl chlorine according to claim 2 is characterized in that, preferred 1: 7: 0.05 of the mol ratio of described trifluoromethyl sulphinyl sodium, sulfur oxychloride and catalyzer.
4. the method for catalysis preparation of trifluoromethyl sulphinyl chlorine according to claim 1 is characterized in that, described catalyzer comprises aluminum chloride, zinc chloride or iron trichloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102043167A CN101492403A (en) | 2008-12-10 | 2008-12-10 | Method for catalysis preparation of trifluoromethyl sulphinyl chlorine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102043167A CN101492403A (en) | 2008-12-10 | 2008-12-10 | Method for catalysis preparation of trifluoromethyl sulphinyl chlorine |
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|---|---|
| CN101492403A true CN101492403A (en) | 2009-07-29 |
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| CNA2008102043167A Pending CN101492403A (en) | 2008-12-10 | 2008-12-10 | Method for catalysis preparation of trifluoromethyl sulphinyl chlorine |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102108057A (en) * | 2010-12-10 | 2011-06-29 | 上海博康精细化工有限公司 | Method for preparing adamantane sulfonyl chloride by using adamantane sulfinyl chloride |
| CN102791683A (en) * | 2010-01-04 | 2012-11-21 | 克基·霍尔穆斯吉·阿加尔达 | A method for preparation of perfluoroalkyl sulfenyl chloride |
| CN106699615A (en) * | 2016-12-28 | 2017-05-24 | 江苏托球农化股份有限公司 | Preparation process of trifluoromethyl sulfinyl chloride |
| CN112266344A (en) * | 2020-11-17 | 2021-01-26 | 江西国化实业有限公司 | Preparation process of trifluoromethyl sulfinyl chloride |
| CN113105375A (en) * | 2021-04-10 | 2021-07-13 | 山东智永化工产业技术研究院有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
| CN113795478A (en) * | 2019-03-16 | 2021-12-14 | 格哈达化工有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
-
2008
- 2008-12-10 CN CNA2008102043167A patent/CN101492403A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102791683A (en) * | 2010-01-04 | 2012-11-21 | 克基·霍尔穆斯吉·阿加尔达 | A method for preparation of perfluoroalkyl sulfenyl chloride |
| US9617207B2 (en) | 2010-01-04 | 2017-04-11 | Keki Hormusji Gharda | Method for preparation of perfluoroalkyl sulfenyl chloride |
| CN102108057A (en) * | 2010-12-10 | 2011-06-29 | 上海博康精细化工有限公司 | Method for preparing adamantane sulfonyl chloride by using adamantane sulfinyl chloride |
| CN102108057B (en) * | 2010-12-10 | 2013-07-10 | 上海博康精细化工有限公司 | Method for preparing adamantane sulfonyl chloride by using adamantane sulfinyl chloride |
| CN106699615A (en) * | 2016-12-28 | 2017-05-24 | 江苏托球农化股份有限公司 | Preparation process of trifluoromethyl sulfinyl chloride |
| CN113795478A (en) * | 2019-03-16 | 2021-12-14 | 格哈达化工有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
| CN113795478B (en) * | 2019-03-16 | 2023-12-26 | 格哈达化工有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
| CN112266344A (en) * | 2020-11-17 | 2021-01-26 | 江西国化实业有限公司 | Preparation process of trifluoromethyl sulfinyl chloride |
| CN113105375A (en) * | 2021-04-10 | 2021-07-13 | 山东智永化工产业技术研究院有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
| CN113105375B (en) * | 2021-04-10 | 2023-07-07 | 山东智永化工产业技术研究院有限公司 | Preparation method of trifluoromethyl sulfinyl chloride |
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Open date: 20090729 |