CN102229545A - Production method for the intermediate methanesulfonic acid-2-propoxy ethyl ester of pretilachlor - Google Patents
Production method for the intermediate methanesulfonic acid-2-propoxy ethyl ester of pretilachlor Download PDFInfo
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- CN102229545A CN102229545A CN2011101176820A CN201110117682A CN102229545A CN 102229545 A CN102229545 A CN 102229545A CN 2011101176820 A CN2011101176820 A CN 2011101176820A CN 201110117682 A CN201110117682 A CN 201110117682A CN 102229545 A CN102229545 A CN 102229545A
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- ethyl ester
- production method
- propoxy
- chloride
- metal halide
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Abstract
The invention discloses a production method for the intermediate methanesulfonic acid-2- propoxy ethyl ester of pretilachlor. According to the method, glycol monopropyl ether reacts with methanesulfonyl chloride, and a metal halide is used as a catalyst for the reaction. The production method provided in the invention has the advantages of easy operation, simple equipment, a small amount of the three wastes (waste gas, waste water and industrial residue) and low cost, and the content and yield of the produced products are high.
Description
Technical field
The present invention relates to a kind of third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method.
Background technology
The present domestic synthetic technology of third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester is generally as follows: a certain amount of ethylene glycol ether and methyl semi-annular jade pendant acyl chlorides (excessive 8%) are mixed, be cooled to below 10 ℃, slowly drip triethylamine (other acid binding agent also appears in the newspapers).After being added dropwise to complete, natural thermal insulation 2h.Take a sample qualified after, add water washing, standing demix promptly gets target product.It is yield that methylsulphonic acid-2-propoxy-ethyl ester that this method is produced has higher, but pilot process has used acid binding agent, and production cost is greatly increased.Though acid binding agent can reclaim, the removal process complexity need add alkaline purification.Exist the rate of recovery not high in the acid binding agent removal process, produce waste water and need a series of problems such as processing again.
Summary of the invention
The object of the present invention is to provide product content height, the third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method that yield is high.
Technical solution of the present invention is:
A kind of third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method is characterized in that: with ethylene glycol ether and Methanesulfonyl chloride reaction, reaction is a catalyzer with the metal halide.
The described third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method, metal halide catalyst is joined in the mixed solution of ethylene glycol ether and Methanesulfonyl chloride by 1% proportioning, stir, slowly be warming up to 130 ℃, sampling analysis is emitted in insulation until no hydrogen chloride gas, ethylene glycol ether≤1%, reaction is finished.
Described metal halide catalyst is cupric chloride, cupric bromide, iron(ic) chloride or iron bromide or other metal halide catalysts.
The mol ratio of reactant: ethylene glycol ether: Methanesulfonyl chloride: catalyzer=1:1.08: 0.01.
The present invention has processing ease, equipment is simple, the three wastes are few, and cost is low, product content is high, yield is high.
The invention will be further described below in conjunction with embodiment.
Embodiment
Embodiment 1:
104g ethylene glycol positive propyl ether is placed the 500ml there-necked flask, add Methanesulfonyl chloride 123.5g Methanesulfonyl chloride and stir.Add metal halide class catalyzer cupric chloride (or cupric bromide, iron(ic) chloride or iron bromide or other metal halide catalysts) 3g.Slow heat temperature raising, tail gas absorbs with alkali lye, is heated to 130 ℃ of insulation 2h, does not have bubble substantially and emits.Sampling analysis: methylsulphonic acid-2-propoxy-ethyl ester content is 94.72%.Get product 173g, yield is 95.12%.
Embodiment 2:
52g ethylene glycol positive propyl ether is placed the 500ml there-necked flask, add Methanesulfonyl chloride 61.8g Methanesulfonyl chloride and stir.Add catalyzer iron(ic) chloride (or cupric bromide, cupric chloride or iron bromide or other metal halide catalysts) 1.5g.Slow heat temperature raising, tail gas absorbs with alkali lye, is heated to 130 ℃ of insulation 2.5h, does not have bubble substantially and emits.Sampling analysis: methylsulphonic acid-2-propoxy-ethyl ester content is 94.44%.Get product 87g, yield is 95.67%.
Embodiment 3:
208g ethylene glycol positive propyl ether is placed the 1000ml there-necked flask, add Methanesulfonyl chloride 247g Methanesulfonyl chloride and stir.Add catalyzer cupric chloride (or cupric bromide, iron(ic) chloride or iron bromide or other metal halide catalysts) 6g.Reactions steps is with embodiment 1,2, and sampling analysis: methylsulphonic acid-2-propoxy-ethyl ester content is 95.10%.Get product 346g, yield is 95.07%.
Claims (3)
1. careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method is characterized in that: with ethylene glycol ether and Methanesulfonyl chloride reaction, reaction is a catalyzer with the metal halide.
2. the according to claim 1 third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method, it is characterized in that: metal halide catalyst is joined in the mixed solution of ethylene glycol ether and Methanesulfonyl chloride by 1% proportioning, stir, slowly be warming up to 130 ℃, sampling analysis is emitted in insulation until no hydrogen chloride gas, ethylene glycol ether≤1%, reaction is finished.
3. the according to claim 1 and 2 third careless amine intermediate methylsulphonic acid-2-propoxy-ethyl ester production method, it is characterized in that: described metal halide catalyst is cupric chloride, cupric bromide, iron(ic) chloride or iron bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101176820A CN102229545A (en) | 2011-05-09 | 2011-05-09 | Production method for the intermediate methanesulfonic acid-2-propoxy ethyl ester of pretilachlor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2011101176820A CN102229545A (en) | 2011-05-09 | 2011-05-09 | Production method for the intermediate methanesulfonic acid-2-propoxy ethyl ester of pretilachlor |
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| CN102229545A true CN102229545A (en) | 2011-11-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2011101176820A Pending CN102229545A (en) | 2011-05-09 | 2011-05-09 | Production method for the intermediate methanesulfonic acid-2-propoxy ethyl ester of pretilachlor |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05155843A (en) * | 1991-12-05 | 1993-06-22 | Yoshitomi Pharmaceut Ind Ltd | Production of sulfonic acid hydroxyphenyl ester |
| CN1473149A (en) * | 2000-10-03 | 2004-02-04 | ���ǻ�ѧ��˾ | Method for sulphonylating hydroxylated organic compound |
| CN101407482A (en) * | 2008-03-27 | 2009-04-15 | 河北迈尔斯通电子材料有限公司 | intermediate for synthesizing butene liquid crystal and synthetic method thereof |
| CN101475508A (en) * | 2009-01-22 | 2009-07-08 | 南通德益化工有限公司 | Production process of 2,6-diethyl-N-(2-propoxyethyl) acetanil |
| EP2161254A1 (en) * | 2002-03-05 | 2010-03-10 | Sumitomo Chemical Company, Limited | Intermediate for preparing a biaryl compound |
-
2011
- 2011-05-09 CN CN2011101176820A patent/CN102229545A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05155843A (en) * | 1991-12-05 | 1993-06-22 | Yoshitomi Pharmaceut Ind Ltd | Production of sulfonic acid hydroxyphenyl ester |
| CN1473149A (en) * | 2000-10-03 | 2004-02-04 | ���ǻ�ѧ��˾ | Method for sulphonylating hydroxylated organic compound |
| EP2161254A1 (en) * | 2002-03-05 | 2010-03-10 | Sumitomo Chemical Company, Limited | Intermediate for preparing a biaryl compound |
| CN101407482A (en) * | 2008-03-27 | 2009-04-15 | 河北迈尔斯通电子材料有限公司 | intermediate for synthesizing butene liquid crystal and synthetic method thereof |
| CN101475508A (en) * | 2009-01-22 | 2009-07-08 | 南通德益化工有限公司 | Production process of 2,6-diethyl-N-(2-propoxyethyl) acetanil |
Non-Patent Citations (1)
| Title |
|---|
| 袁冠华，严成武: "S-(-)-对甲苯磺酰乳酸", 《化工时刊》 * |
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Application publication date: 20111102 |