CN101948414A - Method for preparing 2-ethylsulfonyl-5-methoxyl-2, 4-glutaconicnitrile - Google Patents
Method for preparing 2-ethylsulfonyl-5-methoxyl-2, 4-glutaconicnitrile Download PDFInfo
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- CN101948414A CN101948414A CN2010102748381A CN201010274838A CN101948414A CN 101948414 A CN101948414 A CN 101948414A CN 2010102748381 A CN2010102748381 A CN 2010102748381A CN 201010274838 A CN201010274838 A CN 201010274838A CN 101948414 A CN101948414 A CN 101948414A
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Abstract
The invention discloses a method for preparing 2-ethylsulfonyl-5-methoxyl-2,4-glutaconicnitrile, which comprises the steps of: putting1,1,3,3-tetramethoxypropane and acetic anhydride into a stirred reactor in a molar ratio of 1:2 to 1:4 to react for 1 to 1.5h at a temperature of 95 to 120 DEG C; reducing the temperature to 95 to 100 DEG C and dropping ethylsulfonyl acetonitrile, wherein the molar ratio of the ethylsulfonyl acetonitrile to the 1,1,3,3-tetramethoxypropane 1.1-1.3 to 1; controlling the dropping time between 20 and 40 minutes; after the dropping is finished, increasing the temperature to 120 to 125 DEG C to react for 7 to 9h; and cooling, and adding glacial acetic acid for dissolving to obtain the target product. The invention has the advantages that the product with purity over 92.0% is prepared under the technological conditions, industrial production is easy to realize, and the total yield is not less than 83.0% in terms of 1,1,3,3-tetramethoxypropane.
Description
Technical field
The present invention relates to a kind of preparation method of organic compound, be specifically related to 2-second sulphonyl-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile.
Background technology
2-second sulphonyl-5-methoxyl group-2,4-pentadiene nitrile is a kind of important organic synthesis intermediate, is mainly used in synthetic sulfonylurea herbicide rimsulfuron 25.Rimsulfuron 25 is numerous sulfonylurea herbicides of developing in recent years one of outstanding kinds in new.Rimsulfuron 25 is absorbed in plant materials, causes weeds death by conduction generation effect, and has metabolism and selectivity.It can not cause groundwater pollution in illumination and degraded in soil, in soil, do not exist residual, to succession crop safety.Rimsulfuron 25 is registered as the corn postemergence weed control in China, and is very welcome on market, but the enterprise of domestic industry production rimsulfuron 25 seldom, and technology, quality are also lower, and the main dependence on import of product costs an arm and a leg.
2-second sulphonyl-5-methoxyl group-2,4-pentadiene nitrile new synthetic method helps to advance the rimsulfuron 25 industrialization development, and to China's development higher effective and lower toxic pesticide new variety, the update of accelerating weedicide will play a positive role.
Summary of the invention
Technical problem to be solved by this invention provides a kind of 2-second sulphonyl-5-methoxyl group-2, and the preparation method of 4-pentadiene nitrile is to realize suitability for industrialized production.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
A kind of 2-second sulphonyl-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile, with 1,1,3,3-tetramethoxy propane and diacetyl oxide are sent into stirred reactor with 1: 2～4 mol ratio, react 1～1.5 hour down at 95～120 ℃; Be cooled to 95～100 ℃ again, drip second sulphonyl acetonitrile simultaneously, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.1～1.3: 1, the dropping time was controlled at 20～40 minutes; After dropwising, be warming up to 120～125 ℃ of reactions 7～9 hours; Cooling adds the Glacial acetic acid dissolving and obtains target product.
Wherein, 1,1,3, preferred 1: 3 of the reaction mol ratio of 3-tetramethoxy propane and diacetyl oxide.
Wherein, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is preferably 1.2: 1.
Wherein, the dropping time of second sulphonyl acetonitrile preferably was controlled at 30 minutes.
Wherein, preferably, after dropwising, be warming up to 120～125 ℃ of reactions 8 hours
Wherein, the consumption of Glacial acetic acid be cooled reaction system volume 24～35%.
The reaction equation of above-mentioned technology is as follows:
Beneficial effect: the present invention compared with prior art, its remarkable advantage is:
1, the present invention is with reactant 1,1,3, and 3-tetramethoxy propane and diacetyl oxide mol ratio are 1: 2～4, and side reaction reduces, and reaction develops to favourable direction; Reaction solution residence time in reactor is reduced.
2, second sulphonyl acetonitrile of the present invention drips 20～40 minutes time, 95～100 ℃ of temperature, and temperature is low, and reaction develops to beneficial direction.
3, material reaction time under abundant agitation condition is short among the present invention.
4, can to obtain purity be product more than 92.0% in the present invention, with 1,1,3, and 3-tetramethoxy propane meter, total recovery 〉=83.0%., satisfy need of industrial production fully.
Embodiment
According to following embodiment, the present invention may be better understood.Yet, those skilled in the art will readily understand that the described concrete material proportion of embodiment, processing condition and result thereof only are used to illustrate the present invention, and should also can not limit the present invention described in detail in claims.
Embodiment 1:
In reactor, add 1,1,3,3-tetramethoxy propane, diacetyl oxide, mol ratio 1: 3 is started stirring (mixing speed 90～100r/m), slowly be heated to 105～110 ℃, reacted 1 hour, reduce temperature to 95～100 ℃, dripped second sulphonyl acetonitrile in 30 minutes, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.3: 1, is warming up to 120～125 ℃, isothermal reaction 8 hours constantly steams low-boiling point liquid.Cooling adds the Glacial acetic acid dissolving and obtains target product, the consumption of Glacial acetic acid be cooled reaction system volume 30%.Product purity is 94.7%, with 1,1,3, and 3-tetramethoxy propane meter, total recovery of the present invention is 87.0%.
Embodiment 2:
In reactor, add 1,1,3,3-tetramethoxy propane, diacetyl oxide, mol ratio 1: 2 is started stirring (mixing speed 90～100r/m), slowly be heated to 110～120 ℃, reacted 1 hour, reduce temperature to 95～100 ℃, dripped second sulphonyl acetonitrile in 30 minutes, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.1: 1, is warming up to 120～125 ℃, isothermal reaction 7 hours constantly steams low-boiling point liquid.Cooling adds the Glacial acetic acid dissolving and obtains target product, the consumption of Glacial acetic acid be cooled reaction system volume 25%.Product purity is 92.9%, with 1,1,3, and 3-tetramethoxy propane meter, total recovery 84.3% of the present invention.
Embodiment 3:
In reactor, add 1,1,3,3-tetramethoxy propane, diacetyl oxide, mol ratio 1: 4 is started stirring (mixing speed 90～100r/m), slowly be heated to 95～105 ℃, reacted 1.5 hours, reduce temperature to 95～100 ℃, dripped second sulphonyl acetonitrile in 40 minutes, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.3: 1, is warming up to 120～125 ℃, isothermal reaction 9 hours constantly steams low-boiling point liquid.Cooling adds the Glacial acetic acid dissolving and obtains target product, the consumption of Glacial acetic acid be cooled reaction system volume 35%.Product purity is 92.2%, with 1,1,3, and 3-tetramethoxy propane meter, total recovery 82.3% of the present invention.
Claims (6)
1. 2-second sulphonyl-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile is characterized in that with 1,1,3 3-tetramethoxy propane and diacetyl oxide are sent into stirred reactor with 1: 2～4 mol ratio, 95～120 ℃ of reactions 1～1.5 hour down; Be cooled to 95～100 ℃ again, drip second sulphonyl acetonitrile simultaneously, second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.1～1.3: 1, the dropping time was controlled at 20～40 minutes; After dropwising, be warming up to 120～125 ℃ of reactions 7～9 hours; Cooling adds the Glacial acetic acid dissolving and obtains target product.
2. 2-second sulphonyl according to claim 1-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile is characterized in that with 1,1,3 3-tetramethoxy propane and diacetyl oxide are sent into stirred reactor with 1: 3 mol ratio.
3. 2-second sulphonyl according to claim 1-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile is characterized in that second sulphonyl acetonitrile and 1,1,3, the mol ratio of 3-tetramethoxy propane is 1.2: 1.
4. 2-second sulphonyl according to claim 1-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile is characterized in that the dropping time of second sulphonyl acetonitrile was controlled at 30 minutes.
5. 2-second sulphonyl according to claim 1-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile after it is characterized in that dropwising, is warming up to 120～125 ℃ of reactions 8 hours.
6. 2-second sulphonyl according to claim 1-5-methoxyl group-2, the preparation method of 4-pentadiene nitrile, the consumption that it is characterized in that Glacial acetic acid be cooled reaction system volume 24～35%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102748381A CN101948414A (en) | 2010-09-07 | 2010-09-07 | Method for preparing 2-ethylsulfonyl-5-methoxyl-2, 4-glutaconicnitrile |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102748381A CN101948414A (en) | 2010-09-07 | 2010-09-07 | Method for preparing 2-ethylsulfonyl-5-methoxyl-2, 4-glutaconicnitrile |
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| CN101948414A true CN101948414A (en) | 2011-01-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2010102748381A Pending CN101948414A (en) | 2010-09-07 | 2010-09-07 | Method for preparing 2-ethylsulfonyl-5-methoxyl-2, 4-glutaconicnitrile |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0323881A1 (en) * | 1988-01-04 | 1989-07-12 | E.I. Du Pont De Nemours And Company | Cyano-Dienes, Halopyridines, intermediates and a process for their preparation |
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2010
- 2010-09-07 CN CN2010102748381A patent/CN101948414A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0323881A1 (en) * | 1988-01-04 | 1989-07-12 | E.I. Du Pont De Nemours And Company | Cyano-Dienes, Halopyridines, intermediates and a process for their preparation |
Non-Patent Citations (3)
| Title |
|---|
| 卢鑫鑫，等: "新型除草剂玉嘧磺隆的合成研究", 《现代农药》 * |
| 张大永，等: "玉 嘧 磺 隆 的 合 成", 《农药》 * |
| 陈明，等: "2-溴-3-乙磺酰基吡啶的合成", 《农药》 * |
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Application publication date: 20110119 |