CN87101526A - A kind of method of synthetic Butachlor technical 92 - Google Patents
A kind of method of synthetic Butachlor technical 92 Download PDFInfo
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- CN87101526A CN87101526A CN 87101526 CN87101526A CN87101526A CN 87101526 A CN87101526 A CN 87101526A CN 87101526 CN87101526 CN 87101526 CN 87101526 A CN87101526 A CN 87101526A CN 87101526 A CN87101526 A CN 87101526A
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- chloro
- diethyl
- butachlor technical
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- acetanilide
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Abstract
A kind of method of synthetic Butachlor technical 92, this method are to adopt 2, and 6-Diethyl Aniline and Mono Chloro Acetic Acid are at PCl
3, POCl
3Or PCl
5There are down not solubilizing agent and catalyzer, direct reaction generates 2 ', 6 '-diethyl-2-chloro acetanilide, then in the presence of an amount of Butachlor technical 92, in alkaline aqueous solution, react with the chloro methyl butyl ether and to make Butachlor technical 92, yield is 90%.It is a kind of herbicide before seedling stage, is used for rice terrace and prevents and kill off annual gramineous weed and some broadleaved herb, the weeds that also can be used for preventing and kill off ground such as wheat, barley, beet, cotton.
Description
The invention provides a kind of synthetic method of improved agricultural herbicide Butachlor technical 92.
The common name of Butachlor technical 92 is butachlor, and other title has Machete, CP53619, chemical name is 2 ', 6 '-diethyl-N-fourth oxygen methyl-2-chloro-acetanilide N.
Structural formula:
It is a kind of herbicide before seedling stage, is used for rice terrace and prevents and kill off annual gramineous weed and some broadleaved herb.Also can be used for preventing and kill off the weeds on ground such as wheat, barley, beet, cotton, peanut.
The existing abroad report of the preparation method of Butachlor technical 92: U, S, P, 3,442,945; 3,547,620; 3,630,716; The synthetic method of this weedicide of reporting in 3,637,847 patents all is to adopt 2, and 6-Diethyl Aniline and trimerization or Paraformaldehyde 96 react in inert solvents such as benzene,toluene,xylene, chlorobenzene sloughs mol water generation methene aniline.The same chlorine of Mono Chloro Acetic Acid, Sulfur or protochloride, phosgene reaction generate chloroacetyl chloride, and the resultant of methene aniline and chloroacetyl chloride addition reaction makes Butachlor technical 92 with the butanols reaction again.
Reaction equation is as follows:
The weak point of aforesaid method is the reaction formula I
a, I
dBe reversible reaction, for improving product yield, formaldehyde and butanols all need excessive (mole ratio of reporting in the existing patent is 1: 3～5).Excessive formaldehyde and butanols have increased postprocessing working procedures, need with methene distillation dehydration tower, formaldehyde upgrading tower, Butanol Recycling tower, chloroacetyl chloride refining and distilling tower and reactor product precipitation tower.This method needs many with equipment, and investment is big.In addition, U, S, P, 4,319, reported in 917 by 2 ', 6 '-diethyl-2-chloro acetanilide and halogenated methyl alkyl oxide are in the presence of the phase-transfer catalyst quaternary ammonium salt, and reaction generates the method for Butachlor technical 92 in inert solvent benzene, chlorobenzene.This method need reclaim catalyzer and solvent.Complicated operation, the corresponding raising of cost.
The novel method that the purpose of this invention is to provide a kind of synthetic Butachlor technical 92 without phase-transfer catalyst and inert solvent.
The object of the present invention is achieved like this: this method is with 2, and 6-Diethyl Aniline and Mono Chloro Acetic Acid are at PCl
3, POCl
3Or PCl
5Existing down, not solubilizing agent and catalyzer, direct reaction generate 2 ', 6 '-diethyl-2-chloro acetanilide.The said products (as NaOH, KOH), reacts with the chloro methyl butyl ether and can make purity and yield all at the Butachlor technical 92 more than 90% in alkaline aqueous solution in the presence of an amount of Butachlor technical 92.Reaction formula is as follows:
Characteristics of the present invention are to be raw material with Mono Chloro Acetic Acid, have shortened reaction process, without phase-transfer catalyst and inert solvents such as quaternary ammonium salts, have saved the recovery process of catalyzer, and heat energy consumption is few, and product cost reduces.
Adopt the reaction conditions and the proportioning raw materials of the synthetic Butachlor technical 92 of this method as follows:
1, etherificate produces that the mole ratio of used butanols and formaldehyde is that 1: 1 temperature of reaction is 10～50 ℃ in the chloromethyl butyl ether, and reaction pressure is normal pressure or 720～740mmHg column pressure.
2, chloride produce 2 ', 6 '-raw materials used 2 in diethyl-2-chloro acetanilide, 6-Diethyl Aniline and Mono Chloro Acetic Acid, PCl
3Mole ratio be 1: 1.15～1.5: 0.35～0.6.Drip PCl
3The time temperature be 50～60 ℃, the temperature of keeping when reaction is 85～105 ℃, the reaction times is 1～3 hour.
3, condensation reaction produce in the Butachlor technical 92 2 ', 6 '-mole ratio of diethyl-2-chloro acetanilide and chloromethyl butyl ether is 1: 1～1.5, temperature of reaction is 10～50 ℃, and the time that drips the chloromethyl butyl ether is 0.5～1 hour, and the reaction times is 0.5～1 hour.
Embodiment 1:2 ', 6 '-diethyl-2-chloro acetanilide synthetic
In the four-hole bottle that agitator, thermometer, dropping funnel and tail gas absorption bottle are housed, add 0.1 molar 2,6-Diethyl Aniline and 0.15 molar Mono Chloro Acetic Acid mix, drip 0.05 molar trichlorine oxygen concrete down in normal temperature, temperature reaction, the hydrogen chloride gas of emitting feeds and fills in the tail gas absorption bottle of formaldehyde-butanols (1: 1), till no HCl gas is emitted.Reaction finishes, and adds entry, filters out solid, and drying makes 2, and 6-diethyl-2-chloro acetanilide need not purified, and it is synthetic to be directly used in down the step.Yield is (with 2,6-Diethyl Aniline meter) more than 95%.
Embodiment 2: Butachlor technical 92 synthetic
In the four-hole bottle that agitator, thermometer, dropping funnel and reflux cooler are housed, add 0.1 molar 2 ', 6 '-diethyl-2-chloro acetanilide and 30～40 milliliters of Butachlor technical 92 stirring and dissolving, add 45% aqueous sodium hydroxide solution again, drip 0.115 molar chloromethyl butyl ether down in low temperature.Dropwise, continued stirring reaction 1 hour.Add the salt that the suitable quantity of water solubilizing reaction generates in reactant, standing demix divides oil-yielding stratum, gets flaxen oily liquids, is Butachlor technical 92, yield 95%.
Claims (3)
1, the present invention is the synthetic method of agricultural herbicide Butachlor technical 92, it is characterized in that by 2, and 6-Diethyl Aniline and Mono Chloro Acetic Acid are at PCl
3, POCl
3Or PCl
5Exist down, not solubilizing agent and catalyzer, direct reaction generation 2 ', 6 '-diethyl-2-chloro acetanilide, this product is made the novel method of the synthetic Butachlor technical 92 of reaction under the solvent again at a small amount of Butachlor technical 92 itself with the chloro methyl butyl ether, wherein, produce 2 ', 6 '-the used raw material 2 of diethyl-2-chloro acetanilide, the 6-Diethyl Aniline, Mono Chloro Acetic Acid, the mole ratio of the muriate of phosphorus or oxychlorination thing is 1: 1.15～1.5: 0.35～0.6, by 2 ', 6 '-diethyl-2-chloro acetanilide and chloro methyl butyl ether produce in the Butachlor technical 92, the mole ratio of raw material consumption is 1: 1～1.5, drips PCl
3The time temperature be 50～60 ℃, keeping temperature of reaction is 85～105 ℃, the reaction times is 1～3 hour, the temperature of reaction of producing Butachlor technical 92 is 10～50 ℃, the reaction times is 0.5～1 hour.
2, method according to claim 1, it is characterized in that producing 2 ', 6 '-the used raw material 2 of diethyl-2-chloro acetanilide, the optimal molar ratio of 6-Diethyl Aniline, Mono Chloro Acetic Acid, phosphorus trichloride consumption is 1: 1.5: 0.5.
3, method according to claim 1, it is characterized in that producing Butachlor technical 92 raw materials used 2 ', 6 '-optimal molar ratio of diethyl-2-chloro acetanilide and chloro methyl butyl ether consumption is 1: 1.15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 87101526 CN87101526A (en) | 1987-03-31 | 1987-03-31 | A kind of method of synthetic Butachlor technical 92 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 87101526 CN87101526A (en) | 1987-03-31 | 1987-03-31 | A kind of method of synthetic Butachlor technical 92 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN87101526A true CN87101526A (en) | 1988-11-23 |
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ID=4813497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 87101526 Pending CN87101526A (en) | 1987-03-31 | 1987-03-31 | A kind of method of synthetic Butachlor technical 92 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN87101526A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102442922A (en) * | 2011-08-26 | 2012-05-09 | 吉林大学 | Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction |
| CN104555963A (en) * | 2014-12-28 | 2015-04-29 | 江苏绿利来股份有限公司 | Method for recycling waste phosphoric acid during production of butachlor |
| CN105230633A (en) * | 2015-10-29 | 2016-01-13 | 江苏东宝农药化工有限公司 | Herbicide with broad-spectrum weeding effect |
-
1987
- 1987-03-31 CN CN 87101526 patent/CN87101526A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102442922A (en) * | 2011-08-26 | 2012-05-09 | 吉林大学 | Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction |
| CN104555963A (en) * | 2014-12-28 | 2015-04-29 | 江苏绿利来股份有限公司 | Method for recycling waste phosphoric acid during production of butachlor |
| CN105230633A (en) * | 2015-10-29 | 2016-01-13 | 江苏东宝农药化工有限公司 | Herbicide with broad-spectrum weeding effect |
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