CN102250023A - High yield synthetic method for quizalofop-p-ethyl - Google Patents
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Abstract
The invention relates to a synthetic method for quizalofop-p-ethyl, a high efficiency herbicide. The method comprises the four steps of water straining, substitution, rinsing and crystallization. According to the method, 6-chlorine-2-(4-hydroxyphenoxy)quinoxaline reacts with R(-)p-toluenesulfonyl ethyl lactate, alkali metal and salts thereof are employed as acid binding agents, a single organic solvent is employed as a reaction system, and solid-liquid separation is used for separating a product; the yield of the product exceeds 90%, the content of the product is about 97.5%, and the content of the active substance R is more than 94%. Compared to the conventional technology, the preparation method provided in the invention has the characteristics of little side reaction, a short flow, a stationary process, high yield of the product, high content of the active substance and low energy consumption.
Description
Technical field
The invention belongs to the Pesticidal products synthesis technical field, relate to herbicide for paddy field quizalofopPethyl synthetic method.
Background technology
QuizalofopPethyl is mainly used in broad leaf crop and prevents and kill off annual, perennial gramineous weeds, and is as barnyard grass grass, Herba Setariae Viridis, wild avena sativa, bromegrass, Semen Euphorbiae etc., invalid to broadleaf weeds.Product is that selectivity inner sucting conduction type cauline leaf is handled weedicide.Medicament absorbs by the weeds cauline leaf, two-way up and down conduction.Annual gramineous weed medicament in 24 hours can spread all over complete stool, and inhibition cell, lipid acid synthesize, and withered.Has the extensive high-efficiency characteristics of use range
The main method of domestic synthetic quizalofopPethyl is to react in sherwood oil at present, and reaction removes solvent after finishing, and changes another solvent (being generally ethanol) and carries out recrystallization, then the centrifugal quizalofopPethyl that obtains of decrease temperature crystalline.This processing method complicated operation solvent loss is big, and production cost is higher, the production cycle is long, and yield is lower.
Summary of the invention
Complicated operation, the solvent loss that the present invention is directed to present industrialized producing technology existence is big, production cost is higher, the lower problem of long yield of production cycle, a kind of employing single organic solvent is provided, need not remove the synthetic method of the direct decrease temperature crystalline of solvent, thereby shorten the production technique cycle, simplify Production Flow Chart, improve synthesis yield, reduce production costs.
The object of the present invention is achieved like this, with 6-chloro-2-(4-hydroxyphenoxy) quinoxaline and R (-) p-toluenesulfonyl ethyl lactate is raw material, in organic solvent, acid binding agent an alkali metal salt or alkali exists, back flow reaction under the anhydrous state, obtain target product, generate water-soluble toluenesulfonate simultaneously; Toluenesulfonate is removed in washing, and crystallization obtains the target product quizalofopPethyl.Reaction principle is as follows: M+ represents alkaline carbonate or alkali
The high yield synthetic method of the quizalofopPethyl that the present invention relates to comprises band water, replacement, washing and four steps of crystallization:
(1) band water: 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, an alkali metal salt or alkali and the mixed system that contains the organic solvent of alicyclic structure are stirred temperature rising reflux, the anhydrous outflow to the water trap of band water;
(2) replace: after band water is finished, the band water state keeps refluxing, drip R (-) p-toluenesulfonyl ethyl lactate, drip and finish back continuation reaction more than 4 hours, sampling is surveyed and is followed the tracks of, with 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content≤0.1%, R (-) p-toluenesulfonyl content of ethyl lactate≤1.5% is a reaction end;
(3) washing: hot wash to the reaction system water with 65 ℃～85 ℃ after reaction finishes is neutral, divides to fall water;
(4) crystallization: to the oil phase decrease temperature crystalline, filter, dry filter residue obtains target product.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, the mol ratio of described 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, R (-) p-toluenesulfonyl ethyl lactate, an alkali metal salt is 1:1.05-1.45:1.5-3.4.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, the mass ratio of described 6-chloro-2-(4-hydroxyphenoxy) quinoxaline and solvent is 1:6-10.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, described organic solvent are selected from a kind of in hexanaphthene, suberane, the pimelinketone.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, described an alkali metal salt is selected from potassium hydroxide, sodium hydroxide, a kind of or its mixed system in salt of wormwood, yellow soda ash, the Quilonum Retard.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to; sampling survey tracking R (-) p-toluenesulfonyl content of ethyl lactate in the replacement process＞1.5% o'clock; with excess R (-) p-toluenesulfonyl ethyl lactate is that benchmark is added 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, back flow reaction by the 1:1 proportioning.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, described sampling are surveyed to follow the tracks of and are adopted the gas-chromatography area normalization method to calculate.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, described washing process also comprises the organic phase activated carbon decolorizing.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, described crystallization condition are 5 ℃～10 ℃, 2-4h.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to adopts single organic solvent as reaction system, avoids because of changing the yield reduction that solvent causes; Adopt solid-liquid separation method with product, avoided solvent distillatory energy loss, organic solvent can directly be recycled simultaneously.
The high yield synthetic method of the quizalofopPethyl that the present invention relates to, side reaction is few, and flow process is short, and reaction process is steady, product yield height, content height.And simplify the complexity of producing, reduce production costs, and can reduce cost of equipment.
Embodiment
Concrete processing step of the present invention is described by the following examples, and only limitation is not interpreted as that the above-mentioned subject area of the present invention only limits to following example.All technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
Embodiment one
Input 275kg content is 97.4% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline in having the 5000L reactor of division box, should note preventing generation of static electricity band anti-electrostatic folder, drop into yellow soda ash 250kg again, open solvent line valve and squeeze into the 2750kg hexanaphthene, the sealing manhole.In test tank be 96% R (-) p-toluenesulfonyl ethyl lactate 298kg with vacuum drawn content, standby.
Jiggering flexibly back starts and stirs, and temperature rising reflux band water no longer includes the globule to the water trap and sinks, and continues band water 0.5 hour, and reaction system is anhydrous state.
After band water finished, the maintenance system refluxed and is with water state, at the uniform velocity drips R (-) p-toluenesulfonyl ethyl lactate, and 4.5 hours consuming time, be added dropwise to complete the back and continue reaction 6h, sampling is followed the tracks of.
Obtaining 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content with the gas chromatographic analysis area normalization method is 0.08%, and R (-) p-toluenesulfonyl content of ethyl lactate is 1.25%, material is gone in the washing still carry out aftertreatment.
Open cycle water for cooling to 60 is ℃-65 ℃ in the washing still, carry out the washing first time, under agitation feed the hot water 800kg about 65 ℃, stirred 20 minutes, drive bottom valve and change in second 5000L reactor controlled temperature at 60 ℃-65 ℃, stir static separatory after 30 minutes, lower floor's water branch is fallen decontaminated water treatment plant, batt layer keeps; Drop into the processing of decolouring of 20kg300 order gac, 60 ℃ of-65 ℃ of insulated and stirred 30 minutes, filter out gac with the processing of 350 order filter cloth sheet frames, filtrate goes in the 3rd the 5000L reactor, carries out the washing second time, and hot water stirring maintenance in the 30 minutes washing temperature that feeds about 800kg65 ℃ is 60 ℃-65 ℃, static separatory, lower floor's water branch falls decontaminated water treatment plant, and upper oil phase is washed for the third time, and the condition of washing is for the third time washed identical with the second time.
Open cycle water is lowered the temperature to oil phase, be cooled to 20 ℃ after, change logical cool brine and reduce to 5 ℃, 5 ℃～7 ℃ following insulated and stirred, stirring velocity is 85 rev/mins, crystallization 2h.
The frame (350 order filter cloth) that re-packs filter the quizalofopPethyl wet feed, sweep the smart quinoline of sheet frame with wind, it is wet 17.9% that the smart quinoline of sheet frame contains, and tears the sheet frame discharging open, 50 ℃ of expansion dryings obtain 417kg target product quizalofopPethyl, yield is 91%.
The quizalofopPethyl chemical content that this example makes is 97.6%, and optical purity is 96.5%, and the R body is 94.2%.
Embodiment two
Input 400kg content is 97% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline in the 5000L reactor, should note preventing generation of static electricity band anti-electrostatic folder, drop into potassium hydroxide 230kg again, opening solvent line valve, to measure the 2400kg pimelinketone be reaction solvent, the sealing manhole.In test tank be 96.3% R (-) p-toluenesulfonyl ethyl lactate 423kg with vacuum drawn content, standby.
Jiggering back flexibly starts stirring, and temperature rising reflux band water no longer includes the globule to water trap and sinks, and continues band water 0.5 hour, and reaction system is anhydrous state.After band water finished, the maintenance system refluxed and is with water state, at the uniform velocity drips R (-) p-toluenesulfonyl ethyl lactate, 2 hours consuming time, took a sample behind the reaction 10h and followed the tracks of.Use gas chromatographic analysis, 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content 0.06%, R (-) p-toluenesulfonyl content of ethyl lactate 0.95% reaches terminal point, material is gone in the washing still carry out aftertreatment.
Open cycle water is washed for the first time and is cooled to about 75 ℃-80 ℃, under agitation feeds 75 ℃ of hot water 1200kg, stirs 20 minutes, drive bottom valve and change in second 5000L reactor controlled temperature at 75 ℃-80 ℃, stir static separatory after 30 minutes, lower floor's water branch is fallen, batt layer keeps.Drop into the processing of decolouring of 30kg250 order gac, 75 ℃ of-80 ℃ of insulated and stirred 30 minutes.Finish laggard andante frame (300 order filter cloth) processing and filter out gac, filtrate goes in the 3rd the 5000L reactor, carries out the washing second time, and feeding 1200kg75 ℃ of hot water stirring maintenance in 30 minutes washing temperature is 75 ℃-80 ℃, static separatory, lower floor's water branch falls decontaminated water treatment plant.After washing finishes, open cycle water is to the oil phase decrease temperature crystalline, after being cooled to 20 ℃, change logical cool brine and reduce to 10 ℃, 70 rev/mins 8 ℃～10 ℃ insulation crystallization 4h, the frame (350 order filter cloth) that re-packs filters to such an extent that contain wet 22.4% quizalofopPethyl wet feed, and 55 ℃ of expansion dryings obtain 601.6kg target product quizalofopPethyl, yield 93.1%.
The quizalofopPethyl chemical content that this example makes is 97.5%, and optical purity is 97%, and the R body is 94.6%.
Embodiment three
Input 275kg content is 96.5% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline in the 5000L reactor, should note preventing generation of static electricity band anti-electrostatic folder, drops into potassium hydroxide 163kg again, opens solvent line valve and squeezes into the 2500kg suberane, the sealing manhole.In test tank be 95.8% R (-) p-toluenesulfonyl ethyl lactate 310kg with vacuum drawn content, standby.
Jiggering back flexibly starts stirring, and temperature rising reflux band water no longer includes the globule to water trap and sinks, and continues band water 0.5 hour, and reaction system is anhydrous state.After band water finished, the maintenance system refluxed and is with water state at the uniform velocity to drip R (-) p-toluenesulfonyl ethyl lactate, 4 hours dropping time, continued reaction 4h sampling survey tracking after being added dropwise to complete.With gas chromatographic analysis 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content 0.03%, R (-) p-toluenesulfonyl content of ethyl lactate 0.65% reaches terminal point, material is gone in the washing still carry out aftertreatment.
Open cycle water is washed for the first time and is cooled to 70 ℃-75 ℃, under agitation feeds 70 ℃ of hot water 1200kg, stirs 20 minutes, drive bottom valve and change in second 5000L reactor controlled temperature at 70 ℃, stir static separatory after 10 minutes, lower floor's water branch is fallen decontaminated water treatment plant, batt layer keeps.Washing for the second time, feeding 1200kg70 ℃ of hot water stirring maintenance in 10 minutes washing temperature is 65 ℃-70 ℃, static separatory, lower floor's water branch falls decontaminated water treatment plant.Feed 70 ℃ of hot water 1200kg again, stir and washed for the third time in 20 minutes, static separatory divides and falls down a layer water.Open cycle water is to the oil phase decrease temperature crystalline, change logical cool brine after being cooled to 20 ℃ and be cooled to 10 ℃, at 75 rev/mins, 7 ℃～9 ℃ insulation crystallization 2h, the frame (300 order filter cloth) that re-packs filters and obtains containing wet 18.5% quizalofopPethyl wet feed, 60 ℃ of expansion dryings obtain 395kg target product quizalofopPethyl, yield 94.5%.
The quizalofopPethyl chemical content that this example makes is 97.3%, and optical purity is 96.8%, and the R body is 94.2%
Embodiment four
Input 250kg content is 96% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline in the 3000L reactor, should note preventing generation of static electricity band anti-electrostatic folder, drop into sodium hydroxide 50kg and 6kg Quilonum Retard again, open solvent line valve and squeeze into the 1500kg hexalin, the sealing manhole.In test tank be 97% R (-) p-toluenesulfonyl ethyl lactate 321kg with vacuum drawn content, standby.
Jiggering back flexibly starts stirring, and temperature rising reflux band water no longer includes the globule to water trap and sinks, and continues band water 1 hour, and reaction system is anhydrous state.After band water finished, the maintenance system refluxed and is with water state at the uniform velocity to drip R (-) p-toluenesulfonyl ethyl lactate, and 3 hours dropping time, tracking is surveyed in sampling behind the continuation reaction 4h.With gas chromatographic analysis 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content 0.04%, R (-) p-toluenesulfonyl content of ethyl lactate 1.8%.
Follow the tracks of defective; add content and be 96% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline; 30kg; after the band water that continues to reflux reacts 2h; get the tracking sample, chromatography of gases is analyzed 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content 0.07%, R (-) p-toluenesulfonyl content of ethyl lactate 1.1%; reach terminal point, material is gone in the washing still carry out aftertreatment.
Open cycle water for cooling to 60 ℃-65 ℃ under agitation feeds 65 ℃ of hot water 1000kg washings, stirs 20 minutes, drives bottom valve and changes that controlled temperature stirs static separatory after 20 minutes at 60-65 ℃ in the 5000L reactor over to, the branch phase of anhydrating.Similarity condition washing three times.
Washing finishes back open cycle water to the oil phase decrease temperature crystalline, change logical cool brine after being cooled to 20 ℃ and be cooled to 8 ℃, at 60 rev/mins, 6 ℃～8 ℃ insulation crystallization 3h, the frame (300 order) that re-packs filters, after vacuumizing 30 minutes, the line that blows in obtains containing wet 22.1% quizalofopPethyl wet feed after purging sheet frame 1h, and 58 ℃ of expansion dryings obtain 372kg target product quizalofopPethyl, and yield is 90.6%.
The quizalofopPethyl content that this example makes is 97.2%, and optical purity is 96.8%, and the R body is 94.1%.
Embodiment five
Input 275kg content is 97.2% 6-chloro-2-(4-hydroxyphenoxy) quinoxaline in the 5000L reactor, should note preventing generation of static electricity band anti-electrostatic folder, drops into salt of wormwood 230kg again, opens solvent line valve and squeezes into recovery suberane 2500kg, sealing manhole.In test tank be 97% R (-) p-toluenesulfonyl ethyl lactate 330kg with vacuum drawn content, standby.
Jiggering back flexibly starts stirring, and temperature rising reflux band water no longer includes the globule to water trap and sinks, and continues band water 1 hour, and reaction system is anhydrous state.After being with water to finish, the maintenance system refluxes and is with water state at the uniform velocity to drip R (-) p-toluenesulfonyl ethyl lactate, drips 4h, and the sampling survey is followed the tracks of behind the continuation reaction 4h.With gas chromatographic analysis 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content 0.05%, R (-) p-toluenesulfonyl content of ethyl lactate 1.35% reaches terminal point, material is gone in the washing still carry out aftertreatment.
Open cycle water is washed for the first time and is cooled to about 70 ℃, under agitation feed 70 ℃ of hot water 1200kg, stirred 20 minutes, drive bottom valve and change in second 5000L reactor controlled temperature at 70 ℃-75 ℃, stir static separatory after 10 minutes, lower floor's water branch is fallen decontaminated water treatment plant, and batt layer keeps.Washing for the second time, feeding 1200kg70 ℃ of hot water stirring maintenance in 10 minutes washing temperature is 70 ℃-75 ℃, static separatory, lower floor's water branch falls decontaminated water treatment plant.Feed 70 ℃ of hot water 1200kg again, stir washing in 20 minutes for the third time, washing finishes the back and divides the phase of anhydrating.
Open cycle water is to the oil phase decrease temperature crystalline, change logical cool brine after being cooled to 20 ℃ and be cooled to 8 ℃, at 65 rev/mins, 7 ℃～8 ℃ insulation crystallization 2h, the frame (350 order) that re-packs filters, obtain containing wet 17.8% quizalofopPethyl wet feed, 60 ℃ of expansion dryings obtain 409kg target product quizalofopPethyl, and yield is 91.5%.
The quizalofopPethyl chemical content that this example makes is 97.4%, and optical purity is 96.8%, and the R body is 94.3%.
Claims (9)
1. the high yield synthetic method of quizalofopPethyl comprises band water, replacement, washing and four steps of crystallization:
(1) band water: 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, an alkali metal salt or alkali and the mixed system that contains the organic solvent of alicyclic structure are stirred temperature rising reflux, the anhydrous outflow to the water trap of band water;
(2) replace: after band water is finished, the band water state keeps refluxing, drip R (-) p-toluenesulfonyl ethyl lactate, drip and finish back continuation reaction more than 4 hours, sampling is surveyed and is followed the tracks of, with 6-chloro-2-(4-hydroxyphenoxy) quinoxaline content≤0.1%, R (-) p-toluenesulfonyl content of ethyl lactate≤1.5% is a reaction end;
(3) washing: hot wash to the reaction system water with 65 ℃～85 ℃ after reaction finishes is neutral, divides to fall water;
(4) crystallization: to the oil phase decrease temperature crystalline, filter, dry filter residue obtains target product.
2. the high yield synthetic method of the described quizalofopPethyl of claim 1, the mol ratio of described 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, R (-) p-toluenesulfonyl ethyl lactate, an alkali metal salt is 1:1.05-1.45:1.5-3.4.
3. the high yield synthetic method of the described quizalofopPethyl of claim 1, the mass ratio of described 6-chloro-2-(4-hydroxyphenoxy) quinoxaline and solvent is 1:6-10.
4. the high yield synthetic method of the described quizalofopPethyl of claim 1, described organic solvent are selected from a kind of in hexanaphthene, suberane, the pimelinketone.
5. the high yield synthetic method of the described quizalofopPethyl of claim 1, described an alkali metal salt is selected from potassium hydroxide, sodium hydroxide, a kind of or its mixed system in salt of wormwood, yellow soda ash, the Quilonum Retard.
6. the high yield synthetic method of the described quizalofopPethyl of claim 1; sampling survey tracking R (-) p-toluenesulfonyl content of ethyl lactate in the replacement process＞1.5% o'clock; with excess R (-) p-toluenesulfonyl ethyl lactate is that benchmark is added 6-chloro-2-(4-hydroxyphenoxy) quinoxaline, back flow reaction by the 1:1 proportioning.
7. the high yield synthetic method of the described quizalofopPethyl of claim 6, described sampling are surveyed to follow the tracks of and are adopted the gas-chromatography area normalization method to calculate.
8. the high yield synthetic method of the described quizalofopPethyl of claim 1, described washing process also comprises the organic phase activated carbon decolorizing.
9. the high yield synthetic method of the described quizalofopPethyl of claim 1, described crystallization condition is 5 ℃～10 ℃, 2-4h.
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| CN102584724A (en) * | 2012-02-06 | 2012-07-18 | 京博农化科技股份有限公司 | Preparation method for quizalofop-p-ethyl |
| CN102675232A (en) * | 2012-05-17 | 2012-09-19 | 山东京博控股股份有限公司 | Synthetic method of 4-(6-chlorine-quinoxaline-2-yloxy)-phenol |
| CN107739343A (en) * | 2017-09-07 | 2018-02-27 | 京博农化科技股份有限公司 | A kind of environment-friendly type technique for producing Quizalotop-ethyl |
| CN107915686A (en) * | 2017-09-07 | 2018-04-17 | 京博农化科技股份有限公司 | A kind of Quizalotop-ethyl and its intermediate 4（6 chlorine, 2 quinoxaline epoxide）The synthetic method of phenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102584724A (en) * | 2012-02-06 | 2012-07-18 | 京博农化科技股份有限公司 | Preparation method for quizalofop-p-ethyl |
| CN102584724B (en) * | 2012-02-06 | 2016-06-15 | 京博农化科技股份有限公司 | A kind of preparation method of Quizalotop-ethyl |
| CN102675232A (en) * | 2012-05-17 | 2012-09-19 | 山东京博控股股份有限公司 | Synthetic method of 4-(6-chlorine-quinoxaline-2-yloxy)-phenol |
| CN102675232B (en) * | 2012-05-17 | 2014-12-17 | 山东京博控股股份有限公司 | Synthetic method of 4-(6-chlorine-quinoxaline-2-yloxy)-phenol |
| CN107739343A (en) * | 2017-09-07 | 2018-02-27 | 京博农化科技股份有限公司 | A kind of environment-friendly type technique for producing Quizalotop-ethyl |
| CN107915686A (en) * | 2017-09-07 | 2018-04-17 | 京博农化科技股份有限公司 | A kind of Quizalotop-ethyl and its intermediate 4（6 chlorine, 2 quinoxaline epoxide）The synthetic method of phenol |
| CN107739343B (en) * | 2017-09-07 | 2020-06-19 | 京博农化科技股份有限公司 | Environment-friendly process for producing quizalofop-p-ethyl |
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