CN102532195A - Method for synthesis of chlorpyrifos - Google Patents
Method for synthesis of chlorpyrifos Download PDFInfo
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- CN102532195A CN102532195A CN2011104440948A CN201110444094A CN102532195A CN 102532195 A CN102532195 A CN 102532195A CN 2011104440948 A CN2011104440948 A CN 2011104440948A CN 201110444094 A CN201110444094 A CN 201110444094A CN 102532195 A CN102532195 A CN 102532195A
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Abstract
The present invention relates to a method for synthesis of chlopyrifos. The method of the present invention comprises the following steps: (1) dissolving 1/2-1/3 of a catalyst in water to adopt as a solvent; (2) adding sodium 3,5,6-trichloropyridin-2-olate to the solvent, and adding the remaining catalyst; and (3) adding an ethyl chloride to carry out a reaction to prepare the chlorpyrifos, wherein the resulting solvent after the reaction is subjected to a purification treatment, and is recycled. According to the present invention, the solvent can be recycled after precipitation cooling, such that the characteristics of energy saving, environmental protection, simpleness and reliability are provided; the yield is high, the production cost is low, and the method has a good industrial application prospect.
Description
Technical field
The present invention relates to the synthetic field of chemical industry, be specifically related to the method for a kind of synthetic Chlorpyrifos 94.
Background technology
Chlorpyrifos 94, chemical name are O, and O-diethylammonium-O-(3,5,6 one trichloro-2-pyridyl) thiophosphatephosphorothioate is a kind of efficient, wide spectrum, low residue and low drug-fast organophosphorus pesticide.
Synthetic Chlorpyrifos 94 mainly is organic solvent method and one kettle way on the current industrial.Organic solvent method generally is organic solvent with toluene; Through condensation, operations such as underpressure distillation prepare Chlorpyrifos 94, but in this method with an organic solvent toxicity big, pollute big, operational hazards, loss is many; Be unfavorable for environment protection and safety in production, and damage HUMAN HEALTH and increase production cost; One kettle way is medium with water, adds complex phase transfer catalyst and tensio-active agent, promotes reaction, prepare Chlorpyrifos 94 through crystallisation by cooling, but this method content and yield is on the low side, and side reaction is many, and is not ideal enough.
Summary of the invention
In order to overcome above-mentioned defective, the purpose of this invention is to provide the method for a kind of environmental protection, synthetic Chlorpyrifos 94 that yield is high.
The method of synthetic Chlorpyrifos 94 of the present invention comprises the steps:
(1) 1/2～1/3 water-soluble with the catalyzer total amount as solvent;
(2) in solvent, add 3,5,6-trichloropyridine-2-sodium alkoxide is added residual catalyst;
(3) add diethylaluminum monochloride and react, make Chlorpyrifos 94, the recycle after purifying treatment of reacted solvent.
Wherein, add 0.2～0.6 weight part catalyzer, 20～40 weight parts 3,5 in per 100 weight parts waters, 6-trichloropyridine-2-sodium alkoxide, 15～30 weight part diethylaluminum monochlorides.
In addition, add 0.2～0.5 weight part catalyzer, 30～40 weight parts 3,5 in per 100 weight parts waters, 6-trichloropyridine-2-sodium alkoxide, 25～30 weight part diethylaluminum monochlorides.
In addition, in step (3), behind the adding diethylaluminum monochloride, be warming up to 42～48 ℃ of insulations earlier after 3 hours, continue to be warming up to 52～58 ℃ of insulations 2 hours.
Wherein, the fs is warming up to 42～48 ℃ of insulations 3 hours earlier, avoids the diethylaluminum monochloride volatilization, guarantees the reaction ratio balance; Subordinate phase continues to be warming up to 52～58 ℃ of insulations 2 hours, and the Chlorpyrifos 94 of guaranteeing to generate is for liquid, and avoiding occurring Chlorpyrifos 94 lumps in a large number, promotes unreacted completely 3,5, and 6-trichloropyridine-2-sodium alkoxide further reacts.
In addition, said reaction finishes the back standing demix, takes off layer oil reservoir and removes impurity with ydrogen peroxide 50 decolouring, underpressure distillation, gets Chlorpyrifos 94.
In addition, the pressure of said underpressure distillation is-0.05mpa～-0.09mpa, temperature is 80～90 ℃.
In addition, said purifying treatment comprises: reacted solvent insulation deposition after 24 hours, is cooled to 25～30 ℃ of filtering and impurity removing matter.
In addition, in step (3), said reaction is regulated pH value to 8～9 with soda ash; The adding mode of said diethylaluminum monochloride adds for stream.
In addition, said catalyzer is one or more in tri-n-octyl methyl ammonium chloride, benzyltriethylammoinium chloride, benzyl tributyl ammonium chloride, DTAC, tetramethyl ammonium chloride, polyoxyethylene glycol, the 4-Dimethylamino pyridine.
Preparing method of the present invention, after adding diethylaluminum monochloride, after the preservation for some time of heating up earlier, continuing heats up again keeps for some time, can avoid the diethylaluminum monochloride volatilization, guarantees the reaction ratio balance; The Chlorpyrifos 94 that can guarantee again to generate is for liquid, and avoiding occurring Chlorpyrifos 94 lumps in a large number, promotes unreacted completely 3,5, and 6-trichloropyridine-2-sodium alkoxide further reacts.In addition, solvent of the present invention repeated use capable of circulation after the deposition cooling can reduce discharge of wastewater, and energy-conserving and environment-protective are also simple and reliable, and in addition, yield of the present invention is high, production cost is low, and better industrial application prospects is arranged.
Description of drawings
Fig. 1 is a standard Chlorpyrifos 94 sample gas chromatogram.
The Chlorpyrifos 94 sample gas chromatogram that Fig. 2 makes for embodiment 1.
Embodiment
Following examples are used to explain the present invention, but are not used for limiting scope of the present invention.
In the 500ml there-necked flask of whisking appliance, TM is housed, add 30 ℃ of tap water 170g earlier, add 0.5g 4-Dimethylamino pyridine, under agitation condition, add 62.5g3 then successively; 5,6-trichloropyridine-2-sodium alkoxide, 0.5g 4-Dimethylamino pyridine, stream adds the 50g diethylaluminum monochloride, is warming up to 42 ℃; Be incubated 3 hours, during every surveyed a pH value at a distance from 15 minutes, through adding soda ash adjusting pH value, assurance pH value is 8; Be warming up to 58 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 58 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 85 ℃, underpressure distillation obtains as clear as crystal pale brown look oily liquids to be incubated 1 hour under-0.09MPa, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Content 98.2%, yield 99.1%.
According to GB19604-2004 the present invention being made Chlorpyrifos 94 verifies; Be specially and use GC-9890A type gas chromatograph under same experimental conditions, to measure the gas chromatogram that embodiment 1 makes Chlorpyrifos 94 and standard Chlorpyrifos 94 sample (Shenyang Chemical Engineering Inst's system); As shown in the figure; The Chlorpyrifos 94 that the present invention makes (as shown in Figure 2) is consistent with standard Chlorpyrifos 94 sample (as shown in Figure 1) chromatographic peak RT, and checking the present invention makes the Chlorpyrifos 94 National standard.
Wherein, each parameter is as shown in table 1 among Fig. 1, and each parameter is as shown in table 2 among Fig. 2.
Table 1, liquid chromatography spectrogram parameter shown in Figure 1
Table 2, liquid chromatography spectrogram parameter shown in Figure 2
Embodiment 2:
In the 500ml there-necked flask of whisking appliance, TM is housed, add 30 ℃ of tap water 170g earlier, add 0.23g benzyl tributyl ammonia chloride, under agitation condition, add 68g3 then successively; 5,6-trichloropyridine-2-sodium alkoxide, 0.11g benzyl tributyl ammonia chloride, stream adds the 50.2g diethylaluminum monochloride, is warming up to 45 ℃; Be incubated 3 hours, during every surveyed a pH value at a distance from 15 minutes, through adding soda ash adjusting pH value, assurance pH value is 9; Be warming up to 55 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 55 ℃ to staticly settle 24 hours after, be cooled to 25 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 90 ℃ of insulations 1 hour and under-0.05MPa, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Content is 98%, and yield is 98.9%.
Embodiment 3:
In the 500ml there-necked flask of whisking appliance, TM is housed, add 30 ℃ of tap water 170g earlier, add 0.48g trioctylphosphine methyl ammonium halide, under agitation condition, add 50.1g 3 then successively; 5,6-trichloropyridine-2-sodium alkoxide, 0.37g trioctylphosphine methyl ammonium halide, stream adds the 42g diethylaluminum monochloride, is warming up to 48 ℃; Be incubated 3 hours, during every surveyed a pH value at a distance from 15 minutes, through adding soda ash adjusting pH value, assurance pH value is 8.5; Be warming up to 55 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 55 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 80 ℃ of insulations 1 hour under-0.06MPa, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Content is 97.9%, and yield is 97.5%.
Embodiment 4:
In the 500ml there-necked flask of whisking appliance, TM is housed, add 30 ℃ of tap water 170g earlier, add the 0.17g DTAC, under agitation condition, add 34g 3 then successively; 5,6-trichloropyridine-2-sodium alkoxide, 0.17g DTAC,, stream adds the 35g diethylaluminum monochloride, is warming up to 46 ℃; Be incubated 3 hours, during every surveyed a pH value at a distance from 15 minutes, through adding soda ash adjusting pH value, assurance pH value is 9; Be warming up to 52 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 52 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 90 ℃ of insulations 1 hour and under-0.05MPa, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Content is 97.7%, and yield is 98.1%.
Embodiment 5:
In the 500ml there-necked flask of whisking appliance, TM is housed, add 30 ℃ of tap water 170g earlier, add the 0.25g polyoxyethylene glycol, under agitation condition, add 45g 3 then successively; 5,6-trichloropyridine-2-sodium alkoxide, 0.25g polyoxyethylene glycol,, stream adds the 35g diethylaluminum monochloride, is warming up to 44 ℃; Be incubated 3 hours, during every surveyed a pH value at a distance from 15 minutes, through adding soda ash adjusting pH value, assurance pH value is 9; Be warming up to 56 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 56 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 85 ℃ of insulations 1 hour and under-0.09MPa, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Chlorpyrifos 94 content 96.5%, yield 97%.
Embodiment 6:
In the 500ml there-necked flask of whisking appliance, TM was housed, solvent 170g was collected in accumulation among the preparation method of 30 ℃ of embodiment 1 of adding earlier, under agitation condition, adds 62.5g3,5 then successively; 6-trichloropyridine-2-sodium alkoxide, add the 0.2g tetramethyl ammonium chloride, stream adds the 50g diethylaluminum monochloride, is warming up to 46 ℃, is incubated 3 hours; Whenever surveyed a pH value during this time at a distance from 15 minutes, regulate the pH value, guarantee that the pH value is 8 through adding soda ash; Be warming up to 54 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 54 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 90 ℃ of insulations 1 hour and under-0.08MPa, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Chlorpyrifos 94 content 96.5%, yield 99%.
Embodiment 7:
In the 500ml there-necked flask of whisking appliance, TM was housed, solvent 170g was collected in accumulation among the preparation method of the embodiment 2 of 30 ℃ of collections of adding earlier, under agitation condition, adds 40g 3,5 then successively; 6-trichloropyridine-2-sodium alkoxide, add the 0.2g benzyltriethylammoinium chloride, stream adds the 38g diethylaluminum monochloride, is warming up to 42 ℃, is incubated 3 hours; Whenever surveyed a pH value during this time at a distance from 15 minutes, regulate the pH value, guarantee that the pH value is 8 through adding soda ash; Be warming up to 58 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 58 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 85 ℃ of insulations 1 hour under-0.09Mpa condition, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Chlorpyrifos 94 content 97.3%, yield 99.1%.
Embodiment 8:
In the 500ml there-necked flask of whisking appliance, TM is housed, collect accumulation solvent 170g earlier among the preparation method of 30 ℃ of embodiment 1 of adding, under agitation condition, add 50g3,5 then successively; 6-trichloropyridine-2-sodium alkoxide, add 0.12g 4-Dimethylamino pyridine, stream adds the 38g diethylaluminum monochloride, is warming up to 42 ℃, is incubated 3 hours; Whenever surveyed a pH value during this time at a distance from 15 minutes, regulate the pH value, guarantee that the pH value is 8 through adding soda ash; Be warming up to 58 ℃ again, be incubated 2 hours, left standstill 2 hours.
Upper aqueous layer changes in the 250mL beaker, keep 58 ℃ to staticly settle 24 hours after, be cooled to 30 ℃ and filter out residue, reclaim.
Layer oily matter is changed in the 500mL beaker, in the 500ml beaker, add ydrogen peroxide 50, stir; Leave standstill, divide oil, after 60 ℃ of hot water washings 2 times; Be warming up to 85 ℃ of insulations 1 hour under-0.09Mpa condition, underpressure distillation obtains as clear as crystal pale brown look oily liquids, obtains the faint yellow solid Chlorpyrifos 94 after the cooling; Chlorpyrifos 94 content 97.5%, yield 99.2%.
Claims (9)
1. the method for a synthetic Chlorpyrifos 94 is characterized in that, comprises the steps:
(1) 1/2～1/3 water-soluble with the catalyzer total amount as solvent;
(2) in solvent, add 3,5,6-trichloropyridine-2-sodium alkoxide is added residual catalyst;
(3) add diethylaluminum monochloride and react, make Chlorpyrifos 94, the recycle after purifying treatment of reacted solvent.
2. method according to claim 1 is characterized in that, adds 0.2～0.6 weight part catalyzer, 20～40 weight parts 3,5 in per 100 weight parts waters, 6-trichloropyridine-2-sodium alkoxide, 15～30 weight part diethylaluminum monochlorides.
3. method according to claim 2 is characterized in that, adds 0.2～0.5 weight part catalyzer, 30～40 weight parts 3,5 in per 100 weight parts waters, 6-trichloropyridine-2-sodium alkoxide, 25～30 weight part diethylaluminum monochlorides.
4. method according to claim 1 is characterized in that, in step (3), behind the adding diethylaluminum monochloride, is warming up to 42～48 ℃ of insulations earlier after 3 hours, continues to be warming up to 52～58 ℃ of insulations 2 hours.
5. method according to claim 1 is characterized in that, said reaction finishes the back standing demix, takes off layer oil reservoir and removes impurity with ydrogen peroxide 50 decolouring, underpressure distillation, gets Chlorpyrifos 94.
6. method according to claim 5 is characterized in that, the pressure of said underpressure distillation is-and 0.05mpa～-0.09mpa, temperature is 80～90 ℃.
7. method according to claim 1 is characterized in that, said purifying treatment comprises: reacted solvent insulation deposition after 24 hours, is cooled to 25～30 ℃ of filtering and impurity removing matter.
8. according to the arbitrary described method of claim 1～3, it is characterized in that in step (3), said reaction is regulated pH value to 8～9 with soda ash; The adding mode of said diethylaluminum monochloride adds for stream.
9. according to the arbitrary described method of claim 1～3; It is characterized in that said catalyzer is one or more in tri-n-octyl methyl ammonium chloride, benzyltriethylammoinium chloride, benzyl tributyl ammonium chloride, DTAC, tetramethyl ammonium chloride, polyoxyethylene glycol, the 4-Dimethylamino pyridine.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113121597A (en) * | 2021-04-22 | 2021-07-16 | 江苏九九久科技有限公司 | Method for preparing chlorpyrifos in condensed state |
| CN113549109A (en) * | 2021-07-26 | 2021-10-26 | 江苏九九久科技有限公司 | Method for preparing chlorpyrifos |
| CN114262346A (en) * | 2021-12-17 | 2022-04-01 | 重庆华歌生物化学有限公司 | Method for synthesizing chlorpyrifos by adopting microreactor |
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| CN1858055A (en) * | 2006-05-18 | 2006-11-08 | 徐国庆 | Method for synthesizing chlopyrifos in water medium |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113121597A (en) * | 2021-04-22 | 2021-07-16 | 江苏九九久科技有限公司 | Method for preparing chlorpyrifos in condensed state |
| CN113549109A (en) * | 2021-07-26 | 2021-10-26 | 江苏九九久科技有限公司 | Method for preparing chlorpyrifos |
| CN114262346A (en) * | 2021-12-17 | 2022-04-01 | 重庆华歌生物化学有限公司 | Method for synthesizing chlorpyrifos by adopting microreactor |
| CN114262346B (en) * | 2021-12-17 | 2023-11-28 | 重庆华歌生物化学有限公司 | Method for synthesizing chlorpyrifos by adopting microreactor |
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Effective date of registration: 20201224 Address after: 750306 east of 15th Road, Bayin Oboo Industrial Park, WUSITAI Town, Alxa League economic and Technological Development Zone, Inner Mongolia Autonomous Region Patentee after: Inner Mongolia Jianxing Chemical Co.,Ltd. Address before: 441300 village of ten li, Suizhou economic and Technological Development Zone, Hubei, China Patentee before: HUBEI BENXING AGRICULTURAL CHEMICALS Co.,Ltd. |