CN103420872A - Preparation method of lambda-cyhalothrin - Google Patents
Preparation method of lambda-cyhalothrin Download PDFInfo
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- CN103420872A CN103420872A CN2013103755920A CN201310375592A CN103420872A CN 103420872 A CN103420872 A CN 103420872A CN 2013103755920 A CN2013103755920 A CN 2013103755920A CN 201310375592 A CN201310375592 A CN 201310375592A CN 103420872 A CN103420872 A CN 103420872A
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- hexane solution
- cyhalothrin
- betacyfluthrin
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- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 title abstract 4
- 239000005910 lambda-Cyhalothrin Substances 0.000 title abstract 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000006345 epimerization reaction Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims abstract description 7
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 29
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 claims description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 21
- 241000723353 Chrysanthemum Species 0.000 claims description 13
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 13
- 150000001263 acyl chlorides Chemical class 0.000 claims description 13
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 13
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 claims description 12
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 claims description 12
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 229940043279 diisopropylamine Drugs 0.000 claims description 7
- 238000005070 sampling Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 7
- 239000002131 composite material Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 abstract 4
- CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 abstract 1
- JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 238000011033 desalting Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 238000001514 detection method Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 2
- QZPRDGCKZCJKHK-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.[F] Chemical compound O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.[F] QZPRDGCKZCJKHK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- 241001182720 Cacopsylla pyrisuga Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 fluoro-3-benzyloxy phenoxy Chemical group 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of lambda-cyhalothrin. The preparation method of the lambda-cyhalothrin comprises the steps that 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid serves as an initial raw material, DMF serves as a catalyst, n-hexane serves as solvent, an n-hexane solution of 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride is obtained, a reaction among the n-hexane solution of the 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride, 3-phenoxy-4-fluoro-benzaldehyde and sodium cyanide is carried out, methyl trioctyl ammonium chloride serves as a catalyst, a condensation reaction is carried out to obtain a cyhalothrin condensation compound, washing and desalting are carried out on the cyhalothrin condensation compound to obtain a cyhalothrin n-hexane solution, a composite catalyst is directly added to the cyhalothrin n-hexane solution, and an epimerization reaction is carried out to obtain the lambda-cyhalothrin. Compared with the prior art, the technological process is simple, the solvent does not need to be replaced in the process of preparation, the situation that isopropanol is used for carrying out working procedures such as rectification and dewatering is avoided, and the same solvent is adopted; due to the fact that the composite catalyst is adopted, the rate of the epimerization reaction is improved, and due to the facts that the n-hexane serves as epimerization solvent, and the isopropanol is not adopted, the working procedure of distillation recycling of the isopropanol and the working procedure of dewatering of the isopropanol are omitted, material loss is reduced, production cost is reduced, industrial production can be easily carried out, and popularization prospect and application prospect are wide.
Description
Technical field
The invention belongs to the preparation method in pesticide chemical field, particularly a kind of betacyfluthrin.
Background technology
Betacyfluthrin, chemistry cyano group by name-(the fluoro-3-benzyloxy phenoxy of 4-base)-methyl-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester; The no color or smell xln; Betacyfluthrin is a kind of synthetic pyrethroid insecticides, has and tags and stomach poison function, and insecticidal spectrum is wide, knocks down rapidly, and the lasting period is long, and plant has good resistance to it; The crop that betacyfluthrin is applicable: cotton, wheat, corn, vegetables, tomato, apple, oranges and tangerines, grape, rape, soybean etc.; Betacyfluthrin has good prevention effect to pests with chewing mouthparts as the part beetle of lepidopterous larvae or Coleoptera, also can be used for the control of sucking pest as pear sucker simultaneously; To crop safety; If liquid is sprayed directly on pest body, preventive effect is more excellent, to crop safety.Therefore,
At present, the betacyfluthrin of prior art mainly contains three kinds of preparation methods, but there are problems in the preparation method of prior art betacyfluthrin: complicated process of preparation, operational path length, severe reaction conditions, production cost are high, yield is low etc.The preparation method one: take toluene(mono)chloride as starting raw material, through ten steps reactions, make betacyfluthrin, the method complicated process of preparation, severe reaction conditions, production cost are high, yield is 20%; The preparation method two: take Tolylamine as starting raw material, through eight steps reactions, make betacyfluthrin, the method complicated process of preparation, severe reaction conditions, production cost are high, yield is 20%; The preparation method three: take fluorobenzaldehyde as starting raw material, through five step reactions, make betacyfluthrin, the method preparation technology is shorter, cost of investment is lower, and yield is 40%.Above three kinds of preparation methods due to complicated process of preparation, severe reaction conditions, production cost is high, yield is low, all is difficult for suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide the preparation method of the betacyfluthrin that a kind of technique is simple, production cost is low, yield is high.
The technical solution that realizes the object of the invention is: a kind of preparation method of betacyfluthrin comprises the following steps:
(1) dichloro chrysanthemum acyl chlorides is synthetic:
To stirring and add the DMF catalyzer in the container that dichlor chrysanthemic acid is housed, and normal hexane, stirring heating at the uniform velocity drips sulfur oxychloride, and it is qualified that the insulation reaction sampling detects, and the excess chlorination sulfoxide is reclaimed in underpressure distillation, makes dichloro chrysanthemum acyl chlorides hexane solution;
(2) cyfloxylate is synthetic:
Add 3-phenoxy group-4-fluorobenzaldehyde, 30wt% sodium cyanide solution and tri-n-octyl methyl ammonium chloride in reaction vessel, at the uniform velocity drip dichloro chrysanthemum acyl chlorides hexane solution under 15 ℃-18 ℃, time for adding is 4-5 hour, drip to finish under 15 ℃-18 ℃ and be incubated 2 hours, it is qualified that sampling detects, termination reaction, wash the qualified cyfloxylate hexane solution that obtains;
(3) betacyfluthrin is synthetic:
25 ℃, to stirring and add the epimerization catalyzer in the container that the cyfloxylate hexane solution is housed, then be incubated 12-13 hour, add 0.5% crystal seed (the former powder of betacyfluthrin) and be incubated 72-96 hour under 10-20 ℃, after reaction finishes, suction filtration is dried to obtain the former powder of betacyfluthrin.
DMF consumption described in step (1) is 0.5%-1.5% of dichlor chrysanthemic acid quality; Described normal hexane consumption is dichlor chrysanthemic acid quality 1-1.5 times; The 1-1.5 that described sulfur oxychloride consumption is the dichlor chrysanthemic acid molar weight doubly.
The 1-1.5 that sodium cyanide consumption described in step (2) is 3-phenoxy group-4-fluorobenzaldehyde molar weight doubly; Described tri-n-octyl methyl ammonium chloride consumption is 0.1% of 3-phenoxy group-4-fluorobenzaldehyde quality; The mol ratio of described dichloro chrysanthemum acyl chlorides and 3-phenoxy group-4-fluorobenzaldehyde is 1:1.01.
The mixture that epimerization catalyzer described in step (3) is triethylamine and Diisopropylamine, wherein by quality ratio, triethylamine: Diisopropylamine=4:6; The 5-10% that described epimerization catalyst levels is cyfloxylate hexane solution quality; Described crystal seed is 0.5% of cyfloxylate hexane solution quality.
Synthetic route is as follows:
The preparation method of betacyfluthrin of the present invention compared with prior art, technical process is simple, do not need to change solvent in preparation process, do not need to carry out with Virahol the operations such as rectifying and dewatering, adopted same solvent, it is catalyzer that the preparation of cyfloxylate adopts tri-n-octyl methyl ammonium chloride, is prepared into that the cyfloxylate crude content is high, yield is high.The betacyfluthrin preparation adopts composite catalyst (triethylamine: Diisopropylamine), improved the epimerization speed of reaction, adopting normal hexane is the epimerization solvent, do not adopt Virahol, reduce Virahol Distillation recovery, dehydration procedure, reduce material loss, reduce production costs, be easy to suitability for industrialized production, popularizing application prospect is wide.
Embodiment
Embodiment 1:
(1) dichloro chrysanthemum acyl chlorides is synthetic:
In the 1000ml four-hole boiling flask of thermometer, airway, exhaust pipe is housed, drop into normal hexane 400ml, add dichlor chrysanthemic acid 210g, under stirring, add 1.2gDMF to make catalyzer, heating drips the 136g sulfur oxychloride, drips insulation reaction 6 hours, and GC follows the tracks of the detection dichlor chrysanthemic acid and transforms fully, the excess chlorination sulfoxide is reclaimed in underpressure distillation, obtains 404g dichloro chrysanthemum acyl chlorides hexane solution.
(2) cyfloxylate is synthetic:
Drop into 28.5g sodium cyanide and 130g water in the 1000ml reaction flask, be stirred to fully and dissolve, add 0.108g tri-n-octyl methyl ammonium chloride and 108g fluorine 3-Phenoxy-benzaldehyde, agitation and dropping 202g dichloro chrysanthemum acyl chlorides hexane solution, dropping temperature is at 25 ℃, within 3 hours, evenly drip, dropwise insulation reaction sampling in 1 hour, detect and control fluorine 3-Phenoxy-benzaldehyde≤0.2%, cyfluthrin content >=99.5%(GC desolventizes normalizing content), termination reaction, be washed to neutrality, normal pressure removes 10% moisture normal hexane, obtain the cyfloxylate hexane solution, cyfloxylate crude yield >=99% wherein, external standard detection level >=95%.
(3) betacyfluthrin is synthetic:
Add 390g cyfloxylate hexane solution in thermometer is housed, stirs four-hole boiling flask, stir that to add 19.5g epimerization catalyzer in 25 ℃ (be triethylamine: the composite catalyst of Diisopropylamine=4:6), then 25 ℃ are incubated 8 hours, 20 ℃ add the 19.5g crystal seed and are incubated 12 hours, 15 ℃ are incubated 48 hours, and 10 ℃ are incubated 24 hours.It is termination reaction that sampling detection α body burden reaches 95%, and suction filtration is dried to obtain the 200g betacyfluthrin, external standard detection level >=94%, the former powder yield of betacyfluthrin >=92%.
Embodiment 2
Change the reaction conditions of the first step, other step is as embodiment 1, that is:
(1) dichloro chrysanthemum acyl chlorides is synthetic:
In the 1000ml four-hole boiling flask of thermometer, airway, exhaust pipe is housed, drop into normal hexane 400ml, add dichlor chrysanthemic acid 210g, under stirring, add 3.0gDMF to make catalyzer, heating drips the 160g sulfur oxychloride, drips insulation reaction 2 hours, and GC follows the tracks of the detection dichlor chrysanthemic acid and transforms fully, the excess chlorination sulfoxide is reclaimed in underpressure distillation, obtains 405g dichloro chrysanthemum acyl chlorides hexane solution.
Embodiment 3
Change the reaction conditions of the 3rd step, other step is as embodiment 1, that is:
(3) betacyfluthrin is synthetic:
Add 390g cyfloxylate hexane solution in thermometer is housed, stirs four-hole boiling flask, stir that to add 39g epimerization catalyzer in 25 ℃ (be triethylamine: the composite catalyst of Diisopropylamine=4:6), then 25 ℃ are incubated 8 hours, 20 ℃ add the 19.5g crystal seed and are incubated 12 hours, 15 ℃ are incubated 48 hours, and 10 ℃ are incubated 24 hours.It is termination reaction that sampling detection α body burden reaches 95%, and suction filtration is dried to obtain the 203g betacyfluthrin.
Claims (4)
1. the preparation method of a betacyfluthrin is characterized in that comprising the following steps:
(1) dichloro chrysanthemum acyl chlorides is synthetic:
To stirring and add the DMF catalyzer in the container that dichlor chrysanthemic acid is housed, and normal hexane, stirring heating at the uniform velocity drips sulfur oxychloride, and it is qualified that the insulation reaction sampling detects, and the excess chlorination sulfoxide is reclaimed in underpressure distillation, makes dichloro chrysanthemum acyl chlorides hexane solution;
(2) cyfloxylate is synthetic:
Add 3-phenoxy group-4-fluorobenzaldehyde, sodium cyanide solution and tri-n-octyl methyl ammonium chloride in reaction vessel, at the uniform velocity drip dichloro chrysanthemum acyl chlorides hexane solution under 15 ℃-18 ℃, time for adding is 4-5 hour, drip to finish under 15 ℃-18 ℃ and be incubated 2 hours, it is qualified that sampling detects, termination reaction, wash the qualified cyfloxylate hexane solution that obtains;
(3) betacyfluthrin is synthetic:
25 ℃, to stirring and add the epimerization catalyzer in the container that the cyfloxylate hexane solution is housed, then be incubated 12-13 hour, add 0.5% crystal seed and under 10-20 ℃ insulation 72-96 hour, after reaction finishes, suction filtration is dried to obtain the former powder of betacyfluthrin.
2. the preparation method of betacyfluthrin according to claim 1, is characterized in that the DMF consumption described in step (1) is 0.5%-1.5% of dichlor chrysanthemic acid quality; Described normal hexane consumption is dichlor chrysanthemic acid quality 1-1.5 times; The 1-1.5 that described sulfur oxychloride consumption is the dichlor chrysanthemic acid molar weight doubly.
3. the preparation method of betacyfluthrin according to claim 1, is characterized in that the sodium cyanide solution mass concentration described in step (2) is 30%; The 1-1.5 that described sodium cyanide consumption is 3-phenoxy group-4-fluorobenzaldehyde molar weight doubly; Described tri-n-octyl methyl ammonium chloride consumption is 0.1% of 3-phenoxy group-4-fluorobenzaldehyde quality; The mol ratio of described dichloro chrysanthemum acyl chlorides and 3-phenoxy group-4-fluorobenzaldehyde is 1:1.01.
4. the preparation method of betacyfluthrin according to claim 1, is characterized in that the mixture that the epimerization catalyzer described in step (3) is triethylamine and Diisopropylamine, wherein by quality ratio, and triethylamine: Diisopropylamine=4:6; The 5-10% that described epimerization catalyst levels is cyfloxylate hexane solution quality; Described crystal seed is 0.5% of cyfloxylate hexane solution quality.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109111373A (en) * | 2018-10-09 | 2019-01-01 | 南通天泽化工有限公司 | A kind of preparation method of Cyhalothrin |
| CN115894291A (en) * | 2022-12-12 | 2023-04-04 | 江苏优嘉植物保护有限公司 | A kind of preparation method of α-Kongfuthrin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4423222A (en) * | 1982-05-21 | 1983-12-27 | The Dow Chemical Company | Pyridinyl fungicides and herbicides |
| CN1068933A (en) * | 1991-07-27 | 1993-02-17 | 张曾如 | Manufacturing method for high active chloro-cyanogen pyrethrin pesticide |
| CN1020598C (en) * | 1987-06-15 | 1993-05-12 | Fmc有限公司 | Conversion of pyrethroid isomers to more active species |
| CN1508124A (en) * | 2002-12-18 | 2004-06-30 | 颜汉新 | Method for synthesizing lambda-cyhalothrin from p-fluorobenzoic aldehyde |
-
2013
- 2013-08-26 CN CN2013103755920A patent/CN103420872A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4423222A (en) * | 1982-05-21 | 1983-12-27 | The Dow Chemical Company | Pyridinyl fungicides and herbicides |
| CN1020598C (en) * | 1987-06-15 | 1993-05-12 | Fmc有限公司 | Conversion of pyrethroid isomers to more active species |
| CN1068933A (en) * | 1991-07-27 | 1993-02-17 | 张曾如 | Manufacturing method for high active chloro-cyanogen pyrethrin pesticide |
| CN1508124A (en) * | 2002-12-18 | 2004-06-30 | 颜汉新 | Method for synthesizing lambda-cyhalothrin from p-fluorobenzoic aldehyde |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109111373A (en) * | 2018-10-09 | 2019-01-01 | 南通天泽化工有限公司 | A kind of preparation method of Cyhalothrin |
| CN115894291A (en) * | 2022-12-12 | 2023-04-04 | 江苏优嘉植物保护有限公司 | A kind of preparation method of α-Kongfuthrin |
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Application publication date: 20131204 |