CN103804231A - Synthesis method for pesticide intermediate trifluoroacetonitrile - Google Patents
Synthesis method for pesticide intermediate trifluoroacetonitrile Download PDFInfo
- Publication number
- CN103804231A CN103804231A CN201410069168.8A CN201410069168A CN103804231A CN 103804231 A CN103804231 A CN 103804231A CN 201410069168 A CN201410069168 A CN 201410069168A CN 103804231 A CN103804231 A CN 103804231A
- Authority
- CN
- China
- Prior art keywords
- trifluoroacetonitrile
- pph
- synthesis method
- pph3
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- SFFUEHODRAXXIA-UHFFFAOYSA-N 2,2,2-trifluoroacetonitrile Chemical compound FC(F)(F)C#N SFFUEHODRAXXIA-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000000575 pesticide Substances 0.000 title claims abstract description 6
- 238000001308 synthesis method Methods 0.000 title abstract 3
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000010189 synthetic method Methods 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- -1 tetracol phenixin Chemical compound 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 6
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 abstract 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- YWMBTEPHKWBZKK-UHFFFAOYSA-N n,2,2,2-tetrafluoroacetamide Chemical compound FNC(=O)C(F)(F)F YWMBTEPHKWBZKK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention provides a synthesis method for a pesticide intermediate trifluoroacetonitrile. The synthesis method comprises the following steps: adding trifluorofluoroacetamide, carbon tetrachloride and trifluoroacetic anhydride into a gas reaction kettle; raising the temperature to 150-180 DEG C; dehydrating and reacting; and cooling to obtain the trifluoroacetonitrile. A reaction formula is as follows: CF3CONH2+PPh3+CCl4->CF3C(Gl)=NH+O=PPh3+CHCl3CF3C(Cl)=NH+PPH3->CF3CN+PPh3+HCl.
Description
Technical field
The present invention relates to a kind of synthetic method of trifluoro acetonitrile.
Background technology
Trifluoro acetonitrile is widely used in containing in the heterogeneous ring compound of trifluoromethyl synthetic as active electrophilic reagent, it is a kind of important chemical intermediate, along with the development of fluoro-containing pesticide medicine, heterocyclic compound species containing trifluoromethyl is increasing, demand also increases gradually, and therefore trifluoro acetonitrile has a wide range of applications at agricultural chemicals, aspect medical.Abroad to the research and development of trifluoro acetonitrile with produce carry out early, as the halocarbon company of the large King Company of Japan, the U.S. etc.But the domestic suitability for industrialized production of also failing to realize trifluoro acetonitrile, need be from external import trifluoro acetonitrile resynthesis various agricultural chemicals, medicine intermediates containing trifluoromethyl.
Along with the development of trifluoroacetic acid derived product, take trifluoroacetamide as raw material, under dewatering agent effect, the method for preparing trifluoro acetonitrile through dehydration reaction becomes study hotspot gradually, and this method has that reaction orientation is good, product yield is high and the advantage such as easily separated purification.According to the literature, the dewatering agent that this method is now used is divided into trifluoroacetic anhydride/pyridine and San Ben Ji Scales/tetracol phenixin/mineral alkali two classes.
Reaction by trifluoroacetamide Dehydration for trifluoro acetonitrile, high at laboratory lab scale stage productive rate, but in this solid-solid reaction actual industrial production process, exist and be unfavorable for many Hazard Factor such as heat transfer, therefore find suitable solvent most important.
Summary of the invention
technical problem
In view of this, the technical problem to be solved in the present invention is, provides a kind of by selecting suitable dewatering agent to simplify technique, reduce costs and improve productive rate, is more conducive to the trifluoro acetonitrile synthetic method of suitability for industrialized production.
solution
In order to solve the problems of the technologies described above, the invention provides a kind of synthetic method of pesticide intermediate trifluoro acetonitrile, it is characterized in that, comprise the steps:
In gas generation still, add trifluoroacetamide, tetracol phenixin, trifluoroacetic anhydride, be warmed up to 150-180 ℃, the cooling trifluoro acetonitrile that obtains after dehydration reaction;
Reaction equation is:
CF
3CONH
2+PPh
3+CCl
4→CF
3C(Cl)=NH+O＝PPh
3+CHCl
3
CF
3C(Cl)=NH+PPh
3→CF
3CN+PPh
3+HCl
。
Preferably, described temperature of reaction is 160 ℃.
beneficial effect
The invention provides a kind of reaction conditions safety gentle, reduce costs and improve productive rate, be more conducive to the trifluoro acetonitrile synthetic method of suitability for industrialized production.
Embodiment
Embodiment
In 1000L gas reaction still, add respectively 1OOKg trifluoroacetamide, 180Kg tetracol phenixin and 200L trifluoroacetic anhydride, be slowly warming up to 160 ℃, the gas producing is immediately just trifluoro acetonitrile.
Adopt trifluoroacetic anhydride, can overcome the shortcoming of other dehydration agents, for example, arrive polyphosphoric acid because viscosity is too high, even after heating, mobility is also poor.
The above; be only the specific embodiment of the present invention, but protection scope of the present invention is not limited to this, any be familiar with those skilled in the art the present invention disclose technical scope in; can expect easily changing or replacing, within all should being encompassed in protection scope of the present invention.Therefore, protection scope of the present invention should described be as the criterion with the protection domain of claim.
Claims (2)
1. a synthetic method for pesticide intermediate trifluoro acetonitrile, is characterized in that, comprises the steps:
In gas generation still, add trifluoroacetamide, tetracol phenixin, trifluoroacetic anhydride, be warmed up to 150-180 ℃, the cooling trifluoro acetonitrile that obtains after dehydration reaction;
Reaction equation is:
CF
3CONH
2+PPh
3+CCl
4→CF
3C(Cl)=NH+O＝PPh
3+CHCl
3
CF
3C(Cl)=NH+PPh
3→CF
3CN+PPh
3+HCl
。
2. synthetic method according to claim 1, is characterized in that, described temperature of reaction is 160 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410069168.8A CN103804231A (en) | 2014-02-27 | 2014-02-27 | Synthesis method for pesticide intermediate trifluoroacetonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410069168.8A CN103804231A (en) | 2014-02-27 | 2014-02-27 | Synthesis method for pesticide intermediate trifluoroacetonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103804231A true CN103804231A (en) | 2014-05-21 |
Family
ID=50701671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410069168.8A Pending CN103804231A (en) | 2014-02-27 | 2014-02-27 | Synthesis method for pesticide intermediate trifluoroacetonitrile |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103804231A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018019693A1 (en) | 2016-07-28 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Method for the production of fluoroalkyl nitriles and the corresponding fluoroalkyl tetrazoles |
| WO2018158131A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Cropscience Aktiengesellschaft | Method for the production of fluoroalkyl nitriles and of the corresponding fluoroalkyl tetrazoles |
| WO2020049436A1 (en) | 2018-09-03 | 2020-03-12 | Pi Industries Ltd. | A method for the preparation of fluoroalkyl nitriles and their use to prepare related fluoroalkyl tetrazoles |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2939878A (en) * | 1958-10-22 | 1960-06-07 | Dow Chemical Co | Preparation of fluoronitriles |
| JPS59118751A (en) * | 1982-12-24 | 1984-07-09 | Daikin Ind Ltd | Manufacturing method of fluoroalkyl nitrile |
| CN102459157A (en) * | 2009-06-08 | 2012-05-16 | 拜尔农作物科学股份公司 | Process for preparing fluoroalkyl nitriles |
| CN102746190A (en) * | 2012-08-02 | 2012-10-24 | 江苏泰特尔化工有限公司 | Preparation method of trifluoroacetonitrile |
-
2014
- 2014-02-27 CN CN201410069168.8A patent/CN103804231A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2939878A (en) * | 1958-10-22 | 1960-06-07 | Dow Chemical Co | Preparation of fluoronitriles |
| JPS59118751A (en) * | 1982-12-24 | 1984-07-09 | Daikin Ind Ltd | Manufacturing method of fluoroalkyl nitrile |
| CN102459157A (en) * | 2009-06-08 | 2012-05-16 | 拜尔农作物科学股份公司 | Process for preparing fluoroalkyl nitriles |
| CN102746190A (en) * | 2012-08-02 | 2012-10-24 | 江苏泰特尔化工有限公司 | Preparation method of trifluoroacetonitrile |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018019693A1 (en) | 2016-07-28 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Method for the production of fluoroalkyl nitriles and the corresponding fluoroalkyl tetrazoles |
| TWI736653B (en) * | 2016-07-28 | 2021-08-21 | 德商拜耳作物科學股份有限公司 | Method for preparing fluoroalkylnitriles and the corresponding fluoroalkyltetrazoles |
| WO2018158131A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Cropscience Aktiengesellschaft | Method for the production of fluoroalkyl nitriles and of the corresponding fluoroalkyl tetrazoles |
| CN110337428A (en) * | 2017-02-28 | 2019-10-15 | 拜耳作物科学股份公司 | The method for being used to prepare fluoro-alkyl nitrile and corresponding fluoro-alkyl tetrazolium |
| US10899722B2 (en) | 2017-02-28 | 2021-01-26 | Bayer Cropscience Aktiengesellschaft | Process for the preparation of fluoroalkylnitriles and the corresponding fluoroalkyltetrazoles |
| WO2020049436A1 (en) | 2018-09-03 | 2020-03-12 | Pi Industries Ltd. | A method for the preparation of fluoroalkyl nitriles and their use to prepare related fluoroalkyl tetrazoles |
| CN112654600A (en) * | 2018-09-03 | 2021-04-13 | Pi工业有限公司 | Preparation method of fluoroalkyl nitrile and application of fluoroalkyl nitrile in preparation of related fluoroalkyl tetrazole |
| KR20210053899A (en) * | 2018-09-03 | 2021-05-12 | 피아이 인더스트리스 엘티디. | Process for the preparation of fluoroalkyl nitriles and their use for preparing the corresponding fluoroalkyl tetrazoles |
| TWI825164B (en) * | 2018-09-03 | 2023-12-11 | 印度商皮埃企業有限公司 | A method for the preparation of fluoroalkyl nitriles and their use to prepare related fluoroalkyl tetrazoles |
| KR102725175B1 (en) * | 2018-09-03 | 2024-11-04 | 피아이 인더스트리스 엘티디. | Method for producing fluoroalkyl nitrile and use thereof for producing corresponding fluoroalkyl tetrazole |
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Application publication date: 20140521 |