CN104557683B - 2,3-二氯-5-三氟甲基吡啶的制备方法 - Google Patents
2,3-二氯-5-三氟甲基吡啶的制备方法 Download PDFInfo
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- CN104557683B CN104557683B CN201310466864.8A CN201310466864A CN104557683B CN 104557683 B CN104557683 B CN 104557683B CN 201310466864 A CN201310466864 A CN 201310466864A CN 104557683 B CN104557683 B CN 104557683B
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- chloro
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- catalyst
- dichloro
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical class FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical class ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 5
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical class Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 2
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000000460 chlorine Substances 0.000 abstract description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052787 antimony Inorganic materials 0.000 abstract description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052802 copper Inorganic materials 0.000 abstract description 4
- 239000010949 copper Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 2
- 230000009471 action Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- NOXIDTGVMVJLNX-UHFFFAOYSA-N ClCC=1C=CC=NC1.[Cl] Chemical compound ClCC=1C=CC=NC1.[Cl] NOXIDTGVMVJLNX-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical class F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- -1 chlorfluazurons Chemical class 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 1
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
- VLJIVLGVKMTBOD-UHFFFAOYSA-N 2-chloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=N1 VLJIVLGVKMTBOD-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
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CN201310466864.8A CN104557683B (zh) | 2013-10-09 | 2013-10-09 | 2,3-二氯-5-三氟甲基吡啶的制备方法 |
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CN201310466864.8A CN104557683B (zh) | 2013-10-09 | 2013-10-09 | 2,3-二氯-5-三氟甲基吡啶的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN104557683A CN104557683A (zh) | 2015-04-29 |
CN104557683B true CN104557683B (zh) | 2016-11-02 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106397309A (zh) * | 2016-08-31 | 2017-02-15 | 南京红太阳生物化学有限责任公司 | 一种2,3‑二氯‑5‑三氟甲基吡啶的合成方法 |
CN109529891B (zh) * | 2018-12-19 | 2022-01-11 | 重庆华歌生物化学有限公司 | 一种负载催化剂及其制备方法以及2,3,6-三氯吡啶的制备方法 |
CN110038587B (zh) * | 2019-05-14 | 2022-08-12 | 中触媒新材料股份有限公司 | 一种用于合成2,3-二氯-5-三氟甲基吡啶的催化剂及其制备方法 |
CN113527191B (zh) * | 2020-04-10 | 2023-04-07 | 新发药业有限公司 | 一种2,3-二氯-5-三氟甲基吡啶的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4331811A (en) * | 1981-03-12 | 1982-05-25 | The Dow Chemical Company | Preparation of 2,3-dichloro-5-trichloromethylpyridine |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100564359C (zh) * | 2007-06-27 | 2009-12-02 | 上海康鹏化学有限公司 | 一种2,3-二氯-5-三氯甲基吡啶的制备方法 |
-
2013
- 2013-10-09 CN CN201310466864.8A patent/CN104557683B/zh not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4331811A (en) * | 1981-03-12 | 1982-05-25 | The Dow Chemical Company | Preparation of 2,3-dichloro-5-trichloromethylpyridine |
Non-Patent Citations (2)
Title |
---|
Halogenated pyridines. II. Reactions of 3-halomethylpyridines;Horn, Ulrich et al;《Helvetica Chimica Acta》;19761231;第59卷(第1期);第190-211页 * |
Some new 2-substituted 5-trifluoromethylpyridines;Haga, Takahiro et al;《Heterocycles》;19841231;第22卷(第1期);第117-124页 * |
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CN104557683A (zh) | 2015-04-29 |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20160120 Address after: Yangshe Jiangsu province 215699 Zhangjiagang Changjiang village 1 room 107 Applicant after: Li Bo Address before: Colorado city Braun Arvada Street No. 5172 Applicant before: Yu Jianhan |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170705 Address after: 224400 Jiangsu Province, Yancheng City Funing Aoyang Industrial Park, No. 3 Patentee after: Yancheng City Zhida Chemical Co. Ltd. Address before: Yangshe Jiangsu province 215699 Zhangjiagang Changjiang village 1 room 107 Patentee before: Li Bo |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20161102 Termination date: 20191009 |