CN102875454A - 2-氯-5-三氟甲基吡啶和2-氯-3-三氟甲基吡啶的合成方法 - Google Patents
2-氯-5-三氟甲基吡啶和2-氯-3-三氟甲基吡啶的合成方法 Download PDFInfo
- Publication number
- CN102875454A CN102875454A CN2012103955528A CN201210395552A CN102875454A CN 102875454 A CN102875454 A CN 102875454A CN 2012103955528 A CN2012103955528 A CN 2012103955528A CN 201210395552 A CN201210395552 A CN 201210395552A CN 102875454 A CN102875454 A CN 102875454A
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- Prior art keywords
- chloro
- picoline
- chlorine
- synthetic method
- trifluoromethylpyridine
- 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.)
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 17
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract description 126
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 239000007789 gas Substances 0.000 claims abstract description 25
- 239000006200 vaporizer Substances 0.000 claims abstract description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 54
- 229910052801 chlorine Inorganic materials 0.000 claims description 54
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 24
- 239000012159 carrier gas Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- RXATZPCCMYMPME-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1Cl RXATZPCCMYMPME-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 49
- 238000000034 method Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 14
- 239000003513 alkali Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 230000008016 vaporization Effects 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 238000012856 packing Methods 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 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
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- 239000005514 Flazasulfuron Substances 0.000 description 1
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- CTNMMTCXUUFYAP-UHFFFAOYSA-L difluoromanganese Chemical compound F[Mn]F CTNMMTCXUUFYAP-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Pyridine Compounds (AREA)
Abstract
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Claims (8)
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CN201210395552.8A CN102875454B (zh) | 2012-10-17 | 2012-10-17 | 2-氯-5-三氟甲基吡啶和2-氯-3-三氟甲基吡啶的合成方法 |
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CN201210395552.8A CN102875454B (zh) | 2012-10-17 | 2012-10-17 | 2-氯-5-三氟甲基吡啶和2-氯-3-三氟甲基吡啶的合成方法 |
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CN102875454A true CN102875454A (zh) | 2013-01-16 |
CN102875454B CN102875454B (zh) | 2014-10-22 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103787960A (zh) * | 2014-02-27 | 2014-05-14 | 江苏省激素研究所股份有限公司 | 一种2-氯-5-三氯甲基吡啶的合成方法 |
CN105013517A (zh) * | 2014-04-16 | 2015-11-04 | 浙江化工院科技有限公司 | 一种用于3-三氟甲基吡啶制备的催化剂 |
WO2018186460A1 (ja) * | 2017-04-04 | 2018-10-11 | 石原産業株式会社 | トリフルオロメチルピリジン類の精製方法 |
CN108997203A (zh) * | 2018-06-26 | 2018-12-14 | 江苏扬农化工集团有限公司 | 一种2,3-二氯-5-三氟甲基吡啶的高效提纯方法 |
CN110003098A (zh) * | 2018-01-05 | 2019-07-12 | 浙江省化工研究院有限公司 | 一种3-三氟甲基吡啶气相催化氯化制备2-氯-5-三氟甲基吡啶的方法 |
CN112604418A (zh) * | 2020-12-12 | 2021-04-06 | 单县欣润化工有限公司 | 一种用于处理2-氯-5-三氟甲基吡啶反应尾气的方法及*** |
US11254642B2 (en) * | 2018-01-05 | 2022-02-22 | Zhejiang Lantian Environmental Protection Hi-Tech Co., Ltd. | Method for preparing 2-chloro-5-trifluoromethylpyridine |
CN115784977A (zh) * | 2023-02-06 | 2023-03-14 | 淄博新农基作物科学有限公司 | 2-氯-3-三氟甲基吡啶的合成工艺 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4288599A (en) * | 1979-03-09 | 1981-09-08 | Ishihara Sangyo Kaisha Ltd. | Process for producing pyridine derivatives having a trifluoromethyl group at β-position thereof |
JPS56120667A (en) * | 1980-02-28 | 1981-09-22 | Ishihara Sangyo Kaisha Ltd | Preparation of chloro-beta-trifluoromethylpyridine |
CN101648905A (zh) * | 2009-09-10 | 2010-02-17 | 北京颖泰嘉和科技股份有限公司 | 2-氯-6-三氯甲基吡啶的制备方法 |
-
2012
- 2012-10-17 CN CN201210395552.8A patent/CN102875454B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4288599A (en) * | 1979-03-09 | 1981-09-08 | Ishihara Sangyo Kaisha Ltd. | Process for producing pyridine derivatives having a trifluoromethyl group at β-position thereof |
JPS56120667A (en) * | 1980-02-28 | 1981-09-22 | Ishihara Sangyo Kaisha Ltd | Preparation of chloro-beta-trifluoromethylpyridine |
CN101648905A (zh) * | 2009-09-10 | 2010-02-17 | 北京颖泰嘉和科技股份有限公司 | 2-氯-6-三氯甲基吡啶的制备方法 |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103787960A (zh) * | 2014-02-27 | 2014-05-14 | 江苏省激素研究所股份有限公司 | 一种2-氯-5-三氯甲基吡啶的合成方法 |
CN105013517A (zh) * | 2014-04-16 | 2015-11-04 | 浙江化工院科技有限公司 | 一种用于3-三氟甲基吡啶制备的催化剂 |
WO2018186460A1 (ja) * | 2017-04-04 | 2018-10-11 | 石原産業株式会社 | トリフルオロメチルピリジン類の精製方法 |
CN110475764B (zh) * | 2017-04-04 | 2023-03-31 | 石原产业株式会社 | 三氟甲基吡啶类的纯化方法 |
CN110475764A (zh) * | 2017-04-04 | 2019-11-19 | 石原产业株式会社 | 三氟甲基吡啶类的纯化方法 |
US10882824B2 (en) | 2017-04-04 | 2021-01-05 | Ishihara Sangyo Kaisha, Ltd. | Method for purifying trifluoromethylpyridines |
US11254642B2 (en) * | 2018-01-05 | 2022-02-22 | Zhejiang Lantian Environmental Protection Hi-Tech Co., Ltd. | Method for preparing 2-chloro-5-trifluoromethylpyridine |
CN110003098A (zh) * | 2018-01-05 | 2019-07-12 | 浙江省化工研究院有限公司 | 一种3-三氟甲基吡啶气相催化氯化制备2-氯-5-三氟甲基吡啶的方法 |
CN110003098B (zh) * | 2018-01-05 | 2020-11-17 | 浙江省化工研究院有限公司 | 一种3-三氟甲基吡啶气相催化氯化制备2-氯-5-三氟甲基吡啶的方法 |
CN108997203B (zh) * | 2018-06-26 | 2020-08-14 | 江苏扬农化工集团有限公司 | 一种2,3-二氯-5-三氟甲基吡啶的高效提纯方法 |
CN108997203A (zh) * | 2018-06-26 | 2018-12-14 | 江苏扬农化工集团有限公司 | 一种2,3-二氯-5-三氟甲基吡啶的高效提纯方法 |
CN112604418A (zh) * | 2020-12-12 | 2021-04-06 | 单县欣润化工有限公司 | 一种用于处理2-氯-5-三氟甲基吡啶反应尾气的方法及*** |
CN115784977A (zh) * | 2023-02-06 | 2023-03-14 | 淄博新农基作物科学有限公司 | 2-氯-3-三氟甲基吡啶的合成工艺 |
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