JPS6134415B2 - - Google Patents

Info

Publication number: JPS6134415B2
Authority: JP; Japan
Prior art keywords: reaction; tcp; chloro; fluoride; trichloromethylpyridine
Prior art date: 1979-03-19
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.): Expired

Application number

JP3206779A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55124762A (en

Inventor

Ryuzo Nishama

Kanichi Fujikawa

Isao Yokomichi

Yasuhiro Tsujii

Shigeyuki Nishimura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha Ltd

Priority date (The priority date 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 date listed.)

1979-03-19

Filing date

1979-03-19

Publication date

1986-08-07

1979-03-19 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1979-03-19 Priority to JP3206779A priority Critical patent/JPS55124762A/ja

1980-03-05 Priority to US06/127,468 priority patent/US4266064A/en

1980-03-13 Priority to DE19803009695 priority patent/DE3009695A1/de

1980-03-17 Priority to FR8005925A priority patent/FR2451916A1/fr

1980-03-17 Priority to BE0/199823A priority patent/BE882263A/fr

1980-03-17 Priority to CA347,770A priority patent/CA1125763A/en

1980-03-18 Priority to CH212780A priority patent/CH642631A5/de

1980-05-19 Priority to GB8009305A priority patent/GB2045761B/en

1980-09-26 Publication of JPS55124762A publication Critical patent/JPS55124762A/ja

1986-08-07 Publication of JPS6134415B2 publication Critical patent/JPS6134415B2/ja

Status Granted legal-status Critical Current

Links

238000006243 chemical reaction Methods 0.000 claims description 19
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
VYOZKLLJJHRFNA-UHFFFAOYSA-N [F].N Chemical compound [F].N VYOZKLLJJHRFNA-UHFFFAOYSA-N 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 12
239000000047 product Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
239000002994 raw material Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 5
JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 4
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
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 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
GDFCUTHAIBYLSX-UHFFFAOYSA-N 2,5-dichloro-3-(difluoromethyl)pyridine Chemical compound FC(F)C1=CC(Cl)=CN=C1Cl GDFCUTHAIBYLSX-UHFFFAOYSA-N 0.000 description 2
GCARAYBZTVIMNF-UHFFFAOYSA-N 2-chloro-3-(dichloromethyl)-5-fluoropyridine Chemical compound FC1=CN=C(Cl)C(C(Cl)Cl)=C1 GCARAYBZTVIMNF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910015475 FeF 2 Inorganic materials 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000003682 fluorination reaction Methods 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical compound [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 description 2
229910001512 metal fluoride Inorganic materials 0.000 description 2
DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
ULRPBTXNKBYTSK-UHFFFAOYSA-N 2,3,6-trichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=C(Cl)N=C1Cl ULRPBTXNKBYTSK-UHFFFAOYSA-N 0.000 description 1
ZJNBCPFIEDYDFH-UHFFFAOYSA-N 2,3,6-trichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)N=C1Cl ZJNBCPFIEDYDFH-UHFFFAOYSA-N 0.000 description 1
XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 description 1
XLZHJPALXIYDGU-UHFFFAOYSA-N 2,6-dichloro-3-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C(Cl)=N1 XLZHJPALXIYDGU-UHFFFAOYSA-N 0.000 description 1
UPWAAFFFSGQECJ-UHFFFAOYSA-N 2,6-dichloro-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1Cl UPWAAFFFSGQECJ-UHFFFAOYSA-N 0.000 description 1
TZKVGCQBQQFWOV-UHFFFAOYSA-N 2-chloro-3-(trichloromethyl)pyridine Chemical compound ClC1=NC=CC=C1C(Cl)(Cl)Cl TZKVGCQBQQFWOV-UHFFFAOYSA-N 0.000 description 1
RXATZPCCMYMPME-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1Cl RXATZPCCMYMPME-UHFFFAOYSA-N 0.000 description 1
YBZWGFJIXKCVPO-UHFFFAOYSA-N 3-chloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CN=CC(C(Cl)(Cl)Cl)=C1 YBZWGFJIXKCVPO-UHFFFAOYSA-N 0.000 description 1
OMRCXTBFBBWTDL-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=CC(Cl)=C1 OMRCXTBFBBWTDL-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000011810 insulating material Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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)

JP3206779A 1979-03-19 1979-03-19 Preparation of beta-trifluoromethylpyridine Granted JPS55124762A (en)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
JP3206779A JPS55124762A (en)	1979-03-19	1979-03-19	Preparation of beta-trifluoromethylpyridine
US06/127,468 US4266064A (en)	1979-03-19	1980-03-05	Process for producing chloro β-trifluoromethylpyridines
DE19803009695 DE3009695A1 (de)	1979-03-19	1980-03-13	Verfahren zur herstellung von chlor- beta -trifluormethylpyridinen
FR8005925A FR2451916A1 (fr)	1979-03-19	1980-03-17	Procede de production de chloro-b-trifluoromethylpyridines
BE0/199823A BE882263A (fr)	1979-03-19	1980-03-17	Procede de production de chloro-beta-trifluoromethylpyridines
CA347,770A CA1125763A (en)	1979-03-19	1980-03-17	PROCESS FOR PRODUCING CHLORO .beta.-TRIFLUORO- METHYLPYRIDINES
CH212780A CH642631A5 (de)	1979-03-19	1980-03-18	Verfahren zur herstellung von chlor-beta-trifluormethylpyridinen.
GB8009305A GB2045761B (en)	1979-03-19	1980-05-19	Process for producing chloro-trifluoromethylpyridines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3206779A JPS55124762A (en)	1979-03-19	1979-03-19	Preparation of beta-trifluoromethylpyridine

Publications (2)

Publication Number	Publication Date
JPS55124762A JPS55124762A (en)	1980-09-26
JPS6134415B2 true JPS6134415B2 (de)	1986-08-07

Family

ID=12348525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3206779A Granted JPS55124762A (en)	1979-03-19	1979-03-19	Preparation of beta-trifluoromethylpyridine

Country Status (2)

Country	Link
JP (1)	JPS55124762A (de)
BE (1)	BE882263A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5629573A (en) *	1979-08-16	1981-03-24	Daikin Ind Ltd	Preparation of halogeno-trifluoromethyl-pyridine
CN110818623A (zh)	2018-08-07	2020-02-21	石原产业株式会社	2-氯-3-三氟甲基吡啶的分离、纯化方法

1979
- 1979-03-19 JP JP3206779A patent/JPS55124762A/ja active Granted
1980
- 1980-03-17 BE BE0/199823A patent/BE882263A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS55124762A (en)	1980-09-26
BE882263A (fr)	1980-09-17

Publication	Publication Date	Title
CA1132572A (en)	1982-09-28	Process for producing 2-chloro-5- trichloromethyl pyridine
US4288599A (en)	1981-09-08	Process for producing pyridine derivatives having a trifluoromethyl group at β-position thereof
US4266064A (en)	1981-05-05	Process for producing chloro β-trifluoromethylpyridines
EP0078410B1 (de)	1987-05-27	Verfahren zur Herstellung von 3-Chloro-5-Trifluoromethylpyridinen
EP0065358B1 (de)	1986-05-28	Herstellung von 3-Trichlormethyl- und 3-Trifluormethylpyridinen
JPH0133465B2 (de)	1989-07-13
JP2020023489A (ja)	2020-02-13	２−クロロ−３−トリフルオロメチルピリジンの分離、精製方法
EP0042696B1 (de)	1983-11-16	Verfahren zur Herstellung von Trifluormethyl-pyridinen
US4420618A (en)	1983-12-13	Process for producing 5-chloro-β-trifluoromethylpyridines
US4417055A (en)	1983-11-22	Process for producing a β-trifluoromethylpyridine
WO2018186460A1 (ja)	2018-10-11	トリフルオロメチルピリジン類の精製方法
JPS6134415B2 (de)	1986-08-07
JPH0219108B2 (de)	1990-04-27
US4801716A (en)	1989-01-31	Process for preparing 2,3,4,5-tetrachloro-6-(trichloromethyl) pyridine
JPS6130667B2 (de)	1986-07-15
US4563530A (en)	1986-01-07	Preparation of fluoropyridines
JPS6130666B2 (de)	1986-07-15
JPS6134416B2 (de)	1986-08-07
KR840000698B1 (ko)	1984-05-21	β위치에 트리플루오로 메틸기를 갖는 피리딘 유도체의 제조방법
JP2588268B2 (ja)	1997-03-05	２，３，５，６‐テトラクロロピリジン及び２，３，６‐トリクロロピリジンの製造法
US3591597A (en)	1971-07-06	Vapor phase production of monochlorocyanopyridines
JPS6130665B2 (de)	1986-07-15
CA1304089C (en)	1992-06-23	Process for preparing 2,3,4,5-tetrachloro-6- (trichloromethyl) pyridine
JPS6130664B2 (de)	1986-07-15
JPS6130663B2 (de)	1986-07-15