JPS58206563A - β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法 - Google Patents
β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法Info
- Publication number
- JPS58206563A JPS58206563A JP9043582A JP9043582A JPS58206563A JP S58206563 A JPS58206563 A JP S58206563A JP 9043582 A JP9043582 A JP 9043582A JP 9043582 A JP9043582 A JP 9043582A JP S58206563 A JPS58206563 A JP S58206563A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylpyridine
- chloro
- beta
- alpha
- compound
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 5
- -1 trifluoromethylpyridine compound Chemical class 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 239000002994 raw material Substances 0.000 abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 7
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 abstract description 2
- 239000012808 vapor phase Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UJJMLGJZQGGQAZ-UHFFFAOYSA-N 2-(fluoromethyl)pyridine Chemical compound FCC1=CC=CC=N1 UJJMLGJZQGGQAZ-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- ZFCZNQZILNNPBH-UHFFFAOYSA-N 2,3-dichloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(Cl)=C1Cl ZFCZNQZILNNPBH-UHFFFAOYSA-N 0.000 description 2
- ADVQMCQMDHBTHJ-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(Cl)=N1 ADVQMCQMDHBTHJ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- XFOQWQKDSMIPHT-UHFFFAOYSA-N 2,3-dichloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=N1 XFOQWQKDSMIPHT-UHFFFAOYSA-N 0.000 description 1
- GFTRYJQAASFSIB-UHFFFAOYSA-N 2,5-dichloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=NC=C1Cl GFTRYJQAASFSIB-UHFFFAOYSA-N 0.000 description 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- WSALYASKYGIWGP-UHFFFAOYSA-N 3,5-dichloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=NC=C(Cl)C=C1Cl WSALYASKYGIWGP-UHFFFAOYSA-N 0.000 description 1
- WDFIJOQQKFWJEA-UHFFFAOYSA-N 3,6-dichloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=NC(Cl)=CC=C1Cl WDFIJOQQKFWJEA-UHFFFAOYSA-N 0.000 description 1
- IJOSVNBGIKAARU-UHFFFAOYSA-N 3-chloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=NC=CC=C1Cl IJOSVNBGIKAARU-UHFFFAOYSA-N 0.000 description 1
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241001648341 Orites Species 0.000 description 1
- 101150109054 RRD1 gene Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000000571 coke 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 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
- 239000010959 steel Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9043582A JPS58206563A (ja) | 1982-05-27 | 1982-05-27 | β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9043582A JPS58206563A (ja) | 1982-05-27 | 1982-05-27 | β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58206563A true JPS58206563A (ja) | 1983-12-01 |
| JPS6135183B2 JPS6135183B2 (enrdf_load_stackoverflow) | 1986-08-12 |
Family
ID=13998524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9043582A Granted JPS58206563A (ja) | 1982-05-27 | 1982-05-27 | β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58206563A (enrdf_load_stackoverflow) |
-
1982
- 1982-05-27 JP JP9043582A patent/JPS58206563A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6135183B2 (enrdf_load_stackoverflow) | 1986-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4288599A (en) | Process for producing pyridine derivatives having a trifluoromethyl group at β-position thereof | |
| CA1132572A (en) | Process for producing 2-chloro-5- trichloromethyl pyridine | |
| KR860001905B1 (ko) | 3-클로로-5-트리플루오로메틸피리딘의 제조방법 | |
| GB2045761A (en) | Process for producing chloro-trifluoromethylpyridines | |
| JPS6315270B2 (enrdf_load_stackoverflow) | ||
| US4417055A (en) | Process for producing a β-trifluoromethylpyridine | |
| US4420618A (en) | Process for producing 5-chloro-β-trifluoromethylpyridines | |
| EP0042696A1 (en) | Process for producing trifluoromethylpyridines | |
| US2406195A (en) | Manufacture of the higher chlorides of methane | |
| JPS58206563A (ja) | β−クロロα又はγ−トリフルオロメチルピリジン系化合物の製造方法 | |
| JPS61249964A (ja) | ３，４，５，６−テトラクロロ−２−トリクロロメチルピリジンに富む混合物の調製方法 | |
| WO2018186460A1 (ja) | トリフルオロメチルピリジン類の精製方法 | |
| JPH0219108B2 (enrdf_load_stackoverflow) | ||
| US2399361A (en) | Manufacture of cyanogen | |
| US2621111A (en) | Production of silicon chlorides | |
| JPS6130667B2 (enrdf_load_stackoverflow) | ||
| US4801716A (en) | Process for preparing 2,3,4,5-tetrachloro-6-(trichloromethyl) pyridine | |
| JPS6130666B2 (enrdf_load_stackoverflow) | ||
| US1900276A (en) | Process for the preparation of ethylidene chloride | |
| JPS6365665B2 (enrdf_load_stackoverflow) | ||
| EP0363404B1 (en) | Process for the production of 2,3,5,6-tetrachloropyridine and 2,3,6-trichloropyridine | |
| JPS62185082A (ja) | テトラクロロ無水フタル酸の製造方法 | |
| US4388251A (en) | Method for preparing 2-chlorobenzoyl chloride | |
| JPS6134415B2 (enrdf_load_stackoverflow) | ||
| US3505010A (en) | Manufacture of ammonium bromide and carbon monoxide from polybromomethanes |