JPS6135183B2 - - Google Patents
Info
- Publication number
- JPS6135183B2 JPS6135183B2 JP9043582A JP9043582A JPS6135183B2 JP S6135183 B2 JPS6135183 B2 JP S6135183B2 JP 9043582 A JP9043582 A JP 9043582A JP 9043582 A JP9043582 A JP 9043582A JP S6135183 B2 JPS6135183 B2 JP S6135183B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylpyridine
- dichloro
- catalyst
- reaction
- chlorine
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- -1 trifluoromethylpyridine compound Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 229910001510 metal chloride Inorganic materials 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 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
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000002245 particle 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
- RMQHBNLAFHDMEN-UHFFFAOYSA-N (4,4,4-trifluoro-2-oxobutyl) dihydrogen phosphate Chemical compound OP(O)(=O)OCC(=O)CC(F)(F)F RMQHBNLAFHDMEN-UHFFFAOYSA-N 0.000 description 1
- HZSKAVACTPGTRH-UHFFFAOYSA-N 2,3,5-trichloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=NC(Cl)=C(Cl)C=C1Cl HZSKAVACTPGTRH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- PWVHFDAKFGGYKJ-UHFFFAOYSA-N 3,5-dichloro-2-(trichloromethyl)pyridine Chemical compound ClC1=CN=C(C(Cl)(Cl)Cl)C(Cl)=C1 PWVHFDAKFGGYKJ-UHFFFAOYSA-N 0.000 description 1
- NINXGROOEMZYSZ-UHFFFAOYSA-N 3-chloro-4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=NC=CC(C(F)(F)F)=C1Cl NINXGROOEMZYSZ-UHFFFAOYSA-N 0.000 description 1
- YNYROPYZSZBORI-UHFFFAOYSA-N 3-chloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1Cl YNYROPYZSZBORI-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 229910021529 ammonia Inorganic materials 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
- 239000000571 coke Substances 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
- 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
- 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
- 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
- 239000011810 insulating material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture 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 JPS58206563A (ja) | 1983-12-01 |
| JPS6135183B2 true JPS6135183B2 (US20020051482A1-20020502-M00020.png) | 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 (US20020051482A1-20020502-M00020.png) |
-
1982
- 1982-05-27 JP JP9043582A patent/JPS58206563A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58206563A (ja) | 1983-12-01 |
