CA1264755A - PREPARATION DE TETRACHLOROPYRIDINE SYMETRIQUE A PARTIR DE .beta.-(TRICHLOROMETHYL)PYRIDINES EN PRESENCE D'UN CALALYSEUR - Google Patents
PREPARATION DE TETRACHLOROPYRIDINE SYMETRIQUE A PARTIR DE .beta.-(TRICHLOROMETHYL)PYRIDINES EN PRESENCE D'UN CALALYSEURInfo
- Publication number
- CA1264755A CA1264755A CA000480574A CA480574A CA1264755A CA 1264755 A CA1264755 A CA 1264755A CA 000480574 A CA000480574 A CA 000480574A CA 480574 A CA480574 A CA 480574A CA 1264755 A CA1264755 A CA 1264755A
- Authority
- CA
- Canada
- Prior art keywords
- trichloromethyl
- pyridine
- chlorinated
- beta
- catalyst
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 23
- DLOOKZXVYJHDIY-UHFFFAOYSA-N 2,3,4,5-tetrachloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1Cl DLOOKZXVYJHDIY-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title description 5
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000000460 chlorine Substances 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- 150000003222 pyridines Chemical class 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 7
- FATBKZJZAHWCSL-UHFFFAOYSA-N 2,3,5,6-tetrachloropyridine Chemical compound ClC1=CC(Cl)=C(Cl)N=C1Cl FATBKZJZAHWCSL-UHFFFAOYSA-N 0.000 claims description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 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 claims description 3
- XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- XLZHJPALXIYDGU-UHFFFAOYSA-N 2,6-dichloro-3-(trichloromethyl)pyridine Chemical group ClC1=CC=C(C(Cl)(Cl)Cl)C(Cl)=N1 XLZHJPALXIYDGU-UHFFFAOYSA-N 0.000 claims description 2
- VLJIVLGVKMTBOD-UHFFFAOYSA-N 2-chloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=N1 VLJIVLGVKMTBOD-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 14
- 239000000376 reactant Substances 0.000 description 6
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GPAKJVMKNDXBHH-UHFFFAOYSA-N 2,3,6-trichloropyridine Chemical compound ClC1=CC=C(Cl)C(Cl)=N1 GPAKJVMKNDXBHH-UHFFFAOYSA-N 0.000 description 2
- KAQJMEHRXVENSF-UHFFFAOYSA-N 2-(trichloromethyl)pyridine Chemical compound ClC(Cl)(Cl)C1=CC=CC=N1 KAQJMEHRXVENSF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- QMDKBCLEIGIEBO-UHFFFAOYSA-N 3-(trichloromethyl)pyridine Chemical compound ClC(Cl)(Cl)C1=CC=CN=C1 QMDKBCLEIGIEBO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910015400 FeC13 Inorganic materials 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000480574A CA1264755A (fr) | 1985-05-02 | 1985-05-02 | PREPARATION DE TETRACHLOROPYRIDINE SYMETRIQUE A PARTIR DE .beta.-(TRICHLOROMETHYL)PYRIDINES EN PRESENCE D'UN CALALYSEUR |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000480574A CA1264755A (fr) | 1985-05-02 | 1985-05-02 | PREPARATION DE TETRACHLOROPYRIDINE SYMETRIQUE A PARTIR DE .beta.-(TRICHLOROMETHYL)PYRIDINES EN PRESENCE D'UN CALALYSEUR |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1264755A true CA1264755A (fr) | 1990-01-23 |
Family
ID=4130408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000480574A Expired - Lifetime CA1264755A (fr) | 1985-05-02 | 1985-05-02 | PREPARATION DE TETRACHLOROPYRIDINE SYMETRIQUE A PARTIR DE .beta.-(TRICHLOROMETHYL)PYRIDINES EN PRESENCE D'UN CALALYSEUR |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1264755A (fr) |
-
1985
- 1985-05-02 CA CA000480574A patent/CA1264755A/fr not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3538100A (en) | Process for preparing highly chlorinated pyridines | |
| GB1599783A (en) | Partial chlorination of 3-methyl pyridine | |
| CA1162550A (fr) | Preparation de 2,3-dichloro-5-trichloromethylpyridine | |
| EP0146924B1 (fr) | Préparation de dérivés du type difluoropyridine | |
| EP0246349B1 (fr) | Méthode de chloruration sélective de la 2-chloro-5-trichlorométhyl-pyridine en position 3 | |
| Kuroboshi et al. | Synthesis of trifluoromethylamino-substituted pyridines and pyrimidines by oxidative desulfurization-fluorination | |
| US4681945A (en) | Preparation of symmetrical tetrachloropyridine from chlorinated β-(trichloromethyl) pyridines employing a catalyst | |
| US4822887A (en) | Preparation of difluoropyridine compounds | |
| EP0204848B1 (fr) | Préparation de tétrachloropyridine symétrique à partir de bêta-(trichlorométhyl)pyridines chlorées en utilisant un catalyseur | |
| US4968807A (en) | Preparation of symmetrical tetrachloropyridine from chlorinated beta(trichloromethyl) pyridines employing a catalyst | |
| US4227001A (en) | Preparation of polychlorinated pyridines from 2,4-dichloro-6-(trichloro methyl)pyridine | |
| US4275212A (en) | Method of preparing pyridinyloxyphenols and derivatives | |
| US3703521A (en) | Method for the preparation of stable 4-fluoropyridine salts | |
| US5073636A (en) | Preparation of symmetrical tetrachloropyridine from chlorinated beta-(trichloromethyl)pyridines employing a catalyst | |
| CA1084936A (fr) | Preparation de pyridines polychlorees a partir de 2,4- dichlor-6-(trichloromethyl) pyridines | |
| US5283338A (en) | Process for the preparation of 2-chloropyridines | |
| US4563530A (en) | Preparation of fluoropyridines | |
| EP0239904A2 (fr) | Procédé pour la préparation de 2,3,6-trichloropyidine et 2,3,5,6-tétrachloropyridine en phase gazeuse | |
| CA1199331A (fr) | 3-chloro-2-fluoro-5-(trifluoromethyl)-pyridine | |
| CA1270490A (fr) | Methode de chloration selective de la 2-chloro-5- (trichloromethyl) pyridine en position 3 | |
| CA2126675A1 (fr) | Methode de preparation de 2,3,5,6-tetrachloropyridine | |
| US4849523A (en) | Preparation of 2,3,4,6-tetrachloropyridine | |
| EP0044890B1 (fr) | Procédé pour la préparation de dérivés de la fluoropyridine | |
| JPS5953259B2 (ja) | ２−ヒドロキシハロゲノピリジンの製造方法 | |
| CA1202975A (fr) | Preparation de (trifluoromethyl)pyridines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |