JPS601307B2 - テトラクロロピリジンの製造法 - Google Patents
テトラクロロピリジンの製造法Info
- Publication number
- JPS601307B2 JPS601307B2 JP51124760A JP12476076A JPS601307B2 JP S601307 B2 JPS601307 B2 JP S601307B2 JP 51124760 A JP51124760 A JP 51124760A JP 12476076 A JP12476076 A JP 12476076A JP S601307 B2 JPS601307 B2 JP S601307B2
- Authority
- JP
- Japan
- Prior art keywords
- pcp
- manufacturing
- reaction
- zinc
- temperature
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- DLOOKZXVYJHDIY-UHFFFAOYSA-N 2,3,4,5-tetrachloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1Cl DLOOKZXVYJHDIY-UHFFFAOYSA-N 0.000 title claims description 5
- 239000011701 zinc Substances 0.000 claims description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 description 29
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- FATBKZJZAHWCSL-UHFFFAOYSA-N 2,3,5,6-tetrachloropyridine Chemical compound ClC1=CC(Cl)=C(Cl)N=C1Cl FATBKZJZAHWCSL-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VMHZXXPDUOVTHD-UHFFFAOYSA-N 2,3,4-trichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1Cl VMHZXXPDUOVTHD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000013259 porous coordination polymer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012808 vapor phase Substances 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7631253A FR2367747A1 (fr) | 1976-10-18 | 1976-10-18 | Procede de production de tetrachloropyridine |
| JP51124760A JPS601307B2 (ja) | 1976-10-18 | 1976-10-18 | テトラクロロピリジンの製造法 |
| CA263,590A CA1056382A (en) | 1976-10-18 | 1976-10-18 | Preparation of tetrachloropyridine |
| GB43176/76A GB1499650A (en) | 1976-10-18 | 1976-10-18 | Process for production of 2,3,5,6-tetrachloropyridine |
| DE2647143A DE2647143C3 (de) | 1976-10-18 | 1976-10-19 | Verfahren zur Herstellung von 233.6-Tetrachlorpyridin |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7631253A FR2367747A1 (fr) | 1976-10-18 | 1976-10-18 | Procede de production de tetrachloropyridine |
| JP51124760A JPS601307B2 (ja) | 1976-10-18 | 1976-10-18 | テトラクロロピリジンの製造法 |
| CA263,590A CA1056382A (en) | 1976-10-18 | 1976-10-18 | Preparation of tetrachloropyridine |
| GB43176/76A GB1499650A (en) | 1976-10-18 | 1976-10-18 | Process for production of 2,3,5,6-tetrachloropyridine |
| DE2647143A DE2647143C3 (de) | 1976-10-18 | 1976-10-19 | Verfahren zur Herstellung von 233.6-Tetrachlorpyridin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5350175A JPS5350175A (en) | 1978-05-08 |
| JPS601307B2 true JPS601307B2 (ja) | 1985-01-14 |
Family
ID=27508074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51124760A Expired JPS601307B2 (ja) | 1976-10-18 | 1976-10-18 | テトラクロロピリジンの製造法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS601307B2 (enExample) |
| CA (1) | CA1056382A (enExample) |
| DE (1) | DE2647143C3 (enExample) |
| FR (1) | FR2367747A1 (enExample) |
| GB (1) | GB1499650A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4783536A (en) * | 1985-02-07 | 1988-11-08 | The Dow Chemical Company | Selective reduction of pentachloropyridine to 2,3,5,6-tetrachloropyridine with zinc dust in basic media |
| US4592810A (en) * | 1985-03-18 | 1986-06-03 | The Dow Chemical Company | Electrocatalytic production of 2,3,5,6-tetrachloropyridine from pentachloropyridine |
| AU4996299A (en) | 1998-07-15 | 2000-02-07 | Reilly Industries, Inc. | Dechlorination of pyridines in acidic, zinc-containing mediums |
-
1976
- 1976-10-18 GB GB43176/76A patent/GB1499650A/en not_active Expired
- 1976-10-18 CA CA263,590A patent/CA1056382A/en not_active Expired
- 1976-10-18 JP JP51124760A patent/JPS601307B2/ja not_active Expired
- 1976-10-18 FR FR7631253A patent/FR2367747A1/fr active Granted
- 1976-10-19 DE DE2647143A patent/DE2647143C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2647143B2 (de) | 1978-08-10 |
| FR2367747B1 (enExample) | 1979-03-02 |
| DE2647143A1 (de) | 1978-04-27 |
| JPS5350175A (en) | 1978-05-08 |
| DE2647143C3 (de) | 1979-04-05 |
| CA1056382A (en) | 1979-06-12 |
| GB1499650A (en) | 1978-02-01 |
| FR2367747A1 (fr) | 1978-05-12 |
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