DE2006607A1 - Verfahren zur Herstellung von fluorhaltigen Pyridinderivaten - Google Patents
Verfahren zur Herstellung von fluorhaltigen PyridinderivatenInfo
- Publication number
- DE2006607A1 DE2006607A1 DE19702006607 DE2006607A DE2006607A1 DE 2006607 A1 DE2006607 A1 DE 2006607A1 DE 19702006607 DE19702006607 DE 19702006607 DE 2006607 A DE2006607 A DE 2006607A DE 2006607 A1 DE2006607 A1 DE 2006607A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- fluorine
- hydrogen fluoride
- temperature
- substituted pyridine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000003222 pyridines Chemical class 0.000 title claims description 5
- 229910052731 fluorine Inorganic materials 0.000 title claims description 4
- 239000011737 fluorine Substances 0.000 title claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011651 chromium Substances 0.000 claims description 6
- -1 chlorine-substituted pyridine Chemical class 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 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 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 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
- XOUHUCXTEKWSMO-UHFFFAOYSA-N 3,4,5-trichloro-2,6-difluoropyridine Chemical compound FC1=NC(F)=C(Cl)C(Cl)=C1Cl XOUHUCXTEKWSMO-UHFFFAOYSA-N 0.000 description 1
- PKSORSNCSXBXOT-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluoropyridine Chemical compound FC1=NC(F)=C(Cl)C(F)=C1Cl PKSORSNCSXBXOT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 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
- 241001122767 Theaceae Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB995369 | 1969-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2006607A1 true DE2006607A1 (de) | 1970-09-10 |
Family
ID=9881816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702006607 Pending DE2006607A1 (de) | 1969-02-25 | 1970-02-13 | Verfahren zur Herstellung von fluorhaltigen Pyridinderivaten |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4815948B1 (enrdf_load_stackoverflow) |
| BE (1) | BE746246A (enrdf_load_stackoverflow) |
| CH (1) | CH524603A (enrdf_load_stackoverflow) |
| DE (1) | DE2006607A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2032395A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1234543A (enrdf_load_stackoverflow) |
| IE (1) | IE33943B1 (enrdf_load_stackoverflow) |
| IL (1) | IL33799A (enrdf_load_stackoverflow) |
| NL (1) | NL7001098A (enrdf_load_stackoverflow) |
| ZA (1) | ZA70326B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999432A (en) * | 1989-08-28 | 1991-03-12 | Dowelanco | Fluorination with hydrogen fluoride |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4266064A (en) * | 1979-03-19 | 1981-05-05 | Ishihara Sangyo Kaisha Ltd. | Process for producing chloro β-trifluoromethylpyridines |
-
1969
- 1969-02-25 GB GB995369A patent/GB1234543A/en not_active Expired
-
1970
- 1970-01-16 IE IE61/70A patent/IE33943B1/xx unknown
- 1970-01-19 ZA ZA700326A patent/ZA70326B/xx unknown
- 1970-01-27 NL NL7001098A patent/NL7001098A/xx unknown
- 1970-01-28 IL IL33799A patent/IL33799A/xx unknown
- 1970-02-09 CH CH182870A patent/CH524603A/de not_active IP Right Cessation
- 1970-02-13 DE DE19702006607 patent/DE2006607A1/de active Pending
- 1970-02-18 JP JP45013525A patent/JPS4815948B1/ja active Pending
- 1970-02-19 BE BE746246D patent/BE746246A/xx unknown
- 1970-02-24 FR FR7006664A patent/FR2032395A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999432A (en) * | 1989-08-28 | 1991-03-12 | Dowelanco | Fluorination with hydrogen fluoride |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2032395A1 (enrdf_load_stackoverflow) | 1970-11-27 |
| IE33943B1 (en) | 1974-12-11 |
| JPS4815948B1 (enrdf_load_stackoverflow) | 1973-05-18 |
| IL33799A (en) | 1974-01-14 |
| BE746246A (fr) | 1970-08-19 |
| ZA70326B (en) | 1971-08-25 |
| NL7001098A (enrdf_load_stackoverflow) | 1970-08-27 |
| IE33943L (en) | 1970-08-25 |
| CH524603A (de) | 1972-06-30 |
| GB1234543A (enrdf_load_stackoverflow) | 1971-06-03 |
| IL33799A0 (en) | 1970-05-21 |
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