JPS60149566A - テトラフルオロシアノピリジン類の製法 - Google Patents
テトラフルオロシアノピリジン類の製法Info
- Publication number
- JPS60149566A JPS60149566A JP562984A JP562984A JPS60149566A JP S60149566 A JPS60149566 A JP S60149566A JP 562984 A JP562984 A JP 562984A JP 562984 A JP562984 A JP 562984A JP S60149566 A JPS60149566 A JP S60149566A
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyridine
- tetrafluoro
- tetrachloro
- tetrachlorocyanopyridine
- reaction
- 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
- XYFHRSUUAGJYOZ-UHFFFAOYSA-N 3,4,5,6-tetrafluoropyridine-2-carbonitrile Chemical compound FC1=NC(C#N)=C(F)C(F)=C1F XYFHRSUUAGJYOZ-UHFFFAOYSA-N 0.000 title claims description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 22
- KFPBGJYBKSQIAI-UHFFFAOYSA-N 3,4,5,6-tetrachloropyridine-2-carbonitrile Chemical compound ClC1=NC(C#N)=C(Cl)C(Cl)=C1Cl KFPBGJYBKSQIAI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 11
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 11
- 239000012025 fluorinating agent Substances 0.000 claims abstract description 10
- RVYYWCWXJDYEIO-UHFFFAOYSA-N 2,4,5,6-tetrafluoropyridine-3-carbonitrile Chemical compound FC1=NC(F)=C(C#N)C(F)=C1F RVYYWCWXJDYEIO-UHFFFAOYSA-N 0.000 claims abstract description 8
- WQGYOIRZZWUJJU-UHFFFAOYSA-N 2,3,5,6-tetrachloropyridine-4-carbonitrile Chemical compound ClC1=NC(Cl)=C(Cl)C(C#N)=C1Cl WQGYOIRZZWUJJU-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLORIERFMJHASL-UHFFFAOYSA-N 2,4,5,6-tetrachloropyridine-3-carbonitrile Chemical compound ClC1=NC(Cl)=C(C#N)C(Cl)=C1Cl XLORIERFMJHASL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 150000004673 fluoride salts Chemical class 0.000 claims description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910001618 alkaline earth metal fluoride Chemical class 0.000 claims 1
- 230000002269 spontaneous effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 22
- 239000002994 raw material Substances 0.000 abstract description 8
- JXISJBVJNUKKBK-UHFFFAOYSA-N 2,3,5,6-tetrafluoropyridine-4-carbonitrile Chemical compound FC1=NC(F)=C(F)C(C#N)=C1F JXISJBVJNUKKBK-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 aromatic halide Chemical class 0.000 description 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000002633 crown compound Substances 0.000 description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- JFDZBHWFFUWGJE-KWCOIAHCSA-N benzonitrile Chemical group N#[11C]C1=CC=CC=C1 JFDZBHWFFUWGJE-KWCOIAHCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910021561 transition metal fluoride Inorganic materials 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP562984A JPS60149566A (ja) | 1984-01-18 | 1984-01-18 | テトラフルオロシアノピリジン類の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP562984A JPS60149566A (ja) | 1984-01-18 | 1984-01-18 | テトラフルオロシアノピリジン類の製法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5847784A Division JPS60152467A (ja) | 1984-03-28 | 1984-03-28 | テトラフルオロ−３−シアノピリジン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60149566A true JPS60149566A (ja) | 1985-08-07 |
| JPS6153345B2 JPS6153345B2 (enrdf_load_stackoverflow) | 1986-11-17 |
Family
ID=11616443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP562984A Granted JPS60149566A (ja) | 1984-01-18 | 1984-01-18 | テトラフルオロシアノピリジン類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60149566A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629424A (en) * | 1967-12-26 | 1971-12-21 | Dow Chemical Co | Cyanofluoropyridines and fungicidal compositions and methods for using the same |
-
1984
- 1984-01-18 JP JP562984A patent/JPS60149566A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629424A (en) * | 1967-12-26 | 1971-12-21 | Dow Chemical Co | Cyanofluoropyridines and fungicidal compositions and methods for using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6153345B2 (enrdf_load_stackoverflow) | 1986-11-17 |