JPS60112751A - テトラフルオロフタロニトリル類の製法 - Google Patents
テトラフルオロフタロニトリル類の製法Info
- Publication number
- JPS60112751A JPS60112751A JP21947483A JP21947483A JPS60112751A JP S60112751 A JPS60112751 A JP S60112751A JP 21947483 A JP21947483 A JP 21947483A JP 21947483 A JP21947483 A JP 21947483A JP S60112751 A JPS60112751 A JP S60112751A
- Authority
- JP
- Japan
- Prior art keywords
- tetrachlorophthalonitrile
- benzonitrile
- reaction
- fluorinating agent
- solvent
- 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
- OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 36
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 22
- OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000012025 fluorinating agent Substances 0.000 claims abstract description 11
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 11
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 11
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 13
- PCRSJGWFEMHHEW-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonitrile Chemical group FC1=C(F)C(C#N)=C(F)C(F)=C1C#N PCRSJGWFEMHHEW-UHFFFAOYSA-N 0.000 claims description 7
- TXRVDQMSXQKAPG-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzene-1,4-dicarbonitrile Chemical group ClC1=C(Cl)C(C#N)=C(Cl)C(Cl)=C1C#N TXRVDQMSXQKAPG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 150000004673 fluoride salts Chemical class 0.000 claims description 2
- 230000002269 spontaneous effect Effects 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
- 239000002904 solvent Substances 0.000 abstract description 21
- 150000002367 halogens Chemical class 0.000 abstract description 18
- 229910052736 halogen Inorganic materials 0.000 abstract description 15
- WVHMPQKZPHOCRD-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(C#N)=C1F WVHMPQKZPHOCRD-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000007086 side reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000005539 carbonized material Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- -1 aromatic halide Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940060037 fluorine Drugs 0.000 description 3
- 235000019000 fluorine Nutrition 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002633 crown compound Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 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
- 230000002194 synthesizing effect Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000102542 Kara Species 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
- 238000004458 analytical method Methods 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
- 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- UTFBGYDHJGSHCK-UHFFFAOYSA-G heptasodium heptafluoride Chemical compound [F-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[F-].[F-].[F-].[F-].[F-].[F-] UTFBGYDHJGSHCK-UHFFFAOYSA-G 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical class N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 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
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 229910021561 transition metal fluoride Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21947483A JPS60112751A (ja) | 1983-11-24 | 1983-11-24 | テトラフルオロフタロニトリル類の製法 |
| EP84300911A EP0120575B1 (en) | 1983-02-18 | 1984-02-14 | Organic fluorine compounds |
| DE8484300911T DE3478681D1 (en) | 1983-02-18 | 1984-02-14 | Organic fluorine compounds |
| US06/776,085 US4684734A (en) | 1983-02-18 | 1985-09-13 | Method for manufacture or organic fluorine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21947483A JPS60112751A (ja) | 1983-11-24 | 1983-11-24 | テトラフルオロフタロニトリル類の製法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5847884A Division JPS60112750A (ja) | 1984-03-28 | 1984-03-28 | テトラフルオロイソフタロニトリル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60112751A true JPS60112751A (ja) | 1985-06-19 |
| JPS635023B2 JPS635023B2 (enrdf_load_stackoverflow) | 1988-02-01 |
Family
ID=16735995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21947483A Granted JPS60112751A (ja) | 1983-02-18 | 1983-11-24 | テトラフルオロフタロニトリル類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60112751A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7741426B2 (en) | 2003-06-23 | 2010-06-22 | Nippon Shokubai Co., Ltd | Method for production of fluorinated phenylenediamine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5139633A (ja) * | 1974-09-30 | 1976-04-02 | Daikin Ind Ltd | Futsusokahoho |
| JPS54109932A (en) * | 1978-01-26 | 1979-08-29 | Basf Ag | Manufacture of fluorobenzol |
| JPS57197226A (en) * | 1981-05-30 | 1982-12-03 | Dainippon Ink & Chem Inc | Preparation of aromatic fluorine compound |
| JPS6094919A (ja) * | 1983-10-31 | 1985-05-28 | Nippon Shokubai Kagaku Kogyo Co Ltd | 有機フツ素化物の製法 |
-
1983
- 1983-11-24 JP JP21947483A patent/JPS60112751A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5139633A (ja) * | 1974-09-30 | 1976-04-02 | Daikin Ind Ltd | Futsusokahoho |
| JPS54109932A (en) * | 1978-01-26 | 1979-08-29 | Basf Ag | Manufacture of fluorobenzol |
| JPS57197226A (en) * | 1981-05-30 | 1982-12-03 | Dainippon Ink & Chem Inc | Preparation of aromatic fluorine compound |
| JPS6094919A (ja) * | 1983-10-31 | 1985-05-28 | Nippon Shokubai Kagaku Kogyo Co Ltd | 有機フツ素化物の製法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7741426B2 (en) | 2003-06-23 | 2010-06-22 | Nippon Shokubai Co., Ltd | Method for production of fluorinated phenylenediamine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS635023B2 (enrdf_load_stackoverflow) | 1988-02-01 |
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