JPH0216746B2 - - Google Patents
Info
- Publication number
- JPH0216746B2 JPH0216746B2 JP11348083A JP11348083A JPH0216746B2 JP H0216746 B2 JPH0216746 B2 JP H0216746B2 JP 11348083 A JP11348083 A JP 11348083A JP 11348083 A JP11348083 A JP 11348083A JP H0216746 B2 JPH0216746 B2 JP H0216746B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- potassium fluoride
- chlorobenzonitrile
- 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.)
- Expired
Links
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- -1 chlorobenzonitrile compound Chemical class 0.000 claims description 8
- 235000003270 potassium fluoride Nutrition 0.000 claims description 8
- 239000011698 potassium fluoride Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical class FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 description 2
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical group ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- INICGXSKJYKEIV-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(Cl)=C1Cl INICGXSKJYKEIV-UHFFFAOYSA-N 0.000 description 1
- QTUXEYXZJLVGOA-UHFFFAOYSA-N 2,3,6-trichlorobenzonitrile Chemical compound ClC1=CC=C(Cl)C(C#N)=C1Cl QTUXEYXZJLVGOA-UHFFFAOYSA-N 0.000 description 1
- PGODHCIOIPODFE-UHFFFAOYSA-N 2,4,6-trichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Cl)=C1 PGODHCIOIPODFE-UHFFFAOYSA-N 0.000 description 1
- HTKFGTCCOJIUIK-UHFFFAOYSA-N 2,4,6-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C(F)=C1 HTKFGTCCOJIUIK-UHFFFAOYSA-N 0.000 description 1
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- LJFDXXUKKMEQKE-UHFFFAOYSA-N 2,4-difluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1 LJFDXXUKKMEQKE-UHFFFAOYSA-N 0.000 description 1
- CARZIMSIYVZQDB-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluorobenzonitrile Chemical compound FC1=C(Cl)C(F)=C(C#N)C(F)=C1Cl CARZIMSIYVZQDB-UHFFFAOYSA-N 0.000 description 1
- UPMXOELFJREBOG-UHFFFAOYSA-N 3,5-dichloro-2,6-difluorobenzonitrile Chemical compound FC1=C(Cl)C=C(Cl)C(F)=C1C#N UPMXOELFJREBOG-UHFFFAOYSA-N 0.000 description 1
- QYALCKFGISNFMJ-UHFFFAOYSA-N 3-chloro-2,6-difluorobenzonitrile Chemical compound FC1=CC=C(Cl)C(F)=C1C#N QYALCKFGISNFMJ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11348083A JPS604159A (ja) | 1983-06-23 | 1983-06-23 | フルオロベンゾニトリル系化合物の製造方法 |
| GB08415348A GB2142018B (en) | 1983-06-23 | 1984-06-15 | Method for producing 2,6-difluorobenzonitrile |
| DE19843422936 DE3422936A1 (de) | 1983-06-23 | 1984-06-20 | Verfahren zur herstellung von 2,6-difluorbenzonitril |
| CH303784A CH660361A5 (de) | 1983-06-23 | 1984-06-22 | Verfahren zur herstellung von 2,6-difluorbenzonitril. |
| FR8409817A FR2549048B1 (fr) | 1983-06-23 | 1984-06-22 | Procede de preparation du 2,6-difluorobenzonitrile a partir du 2,6-dichlorobenzonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11348083A JPS604159A (ja) | 1983-06-23 | 1983-06-23 | フルオロベンゾニトリル系化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS604159A JPS604159A (ja) | 1985-01-10 |
| JPH0216746B2 true JPH0216746B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-04-18 |
Family
ID=14613344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11348083A Granted JPS604159A (ja) | 1983-06-23 | 1983-06-23 | フルオロベンゾニトリル系化合物の製造方法 |
Country Status (5)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023358A (ja) * | 1983-07-19 | 1985-02-05 | Ishihara Sangyo Kaisha Ltd | ２，４，６−トリフルオロベンゾニトリル |
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5502235A (en) * | 1994-12-28 | 1996-03-26 | Dowelanco | Solventless process for making 2,6 difluorobenzonitrile |
| US6437168B1 (en) | 2000-09-05 | 2002-08-20 | Nippon Shokubai Co., Ltd. | Method for production of aromatic fluorine compound |
| CN104387289B (zh) * | 2014-10-30 | 2017-09-01 | 天津河清化学工业有限公司 | 二氟苯腈生产中降低催化剂用量的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1026290A (en) * | 1964-03-17 | 1966-04-14 | Robert Neville Haszeldine | Aromatic fluorine compounds |
| US3240824A (en) * | 1965-01-28 | 1966-03-15 | Olin Mathieson | Process for preparing fluoronitrobenzenes |
-
1983
- 1983-06-23 JP JP11348083A patent/JPS604159A/ja active Granted
-
1984
- 1984-06-15 GB GB08415348A patent/GB2142018B/en not_active Expired
- 1984-06-20 DE DE19843422936 patent/DE3422936A1/de active Granted
- 1984-06-22 FR FR8409817A patent/FR2549048B1/fr not_active Expired
- 1984-06-22 CH CH303784A patent/CH660361A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2549048A1 (fr) | 1985-01-18 |
| DE3422936A1 (de) | 1985-01-03 |
| DE3422936C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-11-16 |
| GB2142018A (en) | 1985-01-09 |
| CH660361A5 (de) | 1987-04-15 |
| JPS604159A (ja) | 1985-01-10 |
| FR2549048B1 (fr) | 1987-12-24 |
| GB2142018B (en) | 1986-12-10 |
| GB8415348D0 (en) | 1984-07-18 |