DE2902877C2 - Verfahren zur Herstellung eines Fluorbenzomononitrils - Google Patents
Verfahren zur Herstellung eines FluorbenzomononitrilsInfo
- Publication number
- DE2902877C2 DE2902877C2 DE2902877A DE2902877A DE2902877C2 DE 2902877 C2 DE2902877 C2 DE 2902877C2 DE 2902877 A DE2902877 A DE 2902877A DE 2902877 A DE2902877 A DE 2902877A DE 2902877 C2 DE2902877 C2 DE 2902877C2
- Authority
- DE
- Germany
- Prior art keywords
- sulfolane
- mol
- boiling point
- hours
- fluorobenzonitrile
- 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
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 9
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 10
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 7
- 239000011698 potassium fluoride Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 235000003270 potassium fluoride Nutrition 0.000 description 5
- 238000001256 steam distillation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 description 4
- XPTAYRHLHAFUOS-UHFFFAOYSA-N 2-chloro-6-fluorobenzonitrile Chemical compound FC1=CC=CC(Cl)=C1C#N XPTAYRHLHAFUOS-UHFFFAOYSA-N 0.000 description 4
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 2
- 150000008359 benzonitriles Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CHKLNKWJIDQKFV-UHFFFAOYSA-N 3-chloro-2-fluorobenzonitrile Chemical compound FC1=C(Cl)C=CC=C1C#N CHKLNKWJIDQKFV-UHFFFAOYSA-N 0.000 description 1
- 101100026210 Drosophila melanogaster Clbn gene Proteins 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960004273 floxacillin Drugs 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 1
- 229960003528 flurazepam Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB357678 | 1978-01-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2902877A1 DE2902877A1 (de) | 1979-08-23 |
| DE2902877C2 true DE2902877C2 (de) | 1983-05-05 |
Family
ID=9760949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2902877A Expired DE2902877C2 (de) | 1978-01-28 | 1979-01-25 | Verfahren zur Herstellung eines Fluorbenzomononitrils |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4209457A (en, 2012) |
| DE (1) | DE2902877C2 (en, 2012) |
| FR (1) | FR2415626A1 (en, 2012) |
| NL (1) | NL7900615A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073372B1 (en) * | 1981-08-31 | 1984-08-01 | Ishihara Sangyo Kaisha, Ltd. | Process for producing 2,6-difluorobenzonitrile |
| DE3478681D1 (en) * | 1983-02-18 | 1989-07-20 | Nippon Catalytic Chem Ind | Organic fluorine compounds |
| JPS6094919A (ja) * | 1983-10-31 | 1985-05-28 | Nippon Shokubai Kagaku Kogyo Co Ltd | 有機フツ素化物の製法 |
| US4952719A (en) * | 1984-10-15 | 1990-08-28 | Occidental Chemical Corporation | Process for the preparation of halo aromatic compounds |
| US5214187A (en) * | 1988-06-21 | 1993-05-25 | Basf Aktiengesellschaft | Benzonitriles, benzaldehydes and benzyl alcohols |
| US5153350A (en) * | 1991-05-16 | 1992-10-06 | Braish Tamim F | Process for preparing 3,4,6-trifluorophithalonitrile |
| DE59401358D1 (de) * | 1993-01-23 | 1997-02-06 | Hoechst Ag | 2,3-Difluor-6-nitrobenzonitril und 2-Chlor-5,6-difluorbenzonitril, Verfahren zu deren Herstellung und ihre Verwendung zur Herstellung von 2,3,6-Trifluorbenzoesäure |
| US5502235A (en) * | 1994-12-28 | 1996-03-26 | Dowelanco | Solventless process for making 2,6 difluorobenzonitrile |
| US5824827A (en) * | 1996-11-22 | 1998-10-20 | Albemarle Corporation | Halogen exchange reactions |
| DE69711220T2 (de) | 1996-11-22 | 2002-10-31 | Albemarle Corp., Baton Rouge | Halogenaustausch-reaktionen und ihre anwendungen |
| US5789631A (en) * | 1996-11-25 | 1998-08-04 | Albemarle Corporation | Production of perhalobenzenes |
| US5965781A (en) * | 1997-11-21 | 1999-10-12 | Albemarle Corporation | Catalysis in halogen exchange reactions |
| CN1097482C (zh) * | 2000-12-25 | 2003-01-01 | 化学工业部天津化工研究设计院 | 一种邻(对)甲基苯腈催化剂的制备方法 |
| CN100427462C (zh) * | 2006-11-27 | 2008-10-22 | 浙江大学 | 2,4-二氟苯腈的制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1359410A (fr) * | 1962-04-04 | 1964-04-24 | Nat Smelting Co Ltd | Procédé de préparation de nitriles aromatiques fluorés |
| NL129620C (en, 2012) * | 1963-04-01 | |||
| GB1026290A (en) * | 1964-03-17 | 1966-04-14 | Robert Neville Haszeldine | Aromatic fluorine compounds |
| GB1259173A (en, 2012) * | 1968-03-28 | 1972-01-05 | ||
| JPS516940A (en, 2012) * | 1974-07-04 | 1976-01-20 | Kogyo Gijutsuin |
-
1979
- 1979-01-25 DE DE2902877A patent/DE2902877C2/de not_active Expired
- 1979-01-26 NL NL7900615A patent/NL7900615A/xx not_active Application Discontinuation
- 1979-01-26 FR FR7902108A patent/FR2415626A1/fr active Granted
- 1979-01-29 US US06/007,596 patent/US4209457A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4209457A (en) | 1980-06-24 |
| FR2415626B1 (en, 2012) | 1983-08-12 |
| NL7900615A (nl) | 1979-07-31 |
| DE2902877A1 (de) | 1979-08-23 |
| FR2415626A1 (fr) | 1979-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAR | Request for search filed | ||
| OB | Request for examination as to novelty | ||
| OC | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |