DK2440518T3 - Fremgangsmåde til fremstilling af fluoralkylnitriler - Google Patents
Fremgangsmåde til fremstilling af fluoralkylnitriler Download PDFInfo
- Publication number
- DK2440518T3 DK2440518T3 DK10722625.0T DK10722625T DK2440518T3 DK 2440518 T3 DK2440518 T3 DK 2440518T3 DK 10722625 T DK10722625 T DK 10722625T DK 2440518 T3 DK2440518 T3 DK 2440518T3
- Authority
- DK
- Denmark
- Prior art keywords
- acid
- alkyl
- chlorine
- process according
- aryl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/10—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and halogen atoms, or nitro or nitroso groups, bound to the same acyclic carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (10)
1. Fremgangsmåde til fremstilling af fluoralkylnitriler med den almene formel (I),
ro hvor X1 og X2 uafhængigt af hinanden står for fluor, chlor, brom, hydrogen, Ci_i2-alkyl, Ci_i2-halogenalkyl, C5_i8-aryl, C7-19-alkylaryl eller C7_i9-arylalkyl, kendetegnet ved, at man omsætter fluorerede carboxylsyreamider med formel (II)
(Π), hvor X1 og X2 har de ovenfor nævnte betegnelser, i nærvær af en base og katalytiske mængder af en floureret carboxylsyre med formel (III),
(ΠΙ), hvor Y1 og Y2 uafhængigt af hinanden står for fluor, chlor, brom, hydrogen, Ci-i2-alkyl, Ci-i2-halogenalkyl, Cs-is-aryl, C7-19-alkylaryl eller C7-ig-arylalkyl, med et syrehalogenid med formel (IV)
(IV), hvor R1 står for Ci-i2-alkyl, C3-8-cycloalkyl, Ci_i2-halogenalkyl, Cs-is-aryl, C7-ig-arylalkyl eller C7-ig-alkylaryl, og Hal står for halogen.
2. Fremgangsmåde ifølge krav 1, idet X1 og X2 uafhængigt af hinanden står for fluor, chlor, hydrogen, Ci_i2-alkyl, Ci_i2-halogenalkyl eller Cs-is-aryl, Y1 og Υ2 uafhængigt af hinanden står for hydrogen, fluor, chlor, C2-8-alkyl eller C2-8_halogenalkyl, Hal står for chlor eller brom; R1 står for C2-8~alkyl eller Cs-ie-aryl.
3. Fremgangsmåde ifølge krav 1 eller 2, idet X1 og X2 uafhængigt af hinanden står for fluor, chlor, hydrogen eller Ci-i2-halogenal kyl, Y1 og Y2 uafhængigt af hinanden står for fluor, chlor, hydrogen, C3-6_alkyl, CF3 eller CF2H, R1 står for C3-6_alkyl eller C6-aryl, og Hal står for chlor.
4. Fremgangsmåde ifølge et af kravene 1 til 3, idet de fluorerede carboxylsyrer er udvalgt af gruppen bestående af trifluoreddikesyre, difluoreddikesyre, difluorchloreddikesyre, chlorfluoreddikesyre, 2,3,3,3-tetrafluorpropionsyre, 2,2,3,3-tetrafluorpropionsyre, 2,2-difluorpropionsyre, pentafluorpropionsyre, 2,3,3,4,4,4-hexafluorbutancarboxylsyre.
5. Fremgangsmåde ifølge et af kravene 1 til 4, idet syrehalogeniderne er udvalgt af gruppen bestående af eddikesyrechlorid, pivalinsyrechlorid, 2,2- dimethylsmørsyrechlorid, isovaleroylchlorid, benzoylchlorid.
6. Fremgangsmåde ifølge et af kravene 1 til 5, idet det molære forhold mellem fluorerede carboxylsyrer med den almene formel (III) og det anvendte fluorerede alkylamid med den almene formel (II) er 0,05 til 1.
7. Fremgangsmåde ifølge et af kravene 1 til 6, idet det molære forhold mellem syrehalegonider med den almene formel (IV) og det anvendte fluorerede alkylamid med den almene formel (II) er 0,5 til 5.
8. Fremgangsmåde ifølge et af kravene 1 bis 7, idet basen er udvalgt af gruppen bestående af pyridin, 3-, 4-picolin, guinolin, guinaldin, halogenerede pyridiner.
9.
Fremgangsmåde ifølge et af kravene 1 til 8, idet det molære forhold mellem base og den anvendte fluorerede carboxylsyre med den almene formel (III) er 0,5 til 10.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09162172 | 2009-06-08 | ||
| PCT/EP2010/003209 WO2010142377A1 (de) | 2009-06-08 | 2010-05-26 | Verfahren zur herstellung von fluoralkylnitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2440518T3 true DK2440518T3 (da) | 2014-11-24 |
Family
ID=41226687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10722625.0T DK2440518T3 (da) | 2009-06-08 | 2010-05-26 | Fremgangsmåde til fremstilling af fluoralkylnitriler |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8203015B2 (da) |
| EP (1) | EP2440518B1 (da) |
| JP (1) | JP5571779B2 (da) |
| KR (1) | KR101705287B1 (da) |
| CN (1) | CN102459157B (da) |
| BR (1) | BRPI1010841A2 (da) |
| DK (1) | DK2440518T3 (da) |
| ES (1) | ES2518465T3 (da) |
| IL (1) | IL216694A (da) |
| MX (1) | MX2011013146A (da) |
| TW (1) | TWI471294B (da) |
| WO (1) | WO2010142377A1 (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2972452B1 (fr) * | 2011-03-09 | 2013-03-15 | Rhodia Operations | Procede de preparation du difluoroacetonitrile et de ses derives |
| FR2975990B1 (fr) * | 2011-06-01 | 2013-05-24 | Rhodia Operations | Procede de preparation d'un compose organique fluore |
| CN103804231A (zh) * | 2014-02-27 | 2014-05-21 | 江苏省激素研究所股份有限公司 | 一种农药中间体三氟乙腈的合成方法 |
| JP6968868B2 (ja) * | 2016-07-28 | 2021-11-17 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | フルオロアルキルニトリルおよび対応するフルオロアルキルテトラゾールの製造方法 |
| DK3589612T3 (da) * | 2017-02-28 | 2021-06-21 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af fluoralkylnitriler og de tilsvarende fluoralkyltetrazoler |
| EP3847155A1 (en) | 2018-09-03 | 2021-07-14 | PI Industries Ltd. | A method for the preparation of fluoroalkyl nitriles and their use to prepare related fluoroalkyl tetrazoles |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2730543A (en) * | 1950-05-20 | 1956-01-10 | Minnesota Mining & Mfg | Fluorinated nitriles |
| US2939878A (en) | 1958-10-22 | 1960-06-07 | Dow Chemical Co | Preparation of fluoronitriles |
| US3928274A (en) * | 1973-08-29 | 1975-12-23 | Lilly Industries Ltd | Process for preparing nitriles |
| FR2501063A1 (fr) | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | Catalyseurs de fluoruration en phase gazeuse des derives chlores aliphatiques, a base de charbon actif impregne de sulfate de chrome, et procedes de fluoruration utilisant ces catalyseurs |
| JPS59118751A (ja) * | 1982-12-24 | 1984-07-09 | Daikin Ind Ltd | フルオロアルキルニトリルの製法 |
| JPS63290843A (ja) * | 1987-05-25 | 1988-11-28 | Ihara Nikkei Kagaku Kogyo Kk | 芳香族ニトリルと芳香族カルボン酸とを製造する方法 |
| JP3471831B2 (ja) * | 1991-12-09 | 2003-12-02 | 富山化学工業株式会社 | 新規なトリアゾール誘導体およびその塩 |
| US5637748A (en) * | 1995-03-01 | 1997-06-10 | E. I. Du Pont De Nemours And Company | Process for synthesizing fluorinated nitrile compounds |
| DE10212526A1 (de) | 2002-03-21 | 2003-10-02 | Solvay Fluor & Derivate | Herstellung von verfestigten organischen Verbindungen, insbesondere von Carbonsäureamiden |
| DE102004003953A1 (de) * | 2004-01-26 | 2005-08-11 | Clariant Gmbh | Verfahren zur Herstellung von Nitrilen und Isonitrilen durch Dehydratisierungsreaktionen mit Propanphosphonsäureanhydriden |
| AU2005271669A1 (en) * | 2004-08-03 | 2006-02-16 | Merck & Co., Inc. | 1,3-disubstituted heteroaryl NMDA/NR2B antagonists |
| RU2440975C2 (ru) * | 2007-06-25 | 2012-01-27 | Дайкин Индастриз, Лтд. | Способ получения фторамида и фторнитрила |
| JP2009114127A (ja) * | 2007-11-07 | 2009-05-28 | Kyorin Pharmaceut Co Ltd | アミノアセチルピロリジンカルボニトリル誘導体の製造方法 |
-
2010
- 2010-05-26 JP JP2012514369A patent/JP5571779B2/ja not_active Expired - Fee Related
- 2010-05-26 BR BRPI1010841A patent/BRPI1010841A2/pt active Search and Examination
- 2010-05-26 KR KR1020127000501A patent/KR101705287B1/ko active IP Right Grant
- 2010-05-26 DK DK10722625.0T patent/DK2440518T3/da active
- 2010-05-26 ES ES10722625.0T patent/ES2518465T3/es active Active
- 2010-05-26 EP EP10722625.0A patent/EP2440518B1/de active Active
- 2010-05-26 MX MX2011013146A patent/MX2011013146A/es active IP Right Grant
- 2010-05-26 CN CN201080025238.XA patent/CN102459157B/zh active Active
- 2010-05-26 WO PCT/EP2010/003209 patent/WO2010142377A1/de active Application Filing
- 2010-06-07 US US12/795,168 patent/US8203015B2/en active Active
- 2010-06-07 TW TW99118295A patent/TWI471294B/zh not_active IP Right Cessation
-
2011
- 2011-11-30 IL IL216694A patent/IL216694A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX2011013146A (es) | 2012-01-20 |
| IL216694A0 (en) | 2012-02-29 |
| US20100312002A1 (en) | 2010-12-09 |
| EP2440518B1 (de) | 2014-08-20 |
| JP5571779B2 (ja) | 2014-08-13 |
| ES2518465T3 (es) | 2014-11-05 |
| CN102459157A (zh) | 2012-05-16 |
| TW201119982A (en) | 2011-06-16 |
| KR101705287B1 (ko) | 2017-02-09 |
| KR20120032518A (ko) | 2012-04-05 |
| BRPI1010841A2 (pt) | 2016-04-05 |
| TWI471294B (zh) | 2015-02-01 |
| US8203015B2 (en) | 2012-06-19 |
| JP2012529446A (ja) | 2012-11-22 |
| WO2010142377A1 (de) | 2010-12-16 |
| EP2440518A1 (de) | 2012-04-18 |
| IL216694A (en) | 2015-02-26 |
| CN102459157B (zh) | 2014-09-10 |
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