DK2440518T3 - Fremgangsmåde til fremstilling af fluoralkylnitriler - Google Patents

Fremgangsmåde til fremstilling af fluoralkylnitriler Download PDF

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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
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DK
Denmark
Prior art keywords
acid
alkyl
chlorine
process according
aryl
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DK10722625.0T
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English (en)
Inventor
Norbert Lui
Jens-Dietmar Heinrich
Thomas Wollner
Sergii Pazenok
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Bayer Cropscience Ag
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Publication of DK2440518T3 publication Critical patent/DK2440518T3/da

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    • 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

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  • 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.
DK10722625.0T 2009-06-08 2010-05-26 Fremgangsmåde til fremstilling af fluoralkylnitriler DK2440518T3 (da)

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

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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)

* Cited by examiner, † Cited by third party
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
EP3490972B1 (de) 2016-07-28 2020-09-23 Bayer CropScience Aktiengesellschaft Verfahren zur herstellung von fluoralkylnitrilen und den entsprechenden fluoralkyltetrazolen
DK3589612T3 (da) * 2017-02-28 2021-06-21 Bayer Cropscience Ag Fremgangsmåde til fremstilling af fluoralkylnitriler og de tilsvarende fluoralkyltetrazoler
IL280732B2 (en) 2018-09-03 2024-04-01 Pi Industries Ltd A method for the preparation of fluoroalkyl nitrates and their use for the preparation of fluoroalkaline tetrazoles

Family Cites Families (13)

* Cited by examiner, † Cited by third party
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
US20070293515A1 (en) * 2004-08-03 2007-12-20 Layton Mark E 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

Also Published As

Publication number Publication date
CN102459157A (zh) 2012-05-16
WO2010142377A1 (de) 2010-12-16
CN102459157B (zh) 2014-09-10
US20100312002A1 (en) 2010-12-09
BRPI1010841A2 (pt) 2016-04-05
EP2440518A1 (de) 2012-04-18
KR101705287B1 (ko) 2017-02-09
IL216694A0 (en) 2012-02-29
MX2011013146A (es) 2012-01-20
TWI471294B (zh) 2015-02-01
US8203015B2 (en) 2012-06-19
TW201119982A (en) 2011-06-16
EP2440518B1 (de) 2014-08-20
IL216694A (en) 2015-02-26
ES2518465T3 (es) 2014-11-05
KR20120032518A (ko) 2012-04-05
JP5571779B2 (ja) 2014-08-13
JP2012529446A (ja) 2012-11-22

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