ES2307469T1 - METHOD FOR PREPARING FLUORATED ORGANIC COMPOUNDS. - Google Patents

METHOD FOR PREPARING FLUORATED ORGANIC COMPOUNDS. Download PDF

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Publication number
ES2307469T1
ES2307469T1 ES06844260T ES06844260T ES2307469T1 ES 2307469 T1 ES2307469 T1 ES 2307469T1 ES 06844260 T ES06844260 T ES 06844260T ES 06844260 T ES06844260 T ES 06844260T ES 2307469 T1 ES2307469 T1 ES 2307469T1
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ES
Spain
Prior art keywords
formula
compound
conversion
out under
carried out
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.)
Pending
Application number
ES06844260T
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Spanish (es)
Inventor
Sudip Mukhopadhyay
Hsueh Sung Tung
Haridasan Nair
Michael Van Der Puy
Rajesh Dubey
Robert Johnson
Rajiv R. Singh
Wang Haiyou
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Honeywell International Inc
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Honeywell International Inc
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Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of ES2307469T1 publication Critical patent/ES2307469T1/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/25Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02Materials undergoing a change of physical state when used
    • C09K5/04Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10Components
    • C09K2205/12Hydrocarbons
    • C09K2205/122Halogenated hydrocarbons

Abstract

Un método para preparar compuestos orgánicos fluorados que comprende convertir al menos un compuesto de la primera fórmula siguiente: CF3CH2CHmX3-m a al menos un compuesto de la segunda fórmula siguiente CF3CZ = CHF donde cada X es independientemente Cl, I o Br; y Z es independientemente H o F; y m es 1, 2 ó 3.A method for preparing fluorinated organic compounds comprising converting at least one compound of the first following formula: CF3CH2CHmX3-m to at least one compound of the second following formula CF3CZ = CHF where each X is independently Cl, I or Br; and Z is independently H or F; and m is 1, 2 or 3.

Claims (19)

1. Un método para preparar compuestos orgánicos fluorados que comprende convertir al menos un compuesto de la primera fórmula siguiente:1. A method to prepare organic compounds fluorinated which comprises converting at least one compound of the First following formula: CF_{3}CH_{2}CH_{m}X_{3-m}CF 3 CH 2 CH m X 3-m a al menos un compuesto de la segunda fórmula siguienteto at least one compound of the second formula next CF_{3}CZ=CHFCF 3 CZ = CHF donde cada X es independientemente Cl, I o Br; y Z es independientemente H o F; y m es 1, 2 ó 3.where each X is independently Cl, I or Br; and Z is independently H or F; and m is 1, 2 or 3. 2. El método de la reivindicación 1 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una conversión de al menos un compuesto de acuerdo a la primera fórmula de al menos alrededor de 40%.2. The method of claim 1 wherein said Conversion step is carried out under effective conditions to provide a conversion of at least one compound according to the first formula of at least about 40%. 3. El método de la reivindicación 1 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una conversión de al menos un compuesto de acuerdo a la primera fórmula de al menos alrededor de 80%.3. The method of claim 1 wherein said Conversion step is carried out under effective conditions to provide a conversion of at least one compound according to the first formula of at least about 80%. 4. El método de la reivindicación 1 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una conversión de al menos un compuesto de acuerdo a la primera fórmula de al menos alrededor de 90%.4. The method of claim 1 wherein said Conversion step is carried out under effective conditions to provide a conversion of at least one compound according to the first formula of at least about 90%. 5. El método de la reivindicación 1 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una selectividad a al menos un compuesto de acuerdo a la segunda fórmula de al menos alrededor de 95%.5. The method of claim 1 wherein said Conversion step is carried out under effective conditions to provide a selectivity to at least one compound of according to the second formula of at least about 95%. 6. El método de la reivindicación 1 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una selectividad a al menos un compuesto de acuerdo a la segunda fórmula de al menos alrededor de 90%.6. The method of claim 1 wherein said Conversion step is carried out under effective conditions to provide a selectivity to at least one compound of according to the second formula of at least about 90%. 7. Un método para preparar compuestos orgánicos fluorados que comprende convertir al menos un compuesto de fórmula:7. A method to prepare organic compounds fluorinated which comprises converting at least one compound of formula: (I)CF_{3}[C(R^{1}{}_{a}R^{2}{}_{b})]_{n}C(R^{3}{}_{c}R^{4}{}_{d})(I) CF 3 [C (R 1 {} a} R 2 {} b)] n C (R 3 {} c R 4 {d d) a al menos un compuesto de fórmula (II)to at least one compound of formula (II) (II)CF_{3}[C(R^{1}{}_{a}R^{2}{}_{b})]_{n-1}CZ=CHZ(II) CF 3 [C (R 1 {a} R 2 {b})] n-1 CZ = CHZ donde R^{1}, R^{2}, R^{3} y R^{4} son cada uno independientemente un átomo de hidrógeno o un halógeno seleccionado a partir del grupo que consiste de fluoro, cloro, bromo y yodo, a condición de que al menos uno de R^{1}, R^{2}, R^{3} y R^{4} sea un halógeno; a y b son independientemente igual a 0, 1 ó 2, a condición de que (a+b) = 2; b y c son independientemente igual a 0, 1, 2 ó 3 y (c+d) = 3, n es 1, 2, 3 ó 4, y cada Z es independientemente H o un halógeno, a condición además de que la Z en el carbono terminal sea un halógeno.where R 1, R 2, R 3 and R 4 are each independently a hydrogen atom or a halogen selected from the group consisting of fluoro, chlorine, bromine and iodine, provided that at least one of R1, R 2, R 3 and R 4 is a halogen; a and b are independently equal to 0, 1 or 2, provided that (a + b) = 2; b and c are independently equal to 0, 1, 2 or 3 and (c + d) = 3, n is 1, 2, 3 or 4, and each Z is independently H or a halogen, to condition in addition to the Z in the terminal carbon being a halogen 8. El método de la reivindicación 7 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una conversión de al menos un compuesto de acuerdo a la fórmula (I) de al menos alrededor de 40%.8. The method of claim 7 wherein said Conversion step is carried out under effective conditions to provide a conversion of at least one compound according to the formula (I) of at least about 40%. 9. El método de la reivindicación 7 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una conversión de al menos un compuesto de acuerdo a la fórmula (I) de al menos alrededor de 90%.9. The method of claim 7 wherein said Conversion step is carried out under effective conditions to provide a conversion of at least one compound according to formula (I) of at least about 90%. 10. El método de la reivindicación 7 donde dicho paso de conversión es llevado a cabo bajo condiciones efectivas para proporcionar una selectividad a al menos un compuesto de acuerdo a la fórmula (II) de al menos alrededor de 90%.10. The method of claim 7 wherein said Conversion step is carried out under effective conditions to provide a selectivity to at least one compound of according to formula (II) of at least about 90%. 11. El método de la reivindicación 7 donde la Z en el carbono terminal es fluoro.11. The method of claim 7 wherein the Z In the terminal carbon is fluoro. 12. El método de la reivindicación 13 donde n es 1.12. The method of claim 13 wherein n is one. 13. El método de la reivindicación 14 donde el compuesto de fórmula (II) comprende HFO-1234ze.13. The method of claim 14 wherein the Compound of formula (II) comprises HFO-1234ze. 14. El método de la reivindicación 7 donde el compuesto de fórmula (I) es seleccionado del grupo que consiste de pentacloropropano (HCC-240); tetraclorofluoropropano (HCFC-241); triclorodifluoropropano (HCFC-242); diclorotrifluoropropano (HCFC-243); clorotrifluoropropano (HCFC-244); pentafluoropropano (HFC-245), y todos los isómeros y combinaciones de cada uno de estos.14. The method of claim 7 wherein the compound of formula (I) is selected from the group consisting of pentachloropropane (HCC-240); tetrachlorofluoropropane (HCFC-241); trichlorodifluoropropane (HCFC-242); dichlorotrifluoropropane (HCFC-243); chlorotrifluoropropane (HCFC-244); pentafluoropropane (HFC-245), and all isomers and combinations of each one of these. 15. El método de la reivindicación 7 donde el compuesto de fórmula (I) comprende HCFC-244fa.15. The method of claim 7 wherein the compound of formula (I) comprises HCFC-244fa. 16. El método de la reivindicación 7 donde el compuesto de fórmula (I) comprende HCFC-245fa.16. The method of claim 7 wherein the compound of formula (I) comprises HCFC-245fa. 17. El método de la reivindicación 7 donde dicho paso de conversión comprende convertir catalíticamente el compuesto de fórmula (I) a uno o más compuestos de fórmula (II).17. The method of claim 7 wherein said Conversion step comprises catalytically converting the compound of formula (I) to one or more compounds of formula (II). 18. El método de la reivindicación 17 donde dicho paso de convertir catalíticamente el compuesto de fórmula (I) comprende exponer dicho compuesto de fórmula (I) a un catalizador de metal de carga neutral.18. The method of claim 17 wherein said step of catalytically converting the compound of formula (I) comprises exposing said compound of formula (I) to a catalyst of neutral charge metal. 19. El método de la reivindicación 17 donde dicho paso de convertir catalíticamente el compuesto de fórmula (I) comprende exponer dicho compuesto de fórmula (I) a un catalizador de Ni^{0}.19. The method of claim 17 wherein said step of catalytically converting the compound of formula (I) comprises exposing said compound of formula (I) to a catalyst of Ni 0.
ES06844260T 2005-11-03 2006-11-03 METHOD FOR PREPARING FLUORATED ORGANIC COMPOUNDS. Pending ES2307469T1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US73337705P 2005-11-03 2005-11-03
US733377P 2005-11-03
US76308606P 2006-01-27 2006-01-27
US763086P 2006-01-27

Publications (1)

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ES2307469T1 true ES2307469T1 (en) 2008-12-01

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ES06844260T Pending ES2307469T1 (en) 2005-11-03 2006-11-03 METHOD FOR PREPARING FLUORATED ORGANIC COMPOUNDS.

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EP (1) EP1954663A1 (en)
JP (2) JP5270361B2 (en)
KR (1) KR20080066853A (en)
DE (1) DE06844260T1 (en)
ES (1) ES2307469T1 (en)
WO (1) WO2007056149A1 (en)

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KR20080066853A (en) * 2005-11-03 2008-07-16 허니웰 인터내셔널 인코포레이티드 Method for producing fluorinated organic compounds
US9040759B2 (en) * 2007-07-06 2015-05-26 Honeywell International Inc. Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons
JP5277813B2 (en) * 2008-09-11 2013-08-28 セントラル硝子株式会社 Method for producing fluorinated propene
US8829254B2 (en) * 2012-02-14 2014-09-09 Honeywell International Inc. Process for making 1,3,3,3-tetrafluoropropene
US9187386B2 (en) * 2013-05-23 2015-11-17 The Chemours Company Fc, Llc Catalytic process of making 1,3,3,3-tetrafluoropropene
GB2528690B (en) * 2014-07-28 2017-03-01 Mexichem Amanco Holding Sa Process for preparing a (hydro)(chloro)fluoroalkene

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JP5715177B2 (en) 2015-05-07
JP2013151532A (en) 2013-08-08
JP5270361B2 (en) 2013-08-21
WO2007056149A1 (en) 2007-05-18
JP2009514956A (en) 2009-04-09
DE06844260T1 (en) 2008-12-24
EP1954663A1 (en) 2008-08-13
KR20080066853A (en) 2008-07-16

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