ES2329867T1 - Procedimiento integrado para producir 2,3,3,3-tetrafluoropropano. - Google Patents

Procedimiento integrado para producir 2,3,3,3-tetrafluoropropano. Download PDF

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Publication number
ES2329867T1
ES2329867T1 ES09155292T ES09155292T ES2329867T1 ES 2329867 T1 ES2329867 T1 ES 2329867T1 ES 09155292 T ES09155292 T ES 09155292T ES 09155292 T ES09155292 T ES 09155292T ES 2329867 T1 ES2329867 T1 ES 2329867T1
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Prior art keywords
chloro
tetrafluoropropane
formula
stage
produce
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ES2329867T5 (es
ES2329867T3 (es
Inventor
Daniel C. Merkel
Hsueh Sung Tung
Konstantin A. Pokrovski
Selma Bektesevic
Robert C. Johnson
Haiyou Wang
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Honeywell International Inc
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Honeywell International Inc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/013Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/04Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00Halogens; Halogen acids
    • C01B7/01Chlorine; Hydrogen chloride
    • C01B7/03Preparation from chlorides
    • C01B7/035Preparation of hydrogen chloride from chlorides
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00Halogens; Halogen acids
    • C01B7/01Chlorine; Hydrogen chloride
    • C01B7/07Purification ; Separation
    • C01B7/0706Purification ; Separation of hydrogen chloride
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00Halogens; Halogen acids
    • C01B7/19Fluorine; Hydrogen fluoride
    • C01B7/191Hydrogen fluoride
    • C01B7/195Separation; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/07Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/087Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
    • 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
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/383Separation; Purification; Stabilisation; Use of additives by distillation
    • 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/10Process efficiency
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Un método para preparar 2,3,3,3-tetrafluoroprop-1-eno, que comprende: a. proporcionar una composición de partida que comprende al menos un compuesto que tiene una estructura seleccionada de las Fórmulas I, II y III: CX2=CCl-CH2X (Fórmula I) CX3-CCl=CH2 (Fórmula II) CX 3-CHCl-CH 2X (Fórmula III) en las que X se selecciona independientemente de F, Cl, Br y I, con la condición de que al menos un X no sea flúor; b. poner en contacto dicha composición de partida con un primer agente fluorante para producir una primera composición intermedia que comprende 2-cloro-3,3,3-trifluoropropeno y un primer subproducto que contiene cloro; c. poner en contacto dicha primera composición intermedia con un segundo agente fluorante para producir una segunda composición intermedia que comprende 2-cloro-1,1,1,2-tetrafluoropropano; y d. deshidroclorar al menos una porción de dicho 2-cloro-1,1,1,2-tetrafluoropropano para producir un producto de reacción que comprende 2,3,3,3-tetrafluoroprop-1-eno y un segundo subproducto que contiene cloro.

Claims (10)

1. Un método para preparar 2,3,3,3-tetrafluoroprop-1-eno, que comprende:
a.
proporcionar una composición de partida que comprende al menos un compuesto que tiene una estructura seleccionada de las Fórmulas I, II y III:
(Fórmula I)CX_{2}=CCl-CH_{2}X
(Fórmula II)CX_{3}-CCl=CH_{2}
(Fórmula III)CX_{3}-CHCl-CH_{2}X
en las que X se selecciona independientemente de F, Cl, Br y I, con la condición de que al menos un X no sea flúor;
b.
poner en contacto dicha composición de partida con un primer agente fluorante para producir una primera composición intermedia que comprende 2-cloro-3,3,3-trifluoropropeno y un primer subproducto que contiene cloro;
c.
poner en contacto dicha primera composición intermedia con un segundo agente fluorante para producir una segunda composición intermedia que comprende 2-cloro-1,1,1,2-tetrafluoropropano; y
d.
deshidroclorar al menos una porción de dicho 2-cloro-1,1,1,2-tetrafluoropropano para producir un producto de reacción que comprende 2,3,3,3-tetrafluoroprop-1-eno y un segundo subproducto que contiene cloro.
2. El método de la reivindicación 1, que comprende además la etapa de eliminar al menos una porción de dicho primer subproducto que contiene cloro de dicha primera composición intermedia, subsiguiente a, y/o concurrentemente con, dicha etapa (b) de puesta en contacto, y la etapa de eliminar al menos una porción de dicho segundo subproducto que contiene cloro de dicho producto, subsiguiente a, y/o concurrentemente con, dicha etapa (d).
3. El método de la reivindicación 1, en el que dicho compuesto según la Fórmula I es 1,1,2,3-tetracloropropeno.
4. El método de la reivindicación 1, en el que dicho compuesto según la Fórmula II es 2,3,3,3-tetracloropropeno.
5. El método de la reivindicación 1, en el que dicho compuesto según la Fórmula III es 1,1,1,2,3-pentacloropropano.
6. El método de la reivindicación 1, en el que dicha etapa (b) de puesto en contacto comprende una fluoración catalítica en fase de vapor de dicho compuesto que tiene una estructura según las Fórmulas I, II o III.
7. El método de la reivindicación 1, en el que dicha etapa (c) de puesta en contacto comprende una fluoración en fase líquida de dicho 2-cloro-3,3,3-trifluoropropeno en presencia de un catalizador.
8. El método de la reivindicación 1, en el que dicha deshidrocloración se lleva a cabo en fase de vapor y en presencia de un catalizador.
9. El método de la reivindicación 1, en el que dichos primer y segundo agentes de fluoración son fluoruro de hidrógeno, comprendiendo además dicho método la etapa de separar al menos una porción de dicho fluoruro de hidrógeno de dicho 2-cloro-3,3,3-trifluoropropeno subsiguiente a, o concurrentemente con, la etapa (b) y antes de la etapa (c), y la etapa de separar al menos una porción de dicho fluoruro de hidrógeno de dicho 2-cloro-1,1,1,2-tetrafluoropropano subsiguiente a, o concurrentemente con, la etapa (c) o antes de la etapa (d).
10. El método de la reivindicación 9, en el que dicho primer agente fluorante comprende al menos una porción de dicho fluoruro de hidrógeno separada de dicho 2-cloro-3,3,3-trifluoropropeno, y dicho segundo agente fluorante comprende al menos una porción de dicho fluoruro de hidrógeno separada de dicho 2-cloro-1,1,1,2-tetrafluoropropano.
ES09155292T 2008-03-20 2009-03-16 Procedimiento integrado para producir 2,3,3,3-tetrafluoropropeno Active ES2329867T5 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US3832708P 2008-03-20 2008-03-20
US38327P 2008-03-20
US12/404,130 US8058486B2 (en) 2004-04-29 2009-03-13 Integrated process to produce 2,3,3,3-tetrafluoropropene
US404130 2009-03-13

Publications (3)

Publication Number Publication Date
ES2329867T1 true ES2329867T1 (es) 2009-12-02
ES2329867T3 ES2329867T3 (es) 2013-05-24
ES2329867T5 ES2329867T5 (es) 2022-04-29

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US (1) US8058486B2 (es)
EP (3) EP3722273A1 (es)
JP (4) JP5571903B2 (es)
KR (1) KR101594022B1 (es)
CN (2) CN105001041A (es)
DE (1) DE09155292T1 (es)
ES (2) ES2798771T3 (es)
MX (1) MX2009002967A (es)
PL (1) PL2583959T3 (es)
PT (1) PT2583959T (es)

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