EP3408248A1 - Verfahren zur herstellung von 2-chlor-3,3,3-trifluorpropen - Google Patents

Verfahren zur herstellung von 2-chlor-3,3,3-trifluorpropen

Info

Publication number
EP3408248A1
EP3408248A1 EP17706527.3A EP17706527A EP3408248A1 EP 3408248 A1 EP3408248 A1 EP 3408248A1 EP 17706527 A EP17706527 A EP 17706527A EP 3408248 A1 EP3408248 A1 EP 3408248A1
Authority
EP
European Patent Office
Prior art keywords
hcfo
trifluoropropene
chloro
stream
hcfc
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.)
Withdrawn
Application number
EP17706527.3A
Other languages
English (en)
French (fr)
Inventor
Dominique Deur-Bert
Dominique Garrait
Anne Pigamo
Laurent Wendlinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema France SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP3408248A1 publication Critical patent/EP3408248A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206—Preparation 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

Definitions

  • HFO-1234yf 2,3,3,3-Tetrafluoropropene (HFO-1234yf), because of its low Global Warming Potential warming potential, is considered a potential candidate for replacing HFC-134a in automotive air conditioning.
  • stream B also comprises dichlorodifluoropropene (HCFO-1232).
  • dichlorodifluoropropene includes the isomers of dichlorodifluoropropene such as 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf), 2,3-dichloro-1,1-difluoropropene (HCFO-1232xc), 1,2-dichlorodifluoropropene. dichloro-1,3-difluoropropene (HCFO-1232xb).
  • stream B also comprises 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf).
  • the contacting is carried out at a temperature between 225 and 450 ° C, in particular between 250 and 400 ° C.
  • the present invention further provides a process for producing 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) by contacting 2,3-dichloro-1,1,1 trifluoropropane (HCFC-243db), with gaseous phase IHF in the presence of an AIF3 catalyst or fluorinated alumina to form a stream B comprising 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf); advantageously to form a stream B comprising 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and 3,3,3-trifluoropropene (1243zf); preferably to form a stream B comprising 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 3,3,3-trifluoropropene (HFO-1243zf), trichlorofluoropropene (HCFO-1231); in particular to form a stream B
  • the resulting stream B can be purified to isolate a stream comprising HCFO-1233xf or be used in a process for producing 2,3,3,3-tetrafluoropropene (HFO-1234yf).
  • the method according to the present invention can be implemented continuously or discontinuously.
  • the liquid phase C can also comprise 2,3,3-chloro-3-fluoro-propene (HCFO-1231xf), 1,2,3-trichloro-1-fluoropropene (Z / E-HCFO-1231xb) or 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf).
  • the gaseous stream D may comprise 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 3,3,3-trifluoropropene (HFO-1243zf), trichlorofluoropropene (HCFO-1231), dichlorodifluoropropene (HCFO - 1232).
  • the fluorination reactor is loaded with a type AIF3 catalyst bed.
  • the fluorination reaction of HCC-240db is carried out at a temperature between 275 and 375 ° C at an absolute pressure of 1 bar.
  • a series of four tests were performed according to the conditions listed in Table 1 below.
  • the gas phase is analyzed by GC and GC-MS.
  • the compounds identified in the gas phase for Examples 1 to 4 are detailed in Table 3 below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
EP17706527.3A 2016-01-28 2017-01-13 Verfahren zur herstellung von 2-chlor-3,3,3-trifluorpropen Withdrawn EP3408248A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1650673A FR3047240B1 (fr) 2016-01-28 2016-01-28 Procede de fabrication du 2-chloro-3,3,3-trifluoropropene
PCT/FR2017/050079 WO2017129878A1 (fr) 2016-01-28 2017-01-13 Procede de fabrication du 2-chloro-3,3,3-trifluoropropene

Publications (1)

Publication Number Publication Date
EP3408248A1 true EP3408248A1 (de) 2018-12-05

Family

ID=55590059

Family Applications (1)

Application Number Title Priority Date Filing Date
EP17706527.3A Withdrawn EP3408248A1 (de) 2016-01-28 2017-01-13 Verfahren zur herstellung von 2-chlor-3,3,3-trifluorpropen

Country Status (6)

Country Link
US (1) US10487028B2 (de)
EP (1) EP3408248A1 (de)
JP (1) JP6832940B2 (de)
CN (1) CN108473395A (de)
FR (1) FR3047240B1 (de)
WO (1) WO2017129878A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7151257B2 (ja) * 2018-08-07 2022-10-12 Ａｇｃ株式会社 ２－クロロ－３，３－ジフルオロプロペンの製造方法、２－クロロ－１，１，２－トリフルオロプロパンの製造方法、２，３，３－トリフルオロプロペンの製造方法、１，２－ジクロロ－２，３，３－トリフルオロプロパンの製造方法、１－クロロ－２，３，３－トリフルオロプロペンの製造方法
AU2020287313A1 (en) * 2019-06-04 2021-12-02 The Chemours Company Fc, Llc 2-chloro-3,3,3-trifluoropropene (1233XF) compositions and methods for making and using the compositions
CN112452345B (zh) * 2020-11-17 2023-03-21 西安近代化学研究所 气相氟化合成反式-1-氯-3,3,3-三氟丙烯用催化剂及合成方法
CN115572208A (zh) * 2022-08-29 2023-01-06 西安近代化学研究所 一种2-氯-3,3,3-三氟丙烯的制备方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS572695B2 (de) * 1973-04-26 1982-01-18
JP3516324B2 (ja) * 1996-08-23 2004-04-05 セントラル硝子株式会社 １−クロロ−３，３，３−トリフルオロプロペンの製造法
CN101351426B (zh) * 2005-11-03 2013-05-08 霍尼韦尔国际公司 氟化有机化合物的制备方法
US7795480B2 (en) * 2007-07-25 2010-09-14 Honeywell International Inc. Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf)
CN102405202B (zh) * 2009-04-23 2015-02-11 大金工业株式会社 制备2-氯-3,3,3-三氟丙烯的方法
US8614361B2 (en) 2009-04-23 2013-12-24 Daikin Industries, Ltd. Process for preparation of 2,3,3,3-tetrafluoropropene
US8779219B2 (en) * 2009-05-13 2014-07-15 Daikin Industries, Ltd. Process for preparing chlorine-containing fluorocarbon compound
ES2770405T3 (es) * 2010-10-22 2020-07-01 Arkema France Proceso para la fabricación de 2-cloro-3,3,3-trifluropropeno por fluoración en fase gaseosa de pentacloropropano
CN104284874A (zh) * 2011-11-04 2015-01-14 汪海有 用于产生2,3,3,3-四氟丙烯的方法
CN102442881B (zh) * 2011-11-25 2014-07-16 西安近代化学研究所 2-氯-3,3,3-三氟丙烯的制备方法
CN102614901B (zh) * 2012-03-08 2014-02-05 浙江三美化工股份有限公司 由1,1,2,3-四氯丙烯合成2-氯-3,3,3-三氟丙烯的催化剂及其制备方法
US9422211B2 (en) * 2012-08-08 2016-08-23 Daikin Industries, Ltd. Process for producing 2,3,3,3-tetrafluoropropene

Also Published As

Publication number Publication date
US10487028B2 (en) 2019-11-26
WO2017129878A1 (fr) 2017-08-03
JP6832940B2 (ja) 2021-02-24
CN108473395A (zh) 2018-08-31
US20190031584A1 (en) 2019-01-31
JP2019504841A (ja) 2019-02-21
FR3047240B1 (fr) 2019-09-27
FR3047240A1 (fr) 2017-08-04

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