EP3408248A1 - Procede de fabrication du 2-chloro-3,3,3-trifluoropropene - Google Patents
Procede de fabrication du 2-chloro-3,3,3-trifluoropropeneInfo
- 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- Withdrawn
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)
Abstract
Description
Claims
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 (fr) | 2018-12-05 |
Family
ID=55590059
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP17706527.3A Withdrawn EP3408248A1 (fr) | 2016-01-28 | 2017-01-13 | Procede de fabrication du 2-chloro-3,3,3-trifluoropropene |
Country Status (6)
Country | Link |
---|---|
US (1) | US10487028B2 (fr) |
EP (1) | EP3408248A1 (fr) |
JP (1) | JP6832940B2 (fr) |
CN (1) | CN108473395A (fr) |
FR (1) | FR3047240B1 (fr) |
WO (1) | WO2017129878A1 (fr) |
Families Citing this family (4)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS572695B2 (fr) * | 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 |
EP2336102A1 (fr) * | 2005-11-03 | 2011-06-22 | Honeywell International Inc. | Procédé de production de composés organiques fluorés |
US7795480B2 (en) * | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
KR101374000B1 (ko) | 2009-04-23 | 2014-03-12 | 다이킨 고교 가부시키가이샤 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
US8624067B2 (en) * | 2009-04-23 | 2014-01-07 | Daikin Industries, Ltd. | Process for preparing 2-chloro-3,3,3-trifluoropropene |
EP2429977B1 (fr) * | 2009-05-13 | 2014-11-05 | Daikin Industries, Ltd. | Procédé pour la préparation d'un composé fluorocarboné contenant du chlore |
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 |
IN2014DN03381A (fr) * | 2011-11-04 | 2015-06-26 | Haiyou Wang | |
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 |
EP2882704B1 (fr) * | 2012-08-08 | 2018-02-28 | Daikin Industries, Ltd. | Procédé pour produire le 2,3,3,3-tétrafluoropropène |
-
2016
- 2016-01-28 FR FR1650673A patent/FR3047240B1/fr not_active Expired - Fee Related
-
2017
- 2017-01-13 CN CN201780007281.5A patent/CN108473395A/zh active Pending
- 2017-01-13 EP EP17706527.3A patent/EP3408248A1/fr not_active Withdrawn
- 2017-01-13 JP JP2018539299A patent/JP6832940B2/ja active Active
- 2017-01-13 WO PCT/FR2017/050079 patent/WO2017129878A1/fr active Application Filing
- 2017-01-13 US US16/071,751 patent/US10487028B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20190031584A1 (en) | 2019-01-31 |
FR3047240B1 (fr) | 2019-09-27 |
US10487028B2 (en) | 2019-11-26 |
FR3047240A1 (fr) | 2017-08-04 |
WO2017129878A1 (fr) | 2017-08-03 |
JP6832940B2 (ja) | 2021-02-24 |
JP2019504841A (ja) | 2019-02-21 |
CN108473395A (zh) | 2018-08-31 |
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