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WO2010059496A1 - Procédé de fabrication d'hydrochlorofluorooléfines - Google Patents

Procédé de fabrication d'hydrochlorofluorooléfines Download PDF

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Publication number
WO2010059496A1
WO2010059496A1 PCT/US2009/064145 US2009064145W WO2010059496A1 WO 2010059496 A1 WO2010059496 A1 WO 2010059496A1 US 2009064145 W US2009064145 W US 2009064145W WO 2010059496 A1 WO2010059496 A1 WO 2010059496A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
trans
isomerization
group
fluorination
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.)
Ceased
Application number
PCT/US2009/064145
Other languages
English (en)
Inventor
Maher Y. Elsheikh
Philippe Bonnet
John A. Wismer
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 Inc
Original Assignee
Arkema Inc
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
Priority to JP2011537508A priority Critical patent/JP5571682B2/ja
Priority to CA2743670A priority patent/CA2743670C/fr
Priority to ES09828044T priority patent/ES2779348T3/es
Priority to CN2009801467757A priority patent/CN102216247A/zh
Priority to PL09828044T priority patent/PL2349962T3/pl
Priority to US13/127,817 priority patent/US8642819B2/en
Application filed by Arkema Inc filed Critical Arkema Inc
Priority to EP09828044.9A priority patent/EP2349962B1/fr
Publication of WO2010059496A1 publication Critical patent/WO2010059496A1/fr
Anticipated expiration legal-status Critical
Priority to US14/167,150 priority patent/US8987534B2/en
Priority to US14/183,828 priority patent/US8987535B2/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/06—Preparation of halogenated hydrocarbons by addition of halogens combined with replacement of hydrogen atoms by halogens
    • 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
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

Definitions

  • the present invention relates to a process for the manufacture of hydrochlorofluoroolefins.
  • CFCs chlorofluorocarbons
  • HFCs hydrofluorocarbons
  • ODP negligible ozone depletion potential
  • GWP acceptable low global warming potential
  • the present invention describes a process for manufacturing of the hydrochlorofluoroolefin, trans 1233zd (E- 1233zd, l-chloro-3,3,3-trifluorpropene) which is useful as a low ODP and low GWP blowing agent for thermoset and thermoplastic foams, solvent, heat transfer fluid such as ; in heat pumps, and refrigerant such as a low pressure refrigerant for chillers.
  • US patent publications US2008/0051610 and US2008/0103342 disclose a process that includes a step of the catalytic isomerization of cis 1234ze to trans 1234ze.
  • US 7,420,094 discloses the isomerization of 1234ze to 1234yf with a Cr based catalyst.
  • US2008/0051611 discloses the recovery of trans 1234ze from a mixture that includes cis 1234ze and trans 1234ze via distillation.
  • the present invention relates a process for the manufacture of the hydrochlorofluoroolefin, trans l-chloro-3,3,3-trifluoropropene (E-1233zd).
  • the process comprises an isomerization step from cis 1233zd (Z-1233zd) to trans 1233zd (E- 1233zd).
  • Figure 1 is a schematic of a liquid phase process in accordance with the present invention.
  • Figure 2 is schematic of a gas phase process in accordance with the present invention.
  • the present invention provides a process for the manufacture of trans l-chloro-3,3,3- trifluoropropene (E-1233zd).
  • the second step of the process comprises a separation of the mixture formed in the first step to isolate cis 1233zd (Z-1233zd) from the mixture.
  • the third step of the process comprises isomerization of cis 1233zd (Z-1233zd) to trans 1233zd (E- 1233zd).
  • VCM vinyl chloride monomer
  • CH 2 CHCl
  • the first step of the process gas phase fluorination of 1230za and/or 240fa to 1233zd or liquid phase fluorination of 1230za to 12333zd; can be via any process known in the art.
  • gas phase fluorination of 1230za and/or 240fa to 1233zd or liquid phase fluorination of 1230za to 12333zd can be via any process known in the art.
  • the uncatalyzed liquid phase fluorination of 1230za is disclosed in US Patent No. 5,877,359
  • the catalyzed gas phase fluorination of 1230za is disclosed in US 5 Patent No. 5,811 ,603
  • 6,166,274 discloses the fluorination of 1230za to 1233zd in the presence of catalyst such as trifluoroacetic acid or triflic acid.
  • catalyst such as trifluoroacetic acid or triflic acid.
  • an Sb type catalyst it is preferred to feed low level of Cl 2 to maintain the Sb species in an active form.
  • the second step of the process comprises the separation of the cis 1233zd and trans 1233zd formed in the first step via an appropriate separation means such as distillation, liquid phase separation, or extractive separation.
  • the cis 1233zd and trans 1233zd formed in the first step may contain HF and HCl.
  • the HCl is first removed in a first distillation column.
  • liquid phase separation coupled with azeotropic ' ⁇ 15 : distillation can be used to remove HF.
  • the boiling point difference of cis 1233zd and trans 1233zd enable them to be separated by conventional distillation, typically at atmospheric pressures.
  • the third step of the process involves the isomerization of the cis 1233zd from the second step into trans 1233zd.
  • the isomerization step can be carried out in the gas phase or in 20 the liquid phase using respectively a heterogeneous or a homogeneous catalyst.
  • the isomerization step is achievable with a gas phase process in the presence of a heterogeneous catalyst.
  • a suitable heterogeneous catalyst is high surface area Cr* ⁇ ° catalyst, supported or unsupported, that can optionally contains low levels of one or more co-catalysts selected from cobalt, nickel, zinc or manganese.
  • cobalt nickel, zinc or manganese.
  • catalyst support can be selected from materials known in the art to be compatible with high temperature and pressure processes.
  • fluorinated alumina, HF treated activated carbon or carbon graphite are suitable catalyst supports.
  • a preferred catalyst is a high surface area unsupported chromium oxide catalyst that is activated with HF before use, optionally at pressure above 50 psi.
  • the level of the co-catalyst, when present, can be 0 varied from 1 to 10 weight %, preferably from 1 to 5 weight % of the catalyst.
  • Co- catalyst can be added to the catalyst by processes known in the art such as adsorption from an aqueous or organic solvent, followed by solvent evaporation.
  • Suitable heterogeneous catalyst can also be selected from: Lewis acids supported catalysts selected from Sb v , Ti ⁇ , Sn lv , Mo VI , Nb v and Ta v
  • the support itself is selected from the group such as fluorinated alumina; fluorinated chromia; HF activated carbon or graphite carbon .
  • Supported antimony halides such as SbF 5 are described in US Patent No. 6,528,691 and are preferred catalysts.
  • Other solid catalysts such as NAFION ® type polymer, acidic molecular sieves and, zeolites can be also used.
  • the temperature can be varied between 20-500 0 C, preferably between 100-400 0 C.
  • Contact times can vary from 0.5 to 100 seconds.
  • a low level of oxidizing agent such as oxygen or oxygen containing gas such as air or chlorine gas can be used at between .01- .1 volume percent to prolong the life of the catalyst.
  • the isomerization step is also achievable in a liquid phase process in the presence of a homogenous catalyst preferably selected from compounds of group 3, 4, 5, 13, 14 and 15 metal compounds of the Periodic Table of the elements (IUPAC 1988) and their mixtures (groups of the Periodic Table of the elements which were previously called IHA, IVa, IVb 5 Va, Vb and VIb).
  • a homogenous catalyst preferably selected from compounds of group 3, 4, 5, 13, 14 and 15 metal compounds of the Periodic Table of the elements (IUPAC 1988) and their mixtures (groups of the Periodic Table of the elements which were previously called IHA, IVa, IVb 5 Va, Vb and VIb).
  • the compounds of the metals are intended to include hydroxides, oxides and the organic or inorganic salts of these metals, as well as mixtures thereof.
  • the aluminum, titanium, tantalum, molybdenum, boron, tin and antimony derivatives such as AlCl 3 , TiCl 4 , TaCl 5 , MoCI 6 , BF 3 , SnCl 4 , and SbClS.
  • the catalyst must be subjected to activation (by HF or any molecule able to exchange fluorine) prior to the isomerization step.
  • activation by HF or any molecule able to exchange fluorine
  • a low level of chlorine gas as oxidizing agent can be used to maintain the antimony catalyst in the pentavalent oxidation state.
  • an ionic liquid derived from antimony, titanium, niobium and tantalum is suitable for liquid phase fluorination processes. A description of the preparation of such catalysts is disclosed in the US Patent No. 6,881,698.
  • the homogenous catalyst for a liquid phase process can also be selected from the Bronsted type family of acids such as (but not limited to) sulfuric acid H 2 SO 4 , sulfonic type acids such as ClSO 3 H or FSO 3 H or triflic acid CF 3 SO 3 H or methane sulfonic acid CH 3 SO 3 H.
  • the operating temperature can be varied between about 20-200 0 C, with a contact time between about 0.5-50 hours.
  • the process of the present invention may comprise additional separation steps between each step.
  • the purpose of theses separations could be:
  • the means used to achieve these additional steps are known in the art and include but are not limited to: distillation, extractive distillation or adsorption.
  • RFL- comprises a liquid phase fluorination reactor and rectification system comprising an unagitated, jacketed pressure vessel connected to a rectification column.
  • the reactor also acts as the reboiler of the rectification column.
  • the HF and organic (1230za) are fed directly to the reactor.
  • the molar feed ratio of HF to organic is dictated by the reaction stoichiometry and the amount of HF leaving the reactor with the rectification column overhead and liquid phase purges. Mixing is provided by the boiling action of the reactor contents.
  • the reactor effluent leaves the reactor vessel as a gas and enters the bottom of the rectification column.
  • a small purge from the liquid phase can remove any non-volatiles that may form during the reaction.
  • the rectification column contains either packing or trays designed to provide good mass transfer between up flowing gas and down flowing liquid.
  • the condenser at the top of the column is cooled by either cooling water, chilled water, or some type of refrigeration.
  • the condenser is a partial condenser where the liquid effluent is refluxed directly back to the column.
  • the vapor effluent consists of HCl, HF and organic components.
  • DH- comprises an HCl distillation system whereby pure HCl is removed from the top of a distillation column.
  • This column can operate between 100 psig and 300 psig. More typically, the HCl is distilled above 120 psig to allow the use of conventional (-40C) refrigeration at the top of the HCl column.
  • the bottoms of this column contains HF and organic with a small residual amount of HCl. The ratio of HF to the organic component typically is close to the azeotropic composition.
  • PS- comprises a liquid phase separator to separate two liquid phases, one consisting primarily of a hydrochlorofluorocarbon (HCFC) and the other consisting primarily of HF.
  • HCFC hydrochlorofluorocarbon
  • the HF phase is usually the less dense so that it exits from the top of the phase separator and the HCFC exits as the bottom phase.
  • the operating temperature of the phase separator can be between — 40 0 C and +2O 0 C. However, the lower the temperature, the better the phase separation.
  • DA- comprises an azeotropic distillation column which distills overhead an azeotropic composition of HF and an organic consisting of one or more HCFCs (hydrochlorofluorocarbons) and HFC's (hydrofluorocarbons). These organic compounds can be either saturated or olefinic.
  • the bottoms composition is either entirely HF or entirely organic, depending on whether the column feed composition is on the HF rich side or the organic rich side of the azeotrope. If the bottoms are HF, this stream is normally recycled back to the reactor. If the bottoms steam is organic, it is sent to a conventional distillation train,
  • DS- comprises a straight distillation normally done under pressure.
  • RI comprises a gas phase isomerization reaction typically done at temperatures above 400 0 C in an adiabatic, packed bed reactor.
  • the module consists of a feed vaporizer and superheater. It can include an "economizer", whereby hot effluent is fed to one side and relatively cold reactor feed gases are fed to another side of a heat exchanger. The effluent gases are further cooled before entering a distillation column.
  • Isomerization reactions can be run at varying conversions depending on the equilibrium distribution of isomers.
  • the effluent isomers can have boiling points very close together. However, they typically exhibit close to ideal behavior so can be separated by conventional distillation.
  • this reaction can be done as a homogeneously catalyzed liquid phase reaction. In this configuration, the reactor would be a continuous stirred tank with the effluent being removed as a vapor to effect separation from the catalyst.
  • RFG- comprises a gas phase fluorination reactor that is an adiabatic packed bed reactor that feeds a gas phase over a solid catalyst. No cooling is needed because of the reactor has a low conversion per pass arid a high HF molar feed ratio.
  • the adiabatic exo therm is typically less than 100 0 C.
  • the feed HF and organic are vaporized in a common vaporizer and superheated to the reactor temperature.
  • the common vaporizer allows the 1230za and/or 240fa to be vaporized at a lower temperature than would be possible if it were vaporized as a pure component, thereby minimizing thermal degradation.
  • This module can also include an "economizer", whereby hot effluent is fed to one side and relatively cold reactor feed gases are fed to another side of a heat exchanger. The effluent gases are further cooled before entering a distillation column. Reaction temperatures are between 200 0 C and 400°C. The pressure is high enough to allow the HCl by-product to be distilled with conventional refrigeration- preferably between 100 psig and 200 psig.
  • the lower case letter used to identify the modules distinguishes multiple appearances of the same type of module in the same process.
  • Figure 1 is a block flow diagram of a process in accordance with the present invention for converting 1230za to E-1233zd using a liquid phase fluorination step.
  • the Figure incorporates the process modules described above.
  • Figure 1 discloses a process wherein 1230za and HF are fed to reaction module RFL-I. Typically, the reaction takes place in a predominantly HF rich medium without a catalyst.
  • the HCl and the 1233zd/HF exit the top of the rectification column of RFL-I .
  • the vapor effluent of RFL-I enters DH-I to remove HCl as a pure overhead product.
  • the bottoms of DH-I consists primarily of 1233zd (both E and Z isomers) and HF at a near azeotropic composition. This is fed to module PS-I to effect a liquid phase separation.
  • the top HF rich phase is sent to module DA-Ia, where HF is separated as a bottoms stream for recycle to the reactor.
  • the overhead azeotrope of 1233zd and HF is recycled back to DH-I to allow any residual HCl and light organics to be stripped out in this column before the azeotrope gets recycled to phase separation.
  • the bottoms stream from PS-I goes to module DA-Ib, which removes an organic stream devoid of HF as a bottoms stream.
  • the overhead from DA-Ib is recycled to DH-I for the same reason that the DA-Ia azeotrope was recycled to DH-I.
  • the bottoms of DA-Ib is sent to process module DS-I that separates any heavies from the 1233zd.
  • the overhead from DS-I is E-1233zd, the desired trans isomer.
  • the Z- 1233zd is higher boiling and is recovered for feeding to process module RI-I .
  • the effluent from the isomerization reactor is recycled to DS-I , which effects the separation of the E and Z isomers.
  • FIG. 2 is a block flow diagram of a process in accordance with the present invention for converting 1230za or 240fa to E-1233zd using a gas phase fluorination step.
  • the Figure incorporates the process modules described above.
  • the process is similar to Figure 1 except, for example, the liquid phase fluorination reactor (RFL-I) is replaced by a gas phase fluorination reactor (RFG-I) and azeotropic distillation column (DA-2a).
  • RTL-I liquid phase fluorination reactor
  • RFG-I gas phase fluorination reactor
  • DA-2a azeotropic distillation column
  • the process as outlined by Figure 2 comprises feeding 1230za and/or 240fa and HF to reaction module RFG-2.
  • the reaction takes place in a gas phase with a catalyst.
  • the reactor effluent consists of predominantly HCl, 1233zd, unreacted 1230za and excess HF.
  • the reactor effluent of RFG-2 enters DA-2a to remove HF and unreacted F 1230za as bottoms that is recycled to the reactor.
  • the overhead which consists predominantly of HCl and the azeotrope of HF and 1233zd (both E and Z isomers), is sent to DH-2, which removes HCl as a pure overhead product.
  • the bottoms of DH-2 consists of primarily 1233zd (both E and Z isomers) and HF at a near azeotropic composition. This is fed to module PS-2 to effect a liquid phase separation.
  • the top HF rich phase is sent to module DA-2b, where HF is separated as a bottoms stream for recycle to the reactor.
  • the overhead azeotrope of 1233zd and HF is recycled back to DH-2 to allow any residual HCl and light organics to be stripped out in this column before the azeotrope gets recycled to phase separation.
  • the bottoms stream from PS-2 goes to module DA-2c, which removes an organic stream devoid of HF as a bottoms stream.
  • the overhead from DA-2c is recycled to DH-2 for the same reason that the DA-2b azeotrope was recycled to DH-2.
  • the bottoms of DA-2c is sent to process module D S -2 that separates any heavies from the 1233zd.
  • the overhead from DS-2 is E-1233zd- the desired trans isomer.
  • the Z-1233zd is higher boiling and is recovered for feeding to process module RI-2.
  • the effluent from the isomerization reactor is recycled to DS-2, which effects the separation of the E and Z isomers.

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

Abstract

La présente invention porte sur un procédé de fabrication de trans 1-chloro-3,3,3-trifluoropropène (E-1223zd). La première étape du procédé comprend la fluoration du 1,1,3,3-tétrachloropropène (1230za, CCh=CH-CHCh) et/ou du 1,1,1,3,3-pentachloropropane (240fa) en un mélange de cis 1233zd (Z-1233zd) et de trans 1233zd (E-1233zd). La seconde étape du procédé comprend une séparation du mélange formé dans la première étape pour isoler le cis 1233zd (Z-1233zd) à partir du mélange. La troisième étape du procédé comprend l'isomérisation de cis 1233zd (Z-1233zd) en trans 1233zd (E-1233zd).
PCT/US2009/064145 2008-11-19 2009-11-12 Procédé de fabrication d'hydrochlorofluorooléfines Ceased WO2010059496A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA2743670A CA2743670C (fr) 2008-11-19 2009-11-12 Procede de fabrication d'hydrochlorofluoroolefines
ES09828044T ES2779348T3 (es) 2008-11-19 2009-11-12 Procedimiento para la fabricación de hidroclorofluoroolefinas
CN2009801467757A CN102216247A (zh) 2008-11-19 2009-11-12 用于制造氢氯氟烯烃的方法
PL09828044T PL2349962T3 (pl) 2008-11-19 2009-11-12 Sposób wytwarzania chlorofluorowodoroolefin
US13/127,817 US8642819B2 (en) 2008-11-19 2009-11-12 Process for the manufacture of hydrochlorofluoroolefins
JP2011537508A JP5571682B2 (ja) 2008-11-19 2009-11-12 ヒドロクロロフルオロオレフィンを製造するための方法
EP09828044.9A EP2349962B1 (fr) 2008-11-19 2009-11-12 Procédé de fabrication d'hydrochlorofluorooléfines
US14/167,150 US8987534B2 (en) 2008-11-19 2014-01-29 Process for the manufacture of hydrochlorofluoroolefins
US14/183,828 US8987535B2 (en) 2008-11-19 2014-02-19 Process for the manufacture of hydrochlorofluoroolefins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11605608P 2008-11-19 2008-11-19
US61/116,056 2008-11-19

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/127,817 A-371-Of-International US8642819B2 (en) 2008-11-19 2009-11-12 Process for the manufacture of hydrochlorofluoroolefins
US14/167,150 Continuation-In-Part US8987534B2 (en) 2008-11-19 2014-01-29 Process for the manufacture of hydrochlorofluoroolefins

Publications (1)

Publication Number Publication Date
WO2010059496A1 true WO2010059496A1 (fr) 2010-05-27

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PCT/US2009/064145 Ceased WO2010059496A1 (fr) 2008-11-19 2009-11-12 Procédé de fabrication d'hydrochlorofluorooléfines

Country Status (8)

Country Link
US (1) US8642819B2 (fr)
EP (1) EP2349962B1 (fr)
JP (1) JP5571682B2 (fr)
CN (2) CN105646135A (fr)
CA (1) CA2743670C (fr)
ES (1) ES2779348T3 (fr)
PL (1) PL2349962T3 (fr)
WO (1) WO2010059496A1 (fr)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110201853A1 (en) * 2010-02-18 2011-08-18 Honeywell International Inc. Integrated Process And Methods Of Producing (E)-1-Chloro-3,3,3-Trifluoropropene
WO2012030797A2 (fr) 2010-09-03 2012-03-08 Honeywell International Inc. Procédé continu de production de trans-1-chloro-3,3,3-trifluoropropène à basse température
JP2012158552A (ja) * 2011-02-01 2012-08-23 Central Glass Co Ltd シス−１−クロロ−３，３，３−トリフルオロプロペンの製造方法
WO2012094288A3 (fr) * 2011-01-04 2012-08-30 Honeywell International Inc. E-1-chloro-3,3,3-trifluoropropène de pureté élevée et procédés pour le produire
US20120271070A1 (en) * 2011-04-25 2012-10-25 Haiyou Wang INTEGRATED PROCESS TO CO-PRODUCE 1,1,1,3,3-PENTAFLUOROPROPANE, TRANS-1-CHLORO-3,3,3-TRIFLUOROPROPENE and TRANS-1,3,3,3-TETRAFLUOROPROPENE
WO2012145188A2 (fr) 2011-04-20 2012-10-26 Honeywell International Inc. Procédé de production de trans-1233zd
WO2013077189A1 (fr) * 2011-11-21 2013-05-30 セントラル硝子株式会社 Procédé de fabrication de trans-1-chloro-3,3,3-trifluoropropène
WO2013115048A1 (fr) * 2012-02-02 2013-08-08 セントラル硝子株式会社 Procédé de purification du (e)-1-chloro-3,3,3-trifluoropropène
US8653310B2 (en) 2011-12-07 2014-02-18 Honeywell International Inc. Process for making cis-1-chloro-3,3,3-trifluoropropene
US8754272B2 (en) 2011-12-07 2014-06-17 Honeywell International Inc. Process for cis-1-chloro-3,3,3-trifluoropropene
JP2014518873A (ja) * 2011-05-19 2014-08-07 ハネウェル・インターナショナル・インコーポレーテッド １−クロロ−３，３，３−トリフルオロプロペンを製造するための統合方法
US9018428B2 (en) 2012-09-06 2015-04-28 Honeywell International Inc. Reactor and agitator useful in a process for making 1-chloro-3,3,3-trifluoropropene
WO2015104517A1 (fr) * 2014-01-13 2015-07-16 Arkema France Procede de production du e-1-chloro-3,3,3-trifluoropropene a partir du 1,1,3,3-tetrachloropropene
FR3016627A1 (fr) * 2014-01-17 2015-07-24 Arkema France Procede de production du e-1-chloro-3,3,3-trifluoropropene a partir du 1,1,3,3-tetrachloropropene
US9216932B2 (en) 2013-05-20 2015-12-22 Honeywell International Inc. Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene
FR3036398A1 (fr) * 2015-05-22 2016-11-25 Arkema France Compositions a base de 1,1,3,3-tetrachloropropene
JP2017110020A (ja) * 2008-12-12 2017-06-22 ハネウェル・インターナショナル・インコーポレーテッド １−クロロ−３，３，３−トリフルオロプロペンの異性化
US9834499B2 (en) 2014-01-13 2017-12-05 Arkema France E-1-chloro-3,3,3-trifluoropropene production process from 1,1,3,3-tetrachloropropene
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EP3296282B1 (fr) 2015-06-02 2020-07-29 Central Glass Company, Limited Procédé de production d'hydrohalofluorooléfines
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