WO2012000853A1 - Process for the synthesis of trifluoroethylene - Google Patents
Process for the synthesis of trifluoroethylene Download PDFInfo
- Publication number
- WO2012000853A1 WO2012000853A1 PCT/EP2011/060400 EP2011060400W WO2012000853A1 WO 2012000853 A1 WO2012000853 A1 WO 2012000853A1 EP 2011060400 W EP2011060400 W EP 2011060400W WO 2012000853 A1 WO2012000853 A1 WO 2012000853A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- activated carbon
- catalyst
- chlorotrifluoroethylene
- palladium
- trifluoroethylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 74
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 35
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910002666 PdCl2 Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229910003609 H2PtCl4 Inorganic materials 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(II) nitrate Inorganic materials [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/617—500-1000 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/618—Surface area more than 1000 m2/g
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
Definitions
- the present invention relates to a catalytic process for the synthesis of trifluoroethylene.
- the invention relates to a process for the synthesis of trifluoroethylene by reaction of chlorotrifluoroethylene with hydrogen in the presence of a heterogeneous catalyst.
- US 3564064 19710216 discloses the catalytic gas-phase reaction of chlorotrifluoroethylene with hydrogen to produce trifluoroethylene in the presence of a catalyst comprising palladium or platinum supported on activated carbon. This process may proceed with high conversion of chlorotrifluoroethylene but with a parallel reduction in the yield of trifluoroethylene.
- a first object of the present invention is a process for preparing trifluoroethylene comprising contacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst consisting of palladium or platinum supported on activated carbon, in which the activated carbon is extruded activated carbon.
- a second object is a catalyst for the hydrodechlorination of chlorotrifluoroethylene, said catalyst consisting of palladium or platinum supported on activated carbon, characterized in that the activated carbon is extruded activated carbon.
- activated carbon is generally used to collectively refer to processed carbonaceous materials characterized by a porous structure and a large internal surface area, generally comprised between 500 and 1500 m 2 /g.
- Activated carbon is obtained on a commercial scale from carbon containing raw materials, e.g. wood, peat, coconut shells, by chemical or gas activation.
- Activated carbon is commercially available in different forms, namely granular, powdered or extruded form.
- Extruded activated carbon is typically obtained from finely powdered raw materials by mixing with a suitable binder followed by extrusion, to form pellets or strands which are then cut into pieces. The pellets are then chemically activated or carbonized and finally gas activated. Typical extruded activated carbons have a pellet diameter in the range of 0.8 to 130 mm.
- Suitable extruded activated carbons for the process of the invention are available commercially for instance from Norit Nederland B.V., Degussa AG, Calgon Carbon Corporation.
- the process of the invention is preferably carried out in the gas-phase.
- a gaseous stream of hydrogen and chlorotrifluoroethylene is fed to the reaction zone and brought into contact with the catalyst held at a suitable temperature.
- the produced trifluoroethylene is recovered from the effluent gas.
- the reaction products and any unreacted starting material may be recovered and isolated by conventional methods.
- the main by-product of the process has been identified to be CH 2 FCHF 2 .
- the molar ratio between the hydrogen and the chlorotrifluoroethylene fed to the reaction zone is typically comprised between 0.75:1 and 1.25:1, preferably between 0.9:1 and 1.1:1.
- An inert gas may be optionally mixed with hydrogen and chlorotrifluoroethylene.
- Suitable inert gases are for instance nitrogen, helium, argon.
- the inert gas is nitrogen.
- the inert gas may serve as a diluent to reduce the concentration of the reactants and/or the products below the point where they form flammable mixtures.
- the concentration of chlorotrifluoroethylene in the gaseous stream fed to the reaction zone is conveniently comprised between 5 and 55% by volume, preferably between 10 and 50% by volume.
- the reaction pressure is not critical to the process. Generally the process is carried out at pressure of from 0.01 MPa to 0.5 MPa, preferably at a pressure of from about 0.05 MPa to 0.2 MPa.
- the reaction may be conducted at any suitable temperature, generally at a temperature in the range of from 100°C to 350°C, preferably in the range of from 150°C to 300°C, and more preferably in the range of from 200°C to 250°C.
- the reaction contact time for the reactants may be any suitable contact time, usually a time of from 0.1 second to 100 seconds, preferably from 0.1 second to 60 seconds, and more preferably from 0.5 second to 30 seconds.
- any suitable space velocity of the reactants may be employed.
- the space velocity can be in the range from 0.2 to 50 gCTFE*h -1 *g cat -1 , preferably from 1 to 40 gCTFE*h -1 *g cat -1 and more preferably from 2 to 30 gCTFE*h -1 *g cat -1 .
- the process may be conducted in any suitable reaction vessel.
- the reaction vessel should be constructed of materials which are inert towards the reactants as well as the products, such as for example, Hastelloy, Inconel, Monel, stainless steel vessels.
- the process is carried out in a tubular stainless steel reactor, provided with suitable means to maintain the required temperature inside the reactor.
- the catalyst used in the process consists of platinum or palladium supported on extruded activated carbon.
- the catalyst consists of palladium supported on extruded activated carbon.
- the amount of metal supported on the extruded activated carbon is typically comprised between 0.05 and 5% by weight, preferably between 0.1 and 4% by weight, more preferably between 0.2 and 3% by weight, and even more preferably between 0.3 and 2.5% by weight.
- the catalyst may be prepared by conventional methods, such as the incipient wetness impregnation method. In such a method an aqueous solution of a suitable metal precursor is added to the support, dried, followed by reduction of the metal.
- a suitable metal precursor mention can be made of PdCl 2 , Pd(NO 3 ) 2 , H 2 PtCl 4 .
- NORIT ® GCN 1240 (Norit Nederland B.V.) granular activated carbon having BET area of 1300 m 2 /g
- the activated carbon as received from the supplier was crushed and sieved in order to obtain granules with a diameter of 0.5-1 mm.
- the granules were dried under vacuum at 200°C and then impregnated with incipient wetness method with an aqueous hydrochloridric solution of PdCl 2 to obtain different concentrations of palladium on the support.
- Catalyst activation Each catalyst was dried under a nitrogen flow at 300°C for 6 h and then reduced in a H 2 /N 2 stream (5% by volume H 2 ) from room temperature to 350°C with thermal ramp of 5°C/min. After 30 minutes at 350°C hydrogen concentration was raised to 10% by volume and kept for 30 minutes, followed by a treatment with a hydrogen concentration of 50 % by volume for 4 h. At the end of the treatment the catalyst was cooled at room temperature and characterized to determine the effective concentration of palladium.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Catalyst | Pd (%wt ) |
A | 1.14 |
B | 0.51 |
Run | Catalyst | CTFE (vol%) | Space velocity (g/h *CTFE * gcat-1) | Residence time (sec) | Conversion CTFE (%) | Selectivity TrFE (%) |
1 | A | 33 | 2.6 | 4.2 | 93 | 71 |
2 | A | 11 | 2.6 | 1.5 | 93 | 75 |
3 | B | 33 | 2.6 | 4.2 | 98 | 70 |
Run | Catalyst | CTFE (vol%) | Space velocity (g/h *CTFE * gcat-1) | Residence time (sec) | Conversion CTFE (%) | Selectivity TrFE (%) |
4 | A | 30 | 3.6 | 1.5 | 93 | 79 |
5 | A | 33 | 13.9 | 0.4 | 91 | 82 |
6 | A | 34 | 29.5 | 0.2 | 83 | 80 |
7 | C | 29 | 3.6 | 1.5 | 82 | 73 |
8 | C | 32 | 13.5 | 0.4 | 80 | 73 |
9 | C | 33 | 29.9 | 0.2 | 71 | 72 |
Claims (6)
- Process for preparing trifluoroethylene comprising contacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst consisting of palladium or platinum supported on activated carbon, characterized in that the activated carbon is extruded activated carbon.
- Process according to claim 1 wherein the catalyst consists of palladium supported on extruded activated carbon.
- Process according to claim 1 or 2 which is carried out in the gas-phase by contacting a gasous stream of chlorotrifluoroethylene and hydrogen, optionally comprising an inert gas, with the catalyst.
- Process according to claim 3 wherein the concentration of chlorotrifluoroethylene in the gaseous stream is comprised between 5 and 55% by volume, preferably between 10 and 50% by volume.
- A catalyst consisting of palladium or platinum, preferably palladium, supported on activated carbon, characterized in that the activated carbon is extruded activated carbon.
- Catalyst according to claim 5 wherein the amount of palladium or platinum supported on the extruded activated carbon is comprised between 0.05 and 5% by weight.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11727967.9A EP2588434B1 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
US13/704,001 US20130131402A1 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
RU2013104169/04A RU2570812C2 (en) | 2010-07-01 | 2011-06-22 | Method and catalyst for trifluoroethylene synthesis |
CN201180032991.6A CN102971278B (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
JP2013517185A JP5964823B2 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
US14/310,230 US9403742B2 (en) | 2010-07-01 | 2014-06-20 | Process for the synthesis of trifluoroethylene |
US15/195,576 US20160303543A1 (en) | 2010-07-01 | 2016-06-28 | Process for the synthesis of trifluoroethylene |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10168130.2 | 2010-07-01 | ||
EP10168130 | 2010-07-01 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/704,001 A-371-Of-International US20130131402A1 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
US14/310,230 Division US9403742B2 (en) | 2010-07-01 | 2014-06-20 | Process for the synthesis of trifluoroethylene |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012000853A1 true WO2012000853A1 (en) | 2012-01-05 |
Family
ID=43084464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2011/060400 WO2012000853A1 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
Country Status (6)
Country | Link |
---|---|
US (3) | US20130131402A1 (en) |
EP (1) | EP2588434B1 (en) |
JP (1) | JP5964823B2 (en) |
CN (1) | CN102971278B (en) |
RU (1) | RU2570812C2 (en) |
WO (1) | WO2012000853A1 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130131402A1 (en) * | 2010-07-01 | 2013-05-23 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
WO2013113785A1 (en) | 2012-02-02 | 2013-08-08 | Solvay Specialty Polymers Italy S.P.A. | Stable compositions of trifluoroethylene |
JP2015513545A (en) * | 2012-02-28 | 2015-05-14 | アルケマ フランス | Method for the synthesis of trifluoroethylene from chlorotrifluoroethylene |
US20160002518A1 (en) * | 2013-04-30 | 2016-01-07 | Asahi Glass Company, Limited | Composition containing trifluoroethylene |
US9902672B2 (en) | 2014-08-25 | 2018-02-27 | Asahi Glass Company, Limited | Method for producing hydrofluoroolefin |
US9988327B2 (en) | 2014-08-25 | 2018-06-05 | Asahi Glass Company, Limited | Process for producing hydrofluoroolefin |
US10189758B2 (en) | 2014-12-05 | 2019-01-29 | AGC Inc. | Method for producing hydrofluoroolefin |
CN115722272A (en) * | 2022-12-07 | 2023-03-03 | 四川轻化工大学 | Preparation method and application of high-stability core-shell structure hydrodechlorination catalyst |
WO2023213893A1 (en) * | 2022-05-03 | 2023-11-09 | Arkema France | Method for producing trifluoroethylene |
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JP6384475B2 (en) * | 2013-04-30 | 2018-09-05 | Agc株式会社 | Working medium for heat cycle |
EP4043421A1 (en) * | 2014-02-20 | 2022-08-17 | Agc Inc. | Method for purifying fluid that includes trifluoroethylene, and method for producing trifluoroethylene |
JP7553758B2 (en) * | 2019-07-10 | 2024-09-19 | ダイキン工業株式会社 | Method for producing vinyl compounds |
CN110590495A (en) * | 2019-08-21 | 2019-12-20 | 福建省杭氟电子材料有限公司 | Preparation method of hexafluorobutadiene |
JP7348535B2 (en) | 2021-07-15 | 2023-09-21 | ダイキン工業株式会社 | Alkene production method |
CN114797846A (en) * | 2022-05-24 | 2022-07-29 | 四川轻化工大学 | Catalyst for hydrodechlorination and preparation method thereof |
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2011
- 2011-06-22 US US13/704,001 patent/US20130131402A1/en not_active Abandoned
- 2011-06-22 EP EP11727967.9A patent/EP2588434B1/en active Active
- 2011-06-22 CN CN201180032991.6A patent/CN102971278B/en active Active
- 2011-06-22 JP JP2013517185A patent/JP5964823B2/en active Active
- 2011-06-22 WO PCT/EP2011/060400 patent/WO2012000853A1/en active Application Filing
- 2011-06-22 RU RU2013104169/04A patent/RU2570812C2/en active
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2014
- 2014-06-20 US US14/310,230 patent/US9403742B2/en active Active
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2016
- 2016-06-28 US US15/195,576 patent/US20160303543A1/en not_active Abandoned
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Cited By (19)
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US20140303411A1 (en) * | 2010-07-01 | 2014-10-09 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
US9403742B2 (en) * | 2010-07-01 | 2016-08-02 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
US20130131402A1 (en) * | 2010-07-01 | 2013-05-23 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
WO2013113785A1 (en) | 2012-02-02 | 2013-08-08 | Solvay Specialty Polymers Italy S.P.A. | Stable compositions of trifluoroethylene |
US9266800B2 (en) | 2012-02-02 | 2016-02-23 | Solvay Specialty Polymers Italy S.P.A. | Stable compositions of trifluoroethylene |
JP2015513545A (en) * | 2012-02-28 | 2015-05-14 | アルケマ フランス | Method for the synthesis of trifluoroethylene from chlorotrifluoroethylene |
US10081749B2 (en) * | 2013-04-30 | 2018-09-25 | AGC Inc. | Composition containing trifluoroethylene |
US20160002518A1 (en) * | 2013-04-30 | 2016-01-07 | Asahi Glass Company, Limited | Composition containing trifluoroethylene |
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US9902672B2 (en) | 2014-08-25 | 2018-02-27 | Asahi Glass Company, Limited | Method for producing hydrofluoroolefin |
US9988327B2 (en) | 2014-08-25 | 2018-06-05 | Asahi Glass Company, Limited | Process for producing hydrofluoroolefin |
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US10189758B2 (en) | 2014-12-05 | 2019-01-29 | AGC Inc. | Method for producing hydrofluoroolefin |
WO2023213893A1 (en) * | 2022-05-03 | 2023-11-09 | Arkema France | Method for producing trifluoroethylene |
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CN115722272A (en) * | 2022-12-07 | 2023-03-03 | 四川轻化工大学 | Preparation method and application of high-stability core-shell structure hydrodechlorination catalyst |
CN115722272B (en) * | 2022-12-07 | 2024-03-26 | 四川轻化工大学 | Preparation method and application of high-stability core-shell structure hydrodechlorination catalyst |
Also Published As
Publication number | Publication date |
---|---|
US20130131402A1 (en) | 2013-05-23 |
RU2013104169A (en) | 2014-08-10 |
JP2013534529A (en) | 2013-09-05 |
US20160303543A1 (en) | 2016-10-20 |
CN102971278B (en) | 2014-12-17 |
EP2588434A1 (en) | 2013-05-08 |
CN102971278A (en) | 2013-03-13 |
US20140303411A1 (en) | 2014-10-09 |
JP5964823B2 (en) | 2016-08-03 |
RU2570812C2 (en) | 2015-12-10 |
US9403742B2 (en) | 2016-08-02 |
EP2588434B1 (en) | 2016-11-02 |
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