US20130131402A1 - Process for the synthesis of trifluoroethylene - Google Patents
Process for the synthesis of trifluoroethylene Download PDFInfo
- Publication number
- US20130131402A1 US20130131402A1 US13/704,001 US201113704001A US2013131402A1 US 20130131402 A1 US20130131402 A1 US 20130131402A1 US 201113704001 A US201113704001 A US 201113704001A US 2013131402 A1 US2013131402 A1 US 2013131402A1
- Authority
- US
- United States
- Prior art keywords
- activated carbon
- catalyst
- chlorotrifluoroethylene
- palladium
- trifluoroethylene
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 78
- 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 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 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 25
- 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
-
- 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
- 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
-
- 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.
- U.S. Pat. No. 3,564,064 16.02.1971 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® RX3 EXTRA (Norit Nederland B.V.) extruded activated carbon having BET area of 1400 m 2 /g
- 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.
- Catalyst C Following the general catalyst preparation procedure described above one catalyst was prepared using the granular activated carbon NORIT® GCN 1240 as the support and having a palladium concentration of 1.17% by weight (Catalyst C).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10168130.2 | 2010-07-01 | ||
| EP10168130 | 2010-07-01 | ||
| PCT/EP2011/060400 WO2012000853A1 (fr) | 2010-07-01 | 2011-06-22 | Procédé de synthèse de trifluoroéthylène |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2011/060400 A-371-Of-International WO2012000853A1 (fr) | 2010-07-01 | 2011-06-22 | Procédé de synthèse de trifluoroéthylène |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/310,230 Division US9403742B2 (en) | 2010-07-01 | 2014-06-20 | Process for the synthesis of trifluoroethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20130131402A1 true US20130131402A1 (en) | 2013-05-23 |
Family
ID=43084464
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13/704,001 Abandoned US20130131402A1 (en) | 2010-07-01 | 2011-06-22 | Process for the synthesis of trifluoroethylene |
| US14/310,230 Active US9403742B2 (en) | 2010-07-01 | 2014-06-20 | Process for the synthesis of trifluoroethylene |
| US15/195,576 Abandoned US20160303543A1 (en) | 2010-07-01 | 2016-06-28 | Process for the synthesis of trifluoroethylene |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/310,230 Active US9403742B2 (en) | 2010-07-01 | 2014-06-20 | Process for the synthesis of trifluoroethylene |
| US15/195,576 Abandoned US20160303543A1 (en) | 2010-07-01 | 2016-06-28 | Process for the synthesis of trifluoroethylene |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US20130131402A1 (fr) |
| EP (1) | EP2588434B1 (fr) |
| JP (1) | JP5964823B2 (fr) |
| CN (1) | CN102971278B (fr) |
| RU (1) | RU2570812C2 (fr) |
| WO (1) | WO2012000853A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170144949A1 (en) * | 2014-08-25 | 2017-05-25 | Asahi Glass Company, Limited | Method for producing hydrofluoroolefin |
| US9862660B2 (en) | 2014-02-20 | 2018-01-09 | Asahi Glass Company, Limited | Method for purifying fluid that includes trifluoroethylene, and method for producing trifluoroethylene |
| 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 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2588434B1 (fr) * | 2010-07-01 | 2016-11-02 | Solvay Specialty Polymers Italy S.p.A. | Procédé de synthèse de trifluoroéthylène |
| WO2013113785A1 (fr) | 2012-02-02 | 2013-08-08 | Solvay Specialty Polymers Italy S.P.A. | Compositions stables de trifluoroéthylène |
| FR2987358B1 (fr) * | 2012-02-28 | 2016-10-21 | Arkema France | Procede de synthese du trifluoroethylene a partir du chlorotrifluoroethylene |
| EP2993212B1 (fr) * | 2013-04-30 | 2019-08-28 | AGC Inc. | Matériau actif pour cycle de chaleur |
| EP2993213B1 (fr) * | 2013-04-30 | 2020-07-15 | AGC Inc. | Composition contenant du trifluoroéthylène |
| JP2021014410A (ja) * | 2019-07-10 | 2021-02-12 | ダイキン工業株式会社 | ビニル化合物の製造方法 |
| CN110590495A (zh) * | 2019-08-21 | 2019-12-20 | 福建省杭氟电子材料有限公司 | 一种六氟丁二烯的制备方法 |
| JP7348535B2 (ja) | 2021-07-15 | 2023-09-21 | ダイキン工業株式会社 | アルケンの製造方法 |
| FR3135266A1 (fr) * | 2022-05-03 | 2023-11-10 | Arkema France | Procédé de production du trifluoroéthylène |
| CN114797846A (zh) * | 2022-05-24 | 2022-07-29 | 四川轻化工大学 | 一种用于加氢脱氯的催化剂及其制备方法 |
| CN115722272B (zh) * | 2022-12-07 | 2024-03-26 | 四川轻化工大学 | 一种高稳定核壳结构加氢脱氯催化剂的制备方法及其应用 |
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| US3736265A (en) * | 1970-11-06 | 1973-05-29 | Texaco Inc | Stabilized palladium-carbon catalysts |
| US4399052A (en) * | 1980-12-22 | 1983-08-16 | Kabushiki Kaisha Kobe Seiko Sho | Activated carbonaceous honeycomb body and production method thereof |
| US5783514A (en) * | 1992-03-26 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Shell catalyst, a process for its production and its use |
| US6472343B1 (en) * | 2001-04-11 | 2002-10-29 | Westvaco Corporation | Shaped activated carbon |
| US6573212B2 (en) * | 2001-04-11 | 2003-06-03 | Meadwestvaco Corporation | Method of making shaped activated carbon |
| US6624109B2 (en) * | 2001-10-23 | 2003-09-23 | Council Of Scientific And Industrial Research | Process for the synthesis of highly active modified carbon supported palladium catalyst |
| US6753290B1 (en) * | 1999-07-29 | 2004-06-22 | Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdelenia Rossiiskoi Akademii Nauk | Catalytic composition, method for manufacturing thereof and method for the purification of terephthalic acid |
| US6815391B2 (en) * | 2002-04-30 | 2004-11-09 | Changchun Institute Of Applied Chemistry Chinese Academy Of Science | Method of preparing nano-level platinum/carbon electrocatalyst for cathode of fuel cell |
| US20060154810A1 (en) * | 2004-12-24 | 2006-07-13 | China Petrochemical Corporation | Hydrogenation catalyst, its preparation and use |
| WO2012000853A1 (fr) * | 2010-07-01 | 2012-01-05 | Solvay Solexis S.P.A. | Procédé de synthèse de trifluoroéthylène |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2802887A (en) * | 1955-08-08 | 1957-08-13 | Allied Chem & Dye Corp | Hydrogenation of chlorotrifluoroethylene |
| JPS462324B1 (fr) * | 1966-12-16 | 1971-01-21 | ||
| IT1186307B (it) * | 1985-06-10 | 1987-11-26 | Montefluos Spa | Procedimento per la preparazione di 1,2-difluoroetilene e 1-cloro-1,2-difluoro-etilene |
| JPS62252736A (ja) * | 1986-04-24 | 1987-11-04 | Nippon Haron Kk | トリフルオロエチレンの製造方法 |
| FR2631858A1 (fr) * | 1988-05-24 | 1989-12-01 | Solvay | Compositions catalytiques, procede pour leur obtention et procede d'hydrogenation de chlorofluoralcenes au moyen de ces compositions |
| FR2635471A1 (fr) * | 1988-08-22 | 1990-02-23 | Solvay | Compositions catalytiques, procede pour leur obtention et procede d'hydrogenation de 1,1,2-trichloro-1,2,2-trifluorethane au moyen de ces compositions |
| US5283379A (en) * | 1990-08-13 | 1994-02-01 | F. Tech, Inc. | Method for producing trifluoroethylene |
| FR2668769B1 (fr) * | 1990-11-06 | 1992-12-31 | Atochem | Fabrication de fluoroethylenes et de chlorofluoroethylenes. |
| GB9107677D0 (en) * | 1991-04-11 | 1991-05-29 | Ici Plc | Chemical process |
| JP2003126692A (ja) * | 2001-10-30 | 2003-05-07 | Council Scient Ind Res | 活性の高い、改質カーボン担持パラジウム触媒の合成方法 |
| US6706658B2 (en) * | 2001-12-21 | 2004-03-16 | Engelhard Corporation | Catalyst for purification of aromatic acids |
| US7135601B2 (en) * | 2005-03-28 | 2006-11-14 | Honeywell International Inc. | Catalytic method for the production of fluoroalkylenes from chlorofluorohydrocarbons |
-
2011
- 2011-06-22 EP EP11727967.9A patent/EP2588434B1/fr active Active
- 2011-06-22 US US13/704,001 patent/US20130131402A1/en not_active Abandoned
- 2011-06-22 JP JP2013517185A patent/JP5964823B2/ja active Active
- 2011-06-22 RU RU2013104169/04A patent/RU2570812C2/ru active
- 2011-06-22 WO PCT/EP2011/060400 patent/WO2012000853A1/fr active Application Filing
- 2011-06-22 CN CN201180032991.6A patent/CN102971278B/zh active Active
-
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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| US3736265A (en) * | 1970-11-06 | 1973-05-29 | Texaco Inc | Stabilized palladium-carbon catalysts |
| US4399052A (en) * | 1980-12-22 | 1983-08-16 | Kabushiki Kaisha Kobe Seiko Sho | Activated carbonaceous honeycomb body and production method thereof |
| US5783514A (en) * | 1992-03-26 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Shell catalyst, a process for its production and its use |
| US6753290B1 (en) * | 1999-07-29 | 2004-06-22 | Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdelenia Rossiiskoi Akademii Nauk | Catalytic composition, method for manufacturing thereof and method for the purification of terephthalic acid |
| US6472343B1 (en) * | 2001-04-11 | 2002-10-29 | Westvaco Corporation | Shaped activated carbon |
| US6573212B2 (en) * | 2001-04-11 | 2003-06-03 | Meadwestvaco Corporation | Method of making shaped activated carbon |
| US6624109B2 (en) * | 2001-10-23 | 2003-09-23 | Council Of Scientific And Industrial Research | Process for the synthesis of highly active modified carbon supported palladium catalyst |
| US6815391B2 (en) * | 2002-04-30 | 2004-11-09 | Changchun Institute Of Applied Chemistry Chinese Academy Of Science | Method of preparing nano-level platinum/carbon electrocatalyst for cathode of fuel cell |
| US20060154810A1 (en) * | 2004-12-24 | 2006-07-13 | China Petrochemical Corporation | Hydrogenation catalyst, its preparation and use |
| US7622416B2 (en) * | 2004-12-24 | 2009-11-24 | China Petrochemical Corporation | Hydrogenation catalyst, its preparation and use |
| WO2012000853A1 (fr) * | 2010-07-01 | 2012-01-05 | Solvay Solexis S.P.A. | Procédé de synthèse de trifluoroéthylène |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9862660B2 (en) | 2014-02-20 | 2018-01-09 | Asahi Glass Company, Limited | Method for purifying fluid that includes trifluoroethylene, and method for producing trifluoroethylene |
| US20170144949A1 (en) * | 2014-08-25 | 2017-05-25 | Asahi Glass Company, Limited | Method for producing hydrofluoroolefin |
| 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 |
| US10781151B2 (en) | 2014-08-25 | 2020-09-22 | AGC Inc. | Process for producing hydrofluoroolefin |
| US10189758B2 (en) * | 2014-12-05 | 2019-01-29 | AGC Inc. | Method for producing hydrofluoroolefin |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102971278B (zh) | 2014-12-17 |
| JP5964823B2 (ja) | 2016-08-03 |
| RU2570812C2 (ru) | 2015-12-10 |
| EP2588434A1 (fr) | 2013-05-08 |
| US9403742B2 (en) | 2016-08-02 |
| EP2588434B1 (fr) | 2016-11-02 |
| US20160303543A1 (en) | 2016-10-20 |
| JP2013534529A (ja) | 2013-09-05 |
| WO2012000853A1 (fr) | 2012-01-05 |
| US20140303411A1 (en) | 2014-10-09 |
| RU2013104169A (ru) | 2014-08-10 |
| CN102971278A (zh) | 2013-03-13 |
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