JP5511178B2 - ハロゲン化アルカリ金属ドープ2価金属フッ化物の触媒組成物の製造方法及びフッ化オレフィンの製造方法 - Google Patents
ハロゲン化アルカリ金属ドープ2価金属フッ化物の触媒組成物の製造方法及びフッ化オレフィンの製造方法 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims description 49
- 239000000203 mixture Substances 0.000 title claims description 33
- 229910001512 metal fluoride Inorganic materials 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001336 alkenes Chemical class 0.000 title claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 title description 2
- 150000001340 alkali metals Chemical group 0.000 title description 2
- 150000008045 alkali metal halides Chemical class 0.000 claims description 41
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 19
- 239000002002 slurry Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- -1 halogen ion Chemical class 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 36
- 239000002904 solvent Substances 0.000 description 16
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910016509 CuF 2 Inorganic materials 0.000 description 1
- 229910015475 FeF 2 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
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- 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
-
- 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
- B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
-
- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- 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
- B01J27/08—Halides
-
- 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
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- 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
- B01J35/19—Catalysts containing parts with different compositions
-
- 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
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying
-
- 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
- B01J37/04—Mixing
-
- 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
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)
Description
低い地球温暖化係数を示すハイドロフルオロオレフィンである2,3,3,3−テトラフルオロプロペン(1234yf)は、例えば、冷媒、発泡剤、溶媒、洗浄剤、及び高分子化合物用モノマー等の、様々な用途に用いることができる。
MX/M’F2
により表すことができる、ハロゲン化アルカリ金属(単数又は複数)と2価金属フッ化物(単数又は複数)との配合物/混合物であり、式中、MXは、ハロゲン化アルカリ金属であり、Mは、Li+、Na+、K+、Rb+及びCs+からなる群から選択されるアルカリ金属イオンであり、Xは、F−、Cl−、Br−及びI−からなる群から選択されるハロゲンイオンであり、Xは好ましくは、F−及びCl−である。M’F2は、2価金属フッ化物であり、M’は、2価金属イオンであり、M’は好ましくは、Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Fe2+、Co2+、Cu2+及びZn2+からなる群から選択され、M’は最も好ましくは、Mg2+である。
n% MX/M’F2
により表すことができ、式中、n%は、組成物の全重量に基づく、組成物中におけるハロゲン化アルカリ金属の重量パーセントである。このハロゲン化アルカリ金属は、触媒組成物の全重量に基づき、触媒組成物の、好ましくは、約0.05重量%から約50重量%であり、より好ましくは、約5重量%から約15重量%であり、最も好ましくは、約7.5重量%から約12.5重量%である。
様々なCsCl添加量をもつ、一連のCsCl/MgF2触媒を試験して、CsCl添加量の反応性に対する効果を測定した。一般的に、触媒ペレットを20cc使用した。97.2%/2.0%の244bb/1233xfの混合物を、470℃から520℃の範囲の温度で、6g/h(グラム/時間)の速度で触媒床に通した。触媒床の下部及び上部の温度を測定した。以下の表2に示すように、活性は、添加量に関わらず、ほぼ同等の水準のままであったが、1233xf(所望の脱フッ化水素生成物でない)の選択率は、CsCl添加量が5.0重量%にまで上昇するにつれて減少した。10重量%のCsCl/MgF2触媒上では、1233xfは形成しなかった。
10重量%のKCl/MgF2及び10重量%のCsCl/MgF2の触媒を試験した。触媒ペレットを20cc使用した。99.1%/0.4%の244bb/1233xfの混合物を、380℃から480℃の範囲の温度で、6g/hの速度で触媒床に通した。触媒床の下部及び上部の温度を測定した。表3に示すように、両触媒は、ほぼ同等の活性(20%)を示したが、10重量%のCsCl/MgF2触媒は、触媒上で1233xfを生成することなく、1234yfのより高い選択率を与えた。
10重量%のCsCl/NiF2及び10重量%のCsCl/MgF2の触媒を試験した。触媒ペレットを20cc使用した。99.1%/0.4%の244bb/1233xfの混合物を、380℃から480℃の範囲の温度で、6g/hの速度で触媒床に通した。触媒床の下部及び上部の温度を測定した。表4に示すように、両触媒は、ほぼ同等の、1234yfの選択率(97%から98%)を示したが、10重量%のCsCl/MgF2触媒はより高い活性をもたらした。
実施例4においては、1234yfの選択率を向上させることを目的として、MgF2への添加剤として、一連の塩化アルカリ金属を調査した。比較の目的で、MgF2触媒上で得られた生成物も報告した。一般的な試験においては、触媒ペレットを20cc使用した。97.2%の244bb/2.0%の1233xfの混合物を、470℃から520℃の範囲の温度で、6g/h(グラム/時間)の速度で触媒床に通した。触媒床の下部、及び触媒床の上部の温度を測定した。
Claims (3)
- ハイドロクロロフルオロカーボンからのフッ化オレフィンの製造に使用するための触媒組成物の製造方法であって、
(a)ある量のアルカリ金属の水酸化物、酸化物又は炭酸塩をハロゲン化水素の水溶液に加え反応させて、ハロゲン化アルカリ金属の水溶液を形成するステップ;
(b)ある量の2価金属の水酸化物、酸化物又は炭酸塩をフッ化水素の水溶液に加え反応させて、2価金属フッ化物の沈殿を形成するステップ;
(c)前記ハロゲン化アルカリ金属溶液と前記2価金属フッ化物の沈殿とを混合して、水性スラリーを形成するステップ;及び
(d)前記水性スラリーから水を除去して、固形物を形成するステップ;
を含み、
前記ハロゲン化アルカリ金属は、式MXにより表され;Mは、Li+、Na+、K+、Rb+及びCs+からなる群から選択されるアルカリ金属イオンであり;Xは、F−、Cl−、Br−及びI−からなる群から選択されるハロゲンイオンであり;前記2価金属フッ化物は、式M’F2により表され;M’は、Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Fe2+、及びCo 2+ からなる群から選択される2価金属イオンである方法。 - 請求項1に記載の方法であって、MがK+及びCs+からなる群から選択され、XがF−及びCl−からなる群から選択され、そして、M’がMg2+及びNi2+からなる群から選択される方法。
- フッ化オレフィンの製造方法であって、
触媒的に有効な量の、請求項1又は2で定義した方法による触媒組成物の存在下で、隣り合う炭素上に少なくとも1個の水素と少なくとも1個の塩素とを有するハイドロクロロフルオロカーボンを脱塩化水素するステップを含む方法。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1256607P | 2007-12-10 | 2007-12-10 | |
US61/012,566 | 2007-12-10 | ||
US12/275,656 US8119557B2 (en) | 2007-12-10 | 2008-11-21 | Method for making catalyst compositions of alkali metal halide-doped bivalent metal fluorides and process for making fluorinated olefins |
US12/275,656 | 2008-11-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009166033A JP2009166033A (ja) | 2009-07-30 |
JP5511178B2 true JP5511178B2 (ja) | 2014-06-04 |
Family
ID=40722328
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008313374A Active JP5511178B2 (ja) | 2007-12-10 | 2008-12-09 | ハロゲン化アルカリ金属ドープ2価金属フッ化物の触媒組成物の製造方法及びフッ化オレフィンの製造方法 |
Country Status (7)
Country | Link |
---|---|
US (3) | US8119557B2 (ja) |
EP (2) | EP3112024A1 (ja) |
JP (1) | JP5511178B2 (ja) |
KR (1) | KR101509465B1 (ja) |
CN (2) | CN103351273B (ja) |
ES (2) | ES2638075T3 (ja) |
MX (1) | MX2008015692A (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
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US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
US8846990B2 (en) | 2007-07-06 | 2014-09-30 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
EP2271725B1 (en) | 2008-05-07 | 2018-02-21 | The Chemours Company FC, LLC | Compositions comprising 2,3,3,3-tetrafluoropropene and 1,1,1-trifluoropropene |
US8053612B2 (en) * | 2008-05-30 | 2011-11-08 | Honeywell International Inc. | Process for dehydrochlorinating 1,1,1,2-tetrafluoro-2-chloropropane to 2,3,3,3-tetrafluoropropene in the presence of an alkali metal-doped magnesium oxyfluoride catalyst and methods for making the catalyst |
US8203022B2 (en) | 2008-10-27 | 2012-06-19 | E I Du Pont De Nemours And Company | Conversion of 2-chloro-1,1,1,2-tetrafluoropropane to 2,3,3,3-tetrafluoropropene |
US8697922B2 (en) | 2008-10-27 | 2014-04-15 | E I Du Pont De Nemours And Company | Conversion of 2-chloro-1,1,1,2-tetrafluoropropane to 2,3,3,3-tetrafluoropropene |
JP5946821B2 (ja) * | 2010-04-02 | 2016-07-06 | ソルヴェイ(ソシエテ アノニム) | ヒドロクロロフルオロアルカン類の脱塩化水素方法 |
US8263817B2 (en) | 2010-07-06 | 2012-09-11 | E I Du Pont De Nemours And Company | Synthesis of 1234YF by selective dehydrochlorination of 244BB |
US8884083B2 (en) * | 2011-02-21 | 2014-11-11 | E. I. Du Pont De Nemours And Company | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
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CN101468323A (zh) | 2009-07-01 |
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US20110282111A1 (en) | 2011-11-17 |
US8119557B2 (en) | 2012-02-21 |
US8648222B2 (en) | 2014-02-11 |
JP2009166033A (ja) | 2009-07-30 |
CN103351273A (zh) | 2013-10-16 |
MX2008015692A (es) | 2009-06-16 |
EP2589432B1 (en) | 2017-05-24 |
CN103351273B (zh) | 2018-08-03 |
US20090149680A1 (en) | 2009-06-11 |
KR20090060955A (ko) | 2009-06-15 |
US20140113805A1 (en) | 2014-04-24 |
EP3112024A1 (en) | 2017-01-04 |
KR101509465B1 (ko) | 2015-04-06 |
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