JP2014513673A - ヒドロクロロフルオロカーボンの触媒接触脱塩化水素化 - Google Patents
ヒドロクロロフルオロカーボンの触媒接触脱塩化水素化 Download PDFInfo
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- 238000007033 dehydrochlorination reaction Methods 0.000 title claims abstract description 32
- 230000003197 catalytic effect Effects 0.000 title description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000003054 catalyst Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 52
- 230000008569 process Effects 0.000 claims abstract description 44
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims description 16
- 238000010926 purge Methods 0.000 claims description 16
- 239000000047 product Substances 0.000 description 22
- 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 19
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 17
- 239000007858 starting material Substances 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 11
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 9
- 229910001508 alkali metal halide Inorganic materials 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- -1 alkali metal halide salt Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000008246 gaseous mixture Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000003507 refrigerant Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WHPKSWFREPSUCO-UHFFFAOYSA-N 1,2-dichloro-1,2,3,3-tetrafluoropropane Chemical compound FC(F)C(F)(Cl)C(F)Cl WHPKSWFREPSUCO-UHFFFAOYSA-N 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 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 3
- 238000010792 warming Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical group 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- 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
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
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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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
以下の実施例において本明細書に記載した概念をさらに説明するが、これらは、特許請求の範囲に記載した本発明の範囲を限定するものではない。
表面積が約1200から約1500m2/gの範囲にある活性炭を、1wt%のHNO3水溶液に室温で12時間浸漬させ、その後、脱イオン水で十分に洗浄し、120℃で12時間乾燥させた。上記で調製したHNO3洗浄済み活性炭のいくらかにKFを付加させ、実施例1で使用し、いくらかにKClを付加させ、実施例2および3で使用した。
表面積が約1000m2/gから約1200m2/gの範囲にあるTakeda(商標)活性炭を、1wt%のHNO3水溶液に室温で12時間浸漬させ、その後、脱イオン水で十分に洗浄し、120℃で12時間乾燥させた。次いで、HNO3洗浄済みTakeda(商標)カーボンにKClを付加させ、実施例4および5で使用した。
表面積が約1000m2/gから約1200m2/gの範囲にあるTakeda(商標)活性炭を、8wt%のHNO3水溶液に60℃で12時間浸漬させ、その後、脱イオン水で十分に洗浄し、120℃で12時間乾燥させた。次いで、上記で調製したTakeda(商標)カーボンにKClを付加させ、実施例7で使用した。
Claims (12)
- 脱塩化水素化プロセスであって、
反応域においてRfCFClCH2Xを触媒と接触させて、RfCF=CHXを含む生成混合物を生成させるステップを含み、
前記触媒は、カーボンに担持されたMYを含み、
式中、
Rfは、過フッ化アルキル基であり、
Xは、H、F、Cl、Br、またはI、
Mは、K、Na、またはCs、および
Yは、F、Cl、またはBr、
であることを特徴とするプロセス。 - 前記カーボンは活性炭であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記カーボンは酸洗浄した活性炭であることを特徴とする請求項2に記載の脱塩化水素化プロセス。
- MはKであり、YはFまたはClであることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記反応域の温度は約200℃から約500℃であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記反応域の温度は約320℃から約380℃であることを特徴とする請求項5に記載の脱塩化水素化プロセス。
- RfCF=CHXに対する生成物選択性は少なくとも90モル%であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- RfCF=CHXに対する生成物選択性は少なくとも96モル%であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- RfCFClCH2XはCF3CFClCH2Clであり、RfCF=CHXはCF3CF=CHClであることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- RfCFClCH2XはCF3CFClCH3であり、RfCF=CHXはCF3CF=CH2であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記触媒を不活性ガスでパージするステップをさらに含むことを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記不活性ガスはN2であることを特徴とする請求項11に記載の脱塩化水素化プロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161444879P | 2011-02-21 | 2011-02-21 | |
US61/444,879 | 2011-02-21 | ||
PCT/US2012/025871 WO2012115930A1 (en) | 2011-02-21 | 2012-02-21 | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
Publications (2)
Publication Number | Publication Date |
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JP2014513673A true JP2014513673A (ja) | 2014-06-05 |
JP5926295B2 JP5926295B2 (ja) | 2016-05-25 |
Family
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JP2013555479A Active JP5926295B2 (ja) | 2011-02-21 | 2012-02-21 | ヒドロクロロフルオロカーボンの触媒接触脱塩化水素化 |
Country Status (8)
Country | Link |
---|---|
US (1) | US9012702B2 (ja) |
EP (1) | EP2678298B1 (ja) |
JP (1) | JP5926295B2 (ja) |
KR (2) | KR102026045B1 (ja) |
CN (1) | CN103370292B (ja) |
MX (1) | MX2013009580A (ja) |
TW (1) | TW201235333A (ja) |
WO (1) | WO2012115930A1 (ja) |
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JP2015105340A (ja) * | 2013-11-29 | 2015-06-08 | 旭硝子株式会社 | 硬質発泡合成樹脂およびその製造方法 |
WO2017002925A1 (ja) * | 2015-06-30 | 2017-01-05 | 旭硝子株式会社 | ヒドロクロロフルオロオレフィンの製造方法、および2,3,3,3-テトラフルオロプロペンの製造方法 |
WO2017110851A1 (ja) * | 2015-12-25 | 2017-06-29 | 旭硝子株式会社 | 1-クロロ-2,3,3,3-テトラフルオロプロペンの製造方法 |
WO2017146190A1 (ja) * | 2016-02-26 | 2017-08-31 | 旭硝子株式会社 | 精製1-クロロ-2,3,3,3-テトラフルオロプロペンおよび精製1-クロロ-2,3,3,3-テトラフルオロプロペン(z)の製造方法 |
WO2019098337A1 (ja) * | 2017-11-20 | 2019-05-23 | Agc株式会社 | (z)-1-クロロ-2,3,3,3-テトラフルオロプロペンの精製方法 |
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US8884082B2 (en) | 2011-02-21 | 2014-11-11 | E. I. Du Pont De Nemours And Company | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
US8884083B2 (en) | 2011-02-21 | 2014-11-11 | E. I. Du Pont De Nemours And Company | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
US9724684B2 (en) | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
WO2012157763A1 (ja) * | 2011-05-19 | 2012-11-22 | 旭硝子株式会社 | 作動媒体および熱サイクルシステム |
US8796493B2 (en) * | 2011-09-30 | 2014-08-05 | Honeywell International Inc. | Methods to separate halogentated olefins from 2-chloro-1,1,1,2-tetrafluoropropane using a solid adsorbent |
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US20120215037A1 (en) | 2012-08-23 |
MX2013009580A (es) | 2013-09-06 |
WO2012115930A1 (en) | 2012-08-30 |
KR20180121668A (ko) | 2018-11-07 |
US9012702B2 (en) | 2015-04-21 |
TW201235333A (en) | 2012-09-01 |
CN103370292A (zh) | 2013-10-23 |
CN103370292B (zh) | 2016-08-17 |
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KR101914182B1 (ko) | 2018-11-02 |
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