JP7483077B2 - より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 - Google Patents
より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 Download PDFInfo
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- JP7483077B2 JP7483077B2 JP2023024987A JP2023024987A JP7483077B2 JP 7483077 B2 JP7483077 B2 JP 7483077B2 JP 2023024987 A JP2023024987 A JP 2023024987A JP 2023024987 A JP2023024987 A JP 2023024987A JP 7483077 B2 JP7483077 B2 JP 7483077B2
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- 238000006243 chemical reaction Methods 0.000 title description 21
- BLEZTPDKUBSTII-UHFFFAOYSA-N 1-chloro-1-fluoroprop-1-ene Chemical class CC=C(F)Cl BLEZTPDKUBSTII-UHFFFAOYSA-N 0.000 title description 2
- OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical class CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 title description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- UJIGKESMIPTWJH-UHFFFAOYSA-N 1,3-dichloro-1,1,2,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)Cl UJIGKESMIPTWJH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 47
- 238000005984 hydrogenation reaction Methods 0.000 description 39
- 239000003054 catalyst Substances 0.000 description 38
- 239000007795 chemical reaction product Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 23
- 239000000543 intermediate Substances 0.000 description 21
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 15
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 229910018054 Ni-Cu Inorganic materials 0.000 description 9
- 229910018481 Ni—Cu Inorganic materials 0.000 description 9
- 229910002528 Cu-Pd Inorganic materials 0.000 description 7
- JYNCTFQDWJMJDI-UHFFFAOYSA-N 2-chloro-1,1,1,3,3-pentafluoropropane Chemical compound FC(F)C(Cl)C(F)(F)F JYNCTFQDWJMJDI-UHFFFAOYSA-N 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 229910000856 hastalloy Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- CNNJBYUJTYGLGG-UHFFFAOYSA-N 2-chloro-1,1,1,3-tetrafluoropropane Chemical compound FCC(Cl)C(F)(F)F CNNJBYUJTYGLGG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- QGYLHZMNVGBXDQ-UHFFFAOYSA-N 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene Chemical compound ClC(Cl)=C(F)C(F)(F)F QGYLHZMNVGBXDQ-UHFFFAOYSA-N 0.000 description 1
- GDPWRLVSJWKGPJ-UHFFFAOYSA-N 1-chloro-2,3,3,3-tetrafluoroprop-1-ene Chemical compound ClC=C(F)C(F)(F)F GDPWRLVSJWKGPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910002668 Pd-Cu Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- 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
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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
-
- 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
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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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)
- Catalysts (AREA)
Description
10ccの10% Cu/Cを1.3cm(1/2インチ)のハステロイ(登録商標)C227反応容器に入れる。触媒は、250℃でH2を用いて4時間還元する。次いで、HCFC-225ca(HCFC-225ca反応混合物のGC分析は、表1にある)を、3.11sccmでH2(10.5sccm)と共に325℃及び350℃で大気圧で送り込む。反応容器からの反応生成物気流は、GC及びGC-MSによって分析される。水素化反応の結果を、表2に示す。HFO-1234yf、HCFO-1224yd、及びHCFC-235cbは、本反応で生成された反応生成物である。
10ccの0.5%Pd-8.5% % Cu/Cを1.3cm(1/2インチ)のハステロイ(登録商標)C227反応容器に入れる。触媒は、400℃でH2を用いて4時間還元する。次いで、225ca/cb混合物(HCFC-225ca反応混合物のGC分析は、表1にある)を、3.11sccmでH2(10.5sccm)と共に125、140、及び160℃で大気圧で送り込む。反応容器からの気流は、GC及びGC-MSによって分析される。試験結果を、表3に示す。HFO-1234yf、CFO-1224yd、及びHCFC-235cbは、本反応で生成される。
10ccの10% Cu/Cを1.3cm(1/2インチ)のハステロイ(登録商標)C227反応容器に入れる。触媒は、250℃でH2を用いて4時間還元する。次いで、235cbを3.5sccmでH2(6sccm)と共に325C及び350Cで大気圧で送り込んだ。反応容器からの気流は、GC及びGC-MSによって分析される。試験結果を、表4に示す。235cbは、88~90%の選択性で1234yfに変換される。
10ccのJohnson Matthey CP447 Ni-Cu/Cを1.3cm(1/2インチ)のハステロイ(登録商標)C227反応容器に入れる。触媒は、400℃でH2を用いて4時間還元する。次いで、225ca(混合物のGC分析は、表5にある)を、3.11sccmでH2(11sccm)と共に225、250、275、及び300Cで大気圧で送り込む。反応容器からの気流は、GC及びGC-MSによって分析される。試験結果を、表6に示す。1234yf、1224yd、及び235cbは、本反応で生成される。
10ccのJohnson Matthey CP447 Ni-Cu/Cを1.3cm(1/2インチ)のハステロイ(登録商標)C227反応容器に入れる。触媒は、400℃でH2を用いて4時間還元する。次いで、1214yaを、3.11sccmでH2(11sccm)と共に225、250、275、及び300℃で大気圧で送り込む。反応容器からの気流は、GC及びGC-MSによって分析される。1234yf及び1224ydは、表7に示すように、本反応において生成する。
Claims (2)
- HCFO-1224yd(CF3CF=CHCl)、HFO-1234yf(CF3CF=CH2)、HCFC-235cb(CF3CF2CH2Cl)、HCFC-225ca(CF3CF2CHCl2)、及びHCFO-1224xe (CF 3 CCl=CHF)を含む組成物。
- さらに、HCFC-225aa (CF3CCl2CHF2) 及びHCFC-225cb (CF2ClCF2CHClF)のうちの少なくとも一種を含む、請求項1に記載の組成物。
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US201461980157P | 2014-04-16 | 2014-04-16 | |
US61/980,157 | 2014-04-16 | ||
JP2020048611A JP6916335B2 (ja) | 2014-04-16 | 2020-03-19 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2021117193A JP7233484B2 (ja) | 2014-04-16 | 2021-07-15 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
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JP2016563075A Active JP6680692B2 (ja) | 2014-04-16 | 2015-04-03 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2020048611A Active JP6916335B2 (ja) | 2014-04-16 | 2020-03-19 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2021117194A Active JP7233485B2 (ja) | 2014-04-16 | 2021-07-15 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2021117193A Active JP7233484B2 (ja) | 2014-04-16 | 2021-07-15 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2023024987A Active JP7483077B2 (ja) | 2014-04-16 | 2023-02-21 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2023024990A Active JP7443588B2 (ja) | 2014-04-16 | 2023-02-21 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2024024555A Pending JP2024050992A (ja) | 2014-04-16 | 2024-02-21 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
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JP2020048611A Active JP6916335B2 (ja) | 2014-04-16 | 2020-03-19 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2021117194A Active JP7233485B2 (ja) | 2014-04-16 | 2021-07-15 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
JP2021117193A Active JP7233484B2 (ja) | 2014-04-16 | 2021-07-15 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
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JP2024024555A Pending JP2024050992A (ja) | 2014-04-16 | 2024-02-21 | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
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US (7) | US9637429B2 (ja) |
JP (7) | JP6680692B2 (ja) |
CN (2) | CN106573857B (ja) |
WO (1) | WO2015160532A1 (ja) |
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US9054449B2 (en) | 2012-01-27 | 2015-06-09 | Chatsworth Products, Inc. | Cable retention system for power distribution unit |
CN106573857B (zh) | 2014-04-16 | 2020-06-09 | 科慕埃弗西有限公司 | 将氯氟丙烷和氯氟丙烯转化成更需要的氟丙烷和氟丙烯 |
WO2016031777A1 (ja) | 2014-08-25 | 2016-03-03 | 旭硝子株式会社 | ハイドロフルオロオレフィンの製造方法 |
WO2017105840A1 (en) | 2015-12-14 | 2017-06-22 | Chatsworth Products, Inc. | Cage nut fastener and methods for tool-less installation of same |
WO2017146189A1 (ja) * | 2016-02-25 | 2017-08-31 | 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 |
JP6881457B2 (ja) * | 2016-08-09 | 2021-06-02 | Agc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 |
WO2018123911A1 (ja) * | 2016-12-28 | 2018-07-05 | 旭硝子株式会社 | 含塩素プロペンの製造方法 |
CN107759440B (zh) * | 2017-11-07 | 2020-07-03 | 中国民航大学 | 一种将含氟烯烃双键上的氟置换成氢的方法 |
US10547145B2 (en) | 2018-02-05 | 2020-01-28 | Chatworth Products, Inc. | Electric receptacle with locking feature |
JP7287391B2 (ja) * | 2018-05-28 | 2023-06-06 | Agc株式会社 | 含フッ素プロペンの製造方法 |
WO2020213600A1 (ja) * | 2019-04-16 | 2020-10-22 | Agc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 |
JP7511113B2 (ja) | 2019-09-06 | 2024-07-05 | Agc株式会社 | ハイドロフルオロオレフィンの製造方法 |
US11909154B1 (en) | 2021-03-08 | 2024-02-20 | Chatsworth Products, Inc. | Endcap for establishing electrical bonding connection |
CN112811978B (zh) * | 2021-04-22 | 2021-07-16 | 泉州宇极新材料科技有限公司 | Z-1,3,3,3-四氟丙烯的制备方法 |
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