KR101351802B1 - 플루오르화 유기 화합물 제조방법 - Google Patents
플루오르화 유기 화합물 제조방법 Download PDFInfo
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- KR101351802B1 KR101351802B1 KR1020087012086A KR20087012086A KR101351802B1 KR 101351802 B1 KR101351802 B1 KR 101351802B1 KR 1020087012086 A KR1020087012086 A KR 1020087012086A KR 20087012086 A KR20087012086 A KR 20087012086A KR 101351802 B1 KR101351802 B1 KR 101351802B1
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- South Korea
- Prior art keywords
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- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000004812 organic fluorine compounds Chemical class 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 32
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 83
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 41
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 36
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical group FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 17
- 230000009467 reduction Effects 0.000 claims description 14
- 239000007791 liquid phase Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims description 7
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- XTRPJEPJFXGYCI-UHFFFAOYSA-N 3-chloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)CCl XTRPJEPJFXGYCI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- GDPWRLVSJWKGPJ-UPHRSURJSA-N (z)-1-chloro-2,3,3,3-tetrafluoroprop-1-ene Chemical compound Cl\C=C(/F)C(F)(F)F GDPWRLVSJWKGPJ-UPHRSURJSA-N 0.000 claims 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 4
- 230000000996 additive effect Effects 0.000 abstract description 4
- 239000011737 fluorine Substances 0.000 abstract description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 27
- 239000007789 gas Substances 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 8
- 238000010574 gas phase reaction Methods 0.000 description 8
- 229910000792 Monel Inorganic materials 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 230000003466 anti-cipated effect Effects 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- 229910000856 hastalloy Inorganic materials 0.000 description 4
- 229910001026 inconel Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- -1 heat transfer media Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 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
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 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 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229940074869 marquis Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- VBUNOIXRZNJNAD-UHFFFAOYSA-N ponazuril Chemical compound CC1=CC(N2C(N(C)C(=O)NC2=O)=O)=CC=C1OC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 VBUNOIXRZNJNAD-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- 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
Landscapes
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73337805P | 2005-11-03 | 2005-11-03 | |
| US60/733,378 | 2005-11-03 | ||
| PCT/US2006/042936 WO2007056128A1 (en) | 2005-11-03 | 2006-11-03 | Method for producing fluorinated organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20080064878A KR20080064878A (ko) | 2008-07-09 |
| KR101351802B1 true KR101351802B1 (ko) | 2014-01-15 |
Family
ID=37866036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087012086A Active KR101351802B1 (ko) | 2005-11-03 | 2006-11-03 | 플루오르화 유기 화합물 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP1954661B1 (enExample) |
| JP (1) | JP5592607B2 (enExample) |
| KR (1) | KR101351802B1 (enExample) |
| CN (1) | CN101356143A (enExample) |
| CA (1) | CA2628446C (enExample) |
| ES (1) | ES2611052T3 (enExample) |
| RU (1) | RU2425822C2 (enExample) |
| WO (1) | WO2007056128A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9102579B2 (en) | 2004-04-29 | 2015-08-11 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CA2635806C (en) * | 2006-01-03 | 2015-03-31 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| GB0806422D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| TW200837036A (en) * | 2006-11-15 | 2008-09-16 | Du Pont | Process for producing 2,3,3,3-tetrafluoropropene |
| GB0625214D0 (en) | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| US7884254B2 (en) * | 2007-08-08 | 2011-02-08 | Honeywell International Inc. | Dehydrochlorination of hydrochlorofluorocarbons using pre-treated activated carbon catalysts |
| ES2400365T3 (es) | 2007-12-27 | 2013-04-09 | Arkema France | Procedimiento para la producción de 1,1,1,2-tetrafluorpropeno |
| GB0806389D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0806419D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| KR100985565B1 (ko) | 2008-07-04 | 2010-10-05 | 삼성전기주식회사 | 시스템 인 패키지 모듈 및 이를 구비하는 휴대용 단말기 |
| SI3581631T1 (sl) * | 2009-12-22 | 2025-04-30 | The Chemours Company Fc, Llc | Sestavki, ki obsegajo 2,3,3,3-tetrafluoropropen |
| ES2535266T3 (es) * | 2010-04-19 | 2015-05-07 | Holt Lloyd International Limited | Sellador para neumáticos y composición insuflante |
| US9000241B2 (en) | 2010-11-02 | 2015-04-07 | E. I. Du Pont De Nemours And Company | Use of copper-nickel catalysts for dehlogenation of chlorofluorocompounds |
| RU2476417C1 (ru) * | 2011-10-20 | 2013-02-27 | Ильдар Айдарович Султангузин | Способ получения 2,3,3,3-тетрафторпропилена и 1,3,3,3-тетрафторпропилена |
| FR3000096B1 (fr) * | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| 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 |
| JP6610625B2 (ja) * | 2017-07-31 | 2019-11-27 | ダイキン工業株式会社 | １，２−ジクロロ−１，２−ジフルオロエタン（ＨＣＦＣ−１３２）の製造方法、１−クロロ−１，２−ジフルオロエチレン（ＨＣＦＯ−１１２２ａ）の製造方法、及びＨＣＦＣ−１３２の分離方法 |
| US10696613B1 (en) * | 2019-07-09 | 2020-06-30 | Honeywell International Inc. | Gas phase process for chlorotrifluoroethylene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998042645A1 (en) * | 1997-03-24 | 1998-10-01 | E.I. Du Pont De Nemours And Company | Addition of hydrofluorocarbons to fluoroolefins |
| US6700026B1 (en) * | 1992-11-11 | 2004-03-02 | Daikin Industries Ltd. | Method for preparing difluoromethane |
| WO2005042451A2 (en) * | 2003-10-27 | 2005-05-12 | Honeywell International Inc. | Process for producing fluoropropenes |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
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2006
- 2006-11-03 WO PCT/US2006/042936 patent/WO2007056128A1/en not_active Ceased
- 2006-11-03 ES ES06827435.6T patent/ES2611052T3/es active Active
- 2006-11-03 CN CNA2006800498307A patent/CN101356143A/zh active Pending
- 2006-11-03 EP EP06827435.6A patent/EP1954661B1/en active Active
- 2006-11-03 EP EP11156860.6A patent/EP2348007B1/en not_active Ceased
- 2006-11-03 RU RU2008122214/04A patent/RU2425822C2/ru active
- 2006-11-03 CA CA2628446A patent/CA2628446C/en active Active
- 2006-11-03 JP JP2008540087A patent/JP5592607B2/ja not_active Expired - Fee Related
- 2006-11-03 KR KR1020087012086A patent/KR101351802B1/ko active Active
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| US6700026B1 (en) * | 1992-11-11 | 2004-03-02 | Daikin Industries Ltd. | Method for preparing difluoromethane |
| WO1998042645A1 (en) * | 1997-03-24 | 1998-10-01 | E.I. Du Pont De Nemours And Company | Addition of hydrofluorocarbons to fluoroolefins |
| WO2005042451A2 (en) * | 2003-10-27 | 2005-05-12 | Honeywell International Inc. | Process for producing fluoropropenes |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101356143A (zh) | 2009-01-28 |
| ES2611052T3 (es) | 2017-05-04 |
| KR20080064878A (ko) | 2008-07-09 |
| RU2008122214A (ru) | 2009-12-10 |
| EP2348007B1 (en) | 2018-10-17 |
| EP1954661A1 (en) | 2008-08-13 |
| CA2628446C (en) | 2017-01-24 |
| EP1954661B1 (en) | 2016-10-19 |
| JP5592607B2 (ja) | 2014-09-17 |
| JP2009518288A (ja) | 2009-05-07 |
| EP2348007A1 (en) | 2011-07-27 |
| RU2425822C2 (ru) | 2011-08-10 |
| WO2007056128A1 (en) | 2007-05-18 |
| CA2628446A1 (en) | 2007-05-18 |
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