CA2692520A1 - Preparation of halogen and hydrogen containing alkenes over metal fluoride catalysts - Google Patents
Preparation of halogen and hydrogen containing alkenes over metal fluoride catalysts Download PDFInfo
- Publication number
- CA2692520A1 CA2692520A1 CA 2692520 CA2692520A CA2692520A1 CA 2692520 A1 CA2692520 A1 CA 2692520A1 CA 2692520 CA2692520 CA 2692520 CA 2692520 A CA2692520 A CA 2692520A CA 2692520 A1 CA2692520 A1 CA 2692520A1
- Authority
- CA
- Canada
- Prior art keywords
- metal
- fluoride
- support
- dehydrofluorination
- supported
- 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
- 229910001512 metal fluoride Inorganic materials 0.000 title claims abstract description 53
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 22
- 239000003054 catalyst Substances 0.000 title claims description 84
- 238000002360 preparation method Methods 0.000 title claims description 17
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- 150000002367 halogens Chemical class 0.000 title claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title description 5
- 239000001257 hydrogen Substances 0.000 title description 5
- 229910052739 hydrogen Inorganic materials 0.000 title description 5
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims abstract description 59
- 238000005796 dehydrofluorination reaction Methods 0.000 claims abstract description 55
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 17
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims abstract description 8
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 claims abstract description 6
- FWTUDISDSYABRU-UHFFFAOYSA-N 1,1,2-trifluorobuta-1,3-diene Chemical compound FC(F)=C(F)C=C FWTUDISDSYABRU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 35
- 239000002243 precursor Substances 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 239000005300 metallic glass Substances 0.000 claims description 21
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 20
- 239000011261 inert gas Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 claims description 16
- -1 oxy fluoride Chemical compound 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 14
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 13
- 239000004411 aluminium Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000012025 fluorinating agent Substances 0.000 claims description 9
- 150000004703 alkoxides Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- JTGATPUEEONCSG-UHFFFAOYSA-N 1,1,3-trifluorobuta-1,3-diene Chemical compound FC(F)=CC(F)=C JTGATPUEEONCSG-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 238000006317 isomerization reaction Methods 0.000 claims description 6
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 6
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims description 5
- DKSYJUPLFVFPRY-UHFFFAOYSA-N 2,4,4,4-tetrafluorobut-1-ene Chemical compound FC(=C)CC(F)(F)F DKSYJUPLFVFPRY-UHFFFAOYSA-N 0.000 claims description 5
- VSPVOSOCAZPIJQ-IHWYPQMZSA-N (z)-1,1,1,3-tetrafluorobut-2-ene Chemical class C\C(F)=C\C(F)(F)F VSPVOSOCAZPIJQ-IHWYPQMZSA-N 0.000 claims description 4
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 claims description 3
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 claims description 3
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 claims description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims 2
- 125000000962 organic group Chemical group 0.000 claims 2
- HILNUELUDBMBJQ-UHFFFAOYSA-N 1-chloro-1,1,2-trifluoroethane Chemical compound FCC(F)(F)Cl HILNUELUDBMBJQ-UHFFFAOYSA-N 0.000 claims 1
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims 1
- BNLLWAALHYCOQM-UHFFFAOYSA-N 3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)C(F)(F)C=C BNLLWAALHYCOQM-UHFFFAOYSA-N 0.000 claims 1
- SOPMTTFVKDXVEM-UHFFFAOYSA-N 3-chloro-1,1,1,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)C(F)(F)F SOPMTTFVKDXVEM-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 229910052593 corundum Inorganic materials 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910001845 yogo sapphire Inorganic materials 0.000 claims 1
- 239000007789 gas Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 15
- 230000003197 catalytic effect Effects 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 150000001399 aluminium compounds Chemical class 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 238000011010 flushing procedure Methods 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052756 noble gas Inorganic materials 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 230000036632 reaction speed Effects 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011775 sodium fluoride Substances 0.000 description 3
- 235000013024 sodium fluoride Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- VSPVOSOCAZPIJQ-NSCUHMNNSA-N (e)-1,1,1,3-tetrafluorobut-2-ene Chemical compound C\C(F)=C/C(F)(F)F VSPVOSOCAZPIJQ-NSCUHMNNSA-N 0.000 description 2
- BSRRYOGYBQJAFP-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluorobutane Chemical compound CC(F)C(F)(F)C(F)(F)F BSRRYOGYBQJAFP-UHFFFAOYSA-N 0.000 description 2
- NVSXSBBVEDNGPY-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical compound CCC(F)(F)C(F)(F)F NVSXSBBVEDNGPY-UHFFFAOYSA-N 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 238000004438 BET method Methods 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000012494 Quartz wool Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000005675 difluoroethenyl group Chemical group [H]C(*)=C(F)F 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000000988 reflection electron microscopy Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 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
- CDOOAUSHHFGWSA-UPHRSURJSA-N (z)-1,3,3,3-tetrafluoroprop-1-ene Chemical group F\C=C/C(F)(F)F CDOOAUSHHFGWSA-UPHRSURJSA-N 0.000 description 1
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 1
- LKLFXAVIFCLZQS-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluorobutane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)F LKLFXAVIFCLZQS-UHFFFAOYSA-N 0.000 description 1
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 1
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- NUPBXTZOBYEVIR-UHFFFAOYSA-N 1,1,2,3,3,4,4-heptafluorobut-1-ene Chemical compound FC(F)C(F)(F)C(F)=C(F)F NUPBXTZOBYEVIR-UHFFFAOYSA-N 0.000 description 1
- BNYODXFAOQCIIO-UHFFFAOYSA-N 1,1,3,3-tetrafluoroprop-1-ene Chemical compound FC(F)C=C(F)F BNYODXFAOQCIIO-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- 229940051271 1,1-difluoroethane Drugs 0.000 description 1
- KTULQNFKNLFOHL-UHFFFAOYSA-N 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(F)(Br)C(F)(F)Br KTULQNFKNLFOHL-UHFFFAOYSA-N 0.000 description 1
- FWAQVJAOVDYHAF-UHFFFAOYSA-N 1-chloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)Cl FWAQVJAOVDYHAF-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VCRVQFFAKUROKA-UHFFFAOYSA-N 2,2-dibromo-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(Br)(Br)C(F)(F)F VCRVQFFAKUROKA-UHFFFAOYSA-N 0.000 description 1
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical group FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- 229910018085 Al-F Inorganic materials 0.000 description 1
- 229910018179 Al—F Inorganic materials 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical class [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000009997 thermal pre-treatment Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical class F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
-
- 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
-
- 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
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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07112445.7 | 2007-07-13 | ||
| EP07112446 | 2007-07-13 | ||
| EP07112445 | 2007-07-13 | ||
| EP07112446.5 | 2007-07-13 | ||
| PCT/EP2008/059112 WO2009010472A1 (en) | 2007-07-13 | 2008-07-11 | Preparation of halogen and hydrogen containing alkenes over metal fluoride catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2692520A1 true CA2692520A1 (en) | 2009-01-22 |
Family
ID=39683944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2692520 Abandoned CA2692520A1 (en) | 2007-07-13 | 2008-07-11 | Preparation of halogen and hydrogen containing alkenes over metal fluoride catalysts |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8338651B2 (ja) |
| EP (1) | EP2170788B1 (ja) |
| JP (1) | JP5722623B2 (ja) |
| KR (1) | KR20100043234A (ja) |
| CN (1) | CN101801894B (ja) |
| BR (1) | BRPI0813589A2 (ja) |
| CA (1) | CA2692520A1 (ja) |
| RU (1) | RU2010105051A (ja) |
| TW (1) | TW200920721A (ja) |
| WO (1) | WO2009010472A1 (ja) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9493384B2 (en) * | 2007-07-06 | 2016-11-15 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| EP2370385B1 (en) | 2008-11-25 | 2016-01-27 | Solvay Fluor GmbH | Process for the preparation of chlorofluoroalkenes |
| JP2012519741A (ja) | 2009-03-06 | 2012-08-30 | ゾルファイ フルーオル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 不飽和ヒドロフルオロカーボンの使用 |
| US8158549B2 (en) * | 2009-09-04 | 2012-04-17 | Honeywell International Inc. | Catalysts for fluoroolefins hydrogenation |
| CN102971279B (zh) * | 2010-04-02 | 2015-05-20 | 索尔维公司 | 用于对氢氯氟烷脱氟化氢的方法以及由此获得的产品 |
| 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 |
| FR2961203B1 (fr) | 2010-06-15 | 2012-06-15 | Arkema France | Procede de preparation de trifluoroethylene |
| EP2663373A2 (en) * | 2011-01-11 | 2013-11-20 | E.I. Du Pont De Nemours And Company | Methods of reducing flame propogation in systems with a flammable refrigerant |
| EP3854860A1 (en) * | 2011-05-19 | 2021-07-28 | Agc Inc. | Working medium and heat-cycle system |
| EP2549526A1 (en) | 2011-07-18 | 2013-01-23 | Solvay Sa | Process for the production of etched items using fluorosubstituted compounds |
| US8647493B2 (en) | 2012-07-26 | 2014-02-11 | Liquid Light, Inc. | Electrochemical co-production of chemicals employing the recycling of a hydrogen halide |
| US8641885B2 (en) | 2012-07-26 | 2014-02-04 | Liquid Light, Inc. | Multiphase electrochemical reduction of CO2 |
| US20130105304A1 (en) | 2012-07-26 | 2013-05-02 | Liquid Light, Inc. | System and High Surface Area Electrodes for the Electrochemical Reduction of Carbon Dioxide |
| US10329676B2 (en) | 2012-07-26 | 2019-06-25 | Avantium Knowledge Centre B.V. | Method and system for electrochemical reduction of carbon dioxide employing a gas diffusion electrode |
| US9175407B2 (en) | 2012-07-26 | 2015-11-03 | Liquid Light, Inc. | Integrated process for producing carboxylic acids from carbon dioxide |
| US20140206896A1 (en) | 2012-07-26 | 2014-07-24 | Liquid Light, Inc. | Method and System for Production of Oxalic Acid and Oxalic Acid Reduction Products |
| WO2014043651A2 (en) | 2012-09-14 | 2014-03-20 | Liquid Light, Inc. | High pressure electrochemical cell and process for the electrochemical reduction of carbon dioxide |
| CN103044190B (zh) * | 2012-12-21 | 2014-12-24 | 巨化集团技术中心 | 一种三氟乙烯的制备方法 |
| US9180433B2 (en) | 2013-03-14 | 2015-11-10 | Honeywell International, Inc. | Catalysts for 2-chloro-1,1,1,2-tetrafluoropropane dehydrochlorination |
| EP2993213B1 (en) * | 2013-04-30 | 2020-07-15 | AGC Inc. | Composition containing trifluoroethylene |
| WO2014178353A1 (ja) * | 2013-04-30 | 2014-11-06 | 旭硝子株式会社 | 熱サイクル用作動媒体 |
| JP6217749B2 (ja) * | 2013-06-28 | 2017-10-25 | 旭硝子株式会社 | トリフルオロエチレンの製造方法 |
| WO2014208452A1 (ja) * | 2013-06-28 | 2014-12-31 | 旭硝子株式会社 | トリフルオロエチレンの製造方法 |
| JP6432527B2 (ja) | 2014-01-30 | 2018-12-05 | Ａｇｃ株式会社 | トリフルオロエチレンの製造方法 |
| CN105939984B (zh) | 2014-01-30 | 2020-08-14 | Ａｇｃ株式会社 | 三氟乙烯的制造方法 |
| WO2015125874A1 (ja) * | 2014-02-20 | 2015-08-27 | 旭硝子株式会社 | 熱サイクル用作動媒体 |
| EP3109225B1 (en) * | 2014-02-20 | 2022-06-08 | AGC Inc. | Method for purifying fluid that includes trifluoroethylene, and method for producing trifluoroethylene |
| CN106164027B (zh) * | 2014-03-27 | 2018-04-17 | 旭硝子株式会社 | 三氟乙烯的制造方法 |
| CN110240535B (zh) | 2014-08-14 | 2022-09-13 | 科慕埃弗西有限公司 | 通过脱氟化氢来制备E-1,3,3,3-四氟丙烯(HFC-1234ze)的方法 |
| JP2016124847A (ja) * | 2015-01-07 | 2016-07-11 | 旭硝子株式会社 | トリフルオロエチレンの製造方法 |
| CN105251518B (zh) * | 2015-11-02 | 2017-09-08 | 西安近代化学研究所 | 一种1,1,1,2‑四氟乙烷制备三氟乙烯用催化剂 |
| CN107867997B (zh) * | 2016-09-28 | 2023-07-04 | 中化近代环保化工(西安)有限公司 | 一种制备二氟乙酰氟的方法 |
| CN110294704A (zh) * | 2018-03-24 | 2019-10-01 | 复旦大学 | 一种制备含单氟烷基烯烃化合物的方法 |
| CN113195442A (zh) * | 2018-12-19 | 2021-07-30 | 大金工业株式会社 | 氟代乙烷的制造方法和氟代烯烃的制造方法 |
| CN113195443A (zh) | 2018-12-19 | 2021-07-30 | 大金工业株式会社 | 氟代乙烷的制造方法和氟代烯烃的制造方法 |
| JP6966712B2 (ja) | 2019-01-25 | 2021-11-17 | ダイキン工業株式会社 | フルオロエタンの製造方法及びフルオロオレフィンの製造方法 |
| EP3919467A4 (en) | 2019-01-28 | 2022-11-02 | Daikin Industries, Ltd. | AZEOTROPIC COMPOSITION CONTAINING 1,2-DIFLUOROETHYLENE OR 1,1,2-TRIFLUOROETHYLENE AND HYDROGEN FLUORIDE |
| JP6933239B2 (ja) * | 2019-02-21 | 2021-09-08 | ダイキン工業株式会社 | ハロゲン化アルケン化合物及びフッ化アルキン化合物の製造方法 |
| CN110756201A (zh) * | 2019-06-16 | 2020-02-07 | 浙江工业大学 | 一种碳结构限域金属氟化物的制备方法 |
| TW202124344A (zh) * | 2019-09-12 | 2021-07-01 | 日商關東電化工業股份有限公司 | 具有＝ｃｆ或＝ｃｈｆ構造的氟烯烴之精製方法，及高純度氟烯烴以及其製造方法 |
| EP3954673A1 (en) * | 2020-08-14 | 2022-02-16 | Paul Scherrer Institut | A method for preparing surface fluorinated battery materials |
| CN111905779B (zh) * | 2020-08-27 | 2022-11-11 | 浙江工业大学 | 一种多元金属氟化物复合型催化剂及其制备方法和应用 |
| WO2024057657A1 (ja) * | 2022-09-16 | 2024-03-21 | Ａｇｃ株式会社 | フルオロオレフィンの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673139A (en) * | 1951-08-03 | 1954-03-23 | Allied Chem & Dye Corp | Manufacture of aluminum fluoride catalyst |
| US3941874A (en) | 1973-02-26 | 1976-03-02 | Anaconda Aluminum Co. | Recovery of aluminum fluoride |
| EP0234002B1 (en) | 1986-01-22 | 1991-01-09 | ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.) | Process for converting a 1,1,1-trifluoroalkane into a 1,1-difluoroalkene |
| US4902838A (en) * | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| FR2710054A1 (fr) | 1993-09-16 | 1995-03-24 | Atochem Elf Sa | Procédé de préparation du trifluoroéthylène. |
| US5559069A (en) | 1994-05-26 | 1996-09-24 | E. I. Du Pont De Nemours And Company | Catalysts for halogenated hydrocarbon processing, their precursors and their preparation and use |
| EP0775100B1 (en) * | 1994-08-08 | 2000-11-08 | Imperial Chemical Industries Plc | Process for the production of trifluoroethylene |
| DE59703604D1 (de) * | 1996-06-26 | 2001-06-28 | Cs Clean Systems Ag | Verfahren zur entfernung ozonabbauender und/oder klimawirksamer fluorierter verbindungen aus einem gasstrom sowie anwendung des verfahrens |
| US5880315A (en) | 1996-11-21 | 1999-03-09 | E. I. Du Pont De Nemours And Company | Catalytic manufacture of vinyl fluoride |
| WO1998022414A1 (en) | 1996-11-21 | 1998-05-28 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of vinyl fluoride |
| US5945573A (en) * | 1997-01-31 | 1999-08-31 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
| WO1998033755A1 (en) * | 1997-01-31 | 1998-08-06 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of pentafluoropropenes |
| EP1440939A1 (en) * | 2003-01-07 | 2004-07-28 | Humboldt-Universität zu Berlin | Method for the preparation of amorphous metal fluorides |
| JP2006514913A (ja) * | 2003-01-07 | 2006-05-18 | フンボルト−ウニベルシテート・ツ・ベルリン | 高表面積金属フッ化物の製造方法 |
| US20050119512A1 (en) * | 2003-04-29 | 2005-06-02 | Central Glass Company, Limited | Fluorobutene derivatives and process for producing same |
| US7091388B2 (en) | 2003-09-26 | 2006-08-15 | Honeywell International Inc. | Method of making 1,1,3,3,3-pentafluoropropene |
| EP1586542A1 (en) | 2004-04-05 | 2005-10-19 | Humboldt-Universität zu Berlin | Method for the preparation of fluoride glass gel and use thereof |
| EP1666411A1 (en) * | 2004-12-03 | 2006-06-07 | Humboldt-Universität zu Berlin | Method for the preparation of X-ray amorphous or weakly crystalline metal oxide fluorides and new uses thereof |
| WO2010055146A2 (en) | 2008-11-13 | 2010-05-20 | Solvay Fluor Gmbh | Hydrofluoroolefins, manufacture of hydrofluoroolefins and methods of using hydrofluoroolefins |
| EP2370385B1 (en) | 2008-11-25 | 2016-01-27 | Solvay Fluor GmbH | Process for the preparation of chlorofluoroalkenes |
| CN102971279B (zh) | 2010-04-02 | 2015-05-20 | 索尔维公司 | 用于对氢氯氟烷脱氟化氢的方法以及由此获得的产品 |
| 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 |
-
2008
- 2008-07-10 TW TW097126091A patent/TW200920721A/zh unknown
- 2008-07-11 CA CA 2692520 patent/CA2692520A1/en not_active Abandoned
- 2008-07-11 US US12/668,568 patent/US8338651B2/en not_active Expired - Fee Related
- 2008-07-11 JP JP2010515525A patent/JP5722623B2/ja active Active
- 2008-07-11 EP EP08775029.5A patent/EP2170788B1/en not_active Not-in-force
- 2008-07-11 RU RU2010105051/04A patent/RU2010105051A/ru not_active Application Discontinuation
- 2008-07-11 KR KR1020107003262A patent/KR20100043234A/ko not_active Application Discontinuation
- 2008-07-11 WO PCT/EP2008/059112 patent/WO2009010472A1/en active Application Filing
- 2008-07-11 BR BRPI0813589-4A2A patent/BRPI0813589A2/pt not_active IP Right Cessation
- 2008-07-11 CN CN200880107096.4A patent/CN101801894B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2170788A1 (en) | 2010-04-07 |
| US20100191024A1 (en) | 2010-07-29 |
| EP2170788B1 (en) | 2018-06-13 |
| US8338651B2 (en) | 2012-12-25 |
| JP5722623B2 (ja) | 2015-05-27 |
| JP2010533151A (ja) | 2010-10-21 |
| CN101801894A (zh) | 2010-08-11 |
| TW200920721A (en) | 2009-05-16 |
| WO2009010472A1 (en) | 2009-01-22 |
| RU2010105051A (ru) | 2011-08-20 |
| CN101801894B (zh) | 2014-06-04 |
| BRPI0813589A2 (pt) | 2014-12-30 |
| KR20100043234A (ko) | 2010-04-28 |
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