CA2951305C - Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene - Google Patents
Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene Download PDFInfo
- Publication number
- CA2951305C CA2951305C CA2951305A CA2951305A CA2951305C CA 2951305 C CA2951305 C CA 2951305C CA 2951305 A CA2951305 A CA 2951305A CA 2951305 A CA2951305 A CA 2951305A CA 2951305 C CA2951305 C CA 2951305C
- Authority
- CA
- Canada
- Prior art keywords
- hfc
- hfo
- composition
- additional compound
- compositions
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 title claims abstract description 74
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 26
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 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 abstract description 18
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 15
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 14
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims abstract description 14
- SUAMPXQALWYDBK-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoropropane Chemical compound FCC(F)(F)C(F)(F)F SUAMPXQALWYDBK-UHFFFAOYSA-N 0.000 claims abstract description 13
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 claims abstract description 12
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 12
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001294 propane Substances 0.000 claims abstract description 11
- 238000004378 air conditioning Methods 0.000 claims abstract 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 abstract description 7
- 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 claims abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012530 fluid Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 239000003507 refrigerant Substances 0.000 claims description 10
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 5
- 239000004088 foaming agent Substances 0.000 claims description 5
- 239000003380 propellant Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 abstract description 14
- -1 HFC- 236cb Chemical compound 0.000 abstract description 6
- 238000005057 refrigeration Methods 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 54
- 238000005796 dehydrofluorination reaction Methods 0.000 description 32
- 238000000197 pyrolysis Methods 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000003054 catalyst Substances 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 21
- 239000003444 phase transfer catalyst Substances 0.000 description 21
- 239000002585 base Substances 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000007789 gas Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- 229910052759 nickel Inorganic materials 0.000 description 10
- 239000002344 surface layer Substances 0.000 description 10
- 150000003983 crown ethers Chemical class 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003575 carbonaceous material Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 5
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 5
- 229910000990 Ni alloy Inorganic materials 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 5
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 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 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000000788 chromium alloy Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000002739 cryptand Substances 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000012808 vapor phase Substances 0.000 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 description 2
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910000599 Cr alloy Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052777 Praseodymium Inorganic materials 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 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 2
- 239000000243 solution Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- CDOOAUSHHFGWSA-UPHRSURJSA-N (z)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C/C(F)(F)F CDOOAUSHHFGWSA-UPHRSURJSA-N 0.000 description 1
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-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
- 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 description 1
- WFHFXEYKXJKYMG-UHFFFAOYSA-N 1,1,2-trichloro-1,3,3,3-tetrafluoropropane Chemical compound FC(F)(F)C(Cl)C(F)(Cl)Cl WFHFXEYKXJKYMG-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- UEOZRAZSBQVQKG-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorooxolane Chemical compound FC1(F)OC(F)(F)C(F)(F)C1(F)F UEOZRAZSBQVQKG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241001546602 Horismenus Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-methylmorpholine Substances CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 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
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- UNTITLLXXOKDTB-UHFFFAOYSA-N dibenzo-24-crown-8 Chemical compound O1CCOCCOCCOC2=CC=CC=C2OCCOCCOCCOC2=CC=CC=C21 UNTITLLXXOKDTB-UHFFFAOYSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical class OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- DMDPGPKXQDIQQG-UHFFFAOYSA-N pentaglyme Chemical compound COCCOCCOCCOCCOCCOC DMDPGPKXQDIQQG-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- NRZGVGVFPHPXEO-UHFFFAOYSA-M tetraphenylarsanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRZGVGVFPHPXEO-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
-
- 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
- C07C17/35—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
- 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
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/22—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
- C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Thermal Sciences (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Sorption Type Refrigeration Machines (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA3093427A CA3093427A1 (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12681308P | 2008-05-07 | 2008-05-07 | |
| US61/126,813 | 2008-05-07 | ||
| CA2719741A CA2719741C (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719741A Division CA2719741C (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3093427A Division CA3093427A1 (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2951305A1 CA2951305A1 (en) | 2009-11-12 |
| CA2951305C true CA2951305C (en) | 2020-10-06 |
Family
ID=40852026
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3093427A Pending CA3093427A1 (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
| CA3262933A Pending CA3262933A1 (en) | 2008-05-07 | 2009-05-07 | COMPOSITIONS CONTAINING 1,1,1,2,3-PENTAFLUOROPROPANE OR 2,3,3,3-TETRAFLUOROPROPENE |
| CA2719741A Active CA2719741C (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
| CA2951305A Active CA2951305C (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3093427A Pending CA3093427A1 (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
| CA3262933A Pending CA3262933A1 (en) | 2008-05-07 | 2009-05-07 | COMPOSITIONS CONTAINING 1,1,1,2,3-PENTAFLUOROPROPANE OR 2,3,3,3-TETRAFLUOROPROPENE |
| CA2719741A Active CA2719741C (en) | 2008-05-07 | 2009-05-07 | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US8147709B2 (enExample) |
| EP (3) | EP4477691A3 (enExample) |
| JP (2) | JP2011520016A (enExample) |
| KR (9) | KR102884920B1 (enExample) |
| CN (2) | CN102015956B (enExample) |
| AU (1) | AU2009244263B2 (enExample) |
| BR (1) | BRPI0907676B1 (enExample) |
| CA (4) | CA3093427A1 (enExample) |
| ES (1) | ES2421231T3 (enExample) |
| MX (3) | MX355723B (enExample) |
| RU (1) | RU2010149957A (enExample) |
| SG (4) | SG10201707156RA (enExample) |
| WO (1) | WO2009137656A1 (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8710282B2 (en) | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| ES2926707T3 (es) | 2008-05-07 | 2022-10-27 | Chemours Co Fc Llc | Composiciones |
| KR102884920B1 (ko) | 2008-05-07 | 2025-11-12 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 1,1,1,2,3-펜타플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물 |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| US8975454B2 (en) * | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8147710B2 (en) * | 2008-10-10 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy) chloride |
| RU2011154374A (ru) | 2009-06-03 | 2013-07-20 | Е.И.Дюпон Де Немур Энд Компани | Катализаторы и способ изготовления 2,3,3,3-тетрафторпропена |
| SI2845891T1 (sl) | 2009-12-22 | 2020-02-28 | The Chemours Company Fc, Llc | Sestavki, ki obsegajo 2,3,3,3-tetrafluoropropen in 2,3-dikloro-3,3-difluoropropen |
| US8961812B2 (en) * | 2010-04-15 | 2015-02-24 | E I Du Pont De Nemours And Company | Compositions comprising Z-1,2-difluoroethylene and uses thereof |
| US8961811B2 (en) * | 2010-04-15 | 2015-02-24 | E I Du Pont De Nemours And Company | Compositions comprising E-1,2-difluoroethylene and uses thereof |
| US8436218B2 (en) * | 2010-05-27 | 2013-05-07 | Honeywell International Inc. | Azeotrope-like composition of hexafluoropropane, hexafluoropropene and hydrogen fluoride |
| US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| FR2962130B1 (fr) | 2010-06-30 | 2012-07-20 | Arkema France | Composition a base de 2,3,3,3-tetrafluoropropene |
| FR2962442B1 (fr) * | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
| EP2603569B1 (en) | 2010-08-13 | 2018-07-18 | Carrier Corporation | Fluorinated hydrocarbon composition |
| IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
| JP5971123B2 (ja) | 2011-02-04 | 2016-08-17 | 旭硝子株式会社 | ２，３，３，３−テトラフルオロプロペンの精製方法 |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| EP2751180A1 (en) * | 2011-08-29 | 2014-07-09 | E. I. Du Pont de Nemours and Company | Compositions comprising 1,1,1,2,2-pentafluoropropane and a fluoroolefin and uses thereof |
| TR201815347T4 (tr) | 2012-02-13 | 2018-11-21 | Chemours Co Fc Llc | Tetrafloropropen, diflorometan, pentafloroetil ve tetrafloroetanı içeren soğutucu madde karışımları ve bunların kullanımları. |
| JP6011008B2 (ja) * | 2012-04-27 | 2016-10-19 | 旭硝子株式会社 | 共沸または共沸様組成物、および２，３，３，３−テトラフルオロプロペンまたはヘキサフルオロプロペンの製造方法 |
| JP5995567B2 (ja) * | 2012-07-12 | 2016-09-21 | キヤノン株式会社 | インプリント装置、それを用いた物品の製造方法 |
| TW201410856A (zh) | 2012-08-23 | 2014-03-16 | Du Pont | 含四氟丙烯及二氟甲烷的冷媒混合物及其運用 |
| WO2014043487A2 (en) | 2012-09-14 | 2014-03-20 | The Procter & Gamble Company | Aerosol antiperspirant compositions, products and methods |
| CN102994052B (zh) * | 2012-11-30 | 2015-09-09 | 徐超 | 一种空调用制冷剂 |
| US9321867B2 (en) | 2012-12-21 | 2016-04-26 | Honeywell International Inc. | Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers |
| US8791309B2 (en) * | 2012-12-21 | 2014-07-29 | Honeywell International Inc. | Synthesis of 3,3,3-trifluoropropyne |
| FR3000096B1 (fr) | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| EP2970055B1 (en) * | 2013-03-15 | 2018-07-25 | The Chemours Company FC, LLC | Process for the reduction of alkyne impurities in fluoroolefins |
| US9216932B2 (en) * | 2013-05-20 | 2015-12-22 | Honeywell International Inc. | Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene |
| US11186424B2 (en) | 2013-07-16 | 2021-11-30 | The Procter & Gamble Company | Antiperspirant spray devices and compositions |
| US11083915B2 (en) | 2013-07-16 | 2021-08-10 | The Procter & Gamble Company | Antiperspirant spray devices and compositions |
| GB2516694B (en) | 2013-07-30 | 2016-09-07 | Mexichem Amanco Holding Sa | Heat transfer compositions |
| US9662285B2 (en) | 2014-03-13 | 2017-05-30 | The Procter & Gamble Company | Aerosol antiperspirant compositions, products and methods |
| US9579265B2 (en) | 2014-03-13 | 2017-02-28 | The Procter & Gamble Company | Aerosol antiperspirant compositions, products and methods |
| WO2016047206A1 (ja) | 2014-09-25 | 2016-03-31 | ダイキン工業株式会社 | Ｈｆｃとｈｆｏとを含有する組成物 |
| ES2936064T3 (es) | 2014-09-26 | 2023-03-14 | Daikin Ind Ltd | Composición basada en haloolefina y uso de la misma |
| ES2998907T3 (en) * | 2014-09-26 | 2025-02-24 | Daikin Ind Ltd | Haloolefin-based composition |
| JP6543450B2 (ja) * | 2014-09-29 | 2019-07-10 | Ｐｈｃホールディングス株式会社 | 冷凍装置 |
| GB201501598D0 (en) | 2015-01-30 | 2015-03-18 | Mexichem Fluor Sa De Cv | Compositions |
| HRP20220209T4 (hr) | 2015-02-19 | 2024-12-20 | Daikin Industries, Ltd. | Sastav koji sadrži mješavinu fluoriranih ugljikovodika, i metoda proizvodnje istih |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| CN105089001B (zh) * | 2015-04-14 | 2017-02-22 | 宁波职业技术学院 | 一种北京郊区pm2.5的治理方法 |
| JP6328589B2 (ja) | 2015-05-29 | 2018-05-23 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| JP6780656B2 (ja) | 2015-12-16 | 2020-11-04 | Ａｇｃ株式会社 | ハイドロフルオロオレフィンの製造方法 |
| US10029964B2 (en) * | 2016-08-30 | 2018-07-24 | Honeywell International Inc. | Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water |
| JP6624126B2 (ja) * | 2017-03-13 | 2019-12-25 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| JP6551571B2 (ja) * | 2017-07-24 | 2019-07-31 | ダイキン工業株式会社 | 冷媒組成物 |
| JP6555315B2 (ja) * | 2017-10-16 | 2019-08-07 | ダイキン工業株式会社 | ＨＦＯ−１２３４ｚｅ（Ｅ）及びＨＦＣ−１３４を含有する冷媒組成物及びその使用 |
| FR3076553B1 (fr) * | 2018-01-08 | 2020-07-31 | Arkema France | Procede de purification du 1,1,1,2,3-pentafluoropropane et utilisation de celui-ci pour l'obtention de 2,3,3,3-tetrafluoropropene de haute purete. |
| FR3079359B1 (fr) * | 2018-03-22 | 2020-10-09 | Arkema France | Utilisation du 1-chloro-2,3,3,3-tetrafluoropropene pour l'isolation ou l'extinction d'arcs electriques |
| CN110343509B (zh) | 2018-04-02 | 2021-09-14 | 江西天宇化工有限公司 | 一种不可燃且能降低温室效应的混合制冷剂及其应用 |
| JP7332629B2 (ja) | 2018-04-30 | 2023-08-23 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | 安定化されたフルオロオレフィン組成物、並びにその生成、保管、及び使用方法 |
| KR102786822B1 (ko) | 2019-03-08 | 2025-03-27 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 가연성 및 비가연성 하이드로플루오로올레핀 함유 냉매를 재생하는 공정 및 방법 |
| JP7656161B2 (ja) * | 2019-07-08 | 2025-04-03 | ダイキン工業株式会社 | フッ化ビニル化合物の製造方法 |
| CN112794788B (zh) * | 2021-04-08 | 2021-07-09 | 泉州宇极新材料科技有限公司 | 以六氟丙烯为起始原料合成氟代异丁烯的方法 |
| US20250066653A1 (en) | 2022-01-18 | 2025-02-27 | The Chemours Company Fc, Llc | Fluoroolefin compositions containing a dye and methods for their production, storage and usage |
| WO2023177855A1 (en) | 2022-03-18 | 2023-09-21 | The Chemours Company Fc, Llc | Hydrocarbon additives for 1234yf composition and methods for their production, storage and usage |
| CN115417745A (zh) * | 2022-11-04 | 2022-12-02 | 北京宇极科技发展有限公司 | 一种合成氢氟烯烃的方法 |
| CN115894166B (zh) * | 2022-12-02 | 2025-06-17 | 西安近代化学研究所 | 气相氟化合成2,3,3,3-四氟丙烯的方法 |
| WO2025136893A1 (en) | 2023-12-18 | 2025-06-26 | The Chemours Company Fc, Llc | High temperature heat pump system and method of use |
Family Cites Families (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58146567A (ja) | 1982-02-25 | 1983-09-01 | Agency Of Ind Science & Technol | イオノフオアとして有用なポリエ−テル誘導体 |
| SU1706690A1 (ru) | 1988-04-19 | 1992-01-23 | Всесоюзный Научно-Исследовательский Институт Технического Углерода | Пористый углеродный материал |
| US4902838A (en) | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| JPH04110388A (ja) | 1990-08-31 | 1992-04-10 | Daikin Ind Ltd | 熱伝達用流体 |
| US5136113A (en) | 1991-07-23 | 1992-08-04 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenolysis |
| US5268122A (en) | 1991-08-28 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions |
| US5161275A (en) * | 1992-03-20 | 1992-11-10 | Safety Quest, Inc. | Vehicle seat liner to facilitate extraction of an injured driver |
| US5538659A (en) * | 1993-03-29 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including hexafluoropropane and a hydrofluorocarbon |
| US5396000A (en) | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| RU2073058C1 (ru) | 1994-12-26 | 1997-02-10 | Олег Николаевич Подчерняев | Озонобезопасная рабочая смесь |
| US5800729A (en) | 1995-07-26 | 1998-09-01 | Electric Power Research | Mixtures of pentafluoropropane and a hydrofluorocarbon having 3 to 6 carbon atoms |
| US6576153B2 (en) | 1995-09-14 | 2003-06-10 | Alliedsignal Inc. | Hydrofluorocarbon refrigerants for use in centrifugal chillers |
| US5954995A (en) | 1996-03-22 | 1999-09-21 | Goble; George H. | Drop-in substitutes for 1,1,1,2-tetrafluoroethane (R-134a) refrigerant |
| US6369284B1 (en) | 1997-01-31 | 2002-04-09 | E. I. Du Pont De Nemours And Company | Catalytic manufacture of pentafluoropropenes |
| US5788886A (en) * | 1997-05-05 | 1998-08-04 | E. I. Du Pont De Nemours And Company | Pentafluoropropane compositions |
| JPH11388A (ja) | 1997-06-12 | 1999-01-06 | Nippon Mizushiyori Giken:Kk | 消臭抗菌粉材 |
| US5954595A (en) * | 1998-01-27 | 1999-09-21 | Antonious; Anthony J. | Metalwood type golf club head with bi-level off-set outer side-walls |
| US6589355B1 (en) * | 1999-10-29 | 2003-07-08 | Alliedsignal Inc. | Cleaning processes using hydrofluorocarbon and/or hydrochlorofluorocarbon compounds |
| FR2806077B1 (fr) * | 2000-03-07 | 2004-01-30 | Solvay | Procede pour l'obtention d'un hydrofluoroalcane epure, hydrofluoroalcane epure, utilisation de l'hydrofluoroalcane et methode d'analyse d'un hydrofluoroalcane |
| US6548719B1 (en) | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
| CN106753250A (zh) * | 2002-10-25 | 2017-05-31 | 霍尼韦尔国际公司 | 含有氟取代烯烃的组合物 |
| US7230146B2 (en) | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
| US7279451B2 (en) * | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
| US7161049B2 (en) * | 2002-12-13 | 2007-01-09 | E. I. Du Pont De Nemours And Company | Process for purifying hydrofluoropropanes |
| US20040204734A1 (en) * | 2003-04-11 | 2004-10-14 | Wagner Darrell Orvin | Tunneling tool with subcutaneous transdermal illumination |
| US7566318B2 (en) * | 2003-04-11 | 2009-07-28 | Cardiac Pacemakers, Inc. | Ultrasonic subcutaneous dissection tool incorporating fluid delivery |
| US20040204735A1 (en) * | 2003-04-11 | 2004-10-14 | Shiroff Jason Alan | Subcutaneous dissection tool incorporating pharmacological agent delivery |
| US7218970B2 (en) * | 2003-06-20 | 2007-05-15 | Cardiac Pacemakers, Inc. | System for medical lead tunneling |
| TWI312853B (en) * | 2003-10-09 | 2009-08-01 | Panasonic Corporatio | Refrigerator |
| AU2004281281A1 (en) * | 2003-10-14 | 2005-04-28 | E.I. Dupont De Nemours And Company | Process for the preparation of 1,1,1,3,3-pentafluoropropane and 1,1,1,2,3-pentafluoropropane |
| US20050211949A1 (en) | 2003-11-13 | 2005-09-29 | Bivens Donald B | Detectable refrigerant compositions and uses thereof |
| US7641809B2 (en) | 2004-02-26 | 2010-01-05 | E. I. Du Pont De Nemours And Company | Tracer-containing compositions |
| KR101150177B1 (ko) * | 2004-04-16 | 2012-05-29 | 허니웰 인터내셔널 인코포레이티드 | 테트라플루오로프로펜과 트리플루오로요오드메탄으로 이루어진 공비-성 조성물 |
| US7098176B2 (en) | 2004-04-16 | 2006-08-29 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US7951982B2 (en) * | 2004-04-29 | 2011-05-31 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7655014B2 (en) * | 2004-12-06 | 2010-02-02 | Cameron Health, Inc. | Apparatus and method for subcutaneous electrode insertion |
| US20060179852A1 (en) * | 2005-02-16 | 2006-08-17 | Honeywell International Inc. | Compositions and methods for cleaning vapor compression systems |
| US20060243944A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| US20060243945A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| TWI657070B (zh) | 2005-06-24 | 2019-04-21 | 美商哈尼威爾國際公司 | 含有經氟取代之烯烴之組合物及其用途 |
| US7476771B2 (en) | 2005-11-01 | 2009-01-13 | E.I. Du Pont De Nemours + Company | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7335804B2 (en) * | 2005-11-03 | 2008-02-26 | Honeywell International Inc. | Direct conversion of HCFC 225ca/cb mixture |
| US7560602B2 (en) | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| US20070135847A1 (en) * | 2005-12-12 | 2007-06-14 | Kenknight Bruce H | Subcutaneous defibrillation system and method using same |
| US7687670B2 (en) * | 2006-03-31 | 2010-03-30 | E.I. Du Pont De Nemours And Company | Coproduction of hydrofluoroolefins |
| RU2399607C2 (ru) | 2006-04-03 | 2010-09-20 | Е.И.Дюпон Де Немур Энд Компани | Селективно взаимодействующие олефины, содержащие концевую группу cf2, в смеси |
| WO2007145171A1 (ja) | 2006-06-13 | 2007-12-21 | Central Glass Company, Limited | １，３，３，３－テトラフルオロプロペンの製造方法 |
| DE202007008291U1 (de) * | 2006-06-17 | 2007-10-18 | Ineos Fluor Holdings Ltd., Runcorn | Wärmeübertragungszusammensetzungen |
| GB2439392A (en) * | 2006-06-23 | 2007-12-27 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
| EP2043979B2 (en) * | 2006-06-27 | 2025-02-26 | The Chemours Company FC, LLC | Tetrafluoropropene production processes |
| WO2008002501A2 (en) | 2006-06-27 | 2008-01-03 | E. I. Du Pont De Nemours And Company | 1,2,3,3,3-pentafluoropropene production processes |
| CN101479219B (zh) * | 2006-06-27 | 2013-02-06 | 纳幕尔杜邦公司 | 四氟丙烯生产方法 |
| TW200801513A (en) | 2006-06-29 | 2008-01-01 | Fermiscan Australia Pty Ltd | Improved process |
| US7597744B2 (en) * | 2006-07-12 | 2009-10-06 | Honeywell International Inc. | Use of molecular sieves for the removal of HFC-23 from fluorocarbon products |
| GB0614080D0 (en) * | 2006-07-17 | 2006-08-23 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
| US8535555B2 (en) * | 2006-09-01 | 2013-09-17 | E I Du Pont De Nemours And Company | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| CN101535225A (zh) | 2006-09-05 | 2009-09-16 | 纳幕尔杜邦公司 | 制备氢氟烯烃的脱氟化氢方法 |
| US7420094B2 (en) * | 2006-09-05 | 2008-09-02 | E.I. Du Pont De Nemours And Company | Catalytic isomerization processes of 1,3,3,3-tetrafluoropropene for making 2,3,3,3-tetrafluoropropene |
| CN101535227B (zh) | 2006-09-05 | 2014-08-13 | 纳幕尔杜邦公司 | 制备2,3,3,3-四氟丙烯的方法 |
| EP2091898A1 (en) | 2006-10-31 | 2009-08-26 | E.I. Du Pont De Nemours And Company | Processes for producing 2,3,3,3-tetrafluoropropene and/or 1,2,3,3-tetrafluoropropene |
| CN101528645B (zh) | 2006-10-31 | 2013-10-30 | 纳幕尔杜邦公司 | 氟丙烷、卤代丙烯以及2-氯-3,3,3-三氟-1-丙烯与hf的共沸组合物和1,1,1,2,2-五氟丙烷与hf的共沸组合物的制备方法 |
| US7981312B2 (en) | 2006-10-31 | 2011-07-19 | E. I. Du Pont De Nemours And Company | Processes for producing and compositions comprising 2,3,3,3-tetrafluoropropene and/or 1,2,3,3-tetrafluoropropene |
| CN101535224A (zh) | 2006-10-31 | 2009-09-16 | 纳幕尔杜邦公司 | 制备2，3，3，3-四氟丙烯的方法、制备1-氯-2，2，3，3，3-五氟丙烷的方法以及1-氯-2，3，3，3，-四氟丙烯与hf的共沸组合物 |
| USRE49849E1 (en) | 2006-10-31 | 2024-02-27 | The Chemours Company Fc, Llc | Processes for the production of fluoropropanes and halopropenes |
| TW200837036A (en) | 2006-11-15 | 2008-09-16 | Du Pont | Process for producing 2,3,3,3-tetrafluoropropene |
| CN101617015A (zh) | 2006-12-15 | 2009-12-30 | 纳幕尔杜邦公司 | 由具有优化用于制冷性能的z-型和e-型异构体比率的1,2,3,3,3-五氟丙烯构成的组合物 |
| EP2099733B1 (en) * | 2006-12-20 | 2013-03-27 | E. I. Du Pont de Nemours and Company | Process for the synthesis and separation of hydrofluoroolefins |
| US20080207963A1 (en) | 2007-02-23 | 2008-08-28 | Velliyur Nott Mallikarjuna Rao | Preparation of composition containing chromium, oxygen, and either silver or palladium, and their use as catalysts and catalyst precursors |
| US20080207962A1 (en) | 2007-02-23 | 2008-08-28 | Velliyur Nott Mallikarjuna Rao | Compositions containing chromium, oxygen, and at least two modifier metals selected the group consisting of gold, silver, and palladium, their preparation, and their use as catalysts and catalyst precursors |
| US20080207964A1 (en) | 2007-02-23 | 2008-08-28 | Velliyur Nott Mallikarjuna Rao | Compositions containing chromium, oxygen and gold, their preparation, and their use as catalysts and catalyst precursors |
| US9561053B2 (en) * | 2007-04-25 | 2017-02-07 | Medtronic, Inc. | Implant tool to facilitate medical device implantation |
| ES2926707T3 (es) | 2008-05-07 | 2022-10-27 | Chemours Co Fc Llc | Composiciones |
| KR102884920B1 (ko) | 2008-05-07 | 2025-11-12 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 1,1,1,2,3-펜타플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물 |
| US8147710B2 (en) | 2008-10-10 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy) chloride |
| EP2349958A2 (en) | 2008-10-29 | 2011-08-03 | Daikin Industries, Ltd. | Process for preparing 2,3,3,3-tetrafluoropropene |
| SI2845891T1 (sl) | 2009-12-22 | 2020-02-28 | The Chemours Company Fc, Llc | Sestavki, ki obsegajo 2,3,3,3-tetrafluoropropen in 2,3-dikloro-3,3-difluoropropen |
-
2009
- 2009-05-07 KR KR1020247013444A patent/KR102884920B1/ko active Active
- 2009-05-07 CA CA3093427A patent/CA3093427A1/en active Pending
- 2009-05-07 US US12/437,014 patent/US8147709B2/en active Active
- 2009-05-07 KR KR1020197003233A patent/KR102116848B1/ko active Active
- 2009-05-07 SG SG10201707156RA patent/SG10201707156RA/en unknown
- 2009-05-07 SG SG10201707158QA patent/SG10201707158QA/en unknown
- 2009-05-07 KR KR1020217027451A patent/KR102470819B1/ko active Active
- 2009-05-07 CN CN200980116200.0A patent/CN102015956B/zh not_active Ceased
- 2009-05-07 KR KR1020167022099A patent/KR101822320B1/ko active Active
- 2009-05-07 MX MX2014009663A patent/MX355723B/es unknown
- 2009-05-07 CN CN201410189287.7A patent/CN103937460A/zh active Pending
- 2009-05-07 AU AU2009244263A patent/AU2009244263B2/en active Active
- 2009-05-07 ES ES09743642T patent/ES2421231T3/es active Active
- 2009-05-07 CA CA3262933A patent/CA3262933A1/en active Pending
- 2009-05-07 MX MX2010012145A patent/MX2010012145A/es active IP Right Grant
- 2009-05-07 EP EP24207424.3A patent/EP4477691A3/en active Pending
- 2009-05-07 MX MX2018005366A patent/MX370935B/es unknown
- 2009-05-07 BR BRPI0907676A patent/BRPI0907676B1/pt active IP Right Grant
- 2009-05-07 KR KR1020217039361A patent/KR102479255B1/ko active Active
- 2009-05-07 JP JP2011508654A patent/JP2011520016A/ja active Pending
- 2009-05-07 SG SG2013056809A patent/SG193153A1/en unknown
- 2009-05-07 KR KR1020207014867A patent/KR102335478B1/ko active Active
- 2009-05-07 RU RU2010149957/05A patent/RU2010149957A/ru not_active Application Discontinuation
- 2009-05-07 CA CA2719741A patent/CA2719741C/en active Active
- 2009-05-07 SG SG10202105126SA patent/SG10202105126SA/en unknown
- 2009-05-07 KR KR1020177036705A patent/KR101946315B1/ko active Active
- 2009-05-07 CA CA2951305A patent/CA2951305C/en active Active
- 2009-05-07 EP EP13164159.9A patent/EP2617794A3/en not_active Withdrawn
- 2009-05-07 EP EP09743642.2A patent/EP2271724B1/en not_active Revoked
- 2009-05-07 WO PCT/US2009/043111 patent/WO2009137656A1/en not_active Ceased
- 2009-05-07 KR KR1020227044011A patent/KR20230003633A/ko not_active Ceased
- 2009-05-07 KR KR1020107027386A patent/KR101650208B1/ko active Active
-
2012
- 2012-02-29 US US13/408,686 patent/US8333902B2/en active Active
- 2012-11-14 US US13/676,217 patent/US8692037B2/en not_active Ceased
-
2015
- 2015-05-20 JP JP2015103177A patent/JP2015212385A/ja active Pending
-
2016
- 2016-04-08 US US15/094,150 patent/USRE47862E1/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2951305C (en) | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene | |
| KR101921019B1 (ko) | 2,3-다이클로로-1,1,1-트라이플루오로프로판, 2-클로로-1,1,1-트라이플루오로프로펜, 2-클로로-1,1,1,2-테트라플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물 | |
| AU2014208303B2 (en) | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene | |
| HK1156064A (en) | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |