CN103937460A - 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 - Google Patents
包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 Download PDFInfo
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- CN103937460A CN103937460A CN201410189287.7A CN201410189287A CN103937460A CN 103937460 A CN103937460 A CN 103937460A CN 201410189287 A CN201410189287 A CN 201410189287A CN 103937460 A CN103937460 A CN 103937460A
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- 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 69
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 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 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 22
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 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 description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000012546 transfer Methods 0.000 claims abstract description 10
- 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 9
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 9
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims abstract description 9
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 claims abstract description 9
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 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 8
- 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 8
- 238000004378 air conditioning Methods 0.000 claims abstract description 8
- 238000005057 refrigeration Methods 0.000 claims abstract description 8
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001294 propane Substances 0.000 claims abstract description 7
- 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 4
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000003380 propellant Substances 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 2
- -1 FC-1216 Chemical compound 0.000 abstract description 16
- 230000008569 process Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 56
- 238000005796 dehydrofluorination reaction Methods 0.000 description 38
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 32
- 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 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- 238000000197 pyrolysis Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000007789 gas Substances 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000003444 phase transfer catalyst Substances 0.000 description 21
- 239000003513 alkali Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052759 nickel Inorganic materials 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002344 surface layer Substances 0.000 description 10
- 238000005984 hydrogenation reaction Methods 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
- 150000003983 crown ethers Chemical class 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000003575 carbonaceous material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 4
- QBTUCBKAWGUMMK-UHFFFAOYSA-N C=CC.[F] Chemical group C=CC.[F] QBTUCBKAWGUMMK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000010306 acid treatment Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002739 cryptand Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 229910000765 intermetallic Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000990 Ni alloy Inorganic materials 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004458 analytical method Methods 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
- 239000006227 byproduct Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000010438 heat treatment Methods 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
- 238000002156 mixing Methods 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 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
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium 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
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000004566 building material Substances 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
- 150000001722 carbon compounds Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000919 ceramic Substances 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
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004079 fireproofing Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- HMSWAIKSFDFLKN-UHFFFAOYSA-N hexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000009434 installation 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
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 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
- 238000007789 sealing Methods 0.000 description 2
- 238000007086 side reaction Methods 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
- 239000000126 substance Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
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- 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
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- 229910001423 beryllium ion Inorganic materials 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- QLNAVQRIWDRPHA-UHFFFAOYSA-N iminophosphane Chemical compound P=N QLNAVQRIWDRPHA-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002603 lanthanum Chemical class 0.000 description 1
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- 239000003077 lignite Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 238000011068 loading method Methods 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
- KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-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
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 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
- 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
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 230000035924 thermogenesis Effects 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
- 230000008016 vaporization Effects 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
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- 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
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- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12681308P | 2008-05-07 | 2008-05-07 | |
| US61/126813 | 2008-05-07 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980116200.0A Division CN102015956B (zh) | 2008-05-07 | 2009-05-07 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103937460A true CN103937460A (zh) | 2014-07-23 |
Family
ID=40852026
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410189287.7A Pending CN103937460A (zh) | 2008-05-07 | 2009-05-07 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
| CN200980116200.0A Ceased CN102015956B (zh) | 2008-05-07 | 2009-05-07 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980116200.0A Ceased CN102015956B (zh) | 2008-05-07 | 2009-05-07 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
Country Status (13)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105089001A (zh) * | 2015-04-14 | 2015-11-25 | 宁波职业技术学院 | 一种北京郊区pm2.5的治理方法 |
| CN112794788A (zh) * | 2021-04-08 | 2021-05-14 | 北京宇极科技发展有限公司 | 以六氟丙烯为起始原料合成氟代异丁烯的方法 |
Families Citing this family (60)
| 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 |
| CA3008510C (en) | 2008-05-07 | 2021-03-09 | E. I. Du Pont De Nemours And Company | Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene |
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| 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 |
| WO2010042781A2 (en) * | 2008-10-10 | 2010-04-15 | 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 |
| MX2011012774A (es) | 2009-06-03 | 2012-01-20 | Du Pont | Catalizadores y proceso para la fabricacion de 2,3,3,3-tetrafluoropropeno. |
| EP3581631B1 (en) * | 2009-12-22 | 2024-11-06 | The Chemours Company FC, LLC | Compositions comprising 2,3,3,3-tetrafluoropropene |
| 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 |
| WO2012021746A1 (en) | 2010-08-13 | 2012-02-16 | Carrier Corporation | Fluorinated hydrocarbon composition |
| IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
| EP2671860B2 (en) | 2011-02-04 | 2024-05-29 | AGC Inc. | Method for purifying 2,3,3,3-tetrafluoropropene |
| GB2492847A (en) | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| JP2014525497A (ja) * | 2011-08-29 | 2014-09-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | １，１，１，２，２−ペンタフルオロプロパンおよびフルオロオレフィンを含む組成物ならびにその使用 |
| 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 |
| CA2882921C (en) | 2012-09-14 | 2017-10-24 | 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 |
| WO2014152325A1 (en) * | 2013-03-15 | 2014-09-25 | E.I. Du Pont De Nemours And Company | 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 |
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| US9662285B2 (en) | 2014-03-13 | 2017-05-30 | The Procter & Gamble Company | Aerosol antiperspirant compositions, products and methods |
| JP6153562B2 (ja) * | 2014-09-25 | 2017-06-28 | 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 |
| DK3130649T3 (da) | 2014-09-26 | 2025-02-03 | Daikin Ind Ltd | Haloolefin-baseret sammensætning |
| 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 |
| ES2732502T3 (es) | 2015-02-19 | 2019-11-22 | Daikin Ind Ltd | Composición que contiene una mezcla de hidrocarburos fluorados y método para producir la misma |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| 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 |
| EP3392229A4 (en) * | 2015-12-16 | 2019-08-07 | AGC Inc. | PROCESS FOR PREPARING HYDROFLUOROLEFIN |
| 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 |
| DE202019006151U1 (de) | 2018-04-30 | 2025-06-06 | The Chemours Company Fc, Llc | Stabilisierte Fluorolefinzusammensetzungen |
| JP2022524758A (ja) | 2019-03-08 | 2022-05-10 | 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 | 可燃性及び非可燃性ヒドロフルオロオレフィン含有冷媒を再生するためのプロセス及び方法 |
| 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 |
| KR20240134970A (ko) | 2022-01-18 | 2024-09-10 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 염료를 함유하는 플루오로올레핀 조성물, 및 이의 제조, 저장 및 사용 방법 |
| CA3243747A1 (en) | 2022-03-18 | 2023-09-21 | The Chemours Company Fc, Llc | HYDROCARBON ADDITIVES FOR A 1234YF COMPOSITION AND METHODS OF PRODUCTION, STORAGE AND USE |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080011159A1 (en) * | 2006-07-12 | 2008-01-17 | Honeywell International Inc. | Use of molecular sieves for the removal of HFC-23 from fluorocarbon products |
| WO2008027511A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
Family Cites Families (76)
| 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 |
| JP4031052B2 (ja) | 1997-01-31 | 2008-01-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ペンタフルオロプロペンの接触製造 |
| 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 |
| AU2003286685C1 (en) * | 2002-10-25 | 2013-05-23 | Honeywell International, Inc. | Compositions containing flourine substituted olefins |
| 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 |
| US20040204735A1 (en) * | 2003-04-11 | 2004-10-14 | Shiroff Jason Alan | Subcutaneous dissection tool incorporating pharmacological agent delivery |
| US7566318B2 (en) * | 2003-04-11 | 2009-07-28 | Cardiac Pacemakers, Inc. | Ultrasonic subcutaneous dissection tool incorporating fluid delivery |
| US20040204734A1 (en) * | 2003-04-11 | 2004-10-14 | Wagner Darrell Orvin | Tunneling tool with subcutaneous transdermal illumination |
| 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 |
| WO2005037743A1 (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 |
| US7098176B2 (en) * | 2004-04-16 | 2006-08-29 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene |
| JP5189358B2 (ja) * | 2004-04-16 | 2013-04-24 | ハネウェル・インターナショナル・インコーポレーテッド | テトラフルオロフ゜ロヘ゜ンとトリフルオロヨート゛メタンとの共沸性組成物 |
| 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 |
| US20060243945A1 (en) | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| US20060243944A1 (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 |
| US7560602B2 (en) | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| US7335804B2 (en) * | 2005-11-03 | 2008-02-26 | Honeywell International Inc. | Direct conversion of HCFC 225ca/cb mixture |
| US20070135847A1 (en) * | 2005-12-12 | 2007-06-14 | Kenknight Bruce H | Subcutaneous defibrillation system and method using same |
| WO2007117391A1 (en) | 2006-03-31 | 2007-10-18 | 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 |
| CN101479218B (zh) | 2006-06-27 | 2013-08-21 | 纳幕尔杜邦公司 | 1,2,3,3,3-五氟丙烯制备方法 |
| JP2009542650A (ja) * | 2006-06-27 | 2009-12-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | テトラフルオロプロペン製造方法 |
| US7722781B2 (en) * | 2006-06-27 | 2010-05-25 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| TW200801513A (en) | 2006-06-29 | 2008-01-01 | Fermiscan Australia Pty Ltd | Improved process |
| GB0614080D0 (en) * | 2006-07-17 | 2006-08-23 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
| ES2447037T3 (es) | 2006-09-05 | 2014-03-11 | E.I. Du Pont De Nemours And Company | Procedimiento de fabricación de 2,3,3,3-tetrafluoropropeno |
| US8288597B2 (en) * | 2006-09-05 | 2012-10-16 | E.I. Du Pont De Nemours And Company | Dehydrofluorination process to manufacture hydrofluoroolefins |
| 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 |
| USRE49849E1 (en) | 2006-10-31 | 2024-02-27 | The Chemours Company Fc, Llc | Processes for the production of fluoropropanes and halopropenes |
| CN101610987A (zh) | 2006-10-31 | 2009-12-23 | 纳幕尔杜邦公司 | 含有2,3,3,3-四氟丙烯和/或1,2,3,3-四氟丙烯的组合物及其制备方法 |
| US7906693B2 (en) | 2006-10-31 | 2011-03-15 | E.I. Du Pont De Nemours And Company | Processes for producing 2,3,3,3-tetrafluoropropene, a process for producing 1-chloro-2,3,3,3-pentafluoropropane and azeotropic compositions of 1-chloro-2,3,3,3-tetrafluoropropene with HF |
| CN103553871A (zh) | 2006-10-31 | 2014-02-05 | 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 |
| 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 |
| TW200837036A (en) | 2006-11-15 | 2008-09-16 | Du Pont | Process for producing 2,3,3,3-tetrafluoropropene |
| CA2671048A1 (en) | 2006-12-15 | 2008-06-26 | E.I. Dupont De Nemours And Company | Compositions comprising 1,2,3,3,3-pentafluoropropene with z- and e-isomer ratio optimized for refrigeration performance |
| JP2010513517A (ja) | 2006-12-20 | 2010-04-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ハイドロフルオロオレフィンの合成および分離方法 |
| 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 |
| 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 |
| US9561053B2 (en) * | 2007-04-25 | 2017-02-07 | Medtronic, Inc. | Implant tool to facilitate medical device implantation |
| US8147709B2 (en) | 2008-05-07 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Compositions comprising 3,3,3-trifluoropropyne |
| CA3008510C (en) | 2008-05-07 | 2021-03-09 | E. I. Du Pont De Nemours And Company | Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene |
| WO2010042781A2 (en) | 2008-10-10 | 2010-04-15 | 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 |
| EP3581631B1 (en) | 2009-12-22 | 2024-11-06 | The Chemours Company FC, LLC | Compositions comprising 2,3,3,3-tetrafluoropropene |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080011159A1 (en) * | 2006-07-12 | 2008-01-17 | Honeywell International Inc. | Use of molecular sieves for the removal of HFC-23 from fluorocarbon products |
| WO2008027511A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105089001A (zh) * | 2015-04-14 | 2015-11-25 | 宁波职业技术学院 | 一种北京郊区pm2.5的治理方法 |
| CN112794788A (zh) * | 2021-04-08 | 2021-05-14 | 北京宇极科技发展有限公司 | 以六氟丙烯为起始原料合成氟代异丁烯的方法 |
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