ES2504140T3 - Procedimiento para producir fluoro-olefinas - Google Patents
Procedimiento para producir fluoro-olefinas Download PDFInfo
- Publication number
- ES2504140T3 ES2504140T3 ES02773563.8T ES02773563T ES2504140T3 ES 2504140 T3 ES2504140 T3 ES 2504140T3 ES 02773563 T ES02773563 T ES 02773563T ES 2504140 T3 ES2504140 T3 ES 2504140T3
- Authority
- ES
- Spain
- Prior art keywords
- crown
- phase transfer
- alkali metal
- transfer catalyst
- chloride
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000003983 crown ethers Chemical class 0.000 claims description 17
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical group C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 8
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 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 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 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 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 8
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 description 7
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- PZNIYCULZNYNKM-UHFFFAOYSA-N 1,2-dibromo-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(Br)C(F)(F)Br PZNIYCULZNYNKM-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000007033 dehydrochlorination reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000005796 dehydrofluorination reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 2
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- QVXZSAWOXGFNIK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropan-2-ol Chemical compound FC(F)(F)C(F)(O)C(F)(F)F QVXZSAWOXGFNIK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical compound FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 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
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- -1 mono-ethyl ether Chemical compound 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-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
- 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
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/962,974 US6548719B1 (en) | 2001-09-25 | 2001-09-25 | Process for producing fluoroolefins |
| US962974 | 2001-09-25 | ||
| PCT/US2002/030353 WO2003027051A1 (en) | 2001-09-25 | 2002-09-25 | Process for producing fluoroolefins |
Publications (1)
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| ES2504140T3 true ES2504140T3 (es) | 2014-10-08 |
Family
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| ES02773563.8T Expired - Lifetime ES2504140T3 (es) | 2001-09-25 | 2002-09-25 | Procedimiento para producir fluoro-olefinas |
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| EP (1) | EP1430011B1 (enExample) |
| JP (2) | JP5093972B2 (enExample) |
| KR (1) | KR100883425B1 (enExample) |
| CN (1) | CN100473633C (enExample) |
| ES (1) | ES2504140T3 (enExample) |
| WO (1) | WO2003027051A1 (enExample) |
Families Citing this family (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6548719B1 (en) * | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
| US7279451B2 (en) * | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
| US7230146B2 (en) * | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
| US20040089839A1 (en) * | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
| US8033120B2 (en) * | 2002-10-25 | 2011-10-11 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
| US7880040B2 (en) * | 2004-04-29 | 2011-02-01 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US9255046B2 (en) * | 2003-07-25 | 2016-02-09 | Honeywell International Inc. | Manufacturing process for HFO-1234ze |
| US7592494B2 (en) * | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| US9499729B2 (en) * | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
| US9308199B2 (en) * | 2004-04-29 | 2016-04-12 | Honeywell International Inc. | Medicament formulations |
| US7655610B2 (en) * | 2004-04-29 | 2010-02-02 | Honeywell International Inc. | Blowing agent compositions comprising fluorinated olefins and carbon dioxide |
| CN1926778A (zh) * | 2004-02-27 | 2007-03-07 | 日本电气株式会社 | Cdma接收装置和方法 |
| US7951982B2 (en) * | 2004-04-29 | 2011-05-31 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| JP4864879B2 (ja) * | 2004-04-29 | 2012-02-01 | ハネウェル・インターナショナル・インコーポレーテッド | １，３，３，３−テトラフルオロプロペンの合成方法 |
| CA2564991C (en) * | 2004-04-29 | 2013-03-19 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene |
| US7659434B2 (en) | 2004-04-29 | 2010-02-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | 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 |
| CA2564897C (en) * | 2004-04-29 | 2012-11-27 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene |
| US9102579B2 (en) | 2004-04-29 | 2015-08-11 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8383867B2 (en) | 2004-04-29 | 2013-02-26 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US20060058428A1 (en) * | 2004-09-16 | 2006-03-16 | Honeywell International Inc. | Fluorinated compounds having epoxy and vinyl ether functional groups |
| US20060122301A1 (en) * | 2004-12-08 | 2006-06-08 | Honeywell International Inc. | Fluorinated divinyl ethers |
| US8574451B2 (en) * | 2005-06-24 | 2013-11-05 | Honeywell International Inc. | Trans-chloro-3,3,3-trifluoropropene for use in chiller applications |
| WO2007019358A2 (en) * | 2005-08-05 | 2007-02-15 | E. I. Du Pont De Nemours And Company | Process for the preparation of 1,3,3,3-tetrafluoropropene and/or 1,1,3,3,3-pentafluoropropene |
| US7423188B2 (en) | 2005-11-01 | 2008-09-09 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7902410B2 (en) * | 2005-11-03 | 2011-03-08 | Honeywell International Inc. | Process for the manufacture of fluorinated alkanes |
| WO2007056149A1 (en) * | 2005-11-03 | 2007-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US7560602B2 (en) * | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| ES2400732T3 (es) * | 2005-11-03 | 2013-04-11 | Honeywell International Inc. | Método para la producción de compuestos orgánicos fluorados |
| EP3336074B1 (en) | 2006-01-03 | 2025-07-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| ES2392591T3 (es) * | 2006-03-31 | 2012-12-12 | E.I. Du Pont De Nemours And Company | Coproducción de hidrofluoroolefinas |
| EP2046704A2 (en) * | 2006-06-27 | 2009-04-15 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US7485760B2 (en) * | 2006-08-24 | 2009-02-03 | Honeywell International Inc. | Integrated HFC trans-1234ze manufacture process |
| US8067650B2 (en) * | 2006-08-24 | 2011-11-29 | Honeywell International Inc. | Process for the production of HFO trans-1234ze from HFC-245fa |
| EP2066604B1 (en) | 2006-09-05 | 2015-06-03 | E. I. du Pont de Nemours and Company | Dehydrofluorination process to manufacture hydrofluoroolefins |
| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| US8013194B2 (en) | 2008-03-14 | 2011-09-06 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| US7803890B2 (en) * | 2006-12-20 | 2010-09-28 | Honeywell International Inc. | Fluorocopolymers |
| US8063149B2 (en) * | 2006-12-20 | 2011-11-22 | Honeywell International Inc. | Fluorocopolymers blends |
| JP5380882B2 (ja) * | 2007-04-17 | 2014-01-08 | セントラル硝子株式会社 | ３，３，３−トリフルオロプロピンの製造方法 |
| US7700815B2 (en) * | 2007-09-28 | 2010-04-20 | Honeywell International Inc | Method for producing fluorinated organic compounds |
| US9079818B2 (en) * | 2007-10-15 | 2015-07-14 | Honeywell International Inc. | Process for synthesis of fluorinated olefins |
| US8710282B2 (en) | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| GB0806389D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0806419D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| CN102015956B (zh) | 2008-05-07 | 2014-06-11 | 纳幕尔杜邦公司 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| FR2935701B1 (fr) * | 2008-09-11 | 2012-07-27 | Arkema France | Procede de preparation de composes fluores olefiniques |
| FR2935703B1 (fr) | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| RU2011130904A (ru) | 2008-12-25 | 2013-01-27 | Асахи Гласс Компани, Лимитед | Способы получения 1,1-дихлор-2,3,3,3-тетрафторпропена и 2,3,3,3-тетрафторпропена |
| US8552227B2 (en) * | 2009-01-05 | 2013-10-08 | E I Du Pont De Nemours And Company | Preparation of hydrofluoroolefins by dehydrofluorination |
| FR2940968B1 (fr) | 2009-01-13 | 2012-12-14 | Arkema France | Procede de preparation de composes fluores olefiniques |
| JP5598333B2 (ja) * | 2009-01-19 | 2014-10-01 | 旭硝子株式会社 | １，１−ジクロロ−２，２，３，３，３−ペンタフルオロプロパンの製造方法 |
| WO2010129844A1 (en) | 2009-05-08 | 2010-11-11 | E. I. Du Pont De Nemours And Company | Processes for reducing the amount of monofluoroacetate in hydrofluoroolefin production |
| FR2946338B1 (fr) | 2009-06-04 | 2012-12-28 | Arkema France | Procede de preparation de composes fluores olefiniques |
| FR2948360B1 (fr) | 2009-07-23 | 2011-08-05 | Arkema France | Procede de preparation de composes fluores olefiniques |
| US8129574B2 (en) | 2009-08-31 | 2012-03-06 | Honeywell International Inc. | Hydrogenation process for fluorocarbons |
| DK2474517T3 (en) * | 2009-08-31 | 2017-09-18 | Sumitomo Chemical Co | PROCEDURE FOR MANUFACTURING THE TRICHLOR-1 PROP |
| JP2013504658A (ja) | 2009-09-09 | 2013-02-07 | ハネウェル・インターナショナル・インコーポレーテッド | モノクロロトリフルオロプロペン化合物及び組成物並びにそれを用いる方法 |
| US7829748B1 (en) | 2009-09-21 | 2010-11-09 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| WO2011102538A2 (en) * | 2010-02-19 | 2011-08-25 | Daikin Industries, Ltd. | Process for producing 2-chloro-3,3,3-trifluoropropene |
| US8927791B2 (en) * | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| US8901360B2 (en) | 2010-05-21 | 2014-12-02 | Honeywell International Inc. | Process for cis 1,1,1,4,4,4-hexafluoro-2-butene |
| TW201204686A (en) * | 2010-06-23 | 2012-02-01 | Asahi Glass Co Ltd | Process for preparation of 1,1-dichloro-2,2,3,3,3-penta- fluoropropane |
| EP2586762B1 (en) * | 2010-06-23 | 2019-08-07 | AGC Inc. | Production method for 1,1-dichloro-2,3,3,3-tetra-fluoropropene and 2,3,3,3-tetrafluoropropene |
| US8436217B2 (en) | 2011-04-25 | 2013-05-07 | Honeywell International Inc. | Integrated process to co-produce 1,1,1,3,3-pentafluoropropane, trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| CN102887812A (zh) * | 2011-07-20 | 2013-01-23 | 中化蓝天集团有限公司 | 1,1,3,3,3-五氟丙烯的合成方法 |
| JPWO2013015201A1 (ja) * | 2011-07-22 | 2015-02-23 | 旭硝子株式会社 | 熱サイクル用作動媒体および熱サイクルシステム |
| JP5712894B2 (ja) * | 2011-10-14 | 2015-05-07 | セントラル硝子株式会社 | （ｚ）−１−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| US8889924B2 (en) | 2012-02-14 | 2014-11-18 | Honeywell International Inc. | Process for the production of 1,3,3,3-tetrafluoropropene |
| US8829254B2 (en) | 2012-02-14 | 2014-09-09 | Honeywell International Inc. | Process for making 1,3,3,3-tetrafluoropropene |
| JP6107466B2 (ja) | 2012-06-28 | 2017-04-05 | セントラル硝子株式会社 | トランス−１，３，３，３−テトラフルオロプロペンの精製方法 |
| JP6107467B2 (ja) | 2012-06-29 | 2017-04-05 | セントラル硝子株式会社 | １−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| JP6183370B2 (ja) * | 2012-09-21 | 2017-08-23 | セントラル硝子株式会社 | １，２−ジクロロ−３，３，３−トリフルオロプロペンの製造方法 |
| EP2922809A1 (en) * | 2012-09-28 | 2015-09-30 | E. I. du Pont de Nemours and Company | Dehydrochlorination of chlorinated reactants to produce 1,1,1,4,4,4-hexafluoro-2-butyne |
| US9532567B2 (en) * | 2012-11-29 | 2017-01-03 | Honeywell International Inc. | Synthesis and use of trans-1,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers |
| CN103880590B (zh) | 2012-12-19 | 2016-10-05 | 中化蓝天集团有限公司 | 一种制备1,3,3,3-四氟丙烯的工艺 |
| US8791309B2 (en) * | 2012-12-21 | 2014-07-29 | Honeywell International Inc. | Synthesis of 3,3,3-trifluoropropyne |
| US9289758B2 (en) | 2013-01-22 | 2016-03-22 | Axiall Ohio, Inc. | Processes for producing chlorinated hydrocarbons and methods for recovering polyvalent antimony catalysts therefrom |
| US8889930B2 (en) | 2013-01-22 | 2014-11-18 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons |
| US9216932B2 (en) * | 2013-05-20 | 2015-12-22 | Honeywell International Inc. | Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene |
| US9139497B2 (en) | 2013-10-23 | 2015-09-22 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound |
| KR20230031374A (ko) * | 2014-02-07 | 2023-03-07 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | Z-1,1,1,4,4,4-헥사플루오로-2-부텐의 생산을 위한 통합 공정 |
| JP6582569B2 (ja) * | 2014-07-28 | 2019-10-02 | セントラル硝子株式会社 | ２−クロロ−１，３，３，３−テトラフルオロプロペンの製造方法 |
| CN104177219B (zh) * | 2014-08-01 | 2018-02-13 | 巨化集团技术中心 | 一种制备1,3,3,3‑四氟丙烯的方法 |
| US9790150B2 (en) | 2014-08-12 | 2017-10-17 | The Chemours Company Fc, Llc | Processes for producing branched fluoroalkyl olefins |
| WO2016025288A1 (en) | 2014-08-14 | 2016-02-18 | The Chemours Company Fc, Llc | Process for the production of e-1,3,3,3-tetrafluoropropene (hfc-1234ze) by dehydrofluorinatiokl |
| US10093601B2 (en) | 2015-06-29 | 2018-10-09 | The Boeing Company | Fire retardant compounds |
| CN113968769A (zh) * | 2015-09-11 | 2022-01-25 | 科慕埃弗西有限公司 | 氢氯氟烃的脱卤化氢 |
| EP3395789B1 (en) * | 2015-12-25 | 2020-11-18 | AGC Inc. | Manufacturing method of 1-chloro-2,3,3,3-tetrafluoropropene |
| CN105837397A (zh) * | 2016-04-19 | 2016-08-10 | 四川西艾氟科技有限公司 | 一种全氟烷基乙烯的合成方法 |
| CN106892794B (zh) * | 2016-12-28 | 2019-10-15 | 西安近代化学研究所 | 一种制备反式-1,3,3,3-四氟丙烯的方法 |
| GB201701099D0 (en) * | 2017-01-23 | 2017-03-08 | Mexichem Fluor Sa De Cv | Process |
| US10611709B2 (en) * | 2017-09-11 | 2020-04-07 | The Chemours Company Fc, Llc | Liquid phase process for preparing (E)-1,1,1,4,4,4-hexafluorobut-2-ene |
| 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. |
| JP6974221B2 (ja) * | 2018-03-14 | 2021-12-01 | 株式会社クレハ | アルケンの製造方法 |
| FR3077072B1 (fr) | 2019-01-22 | 2021-08-06 | Arkema France | Procédé de purification du 1,1,1,2,3-pentafluoropropane et utilisation de celui-ci pour l’obtention de 2,3,3,3-tétrafluoropropène de haute pureté |
| CN113527040B (zh) * | 2020-04-22 | 2023-09-01 | 浙江省化工研究院有限公司 | 一种卤代丙烯的制备方法 |
| WO2023171325A1 (ja) * | 2022-03-09 | 2023-09-14 | 株式会社クレハ | アルケンの製造方法 |
| WO2023171326A1 (ja) * | 2022-03-09 | 2023-09-14 | 株式会社クレハ | アルケンの製造方法 |
| WO2025160051A2 (en) * | 2024-01-22 | 2025-07-31 | The Chemours Company Fc, Llc | Catalytic process for preparation of hydrofluoro(ether)olefins |
| WO2025160052A1 (en) * | 2024-01-22 | 2025-07-31 | The Chemours Company Fc, Llc | Integrated process to make 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889379A (en) | 1957-02-06 | 1959-06-02 | Dow Chemical Co | Preparation of 3, 3, 3-trifluoropropene |
| US3664966A (en) * | 1970-02-09 | 1972-05-23 | Continental Oil Co | Dehydrohalogenation catalyst |
| US4465786A (en) | 1982-09-27 | 1984-08-14 | General Electric Company | Catalyst composition for the preparation of 3,3,3-trifluoropropene |
| US4798818A (en) | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
| ATE172953T1 (de) | 1993-07-29 | 1998-11-15 | Allied Signal Inc | Verfahren zur herstellung von 1,1,1,3,3 pentafluorpropan |
| US5446217A (en) | 1994-05-16 | 1995-08-29 | Alliedsignal Inc. | Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin |
| JPH08169850A (ja) * | 1994-12-16 | 1996-07-02 | Daikin Ind Ltd | １，１，１，２，３，３−ヘキサフルオロプロパンの製造方法 |
| JP3778298B2 (ja) * | 1995-01-13 | 2006-05-24 | ダイキン工業株式会社 | ヘキサフルオロプロペンの製造方法 |
| US5696310A (en) * | 1996-04-12 | 1997-12-09 | Jackson; Andrew | Purification of 1,1,1,3,3-pentafluoropropane |
| US5710352A (en) | 1996-09-19 | 1998-01-20 | Alliedsignal Inc. | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene |
| US6023004A (en) | 1996-11-12 | 2000-02-08 | Alliedsignal, Inc. | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon |
| US5969198A (en) | 1997-06-27 | 1999-10-19 | Alliedsignal Inc. | Process for the preparation of 1,1,1,3,3-pentafluoropropane |
| JP4120043B2 (ja) * | 1998-04-01 | 2008-07-16 | 日本ゼオン株式会社 | フッ素化不飽和炭化水素の製造方法 |
| US6124510A (en) | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
| US6380446B1 (en) * | 2000-08-17 | 2002-04-30 | Dupont Dow Elastomers, L.L.C. | Process for dehydrohalogenation of halogenated compounds |
| US6548719B1 (en) * | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
-
2001
- 2001-09-25 US US09/962,974 patent/US6548719B1/en not_active Expired - Lifetime
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2002
- 2002-09-25 CN CNB028232666A patent/CN100473633C/zh not_active Expired - Fee Related
- 2002-09-25 KR KR1020047004392A patent/KR100883425B1/ko not_active Expired - Fee Related
- 2002-09-25 WO PCT/US2002/030353 patent/WO2003027051A1/en not_active Ceased
- 2002-09-25 JP JP2003530643A patent/JP5093972B2/ja not_active Expired - Fee Related
- 2002-09-25 EP EP02773563.8A patent/EP1430011B1/en not_active Expired - Lifetime
- 2002-09-25 ES ES02773563.8T patent/ES2504140T3/es not_active Expired - Lifetime
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2012
- 2012-07-30 JP JP2012168476A patent/JP2012233001A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US6548719B1 (en) | 2003-04-15 |
| CN1589248A (zh) | 2005-03-02 |
| EP1430011B1 (en) | 2014-07-23 |
| CN100473633C (zh) | 2009-04-01 |
| JP5093972B2 (ja) | 2012-12-12 |
| US20030060670A1 (en) | 2003-03-27 |
| WO2003027051A1 (en) | 2003-04-03 |
| JP2012233001A (ja) | 2012-11-29 |
| EP1430011A1 (en) | 2004-06-23 |
| JP2005504097A (ja) | 2005-02-10 |
| KR20040044993A (ko) | 2004-05-31 |
| KR100883425B1 (ko) | 2009-02-12 |
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