CN102083779A - 氟化醇 - Google Patents
氟化醇 Download PDFInfo
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- CN102083779A CN102083779A CN2009801257000A CN200980125700A CN102083779A CN 102083779 A CN102083779 A CN 102083779A CN 2009801257000 A CN2009801257000 A CN 2009801257000A CN 200980125700 A CN200980125700 A CN 200980125700A CN 102083779 A CN102083779 A CN 102083779A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 41
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- -1 alkali metal ammonia compound Chemical class 0.000 claims description 40
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 6
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 6
- 229910052728 basic metal Inorganic materials 0.000 claims description 6
- 150000003818 basic metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 60
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 55
- 235000019441 ethanol Nutrition 0.000 description 53
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 47
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 39
- 238000012360 testing method Methods 0.000 description 39
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000004094 surface-active agent Substances 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 31
- 229910052731 fluorine Inorganic materials 0.000 description 31
- 238000011156 evaluation Methods 0.000 description 30
- 239000013543 active substance Substances 0.000 description 29
- 239000011737 fluorine Substances 0.000 description 29
- 238000012790 confirmation Methods 0.000 description 27
- 239000007788 liquid Substances 0.000 description 27
- 239000011734 sodium Substances 0.000 description 26
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 24
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 23
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 22
- 239000008367 deionised water Substances 0.000 description 22
- 229910021641 deionized water Inorganic materials 0.000 description 22
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 238000004821 distillation Methods 0.000 description 20
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 17
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 16
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 16
- 238000005406 washing Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- 229940052303 ethers for general anesthesia Drugs 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000002390 rotary evaporation Methods 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
- 102100038239 Protein Churchill Human genes 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- MRPSASLEFZGUCD-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,6,6-undecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC(F)(F)CCI MRPSASLEFZGUCD-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229940018557 citraconic acid Drugs 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000007520 diprotic acids Chemical class 0.000 description 4
- WDMOWRSSQSYEEJ-UHFFFAOYSA-N ethene;hydroiodide Chemical compound I.C=C WDMOWRSSQSYEEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 description 4
- KOBXALIFCZVTOJ-UHFFFAOYSA-N 3,3,5,5,6,6,7,7,8,8,8-undecafluorooctan-1-ol Chemical compound OCCC(F)(F)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KOBXALIFCZVTOJ-UHFFFAOYSA-N 0.000 description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 2
- YXBZHGLURYLFOB-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,6,6,8,8-tridecafluoro-10-iododecane Chemical compound [H]C([H])(I)C([H])([H])C(F)(F)C([H])([H])C(F)(F)C([H])([H])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YXBZHGLURYLFOB-UHFFFAOYSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000003287 bathing Methods 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940018560 citraconate Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010932 ethanolysis reaction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 150000002978 peroxides Chemical group 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- PAHUTFPWSUWSCR-BHPSOXLSSA-N (z)-2-methylbut-2-enedioic acid Chemical compound OC(=O)C(/C)=C\C(O)=O.OC(=O)C(/C)=C\C(O)=O PAHUTFPWSUWSCR-BHPSOXLSSA-N 0.000 description 1
- UHSAWSFSPISWCW-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)CCI UHSAWSFSPISWCW-UHFFFAOYSA-N 0.000 description 1
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000107 caesium hydride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
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- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
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- 230000000474 nursing effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/165,743 US8173848B2 (en) | 2008-07-01 | 2008-07-01 | Fluorinated alcohols |
| US12/165743 | 2008-07-01 | ||
| PCT/US2009/048194 WO2010002622A1 (en) | 2008-07-01 | 2009-06-23 | Fluorinated alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102083779A true CN102083779A (zh) | 2011-06-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009801257000A Pending CN102083779A (zh) | 2008-07-01 | 2009-06-23 | 氟化醇 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8173848B2 (enExample) |
| EP (1) | EP2300404A1 (enExample) |
| JP (1) | JP2011526903A (enExample) |
| KR (1) | KR20110026000A (enExample) |
| CN (1) | CN102083779A (enExample) |
| AU (1) | AU2009264988A1 (enExample) |
| CA (1) | CA2725600A1 (enExample) |
| NZ (1) | NZ589118A (enExample) |
| WO (1) | WO2010002622A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107108456A (zh) * | 2014-12-19 | 2017-08-29 | 默克专利股份有限公司 | 氟化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120259143A1 (en) * | 2011-04-07 | 2012-10-11 | E.I. Du Pont De Nemours And Company | Fluoroalkylalkoxylates |
| US20120255651A1 (en) * | 2011-04-07 | 2012-10-11 | E.I. Du Pont De Nemours And Company | Fluoroalkylalkoxylates |
| JP6538726B2 (ja) * | 2014-06-11 | 2019-07-03 | ダウ シリコーンズ コーポレーション | 気体及び液体を反応させる膜接触器を使用して有機ケイ素生成物を生成する方法 |
Citations (1)
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| CN1665768A (zh) * | 2002-06-27 | 2005-09-07 | 旭硝子株式会社 | 含氟醇及其制备方法 |
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| US2951770A (en) | 1957-04-09 | 1960-09-06 | Minnesota Mining & Mfg | Method of making artificially colored granules, coating compositions employed therein and color-coated granule product thereof |
| US3133886A (en) | 1961-03-23 | 1964-05-19 | William A Zisman | Surface active compositions containing fluoroalcohols |
| CA1023768A (en) | 1972-12-21 | 1978-01-03 | Horst Jager | Polyfluoroalkyl iodides, process for their manufacture, and their use |
| US4167639A (en) | 1973-06-09 | 1979-09-11 | Hoechst Aktiengesellschaft | Fluorinated sulfosuccinates |
| US4018689A (en) | 1974-11-27 | 1977-04-19 | The Dow Chemical Company | Composition and method for reducing the surface tension of aqueous fluids |
| SU523086A1 (ru) | 1974-12-11 | 1976-07-30 | Предприятие П/Я Г-4236 | Соли фторорганических эфиров сульфо нтарной кислоты,как поверхностноактивные вещества |
| EP0130753B1 (en) | 1983-07-01 | 1987-12-09 | Lion Corporation | Process for producing sulfonate of unsaturated fatty acid ester |
| JPS62209200A (ja) | 1986-03-08 | 1987-09-14 | 日本油脂株式会社 | 非水洗浄用洗浄剤 |
| JPH0637369B2 (ja) | 1986-08-13 | 1994-05-18 | 三共株式会社 | 殺微生物組成物 |
| JPH01271484A (ja) | 1988-04-25 | 1989-10-30 | Taiho Ind Co Ltd | コークス製造用原料炭の処理剤 |
| CA1335388C (en) | 1989-03-17 | 1995-04-25 | Colin Stanton Jolly | Anti-skid composition for use on cellulosic fibrous materials |
| SU1728236A1 (ru) | 1990-02-13 | 1992-04-23 | Московское научно-производственное объединение "НИОПИК" | Симметричные или несимметричные фторсодержащие диэфиры сульфо нтарной кислоты в качестве смачивателей дл кинофотоматериалов |
| JPH06328849A (ja) | 1993-05-19 | 1994-11-29 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| JP3572077B2 (ja) | 1993-07-29 | 2004-09-29 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | ヨウ化パーフルオロアルキル類の製造方法 |
| WO1995011877A1 (fr) | 1993-10-27 | 1995-05-04 | Elf Atochem S.A. | Alcools polyfluores et leurs procedes de preparation |
| US5643864A (en) | 1994-08-19 | 1997-07-01 | Rhone-Poulenc, Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
| JPH08337976A (ja) | 1995-06-09 | 1996-12-24 | Kanegafuchi Chem Ind Co Ltd | パイル原反の連続染色法 |
| BR9608658A (pt) | 1995-06-22 | 1999-09-08 | Reckitt & Colman Inc | Composição de limpeza a seco doméstica, processo para limpeza a seco dómestica de um têxtil ou roupa, e, kit de limpeza |
| GB9604849D0 (en) | 1996-03-07 | 1996-05-08 | Reckitt & Colman Inc | Improvements in or relating to organic compositions |
| WO1997046283A1 (en) | 1996-06-06 | 1997-12-11 | Minnesota Mining And Manufacturing Company | Fire-fighting agents containing adsorbable fluorocarbon surfactants |
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| US7176331B2 (en) | 2005-06-30 | 2007-02-13 | 3M Innovative Properties Company | Method of making fluorinated vinyl ethers |
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2008
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-
2009
- 2009-06-23 NZ NZ589118A patent/NZ589118A/en not_active IP Right Cessation
- 2009-06-23 CA CA2725600A patent/CA2725600A1/en not_active Abandoned
- 2009-06-23 CN CN2009801257000A patent/CN102083779A/zh active Pending
- 2009-06-23 JP JP2011516503A patent/JP2011526903A/ja not_active Withdrawn
- 2009-06-23 AU AU2009264988A patent/AU2009264988A1/en not_active Abandoned
- 2009-06-23 EP EP09774074A patent/EP2300404A1/en not_active Withdrawn
- 2009-06-23 WO PCT/US2009/048194 patent/WO2010002622A1/en not_active Ceased
- 2009-06-23 KR KR1020117002456A patent/KR20110026000A/ko not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1665768A (zh) * | 2002-06-27 | 2005-09-07 | 旭硝子株式会社 | 含氟醇及其制备方法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107108456A (zh) * | 2014-12-19 | 2017-08-29 | 默克专利股份有限公司 | 氟化合物 |
| US11118066B2 (en) | 2014-12-19 | 2021-09-14 | Merck Patent Gmbh | Fluorine compounds |
| US11898058B2 (en) | 2014-12-19 | 2024-02-13 | Merck Patent Gmbh | Fluorine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009264988A1 (en) | 2010-01-07 |
| US20100004478A1 (en) | 2010-01-07 |
| JP2011526903A (ja) | 2011-10-20 |
| NZ589118A (en) | 2012-03-30 |
| KR20110026000A (ko) | 2011-03-14 |
| WO2010002622A1 (en) | 2010-01-07 |
| US8173848B2 (en) | 2012-05-08 |
| EP2300404A1 (en) | 2011-03-30 |
| CA2725600A1 (en) | 2010-01-07 |
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