JPH0521908B2 - - Google Patents
Info
- Publication number
- JPH0521908B2 JPH0521908B2 JP57112644A JP11264482A JPH0521908B2 JP H0521908 B2 JPH0521908 B2 JP H0521908B2 JP 57112644 A JP57112644 A JP 57112644A JP 11264482 A JP11264482 A JP 11264482A JP H0521908 B2 JPH0521908 B2 JP H0521908B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- mixture
- formula
- hours
- kpa
- 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 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 2
- HPKZHKRTMMLVBQ-UHFFFAOYSA-N fluoro propanoate Chemical class CCC(=O)OF HPKZHKRTMMLVBQ-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 32
- 238000009835 boiling Methods 0.000 description 30
- 229920001577 copolymer Polymers 0.000 description 25
- -1 alkali metal cyanide Chemical class 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 239000003039 volatile agent Substances 0.000 description 17
- 125000001309 chloro group Chemical group Cl* 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- KHYBIWCXJWMLBP-UHFFFAOYSA-N methyl 3-cyano-2,2,3,3-tetrafluoropropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C#N KHYBIWCXJWMLBP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RTFIHMZZXIFVAU-UHFFFAOYSA-M sodium;3-cyano-2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)(F)C#N RTFIHMZZXIFVAU-UHFFFAOYSA-M 0.000 description 8
- LIZZWVXXYAALGG-UHFFFAOYSA-N 1,1,2,3,3-pentafluoro-3-fluorosulfonyloxyprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)OS(F)(=O)=O LIZZWVXXYAALGG-UHFFFAOYSA-N 0.000 description 7
- YUDUFRYTKFGQCL-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanedioic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(O)=O YUDUFRYTKFGQCL-UHFFFAOYSA-N 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- UXXVQGAOXZZMMG-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoro-4-(1,1,2,3,3-pentafluoroprop-2-enoxy)butanenitrile Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C#N UXXVQGAOXZZMMG-UHFFFAOYSA-N 0.000 description 5
- KUFWEVRVCDZEDB-UHFFFAOYSA-M 3-cyano-2,2,3,3-tetrafluoropropanoate;triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.[O-]C(=O)C(F)(F)C(F)(F)C#N KUFWEVRVCDZEDB-UHFFFAOYSA-M 0.000 description 5
- 150000001265 acyl fluorides Chemical class 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229920002313 fluoropolymer Polymers 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 5
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 4
- INOKKRNSCIWTLK-UHFFFAOYSA-M 3-cyano-2,2,3,3-tetrafluoropropanoate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.[O-]C(=O)C(F)(F)C(F)(F)C#N INOKKRNSCIWTLK-UHFFFAOYSA-M 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- AJMXJHZFRBYZCR-UHFFFAOYSA-N methyl 3-azido-2,2,3,3-tetrafluoropropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)N=[N+]=[N-] AJMXJHZFRBYZCR-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 125000005499 phosphonyl group Chemical group 0.000 description 4
- LBCUVRZVAXCTCF-UHFFFAOYSA-M potassium;3-cyano-2,2,3,3-tetrafluoropropanoate Chemical compound [K+].[O-]C(=O)C(F)(F)C(F)(F)C#N LBCUVRZVAXCTCF-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- UAMNMPAFXNSWBD-UHFFFAOYSA-N 1-azido-1,1,2,2,3,3-hexafluoro-3-(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(C(C(OC(C(=C(F)F)F)(F)F)(F)F)(F)F)(F)N=[N+]=[N-] UAMNMPAFXNSWBD-UHFFFAOYSA-N 0.000 description 3
- NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- JVRUYYNHMKFOIU-UHFFFAOYSA-N 3,3,4,4,5,5-hexafluorooxolan-2-one Chemical compound FC1(F)OC(=O)C(F)(F)C1(F)F JVRUYYNHMKFOIU-UHFFFAOYSA-N 0.000 description 3
- RHEVXGYPJXWQRC-UHFFFAOYSA-M 3-azido-2,2,3,3-tetrafluoropropanoate;triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.[O-]C(=O)C(F)(F)C(F)(F)N=[N+]=[N-] RHEVXGYPJXWQRC-UHFFFAOYSA-M 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 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 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- BLZSSBPZHBFNBN-UHFFFAOYSA-N diethyl 2,2,3,3-tetrafluorobutanedioate Chemical compound CCOC(=O)C(F)(F)C(F)(F)C(=O)OCC BLZSSBPZHBFNBN-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003014 ion exchange membrane Substances 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- ZWBMALRBYQLPIM-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-methylsulfanylpropanoic acid Chemical compound CSC(F)(F)C(F)(F)C(O)=O ZWBMALRBYQLPIM-UHFFFAOYSA-N 0.000 description 2
- GDAHPFFIGLHTDF-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-methylsulfonylpropanoic acid Chemical compound CS(=O)(=O)C(F)(F)C(F)(F)C(O)=O GDAHPFFIGLHTDF-UHFFFAOYSA-N 0.000 description 2
- MYWRUVWOYAPWLT-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanediamide Chemical compound NC(=O)C(F)(F)C(F)(F)C(N)=O MYWRUVWOYAPWLT-UHFFFAOYSA-N 0.000 description 2
- LLNAXYXPFLGOOY-UHFFFAOYSA-N 3-azido-2,3,3-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl fluoride Chemical compound [N-]=[N+]=NC(F)(F)C(F)(C(=O)F)OC(F)(F)C(F)(F)C(F)(F)F LLNAXYXPFLGOOY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001916 cyano esters Chemical class 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- CTHMBXKAZJOFIK-UHFFFAOYSA-N methyl 2,2,3,3-tetrafluoro-3-methylsulfonylpropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)S(C)(=O)=O CTHMBXKAZJOFIK-UHFFFAOYSA-N 0.000 description 2
- GGWWWXATDNCWJI-UHFFFAOYSA-N methyl 3-azido-2,3,3-trifluoro-2-(trifluoromethoxy)propanoate Chemical compound COC(=O)C(F)(OC(F)(F)F)C(F)(F)N=[N+]=[N-] GGWWWXATDNCWJI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 125000006684 polyhaloalkyl group Polymers 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- IDKNFYAJCXJELZ-UHFFFAOYSA-M sodium 3-azido-2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)(F)N=[N+]=[N-] IDKNFYAJCXJELZ-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PJPKSPBWKPPLAM-UHFFFAOYSA-M sodium;2-chloro-3-cyano-2,3,3-trifluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(Cl)C(F)(F)C#N PJPKSPBWKPPLAM-UHFFFAOYSA-M 0.000 description 2
- DHBXEZKZKWEMCT-UHFFFAOYSA-M sodium;3-azido-2,3,3-trifluoro-2-(trifluoromethoxy)propanoate Chemical compound [Na+].FC(F)(F)OC(F)(C(=O)[O-])C(F)(F)N=[N+]=[N-] DHBXEZKZKWEMCT-UHFFFAOYSA-M 0.000 description 2
- XHFSFKAVPZMECC-UHFFFAOYSA-M sodium;3-tert-butylsulfanyl-2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].CC(C)(C)SC(F)(F)C(F)(F)C([O-])=O XHFSFKAVPZMECC-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YWXATJATWKLEDI-UHFFFAOYSA-N 1-azido-1,1,2,3,3-pentafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxypropane Chemical compound N(=[N+]=[N-])C(C(C(OC(C(OC(=C(F)F)F)(F)F)(C(F)(F)F)F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F YWXATJATWKLEDI-UHFFFAOYSA-N 0.000 description 1
- JEQOEFZQMKSQIZ-UHFFFAOYSA-M 2,2,3,3-tetrafluoro-3-methylsulfonylpropanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CS(=O)(=O)C(F)(F)C(F)(F)C([O-])=O JEQOEFZQMKSQIZ-UHFFFAOYSA-M 0.000 description 1
- YUDUFRYTKFGQCL-UHFFFAOYSA-L 2,2,3,3-tetrafluorobutanedioate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C([O-])=O YUDUFRYTKFGQCL-UHFFFAOYSA-L 0.000 description 1
- RAOHSZQQKCBEAD-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-1-(2,3,3,3-tetrafluoroprop-1-enoxy)prop-1-ene Chemical compound FC(=COC=C(F)C(F)(F)F)C(F)(F)F RAOHSZQQKCBEAD-UHFFFAOYSA-N 0.000 description 1
- FRCZQNWCKQMZPX-UHFFFAOYSA-N 2-cyano-2,3,3,3-tetrafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(C#N)C(F)(F)F FRCZQNWCKQMZPX-UHFFFAOYSA-N 0.000 description 1
- PQQLYBPGCGECTA-UHFFFAOYSA-M 3-azido-2,2,3,3-tetrafluoropropanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]C(=O)C(F)(F)C(F)(F)N=[N+]=[N-] PQQLYBPGCGECTA-UHFFFAOYSA-M 0.000 description 1
- BRGJYGHJTIVYOE-UHFFFAOYSA-N 3-azido-2,2,3,3-tetrafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)N=[N+]=[N-] BRGJYGHJTIVYOE-UHFFFAOYSA-N 0.000 description 1
- KKTQONMPBIGVDZ-UHFFFAOYSA-N 3-azido-2,3,3-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoic acid hydrate Chemical compound O.[N-]=[N+]=NC(F)(F)C(F)(C(=O)O)OC(F)(F)C(F)(F)C(F)(F)F KKTQONMPBIGVDZ-UHFFFAOYSA-N 0.000 description 1
- IJTAKAGEJXIJPQ-UHFFFAOYSA-N 3-chloro-1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)Cl IJTAKAGEJXIJPQ-UHFFFAOYSA-N 0.000 description 1
- CFVCBZAWVIBPPX-UHFFFAOYSA-N 3-cyano-2,2,3,3-tetrafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C#N CFVCBZAWVIBPPX-UHFFFAOYSA-N 0.000 description 1
- YQCJHGASNPRBNH-UHFFFAOYSA-N 3-cyano-2,2,3,3-tetrafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C#N YQCJHGASNPRBNH-UHFFFAOYSA-N 0.000 description 1
- JKTJPZITKZLMID-UHFFFAOYSA-N 3-fluoropropanoyl chloride Chemical compound FCCC(Cl)=O JKTJPZITKZLMID-UHFFFAOYSA-N 0.000 description 1
- PQCIEHNPMCWGNY-UHFFFAOYSA-N 7-azidohept-1-ene Chemical compound C=CCCCCCN=[N+]=[N-] PQCIEHNPMCWGNY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 235000016936 Dendrocalamus strictus Nutrition 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910006095 SO2F Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- XYVHEALCISRTHJ-UHFFFAOYSA-L calcium;3-cyano-2,2,3,3-tetrafluoropropanoate Chemical compound [Ca+2].[O-]C(=O)C(F)(F)C(F)(F)C#N.[O-]C(=O)C(F)(F)C(F)(F)C#N XYVHEALCISRTHJ-UHFFFAOYSA-L 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UBDULKDGOCZMFK-UHFFFAOYSA-N methyl 2-chloro-3-cyano-2,3,3-trifluoropropanoate Chemical compound COC(=O)C(F)(Cl)C(F)(F)C#N UBDULKDGOCZMFK-UHFFFAOYSA-N 0.000 description 1
- JFKNDWWYBWCTBB-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-propoxypropanoate Chemical compound CCCOC(C(F)(F)F)C(=O)OC JFKNDWWYBWCTBB-UHFFFAOYSA-N 0.000 description 1
- WKKWUVJUKMDFHJ-UHFFFAOYSA-N methyl 3-tert-butylsulfanyl-2,2,3,3-tetrafluoropropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)SC(C)(C)C WKKWUVJUKMDFHJ-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 229920005548 perfluoropolymer Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- OMOSXHQDCWPOKM-UHFFFAOYSA-M potassium;2,3,4,5,6-pentafluorophenolate Chemical compound [K+].[O-]C1=C(F)C(F)=C(F)C(F)=C1F OMOSXHQDCWPOKM-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- IJDRBJYPGCDHGR-UHFFFAOYSA-M sodium;2,2,3,3-tetrafluoro-3-methylsulfanylpropanoate Chemical compound [Na+].CSC(F)(F)C(F)(F)C([O-])=O IJDRBJYPGCDHGR-UHFFFAOYSA-M 0.000 description 1
- LFLIADONIMFSMY-UHFFFAOYSA-M sodium;3-dimethoxyphosphoryl-2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].COP(=O)(OC)C(F)(F)C(F)(F)C([O-])=O LFLIADONIMFSMY-UHFFFAOYSA-M 0.000 description 1
- BYMVZHORNHZYPQ-UHFFFAOYSA-N sodium;diethyl phosphite Chemical compound [Na+].CCOP([O-])OCC BYMVZHORNHZYPQ-UHFFFAOYSA-N 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 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
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28013381A | 1981-07-02 | 1981-07-02 | |
| US280133 | 1982-05-20 | ||
| US380016 | 1982-05-20 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2413588A Division JPH05255222A (ja) | 1981-07-02 | 1990-12-05 | β−置換ポリフルオロプロピオネート塩の誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5815947A JPS5815947A (ja) | 1983-01-29 |
| JPH0521908B2 true JPH0521908B2 (de) | 1993-03-25 |
Family
ID=23071819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11264482A Granted JPS5815947A (ja) | 1981-07-02 | 1982-07-01 | β−置換ポリフルオロプロピオネ−ト塩及びその誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5815947A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201402881RA (en) * | 2011-12-16 | 2014-08-28 | Solvay Specialty Polymers It | Fluoroallylsulfonyl azide monomers and polymers there from |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55160007A (en) * | 1979-05-31 | 1980-12-12 | Asahi Chem Ind Co Ltd | Novel fluorinated copolymer and production thereof |
| JPS55160029A (en) * | 1979-05-31 | 1980-12-12 | Asahi Chem Ind Co Ltd | Novel fluorinated cation exchange membrane and production thereof |
| JPS5651495A (en) * | 1979-10-04 | 1981-05-09 | Asahi Glass Co Ltd | Preparation of compound containing fluorine and phosphorus |
| JPS5672022A (en) * | 1979-11-20 | 1981-06-16 | Asahi Glass Co Ltd | Production of nonaqueous dispersion of carboxylic acid type fluorinated polymer |
| JPS5679110A (en) * | 1979-11-30 | 1981-06-29 | Asahi Glass Co Ltd | Preparation of modified polytetrafluoroethylene |
| JPS56139683A (en) * | 1980-04-01 | 1981-10-31 | Asahi Glass Co Ltd | Production of hydrogen |
| JPS56139684A (en) * | 1980-04-01 | 1981-10-31 | Asahi Glass Co Ltd | Production of hydrogen and chlorine |
| JPS5792028A (en) * | 1980-11-29 | 1982-06-08 | Asahi Chem Ind Co Ltd | Fluorocarbon cation exchange membrane |
| JPS57195126A (en) * | 1981-05-27 | 1982-11-30 | Asahi Glass Co Ltd | Fluorine-containing ion exchange membrane |
-
1982
- 1982-07-01 JP JP11264482A patent/JPS5815947A/ja active Granted
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55160007A (en) * | 1979-05-31 | 1980-12-12 | Asahi Chem Ind Co Ltd | Novel fluorinated copolymer and production thereof |
| JPS55160029A (en) * | 1979-05-31 | 1980-12-12 | Asahi Chem Ind Co Ltd | Novel fluorinated cation exchange membrane and production thereof |
| JPS5651495A (en) * | 1979-10-04 | 1981-05-09 | Asahi Glass Co Ltd | Preparation of compound containing fluorine and phosphorus |
| JPS5672022A (en) * | 1979-11-20 | 1981-06-16 | Asahi Glass Co Ltd | Production of nonaqueous dispersion of carboxylic acid type fluorinated polymer |
| JPS5679110A (en) * | 1979-11-30 | 1981-06-29 | Asahi Glass Co Ltd | Preparation of modified polytetrafluoroethylene |
| JPS56139683A (en) * | 1980-04-01 | 1981-10-31 | Asahi Glass Co Ltd | Production of hydrogen |
| JPS56139684A (en) * | 1980-04-01 | 1981-10-31 | Asahi Glass Co Ltd | Production of hydrogen and chlorine |
| JPS5792028A (en) * | 1980-11-29 | 1982-06-08 | Asahi Chem Ind Co Ltd | Fluorocarbon cation exchange membrane |
| JPS57195126A (en) * | 1981-05-27 | 1982-11-30 | Asahi Glass Co Ltd | Fluorine-containing ion exchange membrane |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5815947A (ja) | 1983-01-29 |
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