CA1173199A - Obtention de composes polyfluoroallyloxy et copolymeres derives - Google Patents

Obtention de composes polyfluoroallyloxy et copolymeres derives

Info

Publication number: CA1173199A
Authority: CA; Canada
Prior art keywords: mol; fluoride; mixture; perfluoro; stirred
Prior art date: 1979-12-20
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

Application number

CA000435394A

Other languages

English (en)

Inventor

Carl G. Krespan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1979-12-20

Filing date

1983-08-25

Publication date

1984-08-21

1979-12-20 Priority claimed from ZA00796950A external-priority patent/ZA796950B/xx

1983-08-25 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1983-08-25 Priority to CA000435394A priority Critical patent/CA1173199A/fr

1984-08-21 Application granted granted Critical

1984-08-21 Publication of CA1173199A publication Critical patent/CA1173199A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 21
229920001577 copolymer Polymers 0.000 title claims description 52
238000002360 preparation method Methods 0.000 title description 9
239000000178 monomer Substances 0.000 claims abstract description 18
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 11
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims abstract description 5
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 35
238000000034 method Methods 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229910006095 SO2F Inorganic materials 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000000524 functional group Chemical group 0.000 claims description 8
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
239000012528 membrane Substances 0.000 claims description 5
BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 41
229920000642 polymer Polymers 0.000 abstract description 24
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 23
239000002253 acid Substances 0.000 abstract description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 12
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 abstract description 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 8
GEWFYVHBZSLJEZ-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-(1,1,2,3,3-pentafluoroprop-2-enoxy)ethanesulfonyl fluoride Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)S(F)(=O)=O GEWFYVHBZSLJEZ-UHFFFAOYSA-N 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 77
239000011698 potassium fluoride Substances 0.000 description 56
-1 methoxy, cyano, iodo Chemical group 0.000 description 47
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
229910001868 water Inorganic materials 0.000 description 39
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 38
239000000047 product Substances 0.000 description 38
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
238000005481 NMR spectroscopy Methods 0.000 description 21
235000003270 potassium fluoride Nutrition 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 19
238000004293 19F NMR spectroscopy Methods 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000004821 distillation Methods 0.000 description 17
239000010410 layer Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
229920001343 polytetrafluoroethylene Polymers 0.000 description 14
239000002904 solvent Substances 0.000 description 14
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 13
150000001450 anions Chemical class 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 12
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 12
229940058401 polytetrafluoroethylene Drugs 0.000 description 12
239000004810 polytetrafluoroethylene Substances 0.000 description 12
KQAPHIQIAHGITH-UHFFFAOYSA-N 1,2,2,2-tetrafluoroethanesulfonyl fluoride Chemical compound FC(F)(F)C(F)S(F)(=O)=O KQAPHIQIAHGITH-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
238000000113 differential scanning calorimetry Methods 0.000 description 11
239000000725 suspension Substances 0.000 description 11
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 9
238000004458 analytical method Methods 0.000 description 9
238000009835 boiling Methods 0.000 description 9
238000005755 formation reaction Methods 0.000 description 9
239000007789 gas Substances 0.000 description 9
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 9
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000010528 free radical solution polymerization reaction Methods 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229910001512 metal fluoride Inorganic materials 0.000 description 8
239000003039 volatile agent Substances 0.000 description 8
150000001728 carbonyl compounds Chemical class 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000007334 copolymerization reaction Methods 0.000 description 7
238000006073 displacement reaction Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
239000012535 impurity Substances 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
239000000463 material Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000002222 fluorine compounds Chemical class 0.000 description 6
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
239000000523 sample Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
OQUQGPIATTWEFF-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluoro-6-(1,1,2,3,3-pentafluoroprop-2-enoxy)hexanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F OQUQGPIATTWEFF-UHFFFAOYSA-N 0.000 description 5
DQWRXSPZQZNYRX-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropanoyl fluoride Chemical compound FC(F)C(F)(F)C(F)=O DQWRXSPZQZNYRX-UHFFFAOYSA-N 0.000 description 5
KJOOJFLEZNWPIN-UHFFFAOYSA-N 2,2-difluoropropanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)=O KJOOJFLEZNWPIN-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000003999 initiator Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
LIJKQESROBUSFB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-oxopropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(=O)C(F)(F)F LIJKQESROBUSFB-UHFFFAOYSA-N 0.000 description 4
SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 4
HENCJRDUTWWBFY-UHFFFAOYSA-N 2-cyano-2,2-difluoroacetyl fluoride Chemical compound FC(=O)C(F)(F)C#N HENCJRDUTWWBFY-UHFFFAOYSA-N 0.000 description 4
LLBCDOYDDNKNSQ-UHFFFAOYSA-N 2-ethoxy-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound CCOC(=C(F)F)C(F)(F)F LLBCDOYDDNKNSQ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000000975 dye Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229920002313 fluoropolymer Polymers 0.000 description 4
238000005194 fractionation Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
238000004876 x-ray fluorescence Methods 0.000 description 4
URXYEXLEZZBAIX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(1,1,2,3,3-pentafluoroprop-2-enoxy)butane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)F URXYEXLEZZBAIX-UHFFFAOYSA-N 0.000 description 3
LFBZMMIMHQHBFE-UHFFFAOYSA-N 1,1,2,2,4,4,5,5-octafluoro-1,3,3,5-tetramethoxypentane Chemical compound COC(F)(F)C(F)(F)C(OC)(OC)C(F)(F)C(F)(F)OC LFBZMMIMHQHBFE-UHFFFAOYSA-N 0.000 description 3
MHNPWFZIRJMRKC-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound F[C]=C(F)F MHNPWFZIRJMRKC-UHFFFAOYSA-N 0.000 description 3
RJYJDEJAFADMLE-UHFFFAOYSA-N 1-chloro-1,1,2,3,3,3-hexafluoro-2-(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)Cl RJYJDEJAFADMLE-UHFFFAOYSA-N 0.000 description 3
DTTSTUNIWPEOKC-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-3-oxopentanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(=O)C(F)(F)C(F)=O DTTSTUNIWPEOKC-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
229910001870 ammonium persulfate Inorganic materials 0.000 description 3
229910052925 anhydrite Inorganic materials 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004455 differential thermal analysis Methods 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000007720 emulsion polymerization reaction Methods 0.000 description 3
IWYWYPXNZJXKNS-UHFFFAOYSA-N ethyl 1,1,3,3,3-pentafluoro-2-oxopropane-1-sulfonate Chemical compound CCOS(=O)(=O)C(F)(F)C(=O)C(F)(F)F IWYWYPXNZJXKNS-UHFFFAOYSA-N 0.000 description 3
IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 3
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
WFRUBUQWJYMMRQ-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WFRUBUQWJYMMRQ-UHFFFAOYSA-M 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
IJEKHZDQURMSCF-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-(1,1,2,3,3-pentafluoroprop-2-enoxy)octane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F IJEKHZDQURMSCF-UHFFFAOYSA-N 0.000 description 2
TZLOXHKLJUZTLW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-bis(1,1,2,3,3-pentafluoroprop-2-enoxy)hexane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F TZLOXHKLJUZTLW-UHFFFAOYSA-N 0.000 description 2
JGEWGXVFZFMKMC-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1,3-bis(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F JGEWGXVFZFMKMC-UHFFFAOYSA-N 0.000 description 2
IXTJTMUIZVVXFD-UHFFFAOYSA-N 1,1,2,2,4,4,5,5-octafluoro-1,5-dimethoxypentan-3-one Chemical compound COC(F)(F)C(F)(F)C(=O)C(F)(F)C(F)(F)OC IXTJTMUIZVVXFD-UHFFFAOYSA-N 0.000 description 2
QRKKTXWUDLJYCV-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)(Cl)C(=O)C(F)(F)Cl QRKKTXWUDLJYCV-UHFFFAOYSA-N 0.000 description 2
OJUUDWYPNQALHZ-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(F)(F)Cl OJUUDWYPNQALHZ-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical compound FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 description 2
YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 2
ZILWJLIFAGWGLE-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZILWJLIFAGWGLE-UHFFFAOYSA-N 0.000 description 2
CLZVMMVCWAKKHN-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-5-(1,1,2,3,3-pentafluoroprop-2-enoxy)pentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F CLZVMMVCWAKKHN-UHFFFAOYSA-N 0.000 description 2
FDGCJTUAVVJFMB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorohexanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=O FDGCJTUAVVJFMB-UHFFFAOYSA-N 0.000 description 2
QAAOKGABNKTQRD-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-(1,1,2,3,3-pentafluoroprop-2-enoxy)propanenitrile Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C#N QAAOKGABNKTQRD-UHFFFAOYSA-N 0.000 description 2
XXNILTDSQBSKJO-UHFFFAOYSA-N 2,2-difluoro-2-(1,1,2-trifluoro-2-oxoethoxy)acetyl fluoride Chemical compound FC(=O)C(F)(F)OC(F)(F)C(F)=O XXNILTDSQBSKJO-UHFFFAOYSA-N 0.000 description 2
YIHXQSQQJBEAKK-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetyl fluoride Chemical compound FC(=O)C(F)(F)S(F)(=O)=O YIHXQSQQJBEAKK-UHFFFAOYSA-N 0.000 description 2
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150000004706 metal oxides Chemical class 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
YZXATMRKZPAQSK-UHFFFAOYSA-N methyl 2,2,3,3-tetrafluoro-3-(1,1,1,2,3-pentafluoro-3-oxopropan-2-yl)oxypropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)OC(F)(C(F)=O)C(F)(F)F YZXATMRKZPAQSK-UHFFFAOYSA-N 0.000 description 1
NDNOUXQCMAHOSA-UHFFFAOYSA-N methyl 2,2,3,3-tetrafluoro-3-methoxypropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)OC NDNOUXQCMAHOSA-UHFFFAOYSA-N 0.000 description 1
JNUANKSYWLJTDJ-UHFFFAOYSA-N methyl 2,2,3-trifluoro-3-oxopropanoate Chemical compound COC(=O)C(F)(F)C(F)=O JNUANKSYWLJTDJ-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 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
238000000465 moulding Methods 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
MOSWMBWMCPHPCL-UHFFFAOYSA-N non-1-ene Chemical compound [CH2]CCCCCCC=C MOSWMBWMCPHPCL-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
LMFJKKGDLAICPF-UHFFFAOYSA-N phenanthrene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC3=CC=CC=C3C2=C1 LMFJKKGDLAICPF-UHFFFAOYSA-N 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229940114930 potassium stearate Drugs 0.000 description 1
WPDDXKNWUVLZMQ-UHFFFAOYSA-M potassium;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound [K+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WPDDXKNWUVLZMQ-UHFFFAOYSA-M 0.000 description 1
ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000013341 scale-up Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000435394A 1979-12-20 1983-08-25 Obtention de composes polyfluoroallyloxy et copolymeres derives Expired CA1173199A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000435394A CA1173199A (fr)	1979-12-20	1983-08-25	Obtention de composes polyfluoroallyloxy et copolymeres derives

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ZA00796950A ZA796950B (en)	1979-12-20	1979-12-20	Polyfluorallyloxy compounds, their preparation and copolymers therefrom
CA000350850A CA1166651A (fr)	1979-12-20	1980-04-29	Composes polyfluoroallyloxy, preparation et copolymeres derives
CA000435394A CA1173199A (fr)	1979-12-20	1983-08-25	Obtention de composes polyfluoroallyloxy et copolymeres derives

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000350850A Division CA1166651A (fr)	1979-12-20	1980-04-29	Composes polyfluoroallyloxy, preparation et copolymeres derives

Publications (1)

Publication Number	Publication Date
CA1173199A true CA1173199A (fr)	1984-08-21

Family

ID=27166670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000435394A Expired CA1173199A (fr)	1979-12-20	1983-08-25	Obtention de composes polyfluoroallyloxy et copolymeres derives

Country Status (1)

Country	Link
CA (1)	CA1173199A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2554530B1 (fr)	2010-03-29	2016-07-13	Daikin Industries, Ltd.	Procédé de production de 3-chloro-pentafluoropropène

1983
- 1983-08-25 CA CA000435394A patent/CA1173199A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2554530B1 (fr)	2010-03-29	2016-07-13	Daikin Industries, Ltd.	Procédé de production de 3-chloro-pentafluoropropène
EP2554530B2 (fr) †	2010-03-29	2019-06-12	Daikin Industries, Ltd.	Procédé de production de 3-chloro-pentafluoropropène

Legal Events

Date	Code	Title	Description
2001-08-21	MKEX	Expiry

Publication	Publication Date	Title
US4275225A (en)	1981-06-23	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US4349650A (en)	1982-09-14	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US4273729A (en)	1981-06-16	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US4273728A (en)	1981-06-16	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
GB1571356A (en)	1980-07-16	Polyfluoroallyloxy compounds their preparation and copolymers therefrom
US4131740A (en)	1978-12-26	Alkyl perfluoro-ω-fluoroformyl esters and their preparation
US3560568A (en)	1971-02-02	Preparation of sulfonic acid containing fluorocarbon vinyl ethers
US4292449A (en)	1981-09-29	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US4526948A (en)	1985-07-02	Fluorinated vinyl ethers, copolymers thereof, and precursors thereto
US4420638A (en)	1983-12-13	Fluorinated ether-ketones
US4414159A (en)	1983-11-08	Vinyl ether monomers and polymers therefrom
US4334082A (en)	1982-06-08	Dialkyl perfluoro-ω-fluoroformyl diesters and monomers and polymers therefrom
CA1173199A (fr)	1984-08-21	Obtention de composes polyfluoroallyloxy et copolymeres derives
JPS61171706A (ja)	1986-08-02	弗素化オレフイン、その共重合体およびそれらの製造法
US4454247A (en)	1984-06-12	Ion exchange membranes
US4434273A (en)	1984-02-28	Perfluoroketovinyl ethers and copolymers therefrom
CA1174685A (fr)	1984-09-18	Obtention de composes polyfluoroallyloxy et de copolymeres de derives
CA1141088A (fr)	1983-02-08	Obtention de composes polyfluoroallyloxy et copolymeres derives
CA1166651A (fr)	1984-05-01	Composes polyfluoroallyloxy, preparation et copolymeres derives
US4675453A (en)	1987-06-23	Process and intermediates for fluorinated vinyl ether monomer
US5023362A (en)	1991-06-11	Alkyl perfluoro(2-methyl-5-oxo-3-oxahexanoate)
US4556747A (en)	1985-12-03	Fluorinated vinyl ethers, copolymers thereof, and precursors thereto
CA1155801A (fr)	1983-10-25	Membrane conductrice faite de copolymeres polyfluoro-allyloxy
US4304927A (en)	1981-12-08	Carboxylic acids, esters and salts of polyfluoroacetone
US4474998A (en)	1984-10-02	Fluorinated polyether and derivatives thereof