CA2389385A1 - Method for preparing imides from sulfonyl fluorides - Google Patents
Method for preparing imides from sulfonyl fluorides Download PDFInfo
- Publication number
- CA2389385A1 CA2389385A1 CA002389385A CA2389385A CA2389385A1 CA 2389385 A1 CA2389385 A1 CA 2389385A1 CA 002389385 A CA002389385 A CA 002389385A CA 2389385 A CA2389385 A CA 2389385A CA 2389385 A1 CA2389385 A1 CA 2389385A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorinated
- composition
- sulfonyl
- radical
- formula
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 92
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 150000003949 imides Chemical class 0.000 title claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- -1 cyclic alkyl radicals Chemical class 0.000 claims description 36
- 239000011734 sodium Substances 0.000 claims description 28
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 3
- 238000005342 ion exchange Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- 229910006095 SO2F Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 112
- 238000006243 chemical reaction Methods 0.000 description 75
- 239000011541 reaction mixture Substances 0.000 description 66
- 229910000104 sodium hydride Inorganic materials 0.000 description 38
- 239000007789 gas Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 235000019000 fluorine Nutrition 0.000 description 13
- 238000004293 19F NMR spectroscopy Methods 0.000 description 12
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 150000004678 hydrides Chemical class 0.000 description 7
- 210000003739 neck Anatomy 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 229920000554 ionomer Polymers 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 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 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002826 nitrites Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000095 alkaline earth hydride Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- PXLYROINIXKFAW-UHFFFAOYSA-N 1-(3-bromophenyl)-2-(methylamino)propan-1-one Chemical compound CNC(C)C(=O)C1=CC=CC(Br)=C1 PXLYROINIXKFAW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 102220572479 Protein tyrosine phosphatase type IVA 1_T13F_mutation Human genes 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910001423 beryllium ion Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 102200128606 rs143456784 Human genes 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16853999P | 1999-12-02 | 1999-12-02 | |
| US60/168,539 | 1999-12-02 | ||
| PCT/US2000/032672 WO2001040174A1 (en) | 1999-12-02 | 2000-12-01 | Method for preparing imides from sulfonyl fluorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2389385A1 true CA2389385A1 (en) | 2001-06-07 |
Family
ID=22611911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002389385A Abandoned CA2389385A1 (en) | 1999-12-02 | 2000-12-01 | Method for preparing imides from sulfonyl fluorides |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6759477B2 (enExample) |
| EP (1) | EP1237858B1 (enExample) |
| JP (1) | JP4723149B2 (enExample) |
| KR (1) | KR20020067534A (enExample) |
| CN (1) | CN1402705A (enExample) |
| AU (1) | AU1809901A (enExample) |
| CA (1) | CA2389385A1 (enExample) |
| DE (1) | DE60012225T2 (enExample) |
| WO (1) | WO2001040174A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2396614C (en) * | 2001-12-19 | 2005-07-20 | Inst Noguchi | Lewis acid catalyst composition |
| JP4176410B2 (ja) * | 2002-07-31 | 2008-11-05 | 旭化成株式会社 | ビススルホニルイミド基含有モノマーの製造方法 |
| CN100442051C (zh) * | 2005-11-28 | 2008-12-10 | 李寿椿 | 4-(n，n－二甲氨基)偶氮苯－4’-磺酰氟及其合成方法和用途 |
| JP2008266155A (ja) * | 2007-04-17 | 2008-11-06 | Asahi Kasei Corp | スルホンイミドリチウム塩の製造方法 |
| CN104447435A (zh) * | 2013-09-18 | 2015-03-25 | 中国科学院上海有机化学研究所 | 全氟烯烃磺酰亚胺类化合物及其制备方法 |
| KR101575439B1 (ko) * | 2013-12-27 | 2015-12-07 | 현대자동차주식회사 | 이종바인더가 적용된 리튬황 전지의 유황 양극 |
| CN113845660B (zh) * | 2021-09-26 | 2023-06-09 | 安徽国风新材料股份有限公司 | 一种基于硫氟交换点击化学制备聚酰亚胺薄膜的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282875A (en) | 1964-07-22 | 1966-11-01 | Du Pont | Fluorocarbon vinyl ether polymers |
| FR2637284B1 (fr) * | 1988-10-05 | 1991-07-05 | Elf Aquitaine | Methode de synthese de sulfonylimidures |
| FR2645533B1 (fr) * | 1989-04-06 | 1991-07-12 | Centre Nat Rech Scient | Procede de synthese de sulfonylimidures |
| US5463005A (en) * | 1992-01-03 | 1995-10-31 | Gas Research Institute | Copolymers of tetrafluoroethylene and perfluorinated sulfonyl monomers and membranes made therefrom |
| JP3117369B2 (ja) * | 1994-09-12 | 2000-12-11 | セントラル硝子株式会社 | スルホンイミドの製造方法 |
| DE69721748T2 (de) | 1996-12-30 | 2004-03-11 | Hydro-Québec, Montréal | Oberflächenmodifizierte kohlenstoffmaterialien |
| JPH11209338A (ja) * | 1998-01-20 | 1999-08-03 | Central Glass Co Ltd | スルホンイミドの製造方法 |
| CA2321695A1 (en) | 1998-03-03 | 1999-09-10 | Mark Gerrit Roelofs | Substantially fluorinated ionomers |
| HK1052686A1 (zh) * | 1999-11-23 | 2003-09-26 | 纳幕尔杜邦公司 | 制备二金属磺酰胺盐的方法 |
-
2000
- 2000-12-01 WO PCT/US2000/032672 patent/WO2001040174A1/en not_active Ceased
- 2000-12-01 CN CN00816376A patent/CN1402705A/zh active Pending
- 2000-12-01 CA CA002389385A patent/CA2389385A1/en not_active Abandoned
- 2000-12-01 JP JP2001541861A patent/JP4723149B2/ja not_active Expired - Fee Related
- 2000-12-01 DE DE60012225T patent/DE60012225T2/de not_active Expired - Lifetime
- 2000-12-01 KR KR1020027006864A patent/KR20020067534A/ko not_active Withdrawn
- 2000-12-01 US US10/129,168 patent/US6759477B2/en not_active Expired - Fee Related
- 2000-12-01 EP EP00980900A patent/EP1237858B1/en not_active Expired - Lifetime
- 2000-12-31 AU AU18099/01A patent/AU1809901A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1237858B1 (en) | 2004-07-14 |
| EP1237858A1 (en) | 2002-09-11 |
| WO2001040174A1 (en) | 2001-06-07 |
| JP2003515584A (ja) | 2003-05-07 |
| AU1809901A (en) | 2001-06-12 |
| CN1402705A (zh) | 2003-03-12 |
| DE60012225T2 (de) | 2005-09-08 |
| DE60012225D1 (de) | 2004-08-19 |
| JP4723149B2 (ja) | 2011-07-13 |
| US6759477B2 (en) | 2004-07-06 |
| US20020193499A1 (en) | 2002-12-19 |
| KR20020067534A (ko) | 2002-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |