JP5843846B2 - ポリフルオロアルキルスルホンアミドアルキルアミンの混合物 - Google Patents
ポリフルオロアルキルスルホンアミドアルキルアミンの混合物 Download PDFInfo
- Publication number
- JP5843846B2 JP5843846B2 JP2013501380A JP2013501380A JP5843846B2 JP 5843846 B2 JP5843846 B2 JP 5843846B2 JP 2013501380 A JP2013501380 A JP 2013501380A JP 2013501380 A JP2013501380 A JP 2013501380A JP 5843846 B2 JP5843846 B2 JP 5843846B2
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- JP
- Japan
- Prior art keywords
- formula
- reaction
- mixture
- polyfluoroalkylsulfonamidoalkyl
- halide
- 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 - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 41
- 150000004820 halides Chemical class 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- -1 sulfonamide alkylamines Chemical class 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 19
- 229940124530 sulfonamide Drugs 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000005695 dehalogenation reaction Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 65
- 239000000460 chlorine Substances 0.000 description 45
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 44
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
- 238000004817 gas chromatography Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 12
- NDBZVZPOTNLWLU-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCS(Cl)(=O)=O NDBZVZPOTNLWLU-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000002140 halogenating effect Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- IHPRVZKJZGXTBQ-UHFFFAOYSA-N 3-chloropropan-1-amine;hydron;chloride Chemical compound Cl.NCCCCl IHPRVZKJZGXTBQ-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
- GBCQLGDTLMHVHU-UHFFFAOYSA-N 2,3,4,4a,5,6,7,8,9,9a-decahydro-1h-benzo[7]annulene Chemical compound C1CCCCC2CCCCC21 GBCQLGDTLMHVHU-UHFFFAOYSA-N 0.000 description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- NWYYWIJOWOLJNR-UHFFFAOYSA-N 2-Amino-3-methyl-1-butanol Chemical compound CC(C)C(N)CO NWYYWIJOWOLJNR-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- CXMYWOCYTPKBPP-UHFFFAOYSA-N 3-(3-hydroxypropylamino)propan-1-ol Chemical compound OCCCNCCCO CXMYWOCYTPKBPP-UHFFFAOYSA-N 0.000 description 1
- KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 1
- FVXBTPGZQMNAEZ-UHFFFAOYSA-N 3-amino-2-methylpropan-1-ol Chemical compound NCC(C)CO FVXBTPGZQMNAEZ-UHFFFAOYSA-N 0.000 description 1
- AGMZSYQMSHMXLT-UHFFFAOYSA-N 3-aminobutan-1-ol Chemical compound CC(N)CCO AGMZSYQMSHMXLT-UHFFFAOYSA-N 0.000 description 1
- NZWJRYHLFNPHFU-UHFFFAOYSA-N 3-bromo-n-methylpropan-1-amine Chemical compound CNCCCBr NZWJRYHLFNPHFU-UHFFFAOYSA-N 0.000 description 1
- ZTGQZSKPSJUEBU-UHFFFAOYSA-N 3-bromopropan-1-amine Chemical compound NCCCBr ZTGQZSKPSJUEBU-UHFFFAOYSA-N 0.000 description 1
- VOUJQKYOLXSFCM-UHFFFAOYSA-N 3-chloro-n-(3-chloropropyl)propan-1-amine Chemical compound ClCCCNCCCCl VOUJQKYOLXSFCM-UHFFFAOYSA-N 0.000 description 1
- QLHYVFSGYNVMPW-UHFFFAOYSA-N 3-chloro-n-methylpropan-1-amine Chemical compound CNCCCCl QLHYVFSGYNVMPW-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- DBKSSENEKWOVKL-UHFFFAOYSA-N 4-(methylamino)butan-1-ol Chemical compound CNCCCCO DBKSSENEKWOVKL-UHFFFAOYSA-N 0.000 description 1
- DUAXLVGFFDFSAG-UHFFFAOYSA-N 4-amino-2-methylbutan-1-ol Chemical compound OCC(C)CCN DUAXLVGFFDFSAG-UHFFFAOYSA-N 0.000 description 1
- GMGSPPGUTUZUHN-UHFFFAOYSA-N 4-bromo-n-methylbutan-1-amine Chemical compound CNCCCCBr GMGSPPGUTUZUHN-UHFFFAOYSA-N 0.000 description 1
- MVZBYZAIKPPGSW-UHFFFAOYSA-N 4-bromobutan-1-amine Chemical compound NCCCCBr MVZBYZAIKPPGSW-UHFFFAOYSA-N 0.000 description 1
- FLBRLMRCJYHIIY-UHFFFAOYSA-N 4-chloro-n-methylbutan-1-amine Chemical compound CNCCCCCl FLBRLMRCJYHIIY-UHFFFAOYSA-N 0.000 description 1
- OEOOQMSPHMFXJL-UHFFFAOYSA-N 4-chlorobutan-1-amine Chemical compound NCCCCCl OEOOQMSPHMFXJL-UHFFFAOYSA-N 0.000 description 1
- GCAMQFBODZNEGE-UHFFFAOYSA-N 4-chlorobutan-2-amine Chemical compound CC(N)CCCl GCAMQFBODZNEGE-UHFFFAOYSA-N 0.000 description 1
- GZIGHROPGNILHK-UHFFFAOYSA-N 5-(ethylamino)pentan-1-ol Chemical compound CCNCCCCCO GZIGHROPGNILHK-UHFFFAOYSA-N 0.000 description 1
- ZOOPONUAQQEUQX-UHFFFAOYSA-N 5-amino-2,2-dimethylpentan-1-ol Chemical compound OCC(C)(C)CCCN ZOOPONUAQQEUQX-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- SXATVMLYNAKYQJ-UHFFFAOYSA-N 5-chloro-n-methylpentan-1-amine Chemical compound CNCCCCCCl SXATVMLYNAKYQJ-UHFFFAOYSA-N 0.000 description 1
- ZKSVFILTLOPGJC-UHFFFAOYSA-N 5-chloropentan-1-amine Chemical compound NCCCCCCl ZKSVFILTLOPGJC-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31745810P | 2010-03-25 | 2010-03-25 | |
| US61/317,458 | 2010-03-25 | ||
| US13/048,260 US8729138B2 (en) | 2010-03-25 | 2011-03-15 | Mixture of polyfluoroalkylsulfonamido alkyl amines |
| US13/048,260 | 2011-03-15 | ||
| PCT/US2011/029360 WO2011119560A1 (en) | 2010-03-25 | 2011-03-22 | Mixture of polyfluoroalkylsulfonamido alkyl amines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013523646A JP2013523646A (ja) | 2013-06-17 |
| JP2013523646A5 JP2013523646A5 (enExample) | 2014-05-08 |
| JP5843846B2 true JP5843846B2 (ja) | 2016-01-13 |
Family
ID=44655282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501380A Expired - Fee Related JP5843846B2 (ja) | 2010-03-25 | 2011-03-22 | ポリフルオロアルキルスルホンアミドアルキルアミンの混合物 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8729138B2 (enExample) |
| JP (1) | JP5843846B2 (enExample) |
| CN (1) | CN102844298B (enExample) |
| WO (1) | WO2011119560A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8729138B2 (en) * | 2010-03-25 | 2014-05-20 | E I Du Pont De Nemours And Company | Mixture of polyfluoroalkylsulfonamido alkyl amines |
| WO2013172412A1 (ja) * | 2012-05-18 | 2013-11-21 | Dic株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
| WO2016176264A1 (en) | 2015-04-30 | 2016-11-03 | The Chemours Company Tt, Llc | Fluorinated amine complex additives for architectural coatings |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2029262A5 (enExample) * | 1969-01-22 | 1970-10-16 | Ugine Kuhlmann | |
| NL7103340A (enExample) | 1970-03-19 | 1971-09-21 | ||
| US3708538A (en) | 1970-07-29 | 1973-01-02 | Hoechst Ag | N-fluoroalkyl-sulfonamides and process for preparing them |
| BE790518A (fr) * | 1971-10-26 | 1973-04-25 | Bayer Ag | Production et application de perfluoro-alcane-sulfonamides |
| FR2308674A1 (fr) | 1975-04-25 | 1976-11-19 | Ugine Kuhlmann | Nouvelles compositions extinctrices |
| DE2617746C3 (de) | 1975-04-24 | 1978-05-18 | Ugine Kuhlmann | Oberflächenaktives Gemisch mit hoher Ausbreitungsgeschwindigkeit auf Kohlenwasserstoffen zur Brandbekämpfung |
| DE2601375A1 (de) | 1976-01-15 | 1977-07-21 | Bayer Ag | Verfahren zur herstellung von perfluoralkansulfonamidoaminen |
| DE2639473C2 (de) * | 1976-09-02 | 1986-03-27 | Bayer Ag, 5090 Leverkusen | Alkoxylierte Perfluoralkansulfonamide und deren Quaternierungsprodukte, Verfahren zu deren Herstellung und deren Verwendung |
| AU3692278A (en) | 1977-07-05 | 1979-12-13 | Ici Ltd | Fluorochemical surfactants |
| JPS55146173A (en) | 1979-05-02 | 1980-11-14 | Sanyo Chemical Ind Ltd | Fire extinguishing substance |
| FR2477144A1 (fr) | 1980-02-29 | 1981-09-04 | Ugine Kuhlmann | Nouveaux oxydes d'amines a groupement perfluoroalkyle et utilisation de ces produits dans des compositions extinctrices |
| JPS6012892B2 (ja) | 1980-03-14 | 1985-04-04 | 大日本インキ化学工業株式会社 | 含フッ素アミノスルホネ−ト系界面活性剤 |
| EP0049958B1 (en) | 1980-09-30 | 1986-11-05 | Angus Fire Armour Limited | Fire-fighting compositions |
| US4486391A (en) * | 1981-08-25 | 1984-12-04 | Dainippon Ink And Chemicals, Inc. | Separation and recovery of ionic substances by fluorine-containing compound |
| JPS6019256B2 (ja) | 1981-08-31 | 1985-05-15 | 大日本インキ化学工業株式会社 | 水性泡消火剤 |
| JPS6019255B2 (ja) | 1981-08-31 | 1985-05-15 | 大日本インキ化学工業株式会社 | 泡消火剤 |
| JPS6019257B2 (ja) | 1981-09-02 | 1985-05-15 | 大日本インキ化学工業株式会社 | 消火剤 |
| US4921696A (en) | 1982-03-25 | 1990-05-01 | The United States Of America As Represented By The Secretary Of Agriculture | Method for the control of insects |
| JPS5946252A (ja) * | 1982-09-09 | 1984-03-15 | Dainippon Ink & Chem Inc | 含フツ素アミノカルボキシレ−トおよびその製法 |
| FR2609751B1 (fr) | 1987-01-20 | 1996-02-02 | Inst Francais Du Petrole | Utilisation de mousses a base de tensioactifs a groupement perfluore pour ameliorer le balayage au gaz d'une formation petroliere |
| DE3708316A1 (de) | 1987-03-14 | 1988-09-22 | Bayer Ag | Fluorierte alkylamidosulfonate, deren herstellung, deren verwendung als flammschutzmittel und sie enthaltende polycarbonatformmassen |
| JPH05238705A (ja) | 1992-01-14 | 1993-09-17 | Mitsubishi Kasei Corp | 硫酸組成物 |
| JP3217116B2 (ja) | 1992-03-06 | 2001-10-09 | 日産化学工業株式会社 | 低表面張力洗浄用組成物 |
| JPH05275407A (ja) | 1992-03-24 | 1993-10-22 | Mitsubishi Kasei Corp | 硫酸組成物 |
| JPH05275406A (ja) | 1992-03-24 | 1993-10-22 | Mitsubishi Kasei Corp | 硫酸組成物 |
| US6201122B1 (en) | 1992-12-08 | 2001-03-13 | 3M Innovative Properties Company | Fluoroaliphatic radical-containing anionic sulfonamido compounds |
| DE4325485A1 (de) | 1993-07-29 | 1995-02-02 | Bayer Ag | Verfahren zur Herstellung flüssiger Aminaddukte fluorgruppenhaltiger Amide |
| US5514493A (en) | 1995-03-06 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them |
| CN1219886A (zh) | 1996-05-31 | 1999-06-16 | 美国3M公司 | 含有多糖和含氟低聚物表面活性剂的灭火剂 |
| WO1997046283A1 (en) | 1996-06-06 | 1997-12-11 | Minnesota Mining And Manufacturing Company | Fire-fighting agents containing adsorbable fluorocarbon surfactants |
| JP2001525234A (ja) | 1997-12-10 | 2001-12-11 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 吸着性フルオロカーボン界面活性剤を含有する消火剤 |
| FR2787721B1 (fr) | 1998-12-24 | 2001-02-02 | Atochem Elf Sa | Compositions extinctrices |
| EP1088814A1 (de) | 1999-09-29 | 2001-04-04 | MERCK PATENT GmbH | Fluorierte Sulfonamide als schwer entflammbare Lösungsmittel zum Einsatz in elektrochemischen Zellen |
| JP2001297790A (ja) | 2000-04-11 | 2001-10-26 | Matsushita Electric Ind Co Ltd | 非水電解質二次電池 |
| KR100446659B1 (ko) | 2001-05-09 | 2004-09-04 | 주식회사 엘지화학 | 비이온성 계면활성제를 포함하는 전해액과 이를 이용하는리튬이온 전지 |
| DE112004001158T5 (de) | 2003-06-27 | 2007-01-11 | E.I. Du Pont De Nemours And Co., Wilmington | Fluorierte Sulfonamidverbindungen und daraus hergestellte Polymer-Elektrolytmembranen zur Verwendung in elektrochemischen Zellen |
| CN1291764C (zh) | 2003-10-09 | 2006-12-27 | 西南石油学院 | 一种油类快速灭火剂 |
| EP1907343A2 (en) | 2005-07-28 | 2008-04-09 | Great Lakes Chemical Corporation | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| US7541492B2 (en) | 2005-10-26 | 2009-06-02 | Toyota Jidosha Kabushiki Kaisha | Perfluoroalkanesulfonamide compounds |
| DE602007006557D1 (de) | 2006-12-29 | 2010-06-24 | 3M Innovative Properties Co | Langkettige polymethylenhalidtelomere |
| CN101589076B (zh) | 2007-01-19 | 2012-05-23 | 3M创新有限公司 | 氟化表面活性剂及其使用方法 |
| US7728163B2 (en) * | 2007-08-06 | 2010-06-01 | E.I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
| US20090137831A1 (en) | 2007-11-28 | 2009-05-28 | E. I. Du Pont De Nemours And Company | Fluorinated Alkanesulfonic Acid Esters and Amides and Processes for Making and Using the Same |
| US8258341B2 (en) * | 2009-07-10 | 2012-09-04 | E.I. Du Pont De Nemours And Company | Polyfluorosulfonamido amine and intermediate |
| US8729138B2 (en) * | 2010-03-25 | 2014-05-20 | E I Du Pont De Nemours And Company | Mixture of polyfluoroalkylsulfonamido alkyl amines |
| US9168408B2 (en) * | 2010-03-25 | 2015-10-27 | The Chemours Company Fc, Llc | Surfactant composition from polyfluoroalkylsulfonamido alkyl amines |
| US8779196B2 (en) * | 2010-03-25 | 2014-07-15 | E I Du Pont De Nemours And Company | Polyfluoroalkylsulfonamido alkyl halide intermediate |
-
2011
- 2011-03-15 US US13/048,260 patent/US8729138B2/en not_active Expired - Fee Related
- 2011-03-22 JP JP2013501380A patent/JP5843846B2/ja not_active Expired - Fee Related
- 2011-03-22 CN CN201180015903.1A patent/CN102844298B/zh not_active Expired - Fee Related
- 2011-03-22 WO PCT/US2011/029360 patent/WO2011119560A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US8729138B2 (en) | 2014-05-20 |
| CN102844298A (zh) | 2012-12-26 |
| JP2013523646A (ja) | 2013-06-17 |
| WO2011119560A1 (en) | 2011-09-29 |
| US20110233459A1 (en) | 2011-09-29 |
| CN102844298B (zh) | 2015-01-14 |
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