JP5618833B2 - スルホン化合物 - Google Patents
スルホン化合物 Download PDFInfo
- Publication number
- JP5618833B2 JP5618833B2 JP2010537737A JP2010537737A JP5618833B2 JP 5618833 B2 JP5618833 B2 JP 5618833B2 JP 2010537737 A JP2010537737 A JP 2010537737A JP 2010537737 A JP2010537737 A JP 2010537737A JP 5618833 B2 JP5618833 B2 JP 5618833B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfone
- methyl
- group
- solvent
- 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.)
- Expired - Fee Related
Links
- -1 Sulfone compound Chemical class 0.000 title claims description 44
- 241001417524 Pomacanthidae Species 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000002896 organic halogen compounds Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WQRZYMZACUVPND-UHFFFAOYSA-N 3-(methylsulfonylmethyl)heptane Chemical compound CCCCC(CC)CS(C)(=O)=O WQRZYMZACUVPND-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- WLVCBAMXYMWGLJ-UHFFFAOYSA-N 3-(chloromethyl)heptane Chemical compound CCCCC(CC)CCl WLVCBAMXYMWGLJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- DDRHIJAGBUJCEX-UHFFFAOYSA-N 3-methyl-4-(methylsulfonylmethyl)hexane Chemical compound CCC(C)C(CC)CS(C)(=O)=O DDRHIJAGBUJCEX-UHFFFAOYSA-N 0.000 description 2
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
- CLFDVJGVCXTKAU-UHFFFAOYSA-N 4-(methylsulfonylmethyl)heptane Chemical compound CCCC(CCC)CS(C)(=O)=O CLFDVJGVCXTKAU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- UJEGHEMJVNQWOJ-UHFFFAOYSA-N 1-heptoxyheptane Chemical compound CCCCCCCOCCCCCCC UJEGHEMJVNQWOJ-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- GNLXLNIZFZMEKB-UHFFFAOYSA-N 1-iodo-2-methylheptane Chemical compound CCCCCC(C)CI GNLXLNIZFZMEKB-UHFFFAOYSA-N 0.000 description 1
- PFJDVQSHGLRPFC-UHFFFAOYSA-N 1-methylsulfonylheptane Chemical compound CCCCCCCS(C)(=O)=O PFJDVQSHGLRPFC-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- TVOHRKXDNCXIIL-UHFFFAOYSA-N 2,2,3-trimethyl-1-methylsulfonylbutane Chemical compound CC(C)C(C)(C)CS(C)(=O)=O TVOHRKXDNCXIIL-UHFFFAOYSA-N 0.000 description 1
- HVLLPIPSYZYNBU-UHFFFAOYSA-N 2,2,3-trimethyl-1-methylsulfonylpentane Chemical compound CCC(C)C(C)(C)CS(C)(=O)=O HVLLPIPSYZYNBU-UHFFFAOYSA-N 0.000 description 1
- XRUZOCYQQNKMDG-UHFFFAOYSA-N 2,3-dimethyl-1-methylsulfonylbutane Chemical compound CC(C)C(C)CS(C)(=O)=O XRUZOCYQQNKMDG-UHFFFAOYSA-N 0.000 description 1
- GVXAONKWZONECG-UHFFFAOYSA-N 2,3-dimethyl-1-methylsulfonylhexane Chemical compound CCCC(C)C(C)CS(C)(=O)=O GVXAONKWZONECG-UHFFFAOYSA-N 0.000 description 1
- QHZVCPYSKMZLES-UHFFFAOYSA-N 2,3-dimethyl-1-methylsulfonylpentane Chemical compound CCC(C)C(C)CS(C)(=O)=O QHZVCPYSKMZLES-UHFFFAOYSA-N 0.000 description 1
- WRRCHCAQFAKNBG-UHFFFAOYSA-N 2-methyl-1-methylsulfonylheptane Chemical compound CCCCCC(C)CS(C)(=O)=O WRRCHCAQFAKNBG-UHFFFAOYSA-N 0.000 description 1
- YTMMOGHIBCUKQH-UHFFFAOYSA-N 2-methyl-1-methylsulfonylhexane Chemical compound CCCCC(C)CS(C)(=O)=O YTMMOGHIBCUKQH-UHFFFAOYSA-N 0.000 description 1
- QRDIPPIUXYPOPL-UHFFFAOYSA-N 2-methyl-1-methylsulfonylpentane Chemical compound CCCC(C)CS(C)(=O)=O QRDIPPIUXYPOPL-UHFFFAOYSA-N 0.000 description 1
- QNMBWMFUSAHBAG-UHFFFAOYSA-N 2-methyl-3-(methylsulfonylmethyl)hexane Chemical compound CCCC(C(C)C)CS(C)(=O)=O QNMBWMFUSAHBAG-UHFFFAOYSA-N 0.000 description 1
- BFPIGIXSJYDFBF-UHFFFAOYSA-N 2-methyl-3-(methylsulfonylmethyl)pentane Chemical compound CCC(C(C)C)CS(C)(=O)=O BFPIGIXSJYDFBF-UHFFFAOYSA-N 0.000 description 1
- YJWJESDJKNXBJW-UHFFFAOYSA-N 3-(methylsulfonylmethyl)hexane Chemical compound CCCC(CC)CS(C)(=O)=O YJWJESDJKNXBJW-UHFFFAOYSA-N 0.000 description 1
- XCGSFZWSJRXLFD-UHFFFAOYSA-N 3-(methylsulfonylmethyl)pentane Chemical compound CCC(CC)CS(C)(=O)=O XCGSFZWSJRXLFD-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZVWCWXUOSBDXEQ-UHFFFAOYSA-N 4-(bromomethyl)heptane Chemical compound CCCC(CBr)CCC ZVWCWXUOSBDXEQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- YYWKGWBVLPHCFH-UHFFFAOYSA-N CCCS(CC(C)C(C)C)(=O)=O Chemical compound CCCS(CC(C)C(C)C)(=O)=O YYWKGWBVLPHCFH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RZTOWFMDBDPERY-UHFFFAOYSA-N Delta-Hexanolactone Chemical compound CC1CCCC(=O)O1 RZTOWFMDBDPERY-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Primary Cells (AREA)
- Secondary Cells (AREA)
Description
上記電気化学デバイスとしては、例えば、リチウム一次電池、リチウム二次電池、リチウムイオン電池、燃料電池、太陽電池、電気二重層コンデンサ等が挙げられる。
また、本発明のスルホン化合物は、融点が比較的低く、熱的安定性に優れることから、低温から高温まで広い温度範囲で安全に使用することができる。
更に、本発明のスルホン化合物は、粘度が低いことから、電解質のイオン導電性を大幅に高めることができ、高い電気特性を実現することができる。
攪拌機、温度計および冷却器を備え付けた500mL容の四つ口フラスコに窒素雰囲気下で、3−(クロロメチル)ヘプタン74.4g(0.50mol)を仕込み、28%メチルメルカプタンナトリウム水溶液187.8g(0.75mol)を徐々に加え、60℃に維持して2時間攪拌した。これにジクロロメタン50mlを加え10分撹拌した後、ジクロロメタン層を分取し、超純水30mLで1回洗浄した。得られたジクロロメタン層に35%過酸化水素水102.0g(1.05mol)を加え、60℃に維持して2時間攪拌し、ジクロロメタン層を蒸留することにより無色透明液体のメチル2−エチルヘキシルスルホン86.5gを得た。得られたメチル2−エチルヘキシルスルホンの収率は、3−(クロロメチル)ヘプタンに対して90%であった。
元素分析:C 56.2;H 10.5;S 16.7(計算値 C 56.2;H 10.2;S 16.7)
実施例1における融点、発熱開始温度および水の溶解度の測定結果を、比較例1としてのプロピレンカーボネート、比較例2としてのスルホランとともに表1に示す。
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008293703 | 2008-11-17 | ||
JP2008293703 | 2008-11-17 | ||
PCT/JP2009/067792 WO2010055744A1 (ja) | 2008-11-17 | 2009-10-14 | スルホン化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2010055744A1 JPWO2010055744A1 (ja) | 2012-04-12 |
JP5618833B2 true JP5618833B2 (ja) | 2014-11-05 |
Family
ID=42169880
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010537737A Expired - Fee Related JP5618833B2 (ja) | 2008-11-17 | 2009-10-14 | スルホン化合物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8466324B2 (ja) |
EP (1) | EP2360143B1 (ja) |
JP (1) | JP5618833B2 (ja) |
KR (1) | KR101651704B1 (ja) |
CN (1) | CN102216264B (ja) |
TW (1) | TWI438183B (ja) |
WO (1) | WO2010055744A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5645557B2 (ja) * | 2010-09-03 | 2014-12-24 | 住友精化株式会社 | スルホン化合物 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09147913A (ja) * | 1995-11-22 | 1997-06-06 | Sanyo Electric Co Ltd | 非水電解質電池 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57140786A (en) | 1981-02-25 | 1982-08-31 | Sagami Chem Res Center | Preparation of sulfone compound substituted with alpha-silyl group |
JPS62237715A (ja) | 1986-04-08 | 1987-10-17 | 旭硝子株式会社 | 電気二重層キヤパシタ |
US4725927A (en) | 1986-04-08 | 1988-02-16 | Asahi Glass Company Ltd. | Electric double layer capacitor |
JPS6312122A (ja) | 1986-07-03 | 1988-01-19 | 旭硝子株式会社 | 電気二重層コンデンサ |
DE3766567D1 (de) | 1986-08-13 | 1991-01-17 | Seitetsu Kagaku Co Ltd | Verfahren zur herstellung von alkalimetallbenzolsulfinaten. |
JPS6440457A (en) | 1987-08-05 | 1989-02-10 | Seitetsu Kagaku Co Ltd | Production of nitrophenylphenylsulfones |
JPS63239911A (ja) * | 1987-03-27 | 1988-10-05 | 旭硝子株式会社 | 固体電解コンデンサ |
JP2704488B2 (ja) | 1993-12-24 | 1998-01-26 | 住友重機械工業株式会社 | 攪拌方法 |
JPH08143534A (ja) | 1994-11-24 | 1996-06-04 | Sumitomo Seika Chem Co Ltd | アルキルフェニルスルホンの製造方法 |
JP2000103779A (ja) | 1998-09-30 | 2000-04-11 | Sumitomo Seika Chem Co Ltd | アルキルスルホニルベンズアルデヒド類の製造方法 |
KR100458568B1 (ko) * | 2002-04-03 | 2004-12-03 | 삼성에스디아이 주식회사 | 리튬 전지용 전해질 및 이를 포함하는 리튬 전지 |
KR101101001B1 (ko) * | 2005-01-19 | 2011-12-29 | 아리조나 보드 오브 리전트스, 아리조나주의 아리조나 주립대 대행법인 | 술폰계 전해질을 갖는 전류 생성 장치 |
CN100497305C (zh) | 2007-08-06 | 2009-06-10 | 湖南化工研究院 | 乙磺酰基乙腈的制备方法 |
EP2351735A1 (en) * | 2008-10-24 | 2011-08-03 | Sumitomo Seika Chemicals CO. LTD. | Sulfone compound |
US20120136175A1 (en) * | 2009-06-09 | 2012-05-31 | Sumitomo Seika Chemicals Co., Ltd. | Process for preparation of alkyl sulfone compounds |
-
2009
- 2009-10-14 WO PCT/JP2009/067792 patent/WO2010055744A1/ja active Application Filing
- 2009-10-14 US US13/127,892 patent/US8466324B2/en active Active
- 2009-10-14 EP EP09825995.5A patent/EP2360143B1/en not_active Not-in-force
- 2009-10-14 CN CN200980145156.6A patent/CN102216264B/zh not_active Expired - Fee Related
- 2009-10-14 KR KR1020117012138A patent/KR101651704B1/ko active IP Right Grant
- 2009-10-14 JP JP2010537737A patent/JP5618833B2/ja not_active Expired - Fee Related
- 2009-10-22 TW TW098135701A patent/TWI438183B/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09147913A (ja) * | 1995-11-22 | 1997-06-06 | Sanyo Electric Co Ltd | 非水電解質電池 |
Non-Patent Citations (8)
Title |
---|
JPN6009057341; G. Cappozzi et al.: 'Control of Regioselectivity in the Addition of Sulphenyl Chlorides to 3,3-Dimethylbutyne (t-Butylace' J. Chem. Soc. Perkin Trans. I (9), 1982, p.2197-2201 * |
JPN6009057345; A. V. Kuchin et al.: 'Direct synthesis of higher organoaluminum compounds' Zhurnal Obshchei Khimii 50(4), 1980, p.911-916 * |
JPN6014014757; Tetrahedron Letters 26(37), 1985, p.4495-4498 * |
JPN6014014760; Tetrahedron Letters 31(29), 1991, p.3551-3554 * |
JPN6014014761; Journal Medicinal Chemistry 47(19), 2004, p.4741-4754 * |
JPN6014014763; J. Am. Chem. Soc. 100(15), 1978, p.4852-4858 * |
JPN6014025195; Science of Synthesis , 2006, p.1299-1314 * |
JPN6014025198; Synthetic Communications 13(7), 1983, p.553-557 * |
Also Published As
Publication number | Publication date |
---|---|
CN102216264B (zh) | 2014-01-15 |
WO2010055744A1 (ja) | 2010-05-20 |
US8466324B2 (en) | 2013-06-18 |
US20110257438A1 (en) | 2011-10-20 |
JPWO2010055744A1 (ja) | 2012-04-12 |
KR101651704B1 (ko) | 2016-08-26 |
TW201022198A (en) | 2010-06-16 |
TWI438183B (zh) | 2014-05-21 |
KR20110082587A (ko) | 2011-07-19 |
EP2360143B1 (en) | 2017-08-16 |
CN102216264A (zh) | 2011-10-12 |
EP2360143A4 (en) | 2015-06-24 |
EP2360143A1 (en) | 2011-08-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20120136175A1 (en) | Process for preparation of alkyl sulfone compounds | |
JP6145449B2 (ja) | 電気化学デバイス用電解液、アルミニウム電解コンデンサ及び電気二重層コンデンサ | |
WO2010047257A1 (ja) | スルホン化合物 | |
JP5609879B2 (ja) | ビススルホニルイミドアンモニウム塩、ビススルホニルイミドおよびビススルホニルイミドリチウム塩の製造方法 | |
JP5618833B2 (ja) | スルホン化合物 | |
JP2017095416A (ja) | ケイ素含有スルホン酸塩 | |
JPWO2005123656A1 (ja) | 新規なメチルカーボネート類、およびその製造方法、非水系電解液 | |
JP5832315B2 (ja) | 電解液用溶媒、および電気化学デバイス用電解液 | |
JP5645557B2 (ja) | スルホン化合物 | |
JP2004099452A (ja) | イオン性化合物、並びに、これを用いた電解質及び電気化学デバイス | |
JP5022111B2 (ja) | 含フッ素アルコキシアルカンの製造方法 | |
JP5703009B2 (ja) | スルホン化合物、スルホン化合物の製造方法、および電気化学デバイス用電解液 | |
JP2017019746A (ja) | 新規含フッ素鎖状エーテル化合物およびその製造方法、並びにその用途 | |
JP2009084193A (ja) | チアゾリウム塩 | |
JP2013060385A (ja) | 含フッ素アルキルスルホン化合物の製造方法、および電気化学デバイス用電解液 | |
JP4992869B2 (ja) | イオン性化合物、並びに、これを用いた電解質及び電気化学デバイス | |
JP2008113043A (ja) | 電気二重層キャパシタ及びイオン性化合物 | |
JP2016212947A (ja) | ジスルホニルアミド塩およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120920 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140408 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140514 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140617 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140812 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140819 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140909 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140916 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5618833 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |