WO2010055744A1 - スルホン化合物 - Google Patents
スルホン化合物 Download PDFInfo
- Publication number
- WO2010055744A1 WO2010055744A1 PCT/JP2009/067792 JP2009067792W WO2010055744A1 WO 2010055744 A1 WO2010055744 A1 WO 2010055744A1 JP 2009067792 W JP2009067792 W JP 2009067792W WO 2010055744 A1 WO2010055744 A1 WO 2010055744A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sulfone
- methyl
- formula
- group
- solvent
- Prior art date
Links
- -1 Sulfone compound Chemical class 0.000 title claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 21
- 238000002844 melting Methods 0.000 abstract description 11
- 230000008018 melting Effects 0.000 abstract description 11
- 239000002798 polar solvent Substances 0.000 abstract description 6
- 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 15
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- WQRZYMZACUVPND-UHFFFAOYSA-N 3-(methylsulfonylmethyl)heptane Chemical compound CCCCC(CC)CS(C)(=O)=O WQRZYMZACUVPND-UHFFFAOYSA-N 0.000 description 7
- 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
- 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 239000003792 electrolyte 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
- 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
- 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
- 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
- 239000007788 liquid Substances 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
- 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
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-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
- 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
- 239000008151 electrolyte solution Substances 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
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 150000002576 ketones Chemical class 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
- 150000003457 sulfones Chemical class 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
- 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
Definitions
- the present invention relates to a sulfone compound. More specifically, the present invention relates to a sulfone compound that is mainly useful as a solvent for electrochemical devices.
- Sulfone compounds are used as extraction solvents and various reaction solvents, while those having a high dielectric constant are also used as aprotic polar solvents and as solvents for electrochemical devices.
- an electric double layer capacitor using a sulfolane derivative such as sulfolane or 3-methylsulfolane as an electrolyte Patent Document 1
- Patent Document 2 using a solvent as an electrolytic solution has been proposed.
- An aprotic polar solvent used as a solvent for an electrochemical device or the like is generally desired to have a low melting point and excellent thermal stability.
- the presence of moisture in the system may be a problem, and in that case, a solvent having low water solubility is preferably used.
- Patent Document 1 and Patent Document 2 have a relatively high melting point, there are problems such as a decrease in function in a low-temperature environment. Moreover, the propylene carbonate used together with these has problems such as poor thermal stability and relatively high solubility in water.
- JP-A-62-237715 Japanese Unexamined Patent Publication No. Sho 63-12122
- An object of the present invention is to provide an aprotic polar solvent having a relatively low melting point and excellent thermal stability.
- the present invention relates to a sulfone compound represented by the following formula (1).
- R 1 represents a branched alkyl group having 6 to 8 carbon atoms.
- Examples of the branched alkyl group having 6 to 8 carbon atoms represented by R 1 include a methylpentyl group, a dimethylbutyl group, an ethylbutyl group, a methylhexyl group, a dimethylpentyl group, an ethylpentyl group, a trimethylbutyl group, and ethylmethyl.
- sulfone compound of the present invention represented by the formula (1) include, for example, methyl 2-methylpentyl sulfone, methyl 2,3-dimethylbutyl sulfone, methyl 2-ethylbutyl sulfone, methyl 2-methylhexyl sulfone.
- the branched alkyl group represented by R 1 in the formula (1) preferably has 8 carbon atoms from the viewpoint of relatively low melting point and relatively low water solubility.
- Methyl heptyl sulfone, methyl 2-propylpentyl sulfone and methyl 2-ethylhexyl sulfone are more preferable, and methyl 2-ethylhexyl sulfone is more preferable.
- the sulfone compound represented by the formula (1) is obtained by reacting an organic halogen compound represented by the formula (2) with a sodium salt of methanethiol to form a sulfide compound represented by the formula (3).
- This can be produced by oxidizing with an oxidizing agent.
- R 1 represents a branched alkyl group having 6 to 8 carbon atoms
- X represents a halogen atom
- R 1 represents the same group as R 1 in Formula (2).
- organic halogen compound represented by the formula (2) and the sodium salt of methanethiol commercially available products can be used.
- organic halogen compound examples include 2- (iodomethyl) heptane, 4- (bromomethyl) heptane and 3- (chloromethyl) heptane.
- the use ratio of the sodium salt of methanethiol is 0.5 to 10 mol with respect to 1 mol of the organic halogen compound. It is preferably 1.0 to 5 mol.
- a solvent may not be used, but it may be used as necessary, for example, when the raw material is a solid or the viscosity of the reaction solution is high and stirring is insufficient.
- the solvent to be used is not particularly limited, but for example, methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, cyclohexanol, Alcohols such as ethylene glycol and propylene glycol, diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, dihexyl ether, diheptyl ether, dioctyl ether, tetrahydrofuran, ethers such as tetrahydropyran and 1,4-dioxane, acetonitrile, Nitriles such as acrylonitrile and propionitrile, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketone
- the amount of the solvent used is not particularly limited, but is preferably 100 to 5000 parts by weight with respect to 100 parts by weight of the organic halogen compound.
- the reaction temperature is preferably 0 to 200 ° C, more preferably 10 to 150 ° C.
- the reaction time is usually 1 to 30 hours.
- oxidizing agent used for the oxidation of the sulfide compound represented by the formula (3) are not particularly limited.
- potassium permanganate, chromium Examples include acids, oxygen, aqueous hydrogen peroxide, and organic oxides such as 3-chloroperbenzoic acid.
- hydrogen peroxide water is preferably used.
- the ratio of the oxidizing agent used is preferably 1.8 to 10 moles, more preferably 2 to 5 moles per mole of the sulfide compound.
- the solvent may not be used, but may be used as necessary, for example, when the raw material is solid or the reaction solution has a high viscosity and stirring is insufficient.
- the solvent to be used is not particularly limited.
- halogenation such as carbon tetrachloride, chloroform, dichloromethane, bromopropane, bromobutane, bromopentane, bromohexane, methyl iodide, ethyl iodide and propyl iodide.
- Alkenes such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, petroleum ether, benzine, kerosene, toluene, xylene, mesitylene and benzene, etc. And hydrocarbons, and water. Of these, alkyl halides and water are preferably used. These solvents may be used alone or in combination of two or more.
- the amount of the solvent used is not particularly limited, but is preferably 100 to 5000 parts by weight with respect to 100 parts by weight of the sulfide compound.
- the reaction temperature is preferably 0 to 200 ° C, more preferably 10 to 150 ° C.
- the reaction time is usually 1 to 30 hours.
- the sulfone compound thus obtained can be isolated by distillation after water washing and liquid separation as necessary.
- the sulfone compound of the present invention can be suitably used, for example, as a solvent for electrochemical devices such as an electrolyte solvent.
- electrochemical devices such as an electrolyte solvent.
- the electrochemical device include a lithium primary battery, a lithium secondary battery, a lithium ion battery, a fuel cell, a solar cell, and an electric double layer capacitor.
- the sulfone compound of the present invention is characterized by low water solubility. Thereby, when it uses for the said solvent for electrochemical devices, mixing of water can be suppressed and generation
- the sulfone compound of the present invention has a relatively low melting point and excellent thermal stability, it can be safely used in a wide temperature range from a low temperature to a high temperature.
- the sulfone compound of the present invention has a low viscosity, the ionic conductivity of the electrolyte can be greatly increased, and high electrical characteristics can be realized.
- the sulfone compound of the present invention is an aprotic polar solvent having a relatively low melting point, excellent thermal stability, and low water solubility, and is therefore mainly useful as a solvent for electrochemical devices. It is.
- Example 1 Synthesis of methyl 2-ethylhexyl sulfone (MEHS)] In a 500 mL four-necked flask equipped with a stirrer, a thermometer and a cooler, 74.4 g (0.50 mol) of 3- (chloromethyl) heptane was charged under a nitrogen atmosphere, and 187.8 g of a 28% aqueous solution of methyl mercaptan 18% (0.75 mol) was gradually added, and the mixture was maintained at 60 ° C. and stirred for 2 hours. After adding 50 ml of dichloromethane to this and stirring for 10 minutes, the dichloromethane layer was separated and washed once with 30 mL of ultrapure water.
- MEHS 2-ethylhexyl sulfone
- the melting point and exothermic start temperature of the obtained methyl 2-ethylhexyl sulfone were measured using a differential scanning calorimeter in a nitrogen atmosphere. Furthermore, the solubility of water was determined by measuring the water content of the sulfone compound in which water was saturated and dissolved, using a Karl Fischer coulometric titrator.
- methyl 2-ethylhexyl sulfone could be identified from the following physical properties.
- an aprotic polar solvent having a relatively low melting point which is mainly useful for a solvent for an electrochemical device and the like and excellent in thermal stability.
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Abstract
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 (2)
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US13/127,892 US8466324B2 (en) | 2008-11-17 | 2009-10-14 | Sulfone compound |
JP2010537737A JP5618833B2 (ja) | 2008-11-17 | 2009-10-14 | スルホン化合物 |
EP09825995.5A EP2360143B1 (en) | 2008-11-17 | 2009-10-14 | Sulfone compounds for use as solvent for electrochemical devices |
CN200980145156.6A CN102216264B (zh) | 2008-11-17 | 2009-10-14 | 砜化合物 |
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US (1) | US8466324B2 (ja) |
EP (1) | EP2360143B1 (ja) |
JP (1) | JP5618833B2 (ja) |
KR (1) | KR101651704B1 (ja) |
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JP2012051857A (ja) * | 2010-09-03 | 2012-03-15 | Sumitomo Seika Chem Co Ltd | スルホン化合物 |
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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 |
JPH06312122A (ja) | 1993-12-24 | 1994-11-08 | Sumitomo Heavy Ind Ltd | 攪拌機 |
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JPS57140786A (en) | 1981-02-25 | 1982-08-31 | Sagami Chem Res Center | Preparation of sulfone compound substituted with alpha-silyl group |
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 |
US4725927A (en) | 1986-04-08 | 1988-02-16 | Asahi Glass Company Ltd. | Electric double layer capacitor |
JPS6440457A (en) | 1987-08-05 | 1989-02-10 | Seitetsu Kagaku Co Ltd | Production of nitrophenylphenylsulfones |
DE3766567D1 (de) | 1986-08-13 | 1991-01-17 | Seitetsu Kagaku Co Ltd | Verfahren zur herstellung von alkalimetallbenzolsulfinaten. |
JPS63239911A (ja) | 1987-03-27 | 1988-10-05 | 旭硝子株式会社 | 固体電解コンデンサ |
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 |
JPH09147913A (ja) * | 1995-11-22 | 1997-06-06 | Sanyo Electric Co Ltd | 非水電解質電池 |
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 |
EP1842250B1 (en) * | 2005-01-19 | 2013-09-04 | Arizona Board of Regents, acting for and on behalf of Arizona State University | Electric current-producing device having a sulfone-based electrolyte |
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 |
JPWO2010047257A1 (ja) * | 2008-10-24 | 2012-03-22 | 住友精化株式会社 | スルホン化合物 |
JPWO2010143578A1 (ja) * | 2009-06-09 | 2012-11-22 | 住友精化株式会社 | アルキルスルホン化合物の製造方法 |
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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 |
JPH06312122A (ja) | 1993-12-24 | 1994-11-08 | Sumitomo Heavy Ind Ltd | 攪拌機 |
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EP2360143B1 (en) | 2017-08-16 |
TWI438183B (zh) | 2014-05-21 |
TW201022198A (en) | 2010-06-16 |
US8466324B2 (en) | 2013-06-18 |
CN102216264A (zh) | 2011-10-12 |
JP5618833B2 (ja) | 2014-11-05 |
EP2360143A4 (en) | 2015-06-24 |
CN102216264B (zh) | 2014-01-15 |
KR20110082587A (ko) | 2011-07-19 |
EP2360143A1 (en) | 2011-08-24 |
JPWO2010055744A1 (ja) | 2012-04-12 |
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US20110257438A1 (en) | 2011-10-20 |
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