JP6288618B2 - 両末端にパーフルオロアルキル基を有する新規アロマティック化合物 - Google Patents
両末端にパーフルオロアルキル基を有する新規アロマティック化合物 Download PDFInfo
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- JP6288618B2 JP6288618B2 JP2014043509A JP2014043509A JP6288618B2 JP 6288618 B2 JP6288618 B2 JP 6288618B2 JP 2014043509 A JP2014043509 A JP 2014043509A JP 2014043509 A JP2014043509 A JP 2014043509A JP 6288618 B2 JP6288618 B2 JP 6288618B2
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- 125000005010 perfluoroalkyl group Chemical group 0.000 title description 10
- 150000001491 aromatic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 89
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 64
- 239000007788 liquid Substances 0.000 claims description 51
- 239000001569 carbon dioxide Substances 0.000 claims description 32
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 32
- 238000000926 separation method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 239000012528 membrane Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000002562 thickening agent Substances 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 239000002594 sorbent Substances 0.000 claims description 7
- 125000004149 thio group Chemical group *S* 0.000 claims description 7
- 239000007789 gas Substances 0.000 description 37
- 239000012044 organic layer Substances 0.000 description 33
- 235000002597 Solanum melongena Nutrition 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000499 gel Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000000967 suction filtration Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000003349 gelling agent Substances 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NVVZEKTVIXIUKW-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCI NVVZEKTVIXIUKW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002608 ionic liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 3
- 125000006416 CBr Chemical group BrC* 0.000 description 3
- 239000004695 Polyether sulfone Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920006393 polyether sulfone Polymers 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 2
- FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 2
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PGAPATLGJSQQBU-UHFFFAOYSA-M thallium(i) bromide Chemical compound [Tl]Br PGAPATLGJSQQBU-UHFFFAOYSA-M 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 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
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940018951 carbon dioxide 20 % Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- -1 perfluoro group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000006163 transport media Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
但し、n,mはそれぞれ2〜18の整数;R1,R3はそれぞれ単結合又は炭素数1〜6の分枝又は直鎖状アルキレン基;R2は炭素数3〜18の分枝又は直鎖状アルキレン基;X1,X2はいずれか一方がスルホニル基であり、他方がチオ基を表す。
但し、n,mはそれぞれ2〜18の整数であり、R1,R3はそれぞれ同一又は異なる単結合又は炭素数1〜6の分枝又は直鎖状のアルキレン基で、R2は炭素数3〜18の分枝又は直鎖状アルキレン基である。
(I)分子の両末端にパーフルオロアルキル基が存在すること。
(II)分子中にビフェニレン基とフェニレン基とがアルキレン基にそれぞれエーテル結合を介して直鎖状に連なっていること。
(III)該ビフェニレン基及びフェニレン基は、一方がスルホニル基と結合し、他方がチオ基と結合する非対称であること。
本発明の化合物(2)について、以下のスキームで合成される。
なお、反応式において、1,4-ジオキサンを「Dioxane」と略記する(以下同じ。)。
状態:白色結晶
融点:205〜206℃
収率:77%
収量:6.25g
IR(KBrdisc):
ν=3358(O-H),1601,1580(C=C),1250(>O)cm-1
1HNMR(500MHz,DMSO-d6):
δ=3.76(3H,s),6.88(2H,d,J=8.5Hz),7.73(2H,d,J=8.5Hz),7.85(2H,s)ppm
化合物Dの合成
状態:白色粉末
融点:39〜41℃
収率:96%
収量:32.41g
IR(KBrdisc):
ν=1580,1477(C=C),1248-1140(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.33-2.43(2H,m),3.10(2H,m),7.23(2H,d,J=8.5Hz),7.46(2H,d,J=8.5Hz)ppm
化合物Eの合成
状態:白色粉末
融点:129〜131℃
収率:93%
収量:1.85g
IR(KBrdisc):
ν=1601,1580(C=C),1250(>O),1248-1140(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.33-2.48(2H,m),3.14(2H,m),3.85(3H,s),6.98(2H,d,J=9.2Hz),7.41(2H,d,J=8.5Hz),7.52(2H,d,J=9.2Hz),7.52(2H,d,J=8.5Hz)ppm
化合物Fの合成
状態:白色粉末
融点:171〜172℃
収率:89%
収量:0.87g
IR(KBrdisc):
ν=3445(O-H),1609,1489(C=C),1234-1188(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.37-2.48(2H,m),3.14(2H,m),4.92(1H,s),6.91(2H,d,J=8.5Hz),7.41(2H,d,J=7.9Hz),7.47(2H,d,J=8.5Hz),7.51(2H,d,J=7.9Hz)ppm
化合物Hの合成
状態:白色粉末
融点:69〜71℃
収率:79%
収量:7.85g
IR(KBr):
ν=3431cm-1(O-H)、1591,1496cm-1(C=C)、1236-1141cm-1(C-F)
1HNMR(500MHz,CDCl3):
δ=2.28-2.38(2H,m)、2.99(2H,m,J=8.2Hz)、5.00(1H,s)、6.82(2H,d,J=8.5Hz)、7.34(2H,d,J=8.5Hz)ppm
化合物Iの合成
状態:淡黄色粘性液体から淡黄色固体
融点:32〜35℃
収率:67%
収量:2.72g
IR(KRS-5):
ν=2936,2862(>CH2),1595,1495(C=C),1246-1144(C-F),640-520(C-Br)cm-1
1HNMR(500MHz,CDCl3):
δ=1.49-1.58(6H,m),1.80(2H,quin,J=6.4Hz),1.90(2H,quin,J=6.4Hz),2.28-2.38(2H,m),3.30(2H,m),3.42(2H,t,J=6.7Hz),3.95(2H,t,J=6.7Hz),6.86(2H,d,J=8.5Hz),7.36(2H,d,J=8.5Hz)ppm
化合物Jの合成
状態:白色粉末
融点:64〜66℃
収率:55%
収量:1.98g
IR(KBr):
ν=2939,2868cm-1(-CH2-)、1598,1496cm-1(C=C)、1246-1178cm-1(C-F)、640-520cm-1(C-Br)
1HNMR(500MHz,CDCl3):
δ=1.52-1.58(8H,m)、1.85(2H,quin,J=6.4Hz)、1.91(2H,quin,J=6.4Hz)、2.53-2.63(2H,m)、3.28-3.31(2H,m)、3.43(2H,t,J=6.7Hz)、4.06(2H,t,J=6.4Hz)、7.05(2H,d,J=8.5Hz)、7.85(2H,d,J=8.5Hz)ppm
化合物2の合成
状態:白色粉末
融点:167〜168℃
収率:78%
収量:0.40g
IR(KBrdisc):
ν=2940,2868(>CH2),1597,1499(C=C),1252-1190(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=1.56-1.58(4H,m),1.86(2H,quin,J=6.4Hz),1.88(2H,quin,J=6.4Hz),2.37-2.48(2H,m),2.56-2.63(2H,m),3.14(2H,m),3.29(2H,tt,J=8.2,4.0Hz),4.03(2H,t,J=6.4Hz),4.07(2H,t,J=6.4Hz),6.97(2H,d,J=8.5Hz),7.05(2H,d,J=9.2Hz),7.41(2H,d,J=8.5Hz),7.51(2H,d,J=8.5Hz),7.52(2H,d,J=7.9Hz),7.84(2H,d,J=9.2Hz)ppm
状態:白色粉末
融点:69〜71℃
収率:79%
収量:7.85g
IR(KBr):
ν=3431cm-1(O-H)、1591,1496cm-1(C=C)、1236-1141cm-1(C-F)
1HNMR(500MHz,CDCl3):
δ=2.28-2.38(2H,m)、2.99(2H,m,J=8.2Hz)、5.00(1H,s)、6.82(2H,d,J=8.5Hz)、7.34(2H,d,J=8.5Hz)ppm
化合物Iの合成
状態:淡黄色粘性液体から淡黄色固体
融点:32〜35℃
収率:67%
収量:2.72g
IR(KRS-5):
ν=2936,2862(>CH2),1595,1495(C=C),1246-1144(C-F),640-520(C-Br)cm-1
1HNMR(500MHz,CDCl3):
δ=1.49-1.58(6H,m),1.80(2H,quin,J=6.4Hz),1.90(2H,quin,J=6.4Hz),2.28-2.38(2H,m),3.30(2H,m),3.42(2H,t,J=6.7Hz),3.95(2H,t,J=6.7Hz),6.86(2H,d,J=8.5Hz),7.36(2H,d,J=8.5Hz)ppm
化合物Bの合成
状態:白色結晶
融点:205〜206℃
収率:77%
収量:6.25g
IR(KBrdisc):
ν=3358(O-H),1601,1580(C=C),1250(>O)cm-1
1HNMR(500MHz,DMSO-d6):
δ=3.76(3H,s),6.88(2H,d,J=8.5Hz),7.73(2H,d,J=8.5Hz),7.85(2H,s)ppm
化合物Lの合成
状態:白色粉末
融点:39〜41℃
収率:96%
収量:32.41g
IR(KBrdisc):
ν=1580,1477(C=C),1248-1140(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.33-2.43(2H,m),3.10(2H,m),7.23(2H,d,J=8.5Hz),7.46(2H,d,J=8.5Hz)ppm
化合物Mの合成
状態:白色粉末
融点:127〜129℃
収率:97%
収量:10.22g
IR(KBrdisc):
ν=1578,1390(C=C),1240-1190(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.55-2.65(2H,m),3.33(2H,m),7.77(2H,d,J=8.5Hz),7.81(2H,d,J=8.5Hz)ppm
化合物Nの合成
状態:白色粉末
融点:187〜189℃
収率:99%
収量:4.85g
IR(KBrdisc):
ν=1609,1528(C=C),1249(>O),1233-1140(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=2.58-2.69(2H,m),3.36(2H,m),3.88(3H,s),7.03(2H,d,J=8.5Hz),7.58(2H,d,J=8.5Hz),7.77(2H,d,J=8.5Hz),7.96(2H,d,J=8.5Hz)ppm
化合物Oの合成
状態:白色粉末
融点:207〜209℃
収率:85%
収量:1.65g
IR(KBrdisc):
ν=3445(O-H),1611,1489(C=C),1230-1190(C-F)cm-1
1HNMR(500MHz,DMSO-d6):
δ=2.55-2.66(2H,m),3.72(2H,m),6.90(2H,d,J=8.5Hz),7.64(2H,d,J=8.5Hz),7.90(2H,d,J=8.5Hz),7.98(2H,d,J=8.5Hz),9.82(1H,s)ppm
化合物3の合成
状態:白色粉末
融点:158〜160℃
収率:67%
収量:0.60g
IR(KBrdisc):
ν=2940,2868(>CH2),1597,1497(C=C),1234-1190(C-F)cm-1
1HNMR(500MHz,CDCl3):
δ=1.83(2H,quin,J=6.4Hz),1.86(2H,quin,J=6.4Hz),2.28-2.38(2H,m),2.58-2.69(2H,m),2.99(2H,m),3.35(2H,m),3.98(2H,t,J=6.4Hz),4.04(2H,t,J=6.4Hz),6.87(2H,d,J=8.5Hz),7.01(2H,d,J=8.5Hz),7.37(2H,d,J=8.5Hz),7.57(2H,d,J=8.5Hz),7.77(2H,d,J=8.5Hz),7.96(2H,d,J=8.5Hz)ppm
これらのグラフから、
CO2-[BMIM][TFSA]はy=0.295x、H=3.39MPa
CO2-[BMIM][TFSA]gelはy=0.291x、H=3.44MPa
N2-[BMIM][TFSA]はy=0.01671x、H=59.84MPa
N2-[BMIM][TFSA]gelはy=0.01682x、H=59.45MPa
と計算され、ヘンリー定数の値から各ガスのモル分率は、粘性液体の状態にほぼ無関係のことがわかる。
実施例5に用いた粘性液体組成物(ゲル)を用い、ポリエーテルスルホン(PES)膜(Pall Corporation Supor(登録商標)200;平均孔径0.2μm、膜厚145μm)を支持体として、フロー式ガス透過率測定装置(株式会社ジェイ・サイエンス)を用いて測定した。(フィルター面積22.9cm2)測定ガスは、CO2:N2=20:80の混合ガス(岩谷産業株式会社製)、ガスフローは測定ガス50ml/min。下流側キャリアガスはHeを用い50ml/minで流した。上流側、下流側とも常圧、室温で行った。
Claims (7)
- 下記一般式(1)で表される化合物。
但し、n,mはそれぞれ2〜18の整数;R1,R3はそれぞれ単結合又は炭素数1〜6の分枝又は直鎖状アルキレン基;R2は炭素数3〜18の分枝又は直鎖状アルキレン基;X1,X2はいずれか一方がスルホニル基であり、他方がチオ基を表す。 - 一般式(1)で表される化合物が、下記構造式である請求項1記載の化合物。
但し、n,m,R1,R2,R3は請求項1に同じ。 - 一般式(1)で表される化合物が下記構造式である請求項1記載の化合物。
但し、n,m,R1,R2,R3は請求項1に同じ。 - 請求項1乃至3のいずれかに記載の化合物よりなる増粘剤。
- 請求項1乃至3のいずれかに記載の化合物を0.1〜5重量%含む有機液体よりなる粘性液体組成物。
- 請求項1乃至3のいずれかに記載の化合物と有機液体よりなる炭酸ガス収着剤。
- 請求項6に記載の炭酸ガス収着剤を多孔質膜に塗布してなる炭酸ガス分離膜。
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