JP5887065B2 - 親水性イオン液体 - Google Patents
親水性イオン液体 Download PDFInfo
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- JP5887065B2 JP5887065B2 JP2011108825A JP2011108825A JP5887065B2 JP 5887065 B2 JP5887065 B2 JP 5887065B2 JP 2011108825 A JP2011108825 A JP 2011108825A JP 2011108825 A JP2011108825 A JP 2011108825A JP 5887065 B2 JP5887065 B2 JP 5887065B2
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- 239000002608 ionic liquid Substances 0.000 title claims description 70
- -1 methanesulfonate ion Chemical class 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- AHKZTVQIVOEVFO-UHFFFAOYSA-N oxide(2-) Chemical compound [O-2] AHKZTVQIVOEVFO-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- 229910052757 nitrogen Inorganic materials 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 45
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 27
- 125000000524 functional group Chemical group 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 26
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- 238000005259 measurement Methods 0.000 description 22
- 229910052717 sulfur Inorganic materials 0.000 description 22
- 125000001453 quaternary ammonium group Chemical group 0.000 description 17
- 150000001450 anions Chemical class 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000012472 biological sample Substances 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- 230000007613 environmental effect Effects 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000012800 visualization Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- AAWZDTNXLSGCEK-UHFFFAOYSA-N 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid Chemical compound OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 231100000209 biodegradability test Toxicity 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002433 hydrophilic molecules Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002001 electrolyte material Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-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
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000156724 Antirhea Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000030788 protein refolding Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<実施例1>
下記式で表される化合物を合成した。
FT-IR(KBr):3360cm-1:O-H伸縮振動 2923cm-1:C-H伸縮振動
1H-NMR (D2O 400MHz): δ 1.24 (t, 3H, CH 3 CH2N+), δ 2.72 (s, 3H, CH 3 SO3 -), δ 3.03 (s, 6H, CH 3 N+), δ 3.38 (q, 4H, CH 2 N+), δ 3.95 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:39.12% H:9.09% N:6.68% S:15.34%
理論値C:39.42% H:8.98% N:6.57% S:15.03%
<実施例2〜14>
下記の表1〜表3に示した実施例2〜14の化合物を、実施例1と同様の合成方法と、表8および表9に記載した配合モル比にて合成した。物性値を下記に示す。
<実施例2>
1H-NMR (D2O 400MHz): δ 1.24 (t, 6H, CH 3 CH2N+), δ 2.72 (s, 3H, CH 3 SO3 -), δ 2.95 (s, 3H, CH 3 N+), δ 3.34 (q, 6H, CH 2 N+), δ 3.93 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:42.10% H:9.40% N:6.04% S:13.90%
理論値C:42.27% H:9.31% N:6.16% S:14.11%
<実施例3>
1H-NMR (D2O 400MHz): δ 2.71 (s, 3H, CH 3 SO3 -), δ 3.11 (s, 9H, CH 3 N+), δ 3.42 (t, 2H, CH 2 N+), δ 3.97 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:36.07% H:8.78% N:7.06% S:15.90%
理論値C:36.16% H:8.60% N:7.03% S:16.09%
<実施例4>
1H-NMR (D2O 400MHz): δ 1.30 (t, 9H, CH 3 CH2N+), δ 2.64 (s, 3H, CH 3 SO3 -), δ 3.22 (m, 8H, CH 2 N+), δ 3.82 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:44.57% H:9.36% N:5.63% S:13.42%
理論値C:44.79% H:9.61% N:5.80% S:13.29%
<実施例5>
1H-NMR (D2O 400MHz): δ 1.20 (t, 6H, CH 3 CH2N+), δ 2.70 (s, 3H, CH 3 SO3 -), δ 3.20 (m, 4H, CH3 CH 2 N+), δ 3.40 (m, 4H, N+ CH 2 CH2OH), δ 3.81 (m, 4H, N+CH2 CH 2 OH).
元素分析:実測値C:41.80% H:9.26% N:5.20% S:12.62%
理論値C:42.00% H:9.01% N:5.44% S:12.46%
<実施例6>
1H-NMR (D2O 400MHz): δ 1.23 (t, 3H, CH 3 CH2N+), δ 2.69 (s, 3H, CH 3 SO3 -), δ 3.23 (m, 2H, CH3 CH 2 N+), δ 3.50 (m, 6H, N+ CH 2 CH2OH), δ 3.91 (m, 6H, N+CH2 CH 2 OH).
元素分析:実測値C:39.25% H:8.67% N:5.00% S:11.52%
理論値C:39.55% H:8.48% N:5.12% S:11.73%
<実施例7>
1H-NMR (D2O 400MHz): δ 1.25 (t, 3H, CH 3 CH2N+), δ 2.94 (s, 3H, CH 3 SO4 -), δ 3.03 (s, 6H, CH 3 N+), δ 3.38 (q, 4H, CH 2 N+), δ 3.95 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:36.39% H:8.65% N:6.00% S:13.52%
理論値C:36.67% H:8.35% N:6.11% S:13.98%
<実施例8>
1H-NMR (D2O 400MHz): δ 1.31 (t, 3H, CH 3 CH2N+), δ 3.07 (s, 6H, CH 3 N+), δ 3.41 (q, 4H, CH 2 N+), δ 3.98 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:35.01% H:7.73% N:6.87%
理論値C:35.15% H:7.87% N:6.83%
<実施例9>
1H-NMR (D2O 400MHz): δ 3.30 (s, 9H, CH 3 N+), δ 3.42 (t, 2H, CH 2 N+), δ 3.97 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:32.42% H:7.89% N:7.68%
理論値C:32.62% H:7.67% N:7.61%
<実施例10>
1H-NMR (D2O 400MHz): δ 3.30 (s, 9H, CH 3 N+), δ 3.42 (t, 2H, CH 2 N+), δ 3.97 (t, 2H, N+CH2 CH 2 OH).
元素分析:実測値C:31.25% H:7.55% N:7.10%
理論値C:31.45% H:7.39% N:7.33%
<実施例11>
1H-NMR (D2O 400MHz): δ 1.21 (t, 6H, CH 3 CH2N+), δ 3.21 (m, 4H, CH3 CH 2 N+), δ 3.43 (m, 4H, N+ CH 2 CH2OH), δ 3.92 (m, 4H, N+CH2 CH 2 OH).
元素分析:実測値C:48.35% H:10.40% N:7.10%
理論値C:48.60% H:10.20% N:7.08%
<実施例12>
1H-NMR (D2O 400MHz): δ 1.19 (t, 6H, CH 3 CH2N+), δ 3.19 (m, 4H, CH3 CH 2 N+), δ 3.44 (m, 4H, N+ CH 2 CH2OH), δ 3.82 (m, 4H, N+CH2 CH 2 OH).
元素分析:実測値C:39.50% H:8.55% N:5.70%
理論値C:39.68% H:8.32% N:5.78%
<実施例13>
1H-NMR (D2O 400MHz): δ 1.19 (t, 6H, CH 3 CH2N+), δ 3.19 (m, 4H, CH3 CH 2 N+), δ 3.44 (m, 4H, N+ CH 2 CH2OH), δ 3.82 (m, 4H, N+CH2 CH 2 OH).
元素分析:実測値C:33.09% H:7.10% N:4.76%
理論値C:33.23% H:6.97% N:4.84%
<実施例14>
1H-NMR (D2O 400MHz): δ 1.23 (t, 3H, CH 3 CH2N+), δ 3.23 (m, 2H, CH3 CH 2 N+), δ 3.50 (m, 6H, N+ CH 2 CH2OH), δ 3.91 (m, 6H, N+CH2 CH 2 OH).
元素分析:実測値C:37.00% H:7.98% N:5.45%
理論値C:37.22% H:7.81% N:5.43%
<実施例15>
下記式で表される化合物を合成した。
FT-IR(KBr):3350cm-1:O-H伸縮振動 2990cm-1:C-H伸縮振動
1H-NMR (D2O 400MHz): δ 1.26 (t, 3H, CH 3 CH2N+), δ 3.02 (s, 6H, CH 3 N+), δ 3.38 (q, 4H, CH 2 N+), δ 3.94 (t, 2H, N+CH2 CH 2 OH).
<実施例16>
下記式で表される化合物を合成した。
FT-IR(KBr):3330cm-1:O-H伸縮振動 2980cm-1:C-H伸縮振動
1580cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.26 (t, 3H, CH 3 CH2N+), δ 1.84 (s, 3H, CH 3 COO-), δ 3.02 (s, 6H, CH 3 N+), δ 3.38 (q, 4H, CH 2 N+), δ 3.94 (t, 2H, N+CH2 CH 2 OH).
13C-NMR (D2O 100MHz): δ 183.09 (CH3 COO-).
元素分析:実測値C:54.00% H:10.98% N:7.60%
理論値C:54.21% H:10.80% N:7.90%
<実施例17>
下記式で表される化合物を合成した。
FT-IR(KBr):3320cm-1:O-H伸縮振動 2985cm-1:C-H伸縮振動
1580cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.23 (t, 3H, CH 3 CH2N+), δ 2.98 (s, 6H, CH 3 N+), δ 3.34 (q, 4H, CH 2 N+), δ 3.95 (m, 2H, N+CH2 CH 2 OH), δ 3.96 (s, 2H, CH 2 COO-).
13C-NMR (D2O 100MHz): δ 177.85 (CH2 COO-).
元素分析:実測値C:49.50% H:10.25% N:6.98%
理論値C:49.72% H:9.91% N:7.25%
<実施例18>
下記式で表される化合物を合成した。
FT-IR(KBr):3464cm-1:O-H伸縮振動 2920cm-1:C-H伸縮振動
1570cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.27 (m, 6H, CH 3 CH2N+,CH 3 CH), δ 3.00 (s, 6H, CH 3 N+), δ 3.34 (q, 4H, CH 2 N+), δ 3.94 (m, 2H, N+CH2 CH 2 OH), δ 4.15 (q, 1H, CH3 CH).
13C-NMR (D2O 100MHz): δ 180.09 (CHCOO-).
元素分析:実測値C:51.82% H:10.50% N:6.56%
理論値C:52.15% H:10.21% N:6.76%
<実施例19>
下記式で表される化合物を合成した。
FT-IR(KBr):3465cm-1:O-H伸縮振動 2920cm-1:C-H伸縮振動
1728cm-1:C=O伸縮振動 1570cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.24 (t, 3H, CH 3 CH2N+), δ 2.99 (s, 6H, CH 3 N+), δ 3.35 (q, 4H, CH 2 N+), δ 3.92 (m, 2H, N+CH2 CH 2 OH), δ 4.49 (s, 2H, CH).
13C-NMR (D2O 100MHz): δ 175.60 (CHCOO-).
元素分析:実測値C:44.65% H:8.22% N:5.04%
理論値C:44.94% H:7.92% N:5.24%
<実施例20>
下記式で表される化合物を合成した。
FT-IR(KBr):3420cm-1:O-H伸縮振動 2920cm-1:C-H伸縮振動
1580cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.24 (t, 3H, CH 3 CH2N+), δ 1.52-1.79 (m, 4H, CCH 2 ), δ 3.04 (s, 6H, CH 3 N+), δ 3.35 (q, 4H, CH 2 N+), δ 3.43 (m, 1H, CH2CHCH), δ 3.64 (m, 1H, CH2 CH), δ 3.82 (m, 2H, N+CH2 CH 2 OH), δ 3.91 (m, 1H, CH2 CH).
13C-NMR (D2O 100MHz): δ 177.82 (CCOO-).
元素分析:実測値C:50.16% H:9.15% N:4.18%
理論値C:50.47% H:8.80% N:4.53%
<実施例21>
下記式で表される化合物を合成した。
FT-IR(KBr):3312cm-1:O-H伸縮振動 2980cm-1:C-H伸縮振動
1589cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.23 (t, 3H, CH 3 CH2N+), δ 3.39 (m, 2H, CH3 CH 2 N+), δ 3.52 (t, 6H, N+ CH 2 CH2OH) , δ 3.86 (t, 6H, N+CH2 CH 2 OH), δ 3.96 (s, 2H, CH 2 COO-).
13C-NMR (D2O 100MHz): δ 178.16 (CH2 COO-).
元素分析:実測値C:47.10% H:9.40% N:5.28%
理論値C:47.42% H:9.15% N:5.53%
<実施例22>
下記式で表される化合物を合成した。
FT-IR(KBr):2961cm-1:C-H伸縮振動 1728cm-1:C=O伸縮振動
1H-NMR (D2O 400MHz): δ 1.35 (t, 3H, CH 3 CH2N+), δ 2.70 (s, 3H, CH 3 SO3 -), δ 2.97 (t, 2H, N+CH2 CH 2 COOH), δ 3.10 (s, 6H, CH 3 N+), δ 3.46 (q, 2H, CH3 CH 2 N+), δ 3.66 (q, 2H, N+ CH 2 CH2COOH).
13C-NMR (D2O 100MHz): δ 171.66 (CH2 COOH).
元素分析:実測値C:39.51% H:8.12% N:5.76% S:12.98%
理論値C:39.82% H:7.94% N:5.80% S:13.29%
<実施例23〜26>
下記の表6に示した実施例23〜26の化合物を、実施例22と同様の合成方法と、表9に記載した配合モル比にて合成した。物性値を下記に示す。
<実施例23>
1H-NMR (D2O 400MHz): δ 1.13 (t, 6H, CH 3 CH2N+), δ 2.64 (s, 3H, CH 3 SO3 -), δ 2.91 (t, 4H, N+CH2 CH 2 COOH), δ 3.11 (s, 4H, CH3 CH 2 N+), δ 3.46 (q, 4H, N+ CH 2 CH2COOH).
13C-NMR (D2O 100MHz): δ 173.77 (CH2 COOH).
元素分析:実測値C:42.00% H:7.56% N:4.60% S:10.50%
理論値C:42.16% H:7.40% N:4.47% S:10.23%
<実施例24>
1H-NMR (D2O 400MHz): δ 1.25 (t, 3H, CH 3 CH2N+), δ 2.72 (s, 3H, CH 3 SO3 -), δ 2.97 (t, 6H, N+CH2 CH 2 COOH), δ 3.28 (s, 2H, CH3 CH 2 N+), δ 3.51 (q, 6H, N+ CH 2 CH2COOH).
13C-NMR (D2O 100MHz): δ 173.80 (CH2 COOH).
元素分析:実測値C:40.05% H:6.56% N:3.70% S:9.20%
理論値C:40.33% H:6.49% N:3.92% S:8.97%
<実施例25>
1H-NMR (D2O 400MHz): δ 1.36 (t, 3H, CH 3 CH2N+), δ 2.74 (s, 3H, CH 3 SO4 -), δ 3.00 (t, 2H, N+CH2 CH 2 COOH), δ 3.11 (s, 6H, CH 3 N+), δ 3.48 (q, 2H, CH3 CH 2 N+), δ 3.70 (q, 2H, N+ CH 2 CH2COOH).
13C-NMR (D2O 100MHz): δ 171.70 (CH2 COOH).
元素分析:実測値C:37.16% H:7.55% N:5.10% S:12.67%
理論値C:37.34% H:7.44% N:5.44% S:12.46%
<実施例26>
1H-NMR (D2O 400MHz): δ 1.18 (t, 6H, CH 3 CH2N+), δ 2.96 (t, 4H, N+CH2 CH 2 COOH), δ 3.15 (s, 4H, CH3 CH 2 N+), δ 3.35 (q, 4H, N+ CH 2 CH2COOH).
13C-NMR (D2O 100MHz): δ 177.21 (CH2 COOH).
元素分析:実測値C:40.30% H:6.70% N:4.67%
理論値C:40.28% H:6.76% N:4.70%
<実施例27>
下記式で表される化合物を合成した。
FT-IR(KBr):3380cm-1:O-H伸縮振動 2980cm-1:C-H伸縮振動
1728cm-1:C=O伸縮振動 1580cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.25 (t, 3H, CH 3 CH2N+), δ 2.79 (m, 2H, N+CH2 CH 2 COOH), δ 2.99 (s, 6H, CH 3 N+), δ 3.33 (m, 2H, CH3 CH 2 N+), δ 3.52 (m, 2H, N+ CH 2 CH2COOH) , δ 4.08 (s, 2H, CH 2 COO-),.
13C-NMR (D2O 100MHz): δ 174.13 (CH2 COO-).
元素分析:実測値C:48.59% H:8.99% N:6.05%
理論値C:48.86% H:8.66% N:6.33%
<比較例1〜8>
表5および表7に示す比較例1〜8の化合物を用意した。比較例5、6の化合物については実施例1に準じた方法により、比較例7、8の化合物については実施例22に準じた方法により合成した。
<実施例28〜36、比較例9〜12>
表10および表11に示す化合物について、生分解性試験を行った。生分解性試験は、OECDテストガイドライン301C法に準拠して行った。この試験には一般活性汚泥を微生物源として使用し、調製した標準試験培養液300mlに、微生物源30mg/l、被験物質100mg/lの濃度になるようにそれぞれ投入し、25±1℃、試験期間28日、標準物質にアニリンを使用して行った。分解率はアクタック製BODセンサーを使用して生化学的酸素要求量(BOD;biochemical oxygen demand)を測定し、算出した理論的酸素要求量の値から分解度を算出した。具体的には、28日間のBOD分解度が60%以上の場合を易分解性として評価した。
Claims (3)
- 下記式(I):
(式中、R1、R2、R3、R4はそれぞれ独立にメチル基およびエチル基から選ばれるいずれかのアルキル基、または−(CH2)2COOHを示し、R1、R2、R3、R4のうち1個が−(CH2)2COOHであり、R1、R2、R3、R4のうち残り3個のアルキル基は、その少なくとも1個が他のアルキル基とは異なる構造である。X-は、メタンスルホネートイオン、メチル硫酸イオン、水酸化物イオン、または、水酸基を有していてもよい炭素数1〜4のモノカルボン酸イオンもしくはジカルボン酸イオン、およびヒドロキシシクロヘキサンカルボン酸イオンから選ばれるいずれかのカルボン酸イオンを示す。)で表される親水性イオン液体。
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