Ionic Liquids 2010 - ilra.jp

1 Ionic Liquids 2010 Ionic Liquids What s in it for you with Ionic Liquids from Merck? That's what's in it for you. Merck Chemicals 100 25 g 100 g 500 g Tetracyanoborate (TCB)-Anion (FAP)-Anion P 5 ,3-Dimethylimidazolium [B(CN)4]-Tetracyanoborate ( )

2 TCB TCB / V versus Ag(I) / AgCurrent density [ C ] [g/cm3] *[cP] *[mS/cm]1-Ethyl-3-methylimidazolium tetracyanoborateEMIM tetracyanoborateBMPL *20 C EMIM TCB 4 FAP-Anion [(C2F5)3PF3]-Tris(pentafluoroethyl)trifl uorophosphate [ C ] [g/cm3] *[cP] *[mS/cm]Ethyl-3-methylimidazoliumtris(pe ntafluoroethyl)trifluorophosphateEMIM (tetradecyl)phosphonium tris(pentafluoroethyl)trifluorophosphate PH3 FAP490002< tris(pentafluoroethyl)trifluorophosphate HMIM tris(pentafluoroethyl)trifluorophosphate BMPL tris(pentafluoroethyl)trifluorophosphate BMIM (2-Methoxyethyl)-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate MOEMPL FAP491233< (Methoxyethyl)-1-methylpiperidinium tris(pentafluoroethyl)trifluorophosphate MOEMPIP FAP491234< (2-methoxyethyl)ammonium tris(pentafluoroethyl)trifluorophosphate MOEDEA FAP491235< (2-Methoxyethyl)-4-methylmorpholinium tris(pentafluoroethyl)trifluorophosphate MOEMMO FAP491236< (3-hydroxypropyl)pyridinium tris(pentafluoroethyl)trifluorophosphate POHPYR FAP491237< (2-Hydroxyethyl)-3-methylimidazolium tris(pentafluoroethyl)

3 TrifluorophosphateEOHMIM FAP491238< *20 C 5 3 S (HP) (UP) S HP UP (HPLC, )> 98 %> 99 %> 99 % (NMR) ( )< 1000 ppm< 100 ppm< 10 ppm ( )< 1 %< 100 ppm< 10 ppm S HP UP ( )> 98 %> 99 %> 99 % < 150 ppm< 150 ppm < %< %< % 25 100 500 3 6 1 headgroups3-Methylimidazolium2,3-Dimethy limidazoliumPyridinium1-Methylpyrrolidin iumAmmonium 2 sidechain(s) 3 Fluoroalkylphosphate FAPBis(trifluoromethylsulfonyl)imide NTF (TFSI)

4 Tetracyanoborate TCBT rifluoromethanesulfonate OTFD icyanamide DCNT ricyanomethide TCCT hiocyanate SCNH ydrogensulfate HSO4 Alkylsulfates MSU, ESU, BSU, HSU, OSU, MEESUO xalatoborate BOBM ethanesulfonate MSOT rifluoroacetate ATFT osylate TOST etrafluoroborate BF4 Hexafluorophoshate PF6 Halides Cl, Br, INonaflate NON 13 24 7 Headgroup3-Methylimidazolium AnionSide-chain R1-Methyl-1-Ethyl-1-Propyl-1-Butyl-1-Hex yl-1-Octyl-1-Decyl-1-Cyanomethyl-1-(2-Hy droxyethyl)-shortnameMMIMEMIMPMIMBMIMHMI MOMIMDMIMMCNMIMEOHMIM[(C2F5)3PF3]-FAP490 001490232490078491238[N(SO2CF3)2]-NTF490 189490228490092490031490246490263[CF3SO3 ]-OTF490061490024[B(CN)4]-TCB49023149023 9[N(CN)2]-DCN490163490015[C(CN)3]-TCC490 330[SCN]-SCN490201[HSO4]-HSO449022349023 0[CH3SO4]-MSU490059490175490063[C2H5SO4] -ESU490229[C4H9SO4]-BSU490291[C6H13SO4]- HSU490292[C8H17SO4]-OSU490205490177[C5H1 1O2SO4]-MEESU490290[B(C2O4)2]-BOB490012[ CH3SO3]-MSO490286490287[CF3 COO]-ATF490147490158[CH3C6H4SO3]-TOS4901 76[BF4]-BF4490037490049490064[PF6]-PF649 0050490065CI-Cl490054490079490039490056B r-Br490038490087490285I-I491304491336490 202490187[C4F9SO3]-NON3-Methylimidazoliu m 8 Cation Headgroup2,3- DimethylimidazoliumAnionSide-chain R1-Methyl-1-Ethyl-1-Propyl-1-Butyl-short name MMMIMEMMIMPMMIMBMMIM[(C2F5)3PF3]-FAP[N(S O2CF3)]

5 2]-NTF490227[CF3SO3]-OTF490115[B(CN)4]-T CB[N(CN)2]-DCN[C(CN)3]-TCC[SCN]-SCN[HSO4 ]-HSO4[CH3SO4]-MSU[C2H5SO4]-ESU[C4H9SO4] -BSU[C6H13SO4]-HSU[C8H17SO4]-OSU[C5H11O2 SO4]-MEESU[B(C2O4)2]-BOB[CH3SO3]-MSO[CF3 COO]-ATF[CH3C6H4SO3]-TOS[BF4]-BF4490016[ PF6]-PF6490035CI-Cl490168490021Br-BrI-I4 90204490191[C4F9SO3]-NON2,3- Dimethylimidazolium9 HeadgroupPyridiniumAnionSide-chains R,R'N-Butyl-N-Ethyl-3-methyl-N-Butyl-3-m ethyl-N-(3-Hydroypropyl)-N-Hexyl-4-(dime thylamino)- N-Ethyl-3-hydroxymethyl-shortnameBPYRE3 MPYRB3 MPYRPOHPYRHDMAPEHMP[(C2F5)3PF3]-FAP48123 7[N(SO2CF3)2]-NTF490264490248[CF3SO3]-OT F490146[B(CN)4]-TCB[N(CN)2]-DCN490331[C( CN)3]-TCC[SCN]-SCN[HSO4]-HSO4[CH3SO4]-MS U[C2H5SO4]-ESU490298490297[C4H9SO4]-BSU[ C6H13SO4]-HSU[C8H17SO4]-OSU[C5H11O2SO4]- MEESU[B(C2O4)2]-BOB[CH3SO3]-MSO[CF3 COO]-ATF[CH3C6H4SO3]-TOS[BF4]-BF4490122[ PF6]-PF6490206CI-Cl490042Br-Br490088I-I[ C4F9SO3]-NON490295101-Methylpyrrolidiniu mCation Headgroup1-MethylpyrrolidiniumAnionSide- chain R N-Methyl-N-Butyl-N-(2-Methoxyethyl)-shor tnameMMPLBMPLMOEMPL[(C2F5)3PF3]-FAP49008 4491233[N(SO2CF3)2]-NTF490046490267[CF3S O3]-OTF490029[B(CN)4]-TCB490123[N(CN)2]- DCN490044[C(CN)3]-TCC[SCN]-SCN[HSO4]-HSO 4[CH3SO4]-MSU[C2H5SO4]-ESU[C4H9SO4]-BSU[ C6H13SO4]-HSU[C8H17SO4]-OSU[C5H11O2SO4]- MEESU[B(C2O4)

6 2]-BOB491211[CH3SO3]-MSO[CF3 COO]-ATF[CH3C6H4SO3]-TOS[BF4]-BF4[PF6]-P F6CI-Cl490028Br-Br490195I-I490203[C4F9SO 3]-NON11 HeadgroupAmmonium N (R, R',R'',R''')AnionR, R',R'',R'''Tetramethyl-Tetrabutyl-Ethyl- dimethyl-propyl-Ethyl-dimethyl-2-methoxy ethyl-shortnameNM4NB4 NEMMPMOEDEA[(C2F5)3PF3]-FAP490025491235[ N(SO2CF3)2]-NTF490140490222[CF3SO3]-OTF[ B(CN)4]-TCB[N(CN)2]-DCN[C(CN)3]-TCC[SCN] -SCN[HSO4]-HSO4[CH3SO4]-MSU[C2H5SO4]-ESU [C4H9SO4]-BSU[C6H13SO4]-HSU[C8H17SO4]-OS U[C5H11O2SO4]-MEESU[B(C2O4)2]-BOB[CH3SO3 ]-MSO[CF3 COO]-ATF[CH3C6H4SO3]-TOS[BF4]-BF4[PF6]-P F6CI-ClBr-BrI-I[C4F9SO3]-NON12 MiscellaneousAnionCationGuanidiniumN-(Me thoxyethyl)-N- methylmorpholinium1-(2-Methoxyethyl)-1-m ethyl-piperidiniumTrihexyl(tetradecyl)- phosphoniumTriethylsulfoniumshortnameGUA MOEMMOMOEMPIPPH3 TSE3[(C2F5)3PF3]-FAP49013549123649123449 0002[N(SO2CF3)2]-NTF49026849026949000849 0296[CF3SO3]-OTF[B(CN)4]-TCB[N(CN)2]-DCN [C(CN)3]-TCC[SCN]-SCN[HSO4]-HSO4[CH3SO4] -MSU[C2H5SO4]-ESU[C4H9SO4]-BSU[C6H13SO4] -HSU[C8H17SO4]-OSU[C5H11O2SO4]-MEESU[B(C 2O4)2]-BOB[CH3SO3]-MSO[CF3 COO]-ATF[CH3C6H4SO3]-TOS[BF4]-BF4[PF6]-P F6CI-ClBr-BrI-I[C4F9SO3]-NON13 : 490001 - 4900241-Ethyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate 490001S EMIM FAP491001HP CAS-No.

7 : 377739-43-0M: g/molmp: -1 CTrihexyl(tetradecyl)phosphonium tris(pentafluoroethyl)trifluorophosphate 490002S PH3T FAP491002HP CAS-No.: 883860-35-3M: g/molmp: < - 50 CTrihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide490008S PH3T NTFCAS-No.: 460092-03-9M: g/molmp: < - 50 C1-Ethyl-3-methylimidazolium bis[oxalato(2-)-O,O ]borate490012S EMIM BOBCAS-No.: 376650-06-5M: g/molmp: 60 C1-Butyl-3-methylimidazolium dicyanamide490015S BMIM DCNCAS-No.: 448245-52-1M: g/molmp: < - 50 C1-Butyl-2,3-dimethylimidazolium tetrafluoroborate490016S BMMIM BF4 CAS-No.: 402846-78-0M: g/molmp: 40 C 1-Butyl-2,3-dimethylimidazolium chloride490021S BMMIM CLCAS-No.: 98892-75-2M: g/molmp: 99 C1-Butyl-3-methylimidazolium trifluoromethanesulfonate490024S BMIM OTF491024HP CAS-No.

8 : 174899-66-2M: g/molmp: 17 C14 : 490025 - 490039 Tetramethylammonium tris(pentafluoroethyl)trifluorophosphate 490025S NM4 FAPCAS-No.: 394692-83-2M: g/molmp: 115 CN-Butyl-1-methylpyrrolidinium chloride490028S BMPL CLCAS-No.: 479500-35-1M: g/molmp: 106 CN-Butyl-1-methylpyrrolidinium trifluoromethanesulfonate490029S BMPL OTF491029HP CAS-No.: 367522-96-1M: g/molmp: 3 C1-Hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide490031S HMIM NTF491031HP CAS-No.: 382150-50-7 M: g/molmp: - 9 C1-Butyl-2,3-dimethylimidazolium hexafluorophosphate490035S BMMIM PF6 CAS-No.: 227617-70-1M: g/molmp: 42 C1-Ethyl-3-methylimidazolium tetrafluoroborate490037S EMIM BF4 CAS-No.: 143314-16-3M: g/molmp: 14 C1-Ethyl-3-methylimidazolium bromide490038S EMIM BRCAS-No.

9 : 65039-08-9M: g/molmp: 65 C1-Hexyl-3-methylimidazolium chloride490039S HMIM CLCAS-No.: 171058-17-6M: g/molmp: < - 50 C15 : 490042 - 490059N-Butylpyridinium chloride490042S BPYR CLCAS-No.: 1124-64-7M: g/molmp: 127 CN-Butyl-1-methylpyrrolidinium dicyanamide490044S BMPL DCN491044HP CAS-No.: 370865-80-8M: g/molmp: < - 50 CN-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide490046S BMPL NTF491046HP CAS-No.: 223437-11-4492046UP M: g/molmp: - 6 C1-Butyl-3-methylimidazolium tetrafluoroborate490049S BMIM BF4491049HP CAS-No.: 174501-65-6M: g/molmp: < - 50 C1-Butyl-3-methylimidazolium hexafluorophosphate490050S BMIM PF6491050HP CAS-No.: 174501-64-5M: g/molmp: 12 C1-Ethyl-3-methylimidazolium chloride490054S EMIM CLCAS-No.

10 : 65039-09-0M: g/molmp: 88 C3-Methyl-1-octylimidazolium chloride490056S OMIM CICAS-No.: 64697-40-1M: g/molmp: - 55 C1,3-Dimethylimidazolium methylsulfate490059S MMIM MSUCAS-No.: 97345-90-9M: g/molmp: 45 C16 : 490061 - 4900871-Ethyl-3-methylimidazolium trifluoromethanesulfonate490061S EMIM OTF491061HP CAS-No.: 145022-44-2M: g/molmp: - 12 C1-Butyl-3-methylimidazolium methylsulfate490063S BMIM MSUCAS-No.: 401788-98-5M: : 13 C1-Hexyl-3-methylimidazolium tetrafluoroborate490064S HMIM BF4 CAS-No.: 244193-50-8M: g/molmp: < - 50 C1-Hexyl-3-methylimidazolium hexafluorophosphate490065S HMIM PF6 CAS-No.: 304680-35-1M: g/molmp: - 68 C1-Hexyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate 490078S HMIM FAP491078HP CAS-No.