Boyan Iliev, Marcin Smiglak, Anna Świerczyńska, Thomas Schubert. IOLITEC Ionic Liquids Technologies GmbH Salzstraße 184 D Heilbronn
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1 ILSEPT, Sitges, Spain, September 6th Boyan Iliev, Marcin Smiglak, Anna Świerczyńska, Thomas Schubert IOLITEC Ionic Liquids Technologies GmbH Salzstraße 184 D Heilbronn
2 Outline 1 Introduction 2 Solubility Tests 3 Conclusions 4 Company Information
3 1 Introduction COSMOLOGIC 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
4 Ionic Liquids An Overview of Applications STATUS: PROCESS TECHNOLOGY Biomass Conversion Gas-Separation Metal-Extraction Liquid-Liquid-Extraction FUNCTIONAL FLUIDS & ADDITIVES Hydraulic Oils Additives Lubricants Surfactants SYNTHESIS & CATALYSIS Enzymatic Reactions Immobilization of Catalysts (SILP) Nanoparticle-Synthesis Organic Synthesis R&D Pilot Commercialized IONIC LIQUIDS PROPERTIES - Liquid over a Wide T-Range -Thermal Stability - Electrochemical Stability - Low Vapor Pressure - Non Volatility - Non Inflammability - Electric Conducting - Tunable Miscibility HEAT TRANSPORT & CONVERSION Thermal Fluids Phase Changing Materials (PCM) Sorption Cooling Media ANALYTICS Electrophoresis Solvents for GC- Headspace Matrix-Materials for MALDI-TOF-MS Karl-Fischer Titration Protein-Crystallization GC-Materials ELECTROCHEMISTRY Fuel Cells Metal Deposition & Electropolishing Batteries DSSCs Electrochromic Windows Sensors Supercaps
5 Solubility of ILs in Common Solvents Why Bother? Most publications target only a few ILs (in particular BMIM PF 6 and BMIM BF 4 ) and use specific solvents or solvent mixtures Recycling of ILs is usually associated with extraction Process optimization in extraction/separation processes Production scale-up Green process evaluation A more precise knowledge of the solubility of ILs in common organic solvents is needed to enable more applications in organic synthesis
6 Cations, Anions and Abbreviations N N F F F P F F F F F B F F Me Bu BMPyrr Bu BuPy Me NC PF 6 BF 4 O N S S N F 3 C O O CN DCA BTA O CF 3 O O Me N N Bu N Bu MeO P O OMe EtO P O OEt BMIM Bu3Pic DEP DMP I S C N
7 2 Solubility Tests COSMOLOGIC 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
8 ILs Used in the Study Acetone Ethyl Acetate Water THF Chloroform Toluene Hexane Octane Octanol 1 DiMIM DMP 2 EMIM DEP 3 EMIM OAc 4 EMIM SCN 5 PMIM I 6 BMIM PF6 7 HMIM PF6 8 EMIM BF4 9 BMIM BF4 10 HMIM BF4 11 BuPy BF4
9 ILs Used in the Study (2) Acetone Ethyl Acetate Water THF Chloroform Toluene Hexane Octane Octanol 12 Bu3Pic BF4 13 EMIM BTA 14 BMIM BTA 15 BDiMIM BTA 16 HMIM BTA 17 BuPy BTA 18 Bu3Pic BTA 19 PMPyrr BTA 20 BMPyrr BTA 21 BMIM DCA 22 EMIM DCA
10 Solubility in Hexane Solubility in Hexane Hexane concentration in IL Phase IL concentration in Hexane Phase 25,00 20,00 15,00 10,00 5,00 Organic substance's content 0,00 BMIM DCA EMIM DEP DiMIM DMP EMIM DCA EMIM OAc EMIM SCN PMIM I BMIM PF6 HMIM PF6 EMIM BF4 BMIM BF4 HMIM BF4 BuPy BF4 Bu3Pic BF4 EMIM BTA BMIM BTA BdiMIM BTA HMIM BTA BuPy BTA Bu3Pic BTA PMPyrr BTA BMPyrr BTA
11 Solubility in Toluene Solubility in Toluene Toluene concentration in IL Phase IL concentration in Toluene Phase Organic substance's content 5 0 DiMIM DMP EMIM DCA EMIM OAc EMIM SCN PMIM I BMIM PF6 HMIM PF6 EMIM BF4 BMIM BF4 HMIM BF4 BuPy BF4 Bu3Pic BF4 EMIM BTA BMIM BTA BdiMIM BTA HMIM BTA BuPy BTA Bu3Pic BTA PMPyrr BTA BMPyrr BTA BMIM DCA EMIM DEP
12 Solubility in Ethyl Acetate Solubility in Ethyl Acetate Ethyl Acetate concentration in IL Phase IL concentration in Ethyl Acetate Phase Organic substance's content DiMIM DMP EMIM DCA EMIM OAc EMIM SCN PMIM I EMIM BF4 BMIM BF4 BuPy BF4 Bu3Pic BF4 BMIM DCA EMIM DEP
13 Solubility in Water Solubility in Water Water concentration in IL Phase IL concentration in Water Phase Researched substance's conten 0 BMIM PF6 HMIM PF6 HMIM BF4 EMIM BTA BMIM BTA BdiMIM BTA HMIM BTA BuPy BTA Bu3Pic BTA PMPyrr BTA BMPyrr BTA
14 Solubility in THF Solubility in THF THF concentration in IL Phase IL concentration in THF Phase Organic substance's content DiMIM DMP EMIM DCA EMIM OAc EMIM SCN PMIM I EMIM BF4 BMIM BF4 BuPy BF4 Bu3Pic BF4 EMIM DEP
15 Solubility in n-octane Solubility in Octane Octane concentration in IL IL concentration in Octane Organic substance's content 5 0 DiMIM DMP EMIM DCA EMIM OAc EMIM SCN PMIM I BMIM PF6 HMIM PF6 EMIM BF4 BMIM BF4 HMIM BF4 BuPy BF4 Bu3Pic BF4 EMIM BTA BMIM BTA BdiMIM BTA HMIM BTA BuPy BTA Bu3Pic BTA PMPyrr BTA BMPyrr BTA BMIM DCA EMIM DEP
16 Solubility in 1-Octanol Solubility of 1-Octanol Octanol concentration in IL Phase IL concentration in Octanol Phase Organic substance's content 5 0 EMIM SCN BMIM PF6 HMIM PF6 EMIM BF4 BMIM BF4 BuPy BF4 Bu3Pic BF4 EMIM BTA BMIM BTA BdiMIM BTA HMIM BTA BuPy BTA Bu3Pic BTA PMPyrr BTA BMPyrr BTA
17 Solubility of 1,3-Dimethylimidazolium Dimethylphosphate Solubility of 1,3-Dimethylimidazolium Dimethylphosphate Solvent cocentration in IL Phase IL concentration in Solven Phase Organic substance's content ACETONE ETHYL ACETATE TOLUENE HEXANE THF OCTANE
18 Solubility of 1-Ethyl-3-Methylimidazolium Diethylphosphate Solubility of 1-Ethyl-3-Methylimidazolium Diethylphosphate Solvent concentration in IL Phase IL concentration in Solvent Phase Orga anic substance's content ETHYL ACETATE TOLUENE HEXANE THF OCTANE
19 Solubility of BMPyrr Bis(trifluormethylsulfonyl)imide Solubility of N-Butyl-N-Methylpyrrolidinium Bis(trifluormethylsulfonyl)imide Or rganic substance's content Solvent concentration in IL Phase IL concentration in Solvent Phase 0 TOLUENE HEXANE WATER OCTANE 1-OCTANOL
20 Solubility of 1-Butyl-3-Methylimidazolium dicyanamide Solubility of 1-Butyl-3-Methylimidazolium Dicyanamide Organic substance's content Solvent concentration in IL Phase IL concentration in Solvent Phase 0 ETHYL ACETATE TOLUENE HEXANE OCTANE
21 3 Conclusions COSMOLOGIC 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
22 Conclusions ILs are not generally soluble in Acetone; why? Some PF 6 ILs are well water soluble (!) ILs which are soluble in AcOEt are water insoluble, and vice versa Imidazolium-based ILs are better soluble in AcOEt than Pyrrolidinium or even Pyridinium ones BTA-based ILs are better soluble in Toluene than the corresponding PF 6 and BF 4 ILs PF 6 and BF 4 - based ILs are better soluble in Hexane than the corresponding BTA ILs We still do not understand enough in order to predict solubility.
23 IOLITEC Enabling success in future technologies COSMOLOGIC N-Butyl-N-methylpyrrolidinium dicyanamide
24 Company Facts IOLITEC Foundation: 2003 since Heilbronn, Germany since Tuscaloosa, USA ( Freiburg) ( Denzlingen) IOLITEC HQ Heilbronn Branch: Chemistry / Material Science Capacity: 10 mt (2010) fast Scale-Up 2011: to per year Products: Customers: ~ 300 ionic liquids 10 in bulk-quantity ~ 130 Nanomaterials 2011: New Dyes for DSSCs > worldwide IOLITEC Inc. Tuscaloosa Employees: 20 (8 PhD Chemists)
25 Company Facts IOLITEC since Heilbronn, Germany since Tuscaloosa, USA ( Freiburg) ( Denzlingen) Foundation: 2003 Branch: Chemistry / Material Science Capacity: 10 mt (2010) fast Scale-Up 2011: to per year Heilbronn, Germany Products: Customers: ~ 300 ionic liquids 10 in bulk-quantity ~ 130 Nanomaterials 2011: New Dyes for DSSCs > worldwide Employees: 20 (8 PhD Chemists) Tuscaloosa, Alabama, USA
26 Company Facts IOLITEC since Heilbronn, Germany since Tuscaloosa, USA ( Freiburg) ( Denzlingen) Foundation: 2003 Branch: Chemistry / Material Science Capacity: 10 mt (2010) fast Scale-Up 2011: to per year Heilbronn, Germany Products: Customers: ~ 300 ionic liquids 10 in bulk-quantity ~ 130 Nanomaterials 2011: New Dyes for DSSCs > worldwide Employees: 20 (8 PhD Chemists) Heilbronn, Germany
27 IOLITEC Ionic Liquids Nano--Technology Nano Energy/Cleantech Available: Available: Available: R&D-Chemicals: > 300 products & custom synthesis Nanoparticles: 125 products metals, metal oxides CNTs, carbides Ready-to-use electrolytes for dye sensitized solar cells (DSSCs) nanoparticledispersions & custom synthesis brand: IOLIDispers sensor-electrolytes special-chemicals: 10 products in bulk quantities available brands: IOLILyte IOLITive Applications: Applications: solvents process chemicals functional fluids Surfactants coatings abrasives lubricants additives Market entry 2011/12: materials for heat storage and - transport Brand: IOLITherm Electrolytes for batteries & Supercaps
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