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BASF is the worlds leading chemical company: The Chemical Company. Its portfolio ranges from chemicals, plastics, performance products, agricultural products and fine chemicals to crude oil and natural gas. As a reliable partner to virtually all industries, BASFs high-value products and intelligent system solutions help its customers to be more successful. BASF develops new technologies and uses them to meet the challenges of the future and open up additional market opportunities. It combines economic success with environmental protection and social responsibility, thus contributing to a better future.
Ionic Liquids and Eco-efficiency Ionic liquids have attracted overwhelming interest over the past years. Besides their technical and economic advantages, ionic liquids are often claimed to be green chemicals, mainly by reference to the fact that they show no vapor pressure. However, it might be misleading to assume that non-volatility alone makes a material green. A more precise approach needs to evaluate the whole process from cradle to grave including a toxicological assessment of the ionic liquid involved. This has been done, for example, for BASFs BASIL process in the synthesis of phosphorous compounds and resulted in the Eco-efficiency Analysis Label in 2005. BASF is prepared to investigate in Eco-efficiency Analysis for ionic liquids products and processes together with customers.
Ionic Liquid
Basionic
Product name
STANDARD
EMIM Cl EMIM CH3SO3 BMIM Cl BMIM CH3SO3 MTBS MMMPZ MeOSO3 EMMIM EtOSO3 MMMIM MeOSO3
ST 80 ST 35 ST 70 ST 78 ST 62 ST 33 ST 67 ST 99 AC 75 AC 39 AC 25 AC 09 AC 28 AC 01 BC 01 BC 02 LQ 01 LQ 02 VS 01 VS 02 FS 85 FS 65 FS 01
1-Ethyl-3-methylimidazolium chloride 1-Ethyl-3-methylimidazolium methanesulfonate 1-Butyl-3-methylimidazolium chloride 1-Butyl-3-methylimidazolium methanesulfonate Methyl-tri-n-butylammonium methylsulfate 1,2,4-Trimethylpyrazolium methylsulfate 1-Ethyl-2,3-di-methylimidazolium ethylsulfate 1,2,3-Trimethyl-imidazolium methylsulfate Methylimidazolium chloride Methylimidazolium hydrogensulfate 1-Ethyl-3-methylimidazolium hydrogensulfate 1-Ethyl-3- methylimidazolium tetrachloroaluminate 1-Butyl-3-methylimidazolium hydrogensulfate 1-Butyl-3-methylimidazolium tetrachloroaluminate 1-Ethyl-3-methylimidazolium acetate 1-Butyl-3-methylimidazolium acetate 1-Ethyl-3- methylimidazolium ethylsulfate 1-Butyl-3-methylimidazolium methylsulfate 1-Ethyl-3-methylimidazolium thiocyanate 1-Butyl-3-methylimidazolium thiocyanate Choline acetate Choline salicylate Tris-(2-hydroxyethyl)-methylammonium methylsulfate
ACIDIC
HMIM Cl HMIM HSO4 EMIM HSO4 EMIM AlCl4 BMIM HSO4 BMIM AlCl4
BASIC
LIQUID AT RT
LOW VISCOSITY
FUNCTIONALIZED
CAS No.
Molar mass
Melting point C
Viscosity at RT mPas
Viscosity at 80 C mPas 47
65039-09-0 145022-45-3 79917-90-1 342789-81-5 13106-24-6 856614-13-6 516474-08-01 65086-12-6 35487-17-3 681281-87-8 412009-61-1 80432-05-9 262297-13-2 80432-09-3 143314-17-4 284049-75-8 342573-75-5 401788-98-5 331717-63-6 344790-87-0 14586-35-7 2016-36-6 29463-06-7
146.62 206.27 174.67 234.32 311.49 222.29 250.32 222.26 118.56 180.18 208.24 279.96 236.29 308.01 170.22 198.27 236.29 250.32 169.25 197.30 163.21 221.48 275.32
80 35 70 7580 62 33 67 113 75 39 923 1650 9 28 10 <20 <20 <20 <20 <20 <20 85 36 <20 686 26 4320 32 93 554 122 214 22 54 109
13 147 18 81
46
1.20
2.2/>1
7200 (80 C)
1.18 1.45 1.33 1.28 1.24 1.20 1.07 1.02 1.20 1.17 1.08 1.04
2.2/>1 2.1/+1.7
11000 (90 C)
8200 (25 C) 2500 (25 C) 1100 (25 C) 80 (25 C) 20 (25 C) 220 (25 C) 40 (25 C)
103 53
1.15 1.38
Ionic liquids are a class of fascinating, new liquid materials with unique combinations of properties. The performance of an ionic liquid in a given application is a strong function of the ions forming the liquid. Several systematic approaches are available towards improving the performance by structural design. Prof. Peter Wasserscheid, University of Erlangen, Germany
Chemical Processing and Fine Chemicals reaction media, for example in catalytic processes reaction media, for example in nucleophilic substitutions auxiliary for acid scavenging (BASIL)
Metal Processing electroplating of aluminum onto steel electroplating of chromium electropolishing of steel and other metal surfaces
Polymer and Biopolymer Processing solvent for regenerating cellulose (e.g. fibers and films) enabling technology for manufacturing cellulose derivatives and polymer blends
Electrochemistry and Electrolytes high-performance electrolyte in lithium ion batteries and supercapacitors solvent and electrolyte in dye-sensitized solar cells
Separation Processes entrainer in extractive distillations, e.g. ethanol/water extraction processes (e.g. aromatics from aliphatics) biorefinery (separation of lignin from cellulose)
Engineering and Functional Fluids non-flammable hydraulic liquids high-performing lubricants and cleaning fluids
As reaction media in chemical processes ionic liquids can be valuable tools to achieve higher yields and/or lower manufacturing costs, for example in catalytic reactions like hydroformylation, hydrosilylation or FRIEDEL-CRAFTS as well as biocatalytic and enzy matic reactions, nucleophilic substitution reactions, acid scavenging with BASFs BASIL process.
EtOH
R P OEt
R P R CI
CIN H
Ionic liquids contain only ions! Best choice for electrochemistry and surrounding scientific fields. Why dont you try to use them? Prof. Hiroyuki Ohno, Tokyo University of Agriculture & Technology, Japan
A relatively low-viscosity, non-flammable liquid showing electric conductivity and wide electrochemical windows: this is a combination of properties not achievable with any other material than ionic liquids. Some examples where ionic liquids offer new opportunities: higher efficiency and safety in lithium ion batteries, higher capacities and safety in supercapacitors, electrolytes in dye-sensitized solar cells.
Light
Electricity
Ionic Liquid Formulation (incl. I2/I3 ) Conducting substrate (cathode) Ionic liquids in Dye Sensitized Solar Cells (Graetzel-Cells)
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The exceptional dissolution properties of ionic liquids for polymers and especially biopolymers such as cellulose, open up totally new opportunities for new products as well as processes, for example: inert solvent for cellulose allowing any kind of derivatization, higher utilization of the most abundant raw material source: cellulose, a broad range of opportunities in processing polymers and biopolymers.
Metal Processing
Ionic Liquids Unprecedented Prospects for Metal Deposition
Thin layers of silicon, silicon nanoparticles, deposition of aluminum on steel, electrolysis of tantalum compounds just a few examples showing that ionic liquids in electrochemistry are both, an opportunity and a challenge! The challenge will be to convert the opportunities into commercial products and processes. Prof. Frank Endres, University of Claustal, Germany
The high electrochemical stability of ionic liquids allows electrochemical deposition of less noble metals like aluminium or titanium, which is not possible with conventional aqueous electrolytes. Examples: electroplating of aluminum onto steel electroplating of chromium electropolishing of steel and other metal surfaces
Aluminium
Steel
Based on their ionic structure, ionic liquids show remarkable physical properties which can be exploited in many high-tech engineering and functional fluids such as non-flammable hydraulic liquids, high-performing lubricants, and cleaning fluids.
Condensation
Desorption
Evaporation
Absorption
Separation Processes
Ionic Liquids With New Opportunities to Higher profitability
Due to their unique solvent properties ionic liquids can enable new separation concepts or new intensified processes and products. Their performance is the key driver to profitability. Prof. Andre de Haan, University of Eindhoven, The Netherlands
The unique dissolving and miscibility properties of ionic liquids offer great potential in a broad range of separation processes, for example: as an entrainer in extractive distillations, e.g. ethanol/water, in extraction processes (e.g. aromatics from aliphatics), in biorefinery (separation of lignin and cellulose).
Basionic or customized ionic liquids Licenses for our IP and know-how Cooperation projects
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Worldwide Support
We offer you a full range of services around the globe: Our team of experts and consultants will advise you throughout the implementation. Starting from first lab trials we support you on your way to realizing new processes and products on a commercial scale. On request, we will design the recycling of ionic liquids after use and will assist you in all aspects of chemical legislation (e.g. REACH), backed by our internationally renowned expertise in toxicology and ecotoxicology.
Karin Sperling
Uwe Vagt
Matthias Maase
Eric Uerdingen
Jrgen Pongratz
Megan B. Turner
Aurelie Alemany
Klaus Breuer
James Li
Pulakesh Mukherjee
Hiroki Saitoh
SangHoon Shin
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Contact Us
Europe
Dr. Uwe Vagt Phone: +49 621 60 - 48616 Mail: uwe.vagt@basf.com
NAFTA
Dr. Megan B. Turner Phone: +1 973 245 - 6541 Mail: megan.turner@basf.com For the supply of BASIONIC Ionic liquids in small quantities please contact:
Asia
Hiroki Saitoh Phone: +81 3 3238 - 2446 Mail: hiroki.saitoh@basf.com
SIGMA-ALDRICH
www.basf.de/intermediates
www.sigmaaldrich.com
The data contained in this publication is based on our current knowledge and experience. In view of the many factors that may affect processing and application of our product, the data does not relieve processors from carrying out their own investigations and tests; neither does the data imply any guarantee of certain properties, nor the suitability of the product for a specific purpose. Any descriptions, drawings, photographs, data, proportions, weights etc. given herein may change without prior information and do not constitute the agreed contractual quality of the product. It is the responsibility of the recipient of our products to ensure that any proprietary rights and existing laws and legislation are observed. The safety data given in this publication is for information purposes only and does not constitute a legally binding Material Safety Data Sheet (MSDS). The relevant MSDS can be obtained upon request from your supplier or you may contact BASF directly at product-safety.intermediates@basf.com. Edition 2007
TM
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CZ 0711-07/07-1000