1-ETHYL-3-METHYLIMIDAZOLIUM METHANESULFONATE (cas ) MSDS

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1 Click for suppliers of this product 1-ETHYL-3-METHYLIMIDAZOLIUM METHANESULFONATE (cas ) MSDS BasionicTM, BasilTM and CellionicTM Solutions for Your Success??Be Part of Innovation?? BASF The Chemical Company BASF is the world??s 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, BASF??s 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. 2 High-potential Solutions Top Intermediates Supplier The Operating Division Intermediates of Ionic liquids have gained overwhelming interest over the past the BASF Group develops, produces years, because they offer unique sets of properties not and markets the world??s largest range achievable with any other material. This opens up opportunities of intermediates. The most important of in many different applications. They might be just a replacethe division??s more than 600 products ment for the material currently used?? as for example reaction

2 include amines, diols, polyalcohols, media in chemical processes. Or they are an??enabling techacids and specialties. Among other nology?? that allows totally new solutions?? as for example in applications, intermediates are used as manufacturing cellulose derivatives. Today they are discussed starting materials for coatings, plastics, as high-potential solutions in a broad range of application pharmaceuticals, textile fibers, deter- segments: in chemical reactions and separation processes, in gents and crop protectants. Innovative processing metals and polymers, especially biopolymers like BASF intermediates help to improve the cellulose, as electrolytes in electronic devices and, last but properties of the final product and the not least, as functional or engineering fluids in many differefficiency of production processes. ent applications. The ISO 9001:2000-certified Operating BASF offers easy access to a wide range of products Division Intermediates has access to (BasionicTM and CellionicTM) with a broad variety of properties. plants at production sites in Europe, We will obviously help you to implement ionic liquid tech- Asia and the Americas. nologies to your processes and products with any support you need. This also includes licensing of BASF technologies utilizing ionic liquids (BasilTM) as well as joint developments leading exactly to the products or processes that meet your requirements. Ionic Liquids and Eco-efficiency Ionic liquids have attracted over- the whole process from??cradle to whelming interest over the past years. grave???? including a toxicological Besides their technical and economic assessment of the ionic liquid involved. advantages, ionic liquids are often This has been done, for example, for claimed to be??green?? chemicals, BASF??s BASIL process in the synthesis mainly by reference to the fact that of phosphorous compounds?? and they show no vapor pressure. resulted in the??eco-efficiency Analysis However, it might be misleading to Label?? in BASF is prepared to assume that non-volatility alone investigate in Eco-efficiency Analysis makes a material??green??. A more for ionic liquids products and processes precise approach needs to evaluate together with customers. 3 Ionic Liquids from BASF Basionic: Broad Portfolio?? Meeting Your Requirements BASF has developed the Basionic portfolio of ionic liquids offering a broad variety of properties. The focus in this product line is on imidazolium salts. All products are available from lab to industrial scale (for a detailed list see pages 6 and 7 in this brochure). Our existing production capacities ensure flexibility, reliable supply and global availability. On your request we are also pleased to check our capabilities for those products not included in our portfolio so far, as well as special requirements on specifications. Smaller quantities of our Basionics for testing and screening are provided by our partner Sigma-Aldrich (please refer to Cellionic: Ready-to-use: Solutions of Cellulose One of the most remarkable properties of ionic liquids is their ability to dissolve cellulose. This opens up a broad range of opportunities which so far could not be investigated, as solutions of cellulose in chemically inert solvents simply did not exist. The dissolution and processing of cellulose in ionic liquids was invented by Prof. Robin Rogers et al. from the University of Alabama (WO 2003/ ), and BASF has obtained an exclusive license under these patents with the right

3 to sublicense these. In order to allow you an easy start for first screening experiments in this field, we offer solutions of cellulose with different degrees of polymerization in EMIM acetate as a 5% solution under the trade name Cellionic. (Again, for small quantities please refer to Basil: BASF??s Ionic-liquid-based Processes We invite you to benefit from our pioneering work utilizing ionic liquids in chemical processing. Several processes applying ionic liquids in synthesis and separation steps have been elaborated within BASF, and we are pleased to license them to you (Basil processes). However, if you need a very specific solution, why not enter into an exclusive cooperation agreement with us, and we will jointly develop new processes that exactly meet your needs. With our expertise in using ionic liquids we open up potentials resulting in higher yields, improved efficiencies and simplified processes. 4 Fascinating New Materials with Unique Sets of Properties?? liquid at <100??C, often liquid at room temperature?? broad liquid range?? virtually no vapor pressure?? non-flammable?? excellent thermal, mechanical and electrochemical stability?? electrical conductivity?? exceptional dissolution properties 5 Product List (Basionic) Ionic Liquid Basionic Product name STANDARD EMIM Cl ST 80 1-Ethyl-3-methylimidazolium chloride EMIM CH3SO3 ST 35 1-Ethyl-3-methylimidazolium methanesulfonate BMIM Cl ST 70 1-Butyl-3-methylimidazolium chloride BMIM CH3SO3 ST 78 1-Butyl-3-methylimidazolium methanesulfonate MTBS ST 62 Methyl-tri-n-butylammonium methylsulfate MMMPZ MeOSO3 ST 33 1,2,4-Trimethylpyrazolium methylsulfate EMMIM EtOSO3 ST 67 1-Ethyl-2,3-di-methylimidazolium ethylsulfate

4 MMMIM MeOSO3 ST 99 1,2,3-Trimethyl-imidazolium methylsulfate ACIDIC HMIM Cl AC 75 Methylimidazolium chloride HMIM HSO4 AC 39 Methylimidazolium hydrogensulfate EMIM HSO4 AC 25 1-Ethyl-3-methylimidazolium hydrogensulfate EMIM AlCl4 AC 09 1-Ethyl-3- methylimidazolium tetrachloroaluminate BMIM HSO4 AC 28 1-Butyl-3-methylimidazolium hydrogensulfate BMIM AlCl4 AC 01 1-Butyl-3-methylimidazolium tetrachloroaluminate BASIC EMIM Acetat BC 01 1-Ethyl-3-methylimidazolium acetate BMIM Acetat BC 02 1-Butyl-3-methylimidazolium acetate LIQUID AT RT EMIM EtOSO3 LQ 01 1-Ethyl-3- methylimidazolium ethylsulfate BMIM MeOSO3 LQ 02 1-Butyl-3-methylimidazolium methylsulfate LOW VISCOSITY EMIM SCN VS 01 1-Ethyl-3-methylimidazolium thiocyanate BMIM SCN VS 02 1-Butyl-3-methylimidazolium thiocyanate FUNCTIONALIZED COL Acetate FS 85 Choline acetate COL Salicylate FS 65 Choline salicylate MTEOA MeOSO3 FS 01 Tris-(2-hydroxyethyl)-methylammonium methylsulfate 6 CAS No. Molar Melting Viscosity Viscosity Density Electrochemical Electric mass point at RT at 80??C at 80??C window conductivity g/cm3??c mpas mpas Volt??S/cm ??2.1/ (25??C) ??2.1/ (25??C) ?? ??1.6/>1 210 (80??C) ??2.7/> (125??C) ??2.2/> (80??C) ??2.2/> (90??C) ??2.1/

5 ?? ??2.1/> (25??C) Ionic Liquids: Offering Outstanding Advantages??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

6 8 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 9 Chemical Processing and Fine Chemicals a New and Valuable Tool in the Chemist??s Toolbox??There??s no reason why someone should use ionic liquids if he is happy with what he is already doing. But if he has problems, ionic liquids are valid possible alternatives to try?? and there is a great chance that they may work.?? Prof. Ken Seddon, University of Belfast, Northern Ireland, UK 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 BASF??s BASIL process.

7 EtOH P OEt P CI CI- N N H N N Acid Scavenging with BASF??s BASIL process 10 Electrochemistry and Electrolytes New Prospects for More Sustainable Energy Technologies??Ionic liquids contain only ions! Best choice for electrochemistry and surrounding scientific fields. Why don??t 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 Transparent conductor (anode) Nano porous TiO2 layer Electricity Photosensitive dye Ionic Liquid Formulation (incl. I2/I3?? )

8 Conducting substrate (cathode) Ionic liquids in Dye Sensitized Solar Cells (?Graetzel-Cells??) 11 Polymer and Biopolymer Processing Enabling Technology to Utilize Cellulose??I believe that the ability of certain ionic liquids to directly dissolve and efficiently separate the key biomass components, cellulose, hemicelluloses, and lignin, could be the technological key to enabling a sustainable hydrocarbon economy!?? Prof. Robin Rogers, University of Alabama, Tuscaloosa, 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. Regenerated Cellulose (e.g.??viscose Fibres??) 12 Metal Processing 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:

9 ?? electroplating of aluminum onto steel?? electroplating of chromium?? electropolishing of steel and other metal surfaces Aluminium Steel Ionic Liquid Electrolyte (AI L n) m+ Electroplating of Aluminium onto Steel 13 Engineering and Functional Fluids Designable Materials for High-performing Fluids??Many unexpected phenomena occur in ionic liquids, which can make everyone a challenger and pioneer of new fields. This is because there are no other liquids that consist entirely of ions. Make new materials and create new devices by using ionic liquids and you can be a??prince of Serendip??.?? Prof. Masayoshi Watanabe, Yokohama National University, Japan 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 IL/H2O instead of LiBr/H2O

10 Evaporation Absorption Sorbent in Absorption Cooling 14 Separation Processes 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). Extraction Processes Utilizing Ionic liquids 15 BASF??s Customized Solutions for You Close Cooperation?? Our Business Models We are your full-service partner when you are evaluating your possibilities to use ionic liquids. Backed by our technological expertise, we provide support for engineering processes, whether they are close to implementation or just developed on a laboratory scale, or we investigate together with you whether your ideas can be realized. Naturally, we supply you with one of our Basionic products or customized ionic liquids designed to fit your needs. We offer licenses for our intellectual property covering ionic liquids and especially for our Basil processes, and we actively encourage and support joint research agreements, which have previously

11 proven to be highly beneficial for the parties involved.?? Basionic or customized ionic liquids Supply contract?? Licenses for our IP and know-how Licensing agreement?? Cooperation projects Joint development agreement 16 How to Get Exactly the Ionic Liquid You Need? inquiry lab trials pilot plant production secrecy agreement kg samples 100 kg samples supply contract product selection spec parameters def. specifications ton-scale production basic specification basic tox data REACH registration > in spec feasibility study price calculation price quote > on time 17 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 J??rgen Pongratz Megan B. Turner Aurelie Alemany Klaus Breuer James Li Pulakesh Mukherjee Hiroki Saitoh SangHoon Shin 18 Contact Us Europe Dr. Uwe Vagt Phone:

12 Mail: NAFTA Dr. Megan B. Turner Phone: For the supply of BASIONIC Ionic Mail: liquids in small quantities please contact: Asia SIGMA- Hiroki Saitoh Phone: Mail: hiroki.saitoh@basf.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 = Trademark of BASF Aktiengesellschaft TM 19 CZ /

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