BasionicTM, BasilTM and CellionicTM

Ionic Liquids Solutions for Your Success

Be Part of Innovation

BASF The Chemical Company

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 High-potential Solutions

Top Intermediates Supplier
The Operating Division Intermediates of the BASF Group develops, produces and markets the worlds largest range of intermediates. The most important of the divisions more than 600 products include amines, diols, polyalcohols, acids and specialties. Among other applications, intermediates are used as starting materials for coatings, plastics, pharmaceuticals, textile fibers, detergents and crop protectants. Innovative BASF intermediates help to improve the properties of the final product and the efficiency of production processes. The ISO 9001:2000-certified Operating Division Intermediates has access to plants at production sites in Europe, Asia and the Americas. Ionic liquids have gained overwhelming interest over the past years, because they offer unique sets of properties not achievable with any other material. This opens up opportunities in many different applications. They might be just a replacement for the material currently used as for example reaction media in chemical processes. Or they are an enabling technology that allows totally new solutions as for example in manufacturing cellulose derivatives. Today they are discussed as high-potential solutions in a broad range of application segments: in chemical reactions and separation processes, in processing metals and polymers, especially biopolymers like cellulose, as electrolytes in electronic devices and, last but not least, as functional or engineering fluids in many different applications. BASF offers easy access to a wide range of products (BasionicTM and CellionicTM) with a broad variety of properties. We will obviously help you to implement ionic liquid technologies 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 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 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 www.sigmaaldrich.com).

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 2003/029.329), and BASF has obtained an exclusive license under these patents with the right 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 www.sigmaaldrich.com.)

Basil: BASFs 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.

Ionic Liquids Fascinating New Materials with Unique Sets of Properties

liquid at <100C, 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

Product List (Basionic)

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

EMIM Acetat BMIM Acetat

LIQUID AT RT

EMIM EtOSO3 BMIM MeOSO3

LOW VISCOSITY

EMIM SCN BMIM SCN

FUNCTIONALIZED

COL Acetate COL Salicylate MTEOA MeOSO3

CAS No.

Molar mass

Melting point C

Viscosity at RT mPas

Viscosity at 80 C mPas 47

Density at 80 C g/cm3 1.11 1.21 1.05 1.13 1.02

Electrochemical window Volt

Electric conductivity S/cm

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

2.1/+0.6 2.1/+0.8 1.6/>1 2.7/>1

2600 (25 C) 30 (25 C) 210 (80 C) 2280 (125 C)

46

1.20

2.2/>1

7200 (80 C)

107 76 105 8 164 7 10 22 14 19 6 9

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)

2.1/>1 2.3/+0.9 2.3/+0.8 2.2/+0.8 2.3/+1.8 1.8/+0.8 2.3/+0.7

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: 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

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

Chemical Processing and Fine Chemicals

Ionic Liquids a New and Valuable Tool in the Chemists Toolbox
Theres 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 BASFs BASIL process.

EtOH

R P OEt

R P R CI

CIN H

Acid Scavenging with BASFs BASIL process

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Electrochemistry and Electrolytes

Ionic Liquids New Prospects for More Sustainable Energy Technologies

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

Transparent conductor (anode) Nano porous TiO2 layer Photosensitive dye

Electricity

Ionic Liquid Formulation (incl. I2/I3 ) Conducting substrate (cathode) Ionic liquids in Dye Sensitized Solar Cells (Graetzel-Cells)
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Polymer and Biopolymer Processing

Ionic Liquids 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, USA

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)

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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

Ionic Liquid Electrolyte (AI L n) m+

Electroplating of Aluminium onto Steel

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Steel

Engineering and Functional Fluids

Ionic Liquids 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

Evaporation

Absorption

Sorbent in Absorption Cooling

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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).

Extraction Processes Utilizing Ionic liquids

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BASFs Ionic Liquids 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 proven to be highly beneficial for the parties involved.

Basionic or customized ionic liquids Licenses for our IP and know-how Cooperation projects

Supply contract Licensing agreement Joint development agreement

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How to Get Exactly the Ionic Liquid You Need?

inquiry lab trials pilot plant production

secrecy agreement product selection basic specification feasibility study

kg samples spec parameters basic tox data price calculation

100 kg samples def. specifications REACH registration price quote

supply contract ton-scale production > in spec > on time

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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

= Trademark of BASF Aktiengesellschaft

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CZ 0711-07/07-1000