Download - Ionic Liquids
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BasionicTM, BasilTM and CellionicTM
Ionic Liquids Solutions for Your Success
Be Part of Innovation
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2BASFThe 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.
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3Ionic Liquids High-potential Solutions
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 replace-
ment for the material currently used as for example reaction
media in chemical processes. Or they are an enabling tech-
nology 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 differ-
ent 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 tech-
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.
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, deter-
gents 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.
Top Intermediates Supplier
Ionic Liquids and Eco-efficiency
Ionic liquids have attracted over-
whelming 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.
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4Ionic Liquids from BASF
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 capa-
bilities 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).
Basionic:Broad Portfolio Meeting Your Requirements
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 experi-
ments in this field, we offer solutions of cellulose with different degrees of poly-
merization in EMIM acetate as a 5% solution under the trade name Cellionic.
(Again, for small quantities please refer to www.sigmaaldrich.com.)
Cellionic:Ready-to-use: Solutions of Cellulose
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.
Basil:BASFs Ionic-liquid-based Processes
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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
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
Product List (Basionic)
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CAS No. Molar Melting Viscosity Viscosity Density Electrochemical Electric
mass point at RT at 80 C at 80 C window conductivity
C mPas mPas g/cm3 Volt S/cm
65039-09-0 146.62 80 47 1.11
145022-45-3 206.27 35 109 13 1.21 2.1/+0.6 2600 (25 C)
79917-90-1 174.67 70 147 1.05 2.1/+0.8 30 (25 C)
342789-81-5 234.32 7580 18 1.13 1.6/>1 210 (80 C)
13106-24-6 311.49 62 81 1.02 2.7/>1 2280 (125 C)
856614-13-6 222.29 33
516474-08-01 250.32 67 46 1.20 2.2/>1 7200 (80 C)
65086-12-6 222.26 113
35487-17-3 118.56 75 107 1.18 2.2/>1 11000 (90 C)
681281-87-8 180.18 39 923 76 1.45 2.1/+1.7
412009-61-1 208.24 1650 105 1.33
80432-05-9 279.96 9 26 8 1.28
262297-13-2 236.29 28 4320 164 1.24
80432-09-3 308.01 10 32 7 1.20 2.1/>1 8200 (25 C)
143314-17-4 170.22
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8Ionic Liquids: OfferingOutstanding 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
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9Electrochemistry 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
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Chemical Processing and Fine Chemicals
Ionic Liquids a New and Valuable Tool in the Chemists Toolbox
Acid Scavenging with BASFs BASIL process
Theres no reason why someone should use ionic liq-
uids if he is happy with what he is already doing. But if
he has problems, ionic liquids are valid possible alterna-
tives 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, hydrosilylationor FRIEDEL-CRAFTS as well as biocatalytic and enzy
matic reactions,
nucleophilic substitution reactions,
acid scavenging with BASFs BASIL process.
H
CI- NN
NN
P OEt
R
R
EtOH
P CI
R
R
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Ionic liquids in Dye Sensitized Solar Cells (Graetzel-Cells)
Ionic liquids contain only ions! Best choice for electro-
chemistry 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.
Electrochemistry and Electrolytes
Ionic Liquids New Prospects for MoreSustainable Energy Technologies
Transparent conductor (anode)
Light
Electricity
Nano porous TiO2 layer
Photosensitive dye
Ionic Liquid Formulation (incl. I2/I3 )
Conducting substrate (cathode)
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Polymer and Biopolymer Processing
Ionic Liquids Enabling Technology to Utilize Cellulose
Regenerated Cellulose (e.g. Viscose Fibres)
I believe that the ability of certain ionic liquids to direct-
ly 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.
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Ste
el
Metal Processing
Ionic Liquids Unprecedented Prospects for Metal Deposition
Thin layers of silicon, silicon nanoparticles, deposition
of aluminum on steel, electrolysis of tantalum com-
pounds just a few examples showing that ionic liquids
in electrochemistry are both, an opportunity and a chal-
lenge! The challenge will be to convert the opportunities
into commercial products and processes.
Prof. Frank Endres, University of Claustal, Germany
Electroplating of Aluminium onto Steel
The high electrochemical stability of ionic liquids allows
electrochemical deposition of less noble metals like alumini-
um 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
Ionic LiquidElectrolyteA
lum
iniu
m
(AI Ln) m+
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Engineering and Functional Fluids
Ionic Liquids Designable Materials for High-performing Fluids
Sorbent in Absorption Cooling
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 remark-
able 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.
IL/H2O insteadof LiBr/H2O
Absorption
DesorptionCondensation
Evaporation
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Separation Processes
Ionic Liquids With New Opportunities to Higher profitability
Extraction Processes Utilizing Ionic liquids
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).
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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 tech-
nological 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 Supply contract
Licenses for our IP and know-how Licensing agreement
Cooperation projects 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.
Uwe Vagt
Klaus Breuer
Matthias Maase Eric Uerdingen Jrgen Pongratz Megan B. Turner
James LiAurelie Alemany Pulakesh Mukherjee Hiroki Saitoh SangHoon Shin
Karin Sperling
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Contact Us
EuropeDr. Uwe Vagt
Phone: +49 621 60 - 48616
Mail: [email protected]
NAFTADr. Megan B. Turner
Phone: +1 973 245 - 6541
Mail: [email protected]
AsiaHiroki Saitoh
Phone: +81 3 3238 - 2446
Mail: [email protected]
www.basf.de/intermediates
TM = Trademark of BASF Aktiengesellschaft
The data contained in this publication is based on our current knowledge andexperience. In view of the many factors that may affect processing and applicationof our product, the data does not relieve processors from carrying out their owninvestigations and tests; neither does the data imply any guarantee of certain prop-erties, nor the suitability of the product for a specific purpose. Any descriptions,drawings, photographs, data, proportions, weights etc. given herein may changewithout prior information and do not constitute the agreed contractual quality ofthe product. It is the responsibility of the recipient of our products to ensure thatany proprietary rights and existing laws and legislation are observed. The safetydata given in this publication is for information purposes only and does not consti-tute a legally binding Material Safety Data Sheet (MSDS). The relevant MSDS canbe obtained upon request from your supplier or you may contact BASF directly [email protected]. Edition 2007
For the supply of BASIONIC Ionic
liquids in small quantities please
contact:
SIGMA-ALDRICH
www.sigmaaldrich.com
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CZ
071
1-07
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