Basionics Brochure

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Intermediates

Basionics
Ionic Liquids solutions
for your success

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BASF
The Chemical Company

BASF is the worlds leading chemical company: The Chemical Company.


Its portfolio ranges from chemicals, plastics, performance products and
agricultural products to oil and gas. As a reliable partner BASF creates
chemistry to help its customers in virtually all industries to be more
successful. With its high-value products and intelligent solutions, BASF
plays an important role in finding answers to global challenges such as
climate protection, energy efficiency, nutrition and mobility.

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
operates plants in Europe, Asia and the Americas.

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Ionic 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 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. They are being considered
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
(Basionics) 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 (Basil) as well as joint developments
leading exactly to the products or processes that meet
your requirements.

Ionic Liquids and eco-efficiency


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 ionic
liquid products and processes together
with customers by means of an ecoefficiency analysis.

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Ionic Liquids from BASF

Basionics:
Broad portfolio meeting your
requirements
BASF has developed the Basionics 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.
Small quantities of our Basionics for testing and screening
are provided by our partner Sigma-Aldrich (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 will help you to harness your potential and
raise yields, improve efficiency and simplify processes.

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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

The mechanical properties


of components made of
glassfiber-reinforced epoxy
resins are determined by
means of state-of-the-art
testing equipment.

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Product list Ionic Liquids


product name

short name

CAS-No.

PRD No.

designation

1-Ethyl-3-methyl imidazolium chloride

EMIM Cl

65039-09-0

30271832

Basionics ST 80

1-Butyl-3-methyl imidazolium chloride

BMIM Cl

79917-90-1

30271827

Basionics ST 70

1-Ethyl-3-methyl imidazolium methanesulfonate

EMIM MeSO3

145022-45-3

30271835

Basionics ST 35

1-Ethyl-3-methyl imidazolium ethylsulfate

EMIM EtOSO3

342573-75-5

30254248

Basionics LQ 01

1-Ethyl-3-methyl imidazolium diethylphosphate

EMIM DEP

848641-69-0

30470177

Basionics LQ 11

1-Ethyl-3-methyl imidazolium dicyanamide

EMIM DCA

370865-89-7

30470176

Basionics VS 03

1-Ethyl-3-methyl imidazolium acetate

EMIM OAc

143314-17-4

30271819

Basionics BC 01

1-Ethyl-3-methyl imidazolium thiocyanate

EMIM SCN

331717-63-6

30271823

Basionics VS 01

1-Ethyl-3-methyl imidazolium tetrafluoroborate

EMIM BF4

143314-16-3

30454010

Basionics EE 03

1-Ethyl-3-methyl imidazolium triflourmethanesulfonate

EMIM Otf

145022-44-2

30470173

Basionics VS 11

174899-82-2

30455435

Basionics HP 01

1-Ethyl-3-methyl imidazolium bis(trifluormethanesulfonyl)imide EMIM TFSI


Tris(2-hydroxyethyl)methylammonium methylsulfate

MTEOA MeOSO3 29463-06-7

30265309

Basionics FS 01

EMIM Cl x Aluminium chloride (1 : 1.5 mol)

EMIM Cl x AlCl3

65039-09-0

30487259

Basionics AL 01

1-Ethyl-3-methyl imidazolium methylcarbonate (in methanol)

EMIM MC

251102-25-7

30467453

intermediate

1-Butyl-3-methyl imidazolium methylcarbonate (in methanol) BMIM MC

916850-37-8

30466514

intermediate

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labeling

hazard statements/
toxicity

molar mass

mp (C)

H 319, H 302

146.62

88

47

1.11

H 319, H 315, H 301,


H 411

174.67

70

147

1.05

no label

206.27

35

13

1.21

no label

236.29

<-20

122

14

1.24

no label

264.26

10

109

13

1.21

177.21

-11

20

1.07

170.22

<-20

93

1.07

H 312, H 332, H 412

169.25

<-20

22

1.08

H 302, H 411

197.97

<-20

37

1.23

260.24

-9

52

1.30

391.3

-16

32

275.23

-20

1148

1.3447 @ 25

-16

16.4

1.3501 @ 25

H 318, H 302, H 317


no label

no label

H 314, H 311, H 301,


H 411, H 373
no label

H 314, H 302

visc at RT
(mPas)

visc at 80C
(mPas)

density at 80C
(g/cm)

1.52

H 225, H 319, H 315,


H 311, H 330, H 301,
H 370, H 411

186.21

0.87

H 225, H 319, H 315,


H 311, H 330, H 301,
H 370, H 411

214.26

0.86

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Ionic Liquids
offering outstanding advantages

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
dissolution and separation of lignocellulosic biomass

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

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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)
purification of gases

Engineering fluids
non-flammable hydraulic liquids
high-performing lubricants
liquid piston and gas compression

Functional fluids
antistatic additives
catalysts (e.g. polyurethanes)
reactive building blocks
other polymer additives

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Chemical processing and


fine chemicals

Ionic Liquids a new and valuable


tool in the chemists toolbox
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
enzymatic reactions,
nucleophilic substitution reactions,
acid scavenging with BASFs BASIL process.

EtOH

OEt

R
P

CI
CI-

H
N

Acid scavenging with BASFs BASIL process

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

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Electrochemical applications

Ionic Liquids new prospects


for more sustainable energy
technologies
Electrochemical devices are getting more and more attractive
with the increasing interest in generating electricity from
renewable resources. Ionic Liquids can offer valuable
contributions:
customized products for electrolytes in lithium ion
batteries
electrolytes allowing higher power densities in super
capacitors
solvent free electrolyte for 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 sells (Graetzel-Cells)

Low viscous, non volatile liquids showing electric


conductivity this is not achievable with any other
material than Ionic Liquids, qualifying them as new
materials for electrolytes.
Heiko Kupfer, BASF SE

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Polymer and biopolymer


processing

Ionic Liquids enabling technology


to utilize cellulose
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)

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

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Metal processing

Ionic Liquids unprecedented


prospects for metal deposition
The high electrochemical stability of Ionic Liquids allows
electrochemical deposition of less noble metals like
aluminum or titanium, which is not possible with
conventional aqueous electrolytes. Examples:
electroplating of aluminum onto steel
electroplating of chromium

Ionic Liquid
Electrolyte
(AI Ln) m+

Steel

Aluminum

electropolishing of steel and other metal surfaces

Electroplating of aluminum onto steel

Ionic Liquids can be specifically modified by additives to


high performing electrolytes in electroplating processes
for the galvano industry.
Dr. Jochen Mezger, BASF SE

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Engineering fluids

Ionic Liquids designable materials


for high-performing fluids
Based on their ionic structure, Ionic Liquids show
remarkable physical properties that can be exploited
in many high-tech engineering and functional fluids
such as
non-flammable hydraulic liquids,
high-performing lubricants,
liquid piston in gas compression.

Condensation

Desorption

IL/H2O instead
of LiBr/H2O

Evaporation

Absorption

Sorbent in absorption cooling

One of the largest resources of energy is simply to


save energy. And it is exactly here where Ionic Liquids
can make their contributions.
Dr. Klemens Massonne, BASF SE

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Separation processes

Ionic Liquids with new opportunities


to higher profitability
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),
purification of gases.

Extraction processes utilizing Ionic Liquids

Ionic Liquids are characterized by exceptional dissolution properties. This opens up opportunities in utilizing
them as auxiliaries in e.g. extractive distillations leading
to processes with higher profitability.
Dr. Uwe Vagt, BASF SE

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Functional liquids
for polymers

Basionics new prospects for


polymer chemists
The specific interaction of Basionics with different kinds
of polymers makes them attractive materials as high
performance polymer additives; esp. as these interactions
are easily tunable by the design of the Ionic Liquids
antistatic additive (e.g. thermoset, engineering
plastics, coatings)
functionalised building blocks for resins manufacture
latent hardeners (e.g. polyurethane, epoxy)
other polymers additives

Basionics are also used as high performance antistatic additives in different


polymer applications.

To optimize the properties and the processibility


of polymers becomes more and more important
with increasing customer requirements for high
performing polymers.
Dr. Laszlo Szarvas, BASF SE

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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 Basionics 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.

How to get exactly the Ionic Liquid you need?


inquiry

lab trials

pilot plant

production

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

*in co-operation with Sigma-Aldrich

Basionics or customized Ionic Liquids

Supply contract

Licenses for our IP and know-how

Licensing agreement

Cooperation projects

Joint development agreement

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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.
Karin Sperling

Koichiro Aoyagi

Andreas Eichfelder

Daniel Klein

Heiko Kupfer

Clement Lam

Megan OMeara

Jochen Mezger

Christian Seitz

SangHoon Shin

Lazslo Szarvas

Uwe Vagt

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.

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Contact us

Europe
Dr. Uwe Vagt
Phone: +49 621 60 - 48616
[email protected]

NAFTA
Dr. Megan OMeara
Phone: +1 973 245 - 6541
[email protected]

For the supply of BASIONICS ionic


liquids in small quantities please
contact:

SIGMA-ALDRICH

Asia
Koichiro Aoyagi
Phone: +81 3 3796 - 4945
[email protected]

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 [email protected]. 2011 edition

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www.sigmaaldrich.com

www.basionics.com
www.basf.de/intermediates

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CZ1104-04/11-2000
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