Ionic Liquids

BasionicTM, BasilTM and CellionicTM

Ionic Liquids Solutions for Your Success

Be Part of Innovation

bai07_124_Ionic_Liquid_RZ_NEU.qxd 13.08.2007 12:13 Uhr Seite 1

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.


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.


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


5 liquid at

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)


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

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


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


10

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


11

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)


12

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.


13

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+


14

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


15

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).


16

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


17

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


18

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


19

Contact Us

EuropeDr. Uwe Vagt

Phone: +49 621 60 - 48616

Mail: [email protected]

NAFTADr. Megan B. Turner

Phone: +1 973 245 - 6541


AsiaHiroki Saitoh

Phone: +81 3 3238 - 2446


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


CZ

071

1-07

/07-

1000


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Ionic Liquids