Professional Documents
Culture Documents
Welcome To CABB
Welcome To CABB
4 GENERAL OVERVIEW
10 CONTINUOUS PROCESSES
8 OUR VERBUND
AND RECYCLING
SYSTEMS
12 CORE CHEMISTRY
18 MULTI-STEP
SYNTHESES
20 PRODUCT OVERVIEW
3
CONTENTS
GENERAL OVERVIEW 4
CABB AT A GLANCE 5
OUR VERBUND AND RECYCLING SYSTEMS 8
SUSTAINABILITY 9
CONTINUOUS PROCESSES 10
CORE CHEMISTRY 12
Chlorination, Chloromethylation 12
Bromination, Sulfonation 13
Thioalkylation, Methylation 14
Lithiation, Grignard reactions 15
Cross-coupling reactions, Wolff-Kishner reduction 16
Oxidation, Reduction/Hydrogenation 17
CAPABILITIES 18
Multi-step syntheses 18
Equipment for custom manufacturing 19
PRODUCT OVERVIEW 20
Carboxylic Acids and Salts 20
Carboxylic Acid Amides, Anhydrides and Esters 21
Carboxylic Acid Chlorides 22
Chloralkyl Amines / Chloromethyl Esters 24
Alkyl and Aryl Chlorides / Chloroalkyl Ethers 25
Sulfur Trioxide Amine Complexes / Sulfonyl Chlorides / Sulfonic Acid Derivatives,
Sulfites, Sulfones / Terpenes 26
Reagents / Base Chemicals / High-Purity Solvents / Crosslinkers 27
4 CABB | SOLUTIONS AND CAPABILITIES
Investments in €m
523m 80
70 75
past 5 years accumulated €272m
300
250
turnover 60
60
200
50
51 53
150
1,140
40 44
40
30
100
20
employees 10
50
(worldwide) 0 0
2014 2015 2016 2017 2018 2019
5
CUSTOM MANUFACTURING
BY CABB
With around 800 employees and three world-class Our core technologies, sophisticated infrastructure
assets in Finland, Switzerland and the USA, our Custom and the wide range of tools at our disposal enable
Manufacturing Business Unit is a strategic partner to all us to individually develop the ideal solution for each
major players in the agrochemical industry, as well as customer’s specific challenge. This includes the
leading pharmaceutical companies and performance following models of cooperation:
chemical manufacturers.
• Partnership contract
including IP confidentiality
• Development of chemical process
ACETYLS BY CABB
• Custom manufacturing of intermediates and agro- • Leader in chlorination, sulfonation and other
chemical active ingredients technologies for fine chemical production
• Manufacture of reagents, building blocks and • Infrastructure for and expertise in alkylation,
intermediates based on chlorination and sulfonation bromination, lithiation and oxidation on commercial
• Production of monochloroacetic acid and its scale
derivatives • Backward integration into key reagents and
intermediates
PROJECT MANAGEMENT • Pipeline supply of hazardous and corrosive reagents
and intermediates to multipurpose assets
• Customer-intimate approach • Expertise in designing robust and safe processes for
• Reliable long-term partnerships grounded in trust hazardous chemicals
• Strong protection of customers’ intellectual property • Process technology and expertise in turning batch
processes into continuous processes
QUALITY • Equipment and infrastructure for challenging multi-
step syntheses
• Manufacturing according to ISO 9001 and 14001 • Infrastructure for waste management (sewage plant,
• Continuous improvement of quality and processes incineration plant)
• State-of-the-art quality control laboratory and • Process optimization throughout the whole lifecycle
equipment of a product
GLOBAL PRESENCE
Kokkola, Finland
5
9
Knapsack, Germany Sulzbach, Germany
Pratteln, Switzerland Gersthofen, Germany
Jayhawk, USA
Charlotte, USA Jining, China
Shanghai, China
Demonstration of the
Verbund System
CABB operates integrated production and recycling These are then used for the production of further
systems at its sites in Knapsack and Gersthofen downstream intermediates and non-GMP active
(Germany), Kokkola (Finland) and Pratteln (Switzerland). ingredients. The HCl and SO2 generated as off-gases
are separated, purified and recycled or re-used.
At the Pratteln site, a vertically integrated Verbund
and Recycling System enables highly efficient and Our Verbund and Recycling System is based on
sustainable chlorination and sulfonation reactions. a sophisticated infrastructure for the handling of
Chlorine and sulfur trioxide are produced as primary hazardous reagents and intermediates. where a
raw materials, from which a variety of chlorination and hermetically sealed pipeline system links the reagent
sulfonation reagents are subsequently manufactured. storage tanks with the multipurpose production plants.
9
SUSTAINABILITY
Chlorination and sulfonation reactions generate HCl This can be measured in terms of the Process Mass
and/or SO2 as off-gases. In conventional plants, these Intensity (PMI) and the Environmental factor (E-factor).
gases are removed by reaction with caustic soda in a For instance, off-gas scrubbing of a short-chain
scrubber system, generating large amounts of saline carboxylic acid by chlorination with thionyl chloride
waste water. But in CABB’s recycling system, these requires 3.7 kg of caustic soda per kg of product,
off-gases are separated and purified. The HCl is then generating 4.7 kg of saline waste water per kg of
converted into hydrochloric acid for merchant markets. product. At CABB, this waste formation is completely
The SO2 is fed back into the sulfur oxidizing process prevented. (The typical E-factor value for fine chemicals
to generate sulfur-based reagents again. As a result, is between 5 and 50.)
CABB is able to perform chlorination and sulfonation
reactions without generating large amounts of waste.
Sales product
SO2 SO3
>
total mass of waste
recycling E-factor=
total amount of product
Reagents
Starting
materials
CONTINUOUS PROCESSES
Continuous processes are known to
Continuous
support sustainability because they thionyl chloride R–OH
require less material, less energy
raw material in
production
and fewer solvents compared to
batch processes. In addition, reaction SO3
conditions are more constant,
leading to higher product quality and Continuous
safety. SO2 reaction
Continuous waste
CABB has a repertoire of continuous water oxidation
standard unit operations that can
be combined into efficient systems
without bottlenecks, backed up by
Continuous
product out
R–Cl
11
12 CABB | SOLUTIONS AND CAPABILITIES
CORE CHEMISTRY
CHLORINATION CHLOROMETHYLATION
CABB has various chlorination reagents readily Chloromethylation of alcohols and carboxylic acids
available: chlorine, thionyl chloride, sulfuryl chloride yields the corresponding chloromethyl ethers and
and hydrogen chloride gas. These reagents are esters. CABB’s proprietary technology guarantees a
produced in our Verbund System and are transported smooth reaction with high yields and very low content
in hermetically sealed pipelines directly from storage of the carcinogenic byproduct bis(chloromethyl)ether.
tanks to multipurpose and dedicated reactors. The HCl
and SO2 formed as off-gases are fully recycled in our Thanks to CABB’s Verbund System, reagents are
Verbund System in a sustainable and environmentally available from pipeline and off-gases are fully recycled.
friendly way, preventing the formation of large volumes
of scrubber waste water.
Benefits Benefits
• Backward integration into key reagents • Backward integration into key reagents
• Sustainable production processes • Sustainable production processes
• Efficient batch and continuous chlorination processes • Environmentally friendly recycling of off-gases
• Environmentally friendly recycling of off-gases • Very low content of bis(chloromethyl)ether
13
BROMINATION SULFONATION
CABB possesses the infrastructure and expertise to As part of its Verbund System, CABB produces
carry out bromination on a large industrial scale. We sulfonation reagents such as sulfur trioxide, oleum,
operate dedicated assets for bromination reactions, chlorosulfonic acid and sulfur trioxide amine complexes
including storage facilities, pipelines and safety for its own use and as sales products. This makes
systems. it possible to select the right reagent for the specific
requirement. The availability of sulfur trioxide from
pipeline for use as a reagent in multipurpose plants is
unique and a benefit for fine chemical production.
Benefits Benefits
• Long-standing experience in bromination reactions • Backward integration into key reagents
• Dedicated infrastructure for large commercial-scale • Sustainable production processes including
reactions recycling of off-gases
• Large variety of sulfonation and sulfation reagents
• Use of sulfur trioxide for fine chemical production in
multipurpose equipment
• Use of liquid sulfur dioxide as solvent
• Leading manufacturer of sulfur trioxide amine
complexes
14 CABB | SOLUTIONS AND CAPABILITIES
THIOALKYLATION METHYLATION
The reaction of (aromatic) nitro compounds with Dimethyl sulfate is the reagent of choice for the
alkyl sodium thiolates yields (aromatic) thioethers is methylation of O-, N- and S-functions like alcohols,
a straightforward synthesis. CABB is well-equipped thiols, carboxylic acids and amines to obtain the
for this type of reaction and for handling odorous corresponding ethers, esters, thioethers and methy
raw materials and products thanks to its in-house lated amines.
incineration unit for vent gases and waste.
With all the infrastructure for safe handling in place,
CABB is the ideal partner for methylation reactions.
Benefits Benefits
• Vast experience in thioalkylation reactions • Infrastructure for safe handling and production
• Handling of odorous raw materials, products and • Extensive expertise and experience in production,
waste handling, processing and logistics
(CH3O)2SO2 R CH3
R OH O
O O
(CH3O)2SO2 CH3
R OH R O
(CH3O)2SO2 R CH3
R SH S
(CH3O)2SO2 R CH3
R NH2 N
H
15
Carrying out large-scale lithiation reactions requires The Grignard reaction is an important method in
specific and dedicated infrastructure. CABB has this organic synthesis for the preparation of carbon-carbon
expertise and infrastructure on a commercial scale. single bonds, mainly by combining nucleophilic
We operate a dedicated system for lithiation reactions alkyl- or arylmagnesium halides with electrophilic
which includes storage facilities for bulk organic compounds such as aldehydes, ketones or esters to
lithium reagents, pipeline supply, safety measures and yield alcohols. It is also important for the preparation
automated processes. of boron derivatives which are subsequently used as
reactants in Suzuki-type cross-coupling reactions.
Benefits Benefits
• Expertise in lithiation reactions • Years of experience in commercial-scale Grignard
• Dedicated infrastructure for large commercial scale reactions
• S
afe and robust processes for the use of hazardous • In-situ preparation of Grignard reagents
reagents • Safe and robust production processes for the use of
hazardous reagents and intermediates
16 CABB | SOLUTIONS AND CAPABILITIES
In transition metal-catalysed cross-coupling reactions, The Wolff-Kishner reduction is a method for reducing
carbon-carbon bonds are formed. The Suzuki coupling carbonyl compounds to the corresponding alkanes
is the most prominent representative. The reaction in a direct and selective way. CABB carries out this
of aromatic halides with arylboronic derivatives, for chemistry using dedicated, continuously operated
example, yields the corresponding biphenyl derivatives. equipment. Continuous processes of this kind are
CABB has many years of expertise in this chemistry intrinsically safer, and a more regular and steady
including the recycling and reuse of precious catalysts. process results in higher yields and in products with
higher purity.
Benefits Benefits
• Safe and robust production processes • Expertise in adapting batch processes into
• Recycling and reuse of catalysts continuous ones
• Safe and robust production processes
17
OXIDATION REDUCTION/HYDROGENATION
Oxidizing thiols and thioethers with chlorine or Hydrogenation reactions at ambient or elevated
hydrogen peroxide is an advantageous and direct pressure, such as the reduction of aromatic nitro
method for obtaining sulfonyl chlorides and sulfones. compounds or the saturation of double bonds, can be
carried out as batch or continuous processes. CABB
CABB also carries out a variety of other oxidation has the equipment and expertise for both. The safe
reactions using air and catalysts. Some of these are handling of pyrophoric catalysts and their recycling
performed as continuous processes. and reuse are additional benefits.
Benefits Benefits
• Backward integration into key reagents • Safe and robust production processes
• Environmentally friendly recycling of off-gases • Safe handling of pyrophoric catalysts
• Hydrogen peroxide reactions conducted safely
• Expertise in continuous processes and their
handling
18 CABB | SOLUTIONS AND CAPABILITIES
CAPABILITIES
MULTI-STEP SYNTHESES
CABB is ideally equipped to perform demanding multi- We are able to carry out a vast range of standard
step syntheses of intermediates and active ingredients, chemical reactions based on our core chemistries in
and its plants and infrastructure enable efficient and order to support efficient manufacturing on a large scale.
sustainable production.
Chlorination Cl2, SOCl2, SO2Cl2, HCl, ... Friedel-Crafts acylation AlCl3, FeCl3
Bromination Br2, HBr, ... Amidation NH3 (g), NH3 (aq), NH2R, ...
Sulfonation SO3, HSO3Cl, H2SO4, ... Cyanation NaCN, …
Sulfochlorination HSO3Cl, ... Esterification/
Saponification
Alkylation Methylation, Thioalkylation,
Chloromethylation, ... Formylation
CABB is fully equipped to carry out demanding chemical CABB continuously improves its manufacturing pro-
syntheses in our multipurpose plants. This enables us cesses to guarantee safe production conditions that are
to start at low volumes in our pilot plant and optimize as efficient as possible. CABB cares about the environ-
processes across the product’s entire lifecycle up to full ment and has incineration units and a sewage treatment
commercial production. Designing and implementing plant on-site. Our Verbund and Recycling System ensures
safe and robust production processes is our top priority. we operate sustainably.
PRODUCTION EQUIPMENT
PRODUCT OVERVIEW
CARBOXYLIC ACIDS AND SALTS
Hexafluoroisopropylidene diphthalic
JAYHAWK 6FDA 1107-00-2
anhydride
CHLOROALKYL AMINES
N-(2-Chloroethyl)-diethylamine
DEC 869-24-9
hydrochloride
N-(2-Chloroethyl)-dimethylamine
DMC 4584-46-7
hydrochloride
CHLOROMETHYL ESTERS
CHLOROALKYL ETHERS
TERPENES
REAGENTS
BASE CHEMICALS
CROSSLINKERS
CABB Group is one of the world’s leading fine chemical custom manufacturers of active
ingredients and advanced intermediates. With approximately 1,100 employees and
six production sites in Europe, Asia and the U.S., we generate annual sales of about
half a billion euros. The company is headquartered in Sulzbach am Taunus, Germany.
We are a highly dedicated supplier and partner to leading companies, specifically in the
agrochemical, electronics, healthcare and specialty chemical sectors. We are one of the
world’s leading providers of high-purity monochloroacetic acid. We also produce a
portfolio of fine chemical intermediates for customers throughout the industry.
Publishing details:
Publisher: CABB Group GmbH Phone: +49 6196 9674 0 Managing Directors: Editor:
Otto-Volger-Strasse 3c Fax: +49 6196 9674 199 Valerie Diele-Baun, Markus Schürholz Gartner Communications, Neu-Isenburg, Germany
65843 Sulzbach am Taunus Email: info@cabb-chemicals.com VAT No. DE814439167, HRB 98571 Layout:
Germany www.cabb-chemicals.com erscheinungsform, Eltville am Rhein, Germany