Umicore Grubbs Catalysts®

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www.umicore.com Offering the best of metathesis catalysts

First established in the 1960s, alkene metathesis Umicore PMC now offers secured access to the is considered to be the best method to synthesise best catalyst portfolio for metathesis. This is long complex alkenes through the use of highly in addition to the strong global operating and efficient and selective catalytic reactions. industrial scale manufacturing expertise that it has established over its decades of experience Employing a ruthenium metal complex, in the industry. Umicore’s range of services are metathesis enables the simple synthesis of tailored to meet your specific metathesis needs. carbon-carbon double bonds. These reactions Our experts can help support development provide efficient routes to product synthesis by processes; from scaling a reaction or devising ensuring minimal waste due to the formation new reaction routes, to screening the appropriate of less toxic by-products, high activity and catalyst to maximise your product formation. high stereoselectivity. Working together with Umicore means Following decades of research and development unparalleled access to Grubbs Catalysts® and our in the field of metathesis, Umicore provides a development expertise; together we can work comprehensive portfolio of catalysts. In early to develop your specific metathesis reaction. 2018, we expanded our offerings to include the world-class Grubbs Catalysts® intellectual property, following Umicore’s acquisition of Materia’s proprietary metathesis technologies. These catalysts, developed by Nobel laureate Prof. Robert H. Grubbs and his team, deliver the best-in-class conversion, enabling robust alkene conversions.

“Working together with Umicore means unparalleled access to Grubbs Catalysts®” Contents

Metathesis: the key features ...... 4 Choose your metathesis ...... 5 Catalyst product list ...... 8 General reaction procedure ...... 11 Supportive services ...... 13 About Umicore PMC...... 14 4

Metathesis: the key features

Due to its versatility, metathesis can be used to synthesise a range of useful products across multiple markets. The key features of metathesis include:

Functional group tolerance: Modern active Activity and catalyst longevity: For chemical pharmaceutical ingredients are among the most applications driven by aggressive cost targets, complex molecules synthesised on commercial scale. ruthenium-based metathesis catalysts have Ruthenium-based metathesis catalysts succeed in demonstrated unparalleled activity under rugged forming key bonds in even the most challenging conditions. Renewable feedstocks such as soybean oil substrates, such as the macrocyclic peptide core can be converted into specialty chemical products with of HCV NS3 protease inhibitors like ciluprevir, turnover numbers in the hundreds of thousands. Thus, simeprevir, and related compounds used to treat even in high-volume, low-margin products, metathesis hepatitis C infections. can deliver significant cost advantages. Stereoselectivity: Recent advances in ruthenium- based metathesis catalysts offer opportunities for stereoselective metathesis reactions. In particular, Z-selective and stereoretentive catalysts offer new routes for chemists to control the E:Z ratio of newly formed alkenes. While this feature is potentially useful in almost any application, it is particularly advantageous to the production of insect pheromones, which must be prepared in the correct ratio of olefin isomers to be effective as natural deterrents for crops.

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Chemicals For inquiries and additional information please contact

Umicore AG & Co. KG Rodenbacher Chaussee 4 63457 Hanau-Wolfgang Germany

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Choose your metathesis

With many versatile reactions to choose from, identifying the right catalyst for your reaction also relies on identifying the right metathesis reaction. Be it ring-closing metathesis, which can be used to synthesise complex polycyclic molecules, or cross metathesis, involving the intermolecular reaction of two unconnected alkenes, we have the on-hand expertise to discuss the best routes to your product, ensuring project success.

Ring-closing metathesis Ring-closing metathesis is a common metathesis reaction for any scientist needing to synthesise mid- and macro- sized rings, as well as offering an efficient route to synthesise strained or sterically hindered rings. Proceeding via an intermolecular process, this reaction can be made almost irreversible following appropriate reaction optimisation.

Mid-sized ring-closing metathesis

Preferred Catalysts Optimal Catalyst Loading Conditions Umicore Grubbs catalyst M2, M2a (C848) 3-5 mol% Concentration: Depending on ring size: 1.0 M Umicore Hoveyda-Grubbs Catalyst M72 (5-membered ring), 0.5 M (6-membered ring) (C627), M72 SI(o-Tol), M73 Temperature: 40-100 oC

H Me H O O Si(tBu) H Me H 2 5 mol% M2a (C848) O O O Si(tBu) O O O 2 H H H DCM, 40 OC O O O H H H O 85% yield

Ring-closing metathesis to form an oxepane ring embedded in (-)-gambieric acid with applications in the pharmaceutical industry. Ref: Organic Letters 2015, 17, 4694

O O 0.2 mol% M72 (C627) N N MeO2C 2,6-dichlorobenzoquinoneMeO2C H O 0.13 M toluene H O 3 mol% M2a (C848) 100 OC Me CO H DCM, 40 °C Me CO H Me N 2 simultaneous slow addition N 2 OH Me O H O N of substrate and catalyst O N O 95% yield O O O

Ring-closing metathesis to yield the synthesis of an 8-membered ring structure of91% serpendione. yield Ref: Tetrahedron Letters, 2005, 46, 1149

O EtO C O 2 N EtO C 5 mol% M2a (C848) 2 N DCM, 40 °C H 6 mol% M72 SI(o-Tol) (C571) N 1 atm ethene N 92% yield toluene, 100oC O O Ring-closing metathesis in the synthesis of (-)-stemoamide, a root extract used in Chinese and Japanese folk medicine. 89% yield Ref: Journal of Organic Chemistry, 2007, 72, 4246

CO2Me

CO2Me 6 29 ppm M2 CO Me R 2 6 toluene, 60oC

6 Me02C

Desired CM product Conversion Productive TON acrylate (R=H) 58% 6000 crotonate (R=Me) 96% 31110

5 mol% catalyst OAc OAc DCM, 40oC Catalyst Yield C571 60% C627 78% C711 98% For inquiries and additional information please contact

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H Me H O O Si(tBu) H Me H 2 5 mol% M2a (C848) O O Macrocyclic ring-closing metathesisO Si(tBu) O O O 2 H H H DCM, 40 OC O O O Preferred Catalysts Optimal Catalyst Loading ConditionsH H H O Umicore Grubbs catalyst M2, M2a (C848) 3-10 mol% Concentration:85% 0.1yield - 0.05 M Umicore Hoveyda-Grubbs Catalyst M72 Temperature: 40-100 oC (C627), M73

O O 0.2 mol% M72 (C627) N N 2,6-dichlorobenzoquinone O 0.13 M toluene O 100 OC

N CO2H N CO2H H simultaneous slow addition H O N of substrate and catalyst O N O O O O

91% yield

Ring-closing metathesis to form a 20-membered macrocycle used as a protease inhibitor in the pharmaceutical industry. Ref: Journal of Organic Chemistry, 2012, 77, 3820

6 mol% M72 SI(o-Tol) (C571) N 1 atm ethene N o toluene, 100 C O O O O Ph Ph 89% yield N 15 mol% M2a (C848) N 0.58 mM DCM, reflux O O O O

R R

CO2Me 90% yield

CO2Me 6 29 ppm M2 CO Me Formation of a key intermediateR in the preparation2 of the cytotoxic marine natural6 product (-)-spongidepsin. toluene, 60oC Ref: Organic Letters, 2010, 12, 4392 6 Me02C

Desired CM product Conversion Productive TON Sterically demanding ring-closingacrylate metathesis (R=H) 58% 6000 crotonate (R=Me) 96% 31110 Preferred Catalysts Optimal Catalyst Loading Conditions Umicore Hoveyda-Grubbs 3-10 mol% Concentration: Depending on ring size: 1.0 M Catalyst M72 (C571) (5-membered ring), 0.5 M (6-membered ring) Temperature: 40-100 oC

OEt 5 mol% catalyst EtOAcO O OAc O Ph DCM, 40oC N 10 mol% M72 SI(o-Tol) (C571)Catalyst Yield C571 Ph60% N toluene, 80 °C C627 78% C711 98% N N

Ph Ph 82% yield

Formation of a trisubstituted alkene scaffold used for SAR exploration. Ref: Bioorganic Medicinal Chemistry, 2013, 21, 5707 For inquiries and additional information please contact

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Cross metathesis Bringing together two unconnected alkenes in an intermolecular reaction, cross metathesis is an extremely useful reaction that can result in the efficient synthesis of complex and long carbon-carbon chains.

Cross metathesis of electron-deficient alkenes

Preferred Catalysts Optimal Catalyst Loading Conditions Umicore Grubbs Catalysts M2 and M2a (C949); 1-5 mol% Concentration: 1 M or greater Umicore Hoveyda-Grubbs Temperature: 40-60 oC Catalyst M72 (C627), M73 and M73 SIPr

CO2Me CO2Me 6 29 ppm M2 CO Me + R 2 6 toluene, 60°C 6 MeO2C desired CM product Conversion Productive TON acrylate (R = H) 58% 6000 crotonate (R = Me) 96% 31110

Biscarbocylic acid formation used as precursors to multiple fine chemical products. Ref: ChemSusChem, 2014, 8, 1143

Ph

O M2a (C848) + Ph O DCM, 40 °C (CH2)12CH3 O

O (CH2)12CH3

68% yield Synthesis of ß-lactone structures bearing a variety of alkyl chains at the 3-position. Ref: Bioorganic & Medicinal Chemistry Letters, 2015, 25, 317

Synthesis of trisubstituted linear alkenes

Preferred Catalysts Optimal Catalyst Loading Conditions Umicore Grubbs Catalysts M2 and M2a (C949); 1-5 mol% Concentration: 1 M or greater Umicore Hoveyda-Grubbs Catalyst M72 (C627), Temperature: 40-60 oC M72 SIPr (C711) and M73

OAc OAc

5 mol% M2 (C848) + O 2 neat, 80 ºC, 2 h O 2

with vacuo (33 mbar) 83% yield 67:33 E:Z

The preparation of vitamin E intermediates by cross metathesis of trisubstituted and disubstituted alkenes. Ref: Helvetica Chimica Acta, 2006, 89, 797 For inquiries and additional information please contact

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A selection of Umicore Grubbs Catalysts®

M1 series Ruthenium Metathesis Grubbs Catalysts® 1st Generation

M1+M11 Ligand L Trade Name Chemical Formula CAS Number L Cl Ph Ru Umicore PCy Grubbs Ru(PCy ) (Ind)Cl 250220-36-1 Cl 3 3 2 2 Catalyst® M1 L

M1a Umicore Grubbs PCy Ru(PCy ) (benzylidene)Cl 172222-30-9 L 3 Catalyst® M1a 3 2 2 Cl (C823) Ru Cl Ph Umicore L Grubbs PCy Ru(PCy ) (butenylidene)Cl 194659-03-5 3 Catalyst® M1b 3 2 2 M1b (C801)

L Cl Umicore Ru i i Bu-phobane Grubbs Ru(Bu-phobane)2(Ind)Cl2 894423-99-5 ® Cl Catalyst M11 L

M2 series Ruthenium Metathesis Grubbs Catalysts® 2nd Generation

NHC Ligand L1 Ligand L2 Trade Name Chemical Formula CAS Number

M2a Umicore NHC Grubbs SIMes PCy - (SIMes)Ru(PCy )(benzylidene)Cl 246047-72-3 Cl 3 Catalyst® M2a 3 2 Ru (C848) Cl Ph L Umicore Grubbs SIMes PCy3 - ® (SIMes)Ru(PCy3)(butenylidene)Cl2 253688-91-4 M2b Catalyst M2b (C827) NHC Umicore Cl SIMes PCy3 Cl Grubbs (SIMes)Ru(PCy3)(Ind)Cl2 536724-67-1 Ru Catalyst® M2 Cl L Umicore

SIMes PPh3 Cl Grubbs (SIMes)Ru(PPh3)(Ind)Cl2 340810-50-6 Catalyst® M20 M2 + M20 + M22 Umicore Grubbs NHC SIPr PPh Cl (SIPr)Ru(PPh )(Ind)Cl 1307233-23-3 3 Catalyst® M20 3 2 L 2 Ph SIPr Ru Cl Umicore i i SIMes Cl P(OPr)3 Grubbs (SIMes)Ru(P(OPr)3)(Ind)Cl2 1255536-61-8 L 1 Catalyst® M22 For inquiries and additional information please contact

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M3 series Ruthenium Metathesis Grubbs Catalysts® 2nd Generation (N ligands)

M31 NHC Ligand L1 Ligand L2 Trade Name Chemical Formula CAS Number

NHC Umicore SIMes py - Grubbs (SIMes)Ru(py)(Ind)Cl 1031262-76-6 Cl Ph 2 Ru Catalyst® M31 Cl L 1 Umicore Grubbs SIPr py - (SIPr)Ru(py)(Ind)Cl 1304756-39-5 Catalyst® M31 2 SIPr M36a + M37a Umicore Grubbs SIMes py py (SIMes)Ru(py) (benzylidene)Cl 357186-58-4 NHC Catalyst® 2 2 Cl M31a (C727) L 2 Ru Umicore Cl Ph Grubbs SIMes 2-Br-py 2-Br-py ® (SIMes)Ru(2-Br-py)2(benzylidene)Cl2 900169-53-1 L 1 Catalyst M37a (C884)

M5 series Ruthenium Metathesis Grubbs Catalysts® 2nd Generation (O ligands)

M51 + M52 NHC R Trade Name CAS Number

NHC ® Cl SIMes Me Umicore Grubbs Catalyst M51 1031262-71-1 Ru Cl O O SIMes H Umicore Grubbs Catalyst® M52 1014701-61-1 R

M7 series Ruthenium Metathesis Hoveyda-Grubbs Catalysts® 1st / 2nd Generation

M70 NHC R Ligand L Trade Name CAS Number

L ® Cl Umicore Hoveyda-Grubbs Catalyst - - PCy3 203714-71-0 Ru M70 (C601) Cl Umicore Hoveyda-Grubbs Catalyst® SIMes NH(CO)CF - 1025728-56-6 O 3 M71 SIMes

Umicore Hoveyda-Grubbs Catalyst® SIPr NH(CO)CF - 1212008-99-5 3 M71 SIPr

Umicore Hoveyda-Grubbs Catalyst® SIMes H - 301224-40-8 M71 + M72 + M73 M72 (C627)

Umicore Hoveyda-Grubbs Catalyst® NHC SIPr H - 635679-24-2 Cl M72 SIPr (C711) Ru Umicore Hoveyda-Grubbs Catalyst® Cl SI(o-Tol) H - 927429-61-6 O R M72 SI(o-Tol) (C571)

Umicore Hoveyda-Grubbs Catalyst® SIMes NH(CO)OiBu - 1025728-57-7 M73 SIMes

Umicore Hoveyda-Grubbs Catalyst® SIPr NH(CO)OiBu - 1212009-05-6 M73 SIPr For inquiries and additional information please contact

Umicore AG & Co. KG Rodenbacher Chaussee 4 63457 Hanau-Wolfgang Germany

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M8 series Bis-NHC Ruthenium Metathesis Grubbs Catalysts® 2nd Generation

NHC Trade Name Chemical Formula CAS Number M80

NHC Cl Ph Umicore Grubbs Catalyst® Ru SIMes (SIMes) Ru(Ind)Cl 1383684-54-5 M80 (C975-bis) 2 2 Cl

NHC M80a NHC Cl Umicore Grubbs Catalyst® M80a Ru SIMes (SIMes) Ru(benzylidene)Cl 508172-19-8 (C875-bis) 2 2 Cl Ph NHC

M80b

NHC Cl Umicore Grubbs Catalyst® M80b SIMes (SIMes) Ru(butenylidene)Cl Ru (C853-bis) 2 2 Cl NHC

MZ series Z-Selective Ruthenium Metathesis Hoveyda-Grubbs Catalysts® 2nd Generation

Trade Name CAS Number MZ1c

N N

Umicore Hoveyda-Grubbs O Ru 1352916-84-7 Catalyst® MZ1c (C633) N O O O

MZ2c

N N

Umicore Hoveyda-Grubbs O Ru 1451807-77-4 Catalyst® MZ2c (C675) N O O O

iPr iPr iPr iPr Legend SIMes N N SI(o-Tol) N N N N N N SIPr N N iPr iPr iPr iPr

SIMes SIPr SIMes SIPr

Please visit our website to find a comprehensive list of Umicore Grubbs Catalysts® www.pmc.umicore.com For inquiries and additional information please contact

Umicore AG & Co. KG Rodenbacher Chaussee 4 63457 Hanau-Wolfgang Germany

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General reaction procedure

Metathesis reactions are versatile reactions that can be performed in most situations without the need for extensive optimisation. But in those difficult synthetic situations, our team of industrial experts will tailor each reaction to the specific requirements for the project, ensuring precise and selective product formation. There are many factors that must be considered when devising any reaction, including those from catalyst loadings, reaction conditions and the functionality of the product.

Optimising the catalyst

For general metathesis reactions, Umicore Hoveyda-Grubbs Catalyst M72 (C627) and the Umicore Hoveyda-Grubbs Catalyst M73 series are recommended. These catalysts initiate at room temperature and are highly stable enabling simple storage and handling. In metathesis reactions involving sterically hindered alkenes, it may be necessary to use a more specialized catalyst. For instance, the Umicore Hoveyda-Grubbs Catalyst M72 SI(o-Tol) (C571) catalyst can be used to perform sterically hindered ring rearrangement reactions owing to the decreased steric bulk of the protruding ligands.

6 mol% M72 SI(o-Tol) (C571) N 1 atm ethene N toluene, 100 °C O O

89% yield

Alternatively, if your substituents are bulky, substituted alkenes, the Umicore Hoveyda-Grubbs Catalyst M72 SIPr (C711) catalyst could result in a higher yield.

5 mol% catalyst OAc + OAc DCM, 40 °C

Catalyst Yiel d C571 60% C627 78% C711 98%

As long as reaction conditions are chosen carefully, high loadings of catalyst are not necessary. In some cases, using more catalyst may lead to unwanted side reactions. Even for challenging reactions, loadings less than 1 mol% can be effective given the careful choice of other reaction parameters.

Legend SIMes SI(o-Tol) SIPr For inquiries and additional information please contact

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Choosing the right conditions

Choosing the right operating conditions for your properties of the solvents. Preferred solvents include industrial reaction relies on careful optimisation. Finding non-polar, hydrocarbon-based solvents, chlorinated the right temperature is vital for catalyst initiation, solvents and peroxide-resistant ethers, due to their with low temperatures being advantageous from an weak binding affinity to the catalyst complex. environmental perspective. Umicore catalysts typically Finally, ensuring the catalytic reaction is devoid of initiate at low temperatures, between room temperature catalyst poisons is also vital. Peroxides oxidise the and 40 oC. Furthermore, the exact concentrations of metal-carbene bond, rendering the catalyst inactive. reagents vary according to the specific metathesis Furthermore, ethene should also be removed as its reaction: cross metathesis requires concentrated presence could also result in catalyst decomposition. In solutions, macrocyclizations require dilute solutions addition, all of the Umicore Hoveyda-Grubbs catalysts and other ring-closing metathesis reactions require are air and moisture stable as solids, but in solution are intermediate concentrations. vulnerable to oxygen. Therefore, reactions need to be Likewise, choosing the appropriate solvent to mediate run in the presence of argon or nitrogen gases to ensure metathesis reactions relies on understanding the various the exclusion of oxygen.

Preferred solvents Usable in certain conditions Not recommended for use Toluene, xylenes, mesitylene MeOH, EtOH, nBuOH DMSO, DMF, NMP

Heptanes, hexanes THF, ether MeCN

DCM, DCE, chlorobenzene Water (neutral/acidic) Pyridine and other amines

EtOAc, iPrOAc Water (basic)

TBME, Me-THF

Optimising the reaction procedure

Beyond conditions, there are multiple aspects of Metathesis reactions that bring together two terminal the synthetic procedure that must be considered for alkenes produce ethene as a by-product. Although the successful completion of any reaction. Strongly ethene is a gas, it is soluble in organic solvents and can coordinating functional groups must be masked so as remain in the reaction mixture. Ensuring that ethene or to not disrupt the catalyst activity; the concentration of any other gaseous by-product is efficiently removed will the various substrates must be optimised to prevent drive the reaction equilibrium toward completion. This substrate polymerisation, but encourage the desired can be accomplished by bubbling an inert gas through format of metathesis. the reaction mixture over the course of the reaction. On scale, this technique is used frequently to help Furthermore, to prevent unwanted side-effects of maximise catalyst lifetime. metathesis reactions such as the isomerisation of alkenes, it is sometimes necessary to use additives to For the selective formation of cis- or Z-alkenes, one can suppress the unwanted reactions. For instance, mild use the Umicore Hoveyda-Grubbs Catalysts MZ1c (c633) acids such as acetic acid can be added to reactions to and Umicore Hoveyda-Grubbs Catalysts MZ2c (c675), prevent hydride formation, as illustrated in the following which provide selectivity in both ring-closing or cross diagram: metathesis reactions.

5 mol% M2 (C848) O O O DCM, 40 OC

no additive: <5% 95% with 10 mol% 1,4-benzoquinone: >95% none with 10 mol% AcOH: >95% none For inquiries and additional information please contact

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Supportive Services As leading experts in catalyst research and development, Umicore has decades of experience developing ground-breaking chemistry. We offer a range of supplementary services to help scale your chemical reaction, regardless of your reactants, products and market. We work across your development pipeline to devise strategies to deliver solutions to solve any optimisation challenges faced along the process; from research to product launch and beyond.

We will work with you to define the best route to your experience in the manufacturing and development synthetic target or optimise the production to maximise process means we know what expertise needs yield or selectivity. This could be through identifying new to be deployed at each stage of a project. reaction routes by devising alternative retrosynthesis, At Umicore, we have the expertise in global which are then screened as potential reactions at all manufacture and development to ensure the successful scales of the industry. and reliable supply of reagents, as well as the technical Understanding the best route to your product comes expertise to identify the best catalyst and conditions down to understanding the complex chemistry driving for your reaction. Our solutions are tailored to each of your reaction. We work across all phases of a project’s our customer’s reactions and each catalyst loading is pipeline, from the initial investigations into the optimised to the requirements of each project. viability of catalytic reactions, to optimising processes Let’s work together to accelerate your product synthesis. for large-scale production. Our understanding and

Research Preclinical phase Clinical phases Launch & marketing

Catalysts & parameter screening

Catalysts Supply

Process Development & Optimization

Scale up For inquiries and additional information please contact

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About Umicore Precious Metals Chemistry

Umicore Precious Metals Chemistry is part of the Umicore group, a global materials and technology company with locations around the world. With over 50 years’ experience working with customers across the globe, Umicore has helped to develop innovative metals and materials technology to help solve the most challenging chemistry problems.

Taking a collaborative and simple approach to its In addition to Umicore PMC’s chemical and engineering business practice, Umicore PMC operates in many of the expertise, sustainability lies at the heart of the key markets that are vital to developing the solutions Umicore PMC business and the wider Umicore group. to real-world problems. This includes: pharmaceutical Sustainability is materialised through Umicore PMC’s development, fine chemicals, automotive and drive towards developing efficient methods of recycling electronics. Within these markets, Umicore PMC offers precious metals and discovering new more long-term many competitive technologies that develop and deliver sustainable chemical reactions. ground-breaking innovations. Collaboration is at the centre of success and innovation. With a comprehensive portfolio of catalysts including the By working together in multiple aspects of R&D, process Grubbs metathesis, cross coupling and hydrogenation development and industrial manufacturing, we can create catalysts, Umicore PMC offers an extensive portfolio of innovative and cost-effective industrial synthesis for chemical technologies to the market. your project.

We understand the rapidly changing needs of our clients throughout the world, & provide:

Innovative, Collaborative Process Commercial-scale Supply chain metal-based R&D development manufacturing expertise chemistry and scale up Let’s work together to create ground-breaking chemistry For inquiries and additional information please contactFor inquiries and additional information please contact

Umicore AG & Co. KG Umicore AG & Co. KG Rodenbacher Chaussee 4 Rodenbacher Chaussee 4 63457 Hanau-Wolfgang 63457 Hanau-Wolfgang Germany Germany

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