Introduction to Avantium Technologies

Capabilities and proven benefitsfor chemical and petrochemical customers

Accelerating

R&D

Ed de Jong

Oktober, 2007

Company overview

• Privately held, independent research company• We provide

– contract research services– innovative technologies

on basis of high-speed parallel experimentation• Core expertise: catalysis and crystallization• Main markets:

– Petrochemical, Chemical, Refinery and Pharmaceutical industries

• Based in Amsterdam

Organization

• We employ a highly educated workforce of >100 people– Crystallographers, Chemical Engineers, Inorganic and Organic

Chemists, Catalysis Specialists, Applied Statisticians, IT Specialists, Data base engineers, etc.

• Strong growth in coming period

Value proposition

Avantium provides commercially driven R&D solutionsaimed at increasing productivity:

• Greater speed (more experiments/time unit)• Greater efficiency (lower cost /experiment)• High-quality data (reproducible, good correlation to

larger scale equipment, rational experimental design techniques, modeling)

This allows our customers to innovate faster than theircompetitors and to get more value out of their R&Dinvestments

Services

Avantium provides the following services to the (petro)chemical, refinery and pharmaceutical industry:�Catalyst discovery, optimization, ranking�Large catalyst library�Rational Design and Modeling (kinetics, RSM) �Crystallization optimization, polymorph screening & salt selection�Development of High Throughput Methodologies, Performance & Analytical Tools and Models

Proven benefits

Avantium has an excellent track record in collaborative R&D programs:– Discovery of new catalysts for a range of applications – Catalyst optimization for bulk-chemical processes– Catalyst ranking for refinery applications (for catalyst

change-out)– Discovery of >100 previously unknown crystal forms

(drug polymorphs)– Development of various dedicated HT workflows and

platforms

Proven applications Heterogeneous catalysts

AldolCondensation

AldolCondensation

Selectivehydrogenation

Selectivehydrogenation

DehydrationDehydration

Selective Oxidation

Selective Oxidation

HydrodearomatizationHydrodearomatizationWater gas shiftWater gas shift

Selective hydrogenation

Selective hydrogenation

AmmoxidationAmmoxidation

Gas Phase

Trickle

Flow

HydrodesulfurizationHydrodesulfurization

MetathesisMetathesis

IsomerizationIsomerization

Fixed Bed

Gas to liquidsGas to liquids

Technology platforms

Avantium has a wide experience in development and construction of High Throughput equipment and methodologies.

At Avantium we have a range of proprietary high-throughput experimentation workflows with proven capabilities, a.o.

• Heterogeneous catalyst preparation• Parallel fixed bed reactors• Parallel batch reactors• Crystallization research

Catalyst preparation

Avantium has a range of catalyst preparation platforms:

• Automated parallel impregnation• Automated parallel precipitation• Other techniques (drying, grinding, sieving,

calcination, reduction)• Testing of real catalysts• Performance determined by composition and

preparation method

Automated heterogeneous catalyst synthesis

• Automated solids impregnation

• Automated precipitation

• Hydrothermal synthesis

• High T treatment

Parallel batch technology

Avantium’s has a range of parallel batch systems to accommodate a broad range of chemistries:

• Experience with a.o. hydrogenation, oxidation, hydroformylation, selective reduction, coupling reaction and asymmetric synthesis

• Scale: 1 – 100 ml• Pressure: up to 100 bar• Temperature: up to 180ºC

Batch reactors

2x40 reactors, 8-10 ml

12 reactors, 10-100 ml

16x12 reactors, 2 ml

Parallel fixed bed technology

Avantium’s proprietary flow-reactor technology (“Nanoflow”):• Wide range of temperature and pressure capabilities• Gas and trickle flow operation• Proven for a wide range of applications, such as oxidation,

hydrogenation, isomerization, GTL, FT, HDS, HDA• Aim to test under industrial relevant conditions• Good track record in running extensive screening

programs and proven ability to modify the equipment for new applications

Nanoflow philosophyTesting under relevant conditions:

• Real pressure, temperature and feed

• Isothermal conditions• Plug flow conditions• No mass transfer limitations• No catalyst bypassing

(wetting !)• Limited pressure drop

Intrinsic kinetics can be derived from Nanoflow data

Nanoflow reactors (0.05-1 ml)

Parallel fixed bed reactors

Multiple systems available for different applications

• High viscous feed• High conversion

reactions• High temperatures and

or pressures• Small effluent streams• Gas/liquid separation• Gas and liquid analyses

Key figures

• Both gas and liquid feed options– Low flow rates possible (<1 Nml/min hydrogen)

• Possibility to have heated feed system (up to 180°C)• 16 to 96 reactors per system• Reactor diameter 2mm, bed length 70mm

– Option for longer reactors (350mm bed length)• Typical reactor volume 0.05 to 0.2 ml

– Larger reactor up to 1.0 ml• Different options for reactor effluent handling

– Heated up to 180°C– Parallel pressure regulator for gas/liquid effluent

• Analysis– Online (GC and others)– Offline (various techniques)

Fixed bed units Overview of Units at Avantium

• NF 20 � 32-64 Reactors Gas phase, 50 bar and 550 °C• NF 21 � 32-64 Reactors Trickle flow, 50 bar and 550 °C • NF 30 � 16 Reactors Trickle flow, liquid/gas sampling, 100 bar and 550°C• NF 31 � 48 Reactors Trickle flow, liquid sampling, 100 bar and 550°C• NF 32 � 32 Reactors Trickle flow, liquid sampling, 100 bar and 550°C,

high temperature feeding

• NF 33-36 � 64 Reactors gas phase, 100 bar and 550°C• NF 40 � 24 Reactors Full liquid, liquid sampling

• NF 50 � 16 Reactors gas phase, 0.1-1 bar and 750°C• NF 60 � 64 reactors 60 bar, 850°C

Flowrence, Fixed bed, 16 parallel reactors

Crystal 16, 16 parallel crystallizations

Block 96, 96 parallel Batch reactions

Bio-Fuels and Bulk Chemicals

Avantium chooses for catalytic routes

• Carbohydrate chemistry• Fatty biomass upgrading• Fischer-Tropsch catalysis

Carbohydrate Chemistry

• Non-enzymatic cellulose to glucose route developments/fundamental/mechanistic research

• (Fundamental) catalyst development for high water content feeds (at high T, p)

• Selective pyrolysis of (well defined) biobased feeds (zie bv. Aida et al. J. Supercritical Fluids 40, 381 (2007)

• Mechanistic research (incl. modelling) into sugar dehydration (see e.g. Dumesic 2006, 2007; Qian et al. Appl Biochem and Biotech 121-124, 989 (2005))

Topics of interest

• Fatty acid/ester conversion to primary fatty alcohols/amines

• Transesterification• Hydrotreating• Glycerol conversion

Example: Palmoil Fatty ester hydrogenolysis (Avantium project)

Project Goals• Development of novel catalysts for the

hydrogenolysis of methyl ester or wax ester to fatty alcohols.

• Novel catalysts to enable operation at lower pressure, lower temperature and/or longer operation cycle

– e.g. 50 bar– >> 50 days– Conventional process is operated at 200-300°C and

200-250 bar.

Phase 1: Conversion of C12 fatty acid to C12 Alcohol

Performance depends strongly on support type.Main byproduct is lauryl laurate; negligible production of dodecane.

• Mono-, bimetallic

and trimetallic

catalysts.

• Color by metal 3;

shape by metal 2.

• Results of 725

experiments.

Phase 3: Duration Test 2Example of specific interest:understanding catalyst deactivation

•Novel catalyst has higher stability and higher yield than best commercial catalyst at commercially most relevant conditions

•Novel catalysts give less byproducts

Conclusions

Potential Benefits

• Less reactor downtime.

• Reduced catalyst consumption.

• Reduction in utility cost: 40-50% reduction in H2 recycle compressor & aftercooler duty.

• Grassroots plant: reduction in capex investment (possibility to operate at lower pressure).

Fischer-Tropsch catalysis

• For Avantium this is in the services domain• Mainly observer role

Thank you for your attention

Avantium Business model

Deal structure:• Fee for service• Shared risk/reward arrangement is possible;

related to achieving technical milestones• Master Services Agreement to govern relationship

and multiple projects• Avantium sells high-throughput workflows and

components thereof, including licenses of proprietary features (technology transfer)

Typical Collaboration flow

Feasibility program (3-6 months)

Research collaboration (1-2 years)

Technology transfer

Project scoping and contract discussions

Confidentiality Disclosure Agreement

Master Service Agreement

Collaboration mode

• Synergy: combine expertise of customer (application) and Avantium (high-throughput techniques and data-processing)

• Close collaboration between technical teams: weekly conference calls with Webex, and monthly face-to-face meetings

• Customer has full insight in project data (customized database) and project progress

• Steering committee to oversee collaboration, project resourcing, program directions and to resolve commercial/IP issues

Intellectual property rights

Starting point for division of Intellectual Property Rights:• Customer and Avantium own all IPR on their existing

technology and know-how• Customer owns all new product and process related IP• Avantium owns all new IP on hardware, software and

research methodologies

Thank you for your attention

Thank you for your attention

Method developmentFast sequential testing

Automation software sequential testing

• Sequential testing of up to 96 catalysts

• Fast test method of 5 to 60 seconds

• Temperature measurement of catalyst bed

• Experimental data and gas analysis stored in database

Data analysis

SQL database

Specific calculations (e.g.

X, S, STY)

Custom-made tools (e.g.

interpolation)

MS Access database

Visualization (Spotfire)

Catalyst Testing

Catalyst Preparation

Catalyst Characterization

Recipe Process log data

Reactor Loading

Catalyst composition e.g. Spectra

Data analysis

SQL database

Specific calculations (e.g.

X, S, STY)

Custom-made tools (e.g.

interpolation)

MS Access database

Visualization (Spotfire)

Catalyst Testing

Catalyst Preparation

Catalyst Characterization

Recipe Process log data

Reactor Loading

Catalyst composition e.g. Spectra

Data analysis

SQL database

Specific calculations (e.g.

X, S, STY)

Custom-made tools (e.g.

interpolation)

MS Access database

Visualization (Spotfire)

Catalyst Testing

Catalyst Preparation

Catalyst Characterization

Recipe Process log data

Reactor Loading

Catalyst composition e.g. Spectra