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Process TechnologygyToine Paijens

[email protected]

ContentIntroductionProcess TechnologyProcess TechnologySupercritical fluid technologyHalal process technologyFeyeconConcluding remarks

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What is: Feyecon Asia?

Introduction

Prisna BVEcolada Ltd

X-tracts LtdHistolex SARL

Clean Algae SAFeyecon D&I BV

Algae Biotech SACleaNutrition SATispa Medical BVTispa Medical BV

Feyecon Asia Sdn BhdProderna Biotech Ltd

Echo Pharmaceuticals BVDyeCoo Textile Systems BV

Introduction

Technology development enterpriseImplementation of technology in business venturesClients include: Akzo Nobel, Avantium, Avebe, DSM, Duyvis, European Medical Contract Manufacturing (EMCM), Holland Colours, Imperial Chemical Industries (ICI), LodersC kl N tl O t l P t & G bl PCrocklaan, Nestle, Octoplus, Procter & Gamble, Purac, Quest, Solvay, Sulzer, TNO, Unilever

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THE OMNIPOTENTPROCESS INDUSTRY:FROM THE CRADLE TO THE GRAVE……AND BEYOND!

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Chemical technology sector profile

Some global characteristics

– 105 different products

– 1012 Euro annual turnover

– 107 employees

Production concentrated in EU USA Japan

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– Production concentrated in EU, USA, Japan.

– Production of bulk goods shifting towards other regions.

Source: http://www.wikipedia.org/

Dutch companies turnover statistics

A lt

Turnover of non-financial companies in The Netherlands (2005)

Trade

Transportation

Rental agencies

Education

Agroculture

Health care FisheryEnvironmental

protection

Hotels &

catering

Two-thirds of national turnoveris generated

by the industry

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IndustryConstruction

Trade

Source: http://www.cbs.nl

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Dutch industry turnover statistics

Industry turnover in The Netherlands (2005, excluding energy production and resource exploitation)

ChemicalsFurniture

Gl

Electrical

appliances

Transportation

vehicles

Machinery

Wood

Textiles &

leather

process technology input

Two-thirds of industry turnoveris generated using process technology

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Oil & coal

MetalsFoodstuffs

Paper

Glass

Plastics &

rubber

Source: http://www.cbs.nl

Presently only 25% of what goes into the pipe comes out as goods and services

Sustainable process technology??

NaturalResources

Goods andServices

Pollution, Wasteand EnvironmentalDisturbances

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Industry Sector Product tonnage Tons by-product/ton product Oil refining 106 – 108 < 0.1

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And it’s getting worse

Bulk chemicals 104 – 106 1 - 5Fine chemicals 102 – 104 5 – 50+ Pharmaceuticals 10 – 103 25 – 100+

The world appears to be facing tremendous challenges.

Solution requires a combined effort of politics, science and industry.

The world desperately needs NEW TECHNOLOGY

Process technology will be a key ingredient.

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7

Template of a chemical process

Raw material storage

Feed preparation

ReactionMixture i

storage preparation

Product Product Product

Recycle of: •Unreacted material•Auxiliary materials (process solvents, catalyst)

Mixture o

Concen-tratedmixtureProduct

storage separationpurification

Wastes By-products

Process solvents

Widely used throughout the chemical industry: Alcohols (MeOH, IPA), Benzene, Toluene, Xylene, Formaldehyde, Hexane, CH2Cl2, etc.

Used in:

– Synthetic ChemistryReaction medium on laboratory and industrial scale

Extensively used in work-up and purification (usually more than for reaction medium)than for reaction medium)

– CrystallisationRecrystallisation to purify compounds and prepare crystals

suitable for analysis

– Analytical Chemistry

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Other applications of solvents

Used much more widely than just synthetic chemistry: Coatings:Coat gs

– Paints, adhesivesSolvent usually removed by evaporation after application

leaving coating behindCoating removal

Cleaning– E.g. Dry cleaning – extensive use of perchloroethylene, a

known cancer suspect agent, which also contaminates d t ligroundwater supplies

Extraction– E.g. Coffee decaffeination (benzene, CH2Cl2)

Problems with VOC’s

Direct– Varying toxicity depending on nature of VOC, exposure method

and duration. E g DMF (teratogenic) CHCl (suspect carcinogen) E.g. DMF (teratogenic), CHCl3 (suspect carcinogen)

– Flammability (fire hazards)– Peroxide formation (usually ethers)

Indirect– Ozone depletion

Chlorofluorocarbons (CFC’s) now phased out– E.g. CF3Cl, lifetime in atmosphere 640 years, GWP 14,000– CCl4 – now much more limited use (35yrs, GWP 1400)

– Global warming potential (GWP)Does not have to be ozone depleting to have GWP

– E.g. HFC134a (CH2FCF3) used in refrigerants and air conditioning units, 14yrs, GWP 1300

– Environmental persistence

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Top 10 carcinogenic emissions to air (USA)

Rank Chemical Name Pounds (2009)

1 ACETALDEHYDE 12 807 3591. ACETALDEHYDE 12,807,3592. DICHLOROMETHANE 11,079,6043. FORMALDEHYDE 10,114,9094. TRICHLOROETHYLENE 7,940,3345. ETHYLBENZENE 6,432,9916. BENZENE 5,991,9937. NAPHTHALENE 2,663,5518. TETRACHLOROETHYLENE 2,332,193, ,9. 1,3-BUTADIENE 1,930,38110. CHLOROFORM 1,271,969

All volatile organic compounds (solvents!)

Current approaches to solvent replacement in synthetic chemistry

No solvent Water Water Carbon dioxide Ionic liquids Lactate esters Fluorous phase reactions

All have advantages and disadvantages which need to be considered when assessing suitability for replacement

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Carbon Dioxide

Similar advantages to water– Natural, cheap, plentiful (too much of it!)

Available in >99 9% pure form $110 per 25kg– Available in >99.9% pure form $110 per 25kg.

– By-product of brewing, ammonia synthesis, combustion Already being adopted in a variety of commercial processes (see

later) Non-toxic and properties well understood

– asphyxiant at high concentrations Easily removed and recycled, and can be disposed of with no net

increase in global COincrease in global CO2

– Simple product isolation by evaporation, to 100% dryness.

No solvent effluent Potential for product processing (extraction, particle formation,

chromatography etc.)


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What is: Supercritical Fluid Technology

Supercritical Fluid Technology

Uses a Supercritical Fluid = a gas (vapor)Uses a Supercritical Fluid = a gas (vapor) pressurised above its critical point

The technology is about the uses of a Supercritical Fluid instead of a common organic solvent (like ethanol, acetone, hexane ...), to extract/dissolve compounds from solids and fluid mixtures

Carbon Dioxide (CO2) is the most interesting gas for Supercritical application because of its convenient properties: Pc = 74 bar , Tc = 31 oC

CO2 passing the critical pointVapor:• Low density: : low capacity solvent power• Low viscosity, contacts/penetrates easily

Supercritical CO2

Increasing (gas) densityp

T < Tc T > TcT ~ Tc

Piston

Free liquid surface

Increasing pressure/temperature

Constant Supercritical fluid:CO2:Piston

Liquid:• High density, surface tension, does not contact/penetrate easily• High density: high capacity solvent power

Constant(liquid) density

Supercritical fluid:• High density• Low viscosity

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• Pc = 74 bar • Tc =31 oC

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Vapour Solid100

(SCF)

Liquid:High density: high capacity solvent power

Introduction

Vapour (gas)

Liquid

1

10Pressure (MPa) Critical point

Triple point

(SCF)High viscosity and surface tension: does not contact/penetrate easily into fibrous material

Vapour:Low density: low capacity solvent power

Low viscosity and no surface tension: contacts/penetrates easily into fibrous materialVapour (gas)

0.1

Temperature (K)

223 273 323 373173

contacts/penetrates easily into fibrous materialSupercritical fluid:

High density

Low viscosity

No or very low surface tension

Supercritical CO2

Pressure &

SF Technology

Raw material

Supercritical Fluid Extraction (SFE)

Liquid CO2 Solution of extract in supercritical CO2

Pressure &temperature

increase

Liquid CO2

Storageto be

extracted

Condensed CO2 (liquid )

Extract (liquid)

Pressuredecrease

Temperature decrease

Separation of extract and

CO2

Mixture of liquid extract + gaseous CO2

Gaseous CO2

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Advantages of application of supercritical CO2

• Product composition is easily tunable by means of

SF Technology

• Product composition is easily tunable by means of process parameters

• Processing at benign conditions

• Solvent is non toxic and environmentally friendly: product meets highest quality requirements

• End product is solvent free, meets highest quality specification (and Halal specifications)

→SF Technology enables you to produce high grade products with high added value

→Processing is inexpensive and highly sustainable


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Supercritical CO2

Pressure &

SF Technology

Dirty textiles

Application: dry cleaning of textiles



increase

Liquid CO2

Storage

textiles to be

cleaned

PressureTemperature Separation of

t t d


Organic dirt

Pressuredecrease

pdecrease

extract and CO2


Gaseous CO2

Supercritical CO2

Pressure &

SF Technology

D ’

Application: textile dyeing

Liquid CO2 Solution of dyestuff in supercritical CO2


increase

Liquid CO2

Storage

Dyer’s weed

PressureTemperature


Dyeing

Leftover dyestuff

Pressuredecrease

pdecrease


Gaseous CO2

y gtextiles

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SF Technology

No fresh water applied, no waste water, the process is extremely environmentally friendly compared to conventional textile dyeing.

The process is highly sustainable as both CO2

and leftover dyestuffs are fully recyclable

Supercritical CO2

Pressure &

SF Technology

Plants & h b t

Application: production of herbal extracts



increase

Liquid CO2

Storage

herbs to be

extracted


t t d


Herbal extracts, spice oils, oleoresins, essential oils

Pressuredecrease

pdecrease

extract and CO2


Gaseous CO2

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Supercritical CO2

Pressure &

SF Technology

Herbal

Application: production of pharmaceutics



increase

Liquid CO2

Storage

resources to be

extracted


t t d


Pharmaceutical precursors

decreasep

decreaseextract and

CO2


Gaseous CO2


High solvent power, transport properties of a gas, capacity of a liquid: fast high capacity processing

SF Technology

capacity of a liquid: fast, high capacity processing

Product composition is easily tunable by means of process parameters.

Processing at benign conditions (Pc = 74 bar Tc = 31oC):

better product quality

Solvent is non toxic and environmentally friendly: d t t hi h t h /f d dproduct meets highest pharma/food grade

requirements, including HALAL requirements

End product is solvent free

Processing is inexpensive, has little consumables as CO2 is easily recyclable

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Supercritical CO2

Pressure &

SF Technology

Fresh fruits

Application: extraction of water

Fresh-dried Food company



increase

Liquid CO2

Storage

fruits, vege-tables


t t d


Water

Pressuredecrease

pdecrease

extract and CO2


Gaseous CO2

Advantages of application of supercritical CO2 compared to freeze drying

Processing at benign conditions (P 74 b T 31 C)

SF TechnologyFresh-dried Food company

Processing at benign conditions (Pc = 74 bar Tc = 31oC):

better product quality: the fruits and vegetables are crispy and tasty

Solvent (CO2) is non toxic and environmentally friendly: product meets highest food grade requirements, including HALAL requirements

E d d i l fEnd product is solvent free

Processing is inexpensive, consumes little energy and has little consumables as CO2 is easily recyclable

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Supercritical CO2


increase

SF Technology

Liquid CO2

Storage

Malaysian natural

resources

Your business


increase

Pressuredecrease

Temperature decrease

Separation of extract and

CO2

Mixture of liquid extract


Flavours, aromatics Fragrances, essential oils Cosmetics, perfumesFood ingredients, colorants, antioxidants Nutraceuticals, vitamins, carotenoids (lycopene) Pharmaceutics, active molecules, peptidesProduct recovery/purification: removal of unwanted compounds


Gaseous CO2

Your product/application:

SF TechnologyYour plant

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Product composition is easily tunable by means of process

SF TechnologyYour business

Product composition is easily tunable by means of process parameters

Processing at benign conditions

Solvent is non toxic and environmentally friendly: product meets highest quality requirements

End product is solvent free, meets HALAL specification

→SF Technology enables you to produce high grade products with high added value

→Processing is inexpensive and highly sustainable

Processing Cost Estimates

Fresh CO : $ 100 / ton Kg CO / kg solid $ / kg solidFresh CO2: $ 100 / tonRecycled CO2: $ 20 / ton

Highest Supersaturation and yieldAcetaminophen from EthanolCholesterol from diethyl ether

Lowest CO consumption

Kg CO2 / kg solid $ / kg solidFresh Rec.

6050

65

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Lowest CO2 consumptionAcetaminophen from EthanolCholesterol from diethyl ether

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0.80.7

0.20.1

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Solid-liquid vs. solid-supercritical

SLE batch SLE conti SFE batch

minimum 250 t plant material/year

SLE-batch SLE-conti SFE-batchcost equipment 610 kE 1500 kE 2300 kecapacity / 8 hrs 200-300 t (400-600) t 250 tpreparation/mashing rarely often pulverisationprocess safety (co-solvent)product safety (co-solvent)Volume solvent (L:S) 10-20 3 ( 1 ) -cycle

flammability, toxicity …toxicity, quality, solubility ….

Volume solvent (L:S) 10 20 3 ( 1 ) cyclesolvent loss 10-15% 3-5% 3-5%solvent emmission 100-150 kg/t 30-50 kg/t -none-Energy /kg solid 8 kWh 3 kWh 0.8 kWhresidue disposal 120-380 E /t - 40% mass cattle feedwastewater /kg solid 500 l - 50% mass -none-


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CARBON DIOXIDE TECHNOLOGYExtraction Herb & spice extracts, Fragrances & perfume oils

Impregnation Textile dyeing

Micronisation Food and pharma ingredients

Feyecon

Micronisation Food and pharma ingredients

Encapsulation Food and pharma ingredients

Bioconversion Algal biodiesel, Algae derived oils

Cleaning Textile dry cleaning

Sterilization

PHARMACY & FOOD APPLICATIONSDrying Dried fruit, vegetables & powders

GMP facilities API and Intermediate products for clinical studiesGMP facilities API and Intermediate products for clinical studies, Ingredients for medical devices

Class D Cleanroom facility

HACCP facilities Micronisation food materials

EQUIPMENT & PROCESS DESIGNCustom engineered systems and components for supercritical separation and

particle technology.

TEAM

>30 team members

90% hold doctorate and/or post graduate degrees

Feyecon

90% hold doctorate and/or post-graduate degrees in: Physics, Chemical & Mechanical Engineering, Biochemistry, Pharmacy, Thermodynamics, Food Technology, Marine Sciences, Business development

INTELLECTUAL PROPERTYINTELLECTUAL PROPERTY

Over 30 patents owned in various fields: drying, particle formation, dyeing, dry cleaning, impregnation, density separation, measuring equipment, algae cultivation

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Feyecon

T i i & ltTraining & consultancy

Process & product development

Engineering and contracting of SF facilities

Joint ent res/b siness de elopmentJoint ventures/business development

Toll manufacturing


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Feyecon

Concluding remarks

SF Technology is green technology that can replace conventional separation processes based on volatile organic compounds (VOC’s)

SF Technology is the platform techno-logy to develop high grade, high added value HALAL products from Malaysia’s natural resources.

Thank you!for your attention

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