dsm coating resins 2007/presentations/external/nvvt 0 coating resins on bio-based raw materials...

DSM Coating Resins

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2007/presentations/external/NVVT

Coating Resins on Bio-based Raw Materials

Reality or Distant Future?

Tosko Misev, Dirk Stanssens

DSM Resins bv, DSM Innovation Center

DSM Coating Resins

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• Since existence of human beings, people have always used paints to express themselves

• Early paints based on natural products were of inferior quality

• Non-natural products were introduced to improve properties• alkyds, acrylics, polyurethanes, polyesters, epoxies, amino resins

• Now we see a reverse movement• Oil reserves are limited and have a long cycle time (100 mln years)• Natural renewable resources are abundantly available with cycle time of 1 year• White biotechnology is developing with increasing speed

IntroductionIntroduction

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What is What is white (white (industrialindustrial)) biotechnology? biotechnology?

Marketpenetration

TimeToday

Industrial applications

BiofeedstockReplacement of fossil feedstock bysugar and biomass

BioprocessesUse of natures toolboxfor industrial processes(e.g., enzymes,bacteria)

BioproductsCurrent and new biobased products (e.g.,fuel, materials)

BioremediationUse of biologicalprocesses for environmental cleanup (e.g.,waste water, oil pests)

Pharma (red)

biotech

Ag (green)

biotech

WhiteBiotech

Source: McKinsey

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White (industrial) biotechnologyWhite (industrial) biotechnology

Fermentable sugars Specialties

Materials

Base chemicals

Fuel

FeedstockBioprocess

(cells / enzymes)Products

Biotechnology: The use of nature’s toolbox for industrial processes

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CAGR 9,1%

Year

Price

CAGR -3,4%

Crude oil price

Raw sugar price (*)

0%

50%

100%

150%

200%

250%

1994 95 96 97 98 99

2000 01 02 03 04

Over the last 10 years oil and sugar prices have followed quite opposite trends

Feedstock prices are expected to decrease further on with the conversion of wood and agricultural waste into fermentable sugar

Basic feedstock price developmentsBasic feedstock price developments

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Existing raw materials of petrochemical origin

Resin Raw Materials

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Polycondensation Resins

Mineral oil - Natural gas

Reformate

o,m,p-xylene

Phthalic acids

Propylene

Iso-or –n-butyraldehyde

Methanol

Formaldehyde

Neopentyl Glycol

Ethanol

Acetaldehyde

PentaerytritolTrimethylol Propane

Propylene

Glycerol

Polyesters Alkyds

500 kT 200 kT150 kT

Allyl Chloride

Epichlorohydrine

1800 kT

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Polymerization Resins

Mineral oil - Natural gas

Propylene

Acrolein

Acrylic acid

Acetone

Acetone cyanhydrine

HCN

Alcohols

Ethylbenzene

Styrene

Methanol

Vinyl acetate

Acrylics, Styrene/Acrylics and Vinyl Acetate Copolymers

Acetic acid

Acrylic esters

H2SO4

Benzene Ethylene

Methacrylic esters

3200 kT

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Upcoming bio-based building blocks

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Building Blocks Through White Biotechnology

Sugar crops

Oil crops

Biomass (straw, switchgrass)

Fermentation

Bio-catalysis

Bio-fuel

Biomaterials

Nutritional Ingredients

Specialty Chemicals

Commodity Chemicals

20 billion $

Pharma intermediates

Amino acids, Vitamins

Citric acid, Oleochemicals

Flavors, fragrances

Enzymes

1 billion $

Polylactic acid

Glycols

Ethylene

Acrylic acid

Biological Feedstock

Biotechnological

and/or

Conventional Processes

Industrial Products

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What can we count on ?

Sugars Vegetable oils

Polyols

Polyacids

Monomers

PolyestersAlkyd Resins

PolyurethanesEpoxy ResinsAcrylic resins

Polyols

Fatty Acids

PolyurethanesAlkyd ResinsPolyamides

Epoxy Esters

Biological Feedstock

Biotechnological

and/or

Conventional Processes

Sugar crops Oil crops

Basic raw materials

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What we already use

Vegetable oils:

Renewable

Non toxic

Biodegradable

Full environmental acceptance

Use: Alkyd resins

Glycerol:

Renewable

Non toxic

Biodegradable

Full environmental acceptance

Use: Alkyd resins, Polyesters

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What is already available in the market

Soyol™ “biobased” polyols: OH functionality: 2 – 3

Molecular weight: 1000-2000

Uses: • Seating foam furniture• Foam insulation• Carpet backing• Shoe soles

• Roof coatings.

Effects:• Cost less than the petroleum polyols they replace. • Plant based, annually renewable resources. • Reduce demand and dependence on limited petroleum reserves.

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What we can expect to come ?

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Succinic Acid: C4H6O4

One of the top 12 chemicals from biomass HOOH

O

O

Potential use:

• Diacid for polyesters• Diacid for alkyds• Intermediate for manufacturing of:

• Maleic acid (polyesters)• Butanediol (polyesters)• Diaminobutane (polyamides)• Adipic acid (polyesters, polyamides)

What we expect to come

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Interrelation between the most relevant 1,4-bifunctional C4 building blocks.

The reactions from left to right require reduction (so the reverse require oxidation), whereas the ring-closures are dehydratation reactions.

HOOC-CH=CH-COOH HOOC-CH2-CH2-COOH HOOC-CH2-CH2-CH2OH HOCH2-CH2-CH2-CH2OH

Fumaric/Maleicacid Succinicacid 4-Hydroxybutanoicacid 1,4-Butanediol

Maleicanhydride Succinicanhydride gamma-Butyrolactone Tetrahydrofuran

OO=O

OO= =O

OO= =O

HOOC-CH=CH-COOH HOOC-CH2-CH2-COOH HOOC-CH2-CH2-CH2OH HOCH2-CH2-CH2-CH2OH

Fumaric/Maleicacid Succinicacid 4-Hydroxybutanoicacid 1,4-Butanediol

Maleicanhydride Succinicanhydride gamma-Butyrolactone Tetrahydrofuran

OOO=O

OO=O

OO= =O

OOO= =O

OO= =O

OOO= =O

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Isosorbide: C6H10O4

Via dehydration of sorbitol

OH

OH

O

O

Difunctional polyol for: • Polyesters • Polycarbonates• Polyamides• Polyurethanes• Plasticizers

Commercial quantities: 2008/2009

Itaconic Acid: C5H6O4

Via fungal fermentation of glucose

HOOH

O

OCH2

Potential use:• Polymerization monomer• (Meth)acrylic esters alternative • Hydrogels for superabsorption

Commercial quantities: 2007

3-Hydroxy Propionic Acid: C3H6O2

Feedstock for:• Acrylonitrile • Acrylic Acid• Acrylamide

HO OH

O

Technically feasible, but not yet cost effective

What we expect to come

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Summary of existing and potential opportunities

Acids:

Fatty acids

Succinic acid

Maleic acid

Fumaric acid

Adipic acid

Polyols:

Glycerol

Sorbitol

Isosorbide

Butane diol

Monomers:

Itaconic acid & esters

Acrylic acid & esters

Acrylonitrile

Acrylamide

Polycondensation resins

Alkyd resins

Polyesters

Polyurethanes

Polymerization resins

Acrylic resins

Alternatives to acrylic resins

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Can the prices go even further down?Can the prices go even further down?

20 tons/acre?20 tons/acre? ( (www.bical.net)10-30 tons/acre10-30 tons/acre ( (www.aces.uiuc.edu/DSI/MASGC.pdf)

Energy crops: Miscanthus -1 years growth without replanting!

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Biomass Will Make a DifferenceBiomass Will Make a Difference

Turning South Dakota into… …a member of OPEC?!

Farm acres

Tons/acre

Gallons/ton

Thousand barrels/day

Today Tomorrow

44 Million

5

25

857

44 Million

15

80

3,429

Iraq

Kuwait

Libya

Nigeria

Thousand barrels/day

1,700

2,600

1,650

2,200

Qatar

Saudi Arabia

UAE

800

9,400

2,500

South Dakota 3,429

Iran 3,900

Venezuela 2,500

Algeria 1,380

Indonesia 925

Source: Ceres Company PresentationSource: Ceres Company Presentation

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Biomass Will Make a DifferenceBiomass Will Make a Difference

The chemical industry is working hard to use ligno-cellulose as a feedstock

• Ligno cellulose is much more available than e.g. crops.• A whole plant can be used.• Use of land not suitable for food or feed ( prairies-USA, pampas-Argentina) • No competition between making chemicals and supplying food.• Selection and\or genetically modified plants that grow very fast. • Environmentally friendly cultivation; plants that do not need fertilizers

The next step: bio-refinery

Switch-grass cultivation

Extraction of valuable products

(proteins)

Chemical building blocks

Rest for Bio-fuel

The biomass as a feedstock will further reduce the prices of the chemicals

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Conclusion

0

10

20

30

40

50

60

70

80

2001 2002 2003 2004 2005 2006

Sugars Vegetable oilsMineral Oil

0

0.1

0.2

0.3

0.4

0.5

0.6

2001 2002 2003 2004 2005 20060.54

0.56

0.58

0.6

0.62

0.64

0.66

0.68

0.7

2001 2002 2003 2004 2005 2006

USD/barrel USD/kg USD/kg

• Oil reserves are limited, not renewable. Oil price still volatile and has tripled in the past five years

• Sugars/vegetable oils: Costs decreased with a tendency to stabilize.

• Further progress in white biotechnology offers solutions based on even cheaper biomass feedstock

Coating Resins on Bio-based Raw Materials: Reality or Distant Future?

Not yet but will be soon

dsm coating resins 2007/presentations/external/nvvt 0 coating resins on bio-based raw materials...

Documents

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dirk stanssens dsm resins

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mckinsey slide

years oil

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