Dr. Suresh S. Narine Director, Alberta Bioplastics Network Professor, University of Alberta Industrial Uses of Vegetable Oils

Dr. Suresh S. NarineDirector, Alberta Bioplastics NetworkProfessor, University of Alberta

Industrial Uses of Vegetable Oils

Feedstock for the Chemical Industry

renewableresources

coal

fossil oil, gas

1850 1900 1950 2000 2050

year

Carbon-Carbon Bonds: The Carbon-Carbon Bonds: The heart of the matter.heart of the matter.

It is important to realize that the commodities It is important to realize that the commodities produced from “petro-products” derive their produced from “petro-products” derive their properties from Carbon-Carbon bonds:properties from Carbon-Carbon bonds:

– Nature provides these via photosynthesisNature provides these via photosynthesis

– Fossil Fuels are just reserves of photosyntheticFossil Fuels are just reserves of photosyntheticMaterial that have not been utilized.Material that have not been utilized.

– Why not find ways of making direct use of such bonds, Why not find ways of making direct use of such bonds, without having to wait the thousands of years for them to without having to wait the thousands of years for them to become oil or coal?become oil or coal?

World Biomass Production

Plants are a gigantic sun reactor.Of the daily energy from sun of 1.5 x 1022 J, only 4 x 1018 J (0.008%) are use to build up

biomass.Only approx 7% of the biomass is used by mankind.

7%utilized

93%unutilized

The build up biomass is about 1000 times bigger than the amount of plastics producedworld wide.The amount of paper produced world wide is about twice as big as the producedamount of plastics.

Polymers from Plants

200 bill. t

300 mio. t

8 mio. t

180 mio. t

0

1012

biomass paper starch plastics

1010

108

106

104

102

Crude oil vs. renewable Crude oil vs. renewable resourcesresources

productsMonomers

Cosmetics

lubricants

fumaric acid

itaconic acid

aconitic acid

succinic acid

2,3-butanediol

1,3-propanediol

crude oil

costs?

costs?

starch

sugar

renewable resources

Vegetable Oils

Bio-Based Materials Are Becoming Bio-Based Materials Are Becoming Increasingly ImportantIncreasingly Important

By the year 2010, Dupont will be sourcing 25% of its materials for By the year 2010, Dupont will be sourcing 25% of its materials for polymers and petrochemicals from renewable resources.polymers and petrochemicals from renewable resources.

*Sorona*SoronaTMTM - stretch fibre made from corn - Dupont - stretch fibre made from corn - Dupont

WoodstalkWoodstalkTMTM - wheat straw wood alternative - Dow BioProducts Ltd. - wheat straw wood alternative - Dow BioProducts Ltd.

NatureWorksNatureWorksTMTM - carpets, shirts, bottles, cups, films, etc. - Cargill - carpets, shirts, bottles, cups, films, etc. - Cargill Dow LLC Dow LLC

Milligan Diesel Fuel Conditioner - canola based - Milligan Bio-Tech Milligan Diesel Fuel Conditioner - canola based - Milligan Bio-Tech Inc. Inc.

Natural resins and Bio-Oils from wood wastes - Ensyn Technologies Natural resins and Bio-Oils from wood wastes - Ensyn Technologies Inc. Inc.

Archer RC* Non-volatile coalescing agent for latex paints - Archer Archer RC* Non-volatile coalescing agent for latex paints - Archer Daniels Midland Co. Daniels Midland Co.

The Chemical Factory Moves into the Plant

sunrainCO2

Annual Production of LipidsAnnual Production of Lipids

Average Annual Production of Oils

0

50

100

150

200

1976 - 1980 1996 -2000 2116 -2120

Years

MM

to

nn

es

Soybean

World Total

Palm

Canola/Sunflower

Other Veg. Oils

Animal Fats

Canadian ProductionCanadian Production

CanolaCanola

– Canada produces 20% of the world’s edible oil production, mostly as Canada produces 20% of the world’s edible oil production, mostly as Canola OilCanola Oil

– Saskatchewan produces 50% of Canada’s productionSaskatchewan produces 50% of Canada’s production

– Manitoba and Alberta produces equal amounts of the remaining 50%Manitoba and Alberta produces equal amounts of the remaining 50%

– Due to Soybean Oil production pressures from China and Brazil, Canola Due to Soybean Oil production pressures from China and Brazil, Canola Acreage in Western Canada is significantly below historical norms.Acreage in Western Canada is significantly below historical norms.

– The industry can easily produce an additional 4 Million Metric Tonnes, The industry can easily produce an additional 4 Million Metric Tonnes, with Alberta alone being able to produce 1.87 Million Metric Tonnes, with Alberta alone being able to produce 1.87 Million Metric Tonnes, based on historical production patterns within the last 10 years.based on historical production patterns within the last 10 years.

Canadian ProductionCanadian Production

Flaxseed is the first oilseed to be widely grown in Flaxseed is the first oilseed to be widely grown in Western CanadaWestern Canada

Only 20% of the area devoted to Canola is devoted to Only 20% of the area devoted to Canola is devoted to flax in Western Canada, with Saskatchewan and flax in Western Canada, with Saskatchewan and Manitoba being the major producers.Manitoba being the major producers.

Most of the flax grown here is for oil usage as opposed Most of the flax grown here is for oil usage as opposed to the European varieties, in which most of the flax to the European varieties, in which most of the flax grown is for fibre utility.grown is for fibre utility.

99% of the flax grown in Western Canada is for industrial 99% of the flax grown in Western Canada is for industrial use, although Flax is a major source of PUFA’s, edible use, although Flax is a major source of PUFA’s, edible use is limited, primarily due to the high reactivity of the use is limited, primarily due to the high reactivity of the oil with oxygen.oil with oxygen.

Major Industrial UsesMajor Industrial Uses

As Feedstock for Polymers As Feedstock for Polymers

Drying Oils in Paints and VarnishesDrying Oils in Paints and Varnishes

As lubricantsAs lubricants

As Feedstock for Specialty ChemicalsAs Feedstock for Specialty Chemicals

As BiodieselAs Biodiesel

As ingredients for cosmeticsAs ingredients for cosmetics

Marketing AdvantageMarketing Advantage

Average Relative Price (Range)Average Relative Price (Range)

– Petroleum base stock – LubesPetroleum base stock – Lubes 1 X / kg1 X / kg– Plant Oils Plant Oils 1 – 2 X / kg1 – 2 X / kg– Synthetic Base Stock – LubesSynthetic Base Stock – Lubes 3 – 8 3 – 8

X / kgX / kg

– Resins – CoatingsResins – Coatings :: 3 – 6 X / kg3 – 6 X / kg– BioBased Synthetic EstersBioBased Synthetic Esters 2 – 5 X / kg2 – 5 X / kg

Source: Dharma Kodali,Cargill Inc.

Source: Dharma Kodali,Cargill Inc.

Molecular Structure Determines Use.Molecular Structure Determines Use.

The applicability of vegetable oils to industrial The applicability of vegetable oils to industrial processes are dependent on the predominant processes are dependent on the predominant functional groups within the triacylglycerol functional groups within the triacylglycerol molecules of the oil.molecules of the oil.

These oils are composed of a glycerol These oils are composed of a glycerol backbone, to which are esterified three fatty acid backbone, to which are esterified three fatty acid molecules.molecules.

The chain lengths, degree of unsaturation, and The chain lengths, degree of unsaturation, and types of functional groups on the fatty acid types of functional groups on the fatty acid molecules determine the native properties and molecules determine the native properties and chemical possibilities of the oilchemical possibilities of the oil

Unsaturated Fatty Acids Present in Unsaturated Fatty Acids Present in Canada’s OilseedsCanada’s Oilseeds

Exotic Oils with Specialized Exotic Oils with Specialized Functionality on the Fatty AcidsFunctionality on the Fatty Acids

Properties / Functionality / Properties / Functionality / ValueValue

Applications,Functionalities

Markets

Value Creation

Physical Structure and

Properties

Chemical Structure andComposition

Property / Functionality / ValueProperty / Functionality / ValueMolecular PropertyMolecular Property– ReactivityReactivity– Iodine ValueIodine Value– Chain LengthsChain Lengths– ConjugationConjugation– Saponification ValueSaponification Value– Acidic ValueAcidic Value– Peroxide ValuePeroxide Value– PolarityPolarity– SolvencySolvency– HydrophobicityHydrophobicity– Molecular WeightMolecular Weight– Molecular PackingMolecular Packing– HeterogeneityHeterogeneity

Derived FunctionalityDerived Functionality– Appearance / ColourAppearance / Colour– Viscosity (flow properties)Viscosity (flow properties)– Volatility (VOC)Volatility (VOC)– Low Temperature BehaviorLow Temperature Behavior– Drying (film formation)Drying (film formation)– AdhesionAdhesion– Tack / Rub offTack / Rub off– LubricityLubricity– Oxidative Stability / Shelf Oxidative Stability / Shelf

LifeLife– CompatibilityCompatibility– BiodegradabilityBiodegradability

North American Plastics North American Plastics Production Strong GrowthProduction Strong Growth

0

10000

20000

30000

40000

50000

60000

70000

80000

1990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000

Mill

ions

of L

B

Polyethylene Polypropylene Other

Product Production IndexProduct Production Index

80

90

100

110

120

130

140

150

1990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000

Prod

uctio

n In

dex

92=1

00

Plastic Products Paper Products Steel and Mill

Source: Federal Reserve Board

Sources of PlasticsSources of Plastics

99.5% of current plastics are made from fossil 99.5% of current plastics are made from fossil fuel derivativesfuel derivatives

PolyethylenePolyethylenePolystyrenePolystyrene

Majority of such “Petro-Plastics” are non-Majority of such “Petro-Plastics” are non-biodegradable.biodegradable.

Some exceptions do exist, e.g. PolyCaprolactoneSome exceptions do exist, e.g. PolyCaprolactone

Petro-Plastics are produced at large energy Petro-Plastics are produced at large energy costs, due to the need for “cracking.”costs, due to the need for “cracking.”

Plastic ProductionPlastic Production

Approximately 180 Million tonnes of plastic produced Approximately 180 Million tonnes of plastic produced annuallyannually

It takes approximately 141 MJ/kg of energy to produce It takes approximately 141 MJ/kg of energy to produce Nylon, and 76 MJ/kg of energy to produce amorphous Nylon, and 76 MJ/kg of energy to produce amorphous PETPET

Therefore millions of tons of fossil fuel is required to first Therefore millions of tons of fossil fuel is required to first make the plastics, and then additional reserves are make the plastics, and then additional reserves are required to process them into useful items.required to process them into useful items.

Plastics production consumes 4% of the world’s supply Plastics production consumes 4% of the world’s supply of petroleum!of petroleum!

What are the Drivers Impacting What are the Drivers Impacting the Future Polymer Industrythe Future Polymer Industry

Finite Fossil Fuel SourcesFinite Fossil Fuel Sources

Environmental and health concerns.Environmental and health concerns.

Consumer attitudes.Consumer attitudes.

Cost of “cheap” feedstocks.Cost of “cheap” feedstocks.

Carbon CreditsCarbon Credits

Greenhouse Gas ReductionGreenhouse Gas Reduction

Criteria Air Contaminant ReductionCriteria Air Contaminant Reduction

A cluttered way forwardA cluttered way forwardRenewabilityRenewability

SustainabilitySustainability

Environmental ConcernsEnvironmental Concerns– BiodegradabilityBiodegradability– RecyclabilityRecyclability

Economic ContinuityEconomic Continuity

Product PerformanceProduct Performance

Etc.Etc.

MarketsMarkets

1997 1997 FiguresFigures

Projected Projected for 2004for 2004

RevenueRevenue US $23 MUS $23 M US $187 MUS $187 M

MassMass 20 M lbs20 M lbs 167 M lbs167 M lbs

Biodegradable Plastics: US + Japanese Mkts

MarketsMarkets

1997 1997 FiguresFigures

Projected Projected for 2004for 2004

RevenueRevenue US $16.32 US $16.32 MM

US $73.15 US $73.15 MM

MassMass 2, 3402, 340

tonnestonnes

24, 16024, 160

tonnestonnes

Biodegradable Plastics: European Mkts

N.A. Biodegradable Polymer MarketN.A. Biodegradable Polymer Market

2000 Figures

2005 Projection0

5

10

15

20

25

Mil

lion

s of

lbs

Packaging CompostBags

Agricultural Films,Hygiene-related products, paper Coatings, etc.

(35 M lbs)

(25 M lbs)

Major Barriers for Biodegradable PolymersMajor Barriers for Biodegradable PolymersLegislationLegislation

Landfill taxesLandfill taxes

Development of infrastructure to collect and process Development of infrastructure to collect and process biodegradable polymersbiodegradable polymers

Development of universal standards for biodegradability and Development of universal standards for biodegradability and compostabilitycompostability

Consumer attitude towards absorbing the costConsumer attitude towards absorbing the cost

Technological improvements to improve price differentiation.Technological improvements to improve price differentiation.

Drivers for Biodegradable PolymersDrivers for Biodegradable Polymers

Consumers becoming more environmentally Consumers becoming more environmentally consciousconscious

Prices of biodegradable polymers have Prices of biodegradable polymers have decreased significantlydecreased significantly

Technological advances which impact both price Technological advances which impact both price and performance are continually being and performance are continually being implemented.implemented.

Exotic Oils with Specialized Exotic Oils with Specialized Functionality on the Fatty AcidsFunctionality on the Fatty Acids

Vegetable Oils Vegetable Oils as Feedstock as Feedstock for Polymersfor Polymers

Biopolymer leads “naturally” to Biopolymer leads “naturally” to Biodegradable PlasticsBiodegradable Plastics

CanolaSoil

AgriculturalFeedstock

Processing

BiopolymerResins

PackageConverter

Fast FoodPackaging

RestaurantWaste

Composting

Humus

CO2

TremendousEconomic

DevelopmentActivity

The PetroChemical Industry can The PetroChemical Industry can only benefit from this trendonly benefit from this trend

The Kyoto issue is one that is not going to The Kyoto issue is one that is not going to disappear, regardless of what guise it disappear, regardless of what guise it takes here on forward.takes here on forward.

By partnering with the value-added By partnering with the value-added agricultural industry, technological agricultural industry, technological solutions which provide greater solutions which provide greater sustainability may be achieved.sustainability may be achieved.

Sources of Agricultural FeedstockSources of Agricultural FeedstockAgricultural Polyesters:Agricultural Polyesters:– Poly Hydroxy Alkanoates (bacterial, plant)Poly Hydroxy Alkanoates (bacterial, plant)– Poly Lactic Acid (fermented carbohydrates)Poly Lactic Acid (fermented carbohydrates)

Agricultural FibresAgricultural Fibres– Composites with “petro-plastics”Composites with “petro-plastics”– Crop and forestry fibresCrop and forestry fibres

Starch-based polymers Starch-based polymers – Corn, barley opportunities, etc.Corn, barley opportunities, etc.

Protein-based plasticsProtein-based plastics– Corn, elastin, collagen, spider silk, soy proteinsCorn, elastin, collagen, spider silk, soy proteins

Lignin-based plasticsLignin-based plasticsOilseed PlasticsOilseed Plastics

Two Major Avenues for producing Two Major Avenues for producing Agricultural FeedstockAgricultural Feedstock

Chemical Modification of existing agricultural Chemical Modification of existing agricultural commodities or waste: commodities or waste:

Chemical Synthesis in the case of oilseedsChemical Synthesis in the case of oilseedsFermentation in the case of Poly Lactic AcidFermentation in the case of Poly Lactic Acid

Bio-engineering of current or new crops to Bio-engineering of current or new crops to harvest molecules directly from the plant:harvest molecules directly from the plant:

Genetic modification of plants like Canola to produce PHAGenetic modification of plants like Canola to produce PHAGenetic modification of plants like Canola to produce Genetic modification of plants like Canola to produce Ricinoleic Acid Ricinoleic Acid

Barriers to Bio-EngineeringBarriers to Bio-Engineering

RegulationsRegulations

Cross-Contamination Issues – difficult to Cross-Contamination Issues – difficult to imagine agricultural acreage being devoted to imagine agricultural acreage being devoted to this in the short term.this in the short term.

Science is long term (only 14% of PHA has been Science is long term (only 14% of PHA has been engineered into Arabidopsis, and Monsanto engineered into Arabidopsis, and Monsanto through its Biopol operations, dumped this through its Biopol operations, dumped this initiative). initiative).

Drivers for Bio-EngineeringDrivers for Bio-Engineering

Can produce homogenous feedstockCan produce homogenous feedstock

Can remove the need for excessive processing Can remove the need for excessive processing stepssteps

Can allow food crops to continue to deliver their Can allow food crops to continue to deliver their main food product, whilst allowing leaves and main food product, whilst allowing leaves and other plant parts to deliver plastic molecules.other plant parts to deliver plastic molecules.

Barriers to Chemical Barriers to Chemical SynthesisSynthesis

Carbon and energy balances of the life-cycle of Carbon and energy balances of the life-cycle of such products are difficult to calculate.such products are difficult to calculate.

CostCost

PerformancePerformance

Solvent-dependent ProcessesSolvent-dependent Processes

Drivers for Chemical Drivers for Chemical SynthesisSynthesis

Can be achieved in the short-termCan be achieved in the short-term

Can address issues of Can address issues of renewability renewability in the short term, in the short term, and and biodegradability biodegradability in the long term. in the long term.

Does not depend on regulations or agricultural acreage.Does not depend on regulations or agricultural acreage.

By careful use of materials science and fractionation By careful use of materials science and fractionation techniques, can deliver homogenous feedstocktechniques, can deliver homogenous feedstockProvides a roadmap for bio-engineers – what Provides a roadmap for bio-engineers – what molecules are worth growing in plants.molecules are worth growing in plants.

How can we connect the How can we connect the plastics markets, through plastics markets, through

research, with Canola research, with Canola production?production?

Centered at the University of Centered at the University of Alberta is a Major Initiative to Alberta is a Major Initiative to provide synthetic solutions to provide synthetic solutions to

this problem this problem

The Alberta Bioplastics NetworkThe Alberta Bioplastics Network

Multi-institutional initiative to build a BioPlastics Multi-institutional initiative to build a BioPlastics Industry in Alberta.Industry in Alberta.

University of Alberta (UofA)University of Alberta (UofA)

Alberta Agriculture, Food and Rural Development (AAFRD)Alberta Agriculture, Food and Rural Development (AAFRD)

Alberta Research Council (ARC)Alberta Research Council (ARC)

Environment Canada (EC)Environment Canada (EC)

Agriculture and Agrifood Canada (AAFC)Agriculture and Agrifood Canada (AAFC)

Alberta Economic Development (AED)Alberta Economic Development (AED)

The Alberta Bioplastics NetworkThe Alberta Bioplastics Network

Activity is on four broad nodes:Activity is on four broad nodes:

Fundamental ScienceFundamental ScienceMaterials Science, BiotechnologyMaterials Science, BiotechnologyUniversity of Alberta, Alberta Research Council, Agriculture and University of Alberta, Alberta Research Council, Agriculture and Food Labs (AAFRD)Food Labs (AAFRD)

Scale Up TechnologiesScale Up TechnologiesCentre for Agri-Industrial Technology (AAFRD)Centre for Agri-Industrial Technology (AAFRD)Alberta Research CouncilAlberta Research Council

Marketing and Investment AnalysisMarketing and Investment AnalysisAAFRDAAFRDAEDAEDAAFCAAFC

The ObjectivesThe Objectives

To develop a bio-polymer industry within Alberta To develop a bio-polymer industry within Alberta based on canola and flaxseed oils.based on canola and flaxseed oils.

ElementsElements::

1.1. Develop synthesis reactions to render canola Develop synthesis reactions to render canola and flaxseed oils into polymersand flaxseed oils into polymers

2.2. Investigate relationships between processing Investigate relationships between processing conditions, polymer structure, physical and conditions, polymer structure, physical and chemical properties.chemical properties.

The Objectives (con’t)The Objectives (con’t)

3.3. Scale up processes that are economic and Scale up processes that are economic and technically feasible.technically feasible.

4.4. Investigate and develop investment opportunities.Investigate and develop investment opportunities.

5.5. Evaluate comparative environmental and energy Evaluate comparative environmental and energy costs.costs.

6.6. Develop effective knowledge and technical Develop effective knowledge and technical transfer processes.transfer processes.

Technology UpdateTechnology Update

We have produced plastics from Canola Oil We have produced plastics from Canola Oil which:which:– Are suitable for automobile panels, and moulded Are suitable for automobile panels, and moulded

automobile parts such as bumpers and dashboards.automobile parts such as bumpers and dashboards.– Are suitable for medical tubing, catheter bags, etc.Are suitable for medical tubing, catheter bags, etc.– Are suitable for insulation, rust-coatings, and Are suitable for insulation, rust-coatings, and

protective coatings.protective coatings.– Are suitable for moulded food packaging as well as Are suitable for moulded food packaging as well as

packaging film.packaging film.– Etc.Etc.– Etc.Etc.

Technology UpdateTechnology Update

We also produce a number of very valuable by-We also produce a number of very valuable by-products, such as 1,3 propanediol.products, such as 1,3 propanediol.

We are currently commissioning a pilot plant in We are currently commissioning a pilot plant in Alberta to produce large quantities of our Alberta to produce large quantities of our monomers, for large scale testing on automobile monomers, for large scale testing on automobile components.components.

We expect to have a commercial plant in Alberta We expect to have a commercial plant in Alberta within three years.within three years.

Vegetable Oils as Drying OilsVegetable Oils as Drying OilsDrying Oils: Drying Oils: Flaxseed and Tung Flaxseed and Tung

– Iodine Value greater than or equal to 150Iodine Value greater than or equal to 150– Applications are in paints, resins, coatings, inks.Applications are in paints, resins, coatings, inks.

Semi-Drying Oils: Soybean, Sunflower, Semi-Drying Oils: Soybean, Sunflower, CanolaCanola

– Iodine Value between 110 and 150Iodine Value between 110 and 150– Applications in term of drying are limited, although with Applications in term of drying are limited, although with

the use of some cationic catalysts, soybean oil has been the use of some cationic catalysts, soybean oil has been used as a drying oilused as a drying oil

Non-Drying Oils: Palm Oil, Coconut Oil, Non-Drying Oils: Palm Oil, Coconut Oil, Olive OilOlive Oil

– Iodine Value less than or equal to 100Iodine Value less than or equal to 100– Applications are as lubricants, heat transfer fluids, etc., Applications are as lubricants, heat transfer fluids, etc.,

i.e. application which absolutely must resist oxidative i.e. application which absolutely must resist oxidative reactions.reactions.

Drying Drying Process Process

==Polymerization Polymerization

ProcessProcess

Rate of Oxidation of Fatty Acids Rate of Oxidation of Fatty Acids Found in Canadian OilseedsFound in Canadian Oilseeds

University of Alberta ActivitiesUniversity of Alberta Activities

We have used catalysts to develop faster rates We have used catalysts to develop faster rates of drying for Canola Oil.of drying for Canola Oil.

This can lead to the use of Canola oil as a This can lead to the use of Canola oil as a source of biodegradable agricultural film.source of biodegradable agricultural film.

This can also lead to the use of Canola oil as a This can also lead to the use of Canola oil as a drying oil in paints and varnishes, much like the drying oil in paints and varnishes, much like the way in which linseed oil is currently used.way in which linseed oil is currently used.

Vegetable Oils as LubricantsVegetable Oils as Lubricants

AdvantagesAdvantages– Excellent boundary lubricationExcellent boundary lubrication– Good viscosity and viscosity indexGood viscosity and viscosity index– High Flash PointHigh Flash Point– Biodegradable, non-toxicBiodegradable, non-toxic– Environmentally Friendly, RenewableEnvironmentally Friendly, Renewable

DisadvantagesDisadvantages– Poor Oxidative StabilityPoor Oxidative Stability– Poor Low Temperature PropertiesPoor Low Temperature Properties– Lack of a good dynamic viscosity rangeLack of a good dynamic viscosity range– Limited additive technologyLimited additive technology

Bio-LubricantsBio-LubricantsInterest in the use of bio-lubricants has developed in part Interest in the use of bio-lubricants has developed in part due to concerns about sustainability of mineral oils and due to concerns about sustainability of mineral oils and for other environmental-related issues.for other environmental-related issues.

Europe is at the forefront of development of the global Europe is at the forefront of development of the global biolubricant market.biolubricant market.

In 1999, the European market volume for biolubricants In 1999, the European market volume for biolubricants was estimated at 102 000 tonnes or roughly 1.9 % of the was estimated at 102 000 tonnes or roughly 1.9 % of the total European market for lubricants.total European market for lubricants.

The market value of this was estimated to be $231 M The market value of this was estimated to be $231 M (U.S.) – source, Frost and Sullivan, 2000.(U.S.) – source, Frost and Sullivan, 2000.

SectorsSectorsBy revenue, the hydraulic fluid market accounts for 2/3 of By revenue, the hydraulic fluid market accounts for 2/3 of the European marketthe European market

Chainsaw oils are the second largest category by Chainsaw oils are the second largest category by revenue, at 14%revenue, at 14%

Short-term forecasts sugest continued growth in the Short-term forecasts sugest continued growth in the share of the hydraulic oil market with other products share of the hydraulic oil market with other products remaining flat or showing a decline.remaining flat or showing a decline.

It is important to note that biolubricant markets in It is important to note that biolubricant markets in Germany, Scandinavia and Alpine Europe resulted from Germany, Scandinavia and Alpine Europe resulted from regulations stemming from environmental concerns of regulations stemming from environmental concerns of persistent toxicity of mineral oil lubricants.persistent toxicity of mineral oil lubricants.

SourcesSources

The sources of biolubricants are primarily from The sources of biolubricants are primarily from canola and rapeseed, with some amount of flax canola and rapeseed, with some amount of flax also being used.also being used.

Fuchs Petrolub in Mannheim, Germany, is the Fuchs Petrolub in Mannheim, Germany, is the world’s leader in biolubricants from Canola.world’s leader in biolubricants from Canola.

They employ a variety of chemical modification They employ a variety of chemical modification methods to increase the performance of the methods to increase the performance of the lubricants.lubricants.

United StatesUnited States

Vegetable oil based lubricants are a very small Vegetable oil based lubricants are a very small part of the U.S. lubricant market- less than one part of the U.S. lubricant market- less than one percent.percent.

Canola oil is the main feedstock, accounting for Canola oil is the main feedstock, accounting for 85% of the market, with Soybean and Flax oils 85% of the market, with Soybean and Flax oils making up the balance.making up the balance.

Driving the U.S. markets is an oversupply of Driving the U.S. markets is an oversupply of vegetable oils and a slightly higher price vegetable oils and a slightly higher price advantage from edible markets.advantage from edible markets.

U.S. PlayersU.S. Players

Mobil and Pennzoil both offer vegetable oil based Mobil and Pennzoil both offer vegetable oil based hydraulic fluidshydraulic fluidsThe market is approximately 1 M gallons, approximately The market is approximately 1 M gallons, approximately 0.4% of the total U.S. hydraulic market.0.4% of the total U.S. hydraulic market.Crankcase oils in the U.S. are a $2 B market.Crankcase oils in the U.S. are a $2 B market.An estimated 0.5% of this is vegetable oil based.An estimated 0.5% of this is vegetable oil based.

However, major growth is predicted in this area as the However, major growth is predicted in this area as the cost of petroleum goes up, and issues such as health cost of petroleum goes up, and issues such as health (trans, saturates) and production results in an over (trans, saturates) and production results in an over supply of vegetable oils.supply of vegetable oils.

Modified Oils for LubricantsModified Oils for Lubricants





We are well-equipped to chemically We are well-equipped to chemically convert, modify, and test lubricant convert, modify, and test lubricant applications of vegetable oil derivativesapplications of vegetable oil derivatives

Due to our oilseed lipid focus, we are able Due to our oilseed lipid focus, we are able to assess a variety of oilseed sourced by-to assess a variety of oilseed sourced by-products for their suitability as lubricants.products for their suitability as lubricants.

Vegetable Oils as a Source for Vegetable Oils as a Source for Specialty ChemicalsSpecialty Chemicals

Starting materialsStarting materialspolyolspolyols

1,3-propanediol

1,4-butanediol

glycerol

2,3-butanediol

OHHO

HO OH

OH

HOOH

HO OH

Possible products of 1,3-Possible products of 1,3-propanediolpropanediol

applications...applications...

Co-monomers in PTT (= Co-monomers in PTT (= polytrimethyleneterephthalate)polytrimethyleneterephthalate)

– base for carpets (Corterrabase for carpets (Corterra®®))– Special-textile fibers (SoronaSpecial-textile fibers (Sorona®®))

Co-monomer in polyestersCo-monomer in polyesters– binders, adhesives and sealants in industry binders, adhesives and sealants in industry

and housebuilding, lacquers, casting resinsand housebuilding, lacquers, casting resins

TwoTwo ways to 1,3-propanediol ways to 1,3-propanediol from Renewable Resourcesfrom Renewable Resources

??starch

sugar1,3-propanediol

GE(genetic engineering)

Clostridiumbutyricum

glycerol from rapeseed

1,3-Propanediol-fermentation1,3-Propanediol-fermentationwhich microorganism?which microorganism?

sensitive against oxygen-difficult handling

but... low risk class (R1/L1) ~ 0.50 kg PD per kg Glycerol

no oxygen problems - robust organism

but... potential pathogen (R2/L2) ~ 0.40 kg PD per kg Glycerol

Clostridium butyricum Klebsiella pneumoniae,Citrobacter freundii

use of Clostridium butyricumis preferable!

Cost comparison for chemical Cost comparison for chemical and biotechnical processesand biotechnical processes

ChemSystems, BIOTICA study March 99data basis 1997 USA

very low prices for raw material if glycerol water is used

crude oil price for 1997approx. 18 to 19 US$ per barrel (annual average)

0

1000

2000

3000

Rohstoffe (1997) Energiekosten direkte Fixkosten sonstige Fixkosten Abschreibung 20 % ROI

US$ for1 mt

of 1,3-PD

Shell Degussa DuPont ?ethylene oxide acroleine glucose glycerol 60,000 mt/a 45,000 mt/a 25,000 mt/a 25,000 mt/a

0.51 Europer kg

chemical biotechnical

0.26 Europer kg

0.13 Europer kg

0.21 Europer kg

raw material (1997)energy costsdirect fixed costsallocated fixed costsdepreciationprice for 20 % ROI

University of Albertaprocess for producingPDO as a by-product

Bio-Based SolventsBio-Based Solvents

Bio-Based SolventsBio-Based Solvents

Pressure to eliminate widely used solvents such Pressure to eliminate widely used solvents such as:as:

– Chlorinated HydrocarbonsChlorinated Hydrocarbons

– Methyl Ethyl HydrocarbonsMethyl Ethyl Hydrocarbons

– Methyl Ethyl KetonesMethyl Ethyl Ketones

is immense, due to their deleterious effects on is immense, due to their deleterious effects on the environment and health.the environment and health.

This provides market entrance advantages to This provides market entrance advantages to bio-based, biodegradable solvents.bio-based, biodegradable solvents.

AqueousCleaners

Semi-aqueousCleaners

AlternativeSolvents Total

0

50

100

150

200

250

300

Potential U.S. Market for Biobased Solvents

BiobasedReplacementMarket ($M/yr)

Current SolventMarket ($M/yr)

SOURCE: Technical Insights Alert, SEPTEMBER 06, 2002, Frost and Sullivan

Target AreasTarget Areas

The big markets which are most likely to be The big markets which are most likely to be replaced by bio-based solvents are:replaced by bio-based solvents are:

– Industrial CleanersIndustrial Cleaners– Carrier solvents for adhesives and coatingsCarrier solvents for adhesives and coatings

It is estimated (It is estimated (Industrial Bioprocessing, 2002) Industrial Bioprocessing, 2002) that between 2005 and 2010, biobased solvents that between 2005 and 2010, biobased solvents will replace 50% of the solvents currently used in will replace 50% of the solvents currently used in these applications.these applications.

Current PlayersCurrent Players

Polystyrene foam is widely used in packaging, Polystyrene foam is widely used in packaging, containers, household wares, boats, water coolers, and containers, household wares, boats, water coolers, and a variety of other uses. a variety of other uses.

Polystyrene does not readily degrade and generally Polystyrene does not readily degrade and generally cannot be reused. cannot be reused.

Researchers at the University of Missouri-Rolla have Researchers at the University of Missouri-Rolla have developed a use for soy and vegetable oil fatty acid developed a use for soy and vegetable oil fatty acid methyl esters in dissolving polystyrene foam, so that it methyl esters in dissolving polystyrene foam, so that it can be more usable in other resins, and coatings such can be more usable in other resins, and coatings such as fiberglass.as fiberglass.


Ethyl lactateEthyl lactate is currently produced in the is currently produced in the US by ADM and marketed by Vertec US by ADM and marketed by Vertec BioSolvents Inc. Current bulk market price BioSolvents Inc. Current bulk market price is about $1/lb. It is sold as a cleaner for is about $1/lb. It is sold as a cleaner for industrial inks, a degreaser for motors and industrial inks, a degreaser for motors and other machinery, and a number of other other machinery, and a number of other uses. uses.


D-LimoneneD-Limonene is a well-established commercial is a well-established commercial product. Current annual usage in the US is product. Current annual usage in the US is about 50 million lb. It has been down as low as about 50 million lb. It has been down as low as $0.25/lb. $0.25/lb.

It is a nonpolar solvent and so it does not mix It is a nonpolar solvent and so it does not mix with water. It has many uses, but the most with water. It has many uses, but the most important has been in cleaning products, both important has been in cleaning products, both industrial and household/institutional industrial and household/institutional preparations. It can replace a wide variety of preparations. It can replace a wide variety of organic solvents. organic solvents.

Current PlayersCurrent PlayersMethyl soyateMethyl soyate is the cheapest bio-based solvent, now is the cheapest bio-based solvent, now selling for about $0.40/lb in bulk. In addition to its selling for about $0.40/lb in bulk. In addition to its industrial uses, it has a big potential market as biodiesel industrial uses, it has a big potential market as biodiesel fuel. It is produced by transesterification of methanol and fuel. It is produced by transesterification of methanol and soybean oil, using sodium hydroxide as a catalyst and soybean oil, using sodium hydroxide as a catalyst and generating glycerol as a byproduct. Nine companies generating glycerol as a byproduct. Nine companies manufacture it in the United States. manufacture it in the United States.

it is not miscible with water, although it can be it is not miscible with water, although it can be formulated into water-miscible cleaners not only with formulated into water-miscible cleaners not only with ethyl lactate but with detergents. It is readily ethyl lactate but with detergents. It is readily biodegradable and has low toxicity and a high flash biodegradable and has low toxicity and a high flash point. It generates lower levels of volatile organic point. It generates lower levels of volatile organic compounds (VOCs), which is a plus for reducing air compounds (VOCs), which is a plus for reducing air pollution. pollution.

Edible SolventsEdible Solvents

As mounting pressures are brought to As mounting pressures are brought to bear on the edible oil industry in terms of bear on the edible oil industry in terms of trans fatty acid content and saturate trans fatty acid content and saturate content, biotechnology and innovative content, biotechnology and innovative processing will be required to play processing will be required to play increasing roles.increasing roles.

Edible solvents for fractionation and Edible solvents for fractionation and chromatographic application will become chromatographic application will become of maximum importance.of maximum importance.


We are developing synthetic methods on canola, and We are developing synthetic methods on canola, and flax as well as tall oil to create solvents competitive with flax as well as tall oil to create solvents competitive with methyl soyate.methyl soyate.

In particular, we have been using the waste streams In particular, we have been using the waste streams from Canola, Flax processing as a source of cheaper from Canola, Flax processing as a source of cheaper raw materials.raw materials.

We are also experimenting with edible bio-based We are also experimenting with edible bio-based solvents specifically for the solvent-fraction of edible oils.solvents specifically for the solvent-fraction of edible oils.

We have developed considerable expertise around the We have developed considerable expertise around the use of edible solvents for novel chromatographic use of edible solvents for novel chromatographic separations of edible oils.separations of edible oils.

Making Biodiesel is SimpleMaking Biodiesel is Simple

BiodieselBiodiesel

This is a common This is a common sign in Germanysign in Germany

Biodiesel is not only Biodiesel is not only readily available, it is readily available, it is cheaper than cheaper than Petroleum Diesel Petroleum Diesel because of the high because of the high taxes levied against taxes levied against Petroleum Products.Petroleum Products.

Personal Care and CosmeticsPersonal Care and CosmeticsGlobal Sales of cosmetics and toiletries (C&T) Global Sales of cosmetics and toiletries (C&T) reached $100 Billion in 2000 and is projected to reached $100 Billion in 2000 and is projected to increase to $120 Billion by 2005.increase to $120 Billion by 2005.

The U.S. dominates worldwide C&T markets at The U.S. dominates worldwide C&T markets at $25 Billion, followed by Europe and Japan.$25 Billion, followed by Europe and Japan.

The U.S. market for specialty chemicals used in The U.S. market for specialty chemicals used in finished C & T products was approximately $4 finished C & T products was approximately $4 Billion in 2000, and is projected to grow at a rate Billion in 2000, and is projected to grow at a rate higher than finished product projections.higher than finished product projections.

Top 10 U.S. Companies in household Top 10 U.S. Companies in household and personal products Industryand personal products Industry

0

5

10

15

20

25

Proctorand

Gamble

ColgatePalmolive

EsteeLauder

SCJohnson

Avon JohnsonDiversey

Clorox AlbertoCulver

Ecolab LimitedBrands

Bill

ion

s o

f D

olla

rs

OpportunitiesOpportunities

Natural, plant derived ingredients are most Natural, plant derived ingredients are most popular with consumers, with innovations popular with consumers, with innovations in extraction, processing, and chemical in extraction, processing, and chemical modifications expected to drive growth in modifications expected to drive growth in this area.this area.

Of particular importance to the lipids Of particular importance to the lipids industry are fatty acids and derivatives, industry are fatty acids and derivatives, alpha hydroxy acids, wax-replacements, alpha hydroxy acids, wax-replacements, gel replacements, and glycerol-based gel replacements, and glycerol-based compoundscompounds

Current EntrantsCurrent Entrants

ADM and Cargill are both very active in this ADM and Cargill are both very active in this area, using SOY as a source:area, using SOY as a source:– Petrolatums and waxesPetrolatums and waxes– Vegetable hard fats for aromatherapy candlesVegetable hard fats for aromatherapy candles– Paraffin-replacements in the packaging industryParaffin-replacements in the packaging industry– Waxes as replacements for beeswax and carnauba Waxes as replacements for beeswax and carnauba

wax in cosmeticswax in cosmetics– Replacement of castor oil by modified soybean oil in Replacement of castor oil by modified soybean oil in

cosmetics.cosmetics.


We have developed both soy based and canola based We have developed both soy based and canola based paraffin-replacement waxes.paraffin-replacement waxes.

We have developed a number of unique oil-sourced We have developed a number of unique oil-sourced chemicals ideal for emulsifiers in cosmetic applicationschemicals ideal for emulsifiers in cosmetic applications

We have developed methods to modify canola and flax We have developed methods to modify canola and flax oils to replace castor oil in cosmetic applicationsoils to replace castor oil in cosmetic applications

ConclusionsConclusions

The North American markets for edible oils is not The North American markets for edible oils is not increasing sufficiently to allow for significant growth in increasing sufficiently to allow for significant growth in acreage of canola.acreage of canola.

Canola acreage is significantly below historical norms in Canola acreage is significantly below historical norms in Western Canada.Western Canada.

By taking advantage of technological advances, we can By taking advantage of technological advances, we can access industrial markets, and by protecting our ability to access industrial markets, and by protecting our ability to supply these markets, we can command a premium supply these markets, we can command a premium price for canola and increase acreage.price for canola and increase acreage.

The environmental benefits are obvious and imperative.The environmental benefits are obvious and imperative.

AcknowldegementsAcknowldegements

Ed Phillipchuk, Connie Phillips, AAFRD Ed Phillipchuk, Connie Phillips, AAFRD Processing Division, CAITProcessing Division, CAITDonna Day, ARCDonna Day, ARCEd Condrotte, AEDEd Condrotte, AEDNarine Gurprasad, ENV. CAN.Narine Gurprasad, ENV. CAN.Brenda McIntyre, AAFCBrenda McIntyre, AAFCPeter Sporns, Phillip Choi, Xiahua Kong, Rysard Peter Sporns, Phillip Choi, Xiahua Kong, Rysard Nowak, Andrew Heberling, Marc Boodhoo, UofANowak, Andrew Heberling, Marc Boodhoo, UofADharma Kodali, CargillDharma Kodali, CargillAVAC, NSERC, ACIDF, AARI, ACPC, Bunge AVAC, NSERC, ACIDF, AARI, ACPC, Bunge Foods, ADM, Canbra Foods.Foods, ADM, Canbra Foods.

Documents

Dr. Suresh S. Narine Director, Alberta Bioplastics Network Professor, University of Alberta Industrial Uses of Vegetable Oils