Non-food uses: Opportunities for the Australian oilseed industry. Phil Salisbury & Allan Green

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1 Non-food uses: Opportunities for the Australian oilseed industry Phil Salisbury & Allan Green

2 The petrochemical factory Unlocking ancient carbon (non-renewable)

3 AOF Innovations ommittee Report: Industrial Use of Vegetable Oils Report evaluates: urrent and future uses of edible vegetable oils for industrial purposes, either directly or after fractionation urrent use of existing industrial (non-edible) vegetable oils The further domestication of existing wild species that produce industrial oils The development of novel industrial oils, using gene technology to breed new fatty acid compositions in existing, high yielding oilseed species

4 Industrial Use of Vegetable Oils Vegetable oils can be directly used for industrial purposes or can be split into different derivatives then utilized Oleochemicals refer to chemicals derived from natural oils and fats of both plant and animal origins Essentially, they refer to the fatty acids and glycerol derived from splitting of the triglyceride structure of oils and fats. They also include those derivatives derived from the subsequent modification of the carboxylic acid group of the fatty acid by chemical or biological means and further derivatives

5 Industrial Use of Vegetable Oils Oleochemicals are often categorized into basic groups including: fatty acids fatty acid methyl esters fatty alcohols fatty amines glycerol other compounds derived from further chemical modification of these groups

6 Direct industrial use of edible vegetable oils Direct industrial uses of edible vegetable oils include use as surfactants and adjuvants, drying agents and surface coatings, lubricants, dust suppressants, cosmetics, industrial raw materials specialty chemicals adhesives biocomposites

7 Direct industrial use of edible vegetable oils Direct use of vegetable oils in many industrial products is limited by: the restricted carbon chain length variation in the major cultivated oilseed species (mostly 16 18) and the lack of very high levels (>80%) of individual fatty acids in the major vegetable oils An exception to this general trend is the high oleic acid oils (75-85% oleic acid) developed in sunflower, canola and other oilseed species. HO oils have significant industrial application in lubricants, plastics and cosmetics. Further processing into oleochemicals is generally required to enable current vegetable oil products to be more efficiently utilized in industrial products

8 Use as oleochemicals Total oleochemical production Europe Asia America Others Oleochemical kt)

9 Use as oleochemicals World oleochemical production Fatty acids Fatty alcohols natural Glycerol natural Fatty Methyl Esters Fatty amines Basic oleochemicals Oleochemical (kt)

10 Use of existing industrial (non-edible) vegetable oils High Erucic Acid Rapeseed HEAR typically contain 50-60% erucic acid. In 2000, around 90,000t of HEAR seed was harvested across France, Germany, UK and Italy. Australia has also grown small commercial areas (1-3,000 ha) of HEAR in recent years using locally developed and adapted cultivars, but markets for the seed have not been readily available. HEAR oil has special properties including high smoke and flash points, oiliness and stability at high temperatures, ability to remain fluid at low temperatures and durability The principal end use is erucamide, a slip agent used in injection moulded plastics and polythene manufacture as an industrial lubricant, reducing surface tension and preventing adhesion between film surfaces HEAR oil is also used in printing inks, lubricants and a range of other applications

11 Use of existing industrial (non-edible) vegetable oils rambe rambe abyssinica has reached commercial status in North America where it grown for its erucic acid for industrial purposes In the UK it has also reached commercial status on a small scale, with several thousand hectares of production In Australia, rambe has yielded well (>1t/ha) in Mallee type environments ommercial adoption limited by high glucosinolate meal

12 Use of existing industrial (non-edible) vegetable oils Linseed Linseed (Linum usitatissimum) is grown worldwide as a source of oil for industrial use in the manufacture of paints, varnishes, resins, inks and linoleum, because of its drying and hardening properties when exposed to air and sunlight. World production of linseed is currently around 1 million tonnes. A few thousand hectares of linseed are grown in Australia annually, but much of this is used in bakery applications.

13 Domestication of wild industrial oil species One limitation to the use of current vegetable oils as oleochemicals is that most oils predominantly consist of 16 and 18 fatty acids. This restricts their use as oleochemicals. Many industrial products require shorter or longer chain fatty acids and often more complex fatty acids (e.g. with functional groups). This has led to investigations of less domesticated plant species as potential sources of these required shorter chain, longer chain & functionalised fatty acids. Among the fatty acids that have been identified are: unusual chain lengths hydroxy-, epoxy-, acetylenic-, conjugated fatty acids with double bonds at unusual positions.

14 Some unusual industrial fatty acids erucic acid (polymers, cosmetics, inks, pharmaceuticals) ricinoleic acid (lubricants, cosmetics pharmaceuticals) vernolic acid (resins, coatings, plasticisers) lauric acid (detergents) conjugated fatty acids (superior drying oils) petroselenic acid (polymers, detergents)

15 Domestication of wild industrial oil species Exploitation of these new sources requires either: the domestication of these wild species OR genetic engineering to transfer these traits into already adapted crop species

16 Domestication of wild industrial oil species Advantages Reduced reliance on traditional crops/products Extended range of crop options for farmers Reduced genetic vulnerability through diversification

17 Domestication of wild industrial oil species Disadvantages Undomesticated or wild species can have a number of agronomic problems which need to be addressed, including : low yield bienniality/perenniality very long flowering period pod shattering harvesting difficulty associated with poor plant type/architecture toxins

18 Indicative oil yields (t/ha) of traditional and potential new oilseed crops Sunflower 1.7 Rapeseed 1.3 Linseed 1.0 rambe 0.9 Euphorbia 0.7 alendula 0.4 Lunaria Lesquerella Limnanthes Dimorphotheca Premium prices obtainable for specialty oils are insufficient to offset current low oil yields of most candidate new crops

19 Domestication of wild industrial oil species Disadvantages Often a lack of understanding of breeding systems, phenology and areas of adaptation e.g. jojoba Long term breeding programs (20+ years) can be required to domesticate new crops. Need long term funding Success is dependent on being able to identify (or create) the required genetic variation

20 New industrial oils in existing oil crops This strategy involves extending the range of useful oils in existing high yield oil crops using gene transfer technologies Four major oil crops account for almost three-quarters of globally traded vegetable oils: soybean oil palm rapeseed sunflower It is an attractive option to use the recently developed GMO technology to manipulate these dominant oil crops so that they produce an enhanced range of valuable products

21 Where to in Australia? Need to identify (higher value) product areas where Australia is competitive or could develop a competitive advantage: urrent and future uses of edible vegetable oils for industrial purposes, either directly or after fractionation - NO urrent use of existing industrial (non-edible) vegetable oils - NO The further domestication of existing wild species that produce industrial oils SOME NEW ROPS WORK WORTHWHILE, PROVIDED LONG TERM FUNDING AVAILABLE The development of novel industrial oils, using gene technology to breed new industrial oil compositions in existing, high yielding oilseed species AUSTRALIA WELL PLAED WITH SEVERAL POTENTIAL PATENT POSITIONS

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23 rop Biofactories Initiative Strategic alliance between SIRO and GRD Plant Industry, Entomology, Molecular & Health Technologies ollaboration between materials scientists and biotechnologists to focus on future materials that could be made from future plants Focus areas Industrial Oils omplex Monomers Protein Biopolymers Three stages Stage 1 from 04/05 to 07/08 ($13M co-investment) Stage 2 & Stage 3 conditional on outcomes of Stage 1 Expected time of up to 10 years until commercialisation

24 rop Biofactories Initiative SIRO~GRD~RIRD national survey of expertise & interest in building an Australian biotransformation industry (2002) International Workshop on Biotransformation (2002) held to explore Australia s competitive niche advanced agriculture and downstream processing capability diversity of crops and growing seasons strong R&D capacity in biotechnology and materials science sound regulatory infrastructure

25 rop Biofactories Initiative SIRO~GRD~RIRD national survey of expertise & interest in building an Australian biotransformation industry (2002) International Workshop on Biotransformation (2002) held to explore Australia s competitive niche advanced agriculture and downstream processing capability diversity of crops and growing seasons strong R&D capacity in biotechnology and materials science sound regulatory infrastructure Detailed scoping of proposal and development of project plans (2003) BI agreed, funded and research commenced (2004/05)

26 Focus on combined value and volume SPEIALTY Price $/T Pharma Specialty chemicals 1000 Biodiesel OMMODITY Volume (MT)

27 The plant biofactory Protein Oil HO Locking up current carbon HO

28 Low-value commodity products Protein Oil HO FAMEs Locking up current carbon HO EtOH Petrol additive Biodiesel

29 High-value specialty products Oleochemicals Protein Industrial oils & lubricants Oil HO Monomers (6, 9) Locking up current carbon HO Monomers ( HB, LA) BioNylon Polymers (PHB, PLA)

30 BI research stages Stage 1 Develop proprietary platform technologies for enzymatic synthesis in three focus areas Achieve proof of concept production in model plants Stage 2 Evaluate range of candidate products from Stage 1 Select first generation products Stage 3 Select most valuable product-crop combinations & achieve economic production in selected crop plants Develop supply chains omplete regulatory and registration R&D onduct extension and marketing

31 BI Stage 1 project portfolio Market analysis and business development Industrial oils Novel oils with unique functional groups and highvalue direct uses omplex monomers hemically complex monomers enable sophisticated polymers with innovative properties Protein biopolymers Novel structural proteins as advanced biomaterials and adhesives

32 BI Stage 1 project portfolio Market analysis and business development Industrial oils Vernolic Oil Epoxy Oils Polyacetylenic Oils omplex monomers Fatty Acid Monomers Hydroxy Oils Dicarboxylic Protein biopolymers Novel Silks Repeat Motif Adhesives

33 Oilseed projects in BI Stage 1 (PI) Market analysis and business development Vernolic Oil Epoxy Oils Polyacetylenic Oils Hydroxy Oils

34 BI Project 2: Vernolic oil (pathfinder) Aim is to develop a pathfinder oilseed plant having high levels of vernolic acid ( 12-epoxy linoleic acid) oils rich in vernolic acid are highly reactive and make excellent drying agents for use in oil-based or alkyd-resin paints paints containing vernolic-based drying solvents have much lower levels of VOs (market estimated to grow to US $3.5 billion globally by 2007) vernolic acid also can be used in manufacture of novel interpenetrating plastics, metal coatings, and other high value compounds bombykol (a sex pheromone which can be used as insecticide) traumatic acid (an intermediate in prostaglandin synthesis) Seed oils from Euphorbia lagascae and Vernonia galamensis are rich in vernolic acid (50-70%) but yields are low Vernolic H O O O

35 BI Project 2: Vernolic oil (pathfinder) 12-epoxygenase gene (pal2) cloned from repis palaestina 70% vernolic acid Vernolic H O O O

36 BI Project 2: Vernolic oil (pathfinder) pal2 12-epoxygenase gene (pal2) cloned from repis palaestina pal2 gene introduced into Arabidopsis and linseed 70% vernolic acid 5% vernolic acid 20% vernolic acid Vernolic H O O O

37 General problem for 12-modified FAs Low accumulation is a general phenomenon for plants expressing unusual 12-modified fatty acids Wild plant Transgenic plant % in seed oils Vernolic Ricinoleic repenynic Eleostearic

38 BI Project 3: Poly-epoxy oils an poly-epoxy fatty acids be synthesised in plants? main product of interest with high value in glues, resins, surface coatings currently made from petroleum, and by chemical epoxidation of polyunsaturated vegetable oils (soy, linseed) requires genes for epoxygenases that act on = bonds at other positions in acyl chain (e.g. 9 & 15) these enzymes will need to be able to work sequentially on previously epoxygenated acyl substrates H Linolenic (18:3) O O 9 epoxy 12 epoxy 15 epoxy H O O O O O

39 orrect biological functioning To be commercially viable as crop biofactories, plants engineered with novel oils will need to have: normal vegetative and reproductive performance high grain yield normal oil content in the grain high concentrations of desired fatty acid in the oil and be able to break down unusual oils during germination genes for specialised TAG lipases may need to be obtained from wild species containing these oils

40 Delivery and adoption challenges Product segregation industrial products produced from traditional food crops (e.g. oilseeds) will require strict segregation from food-grade products because they:- will not be approved for food use may actually be toxic genetic isolation & Identity Preservation will be important crop and product management tools dedicated industrial (non-food) crop plants may be preferred Freedom to operate long term large investment requires some certainty about ability to eventually commercialise products access to enabling plant biotechnology could be an obstacle international collaborations developing to overcome this

41 IP sharing + product competition Proprietary product traits Epoxy Hydroxy Acetyl Transformation methods Elite germplasm Seed promoters Agronomic traits Open-access platform and enabling technology

42 Planned E-US ooperation in Bio-based Product Research E-US Task Force on Biotechnology Research Oilseed rop Flagship Project planned to focus on production of novel plants oils as industrial feedstocks.

43 Planned E-US ooperation in Bio-based Product Research E-US Task Force on Biotechnology Research The time is now right for the public sector to invest in team-based approach to discover the nature of the barriers to successful production of novel fatty acids in plants Working Group report (March, 2005)

44 A word of advice for plant biotechnology GRADUATES