Salisbury and Green - The peak industry body for the ...€¦ · Industrial Use of Vegetable Oils...
Transcript of Salisbury and Green - The peak industry body for the ...€¦ · Industrial Use of Vegetable Oils...
Non-food uses:Opportunities for the Australian oilseed industry
Phil Salisbury & Allan Green
The petrochemical factory
Unlockingancient carbon
(non-renewable)
AOF Innovations Committee Report:Industrial Use of Vegetable Oils
Report evaluates:
Current and future uses of edible vegetable oils for industrial purposes, either directly or after fractionation
Current 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
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
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
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
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 C16–C18) 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
Use as oleochemicals
Total oleochemical production
010002000300040005000600070008000
1995 2000 2010
Oleo
chem
ical k
T)Europe AmericaAsia Others
Use as oleochemicals
World oleochemical production
0100020003000400050006000700080009000
1995 2000 2010
Oleo
chem
ical (k
T)Fatty acids Fatty Methyl Esters
Fatty alcohols – natural Fatty amines
Glycerol – natural Basic oleochemicals
Use of existing industrial (non-edible) vegetable oils
High Erucic Acid RapeseedHEAR 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
Use of existing industrial (non-edible) vegetable oils
Crambe Crambe 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, Crambe has yielded well (>1t/ha) in Mallee type environments
Commercial adoption limited by high glucosinolate meal
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.
Domestication of wild industrial oil species
One limitation to the use of current vegetable oils as oleochemicals is that most oils predominantly consist of C16 and C18 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.
Some unusual industrial fatty acids
lauric acid(detergents)
conjugated fatty acids(superior drying oils)
petroselenic acid(polymers, detergents)
ricinoleic acid(lubricants, cosmetics
pharmaceuticals)
vernolic acid(resins, coatings,
plasticisers)
erucic acid(polymers, cosmetics,inks, pharmaceuticals)
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
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
Domestication of wild industrial oil species
DisadvantagesUndomesticated 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
Indicative oil yields (t/ha) of traditional and potential new oilseed crops
0.2
0.2
0.3
0.3
0.4
0.7
0.9
1.3
1.7
1.0
Sunflower
Linseed
Lesquerella
Dimorphotheca
Euphorbia
Calendula
Rapeseed
Crambe
Lunaria
Limnanthes
Premium prices obtainable forspecialty oils are insufficient to offset current low oil yieldsof most candidate new crops
Domestication of wild industrial oil species
DisadvantagesOften a lack of understanding of breeding systems, phenology andareas 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
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
Where to in Australia?
Need to identify (higher value) product areas where Australia is competitive or could develop a competitive advantage:
Current and future uses of edible vegetable oils for industrial purposes, either directly or after fractionation - NO
Current use of existing industrial (non-edible) vegetable oils - NO
The further domestication of existing wild species that produce industrial oils – SOME NEW CROPS 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 PLACED WITH SEVERAL POTENTIAL PATENT POSITIONS
Crop Biofactories Initiative
Strategic alliance between CSIRO and GRDC Plant Industry, Entomology, Molecular & Health Technologies
Collaboration between materials scientists and biotechnologists to focus on future materials that could be made from future plants
Focus areasIndustrial Oils
Complex Monomers
Protein Biopolymers
Three stagesStage 1 from 04/05 to 07/08 ($13M co-investment)
Stage 2 & Stage 3 conditional on outcomes of Stage 1
Expected time of up to 10 years until commercialisation
Crop Biofactories Initiative
CSIRO~GRDC~RIRDC national survey of expertise & interest in building an Australian biotransformation industry (2002)
International Workshop on Biotransformation (2002) held to explore Australia’s competitive niche
advanced agriculture and downstream processing capability
diversity of crops and growing seasons
strong R&D capacity in biotechnology and materials science
sound regulatory infrastructure
Crop Biofactories Initiative
CSIRO~GRDC~RIRDC national survey of expertise & interest in building an Australian biotransformation industry (2002)
International Workshop on Biotransformation (2002) held to explore Australia’s competitive niche
advanced agriculture and downstream processing capability
diversity of crops and growing seasons
strong R&D capacity in biotechnology and materials science
sound regulatory infrastructure
Detailed scoping of proposal and development of project plans (2003)
CBI agreed, funded and research commenced (2004/05)
Focus on combined value and volume
Volume (MT)
Price$/T
1000
2000
3000
Specialty chemicals
Pharma
COMMODITY
SPECIALTY
1 20 3
Biodiesel
The plant biofactory
Protein
Oil
CHO
CHO
Locking upcurrent carbon
Low-value commodity products
Protein
Oil
CHO
CHO
FAMEs
“Biodiesel”
Petrol additiveEtOH
Locking upcurrent carbon
High-value specialty products
Protein
Oil
CHO
CHO
Industrial oils & lubricants
Oleochemicals
Polymers(PHB, PLA)
Monomers( HB, LA)
Locking upcurrent carbon
“BioNylon”
Monomers(C6, C9)
CBI research stages
Stage 1Develop proprietary platform technologies for enzymatic synthesis in three focus areas
Achieve proof of concept production in model plants
Stage 2Evaluate range of candidate products from Stage 1
Select first generation products
Stage 3Select most valuable product-crop combinations & achieve economic production in selected crop plants
Develop supply chains
Complete regulatory and registration R&D
Conduct extension and marketing
CBI Stage 1 project portfolio
Industrial oils
Complex monomers
Protein biopolymers
Novel oils with unique functional groups and high-
value direct uses
Chemically complex monomers enable sophisticated polymers with
innovative properties
Novel structural proteins as advanced biomaterials
and adhesives
Market analysis and business development
CBI Stage 1 project portfolio
Industrial oils
Complex monomers
Protein biopolymers
VernolicOil
EpoxyOils
HydroxyOils
Poly-acetylenic
Oils
Fatty AcidMonomers Dicarboxylic
NovelSilks
RepeatMotif Adhesives
Market analysis and business development
Oilseed projects in CBI Stage 1 (PI)
VernolicOil
EpoxyOils
HydroxyOils
Poly-acetylenic
Oils
Market analysis and business development
CBI Project 2: Vernolic oil (pathfinder)
OH
O
CC
CC
CC
CC
O
CC CC
CC
CCC
C
Vernolic
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 VOCs (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
CBI Project 2: Vernolic oil (pathfinder)
∆12-epoxygenase gene (Cpal2) cloned
from Crepis palaestina
70% vernolic acid
OH
O
CC
CC
CC
CC
O
CC CC
CC
CCC
C
Vernolic
CBI Project 2: Vernolic oil (pathfinder)
Cpal2 gene introduced into Arabidopsis and linseed
Cpal2
∆12-epoxygenase gene (Cpal2) cloned
from Crepis palaestina
70% vernolic acid 5% vernolic acid
20% vernolic acid
OH
O
CC
CC
CC
CC
O
CC CC
CC
CCC
C
Vernolic
General problem for ∆12-modified FAs
Low accumulation is a general phenomenon for plants expressing unusual ∆12-modified fatty acids
0
20
40
60
80
100
% in
see
d oi
ls
Wild plantTransgenic plant
Vernolic Ricinoleic Crepenynic Eleostearic
CBI Project 3: Poly-epoxy oils
Can 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 poly-unsaturated vegetable oils (soy, linseed)
requires genes for epoxygenases that act on C=C 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
OH
O O
CC
CC
O
CC CC
CC
CCC
C
O
CCC C
OH
O
CC
CC
CC CC
CC
CCC
C CCC C
Linolenic (18:3)
∆12 epoxy∆9 epoxy ∆15 epoxy
Correct 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 downunusual oils during germination
genes for specialised TAG lipases may need to be obtained from wild species containing these oils
Delivery and adoption challenges
Product segregationindustrial 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 operatelong 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
IP sharing + product competition
Proprietary product traits
Hydroxy AcetylEpoxy
Open-access platform and enabling technology
Transformation methods
Elite germplasm
Agronomic traits
Seed promoters
Planned EC-US Cooperation in Bio-based Product Research
Oilseed Crop Flagship Project … planned to focus on production of novel plants oils as industrial feedstocks.
EC-US Task Force on Biotechnology Research
Planned EC-US Cooperation in Bio-based Product 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)
EC-US Task Force on Biotechnology Research
A word of advice for plant biotechnology GRADUATES