Industrial Oil Crops Supplying the

Chemical Industry

Anders S. Carlsson

Swedish University of Agricultural Sciences (SLU),

Alnarp

SEI / SIANI workshop 2014

Crude oil underpins all aspects

of modern society

10%

Petrochemical

industryFuel• Solvents

• Chemical feedstocks

• Lubricants

• Plastics

• Synthetic fibers

• Synthetic rubber

• Detergents

• Chemical fertilizers

• Transportation

• Industrial sector

• Residential/Commercial

• Electric utility

Global annual consumption

of crude oil in 2012:

4,000 million metric tons

90%

Fossil oil alkane

Fatty acids

Myristic acid

(14:0)

Oleic acid

(18:1)

Glycerol

Oil molecule (triacylglycerol)

Plant oils are very similar in chemical

structure to fossil oil.

Plant oil

Fossil oil

Fossil oil is mainly derived from plankton oils converted from fatty acids into

alkanes during high temperature and pressure under millions of years .

Source: USDA

160 million metric

tons

Palm34%

Soybean27%

Rapeseed15%

Sunflower9%

Palm Kernel

4%

Cottonseed3%

Peanut3%

Coconut3%

Olive2%

Oil Usage (%)

80

614

Industry

Feed

Food

World Plant Oil Production 2012

Replacing fossil oil with plant oils

Feedstock

10%

Fuel 90%

Fuel

3.5%

Feedstock 40%

Plant oil

160 million

tons

Several options

Food oils

Industrial oils

Oil crops

Risk mitigation

Plant oil feedstocks

Oleic acid (18:1)

Technical oil qualities

Fatty acids with functional group

Epoxy

Hydroxy

Conjugated

Very long fatty acids

Medium fatty acids

Wax esters

FeedstocksFood Feedstocks

’Multi purpose’ oils

Requirements

Oil Crop Platform

High quality of product

Low price

Use of existing production infrastructure

Low environmental impact

Non-food oil crops producing technical oils.

Identity preservation and low risk of out-crossing

Availabillity of modern breeding tools

EU 7th Frame Program

ICONIndustrial Crops producing added

value Oils for Novel chemicals

Large collaborative 5 yrs project

(6 million € of EU funding, total budget 10.7 miilion € )

Third country participants:

Canada

USA

Australia

China

Coordinated by Prof. Sten Stymne, SLU

The jojoba plant has seed oil (wax esters) with excellent

lubrication properties. Due to high production cost only

used in high-end products such as cosmetics. If made

cheaper this oil quality would make an excellent

alternative to fossil oil as feedstock for engine and

mashine lubricants.

Fatty acid

Fatty alcohol

Wax esters differ structurally from common plant oils

Wax esters

Common plant

oil i.e. triacyl-

glycerol (TAG)

Production of biolubricants

in form of wax esters

in industrial oil crops using

plant biotechnology

An icebreaker in

industrial plant oils

In order to facilitate regulatory approval of GM crops for industrial uses,

we were not using any food crop or any crop that can easily cross with

food crops as vehicle for the industrial oil qualities

Crambe abyssinica

Brassica carinataCamelina sativa

Choice of Oil Crops

We should not use any part of

the plant for feed uses

In order to find non-feed added value

for the seed cake, one ICON partner (Innventia) was

developing methods to produce plastics from it.

18:1-CoA

Chloroplast

Fatty acid production in

the chloroplast

22:1-OH20:1-CoA

22:1-CoA

22:1-22:1Wax

esters FAE

FAR

WS

FAR and WS genes from Jojoba were used to modify oil

production (transgenic) in the three chosen oil crop

platforms to produce wax ester qualities.

Cytosol

Oil crop platforms producing added value oils

Wax ester (jojoba quality)

Fatty acid reductases (FAR) and wax

synthases (WS) are ubiquitous enzymes in

bacteria, protista, animals and plants

Over 30 FAR and WS genes from various

organisms were characterized in ICON

Why is that important?

By varying the length of and/or the number of functional

groups on the fatty alcohol and/or the fatty acid carbon

chains, different wax ester qualities for a wide range of

feedstock applications can be achieved.

Fatty acid Fatty alcohol

We have now wax ester of jojoba type in all

three of our industrial oil crop platforms

( up to 50% of the oil).

Winterized Camelina sativa seed oil

Wild typeWS3- 4 -14

Wax

esters

Transgenic Crambe lines

Wax

esters

Triacylglycerols

Transgenic Carinata lines

Wax esters

Triacyl-

glycerols

18:1-CoA

Chloroplast

Fatty acid production in

the chloroplast

20:1-CoA

22:1-CoA FAE

Three gene construct for very high

erucic acid gave GM Crambe seed oil

with up to 77% erucic acid (Wt 59%)

Cytosol

Oil crop platforms producing added value oils

18:2-CoA

Genetic

block of

this

pathway

22:1 FA

22:1 FA

LPAAT22:1 FA

(ultra-high erucic acid)

Erucic acid is transformed

into erucamide that is used

for lubrication and as slip

agent to decrease friction in

polymer and plastic

industry

Field tests in Sweden 2012 and 2014 with Crambe

with 20% wax esters and 73% % erucic acid

Grease manufacturing

and lubrication

tests by Axel

Christiernsson

International

AB

The ICON project was regarded as a success story

by European commission

E.g.

Conjugated FA (USDA)

Ricinoleic FA (WSU, Montana State university)

Cyclopropane FA (Brookhaven National Laboratory)

Different medium chain fatty acids (University of Nebraska)

High Omega-7 FA (Brookhaven, University of Nebraska)

Acetyl-triacylglcyerols (Michigan State University, Kansas State University

In parallell to ICON, a number of research groups

are working with developing other industrial seed

oil qualities with biotechnology in USA.

How can we increase the total production of plant oils?

There is one more problem…Plant oil 160 MT/year

Oil Usage (%)

80

614

Industry

Feed

Food

A large portion of

the plant oil is

today used for food

Plant Oil

Weat Maize

Future oil crops with biotechnology

Sugarbeet

Starch to oil

Sugar to oil

2.5 ton oil/ha4 ton oil/ha

Thank You

Monsanto estimate that it costs up to 60M USD for one GM

event!

In US, permission for commercial cultivation of GM

crops at very low cost can be granted if it is contract

farmed and the permit holder surveil the cultivation to

make sure that seeds and plants are not spread outside

the contracted area. Example: Arcadia Biosience

Safflower with gamma-linolenic acid (Sonova 200).

• No expensive animal tests have to be done for pure non-food crops

• Non-food GM oil and products can be exported to any country in the

world without any regulatory approval and without any GM label.

What about de-regulation costs?