sofiproteol - Montpellier SupAgro

Conférence, « La chimie, ça se cultive »
Montpellier, le 08 mars 2011
L’exemple des oléagineux
Jean-François Rous, Sofiprotéol

Agenda
• SOFIPROTEOL Group
• Sustainability as developed in the biodiesel
activity
• Focus on the oleochemical activities

PROLEA, the French vegetable oils and proteins sector
I

SOFIPROTEOL, the industrial and financial actor of the
French vegetable oils and proteins sector
SOFIPROTEOL
Management of
investment funds
Industrial activities
Sectors of investments:
• Seed production and biotechnology
• Collect of crop and protein based seeds
• Industries processing oilseeds and protein
rich plants
• Nutrition and animal industries
• Support for innovation and sustainable
investment
Food and animal
sector division
• Holding SOFIAL
• From animal feed and
health to animal
production and animal
products
•GLON SANDERS
Total turnover: 6 b€
Close to 6 000 employees
Oilseeds division
• Holding SOPROL
• From crushing seeds to
end products for food,
feed, energy and
chemistry
•SAIPOL
•LESIEUR
•DIESTER INDUSTRIE
•DII
•OLEON
•NOVANCE
•EXPUR

SOFIPROTEOL, Industrial activities
Sales 2010 5.6 Mds €, 6300 employees
IDIA
Famille GLON
Management
SOFIAL
Pôle nutrition et filières
animales
GLON SANDERS
HOLDING
SAIPOL
SOPROL
Pôle valorisation des
oléagineux
FONDS
STRATEGIQUE
D’INVESTISSEMENT
IDIA
IN VIVO
SOUFFLET
AXEREAL
BUNGE
Coopératives négociants
FIDICOOP
FINÉGOCE
SAIPOL
DIESTER INDUSTRIE
GROUPE
GLON
LESIEUR
OLEON
DIESTER INDUSTRIE
INTERNATIONAL
GÉNÉRALE
CONDIMENTAIRE
NOVANCE
Partners
Animal Health and Feed
Seeds crushing (oil and
meal production)
Human food (oils and
sauces)
Renewable energies
Renewable chemistry

SOFIPROTEOL is active on the entire value chain:
Complex issues towards a better quality of life...
Contribute to a better quality meat,
through animal health and feed
Optimize the quality to reduce
the protein dependency
Oil meal
Animal health
and breeding
Breeders
Transformation
and animal
productions
Biotechnologies
Seeds
Pesticides
Growers
Collect of oil and
protein seeds
Crushing
Animal nutrition
Oils
Food
Helping in optimizing
Contributing to a the practices
Growers and breeders
sustainable agriculture
Oilseeds division
Food and animal sector division
Renewable
energies
Renewable
chemicals
Contribute to a better
quality food chain
Other industries in which Sofiproteol is involved
Developing more sustainable products
for a better quality of life

Agenda
• SOFIPROTEOL Group
• Sustainability as developed in the biodiesel
activity
• Focus on the oleochemical activities

Sustainability:
Optimisation of the collecting zone
Example: Le Mériot
150 km
100 km
• Situated in the middle of a
rape seeds production
region
• 1,5 million tons of rape seeds
produced within 150 km around
the factory in 2008. The factory
will transform around 1,1 Mt of
seeds at full capacity
• Transport downstream
• Seine based refineries for the
Diester
• Other factories from the group
for oils that are not transformed
on site
• Animal feed industrials
Surfaces and production of rape
seeds in 2008:
- 1 441 000 ha
- 4,7 million tons of seeds

Sustainability:
Continuous improvement programme
Many factors influence indirect N 2
O emissions from the ground
→ Modifying farming practices as a way to reduce emissions
Partnership UMT GES-N 2 O
-INRA, CNRS, Universities
-ARVALIS, CETIOM, ITB
Climate
Farming practices
Type of soil
(Photo J. Raimbault, CETIOM)
N 2
O
Emissions

Continuous improvement programme:
CETIOM audit
% of plot lands
• The process started in 2008
for rapeseeds farms
• > 10000 plots of land audited
• In 2009, more than 15000
plots of land were audited
• Partners : « OS »
50,0
40,0
30,0
20,0
2008
2009
10,0
0,0
3.9

The programme is conducted at all levels of the value
chain
illustration : G. Castagnon / Proléa
36%
1%
1%
11%
33%
11%
5%
1%
Farming Storage-Drying Transport Crushing
Semi-refining Methanol Transesterification Distribution

Sustainability, the driving force for the
development of oil-based refineries
• Strongly proteindependent
for animal
feed
• France imports 49%
of its protein needs
(Unip – 2006/2007) for animal
feed and has thus
imported 4,3 Mt of soy
meals in 2007 (Huilerie de
France)
• Obligation to reduce the
GHG emissions in
transport and contribute
to the fight against
climate change
• In 2005, France CO 2
emissions were 412 Mt
(DGEMP - Caisse des
dépôts – 2007)
• Transports represent
34% of the total GHG
emissions in France
(DGEMP - Caisse des
dépôts – 2007)
• Strong and increasing
demand for diesel type of
fuel
• In 2007, 33 Mt of diesel
were consumed in
France and 10 Mt of
gasoline (source CPDP)
• In 2007, 73,9% of new
cars were diesel ones
(source CCFA)
• 34% of the diesel
consumed in France is
imported (Russia and
Middle-East) and 37% of
gasoline production is
exported (USA)

Agenda
• SOFIPROTEOL Group
• Sustainability as developed in the biodiesel
activity
• Focus on the oleochemical activities

Raw materials
Vegetable oil production in France
2500
2000
1500
1000
Surfaces en oléagineux (1000 Ha)
Oleaginous surfaces
Soja soy
sunflower
Tournesol
8000
2,23 MnHa
7000
6000
5000
4000
3000
Production d'oléagineux (1000 T)
Oleaginous seed production
soy
Soja
sunflower
Tournesol
7,35 MnT
500
rape Colza
2000
1000
rape
Colza
0
90 91 92 93 94 95 96 97 98 99 00 01 02 03 04 05 06 07 08 09
• French oilseeds production (2010) : 6,452 MnT
• SAIPOL: 70% of the French crushing capacities
0
90 91 92 93 94 95 96 97 98 99 00 01 02 03 04 05 06 07 08 09
(From FOP)
SUNFLOWER OILS
• High oleic sunflower (HOSO)
• 50% of the sunflower production (France)
France - 882 kt / EU27 - 3 402 kt
• 80% used for human food
high oleic
82
classic 21
0% 20% 40% 60% 80% 10 0 %
oleic
linoleic
saturated

European oleochemical development:
Biodiesel (FAME) & Glycerol production
SEMI-
REFINING
TRANS-
ESTERIFICATION
1.5t semi
oil
refined oil
1.5t biodiesel
150kg glycerol
GLYCEROL data
Production 2010
World
EU-27
1 690 kt
980 kt
BIODIESEL data
Production 2010
World
16.9 million tons
EU-27
9.8 million tons
EU Biodiesel content (1st and 2nd gen)
2010 2020
(vol.) 6.26% 10.89%
Grade/Market price (EU)
Crude (82-90%) ~€200/t
Refined (99%+) ~€500/t

Focus on the oleochemicals activities:
Diester Industrie, the largest producer of glycerin
KT
3000
2500
2000
1500
Worldwide
glycerin
production
Glycerin from
biodiesel origin
1000
500
0
1995 2000 2005 2006 2007 2009 2010
Glycerin from
Diester
Industrie
350 KT crude glycerine production, 150 KT refining capacity

Expected evolution of the global glycerin market
• Continued strong growth in the next 5 years
• Roughly 2.5 million tons today, 3.5 million tons in 2015
• Growth driven mainly by Biodiesel and also by oleochemicals
• In parallel, strong growth of existing and new applications
• Mainly glycols substitution in various market segments
• Development of current known applications: polyols for polyurethane
type polymers, surfactants, or ketals for solvent applications
• Ramping up of new applications: Epichlorhydrine, MPG, fermentation,
other…
• Overall the market should stabilize and prices should come
back to “normal” levels
• It is critical for new projects to target higher value added applications

Glycerol as a Platform Chemical
TRANSFORMATION
PRODUCT/APPLICATION
Epicerol process
O
Cl
Epichlorhydrin
Epoxy resins
OH
Enzymatic conversion
HO
OH
1,3-Propanediol
Polyesters fibres PTT
SORONA, CORTERRA
OH
OH
Catalytic hydrogenation
Via acrolein obtained
by glycerol dehydration
HO
O
OH
OH
Propylene glycol
Acrylic acid
Solvent
Esters
Coating resins, adhesives
Polyacrylates
Superabsorbants
Carbonylation
Urea / catalytic Zn
HO
O
O
O
O
Glycerol carbonate
Alkyd resins
Solvent
Glycidol
Enzymatic conversion
HO
OH
Dihydroxyacetone
Sunless tan

Example:
GLYCEROL CARBONATE
Process
HO
OH
OH
+
O
ZnSO 4
140°C
H 2 N NH 2
vacuum
HO
O
O
O
+ 2 NH 3
Ref: EP0955298
Product/Applications
GLYCEROL CARBONATE
Pilot production
Grade
Crude : 85%
Distilled : > 97%
USES
Building block polycarbonates,…
Reactive solvent alkyd resin manufacture
Cosmetics formulation
Ammonia fertilizer, synthesis,…

Evolution of glycerol main applications
2009
2.2 million tons
2015 (est.)
3.5 million tons
Traditional uses
66% of which :
Alkyd resins
7%
Cosmetics
Soaps
Pharmacy
33%
Food &
Drinks
9%
Cellulose
films
6%
Animal Nutrition
16%
Tobacco
3%
Polyols
14%
Esters
(surfactants,
emulsifiers,
…)
15%
Paper
Others1%
12%
Energy
13%
Glycol
substitution
2%
Epichlorhydrin
1%
Biomethanol
2%
53%
10%
New applications likely to represent
30% of glycerin uses by 2015
▪ Higher requirement in refined
glycerin for these applications
9% Glycol
substitution
6%
Epichlorhydrin
12%
Propylene Glycol
3%
Acrylic acid
1%
Biomethanol
6%

Fatty acids (esters) as Platform Chemicals
AMIDES, AMINES
O
BIOPOLYMERS
- polyesters
- polyamides,...
POLYOL ESTERS
jet engine lubricants
2-stroke engine oils
hydraulic fluids
slip agent in PE, PP, PVC films
inks/dyes dispersing agent amidation
(ammonia, amines, ...)
HOSO methyl oleate
polymerisation
(via di/polyacids)
O
transesterification
- trimethylolpropopane
- pentaerythritol
- dipentaerythitol
O
< cross/homo >
metathesis
NR 2
azelaic pelargonic
ASA
Alkenyl Succinic Anhydrides
OR
ene
O
O
O
O
Paper sizing
Wood treatment
fermentation
ozonolysis
PAO, w-unsaturated FA
lubricants +
O
O
-unsaturated esters
DIACIDS, POLYACIDS
COOH
COOH
SHORTER CHAIN MONO/DIACIDS
O O O
HO
OH HO
plasticizers
polyamides
skin care
lubricant esters
whitening agent

Example:
ASA (Alkenyl Succinic Anhydrides)
Process
O
O
10 9
7 7
R = Me,Bu
OR
O (x éq.)
O
T ~200 °C, 8h
Ene reaction
O
O
O
5 10
9 5
O
OR
+
Oléo-ASA
10
9
5 5
O
O
O
O
OR
▪ Applications
Grafting
on wood
Paper sizing agents
(Biobased alternative to isomerized
derived olefins)
Wood treatment
Eco-friendly process to treat
wood for risk class 4 uses
Ref: WO 03/049913
9
5 10 5
FP6 project - www.surfasam.com
O
O
OH
O
O
OR
lignocellulose

Example:
DIACIDS, Overview of applications
HO
O
O
OH
n
APPLICATION
Plasticizers
CARBON Nb
Lubricants
Polyesters
Polyamides
Alkyd resins
Solvents
Cosmetics
Pesticides
Anticorrosion additives
▪ Chemical approach
D9: ozonolysis of oleic acid
D10: alkaline cleavage of sodium ricinoleate
D12: cyclisation and oxydation of butadienes
Dx: metathesis
▪ Biotechnological approach
D18: Yeast fermentation
(eg Candida Tropicalis)

SOFIPROTEOL
12, avenue George V
75008 Paris
France
www.sofiproteol.com
Thank you for your attention…