Industrial Uses of Biobased Feedstocks Focus on Oleoproducts

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1 Industrial Uses of Biobased Feedstocks Focus on Oleoproducts Jean-Marc Pujol CROPS2INDUSTRY Bordeaux 1 J.M.Pujol

2 Rhodia Engaged in Chemistry of Several Plant Feedstocks eucalyptus spruce pine coconut palm soybean rapeseed peanut castor bean cellulose sugarcane corn sugars wheat rice fatty acids alcohols guar Plants: Plants: a source source of of natural natural molecules molecules and and polymers polymers 2 J.M.Pujol

3 Rhodia Engaged in Chemistry from Biomass for Growing Applications sucrose alcohols fatty acids cellulose Natural Natural molecules molecules and and polymers polymers for for numerous numerous applications applications solvents, monomers for inks, paints, coatings soaps, surfactants for shampoos and body wash plastics for automotive cables for filters additives for crop protection 3 J.M.Pujol Augeo Sipomer Rhovanil Rhodiantal Mirataine Alkamuls Miranol Rhodasurf Rhodameen Rhodapex Geropon Acetol Jaguar Rhodicare Rhodopol Rheozan Technyl exten

4 Rhodia : Downstream for Biorefineries Refinery : carbon flow from oil, coal and gas to applications Oil Fields crude oil Refineries fuels chemical intermediates Chemical Processes chemical specialties Formulation Downstream Industries Biorefinery : carbon flow from biomass (sugarcane, wood, rapeseed, wheat ) to applications Biorefineries Agriculture Fields biomass food biofuels paper, chemical intermediates Chemical Processes chemical specialties Formulation Downstream Industries 4 J.M.Pujol

5 Rhodia Biosourced Raw Materials Worldwide Feedstocks - Room for Growth at least in Europe spruce pine pine rapeseed corn/wheat pine rice pine castor bean guar sugarcane coconut palm sugarcane eucalyptus eucalyptus 5 J.M.Pujol

6 Status : Successes and Potential Current situation many examples of products coming from biomass, for diverse applications including high performance. Europe Europe a leader in agro production, Europe a leader in chemicals production, European raw materials from biomass still to develop for chemical use. The future A positive trend, Drivers: economics, regulation, innovation, Opportunities to create. 6 J.M.Pujol

7 Data to Consider : Today stable or decreasing oil production : 4 billions tons / year chemical industry uses 12 % of oil production (half as raw materials) increasing agriculture production : 4 billions tons / year chemical industry uses 2 % of agriculture production cellulose is the most abundant organic feedstock: more than 50 % of biomass, quantity synthesized by plants is 50 to 100 billions tons per year paper industry uses 1 % of cellulose production Cellulose > 50 Gt 500 Mt Oil Agri culture 300 Mt Oil for chemicals 4 Gt 4 Gt Cellulose for paper 7 J.M.Pujol

8 Future Growth Based on Biosourced Feedstocks Rhodia 4 billions sales employees France : 7 % sales, 30 % production, 33 % employees, 50 % R&D 2009 : 11 % raw materials coming from biosources cellulose ethanol oleochemicals guars Growth Ambition : increase based on sustainable development Ambition 2017 : 15 % raw materials coming from biosources 2020 : 20 % 8 J.M.Pujol

9 Future Growth should be based on Major Feedstocks Most important opportunities for chemical industry came from feedstocks driven by mass applications Oleo Feedstock (palm, soy, rapeseed ) food applications developed the feedstock biodiesel derivatives generated glycerol as a interesting feedstock for chemical industry Sugar/Starch (cane, wheat, corn...) food applications developed the feedstock biofuel gave an additional development and generated bioethanol interesting for polyethylene, polyoxyethylene, new fermentation biotechs may lead to new products Lignocellulose (pine, eucalyptus... bagasse) paper applications developed the feedstock future bioethanol 2nd generation may create coproducts interesting for chemical industry. 9 J.M.Pujol

10 Rhodia one of the Founding Members of ACDV Objective of our ACDV membership 2008: Identify feedstock sector for strategic development of future business growth Association Chimie du Végétal Biosourced Chemistry Association 10 J.M.Pujol Biomass Chemicals Leading Asset of Green Chemistry

11 Biosourced Chemicals : Positive Trend for Sustainability Limited fossil resources mainly located in sensitive countries strong price variations with a trend to higher prices A societal request Financial support from governments development of local resources diversification of energy sources reduce global warming from CO 2 Chemical companies engaged in sustainable development 11 J.M.Pujol

12 ACDV for the Promotion of Biobased Chemicals Association of chemicals and agricultural industries 12 J.M.Pujol

13 Natural Oils from Seeds and Fruits Biomass Feedstocks for Derivatives coconut palm soybean rapeseed peanut castor bean pressure extraction fatty acids lauric C 12 cetylic C 16 oleic C 18 stearic C 18 erucic C 22 triglycerides glycerol Augeo new solvents 13 J.M.Pujol

14 45 Oleochemical Feedstocks A Dominant Vegetable Output 5 distinctive segments Total production: 155 millions tons 40 16% millions tons % 7% 13% 28% 22% Palm Soybean Rapeseed Sunflower Animal fats Others 15% 85% Vegetale oils Animal fats Palm Coconut Palm kernel Soybean Rapeseed Sunflower Olive Peanut Cottonseed Corn Sesame Lard Butterfat Tall Oil Lineseed Fish Oil Castor oil 14 J.M.Pujol Source:Oil world 2009 Tallow/grease Palm oils Vegetable edible oils Animal fats Industrial oils Fish 32.2 % 51.5 % 14.3 % 1.4 % 0.7 %

15 General Context Battlefield and Rhodia s Positioning Battlefield Plantation Companies Crushers Oil Mills Oil Refiners 12 % Playground Oleochemicals Rhodia Surfactants Converters End users 12 % 6 % Feed Biodiesel Plastics Soaps 76 % Food Personal care Food-Feed Candles 15 J.M.Pujol Source APAG 2008, Oil world 2009, Berlin Icis Oléo Conférence Oct. 2009

16 Vegetable Oils Usage Food & Industrial Markets Vegetable Oils 155 kt FOOD 104 kt INDUSTRIAL 38 kt FEED 13 kt SOAPS 8 kt OLEOCHEMs 11 kt BIODIESEL 19 kt Oleochems (not inc soap) are only 7% of the global vegetable oil market. Food (76%) dictates market dynamics Fuel / Biodiesel (12%) is becoming an increasingly important factor 16 J.M.Pujol Source Icis 2009

17 Biosourced Fatty Acids Feedstocks for Many Surfactants Surfactants : molecules made of two distinct blocks: one presenting a strong compatibility with oils, one presenting a strong compatibility with water. fatty acids lauric C 12 cetylic C 16 oleic C 18 stearic C 18 erucic C 22 + polar part ions hydrophilic blocks surfactants ionics anionics cationics amphoterics non-ionics sourcing coconut palm kernel palm soybean rapeseed 17 J.M.Pujol

18 Biosourced Surfactants Applications in Fluid Formulations Due to their properties: foam control, surface modification, cleaning, emulsion, rheology : Miranol, Rhodasurf, Rhodameen Surfactants are used as performance additives for fluid formulations in several industries : personal care, home care, metal treatment, industrial cleaning, oil extraction, crop protection. The renewable source is a positive element for higher value added applications. 18 J.M.Pujol

19 Amphoteric Biobased Surfactants : Well Suited for Personal Care Betaines amphoteric surfactants : Mirataine Fatty acid + DMAPAmine + choroacetate Na very soft and foamy surfactant, compatible with other surfactants and soluble in electrolyte solutions emulsifiers, thickeners, antistatics, foaming agents for : shampoos, body washes, liquid soaps, bubble bath gels, conditioners,detergents. 19 J.M.Pujol

20 A Natural Origin Expected by the Consumers Cocoylisethionate sodium Geropon fatty acid + Surfactant for cleansing personal products shower gels, shampoos, facial cleansers, liquid soaps, brings softness for skin cleansing care, foaming agent efficient with hard waters, forms a light foam, leaves the user with a cleanliness and soft care feeling with light moisturizing. The consumer is looking for a natural product for skin care and soft feeling. Miracare Plaisant brings : high softness, deep cleansing, soft and silk feeling after use. 20 J.M.Pujol

21 Natural Oils : A Feedstock as well for Plastics Sebacic acid C 10 is synthesized from ricinoleic acid extracted from castor oil Polyamide 6,10 is prepared from diamine C 6 and sebacic acid C 10 PA6,10 broadens polyamides application field to high tech applications with: strong mechanical and thermal performances similar to PA 6, with a high melting point (215 C) an exceptional chemical resistance, similar to polyamides 11 and 12 Used to manufacture pipes and tubes for engine fuels in automotive applications Engineering Plastics are often able to replace steel and aluminum, since they can bring significant weight savings. A high performance application for a biosourced product in a highly technical sector. 21 J.M.Pujol

22 Polyamide 6,10 From Industrial Yarns to Engineering Plastics PA 6.10 is produced from 60% of natural resources Current market PA 6.10 is about 25kT mainly in monofilaments and toothbrushes Global castor oil production > 500 kt, less than 1 % of global production of natural oils Primary uses are in soaps, paints, lubricants Sebacic acid global production 25 kt, 5% of castor oil consumption Castor Oil Sebacid Acid 73w% 64% Castor seeds PA C Butadiene NH3 30w% 21w% ADN HMDA 36% 22 J.M.Pujol

23 Polyamide 6,10 High Performance Biobased Polymer Offers significant environmental footprint reduction 7 /Kg 5 /Kg 3 /Kg 10 /Kg Price PA 6.12 PA 12 PA 6.6 PA 6 Oil-based PA 10T PA PA 11 PA 6.10 Longer carbon chain + chemical resistance + low water uptake + low density Bio-sourced Shorter carbon chain + high barrier to fuels + high temperature resistance Based on HMDA and Sebacic Acid, PA 6.10 is the most economic Bio PA polymer. Compared to other high-performance polyamides, it offers technical performance and cost-effective profile. Its excellent chemical resistance to salts, as well as to steam and hot water and its low humidity absorption characteristics makes it an excellent alternative to longer carbon chain polyamides. Climate change, kg CO2eq Using carbon from natural origin, and with simple and direct chemical processes: the synthesis of polyamide 6,10 is an efficient chemistry for CO 2 emission. PA 12 PA kg CO 2 saved PA J.M.Pujol

24 Bio PA for Automotive and Industrial Markets Additional Markets in Electronics for High T 2nd Generation Main market segment targets brake and clutch systems fuel lines, connectors water tanks for cold countries flexible hoses batteries gaskets Second generation bio based PA high temperature, low water sensitivity, dimensional stability fast growing markets such as electronics connectors, photovoltaic 24 J.M.Pujol

25 25 J.M.Pujol Backup

26 Sugar Feedstocks Combined with Oleoproducts For 100 % Biobased Products corn wheat starch enzymatic hydrolysis glucose sorbitol sorbitan RCOOH Biosourced fatty acid oil emulsifiers % biobased biobased Alkamuls non ionic surfactant sorbitan ester 26 J.M.Pujol

27 Sugar Feedstocks Combined with Oleoproducts For 100 % Biobased Products fermentation CH 3 CH 2 OH ethanol sugarcane saccharose ethanol acetaldehyde acetic acid ethanol ethyl acetate solvents for inks, coatings, paints, adhesives ethylene ethylene oxide 27 J.M.Pujol Rhodapex ESB70NAT SLES Sodium Lauryl Ether Sulfate + RCOOH Biosourced fatty acid