1. west|east|transfer Bratislava, January 2013 WP 8.1. Determination of market potential for selected platform chemicals Itaconic acid, Succinic acid, 2,5-Furandicarboxylic acid Executive summary PL CZ HU U A DE weastra s.r.o | Tallerova 4 | 811 02 Bratislava | Slovakia | www.weastra.com | info@weastra.com Funded by the 7th Framework Programme of the European Union, FP7 Knowledge based Bio-Economy, Collaborative Project, Grant agreement number: 289194, KBBE.2011.3.4-02 Towards a sustainable bio- industry Biotechnology for renewable chemicals and innovative downstream processes. www.bioconsept.eu

2. west|east|transfer 12/2012 2 Copyright and Disclaimer Copyright 2012 WEASTRA s.r.o. Layout and Design: Weastra and RTD Services Pictures: Shutterstock All Rights Reserved. This document was prepared by WEASTRA s.r.o. within the FP7 European Union funded project BioConSepT and will be therefore a publicly available document. No part of this document may be circulated, copied, quoted, or otherwise reproduced without the approval of WEASTRA s.r.o. Disclaimer: WEASTRA (www.weastra.com) is a boutique management consultancy based in Slovakia, supporting mid- sized and large enterprises in their business growth in emerging markets or new technologies. Weastras services related to R&D consist of market analyses for novel products and technologies, strategic management of R&D outcomes including the development of successful go to market strategies. Weastras market reports and market analysis documents are tailor-made publications for weastras clients. Quantitative and qualitative market information in this document is based on secondary research of publicly available information (like published patents, websites of companies, annual reports etc.) as well as on interviews or email responses from market players done in 2012. The market model projections have been developed solely by WEASTRA s.r.o. and have been challenged by relevant market players in order to correct assumptions deriving from secondary research. WEASTRA s.r.o. takes no responsibility for any incorrect information supplied to us by producers, potential consumers or other market players. Contact for further information: E-mail: info@weastra.com 3. west|east|transfer 12/2012 3 Project Overview (1/2) Approach & major primary & secondary sources leveraged in the analysis. Thorough primary and secondary market research was performed - the market report and the market potential calculations include insight from numerous interviews and email responses from key industry players (producers, distributors, consumers). Market model for the market potential calculations was developed and challenged by the main producers or consumers of the bio-based platform chemicals Deliverable : Final report incl. the market model, January 2013 1. ~50 interviews with intermediates producers/distributors 2. Information from major bio-based intermediate producers 3. Interviewed potential consumers & market experts e.g. Primary sources (interviews, email responses) Studies of national and international institutes Reports of relevant business associations Official statistical data Governmental documentation Industry specific data insights Publicly available information on key market players 3rd party market reports Secondary research 4. west|east|transfer 12/2012 4 Project Overview (2/2) Chemicals in scope of the analysis, as agreed by WP6 members. Scope of analysis as agreed with WP6 members during phone call interviews : Succinic acid, Itaconic acid, FDCA (LCDAs were not specified and therefore out of scope) petrol-based or bio-based alternative intermediates or routes were part of the analysis due to the market potential calculations ITACONIC ACID SUCCINIC ACID 2,5-FURANDICARBOXYLIC ACID Primarily analyzed chemicals Terephthalic acid Isophthalic acid Adipic acid petrol & bio based Petrol based succinic acid 1,4 BDO Maleic anhydride Phthalic anhydride Acrylic acid petrol & bio based Bisphenol A Others analyzed due to their connection to primary focus chemicals HO O OH O CH2 HO O OH O HO O OH O O 5. west|east|transfer 12/2012 5 HO ITACONIC ACID HO O OH O CH2 6. west|east|transfer 12/2012 6 ITACONIC ACID Current market volume & value. 24% 37% 3% 19% 18% Zhejiang Guoguang Biochemistry Qingdao Kehai Biochemistry Jinan Huaming Biochemistry Alpha Chemika Others 41,400 MT Production location: mainly shifted to China Production Capacity: Current estimated output at 41,400 MT, quick ramp-up of add. capacity possible as production of citric acid can be easily switched to IA Route: Fungal fermentation of Aspergillus terreus, Aspergillus niger, Ustilago maydis, Candida mutant Costs: trending downwards due to production in China, but declining demand (crisis, few applications) Distribution: Mainly China, India often via producers Price: US$ 1,800/MT US$ 2,000/MT depending on supplier & quality where most end use applications remain possible at current price level Production by producers 2011 Key Findings IA production mainly in China - stagnating at ~41.400 MT p.a. due to few end use applications with limited potential. Global production capacity at approx. 80.000 MT, none of them in the USA or EU Price oscillating between US$ 1,800/MT US$ 2,000/MT depending on supplier and quality grade which is fine for most end uses. Overall market value of approximately US$ 74,5 mio. (2011) 7. west|east|transfer 12/2012 7 ITACONIC ACID Current & future applications and competitive routes. Potential replacement of STPP (sodium tripolyphospate -> toxic) by Poly-IA in detergents Other successful phosphate free builders already on the market A-Zeolit Poly-IA acid needs to bring novel properties in order to be competitive. Too many players. Tough market Potential replacement for Maleic acid in area of UPR and fumaric acid - not a drop in but a good substitute 100% bio based polyester composites - DSM patent published in 5/2012 Big market - BUT green fumaric acid by Myriant already on way - drop in replacement DETERGENT BUILDERS Potential by replacing classical amino carboxylate dispersant agents by Poly-IA acid Several other bio based substances on market Novel properties needed in order to succeed in the marketCHELATING AGENTS THERMOPLASTIC Poly-IA acid is able to target SAPs, but low feasibility as bio-based acrylic acid is going to be as drop in replacement soon low potential SUPER- ABSORBENTSLATEX SBR and synthetic latex is todays biggest application of IA, covering ca 44% of the production, ca 18.000 MT of IA steady growth, low potential IA is rather intermediate for novel products than for drop-in replacements Current applications have limited potential- SBR & synthetic latex (~50%), resins, Poly- IA used mostly in chelants, detergents, water treatment Potential replacing MAN in field of polyester composite resins DSM is on the way to commercialization. But bio-based fumaric acid probably a better replacement Huge potential of IA use in production of MMA patent published Possible production of BIO - MMA (PMMA market) out of IA - Lucite International patent published in 2012 Lower prices of IA needed in case it should be cost competitive to acetone cyanohydrin POLYESTER COMPOSIT RESINS 8. west|east|transfer 12/2012 8 ITACONIC ACID Market potential. Most interviewed players do not see potential for IA, there is only 3 players who are focusing on IA, out of which the MMA production and MAN replacement in UPR being groundbreaking for the itaconic acid potential. The projected market by 2020 is ca. 407,790 MT in value of 567 Mio USD in case the MMA production would be feasible. If not, than potential for 2020 is max. 197,400 MT (315 Mio USD) Production of MMA For drop in replacement of acetone cyanohydrin a lower itaconic acid price needed for being competitive Replacement for MAN in UPR Bio-based fumaric acid will be probably a better replacement as it can be as a drop in, IA needs to bring novel properties Detergent builders Need of costly market education and commercialization of completely novel products into existing markets. Competition of A-Zeolit Replacement for acrylic acid in SAPs - bio-based acrylic acid will take most of this potential 213 77 50 44 24 Thermoplastics (MMA) UPR Existing market Detergent builders SAPs Projected Market volume in 2020 (1,000 MTPA) Replaced 1% in acrylic acid, CAGR 23% Replaced 5% in MAN, CAGR 38% (2014 - 2020) CAGR 3,6% Replaced 1.5% in STPP, CAGR 41,5% (2014 2020) Replaced 9,25% in acetone cyanohydrin CAGR 63% 1,890 1,664 1,609 950 50 Detergent builders Thermoplastics (MMA) SAPs UPR Existing market Addressable market volume (1,000 MTPA) based on the market size for 2011 The addressable market in this market report means the theoretical market potential for IA in case of being the winning technology replacing 100% of other routes 9. west|east|transfer 12/2012 9 SUCCINIC ACIDHO O OH O 10. west|east|transfer 12/2012 10 SUCCINIC ACID Current market volume & value. Market volume & prices 97 % of the SA production in 2011 was petrol-based. bio-based succinic acid was coming mainly from BioAmber (3.000 MT capacity of pilot plant approx. 350 MT output), BASF-Purac (500 MT) and Reverdia (300 MT) Price in 2011: petrol-based US$ 2,400/MT US$ 2,600/MT bio-based approx. US$ 2,860/MT - US$ 3,000/MT Production routes Via catalytic hydrogenation of petrochemical maleic acid or anhydride Bio-based route - fermentation of glucose using natural producers or engineered organisms, e.g. Anaerobiospirillum succiniproducens, E coli or Coryne bacteria Future production capacities Capacities of bio- succinic acid in 2014 approx. 230,870 MT and a large share will belong to Myriant (82,810 MT) Capacity in 2020 expected to be of min 642,450 MT - BASF (75,000 MT), Myriant (182,110 MT), Reverdia (10,500 MT) and BioAmber (327,000 MT) 1% 1% 1% 20% 15% 12% 9% 41% BioAmber BASF-PURAC Reverdia Lixing Chemical Kawasaki Kasei Chemicals Anqing Hexing Chemical Nippon Shokubai Others 40.000 MT SA Production in 2011 Market volume of SA in 2011 was approx. 40,000 MT only 1,150 MT bio-based Price of petrol-based SA is US$ 2,400/MT US$ 2,600/MT and bio-based SA is approx. US$ 2,860/MT 3,000/MT, with total market value approx. US$ 63.2 mil. From 2013 bio-based SA price will go down to US$ 2,300 2,400/MT Huge production capacities for SA are currently being built or are in pipeline reaching to 225,870 MTPA from 2014, going to min. of 637.450 MTPA in 2020. 36% 30% 11% 5% 18% Myriant BioAmber BASF Reverdia Others - petrol based 225.870 MTPA of SA capacities by 2014 11. west|east|transfer 12/2012 11 SUCCINIC ACID Market mechanism. FEEDSTOCKS CONVERSION SUCCINIC ACID (processing) CHEMICAL TRANSFORMATION MARKETS Access to feedstock New generation organism Converting technologies Distribution 12. west|east|transfer 12/2012 12 SUCCINIC ACID Current & future applications and competitive routes. The potential seems to be somewhere between polyester polyols and plasticizers. Interesting potential 2.5% of phthalic anhydride to be replaced by 2020. Replacement of adipic acid Polyester polyols attractive! 40% CAGR expected Target industries - forgiving chemistry really open for a new molecule to be tested Once the green adipic acid is on the market, the chances for succinic acid will be more limited - these intermediates might coexist PBS, PBST PLASTICISERS POLYURETHANES SOLVENTS ALKYD RESINS The most relevant and interesting market Replacement for MAN Major production capacities allocated to BDO Alternative bio-BDO routes on the way (Genomatica, Metabolix)- different quality and price levels but all will co-exist on the market BDO Small market of succinic acid coatings & pigments, PBS & other industrial apps. Biggest market potential is with BDO and PBS, low hanging fruits polyester polyols PA replacement is second largest target of the bio-SA producers, whilst plasticizer producers are skeptical for the use of long lifespan products e.g. flooring Potential on side of ethanol resin based solvents, not methanol resin based (not good properties of succinic acid, expensive production) No need of very high purity of succinic as for BDO and polyesters Solvents not in the primary focus of current succinic acid players Drop in instead of phthalic anhydride (PA), but PA has some good properties which SA needs to prove first. Potential customers see potential only in short lifespan products, but producers want to target big portions of the market e.g. flooring, walls etc., not the foil/food wrapping Replacement of adipic acid - coexistence with green adipic acid succinic acid will be cheaper, but adipic acid more suitable Nicest market for SA Currently small market but huge growth potential predicted in packaging applications. Projected CAGR for SA to 2020 is approx. 37% if completely bio-based and bio-degradable New applications PBST instead of PBAT 13. west|east|transfer 12/2012 13 SUCCINIC ACID Market potential. The addressable market for PA replacement is huge approx. 2.5 Mio MTPA however it will take long time to penetrate the market & prove the properties The projected market in 2020 will be approx. 599,449 MT in the value of approx. 538.8 Mio USD, with regard to other possible bio-based routes & intermediates 2,454 2,205 735 629 92 82 Plasticizers BDO Polyester polyols Alkyd resins Existing market PBS, PBST Addressable market volume (1,000 MTPA) based on the market size for 2011 316 92 82 51 37 21 BDO Existing market PBS, PBST Polyester polyols Plasticizers Alkyd resins Projected Market volume in 2020 (1,000 MTPA) CAGR 37% CAGR 13% Replaced 1% in PA and 2.5% in adipic acid CAGR 39.6% (2013 2020) Replaced 2.5% in PA, CAGR 30% (2013 2020) Replaced 4.5% in adipic acid, CAGR 40% Replaced 11% of MAN in BDO and new technology for BDO production from succinic (BioAmber), CAGR 43% from 2014 Production of BDO Drop in replacement for MAN, but there are also alternative routes to produce bio- BDO without using succinic acid (Metabolix, Genomatica) Replacement for PA and Adipic acid in plasticizers Big potential for replacing PA in plasticizers have also FDCA or Isosorbide with better properties in some cases Bio-based Adipic acid will be competing replacement, it can be as a drop in adipates. Replacement for adipic acid in polyurethanes Here low hanging fruit, succinic acid targets forgiving chemistry, quick wins possible. When bio-based adipic acid will be on the market, it can be as a drop in replacement, but it will probably focus more on polyamides market De-icers, solvents, coatings, pigments, pharma, others The addressable market in this market report means the theoretical market potential for SA in case of being the winning technology replacing 100% of other routes 14. west|east|transfer 12/2012 14 2,5-FURAN- DICARBOXYLIC ACID HO O OH O O 15. west|east|transfer 12/2012 15 Estimated development of production capacities 2012 Avantium 2016 * 2018 - estim. potential - long term 2,5-FURANDICARBOXYLIC ACID Recent market volume & value. Future Potential & market characteristics: Depending on end uses huge potential (over 50 mil MTPA) Avantium economically feasible new catalytic based route (1000 USD/MT) Pilot plant in NL 40 MTPA (2012) Industrial plant 30 50.000 MTPA (2016) Avantium operated Commercial plants 300 500.000 MTPA (2019) - license based Other potential producers: Several patents in the area of HMF, resp. MMF and FDCA synthesis Non of these declare to produce in a short time no publicly available agreements on commercialization as by Avantium) Today: 3.5 5 MT in value of ca. 10 Mio USD (Price: over US$ 2,300/kg ) Mainly used for laboratory testing and pharma, distributed to consumer in several kilograms or even grams Request based production - not many producers to produce * Avantium 40 MTPA Output 3,5 5 MT 50.000 MTPA 500.000 MTPA 50 million MTPA Synbias V & V Pharma Industries Carbone Scientific Tokyo Chemical Industry Chemsky others 2,5 FDCA nowadays not been commercialized because of price over US$ 2,300 /kg . Some labs produce FDCA, mainly in China on request for very small amounts (grams) Avantium license based production of FDCA by scale of 500,000 MT (2019) at 1000 USD/MT break through for FDCA 16. west|east|transfer 12/2012 16 2,5-FURANDICARBOXYLIC ACID Current & future applications and competitive routes. The low hanging fruit application is drop in replacement for TPA in PET, which is a huge market Also polyamides are being interesting but rather for new products with novel properties No agreements still on fields of polycarbonates and epoxy resins, polyurethanes, solvents and plasticizers Good potential for replacement of petroleum based solvents Not in the primary focus of Avantium, smaller potential than PET No commercial agreements done with potential FDCA producer yet Potential replacement of Bisphenol A (toxicity of BPA) Current consumption of BPA in this field ca. 3,8 mil MTPA Alternative bio routes for BPA replacement existing (e.g. isosorbid) Potential replacement for phthalic anhydride and maybe adipic acid (bio-adipic to come) PA not big willingness on side of end uses producers to change Novel FDCA formulas with new properties might be interesting Potential for green plasticizers instead of PA, rather than succinic, FDCA has better properties (solubility) Not in a pre commercial phase no agreements with Avantium yet The low hanging fruit market for FDCA is the replacement of TPA The best developed project - PEF instead of PET: Replacement for PET in applications, such as drinking bottles or fibers Comparable and even better properties as PET (but only colored products the base is yellow) Commercialization agreements done POLYAMIDES PLASTICISERSPOLYURETHANES SOLVENTS POLYCARB & EPOXY RESINS Low hanging fruit app is drop-in replacement for TPA in PET, which is a huge market Also polyamides are interesting but rather for new products with novel properties No agreements still on fields of polycarbonates and epoxy resins, polyurethanes, solvents and plasticizers Potential replacement of adipic acid and TPA Not a drop in but rather novel products as a combination of adipic and FDCA with new properties Commercialization agreements done POLYESTERS 17. west|east|transfer 12/2012 17 2,5-FURANDICARBOXYLIC ACID Market mechanism. FEEDSTOCKS CONVERSION PRE INTERMEDIATE FDCA (processing) CHEMICAL TRANSFORMATION MARKETS Access to feedstock HMF, resp. MMF Converting Technologies and distribution Other players with patents in HMF and FDCA Tejin Aramid - aromatic polyamides yxy based para-aramid fibers Rhodia - alyphatic polyamides in automotive, consumer goods, electronics Solvay - engineering plastics polyamides PEF bottles, and beverage packaging 18. west|east|transfer 12/2012 18 The total addressable market by replacement of all possible intermediates together with current end uses markets is ca. 5o.5 Mio MT The addressable market for PET replacement is huge approx. 40.7 Mio MT The projected production potential by 2020 is 498,016 MT in value of 498 Mio USD out of which 65% goes to PET and the rest mainly to polyamides, polycarbonates and plasticizers 322 80 42 34 14 6 PET Polyamides Polycarbonates Plasticizers Polyester polyols Solvents Projected Market volume in 2020 (1,000 MTPA) novel polyamides Replaced 0.9% in bisphenol A Replaced 0.6% in PTA TPA Several bio- TPA routes on stream - (isobutanol, mucoic acid, BTX, terpens, biodimethyl furan) Players in bio TPA Global bioenergies, Butalco, Butamax, Drath, Genomatica, AnelloTech, Sabic, Chemtex, UOP BUT FDCA based PET novel properties ! competitive advantage towards bio TPA PA, Adipic acid Bio Adipic acid to come in 2 years bio nylon Several other bio based polyamide routes on stream (caprolactam, castor oil, azealic acid, 9-octadecenoic acid) Bio polyamide players: Arkema, DSM, BASF, Verdezyne, DuPont BPA Alternative bio routes for BPA replacement existing e.g. Isosorbid As FDCA commercial production will exist only after 2018 real market exploitation possible rather after 2020 2,5-FURANDICARBOXYLIC ACID Market potential. Replaced 1% in phthalic anhydride and 1% in adipic acid Replaced 4% in phthalic anhydride and 0.2% in adipic acid Replaced 2% in solvents from NMP and 2% in solvents from THF Even to replace just a part of TPA by FDCA needs huge production of FDCA other applications based on FDCA to come not earlier than 2020, rather later! 41,632 2,905 2,454 2,329 944 208 PET , PBT Polycarbonates Plasticizers Polyamides Polyester polyols Solvents Addressable market volume (1,000 MTPA) based on the market size for 2011 19. west|east|transfer 12/2012 19 KEY LEARNINGS 20. west|east|transfer 12/2012 20 Key learnings 1:1 (drop in) replacements are more promising. The intermediates with biggest chance to have real success seems to be: Bio-adipic acid, bio-acrylic acid, bio-fumaric acid, Bio-succinic mainly by BDO and PBS, FDCA mainly by PET Time to market , price & commercialization on a global scale through partnerships are crucial for the success of drop-in replacements! The end uses where only novel products can be developed using the bio-intermediate: more difficult to educate and penetrate the market. Here the properties of product are more important than the price. Market acceptance depends on new value added Accessibility of feedstock as well as flexibility of feedstock used will play a big role in future: The mass production of bio based platform chemicals has to be served by huge feedstock input non food (second, third generation) - flexibility of feedstock type of advantage! The most important players becoming those on the beginning of value chain (e.g. Cargill), they can become a gate keeper for the whole chain. Even if the mass production of bio based platforms as drop-in, starts very soon - to replace just asmall part of petroleum based market (e.g. 10% of TPA) will take at least 10 years END USES FEEDSTOCK POTENTIAL vs CAPACITIES 21. west|east|transfer 12/2012 21 BACKUP 22. west|east|transfer 12/2012 22 General information itaconic acid is a chemical intermediate that was identified by the U.S. Department of Energy's biomass program as a top 12 Top Value Added Chemicals. Itaconic acid is also known as methylenesuccinic acid The chemical constitution of itaconic acid is similar to anhydride or maleic acid Currently, most of the production of Itaconic acid is concentrated in China Appearance: white crystal or powder ITACONIC ACID Key facts. Production routes Fungal fermentations: Aspergillus terreus, Aspergillus niger, Ustilago maydis, Candida mutant Earlier, itaconic acid was formed by the distillation of citric acid. Itaconic acid is chemical intermediate identified by U.S. Department of Energy as a top 12 target molecule Current production of itaconic acid is concentrated in China Itaconic acid is produced by fungal fermentation of carbohydrates such as glucose HO O OH O CH2 23. west|east|transfer 12/2012 23 ITACONIC ACID Production chain. Itaconic acid is produced industrially by fermentation of carbohydrates such as glucose using fungi, eg. Aspergillus terreus In applications can be used directly itaconic acid or polyitaconic acid Itaconic acid can be used as a substitute for maleic acid and fumaric acid in area of polyester composites resins FEEDSTOCK CONVERSION BUILDING BLOCK CHEMICAL TRANSFORMATION MARKETS Carbohydrates Fungal fermentation Itaconic acid Unsaturated esters Polyitaconic acid SBR and synthetic latex Superabsorbent polymers Chelant dispersant agents Polyester composites resins Builders in phosphate-free detergents DERIVATES OF ITACONIC ACID 2-methyl - 1,4 BDO 3-methyl THF 3- & 4-methyl GBL 3-methylpyrrolidine 24. west|east|transfer 12/2012 24 ITACONIC ACID Top consumers of Itaconic acid. DSM NETHERLANDS Description DSM is a leading global science-based company focused on the production of nutritional ingredients, industrial chemicals and pharmaceutical ingredients. DSM is most active in the area of production of UPR. The company is currently focused on the task of using itaconic acid in the most effective way for the production of UPR. Strategy partnership & development The company is already planning to start with the commercialization of their itaconic-based UPR The company is also involved in development and production of bio-based succinic acid and formed a joint venture with Roquette Frres S.A. for the manufacturing and commercialization of Biosuccinium - a sustainable succinic acid. Their manufacturing facility is planned to achieve a capacity of 10.000MT by 2015. Key Facts Technologies DSM is developing a route for 100% bio-based polyester composites and in May 2012 it published its patent for the production of bio- based polyester composites from itaconic acid. Markets DSMs activities are grouped in several business entities: Nutrition, Pharma, Performance Materials, Polymer Intermediates and Emerging business Areas focused on bio-based products, biomedical materials and advanced surfaces Target markets for its bio-based products include plasticizers, polyurethanes, personal care products, resins, coatings and other. 25. west|east|transfer 12/2012 25 ITACONIC ACID Top consumers of Itaconic acid. LUCITE INTERNATIONAL Description Lucite International is since 2009 a subsidiary of Mitsubishi Rayon Co., Ltd. The company is the global leader in the design, development and manufacture of acrylic-based products. Strategy partnership & development Lucite International and Mitsubushi Rayon declared that they would like to start with the commercial production of bio-based MMA in 2016. Their goal is to produce 50% of MMA, which is approximately 400,000 MT by bio-routes, out of which itaconic acid seems attractive. Lucite international claims to have established long-term cooperation with Shanghai SECCO Petrochemical Company Limited for using their HCN as one major raw material. Lucite has also partnership with Vopak Shanghai Limited for providing the logistic services. Key Facts Technologies The company is focusing on selection of renewable feedstocks and conversion to soluble carbohydrate, production of a number of different chemical intermediates by fermentation, conversion of these to methacrylates, directs production of methacrylates by fermentation Markets Lucite is a global leader in methacrylate monomers with around 1000kte of nameplate capacity a 25% global market share in this field. The Company is the single largest manufacturer of MMA for the global merchant market and is the only supplier demonstrating total commitment to this market. 26. west|east|transfer 12/2012 26 ITACONIC ACID Top consumers of Itaconic acid. Itaconix Description Itaconix Corporation is one of the world leaders in polymers made of itaconic acid. It was founded in 2008 by Dr. Yvon Durant, former associate research professor in material sciences at the University of New Hampshire, and John Shaw, president of Kensington Research Inc. The company develops, produces and sells new polymers made of itaconic acid using its patented polymer technologies. The companys first commercial product line, Itaconix DSP, are water-soluble polymers used in detergents and cleaners based on its chelation and dispersion properties. Strategy partnership & development Itaconix sees a big potential for polyitaconic acid as effective builders in detergents and cleaners, but is also focusing on developing new products based on novel properties possible from polymers of itaconic acid. In 2009, Itaconix received a $2 million grant from the USDA to research and develop the use of wood biomass as a feedstock for fermenting itaconic acid. The company worked with the University of Maine and the University of Massachusetts at Lowell to establish its ability to ferment itaconic acid from a variety of carbohydrate sources. In 2011, the company received an SBIR research grant from NSF for the enzymatic production of itaconic acid. In 2012, the company received an SBIR research grant from NSF to produce novel latex polymers. The company is working with partners in specific industries to develop novel applications of polyitaconic acids. Key Facts Technologies Polymerization of itaconic acid produced by fermentation with Aspergillus terreus using carbohydrates such as corn. The company is expanding its product capabilities around its range of linear, cross-linked and emulsion polymer technologies Markets Detergents and chelant dispersant agents Super Absorbent Polymers Thickening/viscosity modifier agent Binder in inks - Drilling mud modifier - Dispersant for paper coatings Fiber sizing - Sequestrant in mining Emulsifier in cosmetics 27. west|east|transfer 12/2012 27 General information succinic acid is a chemical intermediate that was identified by the U.S. Department of Energy's biomass program as a top 12 Top Value Added Chemicals. succinic acid is currently commercially produced via petrochemical production routes in small quantities bio-based production routes are currently being developed by numerous companies and research institutions production of petroleum-based succinic acid began in 1970s in China, bio-based succinic acid production began by BioAmber, since January 2010 the current market of succinic acid is very small and limited to niche applications because the petrochemical process is inefficient and costly. Appearance: colorless to white crystal or powder, soluble in water SUCCINIC ACID Key facts. Production routes Chemical route succinic acid is produced by catalytic hydrogenation of petrochemical maleic acid or anhydride maleic anhydride is manufactured from n-butane Biological route succinic acid can be produced by the fermentation of glucose using natural producers or engineered organisms, for example Anaerobiospirillum succiniproducens and Escherichia coli or other microorganisms such as Coryne-type bacteria feedstock used for production of succinic acid: wheat, maize, glucose, lignocellulosic derived sugar, sorghum grain to starch. Succinic acid is chemical intermediate identified by U.S. Department of Energy as a top 12 target molecule Current production of succinic acid is via petrochemical route from maleic anhydride First production of bio-based succinic acid began by american company BioAmber in January 2010 HO O OH O 28. west|east|transfer 12/2012 28 SUCCINIC ACID Production chain. As a feedstock for production succinic acid are using petroleum or biomass / sugar By petroleum way, chemical conversion to succinic acid is from maleic anhydride and by bio way is conversion by fermentation In applications can be used directly succinic acid or its derivatives FEEDSTOCK CONVERSION BUILDING BLOCK CHEMICAL TRANSFORMATION MARKETS Biomass / sugar Petroleum Maleic Anhydride Fermentation Succinic acid 1,4 BDO, THF, GBL, PBT, PTMG Succinic acid + 1,4 BDO PBS= Dimethyl Succinate and Diethyl Succinate Polyurethanes Alkyd resins Plasticizers Solvents & Lubricants Personal care & Pharma Deicers & Coolants Food & Flavors DERIVATES OF SUCCINIC ACID Coatings & pigments 29. west|east|transfer 12/2012 29 SUCCINIC ACID World map of production bio-based succinic acid. already operating under constructing or planned Pomacle, France Production of: bio-succinic Capacity: up to 3,000 MT Operating: since Jan 2010 Owner: BioAmberSarnia, Ontario Production of: bio-succinic, bio 1,4 BDO Peak capacity: 35,000 MT of succinic acid 23,000 MT of 1,4 BDO Operating: start-up in 2013 Owner: BioAmber Partner: Mitsui, Lanxess Lestrem, France Production of: bio-succinic Capacity: 500 MT Operating: since 2010 -demonstrational Owner: Reverdia Barcelona, Spain Production of: bio-succinic Capacity: 500 MT (2010) 25,000 MT (2013) Operating: 2010 demonstrational 2013 - commercial Owner: BASF - PURAC Leuna, Germany Production of: bio-succinic Capacity: 500 MT (2012) 5,000 MT (2014) Operating: start-up in 2012 Owner: Myriant Partner: UhdeInventa-Fischer Cassano Spinola, Italy Production of: bio-succinic Capacity: 10,000 MT Operating: start-up in 2012 Owner: Reverdia Lake Providence, Louisiana Production of: bio-succinic Capacity: 13,600 MT (2013) 77,100 MT (2014) Operating: start-up in 2013 Owner: Myriant Rayong, Thailand Production of: bio-succinic, bio 1,4 BDO Peak capacity: 65,000 MT of succinic acid 50,000 MT of 1,4 BDO Operating: start-up in 2014 Owner: BioAmber Partner: Mitsui,PTT,Mitsubishi Nanjing, China Production of: bio-succinic Capacity: 100,000 MT Operating: start-up in N/A Owner: Myriant Partner: ChinaNa9onalBlueStarUSA or Brazil Production of: bio-succinic, bio 1,4 BDO Peak capacity: 65,000 MT of succinic acid 50,000 MT of 1,4 BDO Operating: start-up in N/A Owner: BioAmber 30. west|east|transfer 12/2012 30 Description In late 2007 DNP Green Technology and ARD formed a joint venture called BioAmber. Later, in October 2010, DNP Green Technology acquired 100% of the joint venture from ARD and changed its corporate name to BioAmber Inc. Became the first company to market bio-succinic acid , which is 97% bio-based, as certified by the United States Department of Agriculture BioAmber also offers bio-succinic acid derivatives, such as modified polybutylene succinate (mPBS) and 1,4 butanediol (BDO) BioAmber operates the worlds large-scale bio-based succinic acid production facility located in France Strategy partnership & development LANXESS and BioAmber have a partnership to develop succinic acid-based plasticizers that are both renewable and phthalate-free BioAmber has been chosen by PTT MCC to exclusively supply bio-succinic acid for their new 20,000 MT polybutylene succinate (PBS) plant, which is expected to start operating in 2014 Bioamber and Sinoven Biopolymers Inc. have signed a supply agreement for bio-based succinic acid. Under the terms of the agreement, Bioamber will be Sinoven's exclusive supplier of bio-based succinic acid, enabling Sinoven to produce renewable modified PBS BioAmber signed agreement with Mitsui & Co. Mitsui will provide know-how regarding shipping and logistics, warehousing, credit checks, freight insurance, and trade finance globally and facilitate sales in Asia Partnership with Cargill for developing a new generation microorganism to produce bio-based succinic acid used by Cargills technology BioAmber has licensed a technology from DuPont to to convert its bio-based succinic acid to bio-BDO Partnership with Evonik - long term cooperation for the development and manufacturing of catalysts for making BDO, THF and GBL from bio- based succinic acid Technologies process uses renewable and bio-based feedstock such as glucose or sucrose fermentation process, which uses aE. coli bacterium technology also has a lower carbon footprint as it uses carbon dioxide Capacity bio-based succinic acid plant located in Pomacle, France with a current capacity of approximately 3,000 MTPA Production Current output: 3000 MTPA SUCCINIC ACID Top producers of bio-based succinic acid. BioAmber Inc. Key Facts 31. west|east|transfer 12/2012 31 Description American company headquarterd in Quincy, Massachusetts offers broad pipeline of bio-based chemicals including succinic acid, lactic acid, acrylic acid, muconic acid and fumaric acid was awarded $50 million by US Department of Energy and $25 million by US Departnemt of Agriculture B&I program to help build asuccinic plant in USA Strategy partnership & development Myriant has signed an agreement with Japan based Sojitz Corporation for the creation of a sales and marketing partnership to distribute bio-based succinic acid in Japan, China, South Korea and Taiwan Showa Denko has partnered with Myriant for the supply of bio-based succinic acid for their PBS Agreement with Davy Process Technology for the integration of its bio-based succinic acid process with the Davy butanediol process for making bio-based butanediol. Agreement withChina National BlueStar for exclusive supply of bio-based suiccinic acid to BlueStar. The Chinese company is a BDO licensee of Davy Technology. A joint venture with Thailand-based PTT Chemical for deploying Myriant's technology in Southeast Asia. Supply agreement with Piedmont Chemical Industries and The Chemical Company to supply both companies with 100% of their requirements for succinic acid, with a target volume of 2,500 MT annually for each. Technologies apply its proprietary technology platform to develop renewable chemicals utilizing low-cost sugars use non-food feedstocks core capabilities include biomass pretreatment, genetic engineering, fermentation, separations/purification and scale-up Capacity 13,600 MT of bio-based succinic acid annually produces in the flagship facility in Lake Providence, Louisiana (start-up in 2013) Production Current output: producing of bio-based succinic acid has not started yet SUCCINIC ACID Top producers of bio-based succinic acid. Myriant Key Facts 32. west|east|transfer 12/2012 32 SUCCINIC ACID Top producers of bio-based succinic acid. REVERDIA (DSM ROQUETTE) Description Reverdia is a joint venture between DSM, the global Life Sciences and Materials Sciences company, and Roquette Frres, the global starch and starch-derivatives company Reverdia produces and sells Biosuccinium, the companys registered brand of bio-based succinic acid.The product is aiming at possible applications such as polyester polyols for polyurethanes, polybutylene succinate (PBS), plasticisers, 1.4- butanediol (BDO) Strategy partnership & development The company are now finishing with construction of a new plant located in Cassano Spinola, Italy. The plant will be its first commercial bio-succinic acid with expecting to have an annual capacity of 10,000 MT. The new production facility will for the time being use starch derivatives as feedstock. In the longer term the aspiration is to switch to second generation feedstock (cellulosic biomass) Key Facts Technologies production through fermentation of renewable resources Reverdia, with strong expertise in fermentation, recovery and plant scale- up, is the only company using low pH yeast technology rather than bacteria to produce bio-based succinic acid. low pH yeast-based production system using currently available agricultural feedstocks with plans to implement technologies using lignocellulosic feedstocks, Capacity Demonstrational bio-based succinic acid plant located in Lestrem, France with a capacity of 500 MT Production Current output: testing quantities 300 MT, non-commercial yet 33. west|east|transfer 12/2012 33 SUCCINIC ACID Top producers of bio-based succinic acid. SUCCINITY (BASF PURAC) Description BASF is the worlds leading chemical company Its portfolio ranges from chemicals, plastics, performance products and agricultural products to oil and gas BASF offers aslo succinic acid and its derivatives, such as including 1,4- butanediol (BDO), tetrahydrofuran (THF), polybutylene succinate (PBS), gamma- butyrolactone (GBL), and pyrrolidones. Purac, a subsidiary of CSM, is the leading company in fermentation and biotechnology Strategy partnership & development BASF has partnered with Purac, to form a joint venture, called Succinity, for the production of bio-based succinic acid.Purac is a Dutch company, focused on lactic acid production, green chemicals and biobased monomers for PLA. Part of CSM nv. Collaboration between the two companies since 2009, cooperation in bio succinic acid announced in 2011. The companies are planning a world-scale plant with a capacity of 50,000 MT although no timeline has yet been announced for this project. Key Facts Technologies highly efficient manufacturing process based on a proprietary microorganism, Basfia succinicproducens, a natural producer of succinic acid that can process a range of cellulosic and hemicellulosic sugars contained in biomass. Capacity 25,000-ton capacity fermentation production plant near Barcelona, Spain, with the intention to commercial start up by 2013 at the latest Production Current output: testing quantities 500 MT, non-commercial yet 34. west|east|transfer 12/2012 34 General information 2,5 - FDCA is a chemical intermediate that was identified by the U.S. Department of Energy's biomass program as a top 12 Top Value Added Chemicals. Valuable as an intermediate for pharmaceuticals, agrochemicals, insecticides, antibacterial agents, fragrances and so forth. It can substitute for terephthalic acid (TPA) in the production of polyesters and other current polymers containing an aromatic moiety Other 2,5-Furandicarboxylic acid consumers uses: Halogen substitution reactions In preparation of fibers and membranes In Pharmacology As Ingredient of fire foams Appearance: white powder 2,5-FURANDICARBOXYLIC ACID Key facts. Production routes FDCA is commercially (industrially) not yet produced. The production is only in small quantities because: The preparation of HMF (Hydroxymethylfurfural), the base in production FDCA - expensive By oxidation of HMF in production of FDCA a lot of by products, expensive purification Need of expensive solvents and catalysts to reach a good yield There were discovered and tested several ways of production of FDCA in mild conditions, which are declared to be applicable. The synthesis of FDCA directly from fructose could be an interesting rout (rout reported in 2003) Avantium economically feasible new route new catalytic based technology minimizing the water content without using exotic solvents in production of MMF (stable derivate of HMF) Extremely high potential platform chemical especially for production of polyesters and polymers as substitute for TPA Several ways of production of FDCA from HMF in mild conditions tested problem still the economically effective production of HMF AVANTIUM - a different manufacturing process than the traditional pursued routes towards HMF (YXY) HO O OH O O 35. west|east|transfer 12/2012 35 2,5-FURANDICARBOXYLIC ACID Production chain. As a feedstock for production FDCA are biomass based hexoses (glucose, fructose, manose) In applications can be used as a substitute for TPA, Isophtalic acid, adipic acid, bispenol A or phtalic anhydride or in pharmaceutics With substitution of alcohol components in production of polymers with derivates of HMF - 100% Biomass derived furan polymers BUILDING BLOCK MARKETS Biomass / sugar (C6) 2,5 - FDCA Substitutution of: TPA, Isophtalic acid, Adipic acid, BPA, PA Partially biomass deriven furan based polymers HMF (5Hydroxy methylfurf ural) PRE INTERMEDIATE 2,5 - Dihydroximethylfuran 2,5 bis (Hydroximethyl) tetrahydrofuran 100% Biomass derived furan polymers CHEMICAL TRANSFORMATION Polyesters Polyurethanes Plasticizers Avantium MMF (methoxy methylfurf ural ) Solvents Thermosets/ Resins Polyamides FEEDSTOCK 36. west|east|transfer 12/2012 36 Description Netherlander company - spin-out from Royal Dutch Shell in 2000 headquarters in Amsterdam, the Netherlands Specialized innovations and technologies for catalytic services and systems for creation of commercial Furanics In-hose development program for green polymers and green fuels Listed for two consecutive years as a global top 100 cleantech company Number of employees: 120 Strategy partnership & development in field of chemical products (not bio fuel) Strategic Cooperation: Cargill: Avantium teamed with NatureWorks (Cargill subsidiary) to help commercialize its furanics and for access to starch-based sources such as syrups. In 2011 Avantium acquired Jeff Kolstad who comercionalized PLA in NatureWorks. Cooperation in end uses agreements on testing, and commertionalization: Polyesters: Coca Cola: plant bottle production polyethylene2,5 furandicarboxylate (PEF) bottles to replace PET Danone: production of PEF instead of PET Polyamides: Tejin Aramid: production of aromatic polyamides (aramides) yxy based para-aramid fibers Solvay: production of engineering plastics polyamides Rhodia: production of polyamides in automotive, consumer goods and electronics Strategic goal of Avantium: to license yxy technology to the world Key Facts Technologies Catalytic way of production of methoxymethyl furfural (MMF) as a stable alternative to HMF and its oxidation to 2,5 FDCA. An efficient catalytic conversion process 100% carbon efficiency in the sugar dehydration More economic oxidation (under milder conditions) For now using 1st generation sugars and starch crops. Brand name for produced furanics - yxy Capacity 30mil. Investment into furanics production Yxy pilot plant in Chemelot (NL) 40 t/y (2011) Industrial plant 30.000 50.000 t/y (2016) Avantium owned Commercial plants 300.000 500.000 t/y (2020) - license based 2,5-FURANDICARBOXYLIC ACID Top producers of 2,5-furandicarboxylic acid. Avantium 37. west|east|transfer 12/2012 37 www.weastra.com