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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

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DE

weastra s.r.o | Tallerova 4 | 811 02 Bratislava | Slovakia | www.weastra.com | [email protected]

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!

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Weastra’s market reports and market analysis documents are tailor-made publications for weastra´s 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.

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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


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


HO ITACONIC ACID

HO O

OH O

CH2


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)


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 market

CHELATING 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-

ABSORBENTS

LATEX

"  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


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


SUCCINIC ACID HO O

OH O


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


SUCCINIC ACID Market mechanism.

FEEDSTOCKS

CONVERSION

SUCCINIC ACID

(processing)

CHEMICAL

TRANSFORMATION

MARKETS

Access to

feedstock

New generation

organism

Converting

technologies Distribution


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


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


316

92

82

51

37

21

BDO

Existing market

PBS, PBST

Polyester polyols

Plasticizers

Alkyd resins


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


2,5-FURAN- DICARBOXYLIC ACID

HO

O

OH O

O


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


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

PLASTICISERS

POLYURETHANES

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


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


! 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


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



KEY LEARNINGS


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 a!small part of petroleum based market (e.g. 10% of TPA) will take at least 10 years

END USES

FEEDSTOCK

POTENTIAL vs CAPACITIES


BACKUP


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


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


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


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 Frères 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 "  DSM’s 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.



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.


"  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.



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 company’s first commercial product line, Itaconix® DSP™, are water-soluble polymers used in detergents and cleaners based on its chelation and dispersion properties.


"  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


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 1970’s 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


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


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


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: BioAmber

Sarnia, 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: Uhde%Inventa+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: China%Na9onal%BlueStar%USA 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


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 world’s large-scale bio-based succinic acid production facility located in France


"  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 Cargill’s 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 a!E. 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


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 a!succinic plant in USA


"  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 with!China 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


Myriant Key Facts



REVERDIA (DSM – ROQUETTE) Description

"  Reverdia is a joint venture between DSM, the global Life Sciences and Materials Sciences company, and Roquette Frères, the global starch and starch-derivatives company

"  Reverdia produces and sells Biosuccinium™, the company’s 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)


"  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



SUCCINITY (BASF – PURAC) Description

"  BASF is the world’s 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


"  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


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


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 (5Hydroxymethylfurf

ural)

PRE – INTERMEDIATE

2,5 - Dihydroximethylfuran 2,5 – bis (Hydroximethyl)

tetrahydrofuran

100% Biomass derived furan

polymers


Polyesters

Polyurethanes

Plasticizers

Avantium

MMF (methoxy

methylfurfural )

Solvents

Thermosets/ Resins

Polyamides

FEEDSTOCK


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

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