Bringing Novel, Bio‐based Chemicals to Market: Strategies, Applications & Lessons Learned

Next Generation Bio Based Chemcials Molecules to Markets January 29, 2013

Not All Chemicals Are Created Equal™

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HIGHER PERFORMANCE

NON-FOOD BASED OPTION

NO GREEN PRICE PREMIUM

LOWER CARBON FOOTPRINT

Myriant’s DNA

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The Company • Formed in 2009; 150 Employees in 2012

• HQ in Quincy, MA

• 18,000 sq.ft. R&D lab in Woburn, MA

• Scale and Pilot Plant in Leuna, Germany

• Commercial Plant in Lake Providence, LA

Bio-Based Chemical Strategy • Convert Renewable Feedstocks to High Value Chemicals

• Focus on C3-C6 Chemicals

• Leverage Deep Biotech Experience to Further Pipeline

• Build-Own-Operate Model

• Strategic Partnerships to Accelerate Growth

Built by Myriant

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People • All Core Biotech R&D Conducted in House

• ~50 Professionals; ~50% with PhDs

Facilities / Processes • State-of-the-Art 18,000 Square Ft. Laboratory

• All Genetic Engineering Tools Available on Site

• Non-GMO Platform

• Significant Fermentation Optimization Capabilities

• Fully Integrated from Lab to Commercial Scale

Scaled with Partners

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D(-) Lactic Acid at 20,000L

Commercial Scale in 2008

Technology Proven

Commercial Yield Targets Maintained or Improved from

7L to 40L to 50,000L

Process Improves With Scale

Succinic Acid: Final Scale-Up Step Only 8x

COMMERCIAL SCALE PILOT PLANT SCALING R&D

Lake Providence Plant Online 1Q 2013

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• First Bio-Succinic Acid Plant in U.S.

• 30 MM lb / Year Commercial Plant in Lake Providence, Louisiana

• Commercial Start-Up Q1 2013

• 140 MM lb/Year Expansion Plans Underway

Succinic Acid – Our Engine for Market Acceleration

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Succinic Acid

Current Succinic Acid Applications

BDO Drop-in Applications i.e. Maleic Anhydride in BDO

Replacements for Adipic and Phthalic Anhydride

BUTANEDIOL

SOLVENTS

PLASTICIZERS

BIODEGRADABLE PLASTICS

URETHANES

Proven Chemistry Provides Access to High-Value Markets

The Case for Renewable Chemical Feedstocks: How Much Does

Your Carbon Cost?

Feedstock cost of finished product Historical feedstock pricing

Cost advantage

Crude oil is much more price volatile than biomass and is more expensive as a source of carbon for building molecules

WTI Crude

Dextrose

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Competitive Cost Advantage of Bio-based Succinic Acid

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CH3CH3

OOO

OHOH

O

O

O

OH

OH

OH

OH

OH

CH3

OH

O

O

OHOH

O

O

O

OHOH

O

O

OH

OHOH

O

O

Crude Oil

Corn

Butane (4C)

Maleic Anhydride (4C)

Succinic Acid (4C)

Glucose (6C)

Refinery Maleic Anhydride Plant

Cat. Vanadium Phosphorus Oxide Catalyst

400 °C, O2 (150 kPa)

CO2 Waste (Yield Loss)

Succinic Acid Plant

130 °C H2 (30 MPa) Catalyst

Wet Mill

Pyruvic acid (3C)

Oxaloacetic acid (4C)

Malic acid (4C)

Fumaric acid (4C)

37 °C, 1 atm.

CO2

(sequestered)

More expensive raw material and requires high temperature , pressure, and expensive catalyst and 2 plants

Cheaper raw materials, low temperature and pressure, 1 plant

Inside the cell

Continuum of Substitution

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Exact Substitute

Completely New Product

Easy Hard

Type of Substitution

Degree of Difficulty

Constraints

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• Product MUST work • Price, price, price •“Green” is insufficient to drive material replacement

The Landscape- “Green” Products Don’t Work

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• More expensive

• Poorer quality illumination

• Toxic for the environment

• but, you’re green if you use them………….

Constraints

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• Product MUST work

• WHAT IF… It does work? • Price, price, price

• WHAT IF… There is no price premium? •“Green” is insufficient to drive material replacement

• WHAT IF… It is “Greener” (renewable, smaller footprint)?

Example- Performance Chemicals

• Coalescing Solvents for Waterborne Paints

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How Coalescing Solvents Work

Coalescing solvents assist in the formation of a coherent film on a substrate from a dispersed water-borne coating formulation

Paint- Dispersed polymer particles and pigments in water

As-applied wet film

The particles approach and contact and begin to flow together with the help of the coalescing solvent

To make a dry film- Hard, tough polymer layer holding pigments in place

As water evaporates from the larger surface area of the applied film….

Myrifilm® Performance Equal to Industry Standard with Zero-VOCs

Gloss and Contrast Ratio Scaled to a Maximum Value of 10

10.49 lb/gal density, 33.97% solids in formulation. Dow Rhoplex SG-30 Binder resin (47.7 % w/w); 2.5 wt% coalescent relative to binder resin; TiO2 Pigment with final PVC 21.95. Based on Dow recommended formulation for this resin.

PropertySemi-Gloss Acrylic

with Myrifilm™

Semi-Gloss Acrylic

with Texanol

KU Viscosity (immed./24 h) 87.9/14.2 90.7/107.8

Sag 10.7 10

Leveling 4 4

Contrast ratio (Air-dry, 24h) 96.24 96.25

Gloss 20°/60°/85° 44.4/74.4/97.9 39.8/75.3/97.8

Block Resistance (120 °F, 24 h) 5 6

Scrub Resistance (2400 cycles) 8 8

Low Temperature Coalescing (40 °F,

10 mil)5 5

Tint Strength (Red) %TSUC 103.3 99.8

Tint Strength (Yellow) %TSUC 83.5 99.4

Tint Strength (Blue) %TSUC 101.4 100

VOC (ASTM D-6866) 0.5 18

0

2

4

6

8

10

12

Sag

Leveling

Normalized

Contrast Ratio

Normalized 60°

Gloss

Block Resistance

Scrub Resistance

Myrifilm™

Texanol

Myrifilm® Retains Performance at Lower Concentration

10.54 lb/gal density, 36.84 vol% solids in formulation. Orgal P885RR binder resin (38.9 % w/w); 2.5 wt% coalescent relative to binder resin; TiO2 Pigment with final PVC 34.09.

Myrifilm ® performs as well as Texanol at half the concentration

0

2

4

6

8

10

12

Normalized

contrast ratio

Normalized

60° Gloss

Normalized

85° Gloss

Sag

Leveling

Blocking

Myrifilm 50% loading

Texanol Standard

Dosage

Example- Polyurethanes

• Replacement for Adipic Acid in Polyester Polyols

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Succinic Acid in Urethanes

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• Succinic acid can be used in place of adipic acid to make polyurethanes with very good physical properties

• Replacement is straightforward- requires less modification to formulation than other “green” alternatives

• Same chemical functionality so fits into same processes and applications

• Provides a renewable alternative that works

O

OH

O

OH + OHO

OHn

OO

OHO

O

O

OOH

- H2O

OHOH

O

O

+ OHO

OH

- H2O

OO

OO

OH

OH

O

O

n

Succinic acid based polyester polyol

Adipic acid based polyester polyol

Higher Renewable Content That Works

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Up to 100% Renewable Content Available

Diacid DiolBio-based Carbon Content (wt%)

SACDEG (90)/PEG (10)/

TMP47

SACDEG (90)/PEG (10)/

TMP47

SAC EG 66

SACBDO (80)/MPD (20)

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SAC DEG 50

SAC HDO 40

SAC PDO 100

0

10

20

30

40

50

60

70

80

90

100

Shore A Hardness

Polyurethane Physical Properties

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Comparable Shore A Hardness across all compositions

Crystalline materials- increased hardness

Polyurethane Physical Properties

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Comparable Modulus across all compositions

Crystalline materials- increased stiffness

5239 12590

0

100

200

300

400

500

600

700

800

900

1000

Modulus (psi)

Example- Materials

• Plasticizer for Flexible PVC

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Succinate Esters as Phthalate-Free Plasticizer Alternatives

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OHOH

O

O

Succinic acid

O

O

O

Phthalic anhydride

2-EH

2-EH

Isononanol

Isodecanol

+

+

+

+

DOP

DOSX

DIDSX

DINSX

Dioctyl phthalate

Di-isononyl succinate

Di-isodecyl succinate

Dioctyl succinate

OHOH

O

OAdipic acid

2-EH + DOA

Dioctyl adipate

Plasticizer Efficiency at 50 phr

Plasticizer Shore A Shore D Tb (°C)

DOSX 84 35 -58

DINSX 91 34 -58

DIDSX 91 42 -50

DOA 84 35 -59

DOP 88 43 -30

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Tested according to ASTM D-2240 and D-746-07

Succinate ester plasticizers show efficiency and low temperature flexibility comparable to standard aliphatic plasticizers

Physical Properties After Oven Aging, 100 °C, 50% R.H.

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Tested according to ASTM D-1203-03 and D-638

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70

80

90

100

0 7 14 21

Sam

ple

Weig

ht

Aft

er

Agein

g,

% o

f In

itia

l W

eig

ht

Aging period, days, at 23 °C, 50 % R.H.

DOA 50 phr DOP 50 phr DOSX 50 phr DINSX 50 phr DIDSX 50 phr

0.0

10.0

20.0

30.0

40.0

50.0

60.0

70.0

0 7 14 21

Bre

ak S

tress

, M

Pa

Aging Period, days, 100 °C, 50% R.H.

DOA 50 phr

DOP 50 phr

DOSX 50 phr

DINSX 50 phr

DISX 50 phr

0

50

100

150

200

250

300

350

400

450

0 7 14 21

Bre

ak S

tarin, %

Aging Period, days, 100 °C, 50 % R.H.

DOA 50 phr

DOP 50 phr

DOSX 50 phr

DINSX 50 phr

DIDSX 50 phr

Weight Loss Break Stress Break Strain

Higher molecular weight succinate esters are less volatile and can retain physical properties better than dioctyl adipate under severe aging conditions

Succinic Acid in Renewable Performance Materials

OHOH

O

OSuccinic acid

OHOH

1,4-butanediol

PET copolymers for non-wovens and fibers

Polyesters for hot melt adhesives

Poly(butylene succinate) for flexible films and packaging

Ester plasticizers for vinyl compounds

Poly(butylene terephthalate) for engineering resins

Unsaturated Polyesters

Polyester polyols for polyurethanes and

TPUs

Polyester resins for coatings

PTMEG for elastic fibers

Transforming the Chemicals Industry

• Technical barriers to practical commercial supply and adoption of bio-based chemicals are falling quickly

• Commercial barriers to widespread adoption of bio-based chemicals including capital and supply chains for non-food feedstocks remain

• Market barriers get lower when a product performs well, has no green premium, and gives a smaller environmental footprint

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