Renewable Biosynthetic Terpenes for Use as High Performance Fuels Presentation at ABLC-Next San Francisco, CA November 11,

Allylix Corporate Sketch Privately held industrial biotechnology company formed in 2004 based on terpene synthase research from Salk Institute and Univ. of Kentucky. Currently employ 34 full-time staff in Lexington & San Diego We focus on the production of terpenes using our proprietary yeast-based fermentation technology Terpenes are ubiquitous in nature – over 50,000 identified – Multicyclic, multichiral compounds difficult and expensive to make using synthetic organic chemistry methods – Low natural abundance makes them expensive to extract Allylix has two terpene products on market – initial focus is on flavor and fragrance applications – Nootkatone – grapefruit flavor / fragrance – Valencene – orange flavor / fragrance Three pipeline products 2 Nootkatone

Current Situation: Gov’t Use of Renewable Fuels Several goals & initiatives passed by armed forces & Obama administration driving adoption of renewable fuels: – “Great Green Fleet” – biofuels to comprise up to 50% of the fuel used by a carrier strike group (including aircraft) in 2016 – “Green Fleet Initiative” – by 2015 all new vehicles purchased for America’s federal agencies will be electric, gas-electric hybrid, or use alternate fuels Most renewable fuels are composed solely of linear and branched chain hydrocarbons. This results in fuels with densities lower than petroleum-derived fuels currently used for jet, missile, and UAV propulsion. Numerous gaps exist in the development of high performance renewable fuels – High performance fuels can be used as specialized tactical fuels or additives to existing fuels to improve key performance properties including net heat of combustion, density, and potentially other important physical properties. 3

Key Physical Properties for High Performance Tactical Fuels Amount of energy produced when fuel is combusted (BTU / Gallon) Amount of energy produced when fuel is combusted (BTU / Gallon) Net Heat of Combustion (NHOC) Density Cetane Number Viscosity at low temps Freezing Point Higher is Better Example JP-5: 125,000 JP-10: 141,500 Example JP-5: 125,000 JP-10: 141,500 Higher density means more fuel per given volume (gram / ml) Higher density means more fuel per given volume (gram / ml) Higher is Better Example JP-5: 0.81 SPK*: 0.75 Example JP-5: 0.81 SPK*: 0.75 Fuels must be liquid at low temps found at high altitude (Degrees Kelvin) Fuels must be liquid at low temps found at high altitude (Degrees Kelvin) Lower is Better Examples JP-5: 226 water: 273 Examples JP-5: 226 water: 273 A measure of combustion speed of a fuel. High cetane = shorter ignition delay Higher is Better Examples Diesel #2 & F-76 ^ both Examples Diesel #2 & F-76 ^ both Many liquids become highly viscous at low temperature (centistoke) Many liquids become highly viscous at low temperature (centistoke) Lower is Better Example JP-5: <8.5 cSt at -20 C Example JP-5: <8.5 cSt at -20 C * Bio-derived Synthetic Paraffinic Kerosene – current SOA renewable jet fuel ^ F-76 is Navy marine diesel fuel

5 Structure/Property Relationships for Representative C10 Hydrocarbon Fuels 5 Straight Chain: high cetane number but higher melting point (good for diesel fuel) Branched Chain: low cetane number with low melting point (jet fuel) Cyclic: moderate cetane number, high density, low melting point (jet/diesel/HD tactical fuel) Aromatic: high density, but low cetane number, high melting point, and incomplete combustion (particle formation) - unsuitable in high concentrations Petroleum derived fuels contain complex mixtures of the four classes of hydrocarbons shown above. Most renewable fuels are composed of either straight or branched chain hydrocarbons. In contrast, Allylix targets multi-cyclic hydrocarbons that can be used for a wide variety of applications.

6 Renewable Fuels that Outperform Petroleum? High density renewable fuels will allow for increased range and/or operational time for a host of tactical vehicles (UAVs) and weapon platforms

NAWCWD and Allylix Evaluation of Sesquiterpenes Under ARPA-E Award NAWCWD (China Lake, CA) approached Allylix in 2011 to evaluate Allylix sesquiterpenes as new high density fuels that could potentially replace JP-10 and be used in a wide variety of weapon platforms. JP-10 is current “gold standard” high performance fuel made from petrochemical sources. In Summer 2012 Allylix submitted a proposal to ARPA-e requesting support for the creation, testing and development of additional sesquiterpenes as high performance fuels using Allylix’s proprietary technology. Allylix’s proposal was one of only 66 selected for funding out of thousands submitted, and initial results from this work are very promising. 7

8 First-Generation Sesquiterpene Fuels Selected Properties of Pure Sesquiterpane Fuels Benchmarks PropertiesFuel #1Fuel #2Fuel #3Diesel #2Jet A Density (g/cc) NHOC (btu/gal) 135,386135,564132, ,000125, °C Viscosity (cSt) N/A< °C Viscosity (cSt) <4.1 Cetane No >41 Harvey, B. G.*; Meylemans, H. A.; Gough, R. V.; Quintana, R. L.; Garrison, M. D.; Bruno, T. J. Phys Chem Chem Phys 2014, 16,

Net Heat of Combustion (btu/gal) for Common and High Density Fuels 9

10 Net Heat of Combustion of Sesquiterpene Fuels Exceed those of “Gold Standard” JP-10 Fuel Density (g/mL) NHOC (Btu/gal) Flash Point (°C) -20°C Viscosity (cP) 40 °C Viscosity (cP) A , B , C , D , E , F , JP ,546 55<10cSt (-18 °C)N/A JP-5~0.81~125,000>60<8.5 cSt (-20 °C)N/A Allylix and NAWCWD are developing the highest density renewable fuels ever studied.

11 Allylix Technology Capable of Creating “Designer” Biosynthetic Fuels Sesquiterpene structure has dramatic impact on fuel properties Small Changes in Fuel Structure Significant Change in Fuel Properties Primary or secondary derivatives (via enzymatic biosynthesis) Catalytic isomerization Beta-caryophyllene Density Viscosity Cetane # The combination of fermentation-based terpene production and chemical catalysis allows for the generation of “designer” high-performance fuels Harvey, B. G.*; Meylemans, H. A.; Gough, R. V.; Quintana, R. L.; Garrison, M. D.; Bruno, T. J. Phys Chem Chem Phys 2014, 16,

12 Example: Isomers or Derivatives of Parent Terpene Provides Significant Changes in Viscosity Isomerization Primary / secondary derivatives via catalysis Use of fuel blends

Summary of Key Criteria for High Performance Fuels JP-10 NHOC (>140,000 btu / gal) Cetane number >40 Low Freezing Point (<225 K) Low Viscosity at Low Temps High Density (>0.9 g/cc) Straight Chain HC Branch Chain HC Aromatic HC Allylix C15 HC

Fuels produced by Allylix & NAWCWD under the ARPA-e program will offer several advantages to the US military: – A renewable, high-quality, cost effective, reliable and sustainable supply of high performance fuel that can outperform the current gold standard, petrochemical JP-10 – Potential to increase range and/or operational time for a host of tactical vehicles (UAVs) and other weapon platforms Even a 10% increase in range is a substantial advantage for our military forces Additional uses / benefits: – Rocket Fuels: Potential to out-perform gold standard rocket fuel, RP-1. The Isp values of Allylix sesquiterpenes are similar to RP-1, but with higher densities, which translates into either longer range, or reduced fuel volumes. – Terpenes developed as fuels may also be used for other government needs (e.g. biocides and insect control). 14 Numerous Benefits Associated with This Program

Renewable Biosynthetic Terpenes for Use as High Performance Fuels Presentation at ABLC-Next San Francisco, CA November 11,