production of highly pure fatty acids from anaerobic … granda...production of highly pure fatty...

Earth Energy Renewables © 2015 1

Production of Highly PureFatty Acids from

Anaerobic Digestion

Breakout Session – Track 6

Cesar B. Granda, Ph.D.Chief Technology OfficerEarth Energy RenewablesBryan, TX

Disclaimer

NOT FOR REPRINT, PUBLICATION OR DISTRIBUTION

THIS IS NOT A SOLICITATION OR OFFER TO SELL SECURITIES.

THIS PRESENTATION CONTAINS ESTIMATES, FORECASTS, AND PREDICTIONS OF ANTICIPATED

FUTURE PERFORMANCE THAT ARE FORWARD LOOKING. NO ASSURANCE CAN BE GIVEN AS TO

THEIR ACCURACY. NO INVESTMENT DECISION SHOULD BE BASED UPON THIS PRESENTATION.

July, 2015

PRIVILEGED & CONFIDENTIAL INFORMATION

2


Thesis:

“We make cheap fatty acids from any

biodegradable material”

Earth Energy Renewables

Feedstock

flexible

State-of-the-art laboratory,

pilot and 100,000 GPY Demo

Plant

Chemicals

Earth Energy Renewables © 2015

• Demonstrated success creating high-margin green chemicals

• Low-cost alternative to petroleum-based chemicals

• High-value solution to organic waste stream disposal

• Stair-step scale up – Profitable at every scale-up stage

• Opportunistic acquisition of assets and IP from Terrabon, Inc

4

Anaerobic digestion

8

Promote fatty acids – Acetic, propionic, butyric, etc. – From C2 to C8 –

a.k.a short- and medium-chain fatty acids by inhibiting methanogenesis

Biomass

Hydrolysis

Acidogenesis

Methanogenesis

CH4, CO2

Cellulose, hemicellulose, starch, pectin, proteins, fats

Free sugars, amino acids, long-chain fatty acids, glycerol

Short- and medium-chain fatty acids, NH3, CO2, H2S


Where does this occur in nature?

8Earth Energy Renewables © 2015

•Sugarcane molasses

•Sorghum stalks

•Municipal sewage sludge

•Cellulosic municipal solid waste

•Bio-sludge (from chemical plant

WWTP)

•Chicken manure

•Cattle manure

•Sugar beet pulp

•Lipid-extracted micro-algae

•Whole micro-algae

•Pulp-mill molasses (wood molasses)

•Orange peels

•Oil Palm empty fruit bunch

•Palm oil mill effluent

Feedstock Flexible = Globally Replicable

•Alfalfa

•Food wastes

•White office paper

•Paper-mill fines

•Sugarcane bagasse

•Pineapple waste

•Glycerol

•Raw Glycerin

•Corn Stover

•Rice Straw

•Cotton gin trash

•Water hyacinth

•Switchgrass

•MSW-Wet organics

•Poplar Wood

Over 30 FeedstocksTested


Lowering Risk for Successful Commercialization

De-risking technology through incremental scale-up: integrated pilot, 8TPD, 30TPD

Key Challenges

Biomass Conversion Product: 2015-16 Scale up: 2017

Suitable material

Reliable supply Affordable delivery

Feedstock handling

Product Yields Anaerobic digestion

Recovery

Separations

Impurities

Benchmarking

Recycle loops

Cash flow-positivePartners, supply/off-take

EPC

Adaptable design for

fast deployment 8

Feedstock

Preparation

Water

Excess

Potable

Water

Purified

Fatty

Acids

Ammonia and

Phosphate

Recycle of short-chain fatty acids for elongation

De-risking technology through incremental scale-up: integrated pilot, 8TPD, 30TPD

Anaerobic

DigestionClarification Concentration

Acidification/

ExtractionFractionation

Sludge


Typical Acid Spectrum

C2 – C8 Carboxylic Acids

C2 Acetic

C3 Propionic

iC4 Iso-butyric

C4 Butyric

iC5 Iso-valeric

C5 Pentanoic (Valeric)

C6 Hexanoic (Caproic)

C7 Heptanoic (Enanthic)

C8 Octanoic (Caprylic)

The final product acid spectrum can be controlled by modifying operating

conditions. C2 recycled to continue elongation 9Earth Energy Renewables © 2015

• Simple, efficient, and effective

• No extraneous extractant

Advantages of EER’s process

• Produces very pure acids without complex

and expensive purification techniques

• Nitrogen, sulfur and metals content in acids is

low

• Thermodynamically favored

• Non-sterile process

• Natural cultures; no GMOs

• Very Robust

• Very inexpensive

• No extraneous enzymes

• Feedstock agnostic

• High yields, >0.65 ton acid/ton feed theoretical

(>130 gal EthOH equivalent/ton feed or

> 87 gal gasoline equivalent/ton feed)

Extraction

Anaerobic Digestion


Saturated

Dicarboxylic

Acids

Unsaturated

Dicarboxylic

Acids

Unsaturated

Carboxylic

Acids

Fatty

Acids

Dienes

Product Pathways

Carboxylic Acids – Chemical Building Blocks

11

Fatty

Acid SaltsEsters

Primary

Alcohols

Ketones

Secondary

Alcohols

Di-ketone

AlcoholsDiols

Gasoline/jet

Fuel/Diesel

Biological

Conversion

Chemical Conversion

ORGANIC

MATTER

Olefins


Demonstration Plant

6150 Mumford Rd.,

Bryan, TX

• Field Scale

• Demonstration and Pilot scale operations of

process

• Indoor & outdoor operations

• Extensive laboratory capabilities

• 17,000+ hours of operation

(fermentation/clarification)Earth Energy/Confidential & Proprietary

12

0.0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.00

10

20

30

40

50

60

70

Yie

ld (

ton

of

acid

s/to

n o

f fe

ed

)

Time (weeks)

13

Demonstration Plant Yield Data at 3 ton/day(72 weeks = 12,072 hours of operation)


Significant Low Cost Producer Advantage

*Cash manufacturing cost at 90 dry ton/day scale excluding depreciation Earth Energy Confidential and proprietary

14

Medium-Chain Fatty Acids – Large Established Markets

C3 Propionic Acid

C4 Butyric Acid

C5 Valeric Acid

C6 Caproic Acid

C7 Heptanoic Acid

C8 Caprylic Acid

Animal Feed Supplements

Grain Preservative

Food Preservative

Herbicide

Pharmaceuticals

Cellulose Acetate

Butyrate Propionate

(CAB/CAP)

Flavor & Fragrance

Neopolyolesters (NPE)

Polyethylene/Propylene

Glycol (PEG/PG) Esters

Resins

Rheology

Modifiers

Coatings

(Automotive)

Lubricants

Emulsifiers

Thickeners

Resin Plasticizers

Viscosity Control

Wetting Agent

Emolients


Derivatives Applications and Markets

16

Pilot Plant

30 kg/day Feed

8 tons/day Feed

30 tons/day Feed

50 ton/day Feed

90 ton/day Feed

Plant Feed Capacity on a dry basis

280 ton/day Feed

1000 ton/day Feed

Acids

(food-grade)Acids Esters Primary

AlcoholsHydrocarbon

Fuels

Hydrocarbon

Fuels

Nth Plant

$10 - $100/galC3 Propionic

C4 Butyric

C5 Valeric

C6 Caproic

C7 Heptanoic

C8 Caprylic

CA

PE

X

$6 - $15/galPropionate

Butyrate

Valerate

Caproate

Heptanoate

Octanoate

$5 - $9/galn-Propanol

n-Butanol

n-Pentanol

n-Hexanol

n-Heptanol

n-Octanol

$4.50/gal

Profitable at Each Stage of Engineering Scale-up

* With RINsExcept for pilot plant,

all cases have a

positive return with

< 3 year payback

Demo plant

expansion

Product Range of Business Plan: C3–C8 Acids, Esters & Primary Alcohols


Commodity Chemicals

Food production

waste stream

8 TPD – 2017

Corn and Soy meal

Molasses From market

30 TPD – 2019

FEEDSTOCK OFF-TAKE

Flavors & Fragrances

18

Deployment StrategyNon-GMO, US and EU Compliant

Natural Chemicals


ProductFatty Acids

(flavor & fragrance)

Commercial Demo

Plant

Fatty Acids

(Ag and Industrial)

Feed Input, dry tons/day 8 short tons/day 30 short tons/day

CAPEX < $10 million <$25 million

Feedstock Cost, $/dry ton $2001 $0.0

Variable Cost OPEX, $/ton $289/short ton of feed $89/short ton of feed

ROI based on EBITDA 50.4% 43.0%

Payback time based on EBITDA 2.0 years 2.3 years

Production cost (no depr) , $/kg $1.85/kg $0.716/kg

1 Selected feedstock from market for natural, food-grade and kosher qualifications

Economic SnapshotFlavor & Fragrance grade

Ag and industrial grade (commodity)


Sustainable Platform

for the Chemical Industry

in the 21st Century

• Fatty Acids Hundreds of other Chemicals

• Renewable Wet or Dry Organic Feedstocks

• Green EU/US Natural Bio-Based Chemicals

• Highly profitable



“Simplicity is the ultimate sophistication” Leonardo Da Vinci

production of highly pure fatty acids from anaerobic … granda...production of highly pure fatty...

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