The Evolution of BiobutanolThe Evolution of Biobutanol(Part 1)(Part 1)

BDC Spring SymposiumApril 8, 2014

James Evangelow, PresidentChemical Strategies

Email: jevangelow@chemstrategies.com

Chemical Strategies 77 New Broadway Sleepy Hollow, NY 10591 PH: (914) 524-9764

Is biobutanol the nextIs biobutanol the nextethanol?ethanol?Is biobutanol the nextIs biobutanol the nextethanol?ethanol?

AGENDAAGENDA

Will history repeat itself? Synergy with ethanol Focus: chemical & solvent Sam Nejame will discuss fuel

Carter was the President Period of “oil shocks”; supply concerns Rising energy prices Iran takes US hostages Environmental concerns lead to recent

introduction of catalytic converters on cars &unleaded gasoline

Automakers strive to improve MPG US produces ~200MM Gal/Yr ethanol from

ethylene for solvent & chemical uses. US industry starts making renewable ethanol

from corn for gasoline blending ("Gasohol”)but also for petro-ethanol markets.

Go back in time to the late 1970’s:Go back in time to the late 1970’s:

Carter was the President Period of “oil shocks”; supply concerns Rising energy prices Iran takes US hostages Environmental concerns lead to recent

introduction of catalytic converters on cars &unleaded gasoline

Automakers strive to improve MPG US produces ~200MM Gal/Yr ethanol from

ethylene for solvent & chemical uses. US industry starts making renewable ethanol

from corn for gasoline blending ("Gasohol”)but also for petro-ethanol markets.

Obama is President Costly oil & gasoline Political instability continues in the Middle East However, increased North American energy

production has reduced supply disruption fears Environmental efforts to lower GHG Automakers strive to improve MPG US produces 350MM Gal/Yr butanol from

propylene for solvent & chemical uses Ethanol hitting the “blend ceiling” US biobutanol industry beginning to emerge as

the superior next gen biofuel; aim to produce inretrofitted ethanol plants

However, petro-butanol markets in solvents &chemicals are lucrative initial targets.

Today………….Today………….

Obama is President Costly oil & gasoline Political instability continues in the Middle East However, increased North American energy

production has reduced supply disruption fears Environmental efforts to lower GHG Automakers strive to improve MPG US produces 350MM Gal/Yr butanol from

propylene for solvent & chemical uses Ethanol hitting the “blend ceiling” US biobutanol industry beginning to emerge as

the superior next gen biofuel; aim to produce inretrofitted ethanol plants

However, petro-butanol markets in solvents &chemicals are lucrative initial targets.

Four isomers: n-, iso, sec- & tert n-Butanol & isobutanol are the

commercially significant oxo alcohols Both are produced from butyraldehydes,

which are generated via the oxo reactionof syngas with propylene Mainly used to make solvents and

polymers for: paints, coatings, adhesives,inks, caulks & sealants Sell for $5-$10/Gal in industrial uses Far superior to ethanol as a fuel

Meet theMeet the ButanolsButanols………………

Four isomers: n-, iso, sec- & tert n-Butanol & isobutanol are the

commercially significant oxo alcohols Both are produced from butyraldehydes,

which are generated via the oxo reactionof syngas with propylene Mainly used to make solvents and

polymers for: paints, coatings, adhesives,inks, caulks & sealants Sell for $5-$10/Gal in industrial uses Far superior to ethanol as a fuel

US n-Butanol Demand US Isobutanol Demand

Acrylate32%

GlycolEthers22%

Acetate11%

Resins10%

Solvent7%

Other4%

Exports47%

2013

NN--ButanolButanol is the “big brother”is the “big brother”

Acetate11%

Solvent5%

Plasticizer1%

AminoResins

1%

Other1%

Exports24%

Total: 320 MM Gal

Lubes18%Acetate

14%

Resins10%

Total: 25 MM Gal

4,000

6,000

8,000

10,000

12,000

14,000

16,000

Million Gallons

US Ethanol Demand

Fueling growth!................Fueling growth!................

0

2,000

4,000

1975 1980 1985 1990 1995 2000 2013

Chemical Solvent Beverage Export Fuel

US Industrial Ethanol Demand, 2013

Vinegar28%

Acetate11%

GlycolEthers

4%

Other15%

Chemicals

CleaningProducts

23%

Paints,Coatings

, Inks19% Process

Solvent9%

Solvents

They’re still living?They’re still living?

Acrylate26%

Amines16%

Acetate11%

Total: 110 MM Gal

PersonalCare45%

ProcessSolvent

9%Drugs2%Other2%

Total: 120 MM Gal

Alive, but turning “green”Alive, but turning “green”

Trait Ethanol ButanolFamily origin Ethylene PropyleneRecent move Bio-based Bio-based*Jobs Chemicals & Solvents

Such as Ethyl acrylate Butyl acrylateEthyl acetate Butyl acetateCoatings, inks Coatings, inksFuel Fuel

DNA 2 Carbons 4 CarbonsOther Cheap Energy denseWorldwide 1.6 Billion Gal** 1.6 billion Gal

* Just beginning the journey.** Industrial

Long lost relatives…….Long lost relatives…….

Trait Ethanol ButanolFamily origin Ethylene PropyleneRecent move Bio-based Bio-based*Jobs Chemicals & Solvents

Such as Ethyl acrylate Butyl acrylateEthyl acetate Butyl acetateCoatings, inks Coatings, inksFuel Fuel

DNA 2 Carbons 4 CarbonsOther Cheap Energy denseWorldwide 1.6 Billion Gal** 1.6 billion Gal

* Just beginning the journey.** Industrial

Significant Biobutanol Technology Providers

n-Butanol - Green Biologics, Cobalt(bacteria) Technologies, Eastman,

Cathay

Isobutanol - Butamax, Gevo(yeast)

Where doWhere do biobutanolsbiobutanols come from?come from?

Significant Biobutanol Technology Providers

n-Butanol - Green Biologics, Cobalt(bacteria) Technologies, Eastman,

Cathay

Isobutanol - Butamax, Gevo(yeast)

2

4

6

8

10

7.02

4.07

6.957.94

6.65 6.896.59

4.40

7.208.59

8.028.95

3.252.35 2.78

3.52 3.6 3.51

Average US Market PriceUSD per Gallon

Where are theWhere are the biobutanolsbiobutanols going?going?

0

2

2008 2009 2010 2011 2012 2013

n-Butanol, Industrial Isobutanol, IndustrialRegular Gas, Retail

ETHANOLBIOBUTANOL

Will history repeat itself?Will history repeat itself?