Iowa State University Center for Catalysis DOE Products Platform Stage Gate Review Meeting August 9,

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Iowa State UniversityCenter for CatalysisDOE
Products Platform Stage Gate Review Meeting
August 9, 10, 2005

• Dr. Victor Lin
• Iowa State University

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Overall Project Goals Objectives

• The overall objective is to enable Iowa State
  University to establish a Center for Catalysis
  that enjoys world-class stature and enhances the
  Iowa and US economy through the transfer of
  innovation from the laboratory to the
  marketplace.

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Organization/Approach

• All funded projects are part of a soybean or corn
  biorefinery.
• Two funded projects have made significant
  progress toward goals of the MYTP draft document.
  
• 1. Catalysts to convert feedstocks with high
  fatty acid content to biodiesel
• 2. Conversion of Gylcerol into Propanediol

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Milestone Fit
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Task Objective Detail

• Project 1 - Catalysts to convert feedstocks with
  high fatty acid content to biodiesel
• Technical or economic target or objective to
  construct a catalytic system that will produce
  biodiesel from high free fatty acid-containing
  feedstocks without any pretreatment.
• Milestones established
• 1. Synthesis of materials with both general acids
  and bases.
• 2. Identification of optimal catalysts for
  biodiesel generation from soybean oil.
• 3. Functionalization of the exterior surface of
  the materials with catalytic groups for the
  esterification of free fatty acids.
• 4. Identification of optimal catalysts for making
  biodiesel from fat.
• 5. Investigation of recyclability of optimal
  catalysts.
• Go No/Go decision points
• 1. Is cost of optimal catalyst lower than
  homogeneous catalyst?

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Technical Barriers AddressedChemicals and
Materials
Transesterification
Oil
Glycerol
Biodiesel
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Technical Barriers AddressedChemicals and
Materials
J. A. Nieweg, C. Kern, H.-T. Chen, Y. Huang, and
V. S.-Y. Lin Angew. Chem. Int. Ed. 2005,
submitted.
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Technical Barriers AddressedChemicals and
Materials

• Transmission Electron Micrographs

Lai, C.-Y. Trewyn, B.G. Jeftinija, D.M.
Jeftinija, K. Xu, S. Jeftinija, S. Lin,
V.S.-Y. J. Am. Chem. Soc., 2003, 125, 4451-4459.
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Task Objective Detail

• Reaction completion in 26 hours at 25 C
  (unpurified poultry fat (100 mL) to biodiesel and
  glycerin)
• Recyclability 20 recycles without decrease in
  reactivity was observed (TON 3,340 for 15 days).

J. A. Nieweg, C. Kern, H.-T. Chen, Y. Huang, and
V. S.-Y. Lin Angew. Chem. Int. Ed. 2005,
submitted.
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Market Customers

• Customers biodiesel industry
• Range of production costs - NaOMe is 0.25 per
  pound. Our best catalyst has a cost of 0.30 per
  pound. The recyclability of our catalyst is over
  20 cycles
• Market dynamics Based on the patent literature,
  other heterogeneous catalysts are being developed
  by industry and academic labs. Esterfip-H
  employs heterogeneous catalyst technology to
  convert fatty acid methyl esters into biodiesel.

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Competitive Advantage

• Currently, biodiesel is prepared using
  homogeneous base catalysis. Cheaper feedstocks
  such as waste restaurant oils and rendered animal
  fats have a large amount of free fatty acids.
  Free fatty acids cannot be converted into
  biodiesel using base-mediated processes.
• Our catalyst system offers an integrated
  catalytic system that performs both
  esterification (of free fatty acids) and
  transesterification (of soybean oil) in a one-pot
  fashion. This will allow the biodiesel producers
  to use the cheap feedstocks without any
  pretreatment. In addition, the catalyst system is
  heterogeneous and is highly recyclable and
  reusable.

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Strategic Fit

• We have established a partnership with West
  Central Cooperative. West Central Cooperative has
  a state-of-the-art, 9,000 square foot facility
  that manufactures 12 million gallons of biodiesel
  annually, and is the largest biodiesel plant in
  the United States.
• They will work with us on the catalyst scale up
  and will evaluate our best catalyst on a pilot
  plant scale at their company.
• Fit with the Biomass Programs biorefinery
  pathway approach Fuels from oils.
• Stage We are nearing the end of Stage 1.

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Conclusions/Summary

• Synthesized novel materials with high catalytic
  performance for biodiesel generation from soybean
  oil.
• Synthesized multifunctional catalysts for making
  biodiesel from fat.
• Investigated of the recyclability of optimal
  catalysts.
• Established a partnership with West Central
  Cooperative.

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Stage Gate Fit

• This project is near the end of Stage 1 the
  beginning of Stage 2.

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Task Objective Detail

• Project 2 - Conversion of Gylcerol into
  Propanediol
• Technical objective explore the feasibility of
  using ionic hydrogenation to convert glycerin
  into 1,3-propanediol, a component in polymers.
• Milestones established
• 1. Optimize the conversion of glycerin.
• 2. Scale up optimized reaction to a kilogram
  scale.
• 3. Evaluate process economics of the optimized
  reaction
• Go No/Go decision points
• Can this process be scaled up?

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Technical Barriers AddressedChemicals and
Materials
Poly(trimethylene terephthalate)
A softer fiber than either polyester or nylon and
superior comfort-stretch and dyeability
Shell Chemicals PTT DuPont Sorona? or 3GT?
polymer
Problem Lack of readily available, inexpensive
method for the synthesis of PDO
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Technical Barriers AddressedChemicals and
Materials
Current State-of-the-art methods
Shell Chemicals
DuPont
Developed at a pilot plant in the Decatur, IL,
facility of Tate Lyle, a major corn-based
products company with expertise in fermentation
processes.
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Organization/Approach

• Project 2 - Conversion of Gylcerol from Biodiesel
  Production into 1,3-Propanediol

Ionic Hydrogenation
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Task Objective Detail
Glycerol to PDO
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Task Objective Detail
()
(-)
Porous Silicon
HF/Ethanol
P-type (100) Boron Doped Si Wafer
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Task Objective Detail
A
B
C
1.5 x 1.5 mm2 150 mA/cm2
5 x 5 mm2 295 mA/cm2
5 x 5 mm2 370 mA/cm2
D
E
F
5 x 5 mm2 440 mA/cm2
5 x 5 mm2 515 mA/cm2
5 x 5 mm2 600 mA/cm2
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Task Objective Detail
Reaction condition Glycerol (10 mmol) TFA (50
mmol) Ground Wafer (5 mg) 40 ºC
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Market Customers

• Customers biodiesel manufacturers
• Production costs - The current price of PDO is
  around .80 per pound. We estimate the cost of
  glycerol, acid, and silane at a total of
  .20-.30 per pound.
• Market Dynamics - For every gallon of biodiesel
  produced, one pound of glycerin is produced. The
  expansion of biodiesel production will produce an
  additional one billion pounds of glycerin per
  year. The price of glycerin may drop to .05 -
  .10 per pound.
• Developing a system to make high value chemicals
  such as 1,3-propanediol from the glycerin stream
  will add value for biodiesel producers.

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Competitive Advantage

• Competitive Advantage- Several PDO plants have
  recently been built that will increase American
  manufacturing capacity by about 120,000 metric
  tons per year. The 75,000 MTPY Shell Chemical
  PDO plant completed in Louisiana uses fossil fuel
  as the feedstock while the 45,000 MPTY Tate and
  Lyle plant built in Tennessee will use cornstarch
  fermentation to produce PDO. While the
  cornstarch fermentation process affords the
  manufacture of PDO from a renewable resource, it
  is fraught with problems including low yield and
  poor economics.

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Strategic Fit

• We have established a partnership with West
  Central Cooperative. West Central Cooperative has
  a state-of-the-art, 9,000 square foot facility
  that manufactures 12 million gallons of biodiesel
  annually, and is the largest biodiesel plant in
  the United States.
• They will work with us on the reaction scale up
  and will evaluate the process economics.
• Fit with the Biomass Programs biorefinery
  pathway approach products from oils.
• Stage We are nearing the middle of Stage 1.

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Conclusions/Summary

• We have demonstrated that porous silicon can
  function as a new reagent for the conversion of
  glycerol to PDO.
• We will investigate the possibility of using
  waster microchips or rejected silicon wafers as
  sources for porous silicon.
• We will work with West Central Coop. on the
  reaction scale up and will evaluate the process
  economics.

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Stage Gate Fit

• This project is in the middle of Stage 1