A new biorefinery platform intermediate
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A New Biorefinery Platform Intermediate. Principal Investigator: Doug Cameron Project Managers: Jim Millis, Paris Tsobanakis 2005 OBP Bi-Annual Peer Review Integrated Biorefinery Platform November 16, 2005. Overview. Scope of Work Plan

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A new biorefinery platform intermediate

A New Biorefinery Platform Intermediate

Principal Investigator: Doug Cameron

Project Managers: Jim Millis, Paris Tsobanakis

2005 OBP Bi-Annual Peer Review

Integrated Biorefinery Platform

November 16, 2005


Overview

Overview

  • Scope of Work Plan

  • Cargill, in partnership with Codexis, is developing a fermentation route to a novel platform chemical, 3-hydroxypropionic acid (3-HP)

  • We are also collaborating with PNNL to develop novel catalytic process for the conversion of 3-HP to acrylic acid and acrylamide

Microbial

fermentation

Chemical

catalysis

Acrylic Acid

Acrylamide

Glucose

3-HP


Overview1

Overview

  • Award was for $6.09 million in matching DOE funds for a 3 year program (total $12.2 MM), representing a 50/50 cost share

  • Biotech/Codexis work started in May 2003; Chemical conversion/ PNNL work started in December, 2003

  • The pace of the program was slowed after one year as commercial activities lagged technology development.

    • $0.60 MM received in FY03 (May to September)

    • $1.66 MM received in FY04

    • $0.77 MM received in FY05

    • Request for FY06 and beyond to be submitted by end of November

    • 50% complete

    • Completion of the program will require a one year extension


Overview2

Overview

  • The program is currently in Development Phase

  • Barriers addressed

    • 3-HP is a novel platform chemical (identified as a Top Ten product) with the potential to impact both large, commodity markets and new, emerging markets

    • Technical barriers addressed:

      • Specific improvements in metabolic pathway engineering to yield highly productive, high yield fermentation technology

      • Novel product recovery and process integration

      • Design of new catalysts and processes (for derivatives of 3-HP)


Project goals and objectives

Project Goals and Objectives

Cargill, through collaboration with their partners Codexis and PNNL will develop a new bio-based platform technology to produce a portfolio of products based on 3-HP produced by the fermentation of carbohydrates.

This project will deliver an organism and process for 3-HP production, and catalysts and complete process concepts suitable for piloting and scale-up for industrial production.

Our current timeline fits well with the FY08 Solicitation schedule


A new biorefinery platform intermediate

Project Strategic Fit

poly(hydroxypropionate)

1,3-propanediol

EEP

3-hydroxypropionic acid

acrylamide

malonic acid

acrylic acid


A new biorefinery platform intermediate

Project Strategic Fit

1994 = 100

Market dynamics have emerged to make 3-HP conversion to acrylic as an attractive alternative to propylene oxidation


Project strategic fit

Project Strategic Fit

57%

Propylene

Polypropylene

  • Despite a global market of 6.6 billion pounds for acrylic acid, propylene used for acrylic production is a small portion of propylene supply, with price driven principally by polypropylene

  • Growth requires one new world class plant every year

12%

Acrylonitrile

Adiponitrile

ABS/SAN resins

Acrylamide

Nitrile rubber

10%

Propylene oxide

Polyurethane polyols

Propylene glycols

Glycol ethers

8%

Cumene

Phenol

Acetone

7%

Oxo Chemicals

(butanol, 2-EH)

4%

Acrylic acid

4%

Isopropyl alcohol

4%

Polygas chemicals

(nonene, dodecene)

3%

Other chemical uses


A new biorefinery platform intermediate

Project Strategic Fit

  • Sponsoring BU within Cargill is Industrial Bioproducts, a member of the Emerging Business Platform

  • This project enables a lower cost (and less price volatile) route to acrylic acid from renewable sugars. Joint analysis of production economics with an industry leader indicates a potential manufacturing cost advantage vs. propylene oxidation of >5¢ per pound for a Midwest plant.

  • Energy consumption would be reduced 61% compared to the petrochemical route. By 2020, the acrylic acid product alone would displace 7,200 barrels of oil/day with domestically produced corn.

  • The biorefinery route to acrylic acid would eliminate 600,000 lbs of SOx, 1 million lbs of NOx and 2.8 billion lbs of CO2 annually.


Project approach

Project Approach

Glucose

NADH

ATP

1

2

3

malonate

semialdehyde

L--alanine

-alanine

Pyruvate

glutamate α-ketoglutarate

α-ketoglutarate glutamate

4

NADH

1 – Pyruvate / alanine aminotransferase

2 – Alanine 2,3-aminomutase

3 – -alanine aminotransferase

4 – 3-HP dehydrogenase

3-HP


Project collaboration

Project Collaboration

Microbial catalysis/

fermentation

Chemical

catalysis

Acrylic Acid

Acrylamide

Glucose

3HP

Task Group 1

Task Group 2

Task Group 3

Codexis: Enzyme & pathway evolution

Cargill: Host strain construction & fermentation process

PNNL: Catalyst & process development

Cargill: Process design, integration & economics


Project tasks

Project Tasks

Task Groups

  • Biochemical pathway optimization

  • Host strain construction and fermentation process development

  • Catalyst screening and development, process development and process integration for the conversion of 3-HP to acrylic acid


Project tasks1

Project Tasks

  • Random

  • Phylogenetic – semisynthetic

  • Targeted

  • Hit shuffling

  • ProSAR

Relative improvement

WT

Rd4

Rd1

Rd2

Rd3

Rd6

Rd7

Rd5

Rd8

Parent

Rounds of shuffling

Task Group 1: Biochemical pathway optimization (Codexis)

Targets

  • Improve performance of Enzyme 2 to meet productivity targets

  • Balance supporting pathway enzymes to maximize productivity and yield

    Milestones

  • Performance measured by fermentation productivity (see Task Group 2)

    Technical Risks

  • Enzyme 2 does not meet activity target

Future plans

  • Continue optimization of Enzyme 2

  • Perform pathway shuffling to optimize pathway performance


Project tasks2

Project Tasks

Task Group 2: Host strain construction and fermentation process development (Cargill)

Targets

  • Host strain selected and pathway engineered into strain

  • Pathway constructed and 3-HP produced

  • Fermentation optimization to meet economic targets

    Milestones

  • Specific productivity targets communicated to DOE (confidential)

    Technical Risks

  • Targets for high productivity and titer are not met

    Future plans

  • Incorporate improved variants of Enzyme 2 into pathway

  • Improve yield and productivity of fermentation process


Project tasks3

Project Tasks

Task Group 3: Catalyst screening and development, process development and process integration for the conversion of 3-HP to acrylic acid (PNNL, Cargill)

Targets

  • Catalysts screened and selected for the dehydration of 3-HP to acrylic acid

  • Catalyst & process conditions demonstrated near quantitative conversion and selectivity

    Milestones

  • Milestones met for pure 3-HP

    Technical Risks

  • Catalyst robustness/ effect of impurities

    Future plans

  • Demonstrate extended catalyst life

  • Demonstrate catalyst performance on 3-HP produced by fermentation

  • Process integration


Market customers

Market & Customers

  • This project enables the first biobased route to acrylic acid, a commodity product with a global market approaching 7 billion pounds per year.

  • Meeting economic targets for acrylic will also enable other 3-HP derivatives.

    • 1,3-propanediol

    • malonic acid and others


Competitive advantage

Competitive Advantage

  • Cargill’s route to acrylic acid through 3-HP is advantaged over other technology options

    • Propane oxidation is unproven and does not meet DOE OBP objectives

    • Lactic acid dehydration pursued by many parties without success

    • Future may allow use of biomass feedstock for Cargill process, thus driving costs downward

  • Relative attractiveness of 3-HP to acrylic technology will depend on propylene price, but current forecast for high prices and volatility provides the basis for optimism


Progress and accomplishments

Progress and Accomplishments

  • Production of 3-HP from glucose demonstrated by a novel pathway

  • Catalyst discovered for 3-HP to acrylic acid process

  • Dehydration reactor designed to overcome equilibrium limitations


Future work

Future Work

Development Stage Plans

  • Due to a reduced rate of spend in FY04 and FY05, Cargill requests an extension of one year to complete the program. New proposed date for completion is May ‘07.

  • Plans are to accelerate the spend over the next 18 months.

  • Interim milestones and commercial plans communicated to DOE in July 2005 review (confidential).

  • Our current timeline fits well with the FY08 Solicitation schedule


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