Chemistry of Go: Innovations in Alternative Fuels

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2016 Material Science Series http://bit.ly/2016MaterialScienceSeries

Ever since the Model-T first rolled off the production line in 1908, the world of transportation has never been the same. Join us as we examine the science behind innovations that will drive the world for the next 100 years.

* If you are attending today, you are already signed for all the webinars in the “Chemistry of Go” mini-series so just save the dates of May 5th and June 2nd for the upcoming webinars.

The 2016 Material Science Series is co-produced with ACS Industry Member Programs and C&EN

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4/6/2016

2016 Material Science Series

“Chemistry of Go: Innovations in Alternative Fuels”

Jennifer Holmgren

Mark Jones

Chief Executive Officer, LanzaTech

Executive External Strategy and Communications Fellow, Dow Chemical

Slides available now! Recordings will be available to ACS members after one week

www.acs.org/acswebinars The 2016 Material Science Series is co-produced with ACS Industry Member Programs and C&EN

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“The Chemistry of Go: Innovations in Alternative Fuels” Jennifer Holmgren, CEO, LanzaTech 2015 LanzaTech. All rights reserved.

2015 LanzaTech. All rights reserved.

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Easter Parade New York City 1900

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Easter Parade New York City 1913

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What do we need to “Go”? Movement requires energy. Fuels carry energy.

What makes a good fuel? Energy-dense Inexpensive Easy to handle

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Audience Survey Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

What percentage of cars in 1900 were electric?

• Less than a quarter • About a quarter • Between a quarter and a half • More than half • About three-fourths

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What percentage of cars in 1900 were electric?

• Less than a quarter • About a quarter • Between a quarter and a half (37%) • More than half • About three-fourths

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Evolution of Go…Steam, Electricity and Coal

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And then came Petroleum…

• Reliable • Practical • Cheap • Efficient • Easier to Control • Less likely to explode

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Refinery Output

Refinery Products

Refinery Gasoline/Cars

Jet Fuel/Airplanes

Diesel Trucks/ Construction Equipment

Crude Oil

Asphalt

Bunker Fuel (Ships)

Lube Oils

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Refinery Overview • Crude oil is a complex mixture of various lengths and shapes of carbon and hydrogen molecules, with different chemical properties. In addition, crude oil contains significant levels of heteroatoms such as S, N which must be removed before burning fuels. • A typical US refinery processes 100,000 – 250,000 barrels (~ 4 – 10 million gallons) of crude oil per day. • Processing unit operations vary by refinery and depend on crude oil used as input as well as desired product slate.

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Crude Oil •

•

Crude oil varies in both density and sulfur content depending on its origin around the world. This results in differences in cost for purchasing the oil and required technology to refine it into products.

H H H H Class – Paraffin Name – Butane

H–C–C–C–C–H H H H H H H H H H H H H

Class – Aromatic Name – Octane

H–C–C–C–C–C–C–C–C–H H H H H H H H H H H

Class – Aromatic Name – Benzene

C

H C

C C

C H C

H Class – Cyclo-paraffin Name – Cyclohexane

H H H C H C H C H H

H H C H C H C H H 22

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Chemical Conversion: Adding Value • Cracking – Converts heavy gas oils and residual to higher value gasoline and diesel components – Cracking can be thermal (Coker) or catalytic (Fluidized Catalytic Cracker)

• Alkylation ─ Converts shorter-chain molecules to longer-chain molecules ─ Typically C3/C4 molecules upgraded to gasoline components

• Upgrading ─ Improvement of low-octane fuels to high-octane fuels (Reformer) ─ Dehydrogenation reactions, converting linear hydrocarbons to branched and cyclic hydrocarbons

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Boiling Point Separation •

Smaller hydrocarbons are gaseous with low boiling points

•

Longer chains are liquids, then waxes and finally solids

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Generic Refining Flowscheme LPG

Hydrogen

Naphtha Hydrotreating

Gasoline Isomerization

Mid-Distillate Hydrotreating

Crude Distillation

Catalytic Reforming

Gasoline, Aromatics

Hydrocracking

Jet Diesel

Jet, Diesel LPG

Crude

Alkylation FCC

Gasoline Gasoline Cycle Oil to Hydrotreating or Hydrocracking

Vacuum Distillation Coking

Petroleum Coke

Asphalt

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Milestones

Bao Steel China

Shougang China

WBT Taiwan

Sekisui Japan

1Q2011

3Q2011

1Q2013

4Q2103

JV registered

4Q2011

4Q2011

4Q2012

BEP

2Q2011

1Q2012

2Q2013

Audience Survey Question

Agreements executed

ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

1Q2014

How are the hydrocarbons produced 4Q2013 at the top of4Q2014 the 1Q2012 4Q2012 Start Up column, different 1Q2012from those 4Q2012produced 1Q2014 1Q2015 lower down? Mechanical completion

Fixes 10 day run

3Q2012

1Q2014

1Q2015

• They have longer chains and lower boiling points Run 10 4Q2012

Run 3 1Q2013

Run 1 2Q2014

4Q2015 • They have shorter chains and lower boiling points

Integrated operation

• They have longer chains and higher boiling points • They have shorter chains and higher boiling points

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How are the hydrocarbons produced at the top of the column, different from those produced lower down? • They have longer chains and lower boiling points • They have shorter chains and lower boiling points • They have longer chains and higher boiling points • They have shorter chains and higher boiling points * The longer the chain the higher the boiling temperature.

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Evolution of “Go” Vehicles have changed a lot. Their fuel? Not so much

Cars have been tied to gasoline for most of their history, but fuel tech keeps evolving… Now more than ever, we need to look at alternative solutions and technologies to make us “GO”

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The Status Quo is not an Option

14% of Global CO2 Emissions come from transportation fuels

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A Carbon Smart World Remaining: 1000 GtCO2 1870-2011: 1900 GtCO2

65% of 2°carbon budget: USED

Must stay in the ground

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St. Louis Post Dispatch October 17, 2014

Advanced Biofuels Taking Off

POET-DSM September 3, 2014

Biofuels Digest October 6, 2014

Biofuels Digest October 16, 2014

National Geographic October 17, 2014

Getting a New Process to Scale Continuous improvement at scale

Discovery

Applied R&D

Ease of funding

Adapt and adopt from others Engineering Development Diffusion Pilot and Demonstration First Commercial

Evolution 32

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RTP™ History 2006-Present Renewable Liquid Fuels: Key alliances & Project execution

1998-2005 1989-1998 Commercialization & Scale-up US - $20+M sale for Chemicals

Petroleum Business Development & sale for US$100 MM

1984: Foundation

* Since 1996, Ensyn has returned to shareholders 2x the amount it has raised in equity funding 33

Commercial Isobutanol/Ethanol Plant in Luverne, MN Agri-Energy

Commissioning timeline Date

Statistics First commercial scale renewable isobutanol plant in the world

Event

September 2010

Purchased Luverne plant

May-Sep. 2012

Encountered unexpected levels of contamination

Sep.-May 2013

Revamped plant and procedures to address contamination issues

May – Sep. 2013

Tested new systems and procedures

Oct.– April 2014

Encountered operability issues related to water recycling and solids handling

May 2014 – Present

Running in side-by-side mode to better handle water and solids. Improves operability of plant, and simplifies IBA production. WORKS WELL

Purchased in 2010 & 100% owned by Gevo

Made minor system and hardware upgrades

World-scale chemicals plant Luverne Facility

Typical Specialty Chemical Plant

Feedstock

Carbohydrates-based

Petroleum-based

Expected Production

100 MM lbs per year of Isobutanol/Ethanol 100 MM lbs per of year of animal feed

50-175 MM lbs per year(1)

(1) Derived from a sample of 10 operating specialty chemical plants producing chemicals such as Methyl Amines, Dimethyl Formamide, EPVC, Phenol Acetone, Formaldehyde, Polyamides and Methanol © 2014 Gevo, Inc. | 34 Source: International Process Plants, EIA

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Hydro-Processed Esters and Fatty Acids (HEFA) and Green Diesel +

CO2

HO

CH3

Free Fatty Acid MW=200-300

O O

H2 CH3

HC O O

H3C

CH3

OO

CH3 Triglyceride MW=700-900

O

CO2

H2O +

H2O

H3C

CH3 CH3

H3C

H3C

CH3

CH2 +

H3C

CH3

H3C Straight Chain Paraffins

Catalyst

 Natural oils contain oxygen, have high molecular weight. Catalyst

 First reaction removes oxygen – product is diesel range waxy paraffins

H2 CH3 CH

3

H3C

 Second reaction “cracks” diesel paraffins to smaller, highly branched molecules

CH3 CH3

CH3 H3C

+ H3C Synthetic Paraffinic Kerosene

Feedstock flexible,

CH3CH3

+

CH3

H3C

but with consistent product properties 35

Source: Dr. James Kinder, Boeing

Global green diesel & HEFA production Phillips 13 M Gallons USA

Neste Oil 240 M Gallons Netherlands Blue Sun 2 M Gallons USA

Preem 126 M Gallons Finland

UPM 38 M Gallons Finland

Neste Oil 114 M Gallons Finland Eni 100 M Gallons Italy

AltAir 30 M Gallons CA (Est. 2015)

Sinopec 6 M Gallons China

SG Preston 120 M Gallons OH (Est. 2017)

Diamond REG Green Diesel 75 M Gallons 137 M Gallons LA LA

Petrixo 310 M Gallons Fujairah, U.A.E. (Est. TBD)

BP 29 M Gallons Brisbane, Aus.

Neste Oil 240 M Gallons Singapore

Petrobras 69 M Gallons Brazil

Supply available to address significant aviation markets Copyright © 2014 Boeing. All rights reserved.

Source: Dr. James Kinder, Boeing

Filename

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The Boeing Company

ASTM Fuel Approval Process- ASTM D4054 Test Program

OEM Internal Review

Specification Change

OEM Internal Review

Reject or Additional Data as Required

Fuel Specification Properties

ASTM Review & Ballot

Fit-for-Purpose Properties

Component or Rig Tests

Research Report

Reject or Additional Data as Required

FAA Review Engine Endurance Test

OEM Approval Incorporate into Fuel Specification with FAA Consensus

ASTM Specification

 In depth, multiparty review Source: Dr. James Kinder, Boeing

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BOEING PROPRIETARY

Great Progress on Certification for Flight Certification “Less than a decade ago, the prospect of flying commercial aircraft on sustainable aviation fuels (SAF) seemed unrealistic due to the associated technical and safety challenges, the developments have been impressive!” IATA Roadmap

Type

ASTM approval

When

Fischer Tropsch (FT) (or BtL)

Max 50% blend

2009

Hydrotreated Esters and Fatty Acids (HEFA)

Max 50% blend

2011

Renewable Synthesized Iso-Paraffinic (SIP)

Max 10% blend

2014

Butanol to Jet Fuel (ATJ)

Max 30% blend

2016

Pipeline: Green Diesel, Ethanol to Jet (EtJ), pyrolysis and catalytic cracking (Hydroprocessed Depolymerized Cellulosic Jet), catalytic hydrothermolysis and catalytic conversion of sugars.

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Carbon Recycling: The LanzaTech Process

Proprietary Microbe

Gas fermentation technology converts Crich gases to fuels and chemicals

Gas Feed Stream

Gas Reception Compression Fermentation

Recovery

Product Tank

Performance milestones achieved and exceeded for >1000 hours

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ArcelorMittal, Gent Ground Works Started October 2015 Gas Testing Station Produces Ethanol January 2016

Connection to Steel Mill Gas Lines March 2016

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Embrace the Circular Economy: Recycle Everything

CCU

“CCS”

Recycle

Make

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All Solutions Must Succeed… Even Those We Don’t Yet Know.

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Jennifer Holmgren

Mark Jones





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2016 Material Science Series http://bit.ly/2016MaterialScienceSeries

Ever since the Model-T first rolled off the production line in 1908, the world of transportation has never been the same. Join us as we examine the science behind the innovations that will drive the world for the next 100 years.

* If you are attending today, you are already signed for all the webinars in the “Chemistry of Go” mini-series so just save the dates of May 5th and June 2nd for the upcoming webinars.

The 2016 Material Science Series is co-produced with ACS Industry Member Programs and C&EN

44

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®






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Jennifer Holmgren

Mark Jones





46

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How has ACS Webinars benefited you?

®

“A perfect webinar! Dee Strand was fantastic. The Chemistry of Hello: Lithium Ion Batteries was of the clearest and most educational per unit time technical presentations that I have heard in my more than 25 years as a professional scientist.”

Walter Cicha, Ph.D., Industrial Technology Advisor, Industrial Research Assistance Program, National Research Council of Canada

Be a featured fan on an upcoming webinar! Write to us @ [email protected]

47

facebook.com/acswebinars @acswebinars youtube.com/acswebinars

Search for “acswebinars” and connect! 48

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Benefits of ACS Membership Chemical & Engineering News (C&EN) The preeminent weekly news source.

NEW! Free Access to ACS Presentations on Demand® ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events.

NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more.

http://bit.ly/ACSjoin

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®

ACS Webinars does not endorse any products or services. The views expressed in this presentation are those of the presenter and do not necessarily reflect the views or policies of the American Chemical Society.


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Chemistry of Go: Innovations in Alternative Fuels

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