Biorefining Magazine - February 2011

INSIDE: DEVELOPING BEST PRACTICES FOR BIOMASS february 2011

Enter the

Bio-Barons Oil Today’s Industrialists Discuss Significant Potential of Pyrolysis Oil Refining Page 20

Plus Research Aims to

Control Lignin Production in Plant Growth Page 26

And Meeting the EU’s Renewables Directive with Energy Crops Page 30

www.biorefiningmagazine.com

february 2011 | Biorefining Magazine | 1

2 | Biorefining Magazine | february 2011

contents |

february issue 2011 VOL. 02 ISSUE 02

20

feedstock

The Bio-Oil Barons Pyrolysis oil experts discuss upgrade technology and the fuel’s potential

By Bryan Sims

26

30

research

europe

Unlocking the Mysteries of Lignin

Energizing Europe

Controlling lignin production in plants will mean less recalcitrant biomass By Erin Voegele

Continental energy crop development will help meet EU bioenergy goals

By Luke Geiver

Contents DEPARTMENTS

4 Editor’s Note

9 Legal Perspectives

6 Advanced Advocacy

10 Business Briefs

Feedstock Diversity

By Ron Kotrba

A Bright Future for Better Fuels

By Michael Mcadams

7 Industry Events

Going Private

BY Danielle d. smid

People, Partnerships & Deals

12 Startup

Biorefining News & Trends

Upcoming Conferences & Trade Shows

8 Talking Point

On the Road to Best Biomass Practices By thomas corle & roger moore

ON THE COVER: George Huber, University of Massachusetts-Amherst chemical engineer and co-founder of Anellotech Inc.

february 2011 | Biorefining Magazine | 3

|

editor’s note

The 2011 Pacific West Biomass Conference & Trade Show, a BBI International event held in Seattle and coproduced by Biorefining Magazine and Biomass Power & Thermal, was another successful regional

feedstock diversity Ron Kotrba, Editor rkotrba@bbiinternational.com

show. I had many interesting conversations with speakers, exhibitors and attendees, some of which have led to solid story ideas for upcoming issues.

The keynote address, given by Washington State Commissioner of Public Lands, Peter Goldmark, was briefly interrupted by two misguided protesters who snuck into the conference. Goldmark was there to announce to the hundreds in attendance his proposal for legislation that would establish a Washington State Department of Natural Resources bio-jet fuel project. The two protesters shouted, “All your clear-cuts, all your lies, we will never compromise,” after which they were escorted out. There seemed to be a lack of understanding by these protesting individuals on what biomass represents. This was the topic of a recent post of mine on The Biorefining Blog, found on our website.

Those of you reading this know that biomass is crop waste from agriculture, citrus peels from juicers, black liquor waste streams from pulp and paper mills, manure from livestock, municipal solid waste from cities, food waste from manufacturers and, yes, also wood waste from industry—and on and on.

The biomass industry does not represent clear-cutting forests to make power.

There is, however, a faction in the industry that supports responsible, managed forest logging on private lands—plant, tend, cut, replant—like what the paper industry has been doing for a very long time. Not clear-cutting old-growth forests.

Green energy from biomass reduces greenhouse gas emissions, and is much cleaner than coal or oil. Maybe these few individuals should promote positive messages like reduce, reuse and recycle, and take a look at what the biomass industry truly represents: reducing fossil fuel consumption and promoting domestic energy production.

Perhaps these protesters could have saved a tree or two if they hadn’t used cardboard signs while passing out paper flyers. If their response to this particular observation were that these leaflets and signs were made with post-industrial or postconsumer recycled paper, then my retort would be: Welcome to the biomass industry.

for more news, information and perspective, visit biorefiningmagazine.com/thebiorefiningblog

ASSOCIATE EDITORS In his feature article, “The Bio-Oil Barons,” Bryan Sims talks with leaders in the pyrolysis oil sector about applications, upgrading and the fuel’s overall emergence.

4 | Biorefining Magazine | february 2011

Erin Voegele, author of “Unlocking the Mysteries of Lignin,” investigates research to genetically control lignin production in plants and its potential impact on biorefining.

“Energizing Europe,” written

by Luke Geiver, discusses feedstock research and crop development on the spatially limited continent of Europe to help meet GHG reductions.

EDITORIAL EDITOR Ron Kotrba rkotrba@bbiinternational.com ASSOCIATE EDITORS Erin Voegele evoegele@bbiinternational.com Luke Geiver lgeiver@bbiinternational.com Bryan Sims bsims@bbiinternational.com COPY EDITOR Jan Tellmann jtellmann@bbiinternational.com

ART ART DIRECTOR Jaci Satterlund jsatterlund@bbiinternational.com graphic designer Erica Marquis emarquis@bbiinternational.com

PUBLISHING CHAIRMAN Mike Bryan mbryan@bbiinternational.com CEO Joe Bryan jbryan@bbiinternational.com VICE PRESIDENT Tom Bryan tbryan@bbiinternational.com

SALES VICE PRESIDENT, SALES & MARKETING Matthew Spoor mspoor@bbiinternational.com EXECUTIVE ACCOUNT MANAGER Howard Brockhouse hbrockhouse@bbiinternational.com SENIOR ACCOUNT MANAGER Jeremy Hanson jhanson@bbiinternational.com ACCOUNT MANAGERS Chip Shereck cshereck@bbiinternational.com Marty Steen msteen@bbiinternational.com Bob Brown bbrown@bbiinternational.com Andrea Anderson aanderson@bbiinternational.com Dave Austin daustin@bbiinternational.com CIRCULATION MANAGER Jessica Beaudry jbeaudry@bbiinternational.com SUBSCRIBER ACQUISITION MANAGER Jason Smith jsmith@bbiinternational.com ADVERTISING COORDINATOR Marla DeFoe mdefoe@bbiinternational.com

Customer Service Please call 1-866-746-8385 or email us at service@bbiinternational.com. Subscriptions to Biorefining are free of charge to everyone with the exception of a shipping and handling charge of $49.95 for any country outside the United States, Canada or Mexico. To subscribe, visit www.biorefiningmagazine.com or you can send your mailing address and payment (checks made out to BBI International) to: Biorefining Subscriptions, 308 Second Ave. N., Suite 304, Grand Forks, ND 58203. You can also fax a subscription form to (701) 746-5367. Back Issues, Reprints and Permissions Select back issues are available for $3.95 each, plus shipping. Article reprints are also available for a fee. For more information, contact us at (701) 746-8385 or service@bbiinternational.com. Advertising Biorefining provides a specific topic delivered to a highly targeted audience. We are committed to editorial excellence and high-quality print production. To find out more about Biorefining advertising opportunities, please contact us at (701) 746-8385 or service@bbiinternational.com. Letters to the Editor We welcome letters to the editor. Send to Biorefining Letters to the Editor, 308 2nd Ave. N., Suite 304, Grand Forks, ND 58203 or e-mail to rkotrba@bbiinternational.com. Please include your name, address and phone number. Letters may be edited for clarity and/or space.

Please recycle this magazine and remove inserts or samples before recycling COPYRIGHT Š 2011 by BBI International

february 2011 | Biorefining Magazine | 5

|

advanced advocacy

A Bright Future for Better Fuels Cooperation is needed among all biofuel advocates to pass multiyear policy goals

BY Michael mcadams

I

have written of my dad’s sage political advice before in this column. One time when I asked him to describe the word “politics” to me, he quickly responded with a confident, “Politics is the art of the possible.”

As we enter 2011 with all the continuing changes in Washington and in our industry, it’s worth having a conversation on determining what our policy as a singular biofuels industry should be. I might sound like a broken record, but it’s exactly the question that needs answering for each organization, no matter what generation of technologies they represent.

The unfortunate part of finally renewing the existing tax credits last year was that this year we’d have to return in somewhat of a Groundhog Day mentality, revisiting the question of how to advocate a comprehensive biofuels tax policy before end of year. As many of you are well aware, the ethanol, biodiesel, renewable diesel, and alternative fuels tax credit expire at the end of this year. But I understood the IRS was to have rules out by the end of January instructing those seeking retroactive tax credits for 2010. This rule should also set out the requirements for the coming year.

We have major changes in the organization of the House of Representatives this year. Several members who sat on the powerful ways and means committee supporting various biofuels tax credits no longer hold their seats on that committee. The Republicans now hold the chairmanship and boast 21 seats on that committee, compared to 15 for the Democratic minority.

To give perspective, in the last Congress the ratio was 25 Democrats to 15 Republicans. The new chairman, Dave Camp,

6 | Biorefining Magazine | february 2011

R-Mich., is a thoughtful and pragmatic conservative who has traditionally favored free market tax incentives for business to invest in renewable energy versus creating another federal program. He has a long-held commitment of working and supporting the solar industry and shares many policies and philosophies of former leading Republican committee member Jim McCrey, R-La. As for the Democrats who have left the ways and means committee, Chris Van Hollen, D-Md., and Allyson Schwartz, D-Pa., both were instrumental last year in introducing legislation that would have added the biofuels industry for coverage under the Investment Tax Credit program.

In a rare show of common support, five of the top biofuels associations and 50 companies all worked together to support this effort. Ultimately, however, with a limited session and reluctance to open the floodgates to new provisions, it wasn’t in the final legislation.

On the other side of Capitol Hill, the U.S. Senate Committee on Finance has one significant change at this point, with Orin Hatch, R-Utah, taking over as the ranking minority member from Chuck Grassley, R-Iowa. The two senators have a vastly different view of the ethanol tax credit with Grassley as its leading Senate supporter. Already, we’ve seen several public statements from lawmakers and industry associations on what to do with the ethanol tax credit.

But as for advanced biofuels, the focus remains on what would be the most effective policy choice to help commercially deploy new technologies and first-of-kind plants, while putting Americans back to work.

Many of the Republicans on the House ways and means committee will be asking why Congress needs to extend existing cred-

its under tight budget constraints and to an industry already on its way. So with renewed focus on reducing the federal deficit and a desire to do away with many of the recovery act programs, particularly by new tea party members, the biofuels industry has plenty of hard work ahead.

That is why the conversation I mentioned earlier must happen, and must happen with great candor and intellectual honesty on all sides of our industry. How do we work together, and on what government support do we focus our attention?

For many in the corn ethanol industry, the answer appears to be infrastructure, while for most in the advanced biofuels industry the answer is help us build and deploy new technology.

In the short term, I want to suggest that we all begin the year with a bit of circlethe-wagon mentality as to the benefits of all biofuels generally. We reduce the dependence on foreign oil, we start creating new jobs, we provide a broad support for current and new forms of agriculture and rural America, and we deliver improved environmental performance from crude oil-based fuels. What we should avoid at all costs is a circular firing squad.

Our future is bright, the benefits of biofuels are plentiful. The challenges that lay ahead this year are real and significant. Let’s begin the year with a spirit of cooperation.

Let’s listen to each other and let’s roll up our sleeves and find a public policy solution that protects what we have built to date, and expedites the building of an advanced biofuels industry for the future.

Author: Michael McAdams President, Advanced Biofuels Association (202) 747-0518 mmcadams@bhfs.com

events calendar |

International Biomass Conference & Expo

May 2-5, 2011

America’s Center, St. Louis, Missouri The largest, fastest growing biomass event was attended in 2010 by 1,700 industry professionals from 49 states and 25 nations representing nearly every geographical region and sector of the world’s biomass utilization industries—power, thermal energy, fuels and chemicals. Plan to join more than 2,500 attendees, 120 speakers and 400-plus exhibitors for the premier international biomass event of the year.

(701)746-8385 | www.biomassconference.com

Fuel Ethanol Workshop & Expo

June 27-30, 2011

Houston, We Have a Solution 9/14

Mark your calendars and get ready, the No. 1 biorefining event in the world is coming. For three days, Sept. 14-16, the 2011 International Biorefining Conference & Trade Show to be held in Houston, will bring together hundreds of industry professionals to discuss all things advanced.

Produced by Biorefining Magazine, the unprecedented event will offer a comprehensive look into advanced biomass refining including technology scale-up, project finance, policy, feedstock use and more. Geared towards industrial, petroleum and agribusiness ventures, the program will highlight advanced biofuels development and distribution, biobased platform chemicals, polymers and other renewable molecules.

The conference will be held at Hilton Americas. Participants already set for the trip to Houston will feature finance (venture, private and institutional equity), petroleum and petrochemical refining, pulp and paper milling, biofuels and biobased products manufacturing and project development, agricultural processing and waste management, and will also be of interest to professionals from auto manufacturing, aviation, government/military, and research and academia.

Starting with industry tours of the region’s most innovative bioprojects and facilities, the conference will cover the biggest issues in the biorefining sector today. Included in the discussion will be petroleum industry perspectives on biorefining, converting existing industrial assets into next-generation biorefinieres; forging symbiotic relationships; aviation and military perspectives on biobased jet fuel, and among others, the global market outlook for biobased fuels and chemicals. For those startups seeking a foothold in the global industry, the conference will also cover venture capital and private equity viewpoints and overcoming the barriers to market entry.

In 2011, there’s one place and one event that will usher in the next phase of the surging biorefinery industry, and for three days in September, you could be there, at the 2011 International Biorefining Conference & Trade Show, along with the team from Biorefining Magazine, to listen and learn how the next generation of advanced biofuels and biobased chemicals is succeeding now.

Indiana Convention Center, Indianapolis, Indiana The FEW is the largest, longest-running ethanol conference in the world, and is renowned for its superb programming, which focuses on commercial-scale ethanol production—both grain and cellulosic—operational efficiencies, plant management, energy use, and near-term research and development. Speaker abstracts are being accepted through Feb. 25.

(701)746-8385 | www.fuelethanolworkshop.com

International Biorefining Conference & Trade Show

September 14-16, 2011

Hilton Americas – Houston, Houston, Texas This event will unite bioconversion technology providers and researchers from around the world with agriculture, forestry, and refining professionals to discuss and examine the scale-up and commercial establishment of advanced biofuels and biobased chemicals. Organized by BBI International and produced by Biorefining Magazine, the International Biorefining Conference & Trade Show brings together agricultural, forestry, waste, and petrochemical professionals to explore the value-added opportunities awaiting them and their organizations within the quickly maturing biorefining industry. Speaker abstracts are now being accepted online.

(701)746-8385 | www.biorefiningconference.com

Northeast Biomass Conference & Trade Show

October 11-13, 2011

Westin Place Hotel, Pittsburgh, Pennsylvania With an exclusive focus on biomass utilization in the Northeast—from Maryland to Maine—the Northeast Biomass Conference & Trade Show is a dynamic regional offshoot of Biorefining Magazine and Biomass Power & Thermal’s International Biomass Conference & Expo, the largest event of its kind in the world. This second conference will connect current and future producers of biomassderived electricity, industrial heat and power, and advanced biofuels, with waste generators, aggregators, growers, municipal leaders, utilities, technology providers, equipment manufacturers, investors and policymakers.

(701)746-8385 | www.biomassconference.com/northeast

february 2011 | Biorefining Magazine | 7

|

talking point

On the Road to Best Biomass Practices How Inbicon is working to commercialize corn stover feedstock

By Thomas Corle and Roger Moore

H

ead out of Chicago and down I-65 toward Indianapolis this time of year, and you’ll find the landscape flat, bare and monochromatic. Just when you’re convinced it’s endless, billboards pop up with giant black-and-white cows and teasing invitations. “We double Dairy you to Exit #220,” a typical one reads.

Pull into the visitors’ center, and you’ll discover a public showcase for a 20,000acre, state-of-the-art dairy farm. Of Indiana’s 154,000 milk cows, 30,000 live at Fair Oaks Farms on 10 different sites, in modern barns that keep them healthy, warm, and comfortable.

But for Larry Johnson, no winter tour of happy cows on milking carousels will catch his interest. Fair Oaks grows 17,000 acres of corn and alfalfa to feed its cattle. Johnson, Inbicon’s specialist in gathering and handling biomass for Inbicon Biomass Refineries, is captivated by the scale and speed of the fall corn harvest. “They take the whole corn stalk for silage—chopping, hauling, and stacking it into huge piles with covering tarps. Using Matt Gibson, a local custom harvester, one crew gathered 180,000 tons in just 21 days.”

Johnson sees this as encouraging evidence that corn stover could also be gathered easily—and in sufficient quantities to feed a biomass refinery of commercial scale. “Triple that amount, and you’ve got a year’s worth of stover,

8 | Biorefining Magazine | february 2011

enough for 20 million gallons of cellulosic ethanol.”

Companies like John Deere and Monsanto are performing rigorous tests of corn stover harvesting to determine preferred product specifications and the best harvesting methods. U.S. equipment makers are developing prototype harvesters, balers, and other machines to streamline the harvest and lower cost.

In Denmark, Inbicon’s parent company, Dong Energy, has spent 20 years gathering wheat straw to replace coal in its power plants. The amount has gradually risen to 1.6 million metric tons a year, as the company has developed highly efficient logistics for gathering, transporting, storing, and handling the biomass—including supplying wheat straw bales to Inbicon’s Kalundborg refinery, where cellulosic ethanol is being produced for a hundred retail outlets under Statoil’s Bio95 2G brand.

Findings like these, coupled with U.S. DOE and USDA data and Larry Johnson’s own research, are the basis of his comprehensive assessment of U.S. corn biomass collection practices.

Contrary to the negative commentary frequently appearing in the national press, the bottom line is optimism. He’s confident that “widely reported concerns are either not valid or will be easily managed.”

First of all, there’s plenty of corn stover—250 million tons annually in the U.S. Of this, 100 million tons can be economically harvested without causing agronomical or environmental problems.

That’s enough for more than 200 biomass

refineries producing well over 4 billion gallons of cellulosic ethanol annually.

“And as corn yield per acre rises, so will the amount of available stover per acre,” says Johnson.

Although his report to Inbicon remains confidential, he’s planning to share some of his recommendations at the International Biomass Conference & Expo, May 2-5 in St. Louis. He’ll focus on a sequence of 11 checkpoints that must be reached before stover collection can become commercialized.

First, he says, we must define biomass specifications and values, which will dictate harvesting equipment.

Manufacturers need to gauge demand for new machines before capital investment in mass production capacity is justified.

Feedstock delivery guarantees need to be in place prior to a biomass refinery’s financing. Signed delivery contracts must include detailed specs. Farmers need to evaluate the merits and costs of stover removal, and they’ll need cash before contracting to supply it. And finally, before groundbreaking, the biomass refinery will need project financing.

Success, for Johnson, is in the details—and in the planning. For the biomass industry, it’s a sensible start on the road to best practices.

Authors: Thomas Corle and Roger Moore Consultants, G-team tcorle@biopowered.biz rmoore@biopowered.biz

LEGAL PERSPECTIVE |

Going Private The pros and cons of moving from public to private

By Danielle D. Smid

M

any companies have been considering going private as a part of their efforts to reduce expenses.

“Going private” transactions describe the process of shareholders, management, or affiliates of a public company reducing the number of its shareholders to fewer than 300, thereby suspending the company’s obligation to file public reports with the Securities and Exchange Commission. There are benefits and detriments associated with a going-private transaction, which a company should consider before determining whether going private is in the best interest of the company and its shareholders.

Reporting companies are required to expend significant resources in connection with their Exchange Act obligations, including, but not limited to, higher external auditing and accounting costs, higher costs of internal controls, increased SEC reporting costs, increased legal consulting costs, increased D&O insurance costs, and special board meeting fees. In addition, the high cost of disclosure and compliance of remaining a public company has been exacerbated by the new XBRL reporting requirements.

Suspending a company’s reporting obligations will help reduce or eliminate these costs.

In addition, reporting companies are required to disclose information to the public, including to actual or potential competitors, that may be helpful to these competitors in challenging a company’s business operations and to take market

share, employees and customers away.

Suspending a company’s public reporting obligations will help to protect sensitive information from required or inadvertent disclosure to its competitors.

Moreover, operating as a non-SEC reporting company will reduce the burden on management and employees that arises from SEC reporting requirements, thus allowing management and employees to focus more of their attention on the company’s core business. Operating a non-SEC reporting company may eliminate the pressure and expectation to produce short-term per share earnings and may increase management’s flexibility to consider and initiate actions that may produce long-term benefits and growth.

Finally, smaller companies may receive only limited benefits from being reporting companies because of the company’s small size, the lack of analyst coverage and the limited trading of shares.

By going private a company will no longer have access to the public capital markets and may experience increased difficulty in raising capital in the future from only private sources. This may limit a smaller company’s ability to expand its business or raise additional working capital necessary to operate the company’s business. Among the renewable fuel companies that have gone private and must raise new capital, there is some consternation with the increased difficulty and the possibility of once again becoming public.

By going private a company’s shareholders will lose the benefits of

registered securities such as access to information concerning the company that is required to be disclosed in periodic reports to the SEC. Additionally, the company’s shareholders will lose certain statutory safeguards since the company will no longer be subject to the requirements of the Sarbanes-Oxley Act. The value and liquidity of a company’s shares could be reduced as a result of the company no longer being a publicly reporting company. In addition, a company’s directors and officers will have an increased potential for liability resulting from a going-private transaction.

Additionally, should a company again exceed the threshold number of shareholders, the company would have to incur significant costs associated with filing past reports and/or filing a new registration statement.

It may be useful to note that going private transactions are not usually initiated by the shareholders who will lose the benefits of information provided by SEC compliance, but by management seeking to avoid the burdens. Although going private transactions may save company money, the long-term price to be paid in the form of shareholder dissatisfaction is yet to be determined in the biorefining industry.

Author: Danielle D. Smid Attorney, BrownWinick (515) 242-2476 smid@brownwinick.com

february 2011 | Biorefining Magazine | 9

business briefs People, Partnerships & Deals

JBI Inc., the waste-plastic-to-fuel company, announced the appointment of James Fairbairn to its board of directors. Fairbairn is a self-employed chartered accountant, consulting for public companies since 1990 and a member of the Institute of Corporate Directors. He is a current officer or director at a number of TSX Venture Exchange listed companies. His experience in public accounting and corporate governance will be a strong asset for JBI’s board of directors, the company states. Fairbairn graduated from the University of Western Ontario and received his Chartered Accountant designation in 1987.

10 | Biorefining Magazine | february 2011

SG Biofuels, a bioenergy crop company using breeding and biotechnology to develop elite seeds of jatropha, recently announced it has named Miguel Motta as vice president of marketing and strategy. Motta joins SG Biofuels following a distinguished career at Monsanto Co., most recently serving as marketing director for Europe, Middle East and Africa. At SG Biofuels, Motta will direct marketing and business strategies guiding the company’s growth in key markets including Latin America, India, China, Southeast Asia and Africa. “Motta’s vast experience driving global market expansion and revenue growth for Monsanto will be extremely beneficial as we enter new markets and expand our product and service offerings,” says Kirk Haney, president and CEO. As marketing director at Monsanto, Motta developed and implemented commercial business plans, including product portfolio strategy, pricing and volume targets, distribution and brand strategy and marketing programs covering operations in more than 30 countries.

Glycotech Inc. has signed a manufacturing contract agreement with Emeryville, Calif.-based biotech firm Amyris Inc. to provide chemical processing at a plant in Leland, N.C. The Leland facility, owned by Salisbury Partners LLC, will convert Amyris’ biofarnesene—called Biofene—into finished bioproducts that can be used for a variety of applications. According to Jeryl Hilleman, Amyris’ chief financial officer, the company will ship biofarnesene produced from its two contract manufacturers—Biomin GmBH in Piracicaba, Brazil, and Tate & Lyle’s bulk ingredients operations in Decatur, Ill.—to the Glycotech facility in North Carolina where it will provide finishing services for renewable products such as industrial lubricants, polymers and renewable diesel. Farnesene is an isoprenoid molecule that serves as a platform molecule to produce a wide range of products varying from specialty chemical applications to transportation fuels such as diesel.

In January, John Atanasio was appointed president and CEO of Alfa Laval Inc., a global provider of specialized products and engineering solutions based on its key Separation Expertise technologies of heat New president and transfer, separation CEO of Alfa Laval, John Atanasio, has and fluid handling. In nearly four decades of this role, Atanasio is separation technology experience. responsible for leading Alfa Laval in the U.S. to drive profitable growth in its markets, leveraging the company’s key technologies of heat transfer, separation and fluid handling. Atanasio joined Alfa Laval in 1982 in the company’s Food and Dairy Group. He joined Alfa Laval Separation in 1990 where he held a number of positions. In 2001, Atanasio was named president of Alfa Laval USA’s Parts and Service Division, and then president of the company’s Equipment Division in 2004. Most recently, Atanasio served as president of the Hygienic and Marine group of Alfa Laval Inc. Prior to joining Alfa Laval, he held a number of positions at Westfalia Separator.

PHOTO: THE SAMUEL ROBERTS NOBLE FOUNDATION

Butamax Advanced Biofuels LLC filed a patent infringement lawsuit against Gevo Inc. in January for its use of Butamax biobutanol technology. The lawsuit was filed in U.S. Federal District Court in the District of Delaware. Butamax patent 7851188, granted in December, encompasses biocatalysts developed to produce isobutanol and provides protection for Butamax and its work in this field. Butamax has filed an extensive patent portfolio for its Protecting IP Butamax CEO Tim proprietary technoloPotter says patents gy across the biofuels must serve as protection in the best value chain including interests of advanced biocatalyst, bioprocess biofuel development. and fuels. A number of patent applications by Butamax have been successfully accepted into the U.S. Patent and Trademark Office Green Technology Pilot Program for accelerated review. “The U.S. patent system is designed to encourage research and development and to protect inventions,” says Tim Potter, Butamax CEO. “Butamax and its owners were the first to develop this technology and it is our belief that the protection of intellectual property serves the best interest of the biofuels industry, our customers and the U.S. energy policy.”

Flip the Switch Huanzhong Wang (left) and Richard Dixon led the gene work at the Samuel Roberts Noble Foundation.

A new gene discovery made by a team of plant research scientists at The Samuel Roberts Noble Foundation “clearly looks like a way of essentially producing more biomass and giving a greater source of fermentable sugar per acre,” according to lead researcher, Richard Dixon, director of the Noble Foundation’s Plant Biology Division.

business briefs |

Riverdale Capital Ltd. has completed its acquisition of Nevada-based WSPVA Bio Products International LLC. Riverdale Capital now retains 100 percent ownership of WSPVA, which holds an exclusive license to develop and market a polyvinyl alcohol (PVA) film known as “dissolving plastic” through a patented machine technology in North America. According to Aslan Halim, a consultant with Riverdale Capital, the PVA film is made from 100 percent starch-based alcohol. While some bioplastics companies use oils or additives to produce the material, Halim said WSPVA’s licensed process does not. The material is stronger than more traditional ethylene-based plastics. It is also very stable and can be dissolved in water. Initial commercial production of the bioplastic is scheduled to begin during the first quarter of 2011 in China, where the process was developed. An existing pilot-scale facility is being scaled-up to an annual production capacity of 60,000 metric tons, Halim says.

Biosuccinic acid and bioproducts producer BioAmber, formerly DNP Green Technology, has partnered with Cargill

Inc., resulting in BioAmber having the exclusive worldwide rights to Cargill’s novel fermentation technology platform to produce biobased succinic acid from an array of nonfood-based lignocellulosic feedstocks. The partnership with Cargill is part of BioAmber’s near-term objective to build biobased succinic acid plants in North America, Brazil and Asia. According to Mike Hartmann, vice president of corporate affairs for BioAmber, the company intends to add the technology licensed from Cargill to its proprietary fermentation platform in future commercial-scale biobased succinic acid facilities currently under development.

The key to Cargill’s technology, according to Hartmann, is a highly efficient microorganism that can significantly increase output volume and performance.

A team of researchers funded by the Energy Biosciences Institute, a BP-led program, has engineered a new yeast strain that will improve cellulosic fer mentation times by almost 40 percent. The ”G”engineers Suk-Jin Ha (left), collaboraYong-Su Jin, (center) and Soo Rin Kim helped to engineer the new tive effort yeast strain. through PHOTO: L. BRIAN STAUFFER, UNIVERSITY OF ILLINOIS NEWS BUREAU the University of Illinois, the Lawrence Berkeley National Laboratory and the University of California began working on the new yeast strain roughly one year ago. Now, food science and human nutrition professor at the University of Illinois, Yong-Su Jin, says the team has created a yeast that contains five different enzymes that make cofermentation of both glucose and xylose more efficient.

“Standard fermentation (with standard yeast strains) is like giving a piece of chocolate and some broccoli to a kid,” Jin says. “The kid will eat the chocolate first and the vegetable later.” The new strain Jin’s team has devel-

oped combines the chocolate and vegetable together so the kid doesn’t know the vegetable is there, Jin says.

PHOTO: QTEROS

The gene discovery, which can be attributed to an initial interest at the foundation in devising methods to improve forage quality in alfalfa, was found after the team began analyzing mutated alfalfa plants that had altered patterns of lignin deposition. What the team had, Dixon explains, was an alfalfa plant in which a gene had been knocked out, and that was causing this increase in cell wall material throughout the stem. The team decided to look at another readily researched plant, Arabidopsis, and test their findings. The work shows that by knocking out a single gene it is possible to increase the amount of lignin, cellulose and hemicellose amounts in a plant, he says.

Forerunner Qteros president and CEO John McCarthy says his company has been working with Praj for 10 months on an experimental basis.

Marlborough, Mass.-based cellulosic ethanol technology developer Qteros Inc. and India-based engineering and design firm Praj Industries Ltd. have formed a strategic partnership to accelerate the commercialization of cellulosic ethanol production. The partnership agreement, according to Qteros president and CEO John McCarthy, was the result of a culmination of collaborative work between Qteros and Praj, which will allow both to aggressively roll out its commercial strategy. “We’ve been working with Praj for nine to 10 months now on some experimental work that we’re doing with some of their pretreatment materials, feedstocks and our technology platform, as we have done with a number of other players in the market,” McCarthy says. The partnership, according to McCarthy, is structured around a joint development program that will span roughly the next 18 to 24 months where Qteros will retrofit Praj’s existing fully integrated pilot ethanol facility in Pune, India, and use that as the foundation to deliver fully integrated engineering design packages.

Share your industry briefs To be included in Business Briefs, send information (including photos and logos if available) to: Industry Briefs, Biorefining, 308 Second Ave. N., Suite 304, Grand Forks, ND 58203. You may also fax information to (701) 7468385, or e-mail it to rkotrba@bbiinternational.com.

Please include your name and telephone number in all correspondence. february 2011 | Biorefining Magazine | 11

startup

Biorefining News & Trends

Genomatica’s Secret Sauce Every successful company has a “secret sauce,” and Genomatica, a California-based sustainable chemicals producer, certainly has one. By the company’s own accounts, it doesn’t make 1, 4 Butandiol (or BDO as its called) through costly brute force or trial-and-error techniques. “We’ve got a unique technology platform,” says Christophe Schilling, founder and CEO of Genomatica. “That has allowed us to come up with the best ways to produce many of the intermediate chemicals that are used for the core of the chemical industry.”

And what is Genomatica’s approach to making biobased chemicals? The answer is computer modeling.

Nearly all of the company’s early success has come via predictive computer modeling for living organisms and their respective metabolic rates. The computational approach “has allowed us to figure out all the ways we want to make the chemicals,” Schilling says, and for BDO, “we can figure out every way possible to turn sugar into BDO.” Today, the company is using a tried-and-true industrial organism, E.coli, and a readily available feedstock, dextrose from corn wet mills and sucrose from sugar mills, to produce what the company says is the first of many products. Don’t ex-

pect Genomatica’s predictive modeling approach to pump out any novel chemicals for new and future markets, however.

Schilling says the company is focused only on the core chemical industry. “We think it is the perfect combination of volume in the market with margin,” he says. “We think that specialty chemiNeed to Guess Genomatica’s BDO is made from dextrose or sucrose, and cals are nice in terms of No a computer modeling system. greater dollar per pound, but the markets are relatively small.” From ethanol, a margin that makes up for the difSchilling’s standpoint, venture-capital-type re- ference in market size. That market opportuturns just can’t happen in those markets. And, nity doesn’t mean Schilling and his team aren’t on the other end of the spectrum is the enor- keeping an eye on the ethanol industry, espemous biofuels market, an “alluringly large mar- cially developments in cellulosic. Because the ket,” Schilling says, which requires massive pro- company is determined to take a feedstockductions levels in relatively thin margins. “We flexible approach, Schilling says Genomatica think the sweet spot is right in the middle.” is constantly monitoring progress in the field That rationale is based on two pounds— and looking for companies to partner with on from two pounds of sugar, Schilling says, a pretreatment technologies before it reaches person can make roughly the same amount of its ultimate goal, syngas utilization to produce both BDO and ethanol. BDO, he points out, sugars. —Luke Geiver sells for about two to four times as much as

Sustainable Packaging Practices Are Here There’s more to Bubble Wrap than popping, thanks to Ecospan Dextrose sugars from corn are helping computers, cameras and other sensitive equipment pieces get from point A to point B, and thanks to Ecospan, a biomaterial science and technology company that makes a number of bioplastics, moving from A to B has nothing to do with fuel. The California-based company produces smartcards, biobags, cups, and among others, new biopolymer-based packaging wrap.

It all starts in Nebraska, at a 300 million pound biobased material production facility called 12 | Biorefining Magazine | february 2011

Natureworks LLC, an independent company owned by ag-giant, Cargill. “Ecospan is basepolymer-neutral,” the company says, “meaning that Ecospan is capable of using different base biopolymers for its value-added solutions.”

But until other alternatives become available, the company says, Ecospan will continue using a Natureworks product called Ingeo. The corn-based Ingeo is made by fermenting dextrose with microorganisms that create lactic acid and then form long chain lactide mono-

mers. Through polymerization, the chains then form polylactide polymers, which are then pelletized. Ecospan combines the Ingeo product with other compostable materials, and through a series of common plastic-forming processes like calendaring and thermoforming, Ecospan then engineers a product that can help those sensitive packages go from one place to another, wrapped and protected in a sustainable way. —Luke Geiver

PHOTO: GENOMATICA

A predictive computer model gave Genomatica a process and clear plan

startup |

Flying Forward

significantly higher conversion efficiency of 50 percent. Logos Technologies Inc. has been named by DARPA as a contractor in the program.

The Phase 1 requirements for the algae component of the program are slightly different. Contractors initially have to dem- Driving Development The U.S. Department of Defense is one of the largest consumers of petroleum fuels in the world. The development of biobased alternatives onstrate algal triglyc- will not only benefit the environment, it will also help guard against the rising price of eride production at a oil while increasing energy security. projected production cost of $2 per gallon. Algal triglycerides are awarded Phase 2 participation in cellulosic a precursor to biobased JP-8. Participants component of the program.

“While fully compatible jet fuel proin the program must also demonstrate an affordable process for the conversion of duced from cellulose offers many advantages algal triglyceride into JP-8. Contractors are over other sources, its production demands required to deliver a 100-liter sample of jet more complicated processing than do curfuel by the time Phase 1 is complete. The rent biofuel production approaches,” says sample will be used for government testing Logos Technologies CEO Greg Poe. “We and evaluation activities. A larger 4,000-liter and our BioJET team have shown that jet sample must be delivered upon the pro- fuel can be produced economically and efgram’s completion. General Atomics and ficiency from cellulosic biomass feedstock.

Science Applications International Corp. We look forward to continuing this imporhave been named by DARPA as contractors tant program with DARPA.” Significant benchmarks are expected to for the algae component of the program.

While General be reached under the program this year. AcAtomics and Sci- cording to DARPA, the first demonstrationence Applications scale production of biobased JP-8 under the International told program is expected to begin in 2011. The Biorefining Magazine transition to industrial-scale production is they are unable to scheduled to be complete in 2013. Within comment on the that timeframe, the conversion of cellulosic status of their par- biomass into JP-8 is expected to exceed the ticipation in the required 50 percent conversion efficiency, program, due in while algae oil production is anticipated to part to confiden- approach $1 per gallon when produced in tiality agreements ideally suited locations. —Erin Voegele with DARPA, Logos Technologies has officially been source: Defense Advanced Research Project Agency

While agriculture and aquaculture both show promise as feedstocks for the production of military-grade jet fuel, also known as JP-8, current production processes have proved inefficient and prohibitively costly for large-scale use. In order to expedite the development of more economically feasible biobased jet fuel, the U.S. Defense Advanced Research Projects Agency kicked off a new research project in 2010.

The agency’s Cellulosic and Algal Biofuels program aims to develop affordable alternatives to petroleum-based JP-8 from two specific sources: algae and cellulosic biomass. To this end, the program has been designed with a strict financial stipulation. Biobased jet fuel must be produced at a cost that is competitive with traditional JP-8. More specifically, the agency is targeting process technologies that can produce biobased JP-8 at a cost of less than $3 per gallon when produced on a moderate scale.

A moderate scale is considered to be less than 50 MMgy. Contractors participating in Phase 1 of the cellulosic component of the program were required to demonstrate 30 percent conversion energy efficiency, by energy content, of feedstock into JP-8. Participants accepted into Phase 2 need to demonstrate a

february 2011 | Biorefining Magazine | 13

PHOTO: U.S. Department of Defense

DARPA leads another military-grade biobased jet fuel project

|

startup

A Name to Know

A pine-based chemical producer is leading the way

Look at the Green Nearly every product made from Arizona Chemical creates a smaller carbon footprint than similar products.

Don’t let the name fool you. Arizona Chemical Ltd. is a global company with more than 1,000 employees spread throughout six countries. As a leading refiner of crude tall oil (CTO), a coproduct of the wood pulping process, the company has another impressive statistic. The biorenewable content of most of Arizona Chemical’s products achieves nearly 75 percent, a number that, according to the company, has been third-party verified

by ASTM D6866 testing standards. “We are not just a chemical manufacturer based on forest products,” says Kees Verhaar, president and CEO. “We are uniquely positioned to deliver low-carbon, highly sustainable solutions to the marketplace.”

Arizona Chemical has manufacturing facilities in Netherlands, the U.K., Sweden, Finland, and the U.S. that make a wide array of products. The company produces biolubricants that range from monomer acids used in hydraulic oils and metalworking fluids, and 14 | Biorefining Magazine | february 2011

isotearic acids for industrial gear oil and two stroke oils, to distilled tall oil for surfactants in metal working fluids and fatty acid esters as lubricant greases. The majority of the products are pine based, and nearly all reach greater greenhouse gas (GHG) emissions reductions than the equivalent products on the market, according to the company. “Our business is based on a renewable and elegant idea,” Verhaar says, “but we must continually challenge ourselves to improve our sustainability.”

To meet that challenge, the company uses pitch fuel, a byproduct of the CTO made through distillation, as an energy source. When distilled, the company notes, CTO yields 30 to 50 percent pitch fuel, which can be used for industrial energy and heating processes. The company produces its version of the fuel, called Sylvablend, which Arizona Chemical says generates 70 percent lower GHGs than similar fuels.

SOURCE: ARIZONA CHEMICAL LTD.

The company’s work with CTO, pitch fuel and a number of biobased chemicals isn’t slowing down either. In Savannah, Ga., and Almere, Netherlands, the company has technology centers with more than 50 scientists working on pine chemistry. It should come as no surprise that the company is a global force in the pine chemical production sector. It was begun in 1930 in Camp Verde, Ariz., by a paper company, and in 1936 began processing tall oil and turpentine at plants located in Florida and Louisiana. By 1946, the company had developed a distillation technology adapted from fractionation of crude petroleum streams. In 1956, the company created a hydration reaction technology and others like desulfurization for alpha-pinene that would make pine oil with a “more pleasing odor,” according to the company. Today, Arizona Chemical produces everything from chemical intermediates to rubber for tires.

—Luke Geiver

startup |

Linking Up

How alignment of interests are furthering biorefining industry growth A recent spike in joint ventures, acquisitions and supply chain partnerships in the biorefining industry have come to a head in early 2011—a clear indication that technology for second- and third-generation biofuels and biobased chemicals are closer to commercialization.

First, DuPont Co. acquired global enzyme and specialty food ingredients company Danisco for $5.8 billion in cash and assumption of Danisco’s $500 million net debt. According to DuPont, the acquisition is expected to close early second quarter and be cash and earnings accretive in 2012, which will be the first full year of the combined entity.

“Danisco has two well-positioned global businesses that strongCore Complement CEO Ellen Kullman ly complement our says DuPont’s current biotechnolacquisition of Danisco is expected to broaden ogy capabilities, R&D DuPont’s biotech pipeline and specialty capabilities. food ingredients, a combination that offers attractive long-term financial returns,” says DuPont CEO Ellen Kullman. “This also will create new opportunities across other parts of the DuPont port-

folio, including traditional materials science offerings.”

Elsewhere, DSM Pharmaceutical Products, the custom manufacturing organization of Royal DSM N.V., and Codexis Inc. signed an enzyme supply arrangement. The agreement grants DSM rights to use Codexis’ custom biocatalysts and services, and secures supply of Codexis enzymes for commercialization of sustainable enzyme-based pharmaceutical manufacturing routes developed

by DSM’s InnoSyn route scouting services.

The DSM InnoSyn route scouting team integrates novel enzyme technology with a full range of advances in synthetic methods such as homogeneous catalysis, modern organic synthesis and continuous chemistry. Codexis’ technology enables the development of new efficient manufacturing processes for active pharmaceutical ingredients and intermediates that reduce cost and environmental waste.

The company’s technology is used at major pharmaceutical and chemical companies worldwide, including Merck, Pfizer and Teva.

Meanwhile, Valero Energy Corp. signed a nonbinding letter of intent to support the construction of Macoma Corp.’s proposed 40 MMgy wood-based cellulosic ethanol production facility in Kincross Charter Township, Mich., which is slated to break ground

this year. Under the terms of the agreement, Valero plans to invest up to $50 million of the equity required to finance the project through Frontier Kincross LLC, a subsidiary Commercial Ready of Mascoma’s operatCEO Bill Brady says ing subsidiary Frontier Mascoma’s off-take arrangement with Renewable Resources Valero proves it is LLC, and would enter ready to commercialize into an off-take agreecellulosic ethanol. ment to purchase the facility’s future ethanol product.

“Valero’s proposed investment in our first commercial-scale production facility proves the economic practicality of Mascoma’s technology for the conversion of woody biomass into ethanol,” says Bill Brady, CEO of Mascoma. “We are also thrilled to have Valero as a shareholder in Mascoma as there are many synergies even beyond the Kincross facility where the technologies we have developed could be helpful to Valero’s business.”

Over the past two years, Mascoma has demonstrated the commercial viability of its conversion technology at its 200,000 gallon per year facility in Rome, N.Y. —Bryan Sims

Raising the Price

Increased input costs translate to higher price Columbus, Ohio-based Momentive Specialty Chemicals Inc. is increasing the price of several powder polyesters, including AlbecorBio, in the European, Middle Eastern and African markets. Effective since Dec. 22—or as soon as established contracts allow—the price for these materials will rise from 0.08 euros per kilogram to 0.10 euros per kilogram (approximately 18 to 29 cents per pound). The price adjustments are attributed to the continued increased cost of key raw materials.

Albecor-Bio is a family of soy-based, low

temperature, cure powder coatings. The products, which were announced in mid-2009, are suitable for use on a wide variety of materials, including metals and heat sensitive substrates.

Through the bioderivate used to produce Albecor-Bio, the system’s novel polyester enables high reactivity and physical properties such as flow and outdoor durability.

The material was originally developed by Hexion Specialty Chemicals Inc., which has since merged with Momentive. The United Soybean Board played a role in supporting

the launch of 32 new soy-based products last year, including Albecor-Bio. “So many soy-based products replace petroleum-based chemicals,” says Bob Haselwood, chairman of the USB New Uses program. “Soybeans represent a renewable resource. We grow soybeans every year, so they are a renewable feedstock.” —Erin Voegele

february 2011 | Biorefining Magazine | 15

|

startup

Steaming Ahead with Cellulosic Ethanol A new industrial park under development

by GRE near Jamestown, N.D., features a combined heat and power (CHP) plant designed specifically to supply process steam to adjacent industrial processors. The project, known as Spiritwood Station, was originally intended to host a 100 MMgy corn ethanol plant. Plans have since changed, and a new 20 MMgy cellulosic biorefinery is expected to be built in its place.

“Back in the 2007-‘08 timeframe, when we were just breaking ground on the [CHP] plant, the conventional ethanol plant was cancelled,” says GRE’s Manager of Business Development Sandra Broekema. “That left us with a big hole of 350,000 pounds-per-hour of steam that we were planning to produce for sale that we now need to find a home for.”

Broekema says there are several reasons why a cellulosic biorefinery is a well-suited addition to Spiritwood Station. In addition to the plant’s high-steam usage requirements, the facility will also produce purified lignin pellets as a coproduct. “Our CHP is a fluidized bed combustion system which has some inherent fuel flexibility,” he continues. “By cofiring 10 percent lignin with DryFine (a refined North Dakota lignite), we would be able to reduce our carbon footprint even further.”

As a result GRE has stepped into the lead development role of the cellulosic ethanol plant. “The primary motivation for GRE’s

involvement is to secure additional steam partners for the industrial park in order to achieve our original design efficiencies and economies for our cooperative membership,” Broekema says. “Because we are taking a ‘cooperative approach’ involving as many New Plan The Great River Energy biorefinery will utilize steam produced of the key stakeholders as we at Spiritwood Station’s CHP plant and produce purified lignin pellets as a can, we have laid out a some- coproduct. what conservative five-year development plan bicon A/S. “Inbicon has developed the core beginning in 2010 through 2014 startup, if all technology that this plant is based on,” Broekegoes according to plan.” ma says, noting that the company is a member According to Broekema, GRE is expected of the development team working to pull the to maintain a small, minority interest in the project together. It is also possible that Inbicon product as both a buyer and seller of steam and may choose to hold a minority interest in the fuel. “[We’re also] trying to involve as many of plant. the key stakeholders in this area as we can, beWhile wheat straw was originally intended cause we recognize that this first commercial- to be the primary feedstock for the plant, it is scale plant is going to need all the support it possible that corn stover will also have to be can get,” she says. “I envision that there will utilized. A feedstock supply and product marbe many owners. I’m not sure there is going ket study was recently completed. While GRE to be a single majority owner. It may be that was generally pleased with the outcome of the a cooperative is formed with many individual study, there was one snag. It may not be poskey stakeholders and that will be the majority sible to harvest more than 25 to 50 percent of owner of the plant. However, I definitely see the wheat straw grown on highly erodible land. it as broad ownership—primarily local and re- As a result, it may be necessary to consider gional entities and feedstock producers.” adding corn stover to the feedstock mix while The current plan is to license the facility’s pushing the feedstock procurement radius out process technology from Denmark-based In- to nearly 150 miles. —Erin Voegele

Applying Cancer Research to Algae Production How metabolism strategies in tumor cells can affect lipid production If metabolic disruption (MDT) is truly successful, it will be able to interrupt metabolic strategies used to regulate a cell’s energy consumption, production and storage. A cell that is dividing will have a different energy level than one that is not, and will use an alternative metabolic strategy, according to Viral Genetics, a biotechnology research company. And “the way a cell metabolizes its sources of energy appears to determine whether it will survive the most common treatments for cancer,” chemotherapy and radiation, the company says.

16 | Biorefining Magazine | february 2011

M. Karen Newell-Rogers of Viral Genetics has been working on MDT research, and she recently received $750,000 to develop the technology. The work to this point indicates that when tumor cells’ metabolic strategies are interrupted, the cells can no longer generate energy needed to survive and the reduced energy levels reduce the tumor cells’ ability for repair, “resulting in a greater sensitivity to chemotherapy and radiation.”

The disruptive agents used to this point are comprised of pharmaceutical compositions that

interfere with high rate glycolysis and fatty acid oxidation. The DCA, or dichloracetate, sends a message to the cells that nutrient reserves are full and also interferes with an enzyme that triggers a switch in a cell to fatty acid oxidation in times of starvation. Viral Genetics is now venturing into another uber-important realm: biofuels. The company has launched VG Energy, to put the MDT approach to use in algae-based biofuels. The goal is to increase lipid production by “disrupting” the metabolic strategies of the algal cells. —Luke Geiver

PHOTO: GREAT RIVER ENERGY

Great River Energy leads new biorefinery project in North Dakota

startup |

A Sweet Proposition

How a new variety of starch-based catalysts could replace petroleum-based plastics Countries around the world are recognizing the need to replace plastics manufactured from a petroleum base with products derived from renewable raw materials that mimic their petroleum-derived counterparts. Moshe Kol, a professor at Tel Aviv University’s School of Chemistry in Israel, and his team believe they have found a solution to the problem. Using corn starch and sugar, Kol’s team has developed a new variety of catalysts that could help sustainable plastics compete in the marketplace.

The research is currently expanding its activities in partnership with the University of Aachen in Germany and the University of Bath in England.

Specifically, Kol’s research involves developing a new variety of catalysts for the polymerization of lactide—the cyclic di-ester of lactic acid—to produce polylactic acid (PLA), a common building block molecule already used in a variety of consumer products such as plastic bottles, bags and films. According to Kol, he and his research group are designing multidentate ligands and are attempting to decipher their wrapping tendencies around various metals such as zirconium, hafnium and titanium, noting that the highest number of lactide equivalents to metal employed thus far is 2,000-to-one.

“A ligand that wraps in a specific manner around a metal center yields a metal complex

with well-defined active sites, which in turn will lead to a specific growth chain,” Kol tells Biorefining Magazine. “Another important parameter is the ability to control the dynamic behavior of the metal complex. These parameters will affect the type and degree of tacticity of the obtained PLA.” For example, Kol says, heterotactic PLA is obtained by the alternating insertion of d-lactide and l-lactide from racemic lactide unto a growing polymeryle chain. The common mechanism includes a static nonchiral metal complex and a chain-end control of insertion of the opposite enantiomer.

“However, some catalysts are known to be chiral and fluxional and invert chirality between every monomer insertion,” Kol says. “Some of the catalysts that we are designing include a combination of rigidity and fluxionality with ‘dialed-in’ rates for inversion of chirality, with the attempt of controlling the PLA tacticity.”

For Kol, work on the development of new varieties of catalysts for lactide polymerization reactions came to fruition as a result of 10 years of work he and his team had been doing on tetradentate-dianionic ligands, which have been applied mostly for alpha-olefin polymerization, in particular, the isospecific polymerization of propylene and higher monomers.

“A crucial aspect for us is the accessibility

of the ligands,” Kol says. “We design ligands that will be easily synthesized in very few steps (from one to three) from readily available starting materials so that their commercial application would be viable.”

Although more work is planned, Kol says, preliminary results look promising, adding that the plastics in the lab look and feel like polystyrene. Patent applications regarding the various types of catalysts are ongoing.

“The catalysts giving the best reactivities under industry-relevant conditions will be developed further,” he says.

In the context of lactide polymerization, Kol admits he’s not the first to work in this direction, but adds that he’s hopeful his catalyst development will encourage others to delve into this area to introduce other novel methods for producing sustainable and other ecofriendly plastics.

“PLA products made by polymerizing lactide have been on the market for some time now,” Kol says. “We hope that by proper catalyst design and by taking advantage of various forms of lactide and other cyclic esters as monomers we will be able to introduce new polymer architectures and consequently polymers with improved properties.”

—Bryan Sims

Meals for Malnourished Microbes Luca Technologies proves that not all microbial work relates to biofuel Not every company working with microbials is destined for biobased product stardom.

Luca Technologies, a Colorado-based company, has found a different technology that involves microbes, and although the goal of the company still revolves around energy, Luca’s work certainly shows that not all microbe-related news is based on biofuels. The idea behind Luca’s technology is centered on depleted coal, gas, oil or shale reserves. After years of drilling, anaerobic microorganisms present in the formations are exposed to oxygen caused by dewatering and, deprived of needed nutrients in most cases, these conditions eventu-

ally cause the demise for those locations. Over time, the microbes return, according to Luca, but the microbe revitalization process developed by Luca can speed it up and regenerate once-shuttered and abandoned sites.

To restore a site, Luca takes a sample of water still present and replenishes the water with nutrients that range from calcium and magnesium chlorides to polyoxyethylene. The water is then reintroduced into the original site, a step performed multiple times at multiple wells on each site. The nutrients help the microbes that produce natural gas to reactivate and, after a “dwell period,” or roughly one

month that allows the microbial populations to restart, according to Luca, the sites should begin producing natural gas once again.

The process certainly sounds innovative and loaded with potential, and partners like BASF seems to agree. Previously, Luca was working to put the process to use in Wyoming’s Powder River Basin, but due to issues unrelated to the technology, the plans were stopped. But the novel work proves that not all microbial work in the energy sector is about producing biofuels or biobased chemicals.

—Luke Geiver

february 2011 | Biorefining Magazine | 17

|

startup

First of its Kind

Louisiana will soon be home to the world’s largest biobased succinic acid plant A commercial biobased succinic acid production facility is coming to Lake Providence, La. In December, Gov. Bobby Jindal publicly recognized Quincy-Mass.-based Myriant Technologies’ endeavor as the project is expected to create 176 new jobs along with an estimated $80 million in new capital investment.

The plant is in a region that’s in great need of economic development, says Sam Perfect Fit McConnell, senior Myriant’s biosuccinic acid plant will use grain vice president of corsorghum and carbon porate development dioxide as feedstock, says vice president with Myriant. “That’s Sam McConnell. a nice plus for them, but it’s also a site that provides great logistics for us. So, it’s a perfect match from that standpoint.”

Expected to break ground in February, the future facility will use grain sorghum and

carbon dioxide to produce 30 million tons of biobased succinic acid annually. When it comes online during the first half of 2012, the plant will be the world’s largest biobased succinic production facility. Biobased succinic acid can be used to produce an array of chemical products, including 1,4-butanediol, tetrahydrofuran and as a substitute for adipic acid.

Through its wholly owned subsidiary Myriant Lake Providence Inc., the future 392,000 square-foot facility will be built by full-service engineering, procurement and construction operations firm CH2M Hill along with Uhde GmBH acting as the subcontractor. Shortly after commercial operation, according to McConnell, the company intends to expand production output to 150 million pounds.

According to McConnell, Lake Providence was an ideal location due to its combination of existing ship, rail and highway infrastructure, which provides the company a variety of feedstock options as well as low-

cost transportation choices for both inputs and outbound product.

“It gives us great feedstock flexibility as well as the ability to direct barges right into the Houston Ship Channel without transloading,” McConnell says. “That’s a great transportation advantage for us.”

The project will benefit from funding provided by U.S. DOE and by the Louisiana Department of Transportation and Development to the Port Priority Program. Additionally, the Louisiana Development provided an incentive package that included turnkey workforce solutions from LED FastStart, a 5 to 6 percent rebate on payroll expenses and certain sales taxes through the Quality Jobs program, and property tax abatements for materials used in new manufacturing through the Industrial Tax Exemption Program.

“We think we have leading technology,” McConnell says. “It’s a market that can support a lot of production and that’s a good thing.” —Bryan Sims

Redeploying Residue Farms in Malaysia and Indonesia produce approximately 90 percent of the world’s palm oil, creating nearly 40 million metric tons of residue known as “empty fruit bunches” (EFB) annually. The long-term stable supply of EFB is one reason the research and development division of palm oil producer Sime Darby and Mitsui Engineering and Shipbuilding Co. Ltd. are partnering to construct and operate a demonstration-scale cellulosic ethanol plant in Malaysia.

The facility is being developed adjacent to Sime Darby’s Tennamaram Oil Mill. Once complete, the plant will be able to process approximately 1.25 metric tons of EFB per day.

As part of the ongoing research activities at the facility, operational data will be gathered to verify the production technologies and processes. The data collected at the demonstration plant will aid Sime Darby and MES 18 | Biorefining Magazine | february 2011

in establishing a commercial-scale cellulosic biorefinery. According to the two companies, development on the commercial-scale plant will begin as soon as possible.

Through Japan’s New Energy and Industrial Technology Development Organization Joint Project, MES has been actively working to develop technology Utilizing Waste A proposed cellulosic biorefinery in Malaysia has for cellulosic ethanol production. been specifically designed to process locally available waste biomass.

Empty fruit bunches are a waste material produced as a byproduct of The company has also entered palm oil processing. into a license agreement with Denmark-based Inbicon A/S after a year of proprietary technology and Inbicon’s biomass working cooperatively. The agreement per- refinery technology. The resulting ethanol is tains to Inbicon’s biomass refinery technology, expected to be used as both a blendstock for specifically its hydrothermal pretreatment and gasoline and as an input for the chemical inenzymatic hydrolysis methods. The new dem- dustry. —Erin Voegele onstration-scale project will utilize both MES’

PHOTO: National Renewable Energy Laboratory

Palm waste to feed cellulosic ethanol plant in Malaysia

startup |

Far East Biofiber Tokyo, Japan-based Teijin Fibers Ltd., the core company of the Teijin Group’s polyester fibers business, plans to launch the world’s first commercially produced plantbased polyethylene terephthalate (PET) fiber by April 2012. The new biobased PET product, called Eco Circle PlantFiber, will also be available in a textile and will become Teijin Fibers’ core biomaterial for applications ranging from apparel, car seats and interiors, to personal hygiene products. The company expects to sell 30,000 tons of Eco Circle PlantFiber products in the initial fiscal year ending in March 2013, and 70,000 tons by the third year of business.

The new material will be roughly comprised of 30 percent biofuels from sugarcane sourced from Brazil, according to

Teijin Fibers. Typically, PET is produced of dimethyl terephthalate for raw feedstock by polymerizing ethylene glycol and di- supply. —Bryan Sims methyl terephthalate or telephthatlic acid, with ethylene glycol accounting for roughly 30 percent. The ethylene glycol contained in Eco Circle PlantFiber will be biobased rather than petroleum-derived. An added benefit, according to Teijin Group, is that it can be recycled in the company’s Eco Circle closed-loop polyester recycling system in which it chemically decomposes the Plastic By 2012, Teijin Fibers’ biobased PET, coined Eco material at the molecular Plentiful Circle PlantFiber, will be available in a textile and will also become core level, creating a new source biomaterials for many different applications.

Guaranteeing a Biorefining Future USDA issues conditional commitment to Florida project under 9003 program

Vero Beach, FL

The U.S. DOE’s loan guarantee programs have been criticized as slow and inefficient. Through its program, however, the USDA seems to be stepping up support for the biorefining sector. In January, the department issued a conditional commitment for a $75 million loan guarantee to a joint venture project being developed by Ineos Bio and New Plant Energy LLC. The joint venture project is known as Ineos New Plant BioEnergy.

Ineos is the world’s third largest chemical company.

The USDA’s 9003 loan guarantee program is designed to provide guaranteed loans for the development and construction of commercial-scale biorefineries. The program can also support the retrofit of existing facilities to use eligible technology for the development of advanced biofuels.

The loan guarantee issued to the joint venture will be used to construct the Ineos BioEnergy Center. The planned site for the project is near Vero Beach, Fla. Once complete, the facility will have an 8 MMgy production capacity. It will also produce 6 megawatts of renewable power.

The facility will employ a patented anaerobic fermentation technology developed by

Ineos Bio in which naturally occurring bacteria convert gases derived from biomass directly into ethanol. One benefit of the process is that it is feedstockflexible, meaning the facility will be able to produce ethanol from multiple biomass sources, including construction waste, municipal solid waste, and forestry and agricultural residues.

Site preparation and construction of the facility are already underway. The center is expected to begin production in 2012. In addition to the USDA loan guarantee, the joint venture has also received a $50 million cost matching grant from the DOE. —Erin Voegele

february 2011 | Biorefining Magazine | 19

PHOTO: TEIJIN FIBERS LTD.

How one Japanese fiber manufacturer readies to introduce biobased PET

|

feedstock

Creating Confidence George Huber, chemical engineer at the University of Massachusetts-Amherst and co-founder of Anellotech Inc., believes his company’s technology will lead a new wave of pyrolysis players seeking to convert biomass into biochemicals without hydrogenation.

CREDIT: John Solem, UMass-Amherst

20 | Biorefining Magazine | february 2011

feedstock |

The

Bio-Oil

Barons

How pyrolysis oil is gaining traction as feedstock for heat, power, chemical and fuel applications

By Bryan Sims

Traditionally, petroleum crude oil is formed from the fossilized remains of dead plants and animals as a result of millions of years of exposure to intense heat and pressure found in the Earth's crust. This general theory has been accepted for centuries, passed on from one generation to another. Modern advancements in biomass conversion technology have brought on novel techniques, however, such as pyrolysis, that are capable of producing an oil product derived from renewable sources in a matter of seconds. The resulting product is referred to as bio-oil, bio-crude or even bioleum.

Pyrolysis is the thermochemical decomposition of virtually any type of agricultural or forestry biomass. It is performed at elevated temperatures, typically above 430 degrees Celsius (800 degrees Fahrenheit) in the

february 2011 | Biorefining Magazine | 21

|

feedstock

commonly used in the oil industry to selectively remove impurities such as sulfur, nitrogen and other metals. Since bio-oil contains a range of heavy and light compounds, it also includes a water-soluble aqueous phase that can be reformed by introducing methane and steam to produce hydrogen. Bio-oil could also be suitable for both hydrotreating at an oil refinery where hydrogen can be provided separately or via the stand-alone processing that employs the bio-oil aqueous phase to generate hydrogen.

Because hydrogenation is capital-intense, finding cost-effective methods to efficiently cap the acid must be addressed and overcome in order for bio-oil to penetrate the market as a readily available blendstock, according to Roman Wolff, president of Houston-based Enhanced Biofuels LLC. “Ultimately, if you’re going for transportation fuels, you’ll want to remove all the oxygen,” Wolff tells Biorefining Magazine, adding that oxygen typically makes up between 45 and 50 percent of the bio-oil by weight. “And if you’re going for heating oil or power generation, you’ll want to cap the acid so you don’t corrode your equipment.”

Wolff says his company has developed a proprietary reactor system that bolts onto existing industrial facilities, leverages exist-

While hydrogenation will likely continue to be a common route for many to stabilize biooil, ‘red mud’ could be an equally effective, if not more efficient, upgrading agent. ing infrastructure and utilizes an inexpensive alternative to hydrogen for reducing or eliminating the acidity of pyrolysis oil and other high-acid feedstocks. “Hydrogen doesn’t come cheap,” Wolff says.

Envergent Technologies, a joint venture between UOP, a Honeywell company, and Ensyn Technologies, licenses its patented Rapid Thermal Process technology so its customers can produce bio-oil to generate heat in industrial burners and electricity in specialized turbines, according to business director Monique Streff. “By the middle of this year, we hope to also prove the same for stationary diesel engines to generate electricity,” she says. “Our licensees will be able to build a stand-alone upgrading unit or they

PHOTO: ENVERGENT TECHNOLOGIES

absence of oxygen. Under these conditions, organic vapors, pyrolysis gases and a biochar byproduct are also produced. Proponents of the pyrolysis process view bio-oil as an attractive renewable alternative to petroleum-derived crude because of its versatility in a variety of applications such as industrial heat, power, biochemicals or electrical generation. It can also be used as a feedstock for further refining drop-in transportation fuels.

Before bio-oil can be used for any of these applications, however, a second stage to upgrade the oil is necessary to remove high concentrations of carboxylic acids and other oxygenated compounds, which render it highly corrosive and unstable.

Failure to upgrade Sound Advice Costly hydrogenation the bio-oil can make can be avoided by it difficult to store utilizing Enhanced Biofuels’ proprietary and transport. bolt-on reactor system, Common upaccording to president Roman Wolff. grade technologies used involve hydrogenation, hydro-deoxygenation and hydrotreating. Hydrogenation is an exothermic process

Commercially Ready Ensyn Technologies has designed, built and commissioned seven commercial RTP plants in the U.S. and Canada; the largest, located in Renfrew, Ontario, processes 100 metric tons of dry wood waste per day. Projects now under way will result in plants five to 10 times the size of the Renfrew plant.

22 | Biorefining Magazine | february 2011

feedstock |

can co-locate it with the RTP. Economies of scale would favor several RTP units to feed one upgrading unit.”

Envergent is currently engineering a working demonstration facility to deploy its RTP technology for heat and power applications, which is expected to come online by early 2012 in Hawaii, according to Streff, with the second phase of upgrading to transportation fuels set to be complete in 2013. Streff says that hydrogen will be a required step to upgrade the pyrolysis oil from its RTP units into biofuels. “There is yield loss across both the RTP unit and the upgrading unit,” Streff says, “but we are actually producing higher energy content materials in the production of transportation fuels.”

You start to reduce it to something that’s no longer red, so it’s no longer alkaline. The analysis we’ve done indicates that it’s no longer composed of hematite or goethite, but actually upgraded to magnetite, iron carbides and iron metal.”

During his discovery, Schlaf found that titanium dioxide—a white pigment and masking agent found in most paints and coatings—was a known catalyst for the decomposition of formic and acetic acid.

“Iron itself at sufficiently high temperatures

is a known Fischer-Tropsch and hydrogenation catalyst,” Schlaf says. “It turns out at 350 C you can do this.”

Schlaf estimates approximately 70 million tons of red mud is produced annually worldwide, with total global stock estimated at 1.3 gigatons per year. Schlaff ’s research has attracted the attention of global mining company Rio Tinto and a few other companies involved with pyrolysis oil production.

“We’ve demonstrated that the chemistry, in principle, works,” Schlaf says, “but

Improving the Upgrade

While hydrogenation will likely continue to be a common route for many to stabilize bio-oil, “red mud” could be an equally effective, if not more efficient, upgrading agent. Red mud is a high-alkaline waste byproduct of the Bayer process, which is used to refine bauxite into aluminum oxide. Marcel Schlaf, an associate professor of chemistry at the University of Guelph, discovered that when red mud is heated with bio-oil at 350 C, the process is shown to reduce acetic and formic acid, two acids that make up much of the acid content in bio-oil.

“The more formic acid is present, the less hydrogen you need because you can actually decompose the formic acid in situ to get hydrogen,” Schlaf says, adding that bio-oil upgraded through the red mud process has shown to be stable for at least 90 days. “What happens is that you really do stabilize the bio-oil, meaning it no longer forms a resin in the aqueous phase…it’s much less acidic. You essentially can get rid of all the formic and acetic acid and hydrogenate a good section of your carbonyls in it.”

“In the process,” Schlaf continues, “the alkalinity of the red mud is, of course, neutralized because the bio-oil is acidic. But then once that’s happening and you are reducing conditions, you actually also start to reduce your red mud. february 2011 | Biorefining Magazine | 23

feedstock

PHOTO: Domenico Dimondo, Schlaf Research Group, UNIVERSITY OF GUELPH

|

Changing Colors University of Guelph post-doctorate Elham Karimi holds red mud before the material goes through the process while Schlaf holds reduced magnetic nonalkaline gray red mud after processing.

whether the engineering and economics work, that’s an open question.”

Unique Routes Tailored to Market

There are several companies involved in pyrolysis oil production that employ unique routes tailored to desired conversion of various biochemicals or bioproducts.

Iowa-based Avello Bioenergy Inc. employs a novel separation technology developed by researchers from Iowa State University to produce pyrolysis bio-oil that can be used as alternatives to petroleum-derived materials in asphalt, as well as for biochemicals and industrial fuels. Avello currently operates a pilot plant at ISU under a contractual association. ISU has been working since 2007 under a $22.5 million, seven-year grant from ConocoPhillips, supPaving the Way Avello Bioenergy porting the university’s can isolate unstable research into the decompounds found in bio-oil, according velopment of pyroto President Dennis lytic bio-oils.

Benasiak.

24 | Biorefining Magazine | february 2011

The company has been approved by the Iowa Power Fund for a $2.5 million grant to build a 2.5 ton per day demonstration unit, which should break ground for construction within a year, says president Dennis Benasiak.

“Our approach is to try and separate a lot of the unstable compounds and issues directly out of the pyrolysis oil,” Benasiak says. “We fractionate the bio-oil, take the bulk of the acid in the water that’s formed into one fraction, and what we’re left with are fractions, concentrations of different chemicals that are more stable and easier to work with.”

New York-based Anellotech Inc. is an early-stage pyrolysis firm that uses a catalyst to produce finished products without hydrogenation upgrading. Anellotech can grind up biomass, dry it and then put it into a fluidized bed reactor that contains a circulating proprietary zeolite catalyst. Once the biomass is pyrolized, the vapors immediately enter the catalyst and are then converted directly into finished biobased aromatic products such as benzene, toluene and xylenes, or olefins like ethylene and propylene. According to George Huber, chemical engineer at

the University of Massachusetts-Amherst and co-founder of Anellotech, no bio-oil is produced, so there’s no need for hydrotreatment.

“We think this will be the process of the future everybody will be using for biomass conversion,” Huber says. “We can make refined products or we can make a range of refined products. We can tune the distribution of products we want to make.” Huber adds, “This is a $400 billion per year market we’re going after. We’re making products that already fit into the existing infrastructure that don’t need further refining.”

Huber adds that the company is working on refining the process for desired economies of scale. Anellotech is open to JVs to build its own plants or license the technology globally, according to Huber, and expects to have a commercial production plant online sometime by 2014. “The world is watching,” he says. “We’ve been given a lot of resources and we plan on solving this problem.”

Author: Bryan Sims Associate Editor, Biorefining Magazine (701) 738-4974 bsims@bbiinternational.com

www.grace.com

The Power of Grace

™

Produce ultra-dry ethanol with EnSieve® molecular sieve.

Because traditional distillation techniques fall short of drying ethanol to an acceptable level, water removal with molecular sieve adsorbents (zeolites) is the method of choice. In our pursuit of helping customers obtain high ethanol contents we have developed EnSieve® molecular sieve.

Designed for ethanol dehydration, EnSieve® molecular sieve offers outstanding benefits. Its unique structure provides a superior rate of adsorption and higher ethanol recovery due to the low coadsorption of ethanol. Its minimal attrition means longer service life. Product composition minimizes side reactions such as the formation of aldehydes and ketones.

The Renewable Technologies product line draws on Grace Davison’s expertise in catalysis and separations to develop and provide technologies for purification, drying and biomass conversion.

The Renewable Technologies product portfolio includes: • EnSieve® molecular sieve for ethanol dehydration • TriSyl® silica and EnPure® adsorbents for feedstock and biodiesel purification • EnRich™ catalysts for renewable fuels and chemicals

W. R. Grace & Co. - Conn.

7500 Grace Drive Columbia, MD 21044 USA +1 410.531.4000

W. R. Grace Ltd. 151 Gloucester Road Wanchai, Hong Kong +85 225.902.848

Grace GmbH & Co. KG Worms, D-67545 Germany +49 624.140.300

Grace Brasil Ltda.

Sorocaba, SP 18105-000 Brazil +55 153.235.4705

Grace®, Grace Davison®, EnSieve®, EnRich™, EnPure®, TriSyl® are trademarks, in the United States and/or other countries, of W. R. Grace & Co.-Conn. The information presented herein is derived from our testing and experience. It is offered, free of charge, for your consideration, investigation and verification. Since operating conditions vary significantly, and since they are not under our control, we disclaim any and all warranties on the results which might be obtained from the use of our products.

You should make no assumption that all safety or environmental protection measures are indicated or that other measures may not be required. © 2010 W. R. Grace & Co.-Conn.

february 2011 | Biorefining Magazine | 25

|

research

Gene Discovery Natalie Dudareva, Purdue University distinguished professor of horticulture (right), and Hiroshi Maeda, a postdoctoral associate, have discovered the final gene that drives phenylalanine production in plants. The amino acid controls many aspects of plant development, including lignin production.

PHOTO: PURDUE UNIVERSITY

26 | Biorefining Magazine | february 2011

research |

Unlocking the

Mysteries of

New research may overcome lignin’s impediments to efficiently releasing sugars from biomass by Erin Voegele

Lignin

Lignin is a necessary component of plant life. The substance, found in cell walls, is what allows plants to stand upright. Without it, most plants could not survive. While lignin is a crucial element in plant

growth, the substance also makes it extraordinarily difficult to release cellulosic sugars from biomass.

“Lignin is a formidable polymer in cell walls that contributes to the recalcitrance of cell wall biomass into the hydrolysis,” says Chang-Jun Liu, a biologist at the U.S. DOE’s Brookhaven National Laboratory. Within the cell wall, lignin essentially coats the cellulosic material, forming a physical barrier that prevents digestive enzymes from reaching the cellulose and releasing the simple sugars that can be converted into biofuels and biobased chemicals through fermentation. In biorefineries, lignin polymers have to be removed from cell wall biomass via a pretreatment process, Liu says, which tends to be expensive and environmentally unfriendly. “Therefore, lowering lignin content or changing lignin composition, thus making it more digestible in cell wall biomass, is desirable for efficient cellulosic biofuel production,” he says.

While a great deal of study has focused on developing more effective and affordable pretreatment processes to deal with lignin, research projects underway at Brookhaven and Purdue University seek a different solution. Rather than trying to design processes that more effectively dismantle lignin, the two teams are working to actually reduce the amount of lignin produced as plants grow.

Gene Identification

Researchers at Purdue have identified the last undiscovered plant gene that is responsible for the production of phenylalanine, an amino acid that contributes to many plant characteristics, including lignin production. The project is led by Natalia Dudareva,

february 2011 | Biorefining Magazine | 27

|

research

distinguished professor of horticulture, and Hiroshi Maeda, a postdoctoral associate who works in Dudareva’s lab.

The gene discovered by Dudareva and Maeda, referred to as the prephenate aminotransferase gene, is one of 10 that are responsible for phenylalanine production in plants.

Phenylalanine plays an important role in protein synthesis and the production of flower scent, antioxidants and lignin. Decreasing the production of phenylalanine could lead to reduced lignin production, which would improve the ability to process cellulosic feedstocks into fuels and chemicals.

Dudareva and Maeda’s research initially focused on Arabidopsis thaliana, a plant more commonly known as thale cress. The prephenate aminotransferase gene involved in phenylalanine biosynthesis has never before been isolated, Maeda says. “We decided first to take advantage of Arabidopsis as a model system to isolate a gene-encoded prephenate aminotransferase. This was basically the last missing gene in the phenylalanine pathway.”

The difficult thing about working with this phenylalanine pathway is that the amino acid is essential to plant life. If the pathway is completely blocked and no phenylalanine is produced, the organism will not survive. “It is hard to study genetically how this pathway works,” Maeda says. “To address this issue, we then used petunia flower, in which we have specific techniques to manipulate the pathway only in the flower, without killing the entire plant.”

Dudareva and Maeda used a coexpression analysis to find the prephenate aminotransferase gene. They monitored the expression of the other nine genes known to contribute to phenylalanine production while looking for other new genes that became active at the same time. The gene identified by the researchers had nearly identical gene expression patterns as the other nine.

E. coli bacteria were used to test their discovery. According to Maeda, they overexpressed the protein encoded by the gene and evaluated the resulting enzyme activity.

Using petunia flowers, they also decreased the gene’s expression, which reduced phenylalanine production. As a result, the studies conducted by Dudareva and Maeda have provided both biochemical and genetic evidence that the gene they identified is involved in 28 | Biorefining Magazine | february 2011

Finding the Path Liu’s research has resulted in these proposed models or pathways for lignin precursor transport. source: BROOKHAVEN NATIONAL LABORATORY

phenylalanine production. Together with the other nine genes, the research has identified a complete pathway for production of the amino acid.

Precursor Transport

Alternatively, the project being led by Liu at Brookhaven aims to understand how the building blocks of lignin are transported across cell membranes. A better understanding of how plant cell walls are constructed could lead to developing a method to change their composition in a way that allows for more efficient biofuel production. The key finding of the research so far has been that the process that allows lignin precursors to be transported across these membranes requires energy-dependent transporter molecules.

The Brookhaven researchers are trying to understand how cell wall phenolics and polyphenolics are synthesized, how their syntheses are regulated, and how those phenolics affect the structure and function of cell walls, Liu says. “We are currently exploring the key elements that control lignin precursor’s synthesis and transportation and developing novel strategies to modular lignin synthesis.”

More specifically, work completed to date has focused on understanding what molecular mechanism is used by plant cells to transport lignin precursors across cell membranes.

“In this study, we isolated the native cell

membranes, including plasma membrane and vacuolar membrane,” Liu says. The plasma membrane is essentially the membrane that surrounds the entire cell, while the vacuolar membrane separates an organelle, or subunit of a cell. The membranes were then transformed into closed vesicles that resemble bubbles. “Subsequently, we incubated those vesicles with different lignin monomeric precursors,” he continues. “Meanwhile, we applied a series of specific transporter inhibitors in the incubation. After, we examined the amount of lignin precursors that were transferred into the vesicles.”

Lignin polymers are deposited in the cell wall, while its precursors—monolignols— are synthesized in a cell’s interior cytoplasm, a jelly-like liquid that fills the cell and holds organelles. After this synthesis, Liu says these monomeric precursors must be exported across the plasma membrane and into the cell wall, where they are polymerized together.

In some types of plants, the monolignol can also link with glucose to form a molecule called monolignol glucoside in the cytoplasm.

“These glucosides are thought to be the necessary chemical forms for lignin precursor transportation,” Liu continues, noting that they are supposedly transported into the vacuole first, and then delivered to the cell wall.

It wasn’t known how those lignin monomeric precursors are transported across cell

research |

membranes. In other words, researchers had not yet determined if the process occurred via simple diffusion or some sort of active transport mechanism.

The experiment essentially addressed whether the transportation of lignin precursors requires transporters, and what type of precursor molecules could be transported through the two types of cell membranes.

“Eventually, we demonstrated that lignin precursor transport is an energy-required active process that involves a particular type of membrane transporter proteins, called ATP binding cassette transporters (ABC trans-

mised. “Taken together, our studies demonstrated that transporting lignin monomers is an energy-dependent process involving ABC transporters,” he says.

Implications, Next Steps

Now that Purdue researchers have identified the genes involved in phenylalanine production, Maeda says the next step is to focus on developing a better understanding of how those players work together to regulate production of the amino acid. “For example, in petunia flower, we found the phenylalanine level changed during the day and night,” he

Precursor Movement This chart models the ATP-dependent uptake of lignin precursors by the vacuolar and inside-out plasma membrane vesicles. source: BROOKHAVEN NATIONAL LABORATORy

porters),” Liu says.

More specifically, the research found that plasma membranes selectively take up monolignols, while vacuolar vesicles more specifically take up the monolignol glucosides. Liu and his team also determined that both transport mechanisms rely on the presence of ABC transporters. To further test this discovery, the team also added agents that deplete ABC transporters. According to Liu, this revealed that the uptake of both plasma membrane and vacuolar membrane vesicles to lignin precursors were compro-

says. “At night it goes very high, and during the day it goes down. Clearly plants are regulating this pathway in a very specific way. We want to find out how plants do this.”

According to Dudareva, the characterization and isolation of the gene, together with the characterization of the enzyme it produces, will help determine exactly what needs to be modified in order to alter the levels of phenylalanine within a plant.

A more complete understanding of the pathway could allow researchers to control the level of phenylalanine—and thereby the

amount of lignin—within a plant through genetic modification or breeding. However, Maeda also notes that it won’t be possible to eliminate lignin completely. “I think we can only reduce to certain levels,” he says. “We have to [identify] the thresholds to how much we can reduce the lignin.”

While Dudareva notes that subsequent steps in her research project will likely continue to focus on petunia flowers, she says that once they learn how to regulate the production of phenylalanine in these species, the same mechanism can be applied to other types of plants.

Basic knowledge in this area of plant science is really lacking right now, says Maeda.

Building a better knowledge base around the phenylalanine pathway should enable more rational engineering of plants, particularly in the development of bioenergy crops.

Liu and his team are also working to further their research into lignin precursors.

Now that the team knows that the transport of lignin precursors is reliant on ABC transporters, the next step is to identify the exact transporter proteins. “If we could identify those particular transporters, we might be able to genetically control their expression, therefore reducing lignin precursors deposited into cell walls, thus lowing lignin content—or selectively controlling the particular type of precursor deposition—therefore modulating lignin compositions to produce more easily cleavable biopolymers,” Liu says.

Liu also notes that manipulating lignin production without affecting plant performance is, scientifically, a very complicated issue. “In general, manipulating the early steps of lignin biosynthetic pathway more easily causes severe effects on plant growth and fitness than modulating the late biosynthetic steps,” he says. “Our studies focus on lignin precursors’ transport and polymerization, almost the end step before the polymer is formed. We expect our studies could afford a better biotechnical solution for effectively modulating lignin content while displaying less effect on plant growth and fitness.”

Author: Erin Voegele Associate Editor, Biorefining Magazine (701) 850-2551 evoegele@bbiinternational.com

february 2011 | Biorefining Magazine | 29

|

europe

30 | Biorefining Magazine | february 2011

europe |

Energizing Europe The Continent has a bioenergy goal—this is how to reach it by luke geiver The concept of an energy crop is pretty simple. Give some energy to get some bioenergy, then repeat, reaping the vast array of economical and environmental benefits along the way. But as Nils Rettenmaier at the Institute for Energy and

Environmental Research located in Germany points out, “You get nothing for free.” Rettenmaier, along with several other experts versed in European energy crop development, put that notion to the test for a consortium funded by an EU 27 Commission. The purpose: to assess the future of crops in Europe used for food, feed, fiber and fuel, all of which are part of a larger picture.

The European Union’s Renewable Energy Directive calls for greenhouse gas (GHG) emissions reductions by at least 20 percent from 1990 levels; energy efficiency improvements by 20 percent; an increased share of renewable energy to the tune of 20 percent; and an increase of biofuels usage by 10 percent—all by 2020. The work of the consortium ranged from life-cycle assessments for various potential energy crops in the Ukraine, to available land that could be utilized for energy crop production in Italy. And, although Rettenmaier says, “There is always a disadvantage connected to the advantages (for energy crops),” the idea of growing energy instead of

february 2011 | Biorefining Magazine | 31

|

europe

drilling for it is one that bears repeating, and one that Europe, as the consortium shows, has already started embracing.

The Markets

To get a sense of the rising trajectory for biomass dedicated to energy, start in 2005.

Energy crops for biofuels increased from roughly 3 million tons oil equivalence (Mtoe) in 2005 to almost 5.6 Mtoe in 2006. For 2010, the numbers equaled 16.1 Mtoe, according to Andrea Monti with the University of Bologna in Italy. Monti, who says the amount of renewable energy from biomass is expected to increase “very, very steeply” in the next few years as a credit to a change in philosophy that highlights the multiple products available from biomass, also points out that Central and Eastern European countries will show significant expansion. The expected growth, he says, can be attributed to more than just biomass for biofuels. In 2007, all the biomass that contributed to the EU’s primary energy usage was 89 Mtoe, but to meet the 20 percent renewable goal for 2020 set forth by the EU directive, that number will need to grow substantially, ending somewhere between 230 to 250 Mtoe of bioenergy. “The pace of commercializing new technologies will likely increase,” he adds.

Along with technology, he also points to other forms of bioenergy that will expand.

“The market for bioelectricity and ‘bioheat’ is still maturing,” he says. “We need to define the best process to produce bioelectricity and heat, [whether it is] gasification, pyrolysis or combustion.” Currently, the EU produces 74.5 Mtoe of solid biomass, and in 2020 that number should reach roughly 230 Mtoe; biogas in 2010 equals 9.1 Mtoe, and for 2020 it will reach approximately 48 Mtoe; biobased products such as solvents and lubricants made from biomass will grow by 5 to 30 percent and 30 percent, respectively.

Technology developments and evolving biosectors will not, however, be the only factors shaping the markets. During his research, Monti also pinpointed which regions should or already do work best for particular crops, along with another researcher who participated in the consortium, Ewa Krasuska from the Institute for Fuels and Renewable Energy in Poland. Krasuska has worked on modeling land availability for energy crops in Europe.

32 | Biorefining Magazine | february 2011

Major Energy Monti says miscanthus is a great energy crop because it produces a lot of biomass and it’s conducive to mechanical harvesting.

Monti’s work showed that for the U.K., Germany, Spain and Portugal, miscanthus will be the energy crop of choice. For willow, the U.K., Sweden and Germany will be suitable areas, and for reed canary grass, Finland and Sweden will remain the frontrunners. He also noted Italy and Spain will be best-suited for poplar.

Walter Zegada-Lizarazu, from the Agroenviornmental Science and Technology department from the University of Bologna, says the most suitable crops, in terms of agronomic management, climatic adaptability and potential biomass production for northern Europe, are fast-growing trees like poplar and willow, along with perennial grasses like miscanthus. “Under Mediterranean climates of southern Europe, eucalyptus, sweet sorghum and giant reed are promising energy crops,” he says.

For available land—land not already used for food or feed production—Krasuska’s work shows there will be 20.5 million hectares available by 2020, and 26.3 million available by 2030. These numbers happen, Krasuska says, by taking into account population prospects and crop improvements.

Perennial nonfood crops can be used for diverse climatic and agronomic conditions, he adds, and the current fallow land area is quite heterogeneous.

“Miscanthus is the best crop for bioenergy because it produces a lot of biomass and it’s very treatable by farm machines,” Monti says. “But we have to solve the cost of its propagation.”

The consortium’s efforts weren’t all about assessing land availability or which

crops would flourish in which regions, however. “If you want to introduce new crops to the agricultural system,” Rettenmaier says, “you want to know beforehand what their environmental impacts would be in order to select the most environmentally friendly and economically viable.” This is where Rettenmaier comes in.

The Future Impact

After spending five years working on lifecycle assessments for various things, Rettenmaier joined the project to perform them on selected energy crops that could conceivably be used in Europe. The crops he tested were selected by the University of Catania in Southern Italy based on climatic stratification in Europe. “Europe was divided into climatic zones,” he says. “For each zone an oil crop, a sugar crop, a woody lignocellulosic crop and an herbaceous lignocellulosic crop were selected.” The idea, he says, was to represent a huge range of different climates that exist in Europe, “and to combine those climates with the most suitable crops that could be grown in those zones.”

Not surprisingly, Rettenmaier says there was a lot of difficulty conducting the LCAs. The problem, he says, is that it really depends on the system boundaries on the exact specifications that are used for calculations. In other words, “If I’m doing an LCA, I’m putting a few assumptions in my calculations, and my neighbor might put a few assumptions in his calculations, so the results are hardly comparable.” In all, he tested 15 different crops, and as others in the consortium had also inferred, miscanthus seemed to be a front-runner. But,

europe |

he points out, don’t draw any conclusions from that. It is not sufficient to think of a new crop solely based on its GHG levels and biomass yield capabilities. “It is also important to think of the most efficient ways of using the biomass,” Rettenmaier says. Although his work pointed to miscanthus as a highyielding, highly capable GHG reducer, his work does not say “this is a winner,” he says.

“But, it indicates quite well that herbaceous lignocellulosic crops such as switchgrass or miscanthus are most beneficial in terms of energy savings and greenhouse gas savings.”

Overall, Rettenmaier’s work showed that every energy crop included in the study provided a GHG benefit, but that it doesn’t help to grow a high-yielding energy crop and then use it in a low-efficiency conversion pathway.

In that case, he points out, “it doesn’t help the environment.”

The Key to Growth

The one factor that will make all of the work by the consortium worthwhile and fruitful is a consensus, both politically and socially,

says Monti. While his colleagues understand the benefits of biomass, Monti says there are still some people who think of a biomass power plant like a nuclear power plant, and are afraid of the consequences. Rettenmaier also makes a similar argument, and one that might seem alarming considering the source.

“You cannot solve this problem on a scientific basis,” he says, regarding pushing for bioenergy via energy crop development. “You cannot find an objective decision because you always have advantages and disadvantages.”

Think of it this way, he says: if a person is concerned about biobased products, all of the products (biofuels, biogas, biopower, bioproducts) are very safe and good for GHG reductions, so that person should basically just “go for it.” But, if a person is concerned about acidification, a process that happens when crop residues are removed from soil, for example—and one of the drawbacks for several of the energy crops tested in Rettenmaier’s work showed added acidification— then a person might make a different choice.

And for Monti, strengthening the com-

munication channels between stakeholders is important, specifically between the farming and forestry sectors, and the fuel and energy sectors. He also hopes his work and that of the rest of the consortium pay off, showing the potential of energy crop development in Europe and the ramifications from an expanded and supported industry. As Rettenmaier says, “The policy makers have to choose whether they go for it or not.” From the look of things, the work of a bunch of European energy crop researchers shows that 27 EU countries have already taken a step, and have put in the initial energy. The rest is pretty simple, as far as energy crops go, and the expected returns the EU directive is calling for will produce unprecedented amounts of bioenergy. And after their work to analyze the future, there’s a pretty clear picture where to find miscanthus, willow, or reed canary grass—even if none of it comes for free.

Author: Luke Geiver Associate Editor, Biorefining Magazine (701) 738-4942 lgeiver@bbiinternational.com

LWC628-RJS-0446 Biorefining Ad #2 1/8/11 10:52 PM Page 1

IN-STOCK STAINLESS PVF From 1/8" to 36" Expansion or maintenance needs???

With over 40 years of experience selling into your market, we know and have what you need...when you need it.

No order is too small.

www.rjsales.com Buffalo, NY Cleveland, OH Chicago, IL Cranbury, NJ

800-666-0088 800-777-0820 800-777-2008 800-777-1858

Indianapolis, IN 800-777-0510 Minneapolis, MN 800-777-1355 Raleigh, NC 800-565-5525

february 2011 | Biorefining Magazine | 33

6XEVFULEH 7RGD\

%LRPDVV 3RZHU 7KHUPDO LV D PRQWKO\ WUDGH SXEOLFDWLRQ WDLORUHG IRU LQGXVWU\ SURIHVVLRQDOV HQJDJHG LQ XWLOL]LQJ ELRPDVV IRU WKH JHQHUDWLRQ RI HOHFWULFLW\ WKHUPDO HQHUJ\ RU ERWK &+3 ,Q DGGLWLRQ WR SROLF\ UHJXODWLRQ SURMHFW ILQDQFH WHFKQRORJ\ DQG SODQW PDQDJHPHQW WKH SXEOLFDWLRQ PDLQWDLQV D FRUH HGLWRULDO IRFXV RQ ELRPDVV ORJLVWLFV JHQHUDWLQJ FXOWLYDWLQJ FROOHFWLQJ WUDQVSRUW LQJ SURFHVVLQJ PDUNHWLQJ SURFXULQJ DQG XWLOL]LQJ VXVWDLQDEOH ELRPDVV IRU SRZHU DQG KHDW %LRPDVV 3RZHU 7KHUPDO·V LQWHUQD WLRQDO UHDGHUVKLS LQFOXGHV RZQHUV DQG PDQDJHUV RI ELRPDVV SRZHU &+3 DQG GLVWULFW KHDWLQJ IDFLOLWLHV SHOOHW PDQXIDFWXULQJ SODQW RZQHUV DQG PDQDJHUV SURIHVVLRQDOV ZRUNLQJ LQ FDSWLYH IHHGVWRFN LQGXVWULHV³IURP IRRG SURFHVVLQJ DQG ZDVWH PDQDJHPHQW WR DJULFXOWXUH DQG IRUHVW SURGXFWV PDQXIDFWXULQJ³DQG D JURZLQJ QXPEHU RI LQGXVWULDO PDQXIDFWXUHUV PXQLFLSDO GHFLVLRQ PDNHUV UHVHDUFKHUV DQG WHFKQRORJ\ SURYLGHUV HQJDJHG LQ ELRPDVV XWLOL]DWLRQ JOREDOO\

6XEVFULEH 7RGD\ _ VHUYLFH#EELLQWHUQDWLRQDO FRP _ ZZZ ELRPDVVPDJD]LQH FRP 5HDFK %LRPDVV 3RZHU DQG 7KHUPDO NH\ SOD\HUV WKURXJK DGYHUWLVLQJ 3ULQW DQG RQOLQH RSWLRQV DYDLODEOH &RQWDFW \RXU VDOHV UHSUHVHQWDWLYH DW

34 | Biorefining Magazine | february 2011

_ VHUYLFH#EELLQWHUQDWLRQDO FRP _ ZZZ ELRPDVVPDJD]LQH FRP

)ROORZ 8V RQ

27 TH ANNUAL

June 27 – 30, 2011

Indianapolis Convention Center Indianapolis, Indiana www.fuelethanolworkshop.com

NOW ACCEPTING

Speaker Abstracts Deadline: February 25th

The 2011 International Fuel Ethanol Workshop and Expo offers industry experts an unparalleled opportunity to showcase their industry knowledge and expertise for the largest assembled ethanol audience in the country.

Speakers at BBI International Events enjoy: • Complimentary registration for the conference • Inclusion in both print and electronic marketing campaigns • Opportunity for inclusion in a weekly ‘Panel Preview’ marketing series • Exposure a highly attended, well produced professional event Don’t miss this unique opportunity. Submit an abstract today!

2011 Sponsors

(As As of Dec. 7, 2010):

www.fuelethanolworkshop.com 866-746-8385 speakers@bbiinternational.com

february 2011 | Biorefining Magazine | 35

WORLD’S LARGEST BIOMASS EVENT

0D\ Âą $PHULFDÂśV &HQWHU 6W /RXLV 0LVVRXUL

2011 201 Exhibit Space & Sponsorships Sponso Sp so Sp so

Now Available

The 2010 International Biomass Conference was w a runaway success. Nearly 1,700 attendees, 300 exhibitors, exhibito ors, 120 speakers and 60 sponsors made for the largest and most successful biomass s conference & expo on earth. We expect exhibit space and sponsorship opportunities to go fast again this year. Don’t miss your chance to be a part of this cutting edge event. www.biomassconference.com 866-746-8385 service@bbiinternational.com 2011 Sponsors:

36 | Biorefining Magazine | february 2011