Iowa State engineers develop hybrid technology to create biorenewable nylon

B1M0-472Engineers at Iowa State University have found a way to combine a genetically engineered strain of yeast and an electrocatalyst to efficiently convert sugar into a new type of nylon.

Previous attempts to combine biocatalysis and chemical catalysis to produce biorenewable chemicals have resulted in low conversion rates. That’s usually because the biological processes leave residual impurities that harm the effectiveness of chemical catalysts.

The engineers’ successful hybrid conversion process is described online and as the cover paper of the Feb. 12 issue of the journal Angewandte Chemie International Edition.

“The ideal biorefinery pipelines, from biomass to the final products, are currently disrupted by a gap between biological conversion and chemical diversification. We herein report a strategy to bridge this gap with a hybrid fermentation and electrocatalytic process,” wrote lead authors Zengyi Shao and Jean-Philippe Tessonnier, Iowa State assistant professors of chemical and biological engineering who are also affiliated with the National Science Foundation Engineering Research Center for Biorenewable Chemicals (CBiRC) based at Iowa State.

The process described by the engineers “opens the door to the production of a broad range of compounds not accessible from the petrochemical industry,” Shao said.

Moving forward, the engineers will work to scale up their technology by developing a continuous conversion process, said Tessonnier, who’s a Carol and Jack Johnson Faculty Fellow and also an associate scientist with the U.S. Department of Energy’s Ames Laboratory.

The engineers’ research was supported by CBiRC, the National Science Foundation, Iowa State’s Plant Sciences Institute and the Ames Laboratory.

Here’s how their technology works:

Shao’s research group has created genetically engineered yeast – “a microbial factory,” she said – that ferments glucose into muconic acid. By applying metabolic engineering strategies, the group also significantly improved the yield of the acid. Then, without any purification, Tessonnier’s group introduced a metal catalyst – lead – into the mixture and applied a small voltage to convert the acid. The resulting reaction adds hydrogen to the mix and produces 3-hexenedioic acid.

After simple separation and polymerization, the engineers produced biobased, unsaturated nylon-6,6, which has the advantage of an extra double bond in its backbone that can be used to tailor the polymer’s properties.

The engineers say the hybrid conversion technology offers many advantages: The reaction is performed at room temperature, it uses a cheap and abundant metal instead of precious elements such as palladium or platinum, and the other compounds involved in the reaction are produced from water.

“We gave it a try and it worked immediately,” Tessonnier said. “The process does not need additional chemical supplement, and it works amazingly at ambient temperature and pressure, which is very rare for this type of process.”

Shao and Tessonnier started talking about working together while car-pooling from a research meeting two hours from campus.

Their collaboration illustrates the CBiRC way – combining the tools of biologists and chemists to develop hybrid technologies that produce novel biorenewable chemicals. And now the resulting collaboration – and CBiRC’s core vision – are turning out discoveries and high-profile research papers.

“CBiRC seeds these new ideas and concepts,” Tessonnier said. “It’s all about integration.”

Shao agreed, saying, “CBiRC provides the nurturing environment to brainstorm what can be done with the expertise owned by two groups of experts who are trained through very different routes. This vision of these fields working together is going to grow.  Students educated through such interdisciplinary research projects will definitely stand out with a broader vision in the biorenewable industry.”

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Tax Credit Would Help Iowa Biochemical Industry

Iowa could take a chunk of the nation’s $250 billion chemical market with greener replacements, but a state tax incentive is needed to help build the new industry, according to a report released Thursday.

The state’s already established renewable energy sector makes it an ideal location for companies looking to manufacture bio-based chemicals, since they use some of the same processes and feedstock, such as corn, soybeans and crop residue, the report and experts say.

Iowa will have to compete, however, with other states going after a slice of the pie.

“If you are not there at the nucleation, you can be left at the sideline and not be part of it,” Brent Shanks, one of the report’s authors, said during a news conference Thursday.

Shanks and two other Iowa State University professors wrote the report. The Iowa Biotechnology Association and the Cultivation Corridor, a regional effort to bring more bioscience companies to central Iowa, commissioned it. The report cost about $15,000.

The biotech association, Cultivation Corridor and other business groups, are pushing for a state tax incentive meant to spur the production of bio-based chemicals.

They have argued that Iowa needs to take advantage of its position before other states catch on. Many also were disappointed similar legislation did not receive enough support to pass last year.

Iowa Gov. Terry Branstad called for a revenue-neutral bio-renewable tax credit in his Condition of the State address this week.

Legislative leaders have said they are intrigued by the idea, but want to ensure the tax credit would not hurt state revenues.

“I think we want to do our due diligence to make sure what’s been proposed, No. 1, we can afford and, two, we can get some measurable results for Iowa taxpayers,” said state Sen. Joe Bolkcom, D-Iowa City and chair of the Senate Ways and Means Committee.

A tax credit to support bio-based chemical manufacturing came before lawmakers last year. The Iowa House passed it, but it failed to get through the state Senate due to concerns over the program’s price tag.

How much Iowa can snag of the $250 billion industry or a projected 50,000 new jobs nationally is not clear from the report.

“We don’t have a specific number. We do know this industry is growing at a dramatic pace, that there are a limited number of states in this country which maintain adequate supplies of feedstock and Iowa is one of them, but that we’re not the only one,” Cultivation Corridor Executive Director Brent Willett said.

Building on ethanol

Iowa has an advantage over other states to start growing a bio-based chemical production industry because of the massive ethanol, biodiesel and other bio-processing infrastructure already built here, Shanks told the Register.

The starch that comes from corn, as well as from crop residue or other biomass, is made into sugar that can be further processed into ethanol. Or the sugar can be used to make bio-based chemicals, Shanks said.

“You can take a stream of sugar that goes into ethanol manufacturing and instead convert that sugar to something else,” said Shanks, director of the Center for Biorenewable Chemicals, a National Science Foundation engineering research center at Iowa State University.

Bio-based chemicals also can be made from a biodiesel byproduct called glycerin and vegetable oil. They could go into products such as plastics, household cleaners, cosmetics and laundry detergents.

The new industry could help boost prices for corn and soybeans, commodities that have recently struggled with low prices due to oversupply, Shanks said.

He sees bio-chemical manufacturers mostly co-locate near existing dry-mill and wet mill production plants that make ethanol and other products.

Eddyville, Fort Dodge and Clinton are examples of Iowa cities where several companies have located on the same campus to take advantage of each other’s co-products.

Manufacturers are looking at bio-based chemicals to lower costs, to find greener materials and to develop better products. The report, for example, says Coke and Pepsi are in a race to make more environmentally friendly bottles.

And DuPont is making a carpet from a biorenewable chemical that performs better than some existing products, Shanks said.

Why they’re calling for a tax credit

The report indicates a tax credit could spur the industry in Iowa, using as an example how state tax incentives helped boost Iowa into an ethanol-making juggernaut.

“A similar opportunity now exists to make Iowa the leader in the development of the bio-based chemicals industry,” the report reads. “While this industry has more diverse products than the biofuels industry, the required capabilities for it are all present in Iowa.”

Between about 2006 and 2014, Iowa supported about 38 ethanol plants, providing them with about $61.7 million in tax credits, according to the report. Capital spending on the plants exceeds $4.4 billion, they employ about 1,500 people and pay annual wages of $59 million, the report reads.

The Iowa State professors also interviewed industry executives — including from Kemin Industries, Renewable Energy Group and Archer Daniels Midland — to get their thoughts on Iowa’s biofuels and biomanufacturing landscape.

The executives commonly said Iowa has multiple advantages suitable for a quickly growing bio-based chemical industry. They also said a “modest tax credit” could entice them to locate a plant in Iowa.

For example, Kemin Industries, Corn Oil One and Rewewable Energy Group all said in the report they plan to build bio-based chemical production plants and are looking at Iowa as a potential location. A tax credit, they said, could push their decision to the Hawkeye State.

This year’s legislation

Like last year, the Iowa Economic Development Authority has put a renewable chemical production tax credit proposal before lawmakers this session.

“My hope is and my request, if I had to ask, is let’s get this done quickly. … Let’s own this and let’s do it quickly,” Authority Director Debi Durham said.

The state agency would administer the tax credit. 

It is seeking to provide up to $10 million per year through the renewable chemical tax credit program, according to a study bill filed in the Iowa Senate this week.

The legislation would create a 5-cent tax credit for every pound of a bio-based chemical a company produced. Tax credits would be refundable, meaning companies with no tax liability that use the credit would receive money from the state.

To reduce the effect of the new tax credit on state revenues — a key sticking point last year — the authority is proposing to temporarily reduce how much it gives out through another program — the High Quality Jobs tax credit — by $25 million. 

State Sen. Joe Bolkcom, D-Iowa City, said he had some doubts the reduction would create the savings necessary to make the proposal revenue neutral. He also cited budget concerns with starting a new tax credit program that he said could give out $100 million over 10 years as Iowa deals with trying to give enough funding to schools.

“This may be a really good idea but so is having every third-grader being able to read at their grade level,” he said.

The High Quality Jobs reduction would be in place for five years. If enacted, the renewable chemical production tax credit would be in place for 10 years.

The authority provides tax credits through the High Quality Jobs program for companies seeking to expand or build in the state.

This story was originally published by Donnelle Eller and Matthew Patane with The Des Moines Register

CBiRC Thanksgiving and Winter Break Office Hours

CBiRC’s regular office hours are 8:00  – 11:50 a.m. and 1:00  –  5:00 p.m., Monday – Friday. With the holiday season fast approaching, CBiRC has posted revised hours for Thanksgiving Break as well as the upcoming Winter Break during the months of December and January. Please click this link for dates and further details.

November 23 & 24: 7:30-11:50 am and 12:30-4:00 pm
November 25: 7:30-11:50 am and 12:30-3:00 pm
November 26 & 27: CLOSED – Holiday

December 21 & 22: 7:30-11:50 am and 12:30-4:00 pm
December 23: 7:30-11:50 am and 12:30-3:00 pm
December 24 & 25: CLOSED – Holiday
December 28-31: OFFICE CLOSED
January 1: CLOSED – Holiday
January 4-8: 7:30-11:50 am and 12:30-4:00 pm
January 11: Resume normal hours

Glucan Biorenewables Captures Sofinnova Partners Renewable Chemistry Start-Up Award

Sofinnova Partners, the top renewable chemistry venture capital firm, has announced that Glucan Biorenewables is the winner of the prestigious Renewable Chemistry Start-Up Award.

Following a public vote with almost 8,000 votes cast, the Top-5 companies were shortlisted. These companies then presented yesterday to a jury of industry experts at the BIO World Congress in Montreal.

GlucanBio was founded in 2012, based on technology developed from the University of Wisconsin and Center for Biorenewable Chemicals (CBiRC) at Iowa State. Our primary purpose is to produce furan derivatives from biomass with cost and performance advantages. The market opportunity is strong and relevant, not only for furfural, but also for HMF, DMF, THF and FDCA. Our team offers best-in-field expertise in catalysis, IP management, engineering scale-up, and early stage commercialization.Engaging great minds like Jim Dumesic, a world-renowned catalytic chemist, and Brent Shanks, a highly acclaimed principal in the industry, gives us an advantage in hurdling technical roadblocks.


CBiRC research featured in recent issues of Green Chemistry

The November 2014 issue of Green Chemistry features a critical review on hydrothermally stable heterogeneous catalysts for conversion of biorenewables, written by Abhaya Datye, et al., that is based, at least in part, on research that is supported by CBiRC. A second critical review on selective oxidation of alcohols and aldehydes over supported metal nanoparticles, written by Bob Davis, et al., appeared in the January 2013 issue. Congratulations to Dr. Datye and Dr. Davis and their group members on these recent publications.

Green Chemistry

NSF awards maximum support to Iowa State-based Center for Biorenewable Chemicals

The National Science Foundation (NSF) has added three years and $8.48 million to the grant supporting the NSF Engineering Research Center for Biorenewable Chemicals based at Iowa State University.

That brings NSF’s total funding of the center (known as CBiRC, “See-burk”) to the maximum allowed: 10 years and $35.26 million. NSF support of the center began in September 2008 and will end in August 2018. After that, the center must be self-supporting.

Iowa State's Basil Nikolau and Brent Shanks

Basil Nikolau, the center’s deputy director and Iowa State’s Frances M. Craig Professor of Biochemistry, Biophysics and Molecular Biology, said the center was built on a vision of biologists and biochemists working with engineers to solve common problems. The joint efforts have opened up new catalysts and technologies for the production of biorenewable chemicals.

That has helped CBiRC quickly establish a legacy of innovation in research, technology-led entrepreneurship and education, said Brent Shanks, the center’s director and an Iowa State Anson Marston Distinguished Professor in Engineering.


Wurtele receives Iowa’s Women of Innovation Award

CBiRC faculty affiliate, Eve Syrkin Wurtele, was awarded the Woman of Innovation award for Research Innovation and Leadership by the Technology Association of Iowa (TAI) at their fifth annual DuPont Pioneer Iowa Women of Innovation event held on November 15, 2012 in Des Moines. This is the second consecutive year Dr. Wurtele was a finalist for this award.

Nominations were submitted for women from communities across the state. Finalists represent a range of backgrounds: teachers, researchers, technologists, vice-presidents, presidents, CIOs, and CEOs, among other titles. They include scholarship winners and providers. Many nominees are nationally and internationally recognized through various publications, panels, and media outlets. They all represent excellence in innovation and leadership. Finalists also include high school, undergraduate and graduate students who have demonstrated extraordinary and unique achievements in technology.

The TAI is the premier professional organization accelerating the success of Iowa’s technology industry and tech-based economy. Read the full story.

CBiRC research featured in recent issue of Chemical & Engineering News

Suitable catalysts for converting biomass to chemicals and fuels at low cost are not generally available today. A lot of petrochemical refining catalysts could do the job—but biomass refining conditions destroy them. Researchers have now found a way around this problem, by enhancing the stability and durability of the supports on which catalytic metals are dispersed.

Read the December 3 Chemical & Engineering News article for more.

NSF adds three years with $12 million in funding

The National Science Foundation (NSF) has added $12 million and another three years of support to the NSF Engineering Research Center for Biorenewable Chemicals based at Iowa State University. The continuing support brings federal investment in the center up to $30.5 million over eight years. The center’s vision is to transform the industrial chemical industry from one based on petroleum to one based on biorenewable resources.

Engineers and scientists are working together in new ways to invent catalysts that lead to industrial chemicals from biorenewable resources. Industrial partnerships are expanding. Startup companies are launching. Education partnerships are reaching teachers and students. And an international reputation is growing.

They’re all steps the National Science Foundation (NSF) Engineering Research Center for Biorenewable Chemicals based at Iowa State University has made over its initial four years. That progress has led to the NSF augmenting the center (known as CBiRC, “See-burk”) with three additional years and $12 million.

That brings the total federal investment in the center through the NSF’s Engineering Research Center program up to $30.5 million over eight years. The center can still be renewed for an additional two years, potentially bringing the NSF’s total support to 10 years and $34.9 million. After 10 years, CBiRC will transition to a self-supporting research center. In addition to the center’s base funding, it has so far garnered more than $14 million in other support.

“In four years we’ve certainly come together as a center and we have a shared vision across all the researchers,” said Brent Shanks, the center’s director and the Mike and Jean Steffenson Professor of Chemical and Biological Engineering at Iowa State. “We are accomplishing what the NSF wanted – interdisciplinary research.”

The center’s vision is to transform the industrial chemical industry – a $400 billion-a-year business in the United States – from one based on petroleum to one based on biorenewable resources. To do that, the center has asked researchers who study chemical or biological catalysts to start working together to develop new and sustainable technologies that produce the industrial chemicals used in everything from building materials to personal-care products.

Basil Nikolau, the center’s deputy director and the Frances M. Craig Professor of Biochemistry, Biophysics and Molecular Biology at Iowa State, said the center’s interdisciplinary approach is attracting the attention of industry.

“We are making progress and a measure of that is the companies that have joined us,” Nikolau said. “We’re setting a new paradigm for this research. We’re doing basic research that companies are buying into.”

When the center was established, it had six industrial partners. The center now has 27 (including Ashland, Chevron Phillips Chemical Co., DuPont, Grain Processing Corp., Michelin Americas Research Co., and POET) and is discussing additional partnerships. The center is also spinning off four companies in Iowa and three from partner institutions. The Iowa startups include Glucan Biorenewables LLC, originally established by Shanks; Peter Keeling, the center’s industrial collaboration and innovation consultant; and James Dumesic, the Steenbock Professor and Michel Boudart Professor of Chemical and Biological Engineering at the University of Wisconsin-Madison.

The center has also attracted attention from funding agencies and the science media:

  • Earlier this year, Nikolau, Keeling and Shivani Garg – a graduate student in biochemistry, biophysics and molecular biology – won an Innovation Corps grant from the NSF. The grant will support their work to develop bio-based chemical feedstocks.
  • And, the CBiRC way – combining chemical and biological technologies to produce biorenewable chemicals – was recently featured in Chemical & Engineering News. The story by Mitch Jacoby notes that “coupling chemical and biological processing offers advantages over either one on its own.”

In addition to those developments, the leaders of the center’s three research thrusts said they’re seeing many signs of technical progress:

Thrust one, new biocatalysts for pathway engineering

Joseph Noel – professor and director of the Jack H. Skirball Center for Chemical Biology and Proteomics at the Salk Institute for Biological Studies in La Jolla, Calif., and an investigator with the Howard Hughes Medical Institute based in Chevy Chase, Md. – said the program has identified pyrones as molecules for the center’s testbed research across disciplines. He said researchers have developed protein engineering techniques to improve the production of biorenewable molecules from sugar by common baker’s yeast. Chemical catalysts then convert the molecules to commodity chemicals. Noel said the research program has also successfully integrated high school and undergraduate students in its laboratories.

Thrust two, microbial metabolic engineering

Jackie Shanks, the Manley Hoppe Professor of Chemical and Biological Engineering at Iowa State, said researchers have used E. coli to produce carboxylic acids at the highest level reported to date. Carboxylic acids can be used to produce many industrial chemicals. She said researchers have also improved E. coli’s ability to resist the toxicity of the acids.

Thrust three, chemical catalyst design

Robert Davis, the Earnest Jackson Oglesby Professor of Chemical Engineering at the University of Virginia in Charlottesville, said researchers have made significant progress converting pyrones from research thrusts one and two to high-value chemicals. He said researchers have also developed technologies that convert carboxylic acids to alpha olefins that are used to make detergents and other chemicals.

Brent Shanks said the center has established several education initiatives, including a graduate minor in biorenewable chemicals at Iowa State, research internships at the center’s European partners, a summer research program for undergraduates, research experiences and workshops for school teachers and a program that places graduate students in middle school science classrooms.

All in all, Shanks said the center’s work is getting noticed and its researchers are taking calls from industry, technical conferences and the biorenewable research community.

“It is our driving goal,” he said, “to be considered the place in the world to do biorenewable chemicals.”