University of North Dakota Faculty/Staff Newsletter

Patented UND technology helps move the biorefinery concept closer to viability

Recently granted patents enhance UND's commitment to renewable fuels

The United State Patent and Trademark Office recently issued two patents to the University of North Dakota that increase the commercial viability of thermal cracking as a pathway to renewable fuels and chemicals. These technologies provide the capability to generate additional renewable products in biorefineries that are based on UND’s noncatalytic cracking technology.

Patent No. 8,450,541 was issued to inventors in the UND College of Engineering and MinesWayne Seames, Chester Fritz Distinguished Professor of Chemical Engineering; Darrin Muggli, a former faculty member in the Department of Chemical Engineering; and Brian Tande, chair of Chemical Engineering and director of the Jodsaas Center for Engineering Leadership and Entrepreneurship. This patent is assigned to UND and describes a method for producing cyclic organic compounds, including aromatic compounds, from crop oils. Cyclic compounds – which look like rings when you see at them at the molecular level – are a common and important class of chemicals that show up in products such as Styrofoam and other plastics, in many synthetic dyes, pharmaceutical drugs, lubricants, and thousands of other products.

Co-inventors Brian Tande and Wayne Seames holding samples of chemical products generated by UND's biorefinery process.

Co-inventors Brian Tande and Wayne Seames holding samples of chemical products generated by UND's biorefinery process.

“With this invention, we crack feedstock oil from oilseed crops, algae, microbes, waste cooking oils and other sources  in the presence of a zeolite catalyst,” said Muggli, a catalytic reaction specialist who is now the chair of the Engineering Department at Benedictine College in Atchison, Kansas. “The catalyst helps the cracked carbon fragments to form cyclic ring compounds, many of which then transform into aromatic compounds.”

"Cracking" is a common energy industry term for a process that breaks carbon-carbon bonds in long carbon chain substances. Catalytic cracking is used in the petroleum refining industry to upgrade long chain hydrocarbons that are sold as low value fuel oil into higher value, shorter chain hydrocarbons, including cyclic and aromatic hydrocarbons, which are blended into gasoline, jet fuel, and diesel fuel.

Patent No. 8,333,949, “Method for Creating High Carbon Content Products from Crop Oils,” describes a pathway from non-catalytically cracked feedstock oils, such as oil from oilseed crops, algae, microbes, waste cooking oils and other sources to high purity carbon.

When oils are cracked, a portion of the material recombines to form longer chain, complicated carbon structures, typically known as tars. The key to this UND invention is to perform the cracking reactions without a catalyst. This allows the tars that typically stick and foul catalyst surfaces to be collected. Once collected, they can be purified and processed into various carbon products, including anode grade coke, green coke, activated carbon or, most importantly, carbon fibers. By recovering the tars, at least five percent more of the inlet carbon ends up as a usable product compared to processes using a catalyst.

Nathan Bosquez, a master's degree candidate in chemical engineering, performing lab scale experiments to generate high grade carbon.

Nathan Bosquez, a master's degree candidate in chemical engineering, performing lab scale experiments to generate high grade carbon.

Carbon fibers are the most attractive product since they have the highest commercial value. However, anode grade coke also is an important product used in spark plug and other electronic devices.

“The prevailing wisdom in the research community was that you needed a catalyst to efficiently crack TG oils,” said lead inventor Seames. “We were able to prove that the actual cracking reactions, which are carbon-carbon bond cleavage reactions, occurred with the same efficiency with and without a catalyst. When a catalyst is present, it facilitates secondary reactions that can transform the cracked TG fragments into other compounds, like aromatics. However, these two steps can be separated and by making this separation, many additional chemical compounds can be produced.”

The group has a patent pending that improves upon the original aromatics patent.

“In the improved process included in the pending patent, the aromatization step, which requires a catalyst, is separated from the cracking step. This allows a user to recover a wide variety of chemical products, including the tars, which would otherwise end up as fuel products. These chemical products improve the commercial viability of a biorefinery compared to a facility that only produces fuel products,” according to co-inventor Tande.

Seames began studying crop oil cracking in 2004.

The original process generates jet fuel and diesel fuel as the primary products from either non-catalytic or catalytic cracking. Patents for this process were recently approved in Israel (no. 196123 issued 5/28/13) and Australia (no. 2007347872 issued 5/24/12). A U.S. patent (no. 8076504) to produce short chain carboxylic acids and esters via crop oil cracking was issued two years ago. When all of these processes are combined, a biorefinery can be created that can respond to the fuel, chemical, and plastics markets by producing a wide variety of fuel and chemical products.

“With these latest patents we have a significant bio-fuel/bio-chemical platform,” said Michael Moore, associate vice-president of research and UND’s principal commercialization officer. “The University is actively seeking to license this suite of technologies for rapid and widespread commercialization.”

-- Michael Moore, Associate Vice President, Division of Intellectual Property Commercialization and Economic Development, 777.6709. michael.f.moore@UND.edu, Twitter: @UND_IP_Comm


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