Partners in Production

FROM THE MAY ISSUE: Chemical companies are developing technologies that would create new market opportunities for the ethanol industry.
By Tim Albrecht | April 19, 2018

The ethanol industry has polished its coproduction of distillers grains. Now, a handful of companies have found different uses for DDGS, or ethanol itself, that can provide new value-added coproducts for the industry.

Ethanol is flexible and can be used to make chemicals for products ranging from solvents to consumer goods—such as plastics and personal care items. Greenyug LLC, a technology development company based in Santa Barbara, California, recognized favorable economics for the ethanol industry, and ample opportunity, says Luca Zullo, vice president of business development at Greenyug.

“Ethanol is also a good molecule to do a lot of chemistry because it’s a reactive molecule,” he says. “Many ethanol plants are in locations with availability of space and services, while providing a feedstock for us. There were lots of opportunities to do chemistry that’s valuable and can bring you to higher-value products.”

Innovative Technology
Through process intensification and liquid phase catalysis, Greenyug’s platform uses nondenatured ethanol to produce ethyl acetate and hydrogen. The ethyl acetate can be used in products such as paints, coatings, pharmaceuticals and a variety of other consumer goods. The system offers a smaller physical footprint than comparable systems found at petrochemical refineries.

Greenyug is working on constructing its first full-scale production facility adjacent to the Archer Daniels Midland Co. ethanol plant in Columbus, Nebraska. ADM will provide Greenyug’s facility with feedstock and other services, while Greenyug’s bolt-on system will provide the hydrogen byproduct as an energy source for the plant, Zullo says.

Similarly, xF Technologies Inc., a chemical company based in Albuquerque, New Mexico, has developed a process to convert DDGS into furoate, or 408, esters. XF initially plans to use the 408s in cleaning and processing solvents, plasticizers, paints, coatings and personal care products, as well as an oxygenate in the ethanol industry.

It is a two-step, thermochemical process that first generates an intermediate called chloromethylfurfural (CMF), followed by a catalytic step to convert the CMF into a finished product, says Aviad Cahana, CEO of xF Technologies.

XF’s business model is to license its technology to an ethanol producer, while collecting a royalty. This would provide the producer with as much ethyl furoate as it needs, Cahana says, adding it would provide the ethanol industry with a wide range of new coproduct possibilities.

“It would give them opportunities to explore blending ethanol with ethyl furoate in new chemical applications, which brings the ethanol producer into the chemical world that has a higher profit margin,” Cahana says. “Our molecule opens a new market for them.”

Gevo Inc. has taken a different route than Greenyug and xF, focusing on fuels. Gevo, a renewable chemicals and advanced biofuels company, produces both ethanol and isobutanol—used in production of jet fuel—at its Luverne, Minnesota, facility. Gevo purchased the ethanol plant from Agri-Energy LLC in 2010 and retrofitted it for its own purposes. Agri-Energy still operates the plant. While ethanol is the main moneymaker, with a capacity of 20 MMgy, Gevo is focusing on increasing isobutanol production from its current 1.5 MMgy.

Pat Gruber, CEO of Gevo, says producing both ethanol and isobutanol fits the company’s goal of decarbonizing chemicals and fuels. “The most practical ways (to decarbonize fuels) are to use a fermentation technology like ethanol or isobutanol to convert fairly complicated feedstocks—such as corn—into simple alcohols that could either be sold directly or used as intermediates for chemical processes to transform them into other products—such as jet fuel, gasoline or into plastics.”

Rich in Opportunities
All three companies say their technologies hold more opportunity for the ethanol industry, beyond the obvious chemicals markets.

Zullo says Greenyug is focusing on its ethyl acetate, but isn’t ruling out the possibility of venturing into other chemicals, such as n-butanol and higher alcohols. “Of course, ethanol chemistry is rich in opportunities—such as ketones, acetates, esters, etc., and we do expect our research and development program and business development program will accelerate in the near future, as revenues will allow us to reinvest in the business growth.”

Ethyl furoate also has a new market possibility, as an additive in both gas and diesel, Cahana says. “It sits at the higher end of gasoline and the lower end of diesel in terms of boiling point. So, it can go into both and the same molecule has benefits for both forms of fuel. That’s another way to put ethanol into a new market in the future.”

Gevo is working on multiple technologies for new coproducts from either ethanol or isobutanol. It has a technology that converts ethanol into products such as propylene, which is a plastic used in fibers and packaging materials, Gruber says. “We have a technology that looks like it works. It’s still in the development phase, but it works.

“That technology can also be used to generate things like diesel fuel and chemical products. We see there is a lot of value adding that can be done downstream, but we need to think in an integrated sense for it to work economically.”

On the isobutanol side, Gevo has proven how to convert isobutanol into butylene, Gruber says. “From butylene, we make jet fuel and isooctane, both of which are extremely clean—low particulates, low sulfur and low carbon. That’s what we’re working on commercializing.”

Gevo also plans to improve corn-oil extraction, Gruber says. “We’ve seen people capturing oil out of a plant and we do it too. But, we have visions of making food-grade vegetable oil. It lowers the overall cost of alcohol production and makes the plant more profitable.

“There are lots of optimizations and opportunities for ethanol down the line,” Gruber says.

Author: Tim Albrecht
Associate Editor, Ethanol Producer Magazine
[email protected]