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Northaven is developing new applications for N-vinylformamide as an alternative to acrylamide

by Stephen K. Ritter
May 2, 2005 | APPEARED IN VOLUME 83, ISSUE 18

Chemists who advocate green chemistry and engineering practices like to point out that there are two parts to the green story: One green is the development of environmentally friendlier products and processes, and the other green is the color of money. Although at first it might seem that the extra effort to develop a green technology would be cost prohibitive, a growing number of small businesses are showing that creative chemistry can work around these "green fees."

Representatives from 11 companies told their stories during a symposium titled "Small Business Opportunities in Green Chemistry" held at the American Chemical Society national meeting in San Diego in March. The ACS Division of Industrial & Engineering Chemistry sponsored the symposium. The range of chemistry described at the symposium included adhesives and polymers derived from renewable feedstocks, converting turkey processing waste into oil and fertilizer, and using natural products as agricultural pesticides.

"These entrepreneurs take a green concept, convert it to a business principle, and bring to fruition new green technologies," noted Martin A. Abraham, the symposium's organizer and a chemical engineering professor at the University of Toledo, in Ohio. "They are the innovators who are developing the next generation of chemical technologies."

Although most of the companies highlighted in San Diego already have achieved success milestones, a few of them are still in the early stages of developing their green platform. One of these companies is Northaven Specialty Chemicals, Sylvania, Ohio, which was recently created to develop new applications for N-vinylformamide (NVF). This compound is being touted as a less toxic and environmentally friendlier alternative to acrylamide. Chemical engineering professor Eric J. Beckman of the University of Pittsburgh, a scientific adviser for the company, told Northaven's story.

Acrylamide is now widely known as a potential carcinogen produced when certain foods are cooked. It's also a commodity chemical used to make high-molecular-weight water-soluble polymers. The major uses for polyacrylamides are as additives for water treatment and papermaking and for petroleum production.

Like acrylamide, NVF is readily polymerizable to a high polymer, Beckman said. Another feature of NVF is that the amine group in the polymer backbone is amenable to functionalization. NVF copolymerizes well, and it can be used as a building block to make larger monomers and other compounds.

Air Products & Chemicals began exploring NVF chemistry and its potential uses in the 1980s, Beckman said. But after some time, the company concluded that demand wouldn't be sufficient for NVF to become a commodity chemical. In 2000, Air Products donated some 80 patents covering NVF to the University of Pittsburgh. This type of intellectual property donation is common for companies that don't plan to develop a technology or don't need to keep it shelved to prevent a competitor from developing it. The win-win deal gave the university valuable assets, and Air Products qualified for a tax credit.

The university, in turn, obtained funding from the state of Pennsylvania to further develop the technology and look for applications. Northaven was incorporated in January and has licensed the Pitt technology to carry it forward.

The Air Products synthesis involves reacting acetaldehyde with formamide to make hydroxyethylformamide, which is reacted with additional formamide to form ethylidene bisformamide. The bisformamide is thermally dissociated to NVF and formamide, which can be recycled.

BASF also produces NVF using a multistep reaction involving acetaldehyde, hydrogen cyanide, and formamide to make cyanoethylformamide, which is thermally dissociated to form NVF and recyclable HCN. "BASF's process is atom-economical chemistry, a cyclic process with efficient use of raw materials and energy," Beckman said. "But the problem is that the 'fail-safe' handling of HCN adds cost to the process."

THE PRICE for NVF was about $2.25 per lb in 2004, he noted, while acrylamide sells for about $1.00 per lb. "Can we use the concepts of green chemistry to make the monomer more cheaply to compete with acrylamide?" he posed. Beckman and his Pitt colleagues believe they can, and their goal is to "telescope the synthesis into a one-pot reaction that can be carried out at a lower temperature," he said.

Meanwhile, Northaven will focus on applications development. One avenue Northaven is exploring is reaction of NVF copolymers with a reducing sugar such as glucose to make gels. It's a variation on Maillard chemistry, Beckman noted. An application for the gels is to enhance the "wet strength" of a slurry of cellulose in water during papermaking. Typically, halogenated compounds are used, Beckman said, but paper producers have been moving toward chlorine-free processing during the past few years to improve their environmental performance. Pilot-scale test runs using NVF-based gels give similar results to the halogenated compounds, he said.

Another potential application is to assist in petroleum recovery from oil wells. Several products currently are used to help pump oil out of the ground, including chromium(III)-based polyacrylamide gels, Beckman noted. This type of gel typically does not hold together well in saltwater, he pointed out, but the NVF gels continue to work well even in high-salt conditions.

Beckman said that 10 years ago an academic like himself likely would have developed a sponsorship agreement with a large company to further develop the NVF chemistry. Large companies today seem to have moved away from this approach, and academics are working directly with the investment community through the creation of small companies. "I find the whole process fascinating to observe," he concluded.



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