PETROCHEMICALS
Novomer’s CO2 success
O HO Acrylic acid
The start-up sold its polyols business and will now cultivate a CO route to acrylic acid
O ALEXANDER H. TULLO, C&EN NEW YORK CITY
big payout doesn’t mean Novomer is done. Earlier this month, the Waltham, Mass.-based start-up inked an agreement to sell its Converge polyols business, which makes polyols out of propylene oxide and carbon dioxide, to Saudi Aramco for $75 million, plus another $25 million or more in potential royalties. Other start-ups might divide up the payout and pack it in. Novomer, though, intends to plow the money into another, even more ambitious, initiative: making high-volume chemicals, including acrylic acid, from carbon monoxide and ethylene oxide. Novomer traces its origins to the lab of Geoffrey W. Coates, a professor of chemistry at Cornell University. Back in 2004, Coates and a graduate student, Scott Allen, hit upon the idea of forming a start-up while the two were discussing what Allen would do when he completed his Ph.D. The two tapped the business pro Tony Eisenhut, managing director of intellectual property commercialization firm KensaGroup, whom Coates had advised in the past. Allen left Novomer for Aramco last month. Novomer went on to develop chemistry to react epoxides with CO2, which Coates’s group had demonstrated with catalysts such as β-diiminate zinc acetate and salen cobalt carboxylate complexes. An early focus for the new firm was a polypropylene carbonate polymer that can depolymerize at the relatively low temperature of 180 °C. The company had in mind applications, such as photolithography for electronic circuits, where the polymer would be needed only temporarily. Around 2010, the company switched gears to making polycarbonate polyols from propylene oxide and CO2. Conventional polyether polyols mainly use propylene oxide alone. Both are reacted with diisocyanates to make polyurethanes. Jim Mahoney, Novomer’s chief executive officer, points to a few advantages of his firm’s polyols. They have the greenhouse gas sequestration benefit of incorporating 43% by weight CO2, which also happens to be a cheap raw material. According to Mahoney, the polyols are
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Ethylene oxide
Novomer catalyst
O n Polypropiolactone
O 𝝱-Propiolactone CO
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New business Novomer aims to establish β-propiolactone as an intermediate to make important chemicals such as acrylic acid.
Novomer stronger than their conSuccinic anhydride catalyst ventional counterparts, allowing for lighter-weight polyurethane foams. In adO O dition, because the carbon HO HO in the foams is partially oxOH OH idized, they burn at a lower O 1,4-Butanediol Tetrahydrofuran temperature and give off Succinic acid less smoke in the event of fire. “It made a lot of sense to push the polyfirm will use Aramco’s $100 million to nurols first,” he says. ture a carbonylation process it is developing. Novomer isn’t alone in this approach. In it, a homogeneous catalyst reacts CO Covestro has built a plant in Dormagen, with ethylene oxide to form β-propiolacGermany, to make polyols from CO2. tone, which polymerizes into polypropioCoates notes, however, that Covestro’s lactone. At high temperatures, the polymer polyol doesn’t incorporate as much CO2 in breaks down into acrylic acid, a raw materiits backbone as Novomer’s does. al for superabsorbent polymers. Novomer is already lining up customers. A propiolactone route to acrylic acid isn’t In May, Ford Motor Co. announced that it a new idea. Celanese ran a plant in the 1960s aims to adopt the polyols in seat cushions that made the acid out of propiolactone deand other applications within five years. rived from ketene and formaldehyde. AcrylAnd of course, the polyols attracted the ic acid is typically made by oxidizing propylinterest of Saudi Aramco, which first inene into acrolein and then acrylic acid. vested in Novomer in 2013. Aramco says the Novomer has been piloting its process purchase of the business aligns with Saudi for two years. “We feel pretty confident in Arabia’s Vision 2030 program, which aims that technology,” Mahoney says. to make Aramco a pillar for modernizing the He’s so confident that he is already kingdom’s petroleum-dependent economy. planning an acrylic acid plant to open in Custom chemical maker Centauri Tech2019. It will be large—160,000 metric tons nologies of Pasadena, Texas, has been makper year—and located in Europe. Mahoney ing commercial quantities of the polyols intends to use ethylene oxide made from for about two years. Novomer already has ethanol and CO derived from natural gas or, design plans for a world-scale plant, which perhaps, gasified agricultural waste. Aramco will build in Saudi Arabia. A site Longer term, the company plans to exhasn’t been picked yet, but two of Aramco’s plore other applications for propiolactone. joint ventures—PetroRabigh, with SumitoHigh-molecular-weight polypropiolactone mo Chemical, and Sadara, with Dow Chem- has strong barrier properties and is biodeical—already make propylene oxide. gradable, a potent combination for packWilliam L. Tittle, a principal at the conaging. Propiolactone can also be converted sulting group Nexant, says the Novomer into succinic anhydride, which can be used technology is “basically sound” and sees to make butanediol and tetrahydrofuran. it as a long-term investment for Aramco. Mahoney also dreams of a U.S. propio“The prospect of this technology is not that lactone plant and, in three years, an initial it is a breakthrough technology,” he says. “It public offering. is that if a carbon tax comes into effect, this Coates, for his part, remains humble, technology would be of more interest.” even though the company he cofounded It’s rare enough that a start-up makes has real success behind it and prospects for good with a new petrochemical technology, more ahead. “I’m really excited our chemisbut Novomer thinks it can do it again. The try is being used,” he says. ◾ NOVEMBER 21, 2016 | CEN.ACS.ORG | C&EN
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