Issue Date: December 14, 2009
Big Plans For Succinic Acid
Earlier this month in rural northeastern France, a venture between a U.S. company and a French farming cooperative started manufacturing succinic acid from agricultural rather than petrochemical feedstocks. Built at a cost of $27 million, the demonstration facility is the first of its kind in the world—but almost certainly not the last.
Four other succinic acid projects are in development across Europe, the U.S., and Asia. Their backers are betting on the success of succinic acid as a new, versatile, and environmentally friendly starting point for a wide range of so-called biobased chemicals. Other materials, however, have tried and failed to claim this crown, and the odds are poor that all the projects will survive.
Scientists have been fermenting sugars or otherwise upgrading agricultural products for centuries. Many of those early chemicals were eclipsed by synthetic alternatives during the rise of petroleum-based chemistry. Still, a number of agriculturally derived chemicals—xanthan gum, pine rosin resins, and citric acid, for example—persist today.
Now, industry's desire to trim its carbon dioxide emissions is providing renewed impetus for biobased chemicals, and researchers are taking up the tools of biotechnology to create brand-new materials. A facility making one such product, a plastic known as polyhydroxyalkanoate, was just completed in Clinton, Iowa. DuPont is fermenting sugars into 1,3-propanediol in Loudon, Tenn.
Yet examples of large, successful biobased chemical projects are few and far between, points out Mark Morgan, who follows industrial biotechnology for the consulting firm Nexant. He notes that DuPont has yet to follow through on its plan to expand propanediol beyond the Tennessee plant. "Was it the technology or the price? I don't know," he says, "but something didn't work right from a commercial perspective."
Polylactic acid, a polymer made from fermentation-derived lactic acid, has experienced growing pains of its own, Morgan notes. NatureWorks, a joint venture between Cargill and Dow Chemical, opened a huge polylactic acid plant in Blair, Neb., in 2002. Three years later, however, Dow left the venture, saying it doubted the polymer's ability to compete with conventional plastics. Teijin, a Japanese company, later took Dow's place, but it, too, eventually sold out.
Executives in the nascent succinic acid industry insist their product will be different. Fermenting it from sugar actually consumes CO2, they say, a valuable trait in a carbon-constrained world. Succinic acid made synthetically already has a number of applications. If made cheaply enough, the renewable version could capture additional markets plus serve as a platform for chemical derivatives with applications throughout the industrial world.
In support of their enthusiasm, proponents point to a 2004 Department of Energy report that screened some 300 biobased products for their potential as chemical building blocks. Succinic acid was one of the top 12 finalists. A 2008 Department of Agriculture report went further, calling succinic acid one of only three of these building blocks with near-term potential.
Cenan Ozmeral, general manager of succinic acid developer Myriant Technologies, points to an even more recent sign of succinic acid's potential: The September announcement by BASF, the world's largest chemical company, that it will enter the business. "In my opinion, BASF's entrance legitimizes the market," Ozmeral says.
At the moment, world consumption of synthetic succinic acid is modest—between 60 million and 80 million lb per year, by Morgan's reckoning. Most production is in China, where succinic acid, a four-carbon dicarboxylic acid, is made from maleic anhydride. Applications include quinacridone pigments, pharmaceutical intermediates, and metal plating. "It is an important but niche product," Morgan says.
In contrast, Jean-François Huc sees billion-pound potential for biobased succinic acid. Huc is president of DNP Green Technology, which is one-half of Bioamber, the joint venture that built the plant in northeast France. The other half is Agro Industrie Recherches & Développements (ARD), an R&D center run by a consortium of French agribusiness concerns.
Bioamber's plant, in the town of Pomacle, has a 350,000-L fermentation reactor and an initial succinic acid capacity of 5 million lb per year. Although the facility is just now opening, Huc says it has committed customers, both for the chemical itself and for a patented runway deicing fluid made from succinic acid. "We're confident we can sell the entire capacity," he says.
And the French plant is just the start. DNP Green's plan is to license Bioamber technology to third parties that will build large-scale facilities in which DNP Green will take an ownership stake. Huc says his firm is negotiating with a top North American starch company and a leading Asian trading firm about plants with capacity of roughly 60 million lb each. Two such trading firms, Mitsui & Co. and Samsung, recently invested in DNP Green.
Although Bioamber appears to be the first to market with appreciable quantities of biobased succinic acid, others are close.
DSM and Roquette formed a succinic acid joint venture in early 2008 and have been providing samples to customers for more than a year from a pilot plant at Roquette's starch refining complex in Lestrem, France. Later this month, they will start a demonstration plant at the site with succinic acid capacity of 300 to 500 metric tons per year, according to James Iademarco, DSM's vice president for biobased chemicals and fuels. He hopes to have a facility producing thousands of tons up and running as early as 2011.
In 2008, Roquette licensed technology for making succinic acid in Escherichia coli from both the University of Georgia and Rice University. When validation of the demonstration plant starts early in 2010, production could be based on these microbes, Iademarco says, but the firms have also been working with other bacteria.
BASF is entering the business in cooperation with CSM, a Dutch bakery ingredients company that owns Purac, the world's largest producer of lactic acid via fermentation. The partners are harnessing bacteria, isolated by BASF from the stomach of a Holstein cow, that convert glucose or glycerin to succinic acid.
Maren Bauer, a project manager with BASF Future Business, says the partners will start making succinic acid in commercial quantities—she won't be more specific about the size—at a Purac plant in the second quarter of 2010.
Perhaps the most ambitious succinic acid contender is Myriant, a Massachusetts-based company that was created in June when the biofuels developer BioEnergy International spun off its specialty chemical assets as a separate company. Although it's a start-up with a need for funding, the firm boasts veterans from DuPont and BASF on its staff and luminaries such as ex-Central Intelligence Agency head R. James Woolsey on its advisory board.
Ozmeral, who joined BioEnergy a year ago after a long career with BASF, explains that Myriant is building on specialty chemical technology developed by Lonnie Ingram, a microbiologist at the University of Florida who was awarded U.S. patent number 5,000,000 in 1991 for a strain of E. coli that was genetically modified to convert both five- and six-carbon sugars to ethanol.
An early success was licensing a version of the organism to Purac for production of d-lactic acid, which can be combined with naturally occurring l-lactic acid to make polylactic acid with high thermal stability.
Succinic acid is Myriant's next project. Ozmeral says the company has already made it in 5,000-L reactors at Wisconsin Bioproducts, a contract fermentation company in Milwaukee. It is now scaling up to 20,000- or 50,000-L reactors at Fermic, a Mexican firm that operates one of Latin America's largest fermentation facilities.
The next step will be to retrofit an existing small ethanol plant to make succinic acid. Ozmeral says he is in negotiations with two ethanol companies and expects to be producing at the rate of 30 million lb per year by the third quarter of 2010. The culmination of these efforts will be a 140 million-lb succinic acid plant. Myriant just won a $50 million DOE grant to help build such a plant in Lake Providence, La.
Succinic acid proponents justify their high-volume plans on the chemical's synthetic versatility, which they say exceeds that of biobased monomers such as lactic acid and propanediol. At BASF, Bauer says succinic acid is of interest as a raw material for biodegradable polyester polymers. A number of companies already make polybutylene succinate using synthetic succinic acid. Substituting the new succinic acid would yield a polymer that is both biodegradable and, to an extent, biobased.
DNP Green's Huc has high hopes for potassium succinate-containing road and runway deicers, a market where his firm claims significant intellectual property. Last year DNP Green and ARD formed a partnership with Basic Solutions, a British provider of environmentally friendly products that already sells deicers to much of England's rail network.
Huc also sees succinic acid and its derivatives being used in plasticizers and as a solvent. And it can partially replace six-carbon adipic acid as a raw material in polyurethanes and polyester polyols. Interest is high, Huc claims. "We have sampled about 70 companies so far in the chemical industry," he says.
Myriant's outsized ambitions, meanwhile, extend to its intended use for succinic acid. Ozmeral contends that the only market that justifies 100 million-lb-plus plants is butanediol, a high-volume chemical used to make everything from polybutylene succinate to spandex to polyurethanes. BASF is the world's largest producer of butanediol, which commands a global market of about 3 billion lb per year.
Modern butanediol technology, supplied by Davy Process Technology and other engineering firms, oxidizes butane in a ring-forming step to form maleic anhydride. Butanediol is obtained via esterification and hydrogenation. Dimethyl succinate is an unisolated intermediate between maleic anhydride and butanediol.
Ozmeral proposes to current butanediol producers that they bypass the expensive butane oxidation step and buy succinic acid from Myriant instead. Although Bauer won't elaborate on BASF's plans for the butanediol market, Ozmeral figures that butanediol must be the big firm's ultimate goal. "That's why BASF is in it, and that's why we are in it," he says.
Obtaining butanediol from succinic acid would permit 100% biobased polybutylene succinate, which would likely command a premium price. But competitively selling biobased butanediol into most other markets, Ozmeral says, would require pricing succinic acid at about 50 cents per lb—a target he says Myriant can reach. Synthetic succinic acid sells for about $1.40 per lb today.
Others aren't aiming quite so low. Huc says Bioamber is aiming for around $1.00 per lb. DSM's Iademarco, meanwhile, divides the future into the near and the far. Although he expects the price of biobased succinic acid to eventually fall below the synthetic, he thinks early adopters will be willing to pay a small premium for initial, limited supplies based on its favorable ecological footprint and renewable status.
Indeed, Morgan, the consultant, doesn't see the logic in approaching customers right off the bat with ultralow prices. "The last thing you want to do with a new process is come in and collapse the market," he says.
With price and demand still unknown, even the most optimistic succinic acid boosters acknowledge that not every venture is likely to succeed. And although executives won't talk trash in print, off the record they are all too happy to handicap their competitors' ability to succeed in the long run.
For example, most question the staying power of Japan's Mitsubishi Chemical, which revealed in September that it is weighing a project with PTT, a big refining and petrochemical firm controlled by the Thai government, to make biobased succinic acid and polybutylene succinate in Thailand. Mitsubishi already sells the synthetic polymer under the name GS Pla.
Competitors point out that the pair announced only that they are studying the feasibility of forming a joint venture. Moreover, they question the success of a 2003 alliance between Mitsubishi and fellow Japanese firm Ajinomoto to develop biobased succinic acid. Mitsubishi responds that the alliance in fact succeeded in its goal of advancing basic research on succinic acid. The firm says it now owns a proprietary organism that boasts high efficiency and safety.
The venture between BASF and Purac is considered more promising. Purac already has lactic acid, while BASF makes vitamins, drug ingredients, and other fine chemicals via fermentation. Arno van de Ven, Purac's vice president of chemicals and pharmaceuticals, adds that existing infrastructure—notably excess fermentation capacity at Purac's plant in Barcelona—is another advantage.
DSM and Roquette also boast industrial biotech experience. DSM has engineered various microbes to make large volumes of products such as citric acid, vitamin B-2, and the antibiotic intermediate 7-ADCA. Roquette is one of Europe's largest starch refiners and has commercialized polyols, gluconic acid, and other chemicals from agricultural raw materials. In addition, Iademarco emphasizes the partners' size and financial strength. "Raising capital for large facilities won't be trivial," he observes.
Although Myriant is much smaller, Ozmeral insists that it will also be a survivor. It successfully made succinic acid in its own labs and in Wisconsin, he notes, and recently formed an alliance with the German engineering firm Uhde to advance large-scale engineering. He says Uhde replicated the fermentation and isolation of succinic acid at its facility in Leipzig, Germany. Now, the partners are seeking to duplicate these results at the Mexican facility.
Likewise, Huc says DNP Green will succeed along with the big-name players. He notes that Bioamber has spent years perfecting E. coli-based succinic acid fermentation technology first developed in 1995 by DOE and a predecessor to DNP, Applied CarboChemicals.
Huc enumerates three barriers to success in succinic acid—barriers he says Bioamber has crossed. One is getting clearance from regulatory authorities. "The more highly engineered the organism, the harder it is to get approved," he says. The second is achieving cost-effective yields, and the third is isolating and purifying the acid from a fermentation broth that functions best near neutral pH.
Once these goals are achieved in a pilot plant, they must be replicated in a commercial facility, where waste streams, recycling, and heat transfer are real issues. Huc likens industrial biotech scale-up to advancing drugs through the development pipeline. "Animal testing is one thing; human testing is another," he says.
Not surprisingly, all involved maintain that their succinic acid ventures will succeed. Yet most agree that five projects are more than this nascent market can support. "The playing field for succinic acid is potentially big enough for three companies," Purac's van de Ven says. "But four or five companies? I cannot make that judgment. We will see."
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