Speciality Chemicals

Same difference

Rennovia has launched its first major chemical based on renewable feedstocks. We report from Bio-Based Chemicals East 2010

It was one of the key talking points at Bio-Based Chemicals East in Boston on 13-15 September. Rennovia, a Californian start-up specialising in the development of chemocatalytic process technologies for the production of existing large-volume bulk and speciality chemicals from renewable feedstocks at lower costs, was using the conference to launch its first commercial product.

And the product is certainly a large and well-known chemical: adipic acid. The world adipic acid market is currently estimated to be nearly 2.2 million tonnes/year, with a compound annual growth rate of 3-5% and a global operating rate of about 85%. Its average price is now about $2.75/kg, according to ICIS Chemical Pricing.

Adipic acid is used to manufacture downstream products such as polyamide (PA) 6,6 fibre and resin, adipate esters and polyurethanes. PA, especially fibres, is by far the largest consumer in the US; in Europe, the market is more balanced, though PA still accounts for about two thirds of the total there.

CEO Bob Wedinger, a 25-year industry veteran who had formerly been a director of FMC Lithium and then chief business officer at Chemtura, stresses that although adipic acid is mainly a commodity, there is rapid growth at the speciality end of the market, notably PA 6,6 resins for automotive under-the-bonnet applications.

Adipic acid is currently made in a four-step process from crude oil via cyclohexane. Rennovia's new technique takes three (Figure 1). First, biomass is converted to glucose, then this is converted to glucaric acid using selective oxidation, then glucaric acid is converted to adipic acid via selective hydrogenation.

 

Traditional (a) & Rennovia (b) routes to adipic acid

 

Introducing renewable adipic acid to the market at below the cash costs of current technologies could create multiple upstream and downstream opportunities, adds Wedinger. For instance, adiponitrile is now mostly made from butadiene, which is cheaper than adipic acid, but could revert to production from adipic acid if the price were right. This has further potential downstream implications for the making of hexamethylenediamene (HMDA), the other component in PA 6,6, and potentially also caprolactam, the precursor to PA 6.

Likewise, glucaric acid is at present only an emerging market, similar to some of the products made by companies like Cargill, Archer Daniels Midland (ADM) or Corn Products International (CPI) but it is not produced in sufficient volumes or cost-competitively enough to have an impact. Rennovia's new technology could change all this.

The chemical catalysts used in the two later stages of Rennovia's adipic acid technology were developed at the company site in Menlo Park near San Francisco, using high-throughput R&D techniques that hark back to the company's founders, Tom Boussie and Vince Murphy. They were formerly with Symyx Technologies, a well-known company in the field of high-throughput technology for the development of catalysts and other chemicals and materials.

Based on this knowledge, Rennovia has developed its own structure for high-throughput R&D into catalysts that can automatically synthesise and screen thousands of catalyst formulations every week. This expertise is used to compress the time and cost of early stage catalyst discovery and development and establish broad IP coverage around the platform technologies.

"We don't intend to be a catalysts company, however," Wedinger stresses. "We plan to be a speciality chemicals company with our own sales and marketing operations for the products we develop, but a lot of companies are interested in working with us to identify new catalysts that might be used in this or other renewable chemical processes."

The new development all happened remarkably quickly. Discovery R&D on renewable adipic acid began in December 2009, gram quantities were produced in February, continuous processes were implemented in May and pilot lab-scale production is expected to begin in December. Process integration at pilot scale will follow in 2011, then semi-works manufacturing and scale-up and initial commercial scale manufacturing, via a CMO.

Wedinger - Rennovia sees itself as a speciality chemicals company

 

The company is now seeking scale-up and commercialisation partners across the value chain. These might be, for instance, makers of adipic acid - Invista, Rhodia, BASF and Ascend are the current leaders in a relatively fragmented market - or PA producers interested in backward integration, or raw materials producers, such as Cargill, ADM or CPI, looking for forward integration.

A second product is now in the pipeline, Wedinger adds, though its identity is not being disclosed at this stage. Rennovia is currently carrying out early stage catalyst discovery and process R&D on multiple candidates and will seek to transition to process scale-up and pilot lab development in 2011, ahead of semi-works manufacturing later. Partnership opportunities for this product are now being explored.

Future products will fall into the same broad category as adipic acid, in that they will be large-volume products which are multiple steps away from the cracker and relatively complex to produce and which contain significant oxygen functionality. This will minimise the volume of conversion losses and enable production from existing carbohydrate feedstocks to be carried out cost-competitively.

"Working with refinery products, you typically start with a hydrocarbon and functionalise it," says Wedinger. "This way round, you start with an overfunctionalised molecule and 'de functionalise' it selectively to the necessary degree. We want to preserve the molecule as much as possible, so the more functionality the better."

It is important to note just how new Rennovia is. The company was founded in early 2009 and closed $12 million in Series A funding from 5AM Ventures and Versant Ventures that September. The personnel also includes ex-BP and DuPont people with varying expertise in the discovery, development and scale-up of catalysts and the development and commercialisation of chemical process technologies.

The company describes its mission as to "develop chemocatalytic process technology for the production of existing major market chemicals from renewable raw materials". The focus is on delivering a fundamental cost advantage over incumbent petroleum-based processes at crude oil prices of <$60/barrel and commercialising them in a multi-product pipeline.

Wedinger illustrates the commercial strategy by drawing a three-row, three-column grid of the companies using various means of catalysis (chemical, biological and hybrid) to create three kinds of product (fuels, existing chemicals and materials and new chemicals and materials) from renewable materials (Figure 2).

 

Figure 2 - Renewable fuels & chemicals landscape

 

There are plenty of companies active in this field but Rennovia, to the best of his knowledge is unique in using chemical catalysis for existing products. "You can change one or more of three things: the raw material, the conversion route or the product," says Wedinger. "Our way changes the raw material but keeps the chemocatalytic conversion route and an existing end product - and that has a lot to recommend it."

The attractions of using chemocatalysis for existing high-value chemicals are many, he adds. The markets are very large and include many different products. Chemocatalysis can be more readily used than fermentation in the existing assets and also beats it in terms of space-time yields, temperature and solvent flexibility, carbon efficiency and costs of product isolation.

"We can help to minimise the risk in the transition to renewables," Wedinger says. "We minimise supply chain risks by using existing renewable raw materials and producing existing large volume products, and we minimise the conversion risk by using chemocatalytic process technology and using high-throughput R&D to accelerate technology development."

Of the top 100 organic chemicals produced today, he observes, around 90 are produced chemocatalytically, with fermentation, extraction and non-catalytic means accounting for the rest. This amounts to a market of about 225 million tonnes/year worth $900 billion. Just as importantly, billions of dollars have been invested in installed capital assets to make large volume chemicals, with highly integrated use of raw materials, heat and co-product streams and the industry has a long history of employing the lowest-cost raw materials that are available, once the conversion technology had been developed.

As Wedinger pointed out in Boston, producing chemicals from renewable feedstocks is a paradigm shift in raw materials but not in conversion technology. "Adapting traditional petrochemical process technology to renewable feedstock conversion is the fastest, lowest risk and ultimately most logical path to successful commercial adoption," he claims.

 

Multi-channel high pressure reactor at Rennovia's Menlo Park site

 

The company's feedstock plan is initially to take existing carbohydrate sources of C6 sugars and later emerging lignocellulosic sources of both C5 and C6 sugars and convert them to existing bulk and speciality chemicals. Its technologies are designed specifically to be forward-compatible with lignocellulosic raw material streams; they also avoid the use of raw materials that might compete with food manufacture.

Rennovia believes that chemicals offer much more attractive potential than fuels for renewable raw materials in general because of their lower volumes, lower capital requirements and the higher value of the end products - four to eight times higher than the value of the same amount of fuel ethanol. The mass loss inherent in producing hydrocarbons from carbohydrate raw materials creates major challenges to the cost-competitive use of biomass for fuels, hence the need for cheaper raw materials.

The volumes involved on both sides also stack up in favour of chemical production, the company says. About one third of the US corn crop already goes into ethanol for fuels, but still does not meet even 4% of domestic fuel demand. By contrast, all of the current demand for adipic acid could be met from less than 1.5% of the corn crop, even if it went over entirely to Rennovia's technology, which is not expected in the foreseeable future.

Rennovia also notes that availability is opening up in the corn supply, which could thus create openings for chemical production. For instance, US demand for high fructose corn syrup (HFCS) has fallen by about 1 million tonnes since 2002. The company believes that much of the spare corn wet mill capacity could shift from HFCS to renewable chemicals without any impact on food supply.

Exactly how this market will develop is far from certain. Thus, says Wedinger, Rennovia might be interested in being part of an integrated biorefinery making both fuels and chemicals. It will also look at other emerging raw materials. For now, the focus will remain on applying its technology to existing raw materials in existing sites.

"I believe that big volumes are about two years away," he concludes, "but in the longer term the potential is massive."
 

From Online Issue: October 2010