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GFBiochemicals made a forward integration step at the start of this year through its acquisition of Segetis. The levulinic acid manufacturer wants to operate closer to the market to incorporate specific derived chemicals in existing applications, such as detergents.
Lucien Joppen

GFBiochemicals is a company of Italian origin, with a 1,200-tonne production facility in Caserta and plants at Brightlands Chemelot Campus and, since the takeover of Segetis, also in the USA (Minnesota). There is a small team in Geleen which includes R&D manager Rudy Parton. Together with several DSM colleagues, he came to GFBiochemicals in 2014.

‘The company worked on a direct route from C6 sugars to levulinic acid from 2008 to 2014. It used the Biofine process under licence for that purpose. But GFBiochemicals could not get this technology operational in Caserta. At the time we analysed the process in Caserta and made changes to the hardware and the process conditions and added new equipment. The major drawbacks were in the reactor technology and the purification of the levulinic acid.’

Direct conversion

These drawbacks have since been ‘massaged away’, according to Parton. ‘In the Caserta factory, say on TRL7 level, we now produce levulinic acid based on soft wood with yields that are similar to those of bio-ethanol. The advantage of our technology is that we are the only company in the world that can run on raw materials (C6 sugars) that contain cellulose. There are manufacturers (editor’s note: in China) that produce levulinic acid based on C5 sugars. We convert the cellulose in the biomass directly into levulinic acid. Because we are flexible with feedstock, we are also in a good position as far as availability is concerned. In due course, once we have the new plant, we also want to look at waste wood. It is a feedstock with even more attractive sustainability, but it can introduce complications to the process.’

Growth from derivatives

Levulinic acid and bio-ethanol have similar business cases, according to Parton. The point is that bio-ethanol is a product that is subsidised, while levulinic acid – as a fine chemical – has to manage in the market without external assistance.

The market for levulinic acid is currently fluctuating between 2,000 and 3,000 tonnes per year. Uses include the knitting of resins, as a means to combat microbial growth in foodstuffs and as a flavouring (butterscotch).

Parton: ‘It is a small market and completely inadequate to facilitate the further scaling up of levulinic acid. Let me put it this way: I did not move to GFBiochemicals with my colleagues from DSM to produce 5,000 tonnes a year. Our target on the horizon is a factory of around 50 Ktonnes in 2022. We want to make the interim step in 2017 with a 10-Ktonne plant for levulinic acid. Now, a capacity of 10,000 tonnes for a world market of 3,000 tonnes is indeed very large. That is why we also want to build a 10-Ktonne plant for ketals (from levulinic acid) and a similar plant for other derivatives.’

Super-concentrated detergent

It is precisely the derivatives from the ketals and levulinic acid that are interesting for GFBiochemicals to expand the market volume for levulinic acid and thus escape from a niche market, according to Parton. ‘That is also the reason for buying up Segetis. They have developed technology based on ketals from levulinic acid and, more importantly, developed applications with brand owners for existing markets. For instance, they have developed a detergent with a concentration eight times greater than the standard. This degree of concentration is possible thanks to the solvent based on ketals from levulinic acid. It is more effective than other solvents because it acts as a coupling agent. It links different constituents together better. What’s more, the solvent is biobased. Depending on the type of ketal based on levulinic acid, it can break up into perfectly harmless components such as glycerol, ethanol and levulinic acid. In environmental terms that also makes it a better solution than many fossil solvents.’

Potential in volume markets

GFBiochemicals has other derivatives in its sights, apart from the derivatives of ketals. In view of the broad scope of levulinic acid, the company cannot aim at all possibilities, according to Parton. ‘We have selected three derivatives – gamma valerolactone, methyl butanediol en methyltetrahydrofuran – that can be used as environmentally friendly solvents and/or intermediate products for nylons, among other things. Gamma valerolactone (GVL), for example, can be used as a solvent, but also as an intermediate coupling for monomers for large-scale industrial polymers. In the medium to long term, if the production volume increases, GVL has the potential to serve as a monomer for polyesters and nylons or specific acrylates. That’s when you start talking about significant markets with large volumes.’

Product mix

The route from levulinic acid to the above chemicals has been proven on a laboratory scale. The purpose of the Horizon project GreenSolRes, in which GFBiochemicals participates, is to deliver an ‘engineering blueprint’ for a 10-Ktonne plant that will produce the three chemicals and applications (solvents, resin). ‘The process will deliver the three end products in any case. This is positive, because we do not expect that we can dispose of 10 Ktonnes of a specific chemical immediately. So we are going to produce a mix of the three products, adjusting the ratio according to the market demand. Eventually there should be a plant in 2021-2023 with a capacity of approximately 10 Ktonnes per year. It will be linked to the 50-Ktonne levulinic acid plant that is planned at the same time and that will supply the raw material for these derivatives, but also for the other production locations where the other derivatives are produced, such as the ketals. Where these facilities will be built? That is one thing we still don’t know.’

Levulinic acid is a Dutch invention. In 1840 professor G.J. Mulder produced levulinic acid by heating fructose with hydrochloric acid. The name levulinic was derived from levulose, an old name for fructose. Between 1925 and 1950, Quaker Oats in particular raised the production of levulinic acid to demonstration scale. The emergence of inexpensive oil in the nineteen fifties precluded large-scale industrial production of levulinic acid based on biomass. A cheaper fossil route was developed.

DSM, among other companies, produced this product in Linz, Austria. At the end of the nineteen nineties, production dried up because the route had become too expensive and only a small-scale three-step route based on furfural was left in existence. Biobased levulinic acid came back into the picture in this century, partly due to the Department of Energy report about promising biobased chemicals (including levulinic acid) and the previously mentioned Biofine process. Since then, levulinic acid has been back with a vengeance. Multinationals like Dupont and Shell have registered various patents for several applications – Shell for biofuels, for instance – based on levulinic acid.