Makin’ Money in Muddy Waters with a Magic Molecule

In Wisconsin, James Dumesic and his cohort of biomagicians revealed that they have trained up gamma valerolactone (GVL) into a solvent that converts biomass into three viable products, in one step — the platform chemical furfural, a dissolving pulp that can be spun into textile fibers and a highly pure lignin that makes battery anodes and carbon foams.

The GVL backstory

Gamma-valerolactone

We shouldn’t be surprised. GVL is the Magic Molecule. It works not only as a solvent but for practically anything. It makes an excellent fuel or a chemical of value. You can use it to strip paint, soften polymers, to enhance coconut, vanilla, toffee or caramel flavors. It’s a pro-drug that rivals GHB for intoxication effect, if not potency — which makes it a candidate as a recreational drug.

(Note to readers: don’t do drugs.)

GVL seems to do anything except possibly increase fertility when ingested on moonlit nights or run the Stark Industries arc reactor. But who knows, maybe they’ll find a pathway using GVL to make vibranium.

GVL has been attracting major attention as a solvent in the advanced bioeconomy since the Dumesic lab began publishing work on it more than five years ago now. Interest picked up considerably when GlucanBio spun out of the University of Wisconsin and aimed to reach commercial production by late 2016 — originally, focused on fuels and chemicals. One of its magical properties? It’s a solvent that you can make from biomass. And you can recover and re-use almost all of it, reducing the processing costs by leaps and bounds. Sustainable on all fronts.

But then, as we all know fossil petroleum prices collapsed in 2015. So, the search has generally been on for a product fit so obvious, tempting and commercially viable that a strategic would step forward, despite the fossil fuel price debacle, and help take a technology to scale.

So, what you see here is essentially a lot of the old Dumesic and GlucanBio technology — only ingeniously adapted to produce a portfolio of products that the pulp & paper industry could fall in love with. Lignin markets, textile fibers, furfural — it’s so tailored that Lady Gaga should be taking notes here on form-fitting.

The research team writes in Science Advances:

Herein, we propose a strategy that integrates biomass fractionation with simultaneous conversion of cellulose, hemicellulose, and lignin into products that have existing and established markets. Our biomass upgrading strategy produces (i) dissolving pulp, which is a high-purity cellulose pulp that is spun into textile fibers; (ii) furfural, which is a valuable platform chemical from hemicellulose; and (iii) carbon foams and battery anodes, which are two versatile renewable products from lignin. These initial products have been targeted by pulp mills for many years, and we have thus selected them because they can be introduced directly into current markets, thereby minimizing market risk for the first commercial plant. Once the base technology is de-risked, it can be extended to produce intermediate platform molecules, such as fermentable sugars, to manufacture renewable chemicals and fuels and to create new markets for furfural- and lignin-derived products, thereby expanding the opportunities of the biorefinery.

And here’s the biorefinery strategy, in visual form.

The path to pulp & paper: the backstory

Back in 2013, we reported that researchers at MIT developed a new technique to make cost-effective renewable gamma-valerolactone (GVL). The MIT team tipped at the time that renewable GVL can be used as a solvent, and as a renewable building block chemical for the production of bio-based materials. the t has more energy than ethanol and could be used on its own or as an additive to other fuels. GVL could also be useful as a “green” solvent or a building block for creating renewable polymers from sustainable materials.

The traditional process for converting plant material to GVL required catalysts made from precious metals and must be done at very high pressures of hydrogen gas, which made the process cost prohibitive.

The new MIT method, by contrast, uses a series of cascading reactions slightly different from the traditional pathway. Instead of converting hemicellulose directly to levulinic acid, they first convert it to furfural, a molecule that contains a five-member ring. Starting with furfural, the researchers then launch a cascade in which they open up the ring, add hydrogen atoms, then close it into a new ring — GVL.The catalyst for this series of reactions is a zeolite — a porous silicate mineral containing zirconium and aluminum, both abundant metals.

Then, we reported last March that the Dumesic lab had boosted production by 80-fold, with sugar yields topping 75 and 65 percent for xylose and glucose, respectively, and produced strong streams of ‘native’ lignin that can be used for a variety of products from construction materials to paint. (‘Native’ means the lignin is not chemically altered by the process and therefore prized by researchers normally restricted to the byproducts of paper mills.)

As Kapil Lokare and Terry Mazanec observed in The Digest not long ago:

Glucan Bio’s TriVersa Process technology uses bio-derived gamma-valerolactone (GVL) solvent to greatly accelerate the rate of deconstruction of biomass into its components.  The process simultaneously transforms the components into building blocks that can be used to launch other products such as HMF, DMF, THF, and FDCA.

The 5-HMF backstory

Let’s take a moment to assess the potential for 5-HMF.

For those with a technical bent, 5-HMF as a platform chemical contains both an aldehyde and an alcohol functional group. The oxidation of 5-HMF to FDCA (furandicarboxylic acid) forms the basis for the manufacture of polyethylene furanoate, also known at PEF.

5-HMF also has applications in the pharmaceutical industry, as an API (active pharmaceutical ingredient), and also has uses in foodstuffs and in the agrochemical sector.  In fact, in 2004, the US Department of Energy classed FDCA as one of the 12 most important platform chemicals in the world.

And, there’a drive on to employ 5-HMF as a substitute for the carcinogenic formaldehyde. Overall, 47 million tonnes of formaldehyde are produced worldwide — think “glue”s and impregnating resins for wood-based materials. Think “particle board”, “plywood panels” and “chipboard” — right away you see why the furniture industry is, ahem, eager for alternatives. But take a look around your home or office, or the room you find yourself reading in right now. Mentally subtract all the plywood, chipboard and anything that smacks of an adhesive somewhere. The entire physical world of buildings and homes as we know it rely on these materials. And while the furor over formaldehyde isn’t going to rival the problems discovered over the years in using asbestos as a building material — everyone’s eager to get to the next generation of materials, and not just eco-minded consumers.

The GlucanBio connection

As we noted in our 5-Minute Guide two years ago:

GlucanBio converts biomass to products within the biomass derived solvent gamma-valerolactone (GVL). Hydrolysis and dehydration reactions using GVL are 100X and 30X faster, respectively, than aqueous processes. This enables milder process conditions and high final product yields. Also, solvent loses can be made-up by producing GVL in the process.

The company’s TriVersa Process  produces three distinct high yielding streams valued from $500 – $7,000/MT with overall yields >75% to enable low cost production. Patent protected, this technology performs hydrolysis reactions 100X faster than conventional aqueous processes.

So, you see the connection right away. This advance from Wisconsin is a classic case of mammalian adaptation. When the market gives you lemons, make lignin pay.

What’s next for this technology?

The next GlucanBio development step is a 300 MT biomass/year pilot/R&D facility that validates the TriVersa Process with commercial engineered equipment. AT one stage, Glucan hoped to have this step achieved by mid-2017 — which has arrived, so let’s push that back in our minds. But the good news is that the pilot unit is sufficient in size and capability to inform the engineering for the first commercial plant. The first commercial plant is estimated to require an additional 24 months to construct.

Pilot plant feedstock is reported to include hardwood wood chips and empty fruit bunches. The organic liquid phase catalysis technology will simultaneously convert the biomass into three product streams. Products will include high purity cellulose, glucose, furfural, and lignin that retains much of its native chemical structure. The location of the plant is pending, although there are sites in Wisconsin, Tennessee, and Malaysia willing to host the demonstration.

The Bottom Line

It may well be that the the makers of the Molecule that Can Make Anything have found something that can make money, in the short term and in these days of low commodity prices. The economic conditions have spurred researchers to unique molecules — here are three musketeers rolled up into one very intelligent package. We await to see reaction from the pulp & paper players who will be voting with their cash.