AVA-CO2’s move to replace formaldehyde shows the endurin’ allure in furans

March 21, 2016 |

BD-TS-032216-furans-smThere are 17,576 possible 3-letter acronyms in the Roman alphabet and sometimes it feels as it the chemical industry and the military have used them all up.

Three letter acronyms are so prevalent they have spawned their own acronym, TLA. Once, the Navy’s Director for Operational Energy, Chris Tindal, opened up a session at which military and chemists were present with a slide entitled, simply, EYA. Explain Your Acronym, he decoded, after no one could decipher it.

So, as a FYI to Digest BFFs, although as yet there’s no MOU or LOI AVA-CO2 has launched a JRP with the CTI, as an outcome of the latest CLP, to develop 5-HMF to replace CH2O because of CCP suspected by the EPA.

Let’s decode. JRP – joint research project. CTI – the Swiss Commission for Technology and Innovation; CLP, the EU’s Classification, Labelling and Packaging directive; CPP – cancer-causing potential. CH2O – formaldehyde.

And here’s the gold nugget, 5-HMF. That’s 5-Hydroxymethylfurfural, which ranks up there with “rubber baby buggy bumpers” as a tongue-twister but is far more useful. You can call it 5-HMF and it won’t mind.

Let’s rewind. Last month we reported that AVA Biochem revealed that it was expanding its product portfolio to include platform chemical FDCA (2,5-Furandicarboxylic acid)— and that’s a pathway to a molecule called PEF that’s a potential bio-based replacement for PET used to make clear plastic bottles for soft drinks. So, it’s big news in a field that’s getting crowded with promising contenders. Here are the companies, their technologies, partners and prospects.

Potential customers abound. Coca-Cola, Pepsi, Heinz, Suntory — and more to come. The Coca-Cola Plant Bottle has been a raging success, reaching up to 30% biobased content. Now, the technologies aim for The Full Monty — 100% replacement, with a variety of technologies, pathways and feedstocks.

But wait, there’s more, and that’s where formaldehyde comes in.

In June 2014 the 6th adaptation to technical and scientific progress of the CLP (Classification, Labelling and Packaging) directive was published in the Official Journal of the European Union. This classified formaldehyde as carcinogenic and mutagenic and has far-reaching and, in part, immediate consequences for a variety of business sectors but especially in the furniture industry.

Formaldehyde is a key base material for the chemical industry and serves as the source for many chemical compounds. In the EU approximately 10 million tonnes are produced per year, worldwide around 47 million tonnes. By 2017 it is expected that the global annual production will reach 52 million tonnes. A large proportion of the synthesized formaldehyde is used in the production of glues and impregnating resins for wood-based materials. Adhesive resins are also found in the manufacture of plywood panels, blockboards and chipboards (MDF and OSB) where the furniture industry is one of the main users.

In a series of studies surrounding the synthesis of phenolic resins (PF), melamine formaldehyde resins (MF) and urea resins (UF), bio-based 5-HMF is being researched as a potential substitute for formaldehyde.

Furans, the big picture

Furan derivatives produced from renewable carbohydrates are some of the most important next-generation platform chemicals. In 2004, the US Department of Energy classed FDCA as one of the 12 most important platform chemicals in the world.

What is 5-HMF, again?

It’s aa bio-based platform chemical. The oxidation of 5-HMF to FDCA (furandicarboxylic acid) is the basis for the manufacture of PEF (polyethylene furanoate) and is a contender in the Race for the BioBased Plastic Bottle, as we observed here.

PEF can also be used in the textile industry or the medical technology sector. 5-HMF has applications in the pharmaceutical industry, as an API (active pharmaceutical ingredient), and also has uses in foodstuffs and in the agrochemical sector. The research project may lead to various ways to employ 5-HMF as a substitute for the carcinogenic formaldehyde.

As a fuel, too?

Yep, 5-HMF is a precursor to DMF fuel, which has drop-in characteristics, can be cheap to make from 6C sugars, high octane (an estimated RON of 119), and 40% higher energy density than ethanol. More on that here. But there needs to be more research on the impact of DMF emissions from a lifecycle basis.

In California, researchers from the University of California, Riverside’s Bourns College of Engineering have developed what they call the Co-solvent Enhanced Lignocellulosic Fractionation (CELF) process —  consolidating multiple processing steps – such as pretreatment, sugar hydrolysis, and sugar catalysis – into one step. In a recently published paper in the journal Green Chemistry, the UC Riverside researchers showed that using CELF with highly selective acid catalysts called metal halides was particularly effective at simultaneously producing the fuel precursors furfural and 5-hydroxymethylfurfural (5-HMF) directly from raw maple wood.

AVA’s process and progress

AVA Biochem’s 5-HMF production is based on hydrothermal processing technology (HPT) and is an excellent, cost-efficient basis for the oxidation of 5-HMF to FDCA. Significant cost advantages can be realized on an industrial scale, paving the way for competitively priced bio-based packaging solutions in the future. In February 2014, the world’s first plant for commercial 5-HMF production was commissioned in Muttenz, Switzerland.

Who else’s in in the FDCA and 5-HMF race?

For one, Glucan Renewables. Glucan is producing furan derivatives from biomass.  The furfural platform will be used to launch other value-added co-products: 5-hydroxyl-methyl furfural (HMF) and downstream derivatives The company’s TriVersa Process meets the need for a renewable, environmentally friendly process to deconstruct aggregated agricultural residues created from existing 1st generation industries, into high-end chemicals and advanced materials. Glucan’s signature triumph in 2015 has been winning the Renewable Chemistry Start-Up Award, following a public vote with almost 8,000 votes cast, and after a jury of industry experts interviewed the 5 shortlisted candidates at the BIO World Congress in Montreal.

And there’s xF Technologies. xF’s technology combines known chemical reactions of biomass with novel engineering and novel homogeneous catalysis to create valuable green products from waste material.  They converts raw biomass from corn stover, wheat straw, woody waste, solid waste, algae, or pretty much any sugar containing biomass, and getting to levulinates, or specialty furans like HMF, CMF, 5-methyl-2-furoic acid or others.

ADM and DuPont are in it to win it, too. In January, DuPont and ADM announced a new breakthrough process in producing FDME from fructose, with “the potential to expand the materials landscape in the 21st century with exciting and truly novel, high-performance renewable materials”, the companies said in a joint release. FDME is a derivative of FDCA. The technology has applications in packaging, textiles, engineering plastics and many other industries. One of the first polymers under development utilizing FDME is polytrimethylene furandicarboxylate (PTF), a novel polyester also made from DuPont’s proprietary Bio-PDO™ (1,3-propanediol). PTF is a 100-percent renewable and recyclable polymer that, when used to make bottles and other beverage packages, substantially improves gas-barrier properties compared to other polyesters. This makes PTF a great choice for customers in the beverage packaging industry looking to improve the shelf life of their products.

As ADM observed in a recent patent app: “FDCA has been discussed as a biobased, renewable substitute for terephthalic acid, in the production of such multi-megaton polyester polymers as ethylene terephthalate or butylene terephthalate. FDCA esters have also recently been evaluated for replacing phthalate plasticizers for PVC.” Think polyamides, too. Specifically. Poly(meta phenylene 2,5-furancarboxylamide), which has DuPont reporting pathways to, from FDCA. That’s here.

And there’s Avantium. Avantium’s YXY technology converts plant-based sugars into Furanics building blocks. YXY enables the cost-competitive production of 100% biobased plastic materials and chemicals via chemical catalytic processes. Its main building block, 2,5-Furandicarboxylic acid FDCA, can be used as a replacement for terephthalic acid (TA), a petroleum-based monomer that is primarily used for to produce PET.

And, research conducted at Food & Biobased Research is directed at converting renewable biomass feedstocks, such as, agricultural biomass into 5-hydroxymethylfurfural (HMF). This chemical compound can be converted into FDCA by bacteria through fermentation, and is therefore an important precursor to FDCA.

The Bottom Line

Watch this space. We keep hearing more and more about furanics, 5-HMF, and FDCA all the time. Along with the search for affordable, renewable paraxylene, it might be the hottest race going on in renewable chemicals right now — filled with major players as well as raw start-ups.

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