Biobased Platform Chemicals: Levulinic Acid
It's been a long time coming, but this could be the decade of levulinic acid
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Levulinic Acid
Levulinic acid is having a moment right now with GF Biochemicals and NxtLevvel (JV with GF Biochemicals) attempting commercialization of levulinic acid derivatives. If you have no idea what levulinic acid is then you can perhaps go here for a brief explanation, but the reason why it’s so interesting is because it can be made from non-food biomass and it has enough functionality to be interesting for industrial and polymer chemists. My own doctoral thesis in biobased epoxy resins was based on a levulinic acid derivative—Diphenolic Acid.
When it comes to changing the origins of our economy there are really two options in moving away from oil dependence. The first option is to develop easy to use drop-in replacements to existing petrochemicals and this is something that Origin Materials is working on now with their chloroymethyl furfural (CMF) to terephthalic acid platform. The second option is to develop a whole new class and category of biobased chemicals and materials that can be substituted for existing petrochemicals.
It’s not like our existing petrochemicals are that great anyway. We are mostly stuck in a trap of performance versus cost and getting out of this trap requires competitive chemicals that perform similar or better than their current petrochemical counterparts at similar or lower prices. Levulinic acid has long been viewed as a viable molecule on which to build companies and its derivatives such as butyl levulinate (ester of levulinic acid and 1-butanol), a potential plasticizer.
The earliest production of levulinic acid that I remember during graduate school was a little company called Biofine Technologies LLC, which was co-founded by Steve Fitzpatrick, a chemical engineer. Biofine’s process is a dilute acid hydrolysis of mostly cellulose to produce levulinic acid. Fitzpatrick won the Presidential Green Chemistry Award in 1999 for his work. From the award:
Biofine developed a process to convert the waste cellulose in paper mill sludge, municipal solid waste, unrecyclable waste paper, waste wood, and agricultural residues into levulinic acid (LA). LA can be used as a building block for many other useful chemicals. LA made from waste cellulose reduces the use of fossil fuels and reduces the overall cost of LA from $4–6 per pound to as little as $0.32 per pound.
Biofine’s original demonstration plant is located at the University of Maine Orono in Old Town. I got a chance to meet Fitzpatrick and his co-founder when I was in graduate school (around 2015) and Biofine also built a demonstration plant in Caserta, Italy that as far as I was told never got finished due to a lack of funds.
It turns out that the demonstration plant in Caserta, Italy would eventually become GF Biochemicals, which is now led by Mathieu Flamini, a French football star who played for some of the best teams in the world including Arsenal and Milan as a midfielder, and he is also a major investor. I think Flamini’s passion for biobased chemicals, specifically levulinic acid, is exactly what the industry needs.
Mathieu, if you are reading this I’d love to chat about your company.
Also, Origin Materials also has a pathway to levulinic acid.
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Levulinic Acid Positioning Today
Back in 2016 GF Biochemicals would acquire Segetis, which included 250 patents which spanned across end markets such as fragrances, plasticizers, cleaners, personal care products, and more. Karen Laird reported on the story for Plastics Today back in 2016 about GF Biochemicals and the issue around price:
Hence, when GFBiochemicals not only developed a one-step process to bring levulinic acid to market, but also implemented its proprietary technology at its commercial-scale plant in Caserta, Italy, in partnership with the University of Pisa and the Polytechnic University of Milan—retrofitting the plant with new conversion, recovery and purification technology—the world sat up and took notice.
I suspect GF Biochemicals is using the same Biofine process since their plant is also in Caserta, Italy and the add-on of being able to recover spent chemicals to restart the process is likely the reason the costs have gone down significantly. It’s not clear if Biofine Technologies is still operational, but I’ve reached out to Steve Fitzpatrick to get more details.
Here in the US, it appears as if a joint venture between GF Biochemicals and Towell Engineering Group has taken the name NxtLevvel in an effort to bring levulinic esters and ketals to the US market based on the GF Biochemicals and Segetis platform. If you are a chemist or formulator working in coatings and you want a biobased replacement for Texanol, then consider reaching out to Steve Block at NxtLevvel.
Some of the places that Levulinic acid and its derivatives could gain traction via BioRefineries Blog:
Fuel additives. Levulinate esters are additives for gasoline and diesel transportation fuels. For instance, they can replace current cetane improvers and cold-flow performers for diesel. They may also replace lubricity improvers. Methyltetrahydrofuran (MeTHF), a levulinic acid derivative, can also be blended up to 50% with gasoline to increase vehicle performance and reduce air emissions.
Solvents. Levulinic acid esters, gammavalerolactone (GVL) and MeTHF are suitable solvents for a number of applications. GVL can replace ethyl acetate and MeTHF can be used as a substitute of tetrahydrofuran (THF) in the fine chemical and pharmaceutical industry.
Polymers and plasticizers. Levulinic acid-derived ketal esters can replace major phthalate-based plasticizers. Methyl butanediol (MeBDO) has potential as a monomer for polyurethanes. GVL can be a monomer for polyester-polymers and starting materials for pyrrolidinone-isomers.
Resins and coatings. Levulinic acid can be used in polyester resins and polyester polyols to increase scratch resistance for interior and exterior coatings. Its derivative Diphenolic Acid (DPA) is used in protective and decorative finishes.
Agro-chemicals. Its derivative delta-amino levulinic acid (DALA) is used as an herbicide on lawns and certain grain crops.
Pharmaceuticals. Levulinic acid is used in anti-inflammatory medication, anti-allergy agents, mineral supplements and transdermal patches. DALA is used for diagnosis and treatment of cancer.
Personal care. Levulinic acid and its derivatives are used in organic and natural cosmetic compositions for antimicrobial, perfuming, skin conditioning and pH-regulating purposes.
Flavors and fragrances. Levulinic acid esters are often used as niche fruity flavor and fragrance ingredients.
The last time I spoke to Steve and his co-founder they had been going after the fuel additive angle and it was really difficult for them to gain traction. Perhaps in 2022 there might be more appetite for lower cost fuel additives. Here is an old white paper from Biofine about the market size for ethyl levulinate as a replacement for ethanol in gasoline. They estimated the market to be about $2.2 billion in the United States with a price of $1.88 per gallon, essentially an attempt to displace ethanol, which has it’s own issues.
There might be a deal there somewhere if Biofine Technologies is still kicking around as a company. You can reach out to Steve Fitzpatrick and his co-founder Mike Cassata if you are interested in investing.