The radical re-sourcing of tires, nylon, parachutes and balloons

Global Bioenergies achieves one-step renewable butadiene via fermentation.

Who’s in the global chase for a process to make one of the world’s Big 7 industrial chemicals via a renewable process — and how did Global Bioenergies just jump into the lead? The Digest investigates.

From France, news arrives that Global Bioenergies has succeeded in the production of bio-sourced butadiene by direct fermentation. That’s the first time, they say, a complete metabolic pathway has been achieved to produce renewable butadiene completely through fermentation.

Why it’s a big deal

Think tires. You can think eco-tires if you like — but whatever you do, think about expanding auto sales in Asia, which has left India, for one, very much in the import side of the equation on butadiene. Polybutadiene Rubber (PBR) and Styrene Butadiene Rubber (SBR) are two types of synthetic rubbers used globally to replace natural rubber.

But also think parachutes and clothing, as in 6,6 nylon. Butadiene is also a key intermediate chemical used by INVISTA for the production of adiponitrile (ADN), which in turn is a critical intermediate chemical used in the manufacture of nylon 6,6.

Capacity building is on, globally. LyondellBasell and BASF are building in the EU. But Asia is where the tire growth is.

The global market is over 10 million metric tons per year, and runs between $20B and $40B in value depending on current prices, which have been volatile. Overall, 7 million tons are used to manufacture rubbers; 3 million tons are used to manufacture nylon, plastics and latexes.

Why now, and what’s naphtha’s role in this?

ICIS has reported that 1.18m tonne/year of new plants are expected to come online in China this year alone. ICIS has also been reporting for the last couple of years now on destructive levels of volatility in naphtha prices — naphtha is the primary petrochemical feedstock for butadiene. Further, the growth in natural gas production — and prospects for more growth, especially to serve C2 markets such as ethylene, are expected to reduce naphtha production and further tighten the production outlook for C4 chemicals, especially butadiene.

The Global Bioenergies butadiene background

In this context Global Bioenergies announced a deal in 2011 with Poland-based Synthos to develop a new process for the conversion of renewable resources into butadiene, involving research funding, multi-million euro development fees, royalty payments, repartition of exploitation rights, and a $2M equity investment in Global Bioenergies.

Ultimately, if successful, Global Bioenergies would receive royalty payments from Synthos on bio-sourced butadiene used for the manufacturing of rubber, while retaining the exclusive rights for non-rubber applications, such as nylon, plastics and latexes, representing an existing market exceeding $6B.

Both parties had different responsibilities in the project as designed at the time, with Global Bioenergies taking care of research and process development at the laboratory level, and Synthos subsequently taking the process on to the industrialization stage.

The partnership’s progress next surfaced in December 2012, when the partners said they had discovered a direct biological pathway. Several patents have been filed to protect these biological assets. The success of that first phase triggered a €1.5M milestone payment to Global Bioenergies, and the project entered the development phase, for which Synthos contributed several million euros in total through annual fees. The goal? A production strain.

As of this week, Global Bioenergies has completed that step, and has a proprietary production strain. According to the company, the strain was placed in a lab-scale fermentation device, and upon the addition of glucose, the presence of butadiene in the off-gases was detected. This is the first time ever that the production of butadiene by direct fermentation from renewable resources has been reported.

Still a long ways to go

Jarosław Rogoża, R&D Director at Synthos noted: “We consider that the program is now significantly de-risked. We are looking forward to see how the program will behave in the next phase, dedicated to the optimization and scale-up of the process.”

The way forward

Global Bioenergies CTO Frédéric Pâques commented: “We now have in our hands a prototype process for the direct biological conversion of renewable resources into butadiene. We expect that this butadiene program will deploy in the next years as did our isobutene process, our most mature asset now operated in an industrial pilot. Direct fermentation of butadiene has major inherent advantages translating into better economics. We expect to demonstrate these in an industrial environment in the next few years.”

Elsewhere in the chase for renewable butadiene

Global Bioenergies and Synthos are far from alone in the chase — as a number of others have noted the expected shortfall in naphtha cracking and are looking for the magic biobased solution.

Genomatica, Versalis

In 2011, Genomatica announced a successful production of pound quantities of butadiene made from renewable feedstocks.  At the time, the milestone confirmed the technical viability of Genomatica’s bio-based manufacturing process. Butadiene is expected to be Genomatica’s second process after butanediol (BDO), also a C4 chemical.

Last year, Versalis and Genomatica announced the establishment of a technology joint venture for bio-based butadiene. The resulting process will be licensed across Europe, Asia and Africa by the newly-created joint venture. Versalis is also pledged to provide over $20M in funding to Genomatica to support development of the integrated end-to-end process.

Future licensees of the process, including Versalis, will provide the capital required for the construction and operation of their own plants, and be responsible for use and sale of the resulting butadiene.

Axens, IFP Energies nouvelles and Michelin

Axens, IFP Energies nouvelles and Michelin announced late last year the launch of a plant chemistry research partnership to develop and bring to market a process for producing bio-butadiene. They are also committed to laying the groundwork for a future bio-sourced synthetic rubber industry in France.

This project is the BioButterfly process, which will cover all R&D phases in the process, from scientific concepts, to the pilot phase and validation on an industrial demonstrator. BioButterfly is backed by a €52 million budget extending over eight years. The project was selected by France’s Agency for the Environment and Energy Management to receive €14.7 million in financing.

INVISTA, LanzaTech

In the summer of 2012, LanzaTech and INVISTA (think Lycra and Dacron) inked a joint development agreement to develop one-step and two-step technologies to convert industrial waste gas carbon monoxide into butadiene. Initial commercialization was expected in 2016, the partners said at the time.

In the long-term, the partners said they will focus on engineering LanzaTech’s organisms to make butadiene directly from gases; near-term, they will optimize what the organism already knows how to do – make 2,3-butanediol and then turn that into butadiene using a thermochemical conversion, which LanzaTech has already demonstrated in its work with Pacific Northwest National Laboratory.

Cobalt Technologies

In spring 2013, Cobalt Technologies announced a strategic relationship with two prominent, but undisclosed, Asian chemical companies for the development of butadiene from a range of biomass feedstocks. Under the terms of each strategic agreement, technology development is expected to be completed in 2014 with construction of a first commercial‐scale biorefinery in Asia, which would be expected to come onstream by 2015. In each case, the partners made an equity investment in Cobalt. Work to date has demonstrated, according to Cobalt, that the biomass-to-butadiene path can be highly competitive with petroleum‐based butadiene under current market conditions.

Amyris, Kuraray looking for novel subsitutes

Other partnerships are aiming at replacement via novel molecules. In the summer of 2011, Amyris announced a collaboration agreement with Kuraray to use Amyris Biofene to replace petroleum-derived feedstock such as butadiene and isoprene in the production of specified classes of high-performing polymers. Upon successful completion of the technical development program for the first polymer, Amyris and Kuraray said they will enter into a supply agreement for Kuraray’s exclusive use of Biofene in the manufacturing and commercialization of these polymer products.

The Bottom Line

One-step process for renewable butadiene? That’s a big deal for a major molecule — one of the 7 biggies. Lot of milestones standing between today’s announcement and production at scale though, and plenty of competitors in the field, so it’s premature to hit the “Game Over” button.

But think of it this way. Most major chemical companies talk in terms of 20-30 percent of global supply in the mid-to-long term coming from renewables — a sweet spot they believe will give the more control over fossil-sourced molecules.

If so, the global market for renewable butadiene could be something like 2-3 million tons in the long-term, or something like 20-30 full-scale commercial butadiene plants. So, there’s plenty of room for a little competition.