A Replacement for Man

January 16, 2014 |

pope-manIs succinic acid’s path to success right through Maleic Anhydride (MAN)? 

And can it change the narrative for every biobased molecule replacing a fossil-based one?

And what does this exactly have to do with the poet Alexander Pope? We investigate.

When Alexander Pope opined in “Essay on Man” 1734 that the “proper study of Mankind is MAN,” he is likely not to have known very much about the production and distribution of Maleic Anhydride.

But he would have seen in the evolution from crude oil to biobased sources the principle of optimization at work, and he would have found much to approve of in the progress towards new sources and strategies. It is to a great extent a practical variation on “what will be, is better” — and in keeping with his philosophy.

If you too find yourself less than familiar with Maleic Anhydride, Myriant offers this helpful explanation:

“Maleic Anhydride (MAN) is an organic chemical intermediate that is used in the production of butanediol, or BDO, another chemical intermediate used to make food packaging, specialty fibers such as Spandex and Lycra, as well as popular adhesive tapes and polyurethane foams. Petroleum-derived MAN is often made from benzene, a known carcinogen.

“Myriant has partnered with Johnson Matthey – Davy Technologies (JM Davy), one of the world leaders in the production of MAN-derived BDO, to demonstrate that our bio-succinic acid can be utilized in JM Davy’s process as a direct replacement for MAN.

“Combining the efficiencies of Myriant’s bio-succinic acid process and the JM Davy BDO/THF process, the bio-butanediol and bio-tetrahydrofuran has an overall carbon efficiency of 87%, believed to be substantially better than the carbon efficiency achieved in the direct fermentation route to bio-butanediol. JM Davy will also provide process and performance guarantees for commercial grade bio-butanediol, bio-tetrahydrofuran and bio-gamma-butyrolactone made from Myriant’s bio-succinic acid.”

Now, there are a range of claims in there — but one of them is well understood by a number of companies. That is, that the cost structures for biosuccinic acid make it possible to use it to lower the cost and reduce the hassle of making BDO. Which is to say, a better way to make Spandex, Lycra, popular adhesive tapes and polyurethane foams among other products.

Now – generally the biobased narrative is structured by critics around a series of mandates, backed by subsidies, forcing companies to bend or replace current infrastructure in order to use novel molecules that cost more, spread poverty, wreck the environment, and ruin just about any machine they are introduced into. In order to hand millions to some corn farmers.

So, the problem of MAN is a vexing one.

It replaces a process that costs more. The new process is surrounded by no mandates or subsidies, uses existing infrastructure, costs less, reduces poverty, helps the environment, and works just fine in any machine or with any person.

In a related development — in this case, biobased rubbers used in wetsuits — Jason McCaffrey, business director of Patagonia surf wear, told KJZZ radio that surfers trying biobased wetsuits made from 60 percent guayule resin content “would put it on and use it for surfing and they would have no idea that there was a difference performance wise. It’s almost impossible to tell with the exception of Guayule suits smell way better than the traditional neoprene suits.”

What makes the difference?

Why — when the challenges of making competitive drop-in fuels from biobased sources are so well known, and dependent on feedstock costs, is biosuccinc acid competitive in today’s market, even at small production volumes.

In a word, oxygen.

Which is to say, succinic acid has a bunch of it. So does biomass. But hydrocarbons coming out of a barrel of crude have none. To make succinic acid — or, any of the organic acids — from hydrocarbons you need to add oxygen. So, it adds a process step — and if you need pure oxygen instead of ambient air (which is 80 percent nitrogen), then you have some cost challenges.

By contrast, making organic acids from biomass — there’s no need to blow off the oxygen.

The production of biobased succinic acid

succinic-1

Last year, our friends at WEASTRA in their report on succinic acid for the “7th Framework Programme of the European Union, FP7 – Knowledge based Bio-Economy Collaborative Project,” noted that the market for succinic acid was roughly 40 kT (kilo tonnes) per year of which just 1.15 kT of production capacity was biobased.

The players in the market? So far, Myriant, the BASF-PURAC joint venture, and Reverdia (a JV of DSM and Roquette).

But capacity is on the way. In fact, WEASTRA projected 225.87 kT by 2014, with Myriant, BioAmber, BASF and Reverdia all in the mix.

The prices?

The prices are pretty good, especially when you consider prices in the fuel sphere (where gasoline fuels cost roughly $900-$1100 per tonne). Petroleum based succinic in 2011 was valued at $2400-$2600/T with biobased getting a 10-15% price premium at demo-scale volume.

What can you make with low-cost succinic?

Now, there isn’t going to be a huge market for $2600 per tonne biobased succinic as a base chemical for making other chemicals with big markets. If that were the case, the petroleum guys would be doing it right now.

succinic-2

And that’s the potential. By reducing the costs, new markets opens up when succinic can act as a route to other chemicals that have more established applications.

What are those?

Well, there is the aforementioned market in BDO. And four other markets: PBS and PBST; polyurethane as a replacement for adipic acid; alkyd resins; and plasticisers as a replacement for phthalic anhydride; and solvents.

The real markets of interest?

According to WEASTRA, 97% of “addressable” market volume potential will be concentrated in four markets: Plasticizers, BDO, polyester polyols and alkyd resins — and they predict that biobased producers will capture 10% of that market, or 599 kT per year. That is to say, these are the markets where succinic might play a role in the future, if the new technologies prove to be the winners.

How much will succinic capture by 2020. WEASTRA expects 10% of that addressable market (599 kT), most of that in BDO (316 kT). The big market in plasticizers, replacing PA (pthalic anhydride) will come along later.

One problem area?

Adipic acid — foreseen as a big market for biobased just a few years ago, and in WEASTRA’s analysis — but the shale gas and tight oil boom is likely to curtail the opportunity substantially, and companies like Verdezyne have downshifted on efforts on that front.

That, er, other route

When we think BDO, we also think “Genomatica”, which has been licensing its BDO process like crazy, with the likes of BASF getting underway at commercial scale, and companies like Toray and Lanxess bringing along their efforts quickly.

Bottom line? We expect that a number of players will opt for the Genomatica direct route to BDO, but the market is growing so fast that it is likely that all players will have a role, especially if oil prices remain high and bio-feedstock prices keep steady, and the incumbent becomes easier to beat.

The players

succinic-4

BioAmber

BioAmber is expected to complete commissioning in 2014 of a new biosuccinic acid plant, now under development in Sarnia, Ontario.

“We have begun early works on the site in Sarnia including hooking up to the water and sewer system under Vidal Street,” the company’s Executive Vice-President Mike Hartmann told the Digest in late 2012. “The $80 million project is being constructed at the LANXESS Bio-Industrial Park in Sarnia. The site is located in a large petrochemical hub with existing infrastructure that facilitates access to utilities and certain raw materials and finished product shipment, including steam, electricity, hydrogen, water treatment and carbon dioxide,” the Sustainable Chemistry Alliance newsletter reported.

BioAmber has been producing bio-based succinic acid in a large-scale facility in France since January 2010. The facility is one of the largest bio-based manufacturing fermenters in the world thanks to its 350,000 liter commercial-scale fermenter.

BASF-PURAC (Succinity)

BASF and Purac, a subsidiary of CSM, are establishing a joint venture for the production and sale of biobased succinic acid. The company will be named Succinity GmbH and will be operational in 2013, with an annual capacity of 10,000 metric tons.

The two companies are currently modifying an existing fermentation facility at Purac’s Montmélo site near Barcelona, Spain.  This is complemented by plans for a second large-scale facility with an annual capacity of 50,000 metric tons of succinic acid.

Reverdia

Early in 2010 DSM and Roquette opened a demonstration plant in Lestrem (France), which has been running at full capacity. In 2010 DSM and Roquette also announced their intention to establish a joint venture (which will be carrying out business under the name Reverdia) for their cooperation, subject to regulatory approval. In 2011, DSM and Roquette Frères announced a commercial scale plant for the production of bio-based succinic acid.

In December 2012 the plant commenced operations in Cassano Spinola, Italy, at a commercial-scale plant producing Biosuccinium sustainable succinic acid. The plant has a capacity of 10,000 tonnes/yr. Key applications for Biosuccinium include polybutylene succinate (PBS), polyester polyols for polyurethanes, coating and composite resins, phthalate-free plasticizers, and 1,4 butanediol. End products include footwear, packaging and paints.

Myriant

Last June, Myriant announced the successful start-up at its flagship bio-succinic acid plant located in Lake Providence, Louisiana. Myriant has produced on-spec commercial product at the plant and the Company anticipates that customer shipments will commence soon. Myriant’s bio-succinic acid plant is the first of its kind and scale in North America and has an annual nameplate production capacity of 30 million pounds of bio-succinic acid.

Myriant’s Lake Providence Commercial Facility is partially funded through a $50 million cost sharing cooperative agreement received from the United States Department of Energy (DOE), $25 million from the United States Department of Agriculture (USDA) B&I Loan Guarantee Program and a $10 million grant from the Lake Providence Port Commission and the Louisiana Department of Transportation.

The bottom line

We think of it in terms of the 1968 Zager & Evans song “In the Year 2525”:

In the range of $2525, if MAN is still alive

If the magic bug survives, biobased will thrive


In the range of $3535
ain’t gonna use succinic made from oil
and the isoprene you need
will come from hybrid guayule seed
whoa-oh

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