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Green Business Plan Competition: Start your engines

The ACS Green Chemistry Institute will be hosting a business plan competition on June 18, 2014 at the 18th Annual Green Chemistry and Engineering Conference, which will be held outside of Washington D.C.

The competition is for early stage ideas – but not ideas for renewable energy production or biofuels (there are no shortage of competitions for those). If you have an idea for a green innovation that only chemists would truly understand, this is your chance.

The first deadline to be aware of is April 25 – that’s when to submit your 10-15 slide PowerPoint presentation and optional YouTube video. Just aim to be done by Earth Day and you’ll be right on schedule.

The competition website includes a host of great links to advice on how to communicate and advance your start-up idea. And don’t forget to review (memorize them!) the 12 Principles of Green Chemistry.

Biobased Solvent: Strip paint, clean the oven – without getting dizzy

When you think of a typical “green” cleaner or bio-based surfactant, an image of mild, citrus-scented liquid dish soap might come to mind.

But you wouldn’t use that stuff to clean a year’s worth of burnt grease from your oven or wash the latex paint off your paint brushes. Usually, those kind of tasks call for cleaners that require significant ventilation.

Oven cleaners

Coming soon: Oven cleaners that don’t make you see spots. Credit: Elevance

But thanks to a collaboration between Stepan, a cleaning products ingredient maker, and Elevance, a biobased specialty chemical firm, consumers and professionals will be able to aggressively clean things without seeing stars.

Elevance and Stepan are talking about their first commercial product launched out of the collaboration called Steposol MET-10U. The firms say it can take the place of high pH alkaline degreasers in household cleaners, N-methyl pyrrolidone in adhesive removers, and methylene chloride in paint removers.

The product has a biorenewable carbon index of 75%. It is low VOC, with a boiling point of 297C, and can be used in much lower concentrations than the the solvents it replaces.

How is this done? Basically, Elevance uses olefin metathesis to create specialty building block molecules from waste oils (i.e. from oil palm farming). And those molecules can be very specifically functionalized for different uses, i.e. to create esters for surfactants, lubricants, and personal care products.

Of all the benefits of Steposol, it’s low volatility really makes it a winner, according to Andy Corr, Senior Vice President at Elevance. California has issued strict VOC regulations for many consumer products – for both human health and air quality reasons. Andy points out that even biobased ingredients, such as d-limonene made from citrus peels, can be very volatile.

And Robert Slone, VP of surfactant product development at Stepan, says this is only the first of many outcomes from the partnership, which formed back in 2010. “It is exciting to see the performance that we are able to achieve – chemistry that is much more environmentally responsible, less toxic, non-corrosive, and low VOC than the options that are out there currently.”


The Biology in Green Chemistry

Yeast, bacteria, enzymes, proteins… may not be what immediately come to mind with the phrase Green Chemistry. But of the 93 teams that have won Presidential Green Chemistry Awards, 31 had technology that hinged on the use of biological processes or biobased inputs, point out the folks at the Biotechnology Industry Association.

BIO has created a cheat sheet of sorts on the various bio-powered technologies behind past award winners, complete with summary blurbs and links to fuller descriptions. And it opens with the famous Twelve Steps, er, Twelve Principles of Green chemistry.

One of my favorites is the 1999 discovery by researchers at Dow AgroSciences of Spinosad, a selective insecticide derived from a soil microbe. It is a very relevant organic pesticide used today. The fun detail, not in the blurb, is that the microbe was found in the environs of a rum distillery. Why a scientist was looking there, in the dirt, is a fun question.

And more recently, a 2013 award went to Richard P. Wool of the University of Delaware who “has created several high-performance materials, such as adhesives and foams, using biobased feedstocks, including vegetable oils, chicken feathers, and flax.” These materials sound not-quite good enough to eat, but certainly quite good enough to sit on.




Big Companies Binging on Microbes

Microbes! They are tiny but powerful. And big companies are buying in – according to a wave of announcements that began late last week. Here are some highlights from my inbox.


Amyris in Brazil

Amyris has begun production of biobased farnesene in Brazil

Amyris, which has long been talking about making biofuels – particularly diesel and jet fuel – from its biobased farnesene, will embark on a joint venture with French fuel company Total. Recently Amryis had pulled back from its fuel ambitions, but now it will move ahead with this 50/50 venture. Total is already an investor in Amyris and owns 18% of the firm’s commons stock. Where’s the microbe? Amyris uses engineered microbes to make farnesene from sugar.


Meanwhile, Monsanto and Novozymes will combine forces to develop and market biological crop products based on microbes. The deal includes a $300 million payment from Monsanto for access to Novozyme’s technology, which the firm has been building for the last seven years. Microbes have long been used as inoculates for nitrogen-fixing legume plants but in the last few years microbial products have been developed to help with phosophate uptake, to fight fungus and insects, and promote plant vigor and yield. Interestingly, Ag giant Monsanto only last year introduced a microbial platform. This deal sounds like a way to catch up.

Biobased chemicals

Some microbes can ferment gases and make desirable chemical intermediates. LanzaTech has been an innovator in this space so we’ll start with that company’s new deal with Evonik. The firms have a three-year research agreement to develop a route to biobased ingredients for specialty plastics. The feedstock will be synthesis gas (syngas) derived from waste. LanzaTech has already begun production at an earlier joint venture that produces ethanol from the industrial waste gases of a large steel mill in China.

Invista is probably best known for its synthetic fibers business (think Lycra and Coolmax) but it also has a chemical intermediates business. And it now has a deal with the UK Center for Process Innovation to develop gas fermentation technologies for the production of industrial chemicals such as butadiene. The two are eying waste gas from industry as a feedstock. Rather than spin the work as a sustainability play, Invista says it may significantly improve the cost and availability of several chemicals and raw materials that are used to produce its products.


New Probe Aids Enzyme Mixology for Biofuels

What’s the difference between a bartender and a biofuels researcher? A bartender uses ethanol to make cocktails, while a biofuels researcher uses cocktails to make ethanol. Researchers at the Department of Energy’s Pacific Northwest National Lab have developed a probe to help create the most efficient cocktails for biofuels makers.

Trichoderma reesei

Trichoderma reesei, an enzyme powerhouse. Credit: Department of Energy

A biofuel-making cocktail is a blend of enzymes that break down biomass (like corn stalks). And apparently the fungus Trichoderma reesei is a veritable Swiss Army knife of enzymes.  T.E., as we’ll call it, is a mesophilic soft-rot fungus which was famous in World War II as the stuff that chewed through military tents in the Pacific Theater. It contains 200 sugar molecule busting enzymes (glycoside hydrolases) including 10 that chomp cellulose and 16 that consume hemicellulose. This variety is helpful, because no single enzyme can profitably make ethanol from cellulose.

To make biofuels, companies either make or purchase custom blends of enzymes that function at the needed pH, temperature, nutrient environment, and chemical conditions. Companies like Novozymes sell optimized blends of enzymes.

But with PNNL’s probes, cocktail DIY’ers can get in on the action. Currently, enzyme assays only show the total mixture activity of all enzymes, not the activity of individual enzymes. But the activity-based probe method quickly identifies and quantifies the activity of individual enzymes in a mixture, allowing high throughput analysis with gel electrophoresis or LC-MS-based proteomics. The research showed that the different processing conditions had a significant impact on the activity of individual enzymes. Armed with this knowledge, an enzyme mixologist would be able to more quickly identify the best ingredients for their biofuels process.

Reference [free download with registration at RSC]: Lindsey N. Anderson, David E. Culley, Beth A. Hofstad, Lacie M. Chauvigné-Hines, Erika M. Zink, Samuel O. Purvine, Richard D. Smith, Stephen J. Callister, Jon M. Magnuson and Aaron T. Wright, Activity-based protein profiling of secreted cellulolytic enzyme activity dynamics in Trichoderma reesei QM6a, NG14, and RUT-C30, Molecular BioSystems, Oct. 9, 2013, DOI: 10.1039/c3mb70333a.

Little Green Feedstocks

It sounds like something from a greenskeeper’s nightmare – certain folks have plans to grow algae and dandelions on purpose, and in large quantities.

Algenol's Paul Woods and his cyanobacteria. Credit: Algenol

Algenol’s Paul Woods and his cyanobacteria. Credit: Algenol

Firstly, in the golf course-choked state of Florida, Algenol CEO Paul Woods is scouting a location for a $500 million algae-to-fuels plant. The company was founded and has been operating in the southern part of the state for years now. Its claim to fame is cheap ethanol made from cyanobacteria in a custom-designed bioreactor. Woods does not, as far as I know, have plans to re-purpose stagnant water traps for the purpose of growing his feedstock.

But Florida, though it is sunny and warm, might have missed out on this slimy opportunity. In recent months, Woods questioned the state’s commitment to biofuels. For example, Governor Rick Scott repealed a state law requiring 10% ethanol in gasoline. But now, according to Fort Myers ABC 7 News, the company has been persuaded to build in its home state – apparently the estimated 1,000 jobs was just the ticket to getting a warmer welcome. Algenol needs to be sited near a major CO2 source (i.e., factory or power plant emissions) and says potential partners have come forward.

Meanwhile, it’s called the Russian Dandelion, though it grows in Germany. This common lawn scourge is bringing about not curses, but praise, for its rubber producing capability. Tire makers are enthused about its white latex sap. The goo is expected to give the subtropical rubber tree a bit of competition. Making rubber from dandelions is not a new idea, but has been given new life by a project at the Fraunhofer Institute for Molecular Biology and Applied Ecology.

Russian dandelions, growing in Germany. Credit: Fraunhofer Institute

Russian dandelions, growing in Germany. Credit: Fraunhofer Institute

Fraunhofer scientists, in a collaboration with folks from tire firm Continental are working on a production process for making tires from the dandelions. In addition to the manufacturing process, the researchers are also using DNA markers to grow new varieties of the plant with higher rubber yields.

The project sounds kind of cute but the researchers behind it are dead serious. The partners have already begun a pilot project and plans are afoot to move to industrial scale. According to them, the first prototype tires made from dandelion rubber will be tested on public roads over the next few years.

You can read an earlier post on the history of dandelion rubber here.

Harnessing Entropy

In Solar, a novel by acclaimed author Ian McEwan, the protagonist, a physicist named Michael Beard, has been tasked to evaluate submissions from the public sent to a UK panel looking for new ideas for clean energy. He divides them into piles: those that violate the first law of thermodynamics, those that violate the second law, and those that violate both. This cleantech reporter could relate.

That’s why ideas that start with the laws of thermodynamics – rather than those that have to account for them later – are so attractive. Take entropy, for example. In our daily life we struggle against entropy – the iPod headphone wires that get totally knotted up in my handbag, the fact that the neatest person you know still has a junk drawer, and so on.

This week’s issue of C&EN explores research that tries to harness the universe’s arrow-like movement to disorder. When CO2 laden emissions from power plants are released into the atmosphere, the CO2 mixes into the ambient air mass. As Naomi Lubick explains, an electrochemical cell could harvest the energy that is released when these two gases mix. Researcher Bert Hamelers of the Dutch water treatment tech center Wetsus, has developed a lab scale device to do just that.

But Lubick points out that to implement such a solution would require overcoming at least two hurdles – one, the sulfur dioxide and nitrogen oxides may foul the system’s membranes. And two, it is no easy task to dissolve huge amounts of CO2 in liquid.

Dissolving gas in liquid requires toil and trouble. Credit: Wikimedia Commons

Dissolving gas in liquid requires toil and trouble. Credit: Wikimedia Commons

In fact, dissolving the gas uses quite a bit of energy. Which reminds me of another literary reference: the witches of Shakespeare’s MacBeth chant “Double, double, toil and trouble; Fire burn and cauldron bubble” – indeed, there is some toil and trouble involved.

I know that many other researchers and technology companies are working on these two problems. For example, there are programs working on carbon capture and storage that are using liquids, catalysts and membranes to grab components of power plant emission gases. And firms such as Calysta Energy and Lanzatech have plans to use microbes to make useful products out of gases such as methane and flue gas. For that, they need to dissolve the gas in water. It is not a trivial problem.


Learning to Like Natural Gas

This week’s cover story – Seeking Biomass Feedstocks That Can Compete – discusses the competition that natural gas might bring to the young renewable fuels and chemicals industry. [You can also check out the YouTube video about Energy Cane]

The story discusses one positive that the rise of natural gas brings to biobased chemical makers – at least those that produce C4 chemicals (i.e. butanediol, butadiene). As the chemical industry swaps petroleum feedstocks for natural gas, their processes will generate a much smaller ratio of C4 chemicals. Firms that rely on those intermediates will seek other sources of C4s.

gas well

Green companies are looking at natural gas. Credit: Chesapeake Energy

But there are a few other ways that the natural gas story intersects with the renewable industries – some obvious, and some not so obvious. One obvious way – cheaper energy from natural gas may help decrease operating costs at all chemical producers, including ones that use biomass feedstocks.

Less obvious – there is a group of renewable companies that use syngas as a feedstock. You know what makes an excellent syngas? Why, that’d be natural gas. Sure, you could gasify plant matter, old tires, construction debris, municipal waste (anything carbon based). Any of those feedstocks will make a flow of carbon monoxide and hydrogen. With chemical or biological catalysts, that syngas can be made into chemicals and fuels.

At least two firms that started out with plans to make syngas from biomass or waste sources now say they will ramp up on natural gas – Coskata, and Primus Green Energy. Coskata’s end product is ethanol, while Primus is targeting drop-in hydrocarbons. Presumably, with a working gasifier and catalysts, they could switch feedstocks whenever the cost basis dictates.

Newlight Technologies wants to make polymers from waste gases like methane from water treatment plants. But methane from under the ground would work well, too. The company says it can also make polymers from CO2 (with a helping hand from a hydrogen generator). Which brings us to…

BASF, which is not really a renewable company, but has got some irons in the fire. The chemical giant has a research project going to rip the hydrogen off of natural gas, and mix that with waste CO2 to make a custom-blended syngas. The firm says getting hydrogen this way is cheaper than other ways (tearing up water molecules, etc). Waste CO2 is something many industries – especially in Europe – would like to do something with. LanzaTech is also in the waste CO2 business. Not sure what its natural gas plans are.

Lastly, two stalwarts of the biobased chemicals industry, Genomatica and OPX Bio are getting a handle on natural gas. Genomatica is working with Waste Management to make C4s from syngas (derived from municipal waste). The syngas project came up in my interview with Genomatica’s CEO Christophe Schilling about natural gas.

More directly, OPX Bio, which is working to make acrylic acid from sugar,  has a lab-scale project for its second product – fatty acids. The company says its process can use syngas made from all the usual suspects including natural gas. There is already a significant market for chemicals based on fatty acids; they can also be converted into nice things like jet fuel.

Natural gas is not a renewable resource, so one might wonder why these green tech firms would bother using it at all. I can think of three reasons: one – as a first feedstock to prove one’s catalyst technology, two, as an alternate feedstock to balance price and availability of biomass or waste, and three, as a way to fix the mass-balance of hydrogens and carbons in your syngas. If adding 10% of syngas increases yields by 20%, that might be tempting.

There is one way that natural gas as a feedstock might be considered “green.” This comes via Alan Shaw of Calysta. The company uses methane munching bacteria to capture natural gas, then enzymes in the cells can make desired products. Shaw suggests a good use of the technology would be to install small-scale units where there is so-called “stranded” natural gas. That would include oil wells that flare the natural gas that comes up with the crude oil in places like North Dakota.


The Gut(microbe)less Gribble – Biofuel Hero?

Behold the Gribble – a true gutless wonder. The Gribble (pictured here) is a marine wood-boring creature of around 2 millimeters in size. Scientists at the UK’s Biotechnology and Biological Sciences Research Council have been spending quality time with the Gribble because of its exceptional innards.

The Gribble lives in the sea and eats wood. Image: Laura Michie, University of Portsmouth

The Gribble lives in the sea and eats wood. Image: Laura Michie, University of Portsmouth

The tiny animal eats wood that finds its way into the sea. The wood can come from mangrove swamps or wash into estuaries from land. Gribbles, also called ship borers, have also been known to chow on wooden sailing vessels (including, rather famously, those of the Columbus voyages). “I’m sure they’ve taken down a few pirate ships, too” says Simon J McQueen-Mason a BBSRC researcher and materials biology professor at the University of York.

Most critters that eat wood or other lignocellulose plant material rely on symbiotic relationships with a diverse population of gut microbes – called the microbiome – to break down the tough-to-digest meal. When news reports suggest that pandas may hold the key to biofuels breakthroughs because they can live on tough bamboo, it’s really the microbes, and the enzymes made by the microbes, that are of interest.

(You can read a C&EN cover story about pandas, microbiomes and biofuels )

But the Gribble has no microbiome. And it doesn’t have the squishy, absorptive digestive system that most animals have. In fact, it digests its meals of wood in a sterile, hard-sided chamber in its hind gut. McQueen-Mason likens the environment to “a steel container you might use in an industrial lab.”

Instead of microbial helpers, the gribble has a separate organ where it produces the key enzyme itself. Termites do not do this (they have microbes). The gribble “must use quite aggressive chemistry; the enzyme is so harsh that it would kill any microbes” that might otherwise occupy the space, McQueen-Mason says.

The research team found the mystery organ and looked at the genes expressed there. Many of them encoded instructions for making what is called GH7 cellulase. This is a family of enzymes that are normally found in wood-degrading fungi. “These cellulases are abundant but were never reported in an animal before,” McQueen-Mason notes. “We were able to express the genes in a lab fungus and describe the properties.”

They also used X-ray crystallography to discover the structure of the enzyme and show how it binds cellulose chains and breaks them into small sugar molecules.

The GH7 cellulase, an enzyme made by the Gribble, breaks down cellulose into simpler sugars.

The GH7 cellulase, an enzyme made by the Gribble, breaks down cellulose into simpler sugars.

The Gribble’s enzyme appears to be very rugged and long-lasting, which is a good quality for an enzyme that might be used in an industrial setting to make biofuels from wood or straw, McQueen-Mason points out. It works very well in highly saline conditions and may also function well in ionic liquids. The use of salt water and ionic liquids for biofuels processing may cut down on the use of expensive, precious fresh water. And like a true catalyst, the enzyme may be reusable.
You can see a video of the Gribble  – which I highly recommend – it’s kind of cute.

For more on the enzyme, check out the journal paper: ‘Structural characterization of the first marine animal Family 7 cellobiohydrolase suggests a mechanism of cellulase salt tolerance’ www.pnas.org/cgi/doi/10.1073/pnas.1301502110.

Qteros: Back from the Dead?

Cleantech Chemistry HQ got an interesting e-mail yesterday. It stated that Qteros, an industrial biotech start-up of yore, has resurfaced. The firm had officially closed down earlier this year “because of adverse market conditions.”

Qteros’ technology was – and is – based on what the founders call the Q microbe. This critter is a two-in-one biofactory. It chomps down on biomass and also ferments the sugars into ethanol. It seemed that the firm’s microbe was well regarded, but the path to commercialization was murky. Cleantech Chemistry earlier reported that the firm was regrouping and maybe looking for a buyer.

That buyer, it turned out, was to be three of the company’s original founders. The firm was a tech spin off of the U. of Mass. Amherst. Original COO – and now CEO – Stephan Rogers of Amherst says “Having examined all the research, we now see an immediate pathway to commercialization with the current technology. The company is going to pursue a new and different, less capital-intensive business model. Part of our strategy to quickly get to market is to partner with others who have deep experience in microbial research to help us jump-start the process.”

Also at Amherst and still on the company’s scientific advisory board is Susan Leschine, who discovered the Q microbe. Qteros’ connection to the school will remain very cozy, it appears from the press release. It seems that the developers will move in with fellow researchers and will not seek out their own lab or office space until sometime in mid 2013. So it may be a little while before we hear more about the road forward.