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Category → Bio-based Chemicals

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 Growth Seen for Biobased Materials and Chemicals

Technologies for – and commercialization of – materials and chemicals made from a variety of biobased feedstocks “have reached an inflection point” and are poised to grow significantly over the next four years, according to the minds over at Lux Research.

Rubber Duck

Just Ducky. Biobased capacity, like for non-phthalate plasticizers, has a bright future

Research analyst Julia Allen says overall capacity will nearly double, reaching 13.2 metric tons in 2017.  Growth rates by segment vary but all are robust, spanning intermediate and specialty chemicals and polymers. The biggest percentage growth, and largest category of production, will be for intermediates like adipic acid and that old fashioned biobased product, lactic acid.

The only fly in the punch mentioned in the press release (full report available to Lux clients) is that cellulosic feedstocks are likely to continue to grow  slowly. Corn starch and sugar cane will still dominate, and oily bio feestocks and waste gas will also play a role.

Here’s a nice example of the biobased industry’s maturation. One of the larger biobased chemical intermediate companies is Myriant, a producer of succinic acid made from sugar. Today the company said it has supplied commercial quantities to downstream customer Oxea for use in production of pthalate-free plasticizers. Oxea is a large-ish intermediates company owned by Oman Oil Company. Applications for the plasticizer include food cling wraps, flooring, soft toys and adhesives & sealants.

Of course, just because the industry as a whole is on surer footing and poised for growth, does not mean the same is true for individual companies. In fact, once the market is in a position to determine demand and pricing, we may see what business reporters politely call “consolidation.”

For instance, Florida-based biobased specialty chemical company LS9 was recently bought by mainstream biodiesel fuel maker Renewable Energy Group for a not-huge price tag. And biobased plastics supplier Cereplast has filed for Chapter 11 bankruptcy just this week.

Genomatica Partners up the Slope of Enlightenment

This has been a big season for biobased chemicals firm Genomatica. In late November, BASF announced that it used the company’s engineered microbe fermentation technology to scale up renewable production of 1,4 butanediol (BDO). And earlier this week, Genomatica announced a new partnership with Brazil’s Braskem to begin manufacture of biobased butadiene, starting with a pilot plant.

Genomatica's biobased butadiene.

Genomatica’s biobased butadiene.

“We’re tremendously excited,” said Genomatica CEO Christophe Schilling yesterday, in a chat with Cleantech Chemistry. “We’re positioning ourselves to get to this point – for many years we’ve viewed ourselves as the partner for the chemical industry when it comes to using biotechnology as a way to make chemicals. Not just for BDO or butadiene but for a broad range of chemicals.”

But we at the blog have noticed that these days, news like this just does not meet the same level of excitement that it would have back in say, 2010.

“It really reflects the state of cleantech now – people are struggling with ‘where did all the enthusiasm and energy go?’” says Mark Bunger, an analyst at Lux Research. “It is a natural part of how technology evolves. Initially there is a lot of hype, then you see a trough of disillusionment, followed by a plateau of interest.”

Bunger says all technologies tend to follow this pattern first identified by IT consultancy Gartner. It is called the hype cycle. Certainly, the last two years have been trough-like in the excitement level. After a certain number of years pass, when a company does prove that its technology works, it may be met with a bit of a shrug.

Gartner Hype Cycle

Gartner Hype Cycle. Credit: Wikipedia

To get out of the trough of disillusionment, according to the Gartner theory, requires surviving a shakeout where some technologies don’t prove themselves. Investments continue if the surviving firms show that early adopters are satisfied with the technology’s results. The two Genomatica news items show that the firm has likely passed this barrier.

To then climb the slope of enlightenment and get out of the trough, Genomatica will have to show more than one instance of the technology benefiting a large enterprise and commercialize second- and third-generation products. This is where Genomatica is heading with its partners.

The goal, in the end, is for mainstream adoption to take off (the Plateau of Productivity). Genomatica, and other producers of C4 chemicals, says that the shale gas boom will provide a timely market pull for their technologies. The reason? Petrochemical plants that use “light feedstocks” such as natural gas produce a much smaller ratio of C4 chemicals than facilities that use crude oil. We’ll find out in the next few years whether the tail-end of the biobased chemicals hype cycle will fit nicely with the peak of the shale gas hype cycle.

 

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.

Fuels

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.

Agriculture

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.

 

M&G Paves the Way for Coke’s PlantBottle in China

Cleantech Chemistry thanks C&EN colleague Marc Reisch for contributing this news about biobased chemicals.

M&G Chemicals, a unit of Italy’s Gruppo Mossi & Ghisolfi, plans to build a $500 million biorefinery in China to make ethanol and the polyester raw material mono-ethylene glycol from 1 million metric tons of biomass per year. The facility in Fuyang, Anhui Province, China, will be four times larger than M&G’s recently commissioned Crescentino, Italy-based biorefinery when it is open in 2015.

To be built in a joint venture with minority partner Guozhen Group, a Chinese energy and real estate conglomerate, the Fuyang refinery will use Proesa technology from Beta Renewables, a joint venture partly owned by M&G which is also a polyethylene terephthalate maker.

M&G’s CEO Marco Ghisolfi says the Fuyang refinery “is the first act of a green revolution that M&G Chemicals is bringing to the polyester chain to provide environmental sustainability.” The company’s entry into China will ultimately position it to supply PET to firms such as beverage maker Coca-Cola which have advanced the development of renewably-sourced bottles, among them Coke’s own “PlantBottle.”

Coke currently buys ethanol-based ethylene glycol from India Glycols to make a PET bottle that is nearly 30% biomass derived. To increase feedstock availability, last year Coke formed a partnership with India’s JBF Industries to build a 500,000 metric-ton-per-year bio-ethylene glycol plant in Brazil, also set to open in 2015.

While the JBF plant will use sugarcane and sugarcane-processing waste as feedstock, M&G’s China facility will be based on wheat straw and corn stover. So M&G’s plant has the added virtue of depending on a non-food feedstock source.

But the ethics of using one feedstock crop versus another, or of using biomass versus petrochemical feedstocks, might not matter if consumers don’t care. At the BioPlastek Forum, a conference held in June, Coke, Ford Motor, and yogurt makers Danone and Stonyfield Farm told bioplastic makers that most consumers are unwilling to pay higher costs for bioplastics (C&EN, July 15, page 18).

And while the large M&G and JBF plant may have the economies of scale to drive down bio-based PET costs, they’ll encounter headwinds from petrochemical-based ethylene glycol makers. Lux Research senior analyst Andrew Soare points to the spate of ethylene and derivatives plants planned in the U.S. based on low-cost natural gas. M&G itself, for instance, is building a 1 million metric-ton-per-year PET polymer plant in Corpus Christi, Texas.

However, M&G will be challenged to make cost competitive ethylene glycol in China given the competition expected from U.S. petrochemical producers, Soare says.

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.

 

Choppin’ Broccoli

In the quest for chemicals and fuels made from biomass, there are a few important black boxes that make it difficult to compare different companies’ business models and likelihood of success. One of them is the process by which a particular facility obtains sugars from its biomass feedstock.

In many cases, the first step is expensive, but low-tech – chopping up the stuff. This is the part that reminds me of Choppin’ Broccoli, the Saturday Night Live song as performed by Dana Carvey. Since cellulosic ethanol is sort of an offshoot of corn ethanol, it’s helpful to imagine how different it is to process a corn cob or stalk or an entire sugar cane, compared to grinding up a starchy corn kernel. Getting sugar from cellulose is difficult enough, getting the cellulose away from the clutches of a plant’s lignin first requires heavy machinery to chop it into little pieces.

So say you have tidy chipped up pieces of biomass. What do you do then? Like the SNL song, it ain’t pretty. Generally it requires some combination of thermochemical assaults to get the sugar out. Steam, alkali-acid washes, and pricey enzymes… In an otherwise green business, the pretreatment steps use energy and possibly chemicals that you wouldn’t want to spill.

Since pretreatment of biomass has a lot to do with both costs and the yield of sugars from feedstock, it is a busy area of research. An article by Chris Hanson in the appropriately named Biomass Magazine delves into some intriguing ideas. To release the useful cellulose from lignin, researchers at University of Illinois at Urbana-Champaign and the U.S. DOE’s Joint BioEnergy Institute are investigating ionic liquids. Instead of using a traditional, two-stage alkali-acid pretreatment, a dose of butadiene sulfone got the job done in one step, according to U. of Illinois scientist Hao Feng. Another major benefit is that the butadiene sulfone can be recovered and recycled.

In California, the JBEI has been experimenting with imidazolium chloride. It has succesfully obtained sugar yields of 95% from mixed feedstocks and recycled 95% of the ionic liquid.

And a company called Leaf Energy has been studying a glycerol pretreatment method. Compared to acid pretreatments, the company says their method gets more sugars faster by dissolving lignin with a relatively inexpensive reagent with low temperature and standard pressure.

The goal with improving pretreatment steps is to bring down the cost of sugar from cellulose so that it is not more expensive than sugar from corn or sugar cane. Maybe if major cellulosic ethanol producers take up these technologies, we’ll have a better window into how they get the sugar out.

 

Biobased Chemicals: Some growing pains

Gevo, a maker of bio-based isobutanol, is now actually making isobutanol. It says something that a publicly-traded company has been not making its commercial product for some months. The problem was a bug in the production system – technically a microbe – a microbe other than the one (a yeast) that was supposed to be making isobutanol.

I spoke with Gevo’s CEO Pat Gruber yesterday at the BIO show in Montreal. He was rather forthright about what happened. First, they were running the plant at full scale with their own yeast and had their separation process running. They were producing truckloads of isobutanol. The facility had previously been an ethanol fermentation plant. With the new operating conditions, a dormant microbe sprang to life, contaminating the process. The product was still being made but the company decided to shut down the plant and decontaminate it.

“We had to identify the sources of the contaminant, change the pipes, sanitize the equipment, train the staff and modify the operating conditions to favor our yeast,” Gruber recounted. He emphasized that these plants are not sterile like a pharma plant would be. Instead, vectors of contamination are controlled so they stay at very low levels.

When I wrote about biobased chemicals last summer, analysts held out Gevo as an example of a success story. It was shortly after the story ran that Gevo stopped its process at its Luverne, Minn. plant due to problems with contamination. The episode shows the kind of growing pains that the industry and its followers are learning to anticipate and accept.

Other companies might face different kinds of growing pains – for Gevo there was what is called technical risk. Other firms are making chemicals such as biosuccinic acid. They also face a market risk because for most applications their product is not a drop in raw material, so downstream customers must adopt it.

This year is the tenth anniversary of the World Congress for Industrial Technology. Historically, it seems to take about a decade for a new chemical concept to reach commercialization, and then some more time to penetrate new markets. This makes 2013 a very interesting year for the biobased chemical industry.