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Invista, LanzaTech on bio-butadiene

Bio-based butadiene development is getting hotter as another announcement, this time from LanzaTech, came out right in the heel of Genomatica's partnership announcement with Versalis.

LanzaTech said it has partnered with global nylon producer INVISTA to produce bio-based 1,3 butadiene (BD), first by a two-step process using LanzaTech's carbon monoxide-based 2,3 butanediol (BDO); and in the long-term, by directly producing carbon monoxide-based butadiene in a single step process using gas fermentation.

The companies plan initial bio-BD commercialization using the 2,3 BDO route to BD by 2016.

According to INVISTA, they will use the bio-BD as feedstock for their proprietary adiponitrile (ADN) production technologies. ADN is an intermediate chemical used in the manufacture of nylon 6,6.

INVISTA said developing a cost-competitive biological route to BD will help assure ample supply and reduce price volatility of the chemical.

INVISTA claimed that its proprietary butadiene-based ADN production technologies are already widely recognized as one of the most effective and cost-efficient methods of ADN production. More than 75% of the world's existing ADN capacity uses the INVISTA technology, the company said.

The blog has yet to talk to INVISTA but we did had a brief conversation with LanzaTech last Friday with regards to this announcement.

According to LanzaTech CEO Jennifer Holmgren, the companies will initially focus on using 2,3 BDO to BD process as LanzaTech has already been able to produce 2,3 BDO, and that it will take further genetic tweaking of their existing organism to be able to directly produce carbon monoxide-based BD via gas fermentation.

"Right now, we can already economically produce 2,3 BDO that can be used to make butadiene. We decided to start commercializing this biochemical route to BD now while we further develop the other process." - Holmgren

LanzaTech and its partner, US-based Orochem Technologies, believe they have a separation route that can economically convert LanzaTech's CO-based 2,3 BDO into 1,3 BD using a thermocatalytic process.

Holmgren said the 2,3 BDO-to-BD development project will be done in LanzaTech's pilot facilities in Chicago, US, and in New Zealand. LanzaTech currently has a 15,000 gal/year pilot facility at a steel mill in New Zealand that produces ethanol and BDO from waste CO gas.

Going back to my previous interview with LanzaTech in May, Holmgren noted that their gas fermentation technology can produce up to 50% of 2,3 BDO by volume and the rest in ethanol.

The 2,3 BDO market is currently very limited because of the difficulty of separating the intermediate into downstream derivatives such as BD, methyl ethyl ketone (MEK) and butenes.


2,3 BDO is currently available as a laboratory chemical and is being sold as a small-volume intermediate for certain niche applications such as in food flavoring additives. In the past, 2,3 BDO was used as a feedstock to make butadiene for synthetic rubber, before it was abandoned in favor of a more cost-effective naphtha-based BD.

According to LanzaTech and Invista, they will also collaborate on direct production of other chemicals including nylon intermediates using CO waste gas. When it comes to producing nylon, potential bio-based chemicals that came to the bloggers's mind include adipic acid,

The blog has not really gotten that much press release from INVISTA in the past although we did posted a brief announcement last May about the company's improved butadiene-to-ADN processing technology, where INVISTA said the new technology is a culmination of more than $40m in R&D spanning four years.

Benefits of the new ADN technology, according to INVISTA, include improved product yields, reduced energy consumption, lower CO2 emissions, enhanced process stability and reduced capital intensity compared to existing technologies. The new ADN technology also virtually eliminates benzene from the production process.

The blog wonders if this "new technology" is already pertaining to the use of CO-based butadiene?

INVISTA said in their May press release that it has been operating this new technology for more than two years at a pilot scale facility at its R&D center in Orange, Texas, and that it has now the option of installing the new technology at its existing facilities in Orange and Victoria, Texas, in addition to a plant INVISTA is constructing in China.

I guess it is a time to knock on INVISTA's doors and get some answers.

In the meantime, with two recent bio-butadiene announcements, the blog asked LanzaTech on the benefits of CO-based BD as opposed to biomass-based BD.


"Part of the reason why we have been so successful in gas fermentation is that our technology is outside the whole sugar value chain. Another advantage is that gas is a continuous process unlike sugar fermentation where most I know is based on batch processing.  
We get to leverage the whole petroleum/chemical processing systems where a lot of production is under continuous process --which is more efficient if you do it right." - Holmgren. 


The blog had an interesting conversation with LanzaTech this morning which will be posted next week Monday. In the meantime, my apologies to the readers for letting this news about BioAmber and Evonik slipped out.

The two companies announced on July 24, about their long-term partnership in the development and manufacturing of catalysts for making 1,4 butanediol (BDO), tetrahydrofuran (THF) and gamma butyrolactone (GBL) from bio-based succinic acid.

According to BioAmber, it has licensed a BDO hydrogenation catalyst technology from DuPont in 2010, which has been further developed with partners Evonik and the Center for Applied Catalysis at Seton Hall University based in South Orange, NJ, USA. At the same time, BioAmber and Evonik have also started developing a new generation of BDO catalysts.

Now, the blog has no clue on what type of catalysts are usually being used to produce BDO from succinic acid unfortunately. But what the blog remembers is that Myriant is also looking at producing bio-succinic acid-based BDO with its partner Davy Process Technology, an engineering and technology company.

According to US consulting firm Nexant, the Davy approach is to convert succinic acid to dimethyl ester first and then undergo vapor phase hydrogenolysis to BDO/THF mixtures.

Back to BioAmber, the company along iwth its partner Mitsui is currently planning to start a 23,000 tonnes/year of bio-succinic acid-based BDO in late 2014 in Sarnia, Canada. BioAmber said the global market for petrochemical-based BDO, THF and GBL is $4bn.

I am still working on the weekly news roundup but this news about waste-to-energy keep popping up on my email inbox so we might as well take a brief look and see what's going on in this sector.

I have written an article on ICIS Chemical Business about the waste plastic-to-energy market last year where Dow Chemical is one of the companies looking into the PTF (plastic-to-fuel) technology. Some of the companies involved in this field include Agilyx. Plastic2Oil (JBI) and Nexus Fuels, according to the American Chemistry Council (ACC).

According to a January study prepared by research firm RTI International for the ACC, there are two types of advanced conversion technologies being used in this industry: gasification and pyrolysis. The primary difference between the two is the feedstock used.

Pyrolysis technologies are generally suited to handle feedstock from non-recycled plastics while gasification accepts all municipal solid waste (MSW) including non-recycled plastics.

According to the study, gasification of MSW saves 6.5m to 13m BTU/ton and 0.3-0.6 tons of carbon equivalent emissions per ton compared to landfill disposal. Pyrolysis, which converts plastics to oil or gas, saves 1.8-3.6m BTU/ton and 0.15-0.25 tons of carbon equivalent per ton over landfill disposal.

RTI identified 41 advanced conversion technology facilities that are under development or undergoing demonstration in North America that that will accept MSW or non-recycled plastics as feedstocks.

Vendors of pyrolysis technology includes Agilyx, Envion, Global Climax Energy, JBI. Gasification technology developers include Enerkem, Plasco, Ze-gen, Geoplasma. Most of these companies are definitely new to the blog!

Anyway, just today, US-based industrial gas company Air Products announced that it will build and operate the world's largest renewable energy plant in the UK using the Westinghouse advanced gasification energy-from-waste (EfW) technology provided by AlterNRG.

The Tees Valley plant located near Bilingham, Teesside, will have a capacity of 50MW and is expected to power up to 50,000 homes. According to Air Products, it will divert up to 350,000 tonnes/year of non-recyclable waste from landfill. The facility is expected to start operation in 2014.

Proposed Air Products facility

New companies that caught the blog's attention also includes Nexterra Systems, which just dedicated a biomass gasification energy plant late last month at the US Department of Energy's Oak Ridge National Laboratory (ONL) in Oak Ridge, Tennessee; NY-based ZeroPoint Clean Tech, which already deployed two biomass gasification systems, one in Ireland and the other in Germany; and Covanta Energy, which completed its commercial demonstration testing of its gasification technology in April.
 

Covanta Energy's gasification unit can process 350 tons/day of post-recycled municipal solid waste which does not have to be pre-treated.


I am still trying to catch up with news from last week and here was another big one that came from bioplastic producer Metabolix.
 

If readers recall, Metabolix had a fall out with Archer Daniels Midland (ADM) early this year and had since then been looking for alternative plans to produce its polyhydroxyalkanoate (PHA) resins dubbed Mirel.

The company announced on July 26 that is has signed a letter of intent with Spain-based Antibioticos S.A. to produce Mirel at its manufacturing facility in Leon. Metabolix said "it will begin work immediately with Antibioticos to conduct a series of validation production runs to demonstrate fermentation and recovery of Mirel biopolymer resin on full production-scale equipment at Antibioticos."

Based upon the validation production runs and completion of economic and engineering feasibility studies, Metabolix intends to enter a definitive contract manufacturing deal to produce Mirel.

If Antibioticos sounds familiar to you, it is because this Spanish penicillin producer has formerly been working with Amyris on planning to commercially produce sugar-based farnesene molecules. Early this year, Amyris scrapped its plans with Antibioticos.

According to an ICIS news article (subscription required) written by colleague Clay Boswell, Metabolix expects commercial supply of Mirel from Antibioticos' plant to begin in 2013. Metabolix aims to initially produce 10,000 tonnes/year of Mirel through Antibioticos, a scale that Metabolix said is sufficient to supply existing customers while continuing to develop the market.

Metabolix said it still has existing inventory of 5m pounds of Mirel produced from ADM's Clinton, Iowa, plant.

During its second quarter earnings call also on July 26, Metabolix noted that it has also started shipping sample quantities of dried biomass for conversion to bio-based acrylic acid for customer evaluation. The company reportedly had a successful scale-up recovery of acrylic acid from dried biomass in Metabolix's Cambridge laboratory in the second quarter of 2012.

The company so far has been confident with the development of its C3 and C4 chemical platforms this year. According to a recent Jefferies analyst report on Metabolix, the company estimated benchmark potential manufacturing costs for the PHA-based gamma butyrolactone (GBL) at around 50c.-60c./lb and for PHA-based 1,4 butanediol (BDO) at 80c.-90c./lb.


Genomatica Withdraws IPO

Christophe Schilling, Genomatica CEO
So the blog found out yesterday that Genomatica withdraws its $100m IPO (initial public offering), which it registered with the US Security and Exchange Commission (SEC) in August last year.
 

Unfortunately, the news was under embargo so I was not able to post it immediately. According to Genomatica's SEC statement today, the company withdrew the registration "in light of current market conditions."

The company was also able to secure a private funding worth $41.5m from new investor (and partner) Versalis -- an Italy-based chemical company, and existing investors Alloy Ventures, Draper Fisher Jurvetson, Mohr Davidow Ventures, TPG Biotech, VantagePoint Capital Partners and Waste Management.

In my interview with Genomatica CEO Christophe Schilling yesterday, he noted that the company is also focusing its business model more on licensing its technologies as opposed to operating assets.

"In view of the current market environment, the private financing will give us better opportunity to demonstrate our technology and differentiate our business model. Our business model is more like a UOP-type licensing model as opposed to operating assets. We are positioned to offer process technology, not a producer of chemicals." - Schilling
Still, Schilling said it will still enter the public market again if opportunity exists as the company moves forward.

According to Genomatica, the $41.5m financing will be used partly for commercialization of the company's 1,4 butanediol (BDO) technology as well as expanding the company's portfolio including the newly announced bio-based butadiene (BD) development with Versalis.

Speaking of this partnership, Genomatica wants to clear out some of the blog's musings on this deal. It seems that there are other routes and processing that can produce butadiene aside from using 1,4 BDO or 2,3 BDO, which the blog posted before.

Schilling said they will not use 1,4 BDO or even 2,3 BDO to produce butadiene for this partnership with Versalis and Novamont.

"At this point, all we are comfortably sharing is that Genomatica has multiple technologies that it is developing to produce butadiene. As far as specific technology and the routes that we are developing, we are not disclosing those. We've done 1,4 BDO to butadiene but we think that there are some better ways to make a lot more economical sense to produce bio-based butadiene and even better than using 2,3 BDO as well. Versalis has understand and has seen this value, hence the partnership." - Schilling
More interesting tidbits from the interview:

  • The 40m lb/year planned commercial bio-BDO facility between Novamont and Genomatica is completely separate from the Versalis partnership. This facility is located in Adria, Italy, and is expected to initially produce bio-BDO in 2013.
  • When asked if the Matrica joint venture (Versalis and Novamont 50/50 partnership) will consider producing bio-BDO at Porto Torres in Sardinia, Italy, Genomatica said it has not disclosed this type of information. (In short, no comment).
  • Genomatica also did not talk about any timeline for the production of bio-butadiene with Versalis, although my colleague Andy Brice had an exclusive interview with Versalis CEO Daniele Ferrari. According to his article on ICIS News (requires subscription), the partnership will be capable of industrializing at least part of the bio-butadiene processing technology within the next 2-3 years, with a plant possible within 4 years.
"At the moment we don't have a precise location for any plants but obviously it has to be close to an agricultural supply chain and supply of biomass, and has to be close to the elastomers business in the future. We don't know about the size of the plants at the moment because we need to decide on the process and technology first." - Versalis' Daniele Ferrari.


So the blog just had its interview with Genomatica with some juicy details, which unfortunately, will have to wait until tomorrow.

In the meantime, bio-butanol producer Cobalt Technologies announced today that it is moving forward with plans to build a bagasse-based n-butanol demonstration facility in Brazil alongside its partner Rhodia, a France-based specialty chemicals company owned by Solvay.

Rhodia and Cobalt started their collaboration in October last year. Following a demonstration plant, the companies said they plan to construct multiple biorefineries co-located with sugar mills initially in Brazil and then in other Latin American countries.

The companies did not disclose the location of the demo facility as well as capacity of the plant although according to Steven Shevick, chief financial officer of Cobalt in an email, the demo fermentor will be 1/10 the size of a commercial scale fermentor. According to Shevick, this is well within normal industry scale-up parameters.

According to Vincent Kamel, president of Rhodia Coatis Business unit (also via email), a commercial bio-butanol plant will produce up to 100,000 tonnes/year of the product. So if my math is correct....the demo facility will probably be around 10,000 tonnes/year.

Shevick said the companies are working with a top 5 sugar partner to install the demo facility near a sugar mill.

"Demo testing is expected to be completed no later than Q3 2013. The decision to build a commercial plant will be made in Q4 of 2013, and the plant would be running in time for the sugar harvest in the Spring 2015." - Shevick
Detailed cost estimates for the demo plant are also not disclosed but Shevick said they do not expect the cost to exceed $15m.

I wrote an article about this collaboration in December 2011 for ICB, and according to Rhodia back then, demand for butanol in Latin America is around 80,000 tonnes, and is forecasted to grow to 200,000 tonnes in 2015.

"The development of [the] bio-based n-butanol market is strategic to Rhodia's business growth ambitions in the region bearing in mind that the company now uses imported butanol to produce solvents such as butyl acetate. Rhodia plans to replace this imported butanol will bio-based n-butanol."
Shevick said its product price range could be between 40-60% below petroleum-based n-butanol depending on the feedstock. Cobalt Technologies' offering is the production of low-cost n-butanol using cellulosic biomass as feedstock.

In April 2011, Cobalt has partnered with US biorefinery technology firm American Process Inc. (API) to build a commercial-scale cellulosic biorefinery in Alpena, Michigan, US, which is expected to produce 470,000 gal/year of bio-based n-butanol by late 2012. The Alpena biorefinery is funded in part by an $18m US Department of Energy grant and a $4m grant from the State of Michigan.


UPDATE as of 8/10/12: The graphs used in this post came from Cathay Industrial Biotech Ltd.'s S-1 prospectus. Nexant was commissioned to do the market report for the prospectus.



Hello blog world! My apologies for the abrupt silence as the blogger did not have enough time to post an "Out of Office - I'm on a Marvelous Vacation" message. It's either posting or packing, and packing won hands down.

So coming back today and checking my 700+ emails, this news from Versalis, Novamont and Genomatica first caught my attention. In fact, I will have an interview with Genomatica CEO Christophe Schilling tomorrow morning.

The three companies announced on July 24 about their proposed partnership to produce biomass-based butadiene - a key raw material for the production of rubber.

Check my previous post for more on bio-based rubber developments.

Under the agreement, Versalis will use Genomatica's process technology to produce the bio-butadiene. One possible route to produce 1, 3 butadiene is the fermentation of sugars to 1,4 butanediol (which is what Genomatica has been developing) and then subsequent dehydration to butadiene.

Other possible routes also includes conversion of biobutanol to butenes and then to butadiene using the oxidative dehydrogenation process (remember Lanxess and Gevo's partnership?); and conversion of 2,3 butanediol to butadiene using a dehydration process (LanzaTech is looking at this as well with Synthos and Global Bioenergies).

Versalis, by the way, is a leading elastomers producer in Europe. According to Versalis, butadiene supply is increasingly becoming constrained and is subjected to availability problems.

"Decreasing supplies and a lack of dedicated butadiene production facilities have resulted in significant long-term pressure on the price and volatility of the chemical, which in turn increases the price of butadiene-based products, including tires. 
Concerns of scarcity in the butadiene market are compounded by growth forecasts within the BRIC countries where demand for automotive products made from butadiene, such as tires, is expected to increase."
Now if readers recall, Genomatica and Novamont already announced a previous joint venture deal in August 2011 to produce renewable-based butanediol (1,4 BDO) in a 40m lb/year plant in Italy starting late this year. 

The companies did not initially indicate where this plant is going to be located but then Novamont and Versalis also has a 50:50 joint venture called Matrica, which is planning to set up a EUR 500m biorefinery project in Versalis' Porto Torres complex in Sardinia, Italy.

So we put two and two together and could come up with a conclusion that Versalis and Novamont could produce the Genomatica-based butadiene as well as its feedstock BDO at Porto Torres. Whether that will be the 40m lb/year planned bio-BDO capacity or not is a question that the blog will ask Genomatica tomorrow.

The blog also does not know yet how much butadiene Versalis aims to produce and when they plan to start producing bio-butadiene.


Codexis announced today that it is under exclusive discussion with Shell that would give Codexis certain rights and licenses to develop and sell their cellulase enzymes to third parties in the biofuels field on a worldwide basis except Brazil.

Codexis said it has exclusive rights to commercialize its cellulase enzyme technology in all other fields (such as chemicals).

"Currently, Codexis' cellulase enzyme technology can only be commercialized in the advanced biofuels field through Shell and its affiliates. If we finalize a new agreement with Shell as we currently anticipate, the rest of the world's second generation biofuels producers will now also be available as target customers for our cost effective cellulase enzyme technology," said John Nicols, Codexis' President and Chief Executive Officer.
Shell can also elect to reduce between 13 and 48 full time employee equivalents under the Codexis-Shell research collaboration on one day notice beginning on August 31. The previous required notice for this redundancy was 90 days.

Codexis said it would take appropriate cost reduction measures to reduce its operating expenses if Shell will provide this notice to Codexis.


Panasonic, Nike in bio-resins

I thought at first that bio-propanediol (PDO) is now being used on television parts (is it?).

But according to this press release from DuPont Tate & Lyle Bio Products, Panasonic Corporation Eco Solutions Company (part of Panasonic Group) is instead using resins made from DuPont Tate & Lyle's Susterra bio-PDO for its line of kitchen and bathroom systems.

The compounded plant-based and petroleum-based resins are being used to manufacture Panasonic's kitchen countertops in the "Living Station" product line and the bathroom ceilings in the "Cococino" product line, which are being marketed in the Asia Pacific region.

The biobased materials also are being used for the wash basins and toilets in the Panasonic product line.

"We are delighted to be the first in the industry with a biobased commercialized product offering. This achievement contributes to Panasonic's sustainability goals as outlined in Green Plan 2018. The year 2018 is the 100th anniversary of the Panasonic Company," commented Kazumasa Rokushima, director of the General Technology & Products Development Center, Housing Systems Business Group at the Panasonic Eco Solutions Company.
Meanwhile, Nike announced last week that it will soon start selling its most environment-friendly Nike GS football boot on August 15. The Nike GS boot is constructed using combined renewable-based and recycled materials.

The Nike GS  sole plate is said to be made of 50% Pebax® Renew (a plant derived material made with 97% castor beans made French specialty chemical company Arkema) and 50% renewable-based thermoplastic polyurethane (TPU).

The boot laces, lining and tongue are made from a minimum of 70% recycled materials. The toeboard and collar, feature at least 15% recycled materials.



SDK starts bio-PBS sampling

The blog just noted in its last post about increasing activities from Japanese chemical companies, and in a happy coincidence, Showa Denko K.K. (SDK) just announced today that it has succeeded in producing its polybutylene succinate (PBS) resin under the trademark Bionolle using bio- based succinic acid.

PBS, a compostable polyester, is traditionally made from petrochemical-based succinic acid and 1,4 butanediol (BDO). The BDO part in SDK's Bionolle is probably still made from petrochemical feedstock. SDK's Bionolle Starcla is made from a combination of Bionolle (PBS) and starch.

Myriant is the company's bio-succinic acid supplier.

According to SDK, it has started providing the renewable-based Bionolle film-grade samples to customers such as Natur-Tec, a US-based bioplastic products manufacturer. Natur-Tec is already using petrochemical-based Bionolle for certain high-volume consumer goods packaging applications.

"Our customers are increasingly demanding higher biobased carbon content in our materials, in order to reduce the overall carbon footprint of their finished products. We are excited at the possibility of incorporating SDK's bio-derived Bionolle into our compounds and converted plastic products, to meet this burgeoning market demand." - Natur-Tec
SDK said it is planning to secure 10,000-20,000 tons/year of bio-based succinic acid to expand sales of its renewable-based Bionolle.

Another company already producing bio-based PBS (containing bio-succinic acid) is Japan-based Mitsubishi Chemical Company. The company estimated the PBS market worldwide at 5,000-6,000 tonnes/year, and is expected to grow to 50,000 tonnes/year in the next five years.


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