April 2012 Archives

The global automotive industry is abuzz with the tightened supply of polyamide 12 (also called nylon 12) which are used in cable ties, wire insulation, flexible hosing, nozzles, damping cogwheels, flexible cover caps, sheet gaskets, sealing rings, and in other fuel line applications/auto-related parts.

PA-12 is also used in plastic parts to make solar panels and cable coverings used in offshore oil and gas production.

Based on several googled websites, PA-12 reportedly have excellent properties such as high degree of dimensional stability under humidity or freezing environment; high resistance to chemicals such as hydraulic fluids, oil, fuels, grease, salt water, solvents; strong resistance to cracking under stress; high-resistance to abrasion; and has high fatigue resistance.

PA-12 also dampens noise and vibration, according to various sources. Unfortunately, I am not familiar with cars but from what I've seen on several news about this PA-12, this is an important chemical for the automobile industry as car makers and several players along the automotive supply chain held an emergency meeting yesterday in Detroit, Michigan, to discuss the critical issue on PA-12 shortage.

According to this article from Plastics News, there are very few suppliers worldwide of  PA-12, namely Evonik, Arkema, Ube Industries and EMS-Grivory. Global PA-12 production was estimated at around 100m lbs/year. Evonik is the only producer here vertically integrated in a key PA-12 feedstock called cyclododecatriene (CDT), which is manufactured by cyclotrimerization of butadiene.

CDT is used to make laurolactam, which in turn is used as a monomer in PA-12.

Unfortunately, a fire broke out at the end of March at Evonik's CDT facility in Marl, Germany, (two employees were killed) and CDT production (capacity is not disclosed) is expected to remain out-of-order for at least three months. This in turn, will affect PA-12 production for those who are dependent on CDT material.

Now here comes the castor part (sorry it took a while to get to this point...).

According to Evonik, the company is able to provide alternative substitutes to its CDT-based PA-12 products in the form of its VESTAMID Terra DD, which contains 45% renewable-based materials made from castor oil derivatives (mostly sebacic acid). The product is based on the polycondensation product of 1,10-decamethylene diamine and 1,12-dodecanedioic acid (this is where sebacic acid comes from).

VESTAMID Terra also comes as polyamide 6,10 which has a 63% biocontent -- the polycondensation of 1,6 hexamamethylene diamine and 1,10 decanedoic diacid (another sebacic acid material); and polyamide 10,10 - a 100% bio-based polymer from the polycondensation of 1,10 decamethylene diamine and 1,10 decanedoic diacid.

Evonik said it is possible to modify the biobased polymers to achieve much of the same material attributes as PA-12. In fact, the company announced yesterday that it has begun measures to increase production capacities of its VESTAMID Terra polymers at its Shanghai, China, plant.

An additional compounding facility for VESTAMID Terra will become operational in the third quarter of this year, and new capacity for the polymerization of the bio-based nylon are in the works and is scheduled to operate in the second half of 2013.

As the blog noted in previous posts about castor-based polyamides, Arkema has also been expanding its castor-based polyamides (under the RILSAN brand) -- when it acquired Hipro Polymers and Casda Biomaterials last year.

Other castor-based polyamides producers include Rhodia (Technyl eXten: PA-6,10) , BASF (Ultramid Balance: PA-6,10),  DSM (EcoPaXX: PA-4,10) and DuPont (Zytel PA-10 and PA-6,10). One thing to note is that Elevance is also targeting to produce natural oil-based derivatives such as diacids for PA-11 and PA-12 and is currently collaborating with companies like Arkema and DSM.

An interesting information about this PA-12 shortage is that other types of polyamides such as PA-6,12 and PA-6,10 could be an alternative to PA-12, according to producers who were interviewed* by ICIS colleagues at the recent plastic tradeshow NPE.

According to US plastic compounder A Schulman, PA-6,12 is a superior alternative to PA-12 for automotive applications given the same chemical resistance factors but PA-6,12 is said to have higher melting point. According to A Schulman, PA-12 supply has been increasingly tight even before the Evonik fire incident as demand from the oil and gas production has taken consumption share from the automotive supply chain.

More plastics are also being used in the automotive manufacture and therefore nylon-based materials are increasingly being used.

DuPont said* it is also working with auto makers to find alternatives for PA-12 in certain applications.

Rhodia, which produces PA-6,10 is reportedly* also working with customers to seek replacement for PA-12, while BASF -- a small CDT supplier as well, is offering its support to PA-12 producers.

Meanwhile, Evonik has also been in the middle of a planned PA-12 expansion, which was announced in December last year. Evonik said a 5,000 tonnes/year PA-12 expansion will supposedly start this year, and another 20,000 tonnes/year PA-12 expansion in its Asian facility is scheduled to be completed within 3 years.

*ICIS News subscription required

The BioBusiness Alliance of Minnesota (BBAM) recently released its Bio-industrial processing roadmap for the advanced biofuels and biobased chemicals industry to provide information for investors, businesses and stakeholders.

According to BBAM's projections, direct and indirect employment in bioindustrial processing companies in Minnesota could total in excess of 13,000 by 2025, up from 2,000 last year. Bioindustrial processing companies in the state include Segetis, BioAmber, XL Terra, Reluceo, Cargill Industrial Oils and Cargill BioH, Butamax, Gevo, NatureWorks, CHS, BioCee, Starch Tech, Natur-tec, EarthClean, Cortec, Lonza, Agristrand Biocomposites, Entropy Solution, Butrolix, and Jet-E.

Other key points the organization wants to put out is existing infrastructure needed for integrated biorefinery development as well as sufficient agricultural and forest resources available for biobased chemicals and advanced biofuels feedstock.

The report includes specific policy recommendations developed to support the development of bioindustrial processing. Of course, a major factor in establishing this type of industry is to ensure availability of funding options for companies interested in "putting roots" in Minnesota.

Financing will be of critical importance to the industry. A full spectrum of investment is needed, from seed and angel funding to venture capital and long-term debt capital. 

Tactics include:
• Educating investors and financial institutions about the unique opportunity to develop the bioindustrial processing industry in this region, and
• Ensuring awareness, availability, and access to federal and state financial support to accelerate research and development through full-scale manufacturing

It has been a looong time since I last posted any product introductions and this has been in my  draft box for far too long. I hope these product news are still useful to readers.

PLASTICS:

• Henkel - New additives for high-performance bioplastics

• Minerals Technologies Inc. Announces a New Product Line for Bioplastics Applications

• Cortec® Corporation Launches Biobased Film Products for Marine and Anaerobic Digestion Markets 

• Croda Coatings and Polymers - New green products

• Arkema Introduces Sustainable, Bio-Based Plexiglas® Acrylic Resin for Transparent Disposable Medical Devices

• Plexiglas Rnew Bio-based Acrylic Resins from Arkema Surpass Performance of Traditional PMMA Products

• Cereplast Introduces New Category of Bioplastics With First Ethylene-Vinyl Acetate (EVA) Starch Hybrid Resin

CHEMICAL ALTERNATIVES:

• BPA alternative: BASF offers a new solution for phenol-free thermal receipt paper

• Low VOC adhesives: 3M Introduces New Low VOC Spray Adhesives

• Water Membranes: Nalco Announces Breakthrough in Industrial Membrane Performance Management, 3D TRASAR® Technology

• Latex: BASF introduces STYROFAN® ECO 4810 latex - BASF

• Flame Retardants: Albemarle introduces next product in the Earthwise portfolio of sustainable, eco-friendly solutions

• Waxes: Sustainable Soy Wax Produced Using "Green Chemistry" Process - Dow Corning

• Coatings: Tennant Company Introduces Plant-Based, Sustainable Urethane Coatings to Protect and Add Durability to Floors

• Biofuel: Verenium Announces Launch of Purifine® PLC Enzyme for Use in Biodiesel Production -

Now that my sugar-based surfactant story on ICIS Chemical Business is out of the way -- that will be published and distributed next week at the ICIS World Surfactants Conference -- here is the blog's news roundup from last week. I also included bits of news that I just came across my email inbox from two weeks ago (sorry....)

GlyEco buys MMT Technologies
Glycol recycler GlyEco will acquire certain assets of Florida-based MMT Technologies, another glycol recycler. MMT, with 2011 revenues of $500,000, has over 1,000 customers from major car dealerships, quick lube facilities and independent repair shops. GlyEco said this is its third acquisition in the past 60 days. The transaction is expected to close on May 31. An estimated 177m gallons/year of recyclable antifreeze is disposed each year in the US, according to the Environmental Protection Agency (EPA).

Cardia Bioplastics wins US contract
Cardia Bioplastics has been awarded an annual supply contract worth at least $500,000/year from a leading American diaper products company for hygiene films made using Cardia Biohybrid technology. Cardia Bioplastics will supply the Cardia Biohybrid hygiene films from its Nanjing/China based film manufacturing plant.

Elevance's progress in catalyst tech
Elevance Renewable Sciences and metathesis catalysts developer XiMo AG have carried out successful demonstrations that make the Molybdenum-catalyzed metathesis of natural oil esters commercially competitive. Under the collaboration, which started in January 2011, the researchers tested more than 40 catalysts using several natural oil feedstocks under various conditions to evaluate their efficiency.

Cereplast launches first TPE-starch hybrid
Cereplast has introduced Hybrid 111D and Hybrid 112D thermoplastic elastomer (TPE) starch hybrid compounds for injection molding applications. Hybrid 111D boasts 30% starch and Hybrid 112D has 50% starch.End markets include soft grip applications such as handles for bicycles and tools, cosmetics packaging, housewares, household appliances, footwear and automotive applications. Cereplast also plans to introduce polyethylene hybrids in the next few months.

Vertellus picks castor distributors
Vertellus Specialties Inc. a manufacturer of castor oil, castor oil polyols and derivatives, has chosen McCullough & Associates Distributors as its authorized distributor in Virginia, North Carolina, South Carolina, Georgia, Alabama, Mississippi, and Tennessee. Vertellus also picked the Horn Company to be its authorized distributor in Texas, Louisiana, Arkansas, and Oklahoma.

Dow expands solar shingle markets
Dow Chemical expanded the availability of its Dow Powerhouse Solar shingle to San Antonio and Austin in Texas and to homeowners in northern California. Authorized dealers in the Texas area includes Beldon Roofing Company, Quality Roofing, and Ja-Mar Roofing. In California, new authorized dealers include Town & Country Roofing and Dority Roofing.

And in ICIS News (requires subscription):
News from the recent NPE tradeshow in Orlando:

Heavy trucks to start using recycled materials - SABIC

Braskem in bid to be world leader in sustainable chemistry

Bioplastics to reach polymer equivalence soon - BASF

More PET scrap stays in the US for recycling

Small musings from Sam Nejame on the recent Advanced Biofuels Leadership Conference held in Washington D.C. last week. Sam Nejame is a management consultant to the biofuel and renewable chemical industries.

------------------------------------
Despite ongoing political and economic challenges, the mood of attendees at the Advanced Biofuels Leadership Conference last week in Washington DC was one of guarded optimism... with the largest outstanding issue (beyond financing) the continuing search for economically viable cellulosic sugars.

Things seen and heard or should have known in no particular order ...

• Waste Management says every Fortune 200 company has a "Zero Landfill" strategy. Good for recycling, good for groundwater. Not so good if you sell landfill space. Hence investments in Fulcrum BioEnergy among others.

• SynGest says the United States' largest trade imbalance is not in oil, it's in fertilizer. The maker of "Bio-Ammonia" goes upstream to produce the "feedstock of feedstocks."

• Proterro makes sucrose via cyanobacteria trickling filter. Really? Wow. Take that sugarcane!

• Chromatin is making farnesene in plants. Terpenes in plants? Shouldn't they be making Taxol?

• Jefferies and Co. analyst, Laurence Alexander noted a dry spring will likely bring continued drought and a down year for corn production. "You can see it coming." Ouch.

• Virdia, the cellulosic sugar company, claims they are cost competitive with corn at $4/bushel.

• A panel of industry trade groups bemoaned the slow pace of cellulosic fuel development and worried it might threaten the whole RFS mandate. A point echoed by US Secretary of Agriculture, Tom Vilsack.

I just realized today that my phone has not been working since March 27. As I have been traveling for most of the past two weeks, I did not notice that my phone has not been ringing and I did not get indications of any voicemail until a colleague from the UK alerted me to this problem.

Thank goodness I only had 11 voicemails to go through!

But I'm betting this annoyance is not as big as the frustrations of several green chemistry researchers this week when they found out that grants they're looking forward to applying from the US Environmental Protection Agency (EPA) have just been canceled - with no explanation whatsoever.

According to a special announcement put up yesterday in the EPA website, the EPA cancelled grant applications for what was supposed to be a $20m, four-year green chemistry program. The solicitations include creation of "Centers for Material Life Cycle Safety" and "Centers for Sustainable Molecular Design," which were part of the EPA's Science to Achieve Results (STAR) program.

Environmental Health News has been following these grants since they were announced in December last year.

The EPA said the solicitations are currently being reviewed and may be reissued when the reviews are complete. According to @EPAResearch tweets today:

"While the RFAs (blogger note: I'm assuming this stands for Research Funding Assistance) for Ctrs for Material Life Cycle Safety and Ctrs for Sustainable Molecular Design solicitations have been cancelled..."

"Given the new and emerging research areas in the RFAs we determined it was necessary to further explore these research areas."

"We will be reissuing the #greenchemistry RFAs in Summer 2012," says EPA's Administrative Asst. Lek Kadeli.

"We appreciate the interest in these #greenchemistry solicitations and apologize for any inconvenience."

"Sign up for EPA research grant listserv and get notice of EPA research RFAs incl. #greenchemistry when reissued in Summer. http://www.epa.gov/ncer/listserv/"

Press releases of the back and forth bio-butanol patent lawsuits between Gevo and Butamax since March have piled up in the blog's inbox, and more statements just came out yesterday, April 10.

According to Gevo, the US Patent and Trademark Office (PTO) has granted the company patent number 8,153,415 entitled "Reduced By-Product Accumulation for Improved Production of Isobutanol." The '415 patent covers technology which eliminates two pathways that compete for isobutanol pathway intermediates in yeast meaning that it creates a more efficient isobutanol-producing yeast.

In association with the newly granted patent. Gevo then filed a lawsuit against Butamax and its affiliate DuPont, stating that Butamax has been using the related technology covered by their '415 patent to be able to reach commercial-scale production.

You can read what Butamax has to say about this latest lawsuit in this link.

Here are some of the back and forth "amicable" press releases the two companies produced last month against each other.

MARCH 6, 2012: 
From Butamax:
Butamax Expands Robust Isobutanol Patent Portfolio - US PTO has granted Butamax patent #8,129,162 covering KARI enzymes that optimize production of biobutanol by Butamax's proprietary microorganisms.

From Gevo:
USPTO Rejects Butamax's Self-Described "Foundational" IP Claims in Successful Gevo Reexamination Petition - US PTO rejected Butamax's patent claims under 7,851,188 currently being asserted against Gevo.

MARCH 7, 2012:
From Butamax:
USPTO Director Issues Final Decision Denying Gevo Reexamination Petition; Second Request fir Reexamination Granted in Error - US PTO Denies Gevo's petition to examine Butamax's 7,851,188 patent. The order is final and not appealable. Butamax is also seeking clarification on why the US PTO should consider Gevo's second re-exam request on some of the claims of the '188 patent.

MARCH 12, 2012:
From Butamax:
Butamax Files Biobutanol Patent Infringement lawsuit to Stop Gevo's use of Butamax
KARI Enzyme Technology - Butamax filed a new lawsuit against Gevo for infringing the Butamax patent 8,129,162 awarded on March 6.

From Gevo:
Gevo Refutes Butamax's Unfounded Allegations of KARI Enzyme Patent Infringement - self explanatory ;-)

MARCH 13, 2012:
From Gevo:
Gevo Granted Key Patent Covering Critical Technology to Enable Commercially Viable Yields of Isobutanol Production from Yeast - The US PTO has awarded Gevo patent no. 8,133,715 entitled "Reduced By-Product Accumulation for Improved Production of Isobutanol," covering technology that eliminate pathways that "hijack" carbohydrates, which reportedly lowers yield and creates unwanted by-products. Eliminating this pathway improves isobutanol yield by 20%.

In conjunction, Gevo filed a lawsuit against Butamax/DuPont charging the companies infringement against the newly issued patent.

From Butamax:
Butamax Responds to Gevo patent infringement lawsuit; Gevo patent dominated by Butamax patent - Butamax says the allegation has no legitimate basis.

After this was the latest one on April 10. I'm guessing the real winners here will be the companies' lawyers.

To apply, the business plan must focus on providing solutions in the following industry segments:

• Renewable Products
• Chemical Building Blocks
• Clean Energy
• Catalysis/Biocatalysis
• Pharmaceuticals
• Sustainable Construction Materials

More information about the contest in the ACS Green Chemistry website. Final date of submission and round 1 judging will be on April 30 at 5pm EST. The Business Plan competition finale will take place on June 19, 2012 from 10a-12:20p EST.

Good luck!

The blog is accumulating a lot of biofuel news for the past month.

Last week, the US Environmental Protection Agency (EPA) approved the first application submitted  for registration of E15 ethanol (a blend of 15% ethanol and 85% gasoline). Registration is a prerequisite to introducing E15 into the marketplace.

Biofuel advocates are currently pushing for E15, which if approved by the EPA, would allow producers to expand production to keep pace with the Renewable Fuel Standard's (RFS) 15bn gal/year cap on ethanol derived from corn starch.

E10 (a blend of 10 percent ethanol and 90 percent gasoline), which is currently distributed at the majority of gas stations in the continental U.S., is fast approaching a "blend wall," in which production exceeds the volume of fuel that can legally be blended into the U.S. gasoline market.

Before E15 can be sold, however, manufacturers must first take additional measures to help ensure retail stations and other gasoline distributors understand and implement labelling rules and other E15-related requirements, the EPA said.

ICIS colleagues who attended the American Fuel & Petrochemicals (AFPM) event in San Antonio, Texas, last week, tried to get some reactions on this recent news. According to one ethanol broker, the E15 approval will unlikely increase demand for the biofuel because of concerns about liability.

One liability is that drivers could mistakenly put the E15 fuel in automobiles made before 2001 and service stations could be potentially liable if those automobiles are damaged. E15 is not permitted for use in motor vehicles built before 2001 model year and in off-road vehicles and equipment such as boats and lawn and garden equipment.

In addition, relatively few service stations can handle the E15 blends making it unlikely that they will purchase the fuel, the broker said.

The AFPM association, meanwhile, noted at the conference that the EPA decision is "irresponsible" claiming E15 blend could "endanger the safety of US consumers and severely damage vehicles and gasoline-powered equipment."

With gasoline at around $4/gal, the ethanol industry claims the need for more affordable alternatives to foreign oil. The Renewable Fuels Association also released its "E15 Retailer Handbook" to provide fuel retailers with regulatory and technical guidance in order to legally store and sell E15 ethanol blends.

According to Pike Research's latest report Biofuels Markets and Technologies, U.S. ethanol production in 2011 reached 13.6bn gal/year (BGY), up from 13.2 BGY in 2010.

Another consulting firm, Clean Edge Inc., estimated global biofuels production and wholesale pricing of ethanol and biodiesel reached a record $83bn in 2011, up from $56.4bn the prior year. The increase was mostly due to a rise in ethanol and biodiesel prices, the result of higher costs for feedstock commodities - mainly sugar for ethanol and rapeseed and other vegetable oils for biodiesel.

In the meantime, here are more big biofuel news piled up in the blog's inbox:

• Virent and Virdia (formerly HCL CleanTech) successfully converted cellulosic pine tree sugars to drop-in hydrocarbon fuels within the BIRD Energy project, a joint program funded by the US Department of Energy, the Israeli Ministry of National Infrastructure and the BIRD Foundation.


• Neste Oil joins aireg, Aviation Initiative for Renewable Energy in Germany, which promotes the development and deployment of biofuels in Aviation. Neste Oil also said that it has quadrupled its use of certified raw materials in terms of tonnage in producing its renewable diesel in 2011. Neste Oil aims to increase its usage of certified raw materials a further 10 percentage points on the 2011 figure during 2012.


• Mascoma and Lallemand Ethanol Technology have entered into a commercial agreement with Pacific Ethanol Columbia for the use of MGT Grain Technology (MGT) yeast in Pacific Ethanol's 40m gal/year facility. The MGT product is a bioengineered drop-in substitute for conventional fermenting yeast that lowers costs for corn ethanol producers
  


• The Naval Air Warfare Center Weapons Division in China Lake, Calif., has awarded a manufacturing contract to specialty chemical firm and catalyst supplier Albemarle to complete its first biojet fuel production run based on biobased n-butanol provided by Cobalt Technologies. For this production run, Albemarle will utilize NAWCWD alcohol-to-jet (ATJ) fuel technology to convert Cobalt's biobased n-butanol into biojet fuel at its Baton Rouge, La., processing facility.


• Celanese has received key government approvals necessary to proceed with its previously announced plans to modify and enhance its existing integrated acetyl facility in China at the Nanjing Chemical Industrial Park to produce ethanol for industrial uses. The unit, based on Celanese TCX® ethanol process technology, is expected to startup in mid-2013.
  


• Mendel Biotechnology and BP Biofuels have signed a four-year agreement to conduct a demonstration field trial of Mendel's PowerCane™ Miscanthus and evaluate its performance as feedstock for biofuel production at BP Biofuels' demonstration plant at Jennings, Louisiana. A total of 100 acres of PowerCane™ Miscanthus will be planted in early 2012 near BP's Jennings facility and the first biomass harvest from these fields is expected in 2013.
  


• Cool Planet Biofuels announced its use of REPREVE® Renewables' FREEDOM™ giant miscanthus to manufacture tank-ready gasoline. REPREVE Renewables provided feedstock to Cool Planet Biofuels for testing in its process. Cool Planet reported that they were able to achieve a 4,000 gallons/acre conversion rate, which the company said outperforms other feedstocks such as corn, switchgrass and wood on yield.
  

Yes, it's been a week since I last blog and I definitely needed the time off as school is killing me. Fortunately, this week is a spring break so hopefully I'll be more productive. We'll start with our (semi-monthly) news round-up...

EcoSynthetix commissions new plant
Canada-based EcoSynthetix has commissioned a new 80m lb/year production line within its existing US manufacturing facility in Tennessee bringing its annualized capacity to 235m pounds. The company produces biomaterials such as starch-derived latex binders and monomers for adhesives and resins. EcoSynthetix said their EcoSphere biolatex polymer can be a drop-in replacement for styrene butadiene and styrene acrylic latex with their current equipment and processes.

Solazyme, Bunge forms Brazil JV
Solazyme and Bunge have formed a joint venture to build, own and operate a commercial-scale renewable tailored oils production facility adjacent to Bunge's Moema sugarcane mill in Brazil. The JV, which will operate under the name Solazyme Bunge Produtos Renováveis Ltda., will have an expected annual production capacity of 100,000 metric tons of oil. The facility will utilize Solazyme's renewable tailored oil production technology, coupled with Bunge's sugarcane supply and processing capabilities, to produce sustainable tailored triglyceride oils for use in oleochemical and fuel applications in the Brazilian domestic market.

Technip, CIMV in green chem partnership
Engineering firm Technip has partnered with Compagnie Industrielle de la Matiere Vegetable (CIMV) to commercialized CIMV's solid biomass-to-hydrocarbon process. Technip has established a sales force to promote the CIMV process outside France, along with the wide range of bio-sourced applications. The two companies have been working together for the past five years.

Maverick Biofuels, TopLine Energy partnership
Maverick Biofuels and TopLine Energy Systems (TES) formed a joint technology development initiative to integrate TES's PRISM ™ plasma reactor technology and Maverick's thermochemical process to produce fuels and bioplastics from biomass and waste feedstocks. The TES technology will produce an ultra clean, reaction grade synthesis gas which is then converted to a three to five chain carbon olefin intermediate using Maverick's thermochemical technology. The olefins are then processed into a variety of high-value products, including mixed-alcohol fuel, bio-plastics, and jet fuel.

BASF bioplastic project completed
The municipal waste management company Berliner Stadtreinigung (BSR) and BASF have successfully completed a joint pilot project involving the use of organic waste bags made of the biodegradable plastic Ecovio® FS. The plastic material is made of the partially bio-based plastic (polyester) Ecoflex® FS and PLA (polylactic acid).

And in ICIS News (requires subscription):
These are the articles I wrote coming from the Bioplastek conference.

US plastic converters seek bio-based polymers

Fracking industry seeks biodegradable polymers - Danimer

US Danimer to expand bioplastic plant with Myriant partnership

Biomass feedstock important in bioplastics future - Nexant

US-based Anellotech the lowest cost bio-paraxylene producer - Nexant