Archive for the ‘Biofuels & Biomaterials’ category

Don’t Mess With GS: GreenShift’s Ethanol Patent Enforcement Roadshow

May 17th, 2010

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In previous posts (here and here) I discussed GreenShift Corporation’s (GreenShift) patent suits against New Jersey-based separator and decanter maker  GEA Westfalia Separator, Inc. (Westfalia) and ethanol maker Cardinal Ethanol (“Cardinal”).

In both suits GreenShift accused the defendants of infringing U.S. Patent No. 7,601,858 (’858 Patent), entitled “Method of processing ethanol byproducts and related subsystems.”

GS CleanTech Corporation (GS), a wholly owned subsidiary of GreenShift, has recently turned up the heat on a host of ethanol producers, firing off complaints in courthouses across the midwestern United States.  The recent lawsuits include:

GS CleanTech Corp. v. Big River Resources Galva, LLC, filed February 12, 2010 in the Northern District of Illinois (gs-galva_complaint.pdf);

GS CleanTech Corp. v. Amaizing Energy Atlantic, LLC, filed May 3, 2010 in the Northern District of Iowa (gs-amaizing_complaint.pdf);

GS CleanTech Corp. v. Center Ethanol, LLC, filed May 3, 2010 in the Northern District of Illinois (gs-centerethanol_complaint.pdf);

GS CleanTech Corp. v. Bushmills Ethanol, Inc., filed May 3, 2010 in the District of Minnesota (gs-bushmills_complaint.pdf);

GS CleanTech Corp. v. United Wisconsin Grain Producers, LLC, filed May 3, 2010 in the Western District of Wisconsin (gs-wisconsin_complaint.pdf);

GS CleanTech Corp. v. Blue Flint Ethanol, LLC, filed May 3, 2010 in the District of North Dakota (gs-blueflint_complaint.pdf); and

GS CleanTech Corp. v. Iroquois Bio-Energy Company, filed May 3, 2010 in the Northern District of Indiana (gs-iroquois_complaint.pdf).

The ’858 Patent is directed to methods of recovering oil from byproducts of ethanol production using the process of dry milling, which creates a waste stream comprised of byproducts called whole stillage.

According to the ’858 Patent, whole stillage contains valuable oil but prior processes for recovering this oil have been expensive or inefficient.

GS’s patented method includes mechanically separating the whole stillage into distillers wet grains and thin stillage and then running the thin stillage into an evaporator to form a concentrated byproduct, or syrup.  The syrup is fed through a second centrifuge, which separates usable corn oil from the syrup.

By my count the complaints filed this month bring GS’s patent enforcement total to nine lawsuits, which suddenly makes this a major green patent story.  Stay tuned.

MOU Gives AIQ Option to License PetroAlgae’s Micro-Crop Technology in Chile

May 12th, 2010

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PetroAlgae is a Florida-based renewable energy company that licenses its technology for growing and harvesting “micro-crops” such as algae, diatoms, micro-angiosperms and cyanobacteria for large scale production of biofuels.

Last month PetroAlgae announced a deal with Chile’s Asesorias e Inversiones Quilicura (AIQ).  The memorandum of understanding signed by the parties provides AIQ with an option to purchase a license to build a full micro-crop technology system in Chile to produce green gasoline, diesel and jet fuel (see the Recharge News story here).

According to PetroAlgae’s technology description, its system has a “modular, flexible design construction” that enables “near-continuous” growth and harvesting of a wide variety of micro-crops.  The company uses ”proprietary methods of controlling nutrients and light exposure to produce unsurpassed per-acre yields of biomass and protein extracts.” 

The large quantities of biomass produced by the growth and harvesting technology can then be refined into transportation fuels.

PetroAlgae owns at least two international patent applications relating to its micro-crop technology.  International Patent Application No. PCT/US2007/006466 (’466 Application) is entitled “Systems and Methods for Large-Scale Production and Harvesting of Oil-Rich Algae” and is directed to systems and methods for continuous harvest of microorganisms on a large scale.

Disclosed systems include a central seed fermentation area with numerous final fermentation ponds emanating from the central seed fermentation area and arranged, for example, in a pie shape.  The final ponds can be of various shapes or dimensions to accommodate different ratios of seed to final fermentation, different growth rates of organisms, etc.

According to the ’466 Application, wedge-shaped ponds are particularly well suited for growing photosynthetic organisms in continuous culture because media can be added near the point of the wedge and subsequently move toward the wide portion of the wedge, which allows greater surface area and sunlight for the multiplying cells.

With numerous pools, “the growth cycle can be offset between each pool such that there can always be at least one pool ready for harvest each day.”

International Patent Application No. PCT/US2007/020211 (’211 Application), entitled “Tubular Microbial Growth System,” is directed to continuous harvest methods using a bioreactor system for growing microorganisms. 

The ’211 Application describes numerous tubular growth units, or bioreactor pipes, that can each be seeded from a single “nursery” bioreactor.  The growth cycles can be offset so there is always at least one bioreactor pipe ready for harvest each day.

The bioreactor pipes can be coated to selectively pass and/or reflect specific wavelengths of light to regulate light exposure for the growing bugs.

The PetroAlgae-AIQ agreement is another example of a partnership to effect green technology transfer from developed countries to developing countries and emerging markets, despite claims that patents are a barrier to such transfer.

However, it appears this tech transfer deal so far has not been hindered by PetroAlgae’s IP.  We’ll see if AIQ exercises its licensing option.

Greenshift Seeks Quick Injunction Against Cardinal Ethanol

March 8th, 2010

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In a previous post, I wrote about GreenShift Corporation’s (GreenShift) patent suit against GEA Westfalia Separator, Inc. (Westfalia), in which GreenShift accused the New Jersey-based separator and decanter maker of infringing U.S. Patent No. 7,601,858 (’858 Patent).

Last month GreenShift asserted the ’858 Patent again, alleging that Indiana ethanol maker Cardinal Ethanol (“Cardinal”) is infringing the patent by using equipment that employs the patented ethanol processing methods.  The suit was filed in federal court in Indianapolis.

The ’858 Patent is entitled “Method of processing ethanol byproducts and related subsystems” and is directed to methods of recovering oil from byproducts of ethanol production. 

Ethanol production by dry milling creates a waste stream comprised of byproducts called whole stillage.  According to the ’858 Patent, whole stillage contains valuable oil but prior processes for recovering this oil have been expensive or inefficient.

GreenShift’s patented methods include mechanically separating the whole stillage into distillers wet grains and thin stillage and then running the thin stillage into an evaporator to form a concentrated byproduct, or syrup.  The syrup is fed through a second centrifuge, which separates usable corn oil from the syrup.

Along with the complaint, GreenShift filed a motion for preliminary injunction (PI), in which it argued that it has a strong likelihood of proving infringement, the ’858 Patent is valid, and it would suffer irreparable harm if Cardinal is not enjoined (see packet including GreenShift’s press release, the complaint and the PI motion here).

The PI motion includes a detailed claim chart that seeks to demonstrate Cardinal’s alleged infringement of claims 8, 10, 12, 13, 14 and 16 of the ’858 Patent. 

As to the alleged harm, GreenShift states that Cardinal’s infringement is causing it to suffer “loss of market share, opportunities, revenue and goodwill” as well as damage to its “reputation as a technology pioneer.”

Cornell Spin Out Catalyzes CO2-Based Plastic Wrap

January 3rd, 2010

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Novomer, Inc. (Novomer) is a Cornell University spin out that makes green plastics, polymers and other chemicals from carbon dioxide and other renewable raw materials. 

Novomer uses catalysis systems invented by Cornell professor Geoffrey Coates, and patented by the university, to make various polymers.  One of the company’s primary products is polypropylene carbonate (PPC), known as NB-180, which consists of 50% fossil fuels and 50% carbon dioxide.

Through Coates’s chemical catalysis, epoxides (fossil fuel materials) can be reacted with carbon monoxide or carbon dioxide at low temperatures and pressures to produce high performance polymers that provide better barriers for storing food and decompose into environmentally benign products, according to the company’s web site.

U.S. Patent No. 6,133,402 (’402 Patent) relates to zinc- and other metal-based catalysts for co-polymerization of alkylene oxides and carbon dioxide.  U.S. Patent No. 7,304,172 (’172 Patent) is directed to cobalt catalysts, various co-catalysts and reversible chain transfer agents for use with cobalt catalysts for co-polymerization of propylene oxide and carbon dioxide. 

The ’172 Patent claims a few different catalysts, including a cobalt catalyst having the following general structure:

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Novomer also owns International Patent Application Pub. No. WO 2009/148889 (’889 Application), which published last month and is directed to methods of controlling the molecular weight distribution of polymers made by addition polymerization reactions.  The ’889 Application incorporates by reference the ’402 and ’172 Patents and some of Coates’s scientific publications.

Novomer recently partnered with Kodak to build a pilot production facility to make plastic wraps and coatings for testing by prospective customers.  According to this Greentech Media story, because of the huge amounts of oil that go into plastics manufacturing, if Novomer’s process were to go universal U.S. fuel consumption could drop by 5%.

Biofilm, Bugs and Bioreactors: The IP Behind Coskata’s New Biofuel Facility

November 8th, 2009

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In a previous post, I wrote about Coskata’s patent-pending ethanol production process.  The Illinois-based cellulosic ethanol company’s proprietary technology makes ethanol from various feedstocks by converting it to synthesis gas, or syngas, and then fermenting the gas using anaerobic microorganisms.

Coskata owns Patent Application Publication Nos. 2008/0305539 and 2008/0305540, directed to a membrane supported bioreactor system for converting syngas to biofuels (collectively “Bioreactor Applications”). 

According to the Bioreactor Applications, the disclosed processes boost efficiency by using one side of a membrane as the syngas contact surface and the opposite side as the surface for growing the microorganisms.  The gas is fed onto the contact side and transported through the membrane to a biofilm of anaerobic microorganisms, where it is fermented into biofuels.

Last month, Coskata opened a semi-commercial ethanol facility in Madison, Pennsylvania that makes ethanol using the company’s microorganisms and bioreactor technology.  According to the company’s press release, the flex facility will produce ethanol from numerous feedstocks, including wood biomass, agricultural waste, sustainable energy crops and construction waste.

To build the facility, Coskata teamed up with Westinghouse Plasma Corporation, which suppled the gasification technology for the project.

I had the opportunity to speak to Wes Bolsen, Coskata’s CMO, about the new facility, the company’s technology and the company’s IP.  He confirmed that the Pennsylvania facility uses Coskata’s patent-pending bioreactor technology.

Bolsen also told me that Coskata has patents directed to microorganisms used in the fermentation process, but that the company favors trade secret protection for some of the newer strains of “bugs,” including some of those used in the new facility.

According to Bolsen, Coskata ”will continue with patents, trade secrets and whatever combination of the two” the company needs.  “Our IP is the core of this business,” he said.  ”Our IP and innovation is what keeps us ahead in the industry.”

GreenShift-ing Focus to Pre-Grant Damages in Ethanol Processing Patent Suit

November 5th, 2009

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GS CleanTech Corporation (GS), a wholly owned subsidiary of GreenShift Corporation, is a New York company that develops technology relating to energy efficient ethanol production processes.

GS owns U.S. Patent No. 7,601,858 (’858 Patent), entitled “Method of processing ethanol byproducts and related subsystems” and directed to methods of recovering oil from byproducts of ethanol production.

Dry milling is a popular method of producing ethanol by fermentation of the starch in corn or other grains.  However, this method creates a waste stream comprised of byproducts called whole stillage.

According to the ’858 Patent, whole stillage contains valuable oil but prior processes for recovering this oil have been expensive or inefficient.

GS’s patented method includes mechanically separating the whole stillage into distillers wet grains and thin stillage and then running the thin stillage into an evaporator to form a concentrated byproduct, or syrup.  The syrup is fed through a second centrifuge, which separates usable corn oil from the syrup.

The ’858 Patent issued on October 13, 2009.  The same day, GS filed suit in federal court in Manhattan accusing New Jersey-based separator and decanter maker GEA Westfalia Separator, Inc. (Westfalia) and multiple as yet unnamed defendants of contributory infringement and inducing infringement of the ’858 Patent. 

According to the complaint (greenshift-complaint.pdf), Westfalia sells centrifuges for corn oil extraction and directs its customers to use the methods taught in the ’858 Patent.

Because the suit was filed upon patent issuance, GS’s recoverable damages are quite limited.  So GS is claiming provisional patent rights under Section 154(d) of the patent statute, which allows recovery of a reasonable royalty if the infringer had actual notice of the published patent application and the claims of the issued patent are substantially identical to the originally published claims.

This strategy demonstrates the importance of promptly notifying any potential infringers as soon as your patent application publishes, which is 18 months after filing in the U.S.

Thanks again to the Cleantech Litigation blog for the head’s up about this case.

ExxonMobil Partners with Synthetic Genomics to Develop Algal Biofuels

August 6th, 2009

Synthetic Genomics, Inc. (SGI) is a San Diego biotech company that develops biofuels using genetic engineering and other genomic and microbiological techniques.

Last month SGI announced that it has entered a multi-year research and development agreement with ExxonMobil Research and Engineering Company (EMRE) to develop next generation biofuels using photosynthetic algae. According to SGI’s press release, total funding for R & D and milestone payments could total more than $300 million. 

SGI will use its proprietary tools and technologies in genomics, metagenomics, synthetic genomics and genome engineering to develop superior strains of algae for commercial scale production of biofuels.  SGI owns several pending patent applications relating to these tools and technologies. 

U.S. Application No. 2007/0264688 (’688 application) is entitled “Synthetic genomes” and is directed to methods of constructing synthetic genomes and introducing them into vesicles (cells or synthetic membrane-bound “cells”). 

The ’688 application describes generating small nucleic acid fragments, assembling them into cassettes, cloning the cassettes, assembling the cassettes into a genome, and transferring the synthetic genome into a biochemical system.  The end products produced by the biochemical systems have various applications such as energy sources (e.g., hydrogen or ethanol), therapeutics and industrial polymers.

According to the ’688 application, selection and construction of synthetic genome sequences (as opposed to conventional genetic engineering techniques) allows for easier manipulation of genetic sequences and construction of novel organisms and biological systems.

U.S. Application No. 2007/0269862 (’862 application) is directed to methods for installing a genome into a cell or cell-like system.  The genome may comprise supercoiled nucleic acid molecules (102) with scaffolding proteins (104).  The nucleic acids may also have ribosomes (106).

The supercoiled nucleic acid molecules (102) may be accompanied by small molecules (108) and single stranded nucleic acid molecules (110).  The genomes are introduced into a membrane bound aqueous volume (112) such as a lipid vesicle.

Claim 1 of the ’862 application is rather broad:

1.  A method for making a synthetic cell, the method comprising:

obtaining a genome that is not within a cell; and

introducing the genome into a cell or cell-like system.

U.S. Application No. 2009/0176280 is directed to a method for isothermal amplification of small amounts of DNA or cell-free cloning of the DNA.

Other SGI pending applications include U.S. Application Pub. No. 2007/0037196 and U.S. Application Pub. No. 2007/0037197 (relating to in vitro methods for joining two double-stranded DNA molecules) and U.S. Application No. 2007/0122826 (relating to a minimal essential gene set that codes for a free-living organism).

One theme that runs throughout SGI’s portfolio of patent applications is impatience with the limits of existing genetic engineering methods and a desire for better techniques to shatter those limits, which SGI may have found in its synthetic genome technology.  This “Description of the Related Art” from the ’688 application captures that sentiment:

Conventional genetic engineering techniques are limited to allowing manipulation of existing sequences.  It would thus be desirable to have the ability to implement dramatic alterations and arrangements of genetic content, beyond that made possible by conventional techniques.  Consequently, there is a need for synthetic genomes.

Green Patent Acquisitions: Rentech Buys SilvaGas Gasification Technologies

August 4th, 2009

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Rentech, Inc. (Rentech) is a Los Angeles company that provides clean energy solutions including biomass gasification technology and processes for converting synthetic gas (syngas) into synthetic jet fuel and diesel fuels.

Last month Rentech announced that it had completed the acquisition of Atlanta-based SilvaGas Corporation (SilvaGas) and SilvaGas’s commercial-scale biomass gasification technology, which converts urban waste feedstocks into syngas.

According to the press release, the acquisition will enable Rentech to offer integrated packages for renewable fuels and power production by combining the SilvaGas gasification technology with Rentech’s syngas conversion, conditioning and cleanup technology.

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The SilvaGas patent portfolio includes several patents and pending applications relating to high-throughput gasifier technology.  The original SilvaGas process was protected by U.S. Patent No. 4,828,581 (’581 patent), entitled “Low input gas velocity high throughput biomass gasifier”.  The ’581 patent expired in 2006.

The ’581 patent describes a process of rapidly heating biomass with hot sand using a reactor that has a fluid bed of sand.  According to the ’581 patent:

This invention comprises the unexpected discovery that it is possible to gasify biomass at very high wood throughputs but in an entrained gasifier operating at low inlet gas velocities.

Entrained gasifiers perform gasification reactions in a cloud of fine particles, which can be solids, atomized liquid fuels or fuel slurries.

Another key SilvaGas patent is U.S. Patent No. 6,613,111 (’111 patent), entitled “Small scale high throughput biomass gasification system and method”.  The ’111 patent is directed to a high-throughput combination gasifier and combustor wherein the gasifier is concentrically housed within the combustor. 

The gasifier system includes a gasifier (102) and a combustor (118).  The combustor (118) acts as a source of heat to drive the gasification reactions in the gasifier (102).  The gasifier (102) and combustor (118) transfer heat and materials to each other via circulation of a particulate inert material, such as sand, which is fluidized by gas flowing through the material. 

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A fluidizing gas inlet (110) provides a flow of gas into the gasifier (102), and gas exits the gasifier at exit (112), flows through a separator (114), and exits as product gas through product gas exit (116).  Biomass feedstock is introduced through the entry opening (106), and the particulate material travels from the combustor (118) into the gasifier (102) through a recirculation opening (108).

According to the ’111 patent, the arrangement of the gasifier (102) concentrically within the combustor (102) minimizes heat loss from the surface of the gasifier and improves the efficiency of the system.  This helps to make the patented system suitable for small scale gasification having a relatively low feedstock input rate.

Most of the other SilvaGas patents and applications are directed to improvements or variations of these core technologies, including U.S. Patent No. 6,808,543 (methods for reducing ash agglomeration, reducing erosion and facilitating sand flow), U.S. Patent No. 6,680,137 (an energy system connecting a gasifier and a combustor to a fuel cell) and U.S. Application Pub. No. 2008/0022592 (a more efficient gasification system having certain diameter and height specs).

OriginOil Provides Full Service Algae Support

June 11th, 2009

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OriginOil, Inc. (OriginOil) is a Los Angeles company developing a full range of technologies to improve the processes of algae growth and oil extraction.  OriginOil’s methods may substantially reduce the amount of energy necessary to extract oil from algae (see the Matter Network story here).

Unlike some algae biodiesel companies who only focus on the extraction step, OriginOil’s innovations span a much broader approach.  The company’s suite of technologies is covered by several pending patent applications, which “apply to the whole life cycle of algae production, not just extraction” according to OriginOil’s President and CEO Riggs Eckelberry. 

OriginOil’s U.S. Patent Application Pub. No. 2009/0029445 (’445 application), is entitled “Algae growth system for oil production” and is directed to systems for growth and processing of microorganisms such as micro-algae. 

The systems attempt to duplicate the optimum natural growth promoting environment for algae, including thorough exposure to carbon dioxide, growth promoting admixtures, exposure to light and extraction.

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The key to this Quantum Fracturing process is breaking down water, carbon dioxide and other nutrients into micron-sized bubbles.  The increased surface area of these bubbles facilitates high absorption of carbon dioxide and nutrients by micro-algae during the growth phase.

Several as yet unpublished patent applications are directed to other aspects of OriginOil’s algae technology, including:

an application filed in 2008 directed to the Helix Bioreactor, which optimizes delivery of light to algae by providing light at closely spaced intervals within a photobioreactor;

an application filed in 2008 directed to the company’s Modular and Scalable Growth System, which facilitates large scale algae production through stacking of multiple Helix Bioreactors into an integrated network; and

an application filed this year directed to a Single-step Extraction Process, which combines Quantum Fracturing with electromagnetics and pH modification to break down cell walls and extract oil in one step.

OriginOil recently announced the filing of an international or PCT patent application, which Mr. Eckelberry said combines several of the company’s technologies and is now its consolidated “lead application” going forward. 

With this holistic approach, Eckelberry said OriginOil’s business model is to help other companies make algae and provide full support for its customers producing the oil.  The company’s new partnerships include one with Desmet Ballestra and one with the U.S. Department of Energy’s Idaho National Laboratory, wherein the latter will team with OriginOil on algae scalability issues.

Metabolix Bioplastics Are Cleanly Made and Biodegrade

June 4th, 2009

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Metabolix is a Massachusetts biotech company that makes alternatives to petrochemical-based plastics. 

Metabolix’s bioplastic technology includes polymers known as polyhydroxyalkanoates (PHA) and enzymes that make these polymers.

According to this Seeking Alpha article, PHA are “linear polyesters produced in nature by bacterial fermentation of sugar and lipids.”  In other words, PHA are made by microoorganisms through photosynthesis.

CleanTechnica reports that Metabolix is working with the Strategic Environmental Research and Development Program to develop its bioplastic for military use in food packaging.

The company also formed a joint venture with Archer Daniels Midland called Telles to market its bioplastic, which it sells under the brand name Mirel.

Some of Metabolix’s key patents and applications include U.S. Patent Nos. 6,620,869 (’869 patent), 7,202,064 (’064 patent), 7,208,535 (’535 patent) and U.S. Patent Application Pub. No. 2008/0275208 (’208 application), which are directed to PHA biopolymer compositions.

These inventions include improved thin film formation through PHA pellet compositions (’869 patent and ’535 patent) and methods of making PHA compositions that can be readily extended to incorporate additional monomers by mutagenesis or genetic engineering of PHA-producing microorganisms (’064 patent and ’208 application).

Metabolix recently announced that its Mirel bioplastic resins have received the OK Compost Home certification (provided by Belgian inspection and certification firm Vincotte), which means that the materials will biodegrade in home composting systems of varying temperatures. 

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Its materials previously received the OK Compost certification for industrial composting.  (read about the Vincotte OK Compost certifications: vincotte_cb_05.pdf

Unfortunately, Mirel bioplastics are not yet cost competitive with plastics made from petroleum (Mirel sells at $1.50 per pound versus 70 cents per pound for traditional plastics), but the company believes that many customers will pay a premium for its cleanly made, compostable materials, especially in the disposable plastics market.