Archive for the ‘Biofuels & Biomaterials’ category

Novozymes Ethanol Enzyme Patent (Barely) Survives Summary Judgment

March 7th, 2011

In a previous post, I wrote about a patent infringement suit between Danish biopharm rivals Novozymes and Danisco, which are both active in developing enzymes used in production of biofuels.

In the suit, Novozymes has accused Danisco of infringing U.S. Patent No. 7,713,723 (’723 Patent) by selling alpha amylase enzymes including Danisco’s GC358 product.  See the complaint here: novozymes_complaint.pdf.

The ’723 Patent is entitled “Alpha amylase mutants with altered properties” and relates to variants of certain alpha amylases that exhibit altered stability under high temperatures, low pH and other conditions.  The patented variants can be used for starch conversion in ethanol production.

Last month Judge Barbara B. Crabb of the U.S. District Court for the Western District of Wisconsin denied Danisco’s motion for summary judgment of invalidity of the ’723 Patent. 

In the Opinion (Novozymes-Order), Judge Crabb rejected Danisco’s argument that the patent is invalid for insufficient written description. 

A U.S. patent must have an adequate written description to be valid.  This means the patent’s specification (which includes the description and figures, but not the claims) must convey to a person skilled in the relevant technical field that the inventor actually invented and “had possession” of the claimed invention.

Danisco argued that the ’723 Patent – directed to a substitution of an amino acid at position 239 in the alpha-amylase protein - was inadequate because the written description lists position 239 as one of 33 possible positions for an “alteration” and lists a substitution as just one possible type of alteration.

According to Danisco, that extensive variability means the ’723 Patent identifies 8.589 x 1042 possibilities for experimentation to arrive at the claimed invention.

Despite “doubts” about the adequacy of the written description, Judge Crabb concluded that Danisco did not meet its burden of proving invalidity as a matter of law. 

The opinion notes that Novozymes put forth expert testimony and other evidence sufficient to create an issue of fact as to whether a person of skill in the art would interpret the specification of the ’723 Patent as disclosing that substitutions at each of the 33 positions would lead to improved stability of the alpha amylase.

The decision was a close one for Judge Crabb, who stated in the opinion ”[i]t is not without hesitation that I am denying defendants’ motion.”  This will be an interesting case to watch, and one that could go down to the wire.

BP-DuPont Biofuels JV Takes Gevo to Court

February 14th, 2011

Butamax Advanced Biofuels (Butamax) is a Delaware-based joint venture between BP and DuPont formed in 2009 to develop biobutanol. 

Biobutanol is an advanced biofuel which has some important advantages over ethanol, including an energy content closer to that of gasoline and the capacity to create higher blend concentrations with gasoline.

Butamax owns U.S. Patent No. 7,851,188, entitled “Fermentive production of four carbon alcohols” (’188 Patent).  The ’188 Patent is directed to Butamax’s biobutanol production technology and recombinant microbial host cells that produce the biofuel.

Last month Butamax sued Gevo, an Englewood, Colorado, advanced biofuels company, for infringement of the ’188 Patent.

The complaint (Butamax_Complaint), filed in federal court in Delaware, alleges that Gevo’s isobutanol production pathway infringes the ’188 Patent:

On information and belief, Gevo makes recombinant microbial host cells by engineering DNA constructs containing isobutanol pathway genes and integrating them into the cells.  These DNA constructs encode enzymes that catalyze conversion of 1) pyruvate to acetolactate; 2) acetolactate to 2,3-dihydroxyisovalerate; 3) 2,3-dihydroxyisovalerate to α-ketoisovalerate; and 4) α-ketoisovalerate to isobutyraldehyde.  These host cells produce isobutanol through this pathway.

According to the complaint, Gevo has produced isobutanol using such microbial host cells in a retrofitted ethanol production facility and is converting another ethanol facility for isobutanol production.

Butamax is seeking an injunction and monetary damages.

As far as I know, this is the first instance of biofuel patent litigation involving a major oil company.  With the oil majors increasingly involved in biofuels startups via research funding, buyouts, and JVs like Butamax, it won’t be the last.

High Tech Hydrocarbons: Neste Biodiesel Branches Out

December 8th, 2010

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Neste Oil (Neste) is a Finnish oil refining company that focuses on advanced, low-emission transportation fuels. 

Neste has the distinction of starting up the world’s largest biodiesel plant, which began production last month in Singapore.  The plant has an annual capacity of 800,000 tons and will produce biodiesel fuel using Neste’s NExBTL renewable diesel production technology.

Neste owns more than 30 international patent applications, including at least two directed to biodiesel production technology. 

International Publication No. WO 2007/068798 (’798 Publication) is entitled “Process for the manufacture of hydrocarbons” and is directed to processes for manufacturing branched saturated hydrocarbons that include a skeletal isomerisation step followed by a deoxygenation step.

According to the ’798 Publication, the process uses renewable sources, such as plant, vegetable, animal and fish fats and oils and fatty acids and first subjects them to skeletal isomerisation, which means forming branches in the fat molecule’s main carbon chain while maintaining the same number of carbon atoms.

Then the branched hydrocarbons are deoxygenated by either hydrodeoxygenation, which removes the oxygen in the form of water, or carboxylation/decarbonylation, which removes the oxygen in the form of CO or CO2.

According to Neste’s renewable diesel product information page, the NExBTL biodiesel provides better performance than conventional biodiesel due to a high cetane number that allows efficient combustion.  Cetane number is a metric for describing the ignition quality of diesel fuel or its components.

The ’798 Publication states:

A high quality hydrocarbon product with good low temperature properties and high cetane number is obtained, employing minimum amount of hydrogen in the process.

According to Neste’s press release, the NExBTL biodiesel enables reductions in greenhouse gas emissions of between 40-80% over the product’s entire life cycle compared to fossil diesel.  The exact number depends on the type of feedstock used and the percentage blending with conventional diesel. 

A second Neste patent application directed to biodiesel production technology is International Publication No. WO 2008/152199 (’199 Publication).  The ’199 Publication, entitled “Process for producing branched hydrocarbons,” is directed to processes for producing saturated hydrocarbons for use as diesel fuels through a condensation step and a combined hydrodefunctionalization and isomerisation step.

The process starts with a biological feedstock and first condenses it, which the ’199 Publication defines as combining two feedstock molecules to form a molecule long enough to serve as a diesel or other fuel. 

Next, the condensed product is subjected to a combined hydrodefunctionalization and isomerisation step to remove oxygen, nitrogen and sulphur atoms and isomerize the molecules into branched hydrocarbons.

According to the ’199 Publication:

The obtained diesel fuels, kerosenes and gasolines can be mixed in conventional fuels without any blending limitations and they fulfill the highest technical requirements without extensive use of additives.

Like the hydrocarbons they produce, Neste’s biodiesel plants are branching out across the globe.  Before the Singapore plant came on stream, the company was operating two renewable diesel plants in Porvoo, Finland.  Neste is also building another facility comparable in scale to the Singapore plant in Rotterdam, which is scheduled to start production in the first half of 2011.

GreenShift’s Eleven Ethanol Patent Suits Converge in Indiana

September 15th, 2010

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In previous posts (here and here), I’ve discussed the series of patent infringement suits brought by GreenShift and its New York subsidiary, GS Cleantech, against a host of ethanol producers across the midwestern United States.

The litigation currently consists of 11 actions in which GreenShift has accused the defendants of infringing U.S. Patent No. 7,601,858 (’858 Patent), entitled “Method of processing ethanol byproducts and related subsystems.”

Last month the Judicial Panel on Multidistrict Litigation granted GreenShift’s motion to consolidate all the cases in the Southern District of Indiana.

In the Transfer Order, the Panel found that there would be common questions of fact among all the cases and consolidation would be more efficient for the courts and more convenient for the parties:

we find that these eleven actions involve common questions of fact, and that centralization . . . in the Southern District of Indiana will serve the convenience of the parties and witnesses and promote the just and efficient conduct of the litigation.

In particular, the Panel noted that the validity and enforceability of the ’858 Patent are likely to be at issue in all eleven actions.

The Panel chose the Southern District of Indiana because it was a satisfactory and relatively convenient forum for most of the defendants:

This district is a primary or alternative choice for transferee forum for all but one responding party.  Moreover, this readily accessible district is near many of the alleged direct infringers — ethanol manufacturers that allegedly employ the patented process — which are scattered throughout the Midwest. 

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.

GreenShift’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.

Defendants in the consolidated litigation include Adkins Energy, Cardinal Ethanol, Big River Resources Galva, Amaizing Energy Atlantic, Center Ethanol, Bushmills Ethanol, United Wisconsin Grain Producers, Blue Flint Ethanol and Iroquois Bio-Energy.

Sundrop’s Solar Gasification Uses Total Concentration

August 23rd, 2010

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Sundrop Fuels (Sundrop) is a Colorado company that combines concentrated solar power (CSP) technology with biofuels production processes. 

While most biomass-to-biofuels systems burn the feedstocks as the first step in biofuel production, Sundrop uses concentrated solar energy to gasify the feedstocks into syngas that is made into advanced biofuels.  According to the company’s web site, the very high temperatures of CSP create efficiencies in the process:

At the center of the Sundrop Fuels process is our proprietary Surroundsun technology, a solar-thermal biomass gasifier that generates temperatures of more than 1,300 degrees Celsius (2,370 degrees Fahrenheit) from the concentrated power of thousands of solar heliostat mirrors.  Using solar energy to drive the endothermic gasification reaction ensures the most efficient use of biomass feedstock to produce liquid advanced biofuels like renewable “green” gasoline.

Sundrop owns at least one U.S. patent and two pending U.S. patent applications relating to its solar gasification technology.   

U.S. Patent No. 7,140,181 (’181 Patent), is entitled “Reactor for solar processing of slightly-absorbing or transparent gases” and is directed to methods for solar powered processing of gases.

The methods described in the ’181 Patent comprise directing concentrated sunlight through an aperture (202) into a spherical chamber (203), where the energy is partially absorbed by the walls (201) of the chamber and partially reflected. 

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Process gas is pumped into the chamber (203) through the aperture (202) and heated by contact with the walls (201) and by infrared radiation from the walls so the gas partially dissociates. 

The gas exits through exit holes (204) and is quickly cooled by its contact with cooling surface (205) to prevent recombination.  It then flows out exhaust tube (206).

Sundrop’s two published patent applications are U.S. Application Pub. No. 2009/0313886, entitled ”Various methods and apparatus for solar assisted chemical and energy processes” (’886 Application) and U.S. Application Pub. No. 2010/0000874, entitled “Various methods and apparatus for solar assisted fuel production” (’874 Application).

The ’886 and ’874 Applications are directed to solar assisted water splitting processes and apparatus to supply synthesis gas for creating a hydrocarbon liquid fuel.  A watter splitter (102) supplies H2 gas to a reverse water gas shift (RWGS) unit (104) that generates synthesis gas for production of liquid fuel such as methanol.   

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The RWGS unit (104) includes a  reverse water gas shift reactor (106) and a liquid fuel synthesis reactor (108) that forms methanol from carbon dioxide hydrogenation. 

A field of heliostats (134), or sun tracking mirrors, reflects sunlight onto the heat exchanger (122) through window (138) in the RWGS unit (104).  The solar energy drives the water splitting process.

According to this Ecogeek piece, by using concentrated solar energy Sundrop’s process more than doubles the yield of fuel that can be produced using ordinary biomass burning processes to 100-125 gallons of fuel per ton of biomass.

Green Patent Acquisitions: BP Buys Verenium’s Biofuels Business

August 13th, 2010

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Last month Verenium announced that BP Biofuels North America would acquire its cellulosic biofuels business for $98.3 million.  

Verenium will retain its commercial enzyme business and maintain rights to its biofuels enzyme products.  In addition, it will have the right to access select biofuels technology that BP develops using the acquired technology and to develop its own cellulosic enzyme program.

The purchase includes Verenium’s  pilot plant and demo-scale facility in Jennings, Louisiana and its R&D facilities in San Diego.

As to intellectual property assets, the Verenium press release says that BP will acquire Verenium’s “cellulosic biofuels technology and related IP” and “cellulosic enzyme technology and related IP.”

It has not been made public which of Verenium’s at least 28 U.S. patents, 23 pending U.S. patent applications and 28 international patent applications are part of the acquisition.  

A search for Verenium’s U.S. patents that contain the terms “cellulosic”, “ethanol” and “enzyme” may provide a hint in the eight hits it yields:  U.S. Patent Nos. 7,741,089, 7,592,434, 7,547,534, 7,504,120, 7,452,706, 7,432,098, 7,432,097 and 7,416,874.  Though some of these patents describe other industrial applications, several relate to phytases or xylanases, enzymes that are useful in ethanol production.

According to this BNET piece, this deal is good for Verenium because it allows the company to sell off the cellulosic ethanol unit that has been losing money and focus on its revenue-generating commercial enzyme business.

In recent years, the two companies have been collaborating on cellulosic ethanol development in two joint ventures called Galaxy Biofuels and Vercipia Biofuels.

GreenShift Adds Another Ethanol Patent Infringement Suit to the Mix

August 5th, 2010

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A previous post discussed GreenShift Corporation’s (GreenShift) volley of recent patent suits against a host of ethanol producers across the midwestern United States. 

In those lawsuits GreenShift accused various ethanol producers of infringing U.S. Patent No. 7,601,858 (’858 Patent), entitled “Method of processing ethanol byproducts and related subsystems.” 

Last month GreenShift added another infringement action to the mix when it sued an Illinois company called Adkins Energy, which runs an ethanol production facility.  The complaint (gs-adkins_complaint.pdf) was filed in the Northern District of Illinois and accuses Adkins of infringing the ’858 Patent.

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.

This latest complaint brings the total to at least ten patent infringement actions brought by GreenShift, all involving allegations of infringing the ’858 Patent. 

Defendants in the other cases include Cardinal Ethanol, Big River Resources Galva, Amaizing Energy Atlantic, Center Ethanol, Bushmills Ethanol, United Wisconsin Grain Producers, Blue Flint Ethanol and Iroquois Bio-Energy.

Novozymes Asserts Ethanol Production Enzyme Patent Against Danisco

June 12th, 2010

Novozymes is a Danish biopharmaceutical company that develops enzymes for a variety of applications, including for use in production of biofuels.

The ink had barely dried on the company’s newly-issued U.S. Patent No. 7,713,723 (’723 Patent) when Novozymes sued its Danish rival Danisco, along with Genencor International Wisconsin, for patent infringement.

The ’723 Patent is entitled “Alpha amylase mutants with altered properties” and is directed to variants of certain alpha amylases that exhibit altered stability under high temperatures, low pH and other conditions.  The patented variants can be used for starch conversion in ethanol production.

According to the complaint (novozymes_complaint.pdf), filed in the Western District of Wisconsin, the defendants are infringing the ’723 Patent by selling alpha amylase enzymes including Danisco’s GC358 product.

This is not the first time these Danish rivals have litigated a patent relating to enzymes for ethanol production.  In 2007, Danisco paid Novozymes $15.3 million to settle a lawsuit involving alleged infringement of a patent for the enzyme spezyme ethyl.

Green Patent PR: Marketing Clean Tech on the Fast Track

May 26th, 2010

Perhaps it’s too early to call it a trend.  But clean technology companies have begun to use the fast tracking procedure offered by the U.S. Patent and Trademark Office’s (USPTO) Green Technology Pilot Program for PR purposes. 

Last month, GreenShift Corporation (GreenShift), a New York company that develops processes for ethanol production, announced that one of its patent applications was accepted into the program.  A little research indicates that the lucky application is Application Publication No. 2008/0299632 (’632 Application).

The ’632 Application is entitled “Methods for recovering oil from a fractionated dry milling process” and is directed to methods for recovering oil from fthin stillage produced in a fractionation-based dry milling process.  The invention enables recovery of oil from byproducts created during corn ethanol production.

David Winsness, GreenShift’s CTO and a named co-inventor on the ’632 Application, said the company is “pleased that one of our pending applications has been accepted into this important and timely program” and is looking forward to “additional opportunities to deliver our clients the powerful cost advantages made possible by our patented technologies.”

If the ’632 Application issues as a patent in the near future, it might join U.S. Patent No. 7,601,858 in GreenShift’s recently expanded slate of patent infringement suits against a number of different ethanol producers.

Similarly, Silicon Valley concentrating PV company Skyline Solar (Skyline) recently announced that the USPTO granted U.S. Patent No. 7,709,730 (’730 Patent) after expedited examination via the Green Technology Pilot Program. 

The ’730 Patent is entitled “Dual trough concentrating solar photovoltaic module” and is directed to a solar energy collector having a dual trough design.  The collector (100) has two optical apertures (101a, 101b) that admit sunlight onto reflector panels (106).

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Each of two adjacent reflector troughs (120a, 120b) has a base (124a, 124b) and a pair of reflective side walls formed from the reflector panels (106).

Skyline markets the patented technology as High Gain Solar (HGS) architecture, and the press release says HGS packs more power and is easier to deploy than traditional flat panel CPV systems:

Skyline’s HGS architecture delivers ten times more energy per gram of silicon versus traditional flat-panel systems in sunny locations and offers industry-leading energy density.  Skyline HGS arrays combine industry-proven silicon cells, durable reflector materials and single-axis tracking into a complete, easy-to-deploy system.

According to its press release, Skyline is “one of the first companies to receive patent approval under the USPTO’s Green Technology Pilot Program.” 

It certainly won’t be the last.  With the USPTO recently loosening up the eligibility requirements for the Green Technology Pilot Program, there should be many more applications accepted into the program, more patents granted as a result and more green patent PR surrounding the success stories.

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.