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Analytical Chemistry

A tale of PFAS, pollution, and patent claims

A novel legal maneuver by Solvay threatens the availability of an analytical standard

by Cheryl Hogue , Craig Bettenhausen
March 27, 2021 | A version of this story appeared in Volume 99, Issue 11


A photo of a site on the Po River in Italy.
Credit: Shutterstock
Researchers in Italy are investigating C6O4 contamination of the Po River delta. But they cannot obtain an analytical standard for this member of the per- and polyfluoroalkyl substances family.

Analytical reference standards are not known for attracting intrigue and drama. Standards—compounds of known purity and concentration—are pivotal to investigating pollution because they allow researchers to determine the levels of contaminants in water, soil, or tissue samples. Recently, though, the specter of patent infringement lawsuits has prevented researchers from quantifying environmental contamination by a perfluorinated “forever chemical.”

This complicated situation involves the Brussels-based chemical maker Solvay, a Canadian analytical standards company, pollution by per- and polyfluoroalkyl substances (PFAS) in Italy, and the complexities of patent law.

Earlier this year, Solvay told the analytical standards firm Wellington Laboratories to cease making and selling a standard for C6O4, a chemical used as a processing aid for making commercial PFAS compounds. Solvay, which makes and uses C6O4 in Italy but does not sell it, holds patents on the compound and its synthesis in several countries.

The use of patent infringement claims to take an analytical reference standard off the market is a new idea to the experts on patent law and reference standards consulted by C&EN. Analytical chemists are concerned that the maneuver could have a chilling effect on efforts to trace the sources of pollution.

The background of C6O4

C6O4 is the nickname for a monocyclic perfluorinated ether. It is a substitute for an older chemical in the PFAS group that was used for decades: the toxic and environmentally persistent perfluoro­octanoic acid (PFOA).

Solvay registered C6O4 in 2011 under the European Union’s Registration, Evaluation, Authorisation, and Restriction of Chemicals (REACH) law. In the registration documents, Solvay identifies the chemical as a production intermediate that isn’t intended for environmental release.

This is an example of how patents are misused to prevent [government] authorities and scientists from detecting pollution and demonstrating risk.
Sara Valsecchi, researcher, Italian National Research Council

The company employs the ammonium salt of C6O4 to manufacture fluoropolymers such as polytetrafluoroethylene, which are used as nonstick coatings on cooking utensils and other food-contact articles, according to a 2014 scientific opinion from the European Food Safety Authority. The opinion concludes “There is no safety concern for the consumer if the substance is only to be used as a polymer production aid during the manufacture of fluoropolymers which are produced under high temperature conditions of at least 370 °C” (EFSA J. 2014, DOI: 10.2903/j.efsa.2014.3718).

But even though C6O4 was supposed to remain within industrial processing equipment, officials from Italy’s Veneto region in 2019 found the compound in the Po, the country’s longest river. Upstream of Veneto, the area that drains into the river includes part of Italy’s Piedmont region where a Solvay fluoropolymer plant operates in the town of Spinetta Marengo, near Alessandria. The river empties into the Adriatic Sea in Italy’s northeast.

In addition to the Solvay plant, landfills in the Piedmont region that accepted industrial waste are also contributing C6O4 to the Po River, says Sara Valsecchi, a researcher at the Italian National Research Council. “We found significant concentrations of this compound in landfill leachates,” she says.

Solvay wasn’t the only company that registered C6O4 in the EU. Another business in Italy did too.

That was Miteni, whose facility in Trissino, Italy, reclaimed fluoroethers from industrial waste. For years, the plant processed materials from the Chemours plant in Dordrecht, the Netherlands. In 2017, officials in the Veneto region announced they’d found hexafluoropropylene oxide dimer acid (HFPO-DA), a perfluorinated compound, in wells near the Miteni facility. That chemical is the product of hydrolysis of Chemours’s substitute for PFOA, a fluoroether called GenX.

PFAS in the Po
Solvay makes and uses C6O4 at a factory in Spinetta Marengo near a tributary of the Po River in Italy’s Piedmont region. Officials in the Veneto region, in the country’s northeast, found the chemical near the mouth of the Po. They also found C6O4 and another fluorinated compound in groundwater near a shuttered Miteni facility in Trissino.
A map of Italy's Piedmont region that shows sites relevant to C6O4 pollution.
Credit: C&EN/© Map Resources

Miteni shut down, and an Italian court declared it bankrupt at the end of 2018. At that time, the Regional Agency for Environmental Prevention and Protection of Veneto learned that the facility accepted waste from Solvay, recovered C6O4 from it, and sent the substance back to Solvay, Valsecchi says. The agency also discovered C6O4 in groundwater near the shuttered Miteni facility, an area hydrologically separate from the Po River.

Valsecchi is collaborating with other scientists to investigate the distribution, bioaccumulation, and effects of C6O4 in the environment, notably in clams—which are grown commercially in the Po delta and wind up on dinner tables—and the eggs of wild birds. They have two papers in process, and a third was recently published (Environ. Int. 2021, DOI: 10.1016/j.envint.2021.106484).

The lack of a chemical standard for C6O4 “will surely slow down or stop our investigations,” Valsecchi tells C&EN. “This is an example of how patents are misused to prevent [government] authorities and scientists from detecting pollution and demonstrating risk” of new PFAS that are entering the environment.

Trade secrets

Solvay says this wasn’t its intent. Solvay asked Wellington to stop making a C6O4 analytical standard to ensure that any standard is actually the company’s patented molecule, spokesperson Brian Carroll says. Solvay doesn’t know the origin of the standard that Wellington offered and never provided samples of C6O4 to Wellington, he says.

Solvay also doesn’t want the compound—even in the small amount that makes up a reference standard—sold to other chemical makers, Carroll says. “Solvay’s concern is about not enabling competitors to duplicate or develop a competitive product,” he explains in an email to C&EN.

A line structure of C6O4.

“Solvay attempted to negotiate a license agreement with Wellington that would protect Solvay’s intellectual property from competitors,” Carroll says. But Wellington “preferred to discontinue” sales of C6O4 standards, he says.

In a Jan. 27 letter to its customers, Wellington says it learned in July 2020 that the sale of the C6O4 standard “constituted an infringement of Solvay’s patent rights.”

“We were hoping to negotiate an arrangement with the patent holder that would facilitate the sale of this standard so that environmental analyses could continue; however, we were unable to come to an agreement that would allow for uncensored access to the standard,” the letter says. Wellington representatives shared with C&EN some information about the situation and patents in question but declined to discuss the situation in detail.

Wellington, based in Guelph, Ontario, is a major provider of PFAS analytical standards as well as a supplier of raw materials to other standards companies. Shutting down the sale of Wellington’s C6O4 standard may well make the standard unavailable for anyone other than Solvay.

Stephen J. Arpie, director at Absolute Standards, another maker of reference materials, says he can buy about half the more common PFAS from any number of open-market sources, such as Sigma-Aldrich. “But for some of the exotic ones, they’re the only game in town,” he says, referring to Wellington. And Arpie says Wellington is also the only provider of isotope-labeled PFAS, which enable several precise and sensitive analytical methods.

The other side of the coin, however, is that the market for C6O4 standards may be too small for Wellington or anyone else to risk a lawsuit from Solvay. “That one compound over its lifetime would maybe make them $1 million,” Arpie says. “For one compound, they’re not going to take the heat.”

The legal situation is complex: a Belgian company claiming patent infringement against a Canadian company for providing standards that are currently most relevant to pollution in Italy, with the patents in question registered in several countries but not Canada or Italy.

Solvay’s concern is about not enabling competitors to duplicate or develop a competitive product.
Brian Carroll, spokesperson, Solvay

Wellington wouldn’t have infringed anything if the reference standard stayed within Canada, according to Bryan Diner, a patent attorney at the intellectual property law firm Finnegan, Henderson, Farabow, Garrett & Dunner. But if the standard crossed into one of the countries where Solvay holds patents, including the US, Wellington would be exposed to legal action from Solvay.

Solvay’s Carroll tells C&EN that the company is in discussion with a laboratory—not Wellington—to generate a certified reference standard for C6O4, but there was no deal as of C&EN’s deadline.

Other standards sought

Meanwhile, a second struggle over the availability of standards for PFAS connected to Solvay is playing out in the US.

Last year, scientists from the US Environmental Protection Agency and the New Jersey Department of Environmental Protection detected novel PFAS in soil near a Solvay plant in West Deptford, New Jersey. The researchers identified 10 distinct chloro­perfluoropolyether carboxylates, w­hich the state says have toxicities similar to that of PFOA (Science 2020, DOI: 10.1126/science.aba7127). According to Valsecchi, those chloroperfluoropolyether carboxylates, fluorosurfactants used as substitutes for PFOA, were made at the Solvay plant in Spinetta Marengo, Italy, and shipped to the New Jersey factory.

Solvay’s CEO announced in October that the company is phasing out fluorosurfactant processing aids at the West Deptford plant and will be in full production of new alternatives there by mid-2021.

A row of vials of PFAS analytical standards.
Credit: Absolute Standards
Standards like these are crucial for scientists to identify and quantify chemicals from water or soil samples.

Then, in November, New Jersey filed a lawsuit against Solvay to stop the chloroperfluoropolyether carboxylate pollution. It also asked Solvay to provide analytical standards for the PFAS used at the plant. In an argument similar to the one Solvay made against Wellington, the company claimed the identity of those compounds as trade secrets, the lawsuit says.

The New Jersey Department of Environmental Protection is still seeking appropriate analytical standards for those compounds, department spokesperson Larry Hajna tells C&EN.

Attorneys tell C&EN that researchers in the US may have some legal options if Solvay’s practice on analytical standards becomes more widespread, but they would need the backing of the federal government. Each legal approach has precedent in other corners of the intellectual property landscape but would, like the infringement claims, be new to analytical reference standards.

Bradford Frese, a patent attorney at Arent Fox, says US law includes a provision known as section 1498 that gives the federal government access to a patented invention in a process akin to eminent domain. The provision allows the government to contract with an outside, US-based lab to make and use the invention on the government’s behalf without the patent holder’s consent. The patent holder is able to sue only the government, not the lab, and courts have frequently limited judgments in such cases to a reasonable royalty, Frese says.

A heavier lift, but not out of the question, would be for Congress to expand the Hatch-Waxman act, Frese says. That 1984 law created the generic-drug business as we know it by making it legal to prepare a molecule still under patent protection if it’s for the purpose of submitting regulatory data to the US Food and Drug Administration. That law is how generic drugs can hit shelves almost immediately after a patent expires. Expanding that “safe harbor” exemption to include submission of data to the EPA could allow the most critical public safety analyses to go forward without intellectual property concerns.

Diner mentions a third, more aggressive avenue. In some other industries, such as drugs and semiconductors, firms accused of patent infringement have successfully challenged the validity of the patent at issue. The US Patent and Trademark Office has procedures for doing so that are less costly and complicated than a lawsuit would usually be.

Those legal routes could free up analytical reference standards for proprietary molecules, but only if someone is willing to pursue them. In the case of Solvay’s PFAS, researchers will likely have to wait until the company releases a standard, which Absolute Standards’ Arpie thinks is fair.

“My position is that while we’d like to get materials that are on patent, we don’t have a right. We’re not entitled just because we can think of it and we think it’s right,” Arpie says. “We’ve all agreed to a different construct called patent protection, and it’s served our world community very well so far.”


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