Perfluorohexanesulfonic acid (PFHxS) (
conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
perfluorohexanesulfonate) is a synthetic
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...
. It is one of many compounds collectively known as
per- and polyfluoroalkyl substances
Per- and polyfluoroalkyl substances (PFASs) are synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalky ...
(PFASs). It is an
anionic
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
fluorosurfactant
Per- and polyfluoroalkyl substances (PFASs) are synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalkyl ...
and a
persistent organic pollutant
Persistent organic pollutants (POPs), sometimes known as "forever chemicals", are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adverse ...
with
bioaccumulative properties. Although the use of products containing PFHxS and other
PFASs
Per- and polyfluoroalkyl substances (PFASs) are synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalkyl mo ...
have been banned or are being phased out in many jurisdictions, it remains ubiquitous in many environments and within the general population, and is one of the most commonly detected PFASs.
Biochemical properties
PFHxS has a six
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes ...
fluorocarbon
Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often has distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Fluorocarbons and their derivatives are commerci ...
chain that is both hydrophobic and lipophobic. Its
sulfonic acid functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...
imparts polarity, and allows it to interact with other polar compounds. Due to the strength of its
carbon-fluorine bonds, it persists in the environment and in living organisms.
In humans, PFHxS binds to blood
albumin
Albumin is a family of globular proteins, the most common of which are the serum albumins. All the proteins of the albumin family are water-soluble, moderately soluble in concentrated salt solutions, and experience heat denaturation. Albumins ...
,
[ ] and relatively little PFHxS is found in the liver compared to longer chain PFASs such as PFOS.
[ ] The
half-life
Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable at ...
of PFASs in human blood generally decreases with decreasing backbone (CF
2) length. However, PFHxS is an unusual exception in that its half-life is greater than both longer and shorter chain equivalents such as PFOS or
PFBS.
[ ]
Production
PFHxS, its salts and isomers are anthropogenic chemicals that do not occur naturally. It is used as a surfactant and protective coating in applications such as aqueous firefighting foams, textile coating, metal plating and in polishing agents.
PFHxS production is slowly being phased out since
3M stopped producing C
6 fluorotelomers in 2002, but production by other companies may be ongoing.
Between 1958 and 2015, an estimated 120-1022 metric tonnes of PFHxS were produced.
PFHxS was also used as replacement for PFOS after the Stockholm Convention on persistent organic pollutants restricted the use of PFOS.
The exact quantity of PFHxS produced or in production is difficult to estimate, as production volumes and relevant formulation information is often not publicly available. PFHxS may also be formed as an impurity of PFOS production, or as a breakdown product of larger PFASs.
[ ]
Occurrence in Humans
Data from the 2003-2004
National Health and Nutrition Examination Survey
The National Health and Nutrition Examination Survey (NHANES) is a survey research program conducted by the National Center for Health Statistics (NCHS) to assess the health and nutritional status of adults and children in the United States, and to ...
in the United States found the average serum concentration of PFHxS in the general US population to be 1.9 μg/L, with the 10th and 90th percentiles being 0.7 and 8.3 μg/L, respectively. Some studies reported serum PFHxS concentrations in the United States to be gradually decreasing since at least 1999.
[ ][ ] Nevertheless, evidence of exposure can be detected amongst people with historic exposure. Serum concentrations of PFHxS were elevated amongst a cohort of Australian firefighters with occupational exposure to PFHxS (mean = 33 μg/L) compared to the general Australian population (mean = 3.2 μg/L), and were significantly correlated with serum PFOS concentrations.
[ ] As with PFOS, serum PFHxS concentrations are lower amongst women and people who reported blood donation.
[ ]
There is limited evidence for a relationship between PFHxS exposure and various health outcomes. However, contributions from PFHxS specifically are difficult to isolate, as most studies in humans and higher order organisms investigate exposure to a complex mixture of PFASs, of which PFHxS is just one component.
Regulatory status
A number of jurisdictions have guidelines or limits for the concentration of PFHxS in water, in diets, and in the environment. There are fewer regulations on PFHxS compared to PFOS and PFOA. This reflects the relative lack of epidemiological and toxicological information on the human health effects of exposure to PFHxS.
PFHxS, its salts and related compounds have been recommended to be added to Annex A of the
United Nations
The United Nations (UN) is an intergovernmental organization whose stated purposes are to maintain international peace and security, develop friendly relations among nations, achieve international cooperation, and be a centre for harmonizi ...
Stockholm Convention on Persistent Organic Pollutants
Stockholm Convention on Persistent Organic Pollutants is an international environmental treaty, signed on 22 May 2001 in Stockholm and effective from 17 May 2004, that aims to eliminate or restrict the production and use of persistent organ ...
. The decision was initially scheduled to be made in June 2021.
Due to the
COVID-19 pandemic
The COVID-19 pandemic, also known as the coronavirus pandemic, is an ongoing global pandemic of coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The novel virus was first identified ...
, the decision at the conference of parties was deferred to June 2022, where the parties agreed to list PFHxS, its salts and related compounds in Annex a without specific exemptions. Upon entry into force, nations party to the convention are legally bound to take act to cease production and use of PFHxS. Several hundred salts and precursors of PFHxS fall within the scope of the restriction.
Australia
Food Standards Australia New Zealand found insufficient evidence to justify a
tolerable daily intake (TDI) for PFHxS specifically. Therefore the TDI level for PFOS (0.02 μg/kg) was adapted as the TDI for the sum of PFOS and PFHxS. Australia uses a drinking water guideline value of 0.07 μg/L for the sum of PFHxS and PFOS. In comparison, the drinking water guideline value for PFOA is 0.56 μg/L.
Europe
A new EU drinking water directive issued in 2020 adopted PFAS limit values. The limit values are 0.1 μg/L for the sum of 20 PFASs including PFHxS, and 0.5 μg/L for the sum of all PFASs. This directive is binding for all EU member nations. It is a minimum directive, and member states can elect to adopt stricter regulations.
Denmark
The Danish EPA has established a drinking water and groundwater limit value of 2 ng/L for the sum of 4 PFASs; , PFHxS,
PFOS
Perfluorooctanesulfonic acid (PFOS) ( conjugate base perfluorooctanesulfonate) is a chemical compound having an eight- carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man ...
,
PFOA
Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, for its 8 carbon chain structure) is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes a ...
, and perfluorononanoic acid (PFNA).
Sweden
The Swedish National Food Agency recommends a drinking water limit of 0.09 μg/L for the sum of 11 PFASs (PFBS, PFHxS, PFOS, 6:2 FTSA, PFBA, PFPeA, PFHxA, PFHpA, PFOA, PFNA and PFDA). If PFASs are found above this limit in drinking water, immediate action is recommended to reduce the PFAS concentration in the drinking water to as far below the action level as possible. If PFASs is found above 900 ng/L in drinking water, the advice is to avoid drinking the water or preparing food with the water until the concentration is reduced as low as possible below 90 ng/litre, and to contact the Swedish Food Agency.
Republic of Korea
In 2018, a preliminary drinking water limit value of 0.48 μg/L was adopted for PFHxS. In comparison, the preliminary limit value for the sum of PFOS and PFOA is 0.07 μg/L.
United States
As of 2019, there is no federal limit or guideline value for PFHxS. The
United States Environmental Protection Agency
The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...
(EPA) is developing toxicity values for PFHxS, as well as PFBA, PFHxA, PFNA and PFDA.
Meanwhile, some states have adopted their own guideline values for PFHxS. For example,
Minnesota
Minnesota () is a state in the upper midwestern region of the United States. It is the 12th largest U.S. state in area and the List of U.S. states and territories by population, 22nd most populous, with over 5.75 million residents. Minne ...
recommends a guidance value of 0.027 μg/L for PFHxS,
and
Michigan
Michigan () is a U.S. state, state in the Great Lakes region, Great Lakes region of the Upper Midwest, upper Midwestern United States. With a population of nearly 10.12 million and an area of nearly , Michigan is the List of U.S. states and ...
has a screening level of 0.084 μg/L for PFHxS.
In 2020, Michigan adopted drinking water standards for 5 previously unregulated PFASs including PFHxS, which has a
maximum contaminant level (MCL) of 51 parts per trillion (ppt) or 0.051 μg/L.
See also
*
Perfluorooctanesulfonic acid
Perfluorooctanesulfonic acid (PFOS) ( conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man ...
*
Per- and polyfluoroalkyl substances
Per- and polyfluoroalkyl substances (PFASs) are synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalky ...
*
References
{{Reflist, 30em
External links
Minnesota guidance on PFHxS
Anionic surfactants
Persistent organic pollutants under the Stockholm Convention
Endocrine disruptors
Perfluorosulfonic acids