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Perfluorohexanesulfonic acid (PFHxS) (
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reve ...
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 element ...
. It is one of many compounds collectively known as
per- and polyfluoroalkyl substances Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 milli ...
(PFASs). It is an
anion 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 conven ...
ic
fluorosurfactant Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic Organofluorine chemistry, organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl ...
and a
persistent organic pollutant Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because ...
with
bioaccumulative Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance faster than it can be lost or eliminated by catabolism and excretion. ...
properties. Although the use of products containing PFHxS and other
PFASs Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 millio ...
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.


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 C6 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.


Biochemical properties

PFHxS has a six
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
fluorocarbon Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are ...
chain that is both hydrophobic and lipophobic. Its
sulfonic acid In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula , where R is an organic alkyl or aryl group and the group a sulfonyl hydroxide. As a substituent, it is kn ...
functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
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 of the proteins of the albumin family are water- soluble, moderately soluble in concentrated salt solutions, and experience heat denaturation. Alb ...
, and relatively little PFHxS is found in the liver compared to longer chain PFASs such as PFOS. The half-life of PFHxS in adult blood serum is 5.3 years (4.7 years for women and 7.4 years for men).The
half-life Half-life is a mathematical and scientific description of exponential or gradual decay. Half-life, half life or halflife may also refer to: Film * Half-Life (film), ''Half-Life'' (film), a 2008 independent film by Jennifer Phang * ''Half Life: ...
of PFASs in human blood generally decreases with decreasing backbone (CF2) 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.


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 ...
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 the Earth, global intergovernmental organization established by the signing of the Charter of the United Nations, UN Charter on 26 June 1945 with the stated purpose of maintaining international peace and internationa ...
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 organi ...
. 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 and COVID pandemic), caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), began with an disease outbreak, outbreak of COVID-19 in Wuhan, China, in December ...
, 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 Tolerable daily intake (TDI) refers to the daily amount of a chemical contaminant that has been assessed safe for human exposure on long-term basis (usually whole lifetime). TDI specifically occurs to chemicals that humans are exposed to unintenti ...
(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 it is a perfluorosulfonic acid and a perfluoroalkyl su ...
,
PFOA Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, from its chemical formula C8HF15O2) is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical process ...
, 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 drops to below 90 ng/L, 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 agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...
(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 U.S. state, state in the Upper Midwestern region of the United States. It is bordered by the Canadian provinces of Manitoba and Ontario to the north and east and by the U.S. states of Wisconsin to the east, Iowa to the so ...
recommends a guidance value of 0.027 μg/L for PFHxS, and
Michigan Michigan ( ) is a peninsular U.S. state, state in the Great Lakes region, Great Lakes region of the Upper Midwest, Upper Midwestern United States. It shares water and land boundaries with Minnesota to the northwest, Wisconsin to the west, ...
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, setting a
maximum contaminant level Maximum contaminant levels (MCLs) are standards that are set by the United States Environmental Protection Agency (EPA) for drinking water quality.Joseph Cotruvo, Victor Kimm, Arden Calvert“Drinking Water: A Half Century of Progress.”EPA Alumn ...
(MCL) of 51 parts per trillion (ppt) or 0.051 μg/L.


See also

*
Perfluorooctanesulfonic acid Perfluorooctanesulfonic acid (PFOS) (conjugate acid, conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group, and thus it is a perfluorosulfonic acid and a Per ...
*
Per- and polyfluoroalkyl substances Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 milli ...
*
Timeline of events related to per- and polyfluoroalkyl substances This timeline of events related to per- and polyfluoroalkyl substances (PFASs) includes events related to the discovery, development, manufacture, marketing, uses, concerns, litigation, regulation, and legislation, involving the human-made flu ...


References

{{Reflist, 30em


External links


Minnesota guidance on PFHxS
Anionic surfactants Persistent organic pollutants under the Stockholm Convention Endocrine disruptors Perfluorosulfonic acids