Biological aspects of fluorine

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PET scan using fluorine-18 PET-MIPS-anim.gif
PET scan using fluorine-18

Fluorine may interact with biological systems in the form of fluorine-containing compounds. Though elemental fluorine (F2) is very rare in everyday life, fluorine-containing compounds such as fluorite occur naturally as minerals. Naturally occurring organofluorine compounds are extremely rare. Man-made fluoride compounds are common and are used in medicines, pesticides, and materials. Twenty percent of all commercialized pharmaceuticals contain fluorine, including Lipitor and Prozac. [1] [2] In many contexts, fluorine-containing compounds are harmless or even beneficial to living organisms; in others, they are toxic.

Contents

Aside from their use in medicine, man-made fluorinated compounds have also played a role in several noteworthy environmental concerns. Chlorofluorocarbons (CFCs), once major components of numerous commercial aerosol products, have proven damaging to Earth's ozone layer and resulted in the wide-reaching Montreal Protocol; though in truth the chlorine in CFCs is the destructive actor, fluorine is an important part of these molecules because it makes them very stable and long-lived. Similarly, the stability of many organofluorine compounds has raised the issue of biopersistence. Long-lived molecules from waterproofing sprays, for example PFOA and PFOS, are found worldwide in the tissues of wildlife and humans, including newborn children.

Fluorine biology is also relevant to a number of cutting-edge technologies. PFCs (perfluorocarbons) are capable of holding enough oxygen to support human liquid breathing. Organofluorine in the form of its radioisotope 18F is also at the heart of a modern medical imaging technique known as positron emission tomography (PET). A PET scan produces three-dimensional colored images of parts of the body that use a lot of sugar, particularly the brain or tumors.

Dental care

Since the mid-20th century, it has been discerned from population studies (though incompletely understood) that fluoride reduces tooth decay. Initially, researchers hypothesized that fluoride helped by converting tooth enamel from the more acid-soluble mineral hydroxyapatite to the less acid-soluble mineral fluorapatite. However, more recent studies showed no difference in the frequency of caries (cavities) between teeth that were pre-fluoridated to different degrees. Current thinking is that fluoride prevents cavities primarily by helping teeth that are in the very early stages of tooth decay. [3]

Topical fluoride treatment in Panama US Navy 090526-F-1333S-023 A service member embarked aboard the Military Sealift Command hospital ship USNS Comfort (T-AH 20) gives a Fluoride treatment to a patient during a Continuing Promise 2009 medical civil service projec.jpg
Topical fluoride treatment in Panama

When teeth begin to decay from the acid produced by sugar-consuming bacteria, calcium is lost (demineralization). However, teeth have a limited ability to recover calcium if decay is not too far advanced (remineralization). Fluoride appears to reduce demineralization and increase remineralization. Also, there is some evidence that fluoride interferes with the bacteria that consume sugars in the mouth and make tooth-destroying acids. [3] In any case, it is only the fluoride that is directly present in the mouth (topical treatment) that prevents cavities; fluoride ions that are swallowed do not benefit the teeth. [3]

Water fluoridation is the controlled addition of fluoride to a public water supply in an effort to reduce tooth decay in people who drink the water. [4] Its use began in the 1940s, following studies of children in a region where water is naturally fluoridated. It is now used widely in public water systems in the United States and some other parts of the world, such that about two-thirds of the U.S. population is exposed to fluoridated water supplies [5] and about 5.7% of people worldwide. [6] Although the best available evidence shows no association with adverse effects other than fluorosis (dental and, in worse cases, skeletal), most of which is mild, [7] water fluoridation has been contentious for ethical, safety, and efficacy reasons, [6] and opposition to water fluoridation exists despite its widespread support by public health organizations. [8] The benefits of water fluoridation have lessened recently, presumably because of the availability of fluoride in other forms, but are still measurable, particularly for low-income groups. [9] Systematic reviews in 2000 and 2007 showed significant reduction of cavities in children exposed to water fluoridation. [10]

Sodium fluoride, tin difluoride, and, most commonly, sodium monofluorophosphate, are used in toothpaste. In 1955, the first fluoride toothpaste was introduced in the United States. Now, almost all toothpaste in developed countries is fluoridated. For example, 95% of European toothpaste contains fluoride. [9] Gels and foams are often advised for special patient groups, particularly those undergoing radiation therapy to the head (cancer patients). The patient receives a four-minute application of a high amount of fluoride. Varnishes, which can be more quickly applied, exist and perform a similar function. Fluoride is also often present in prescription and non-prescription mouthwashes and is a trace component of foods manufactured using fluoridated water supplies. [11]

Medical applications

Pharmaceuticals

Prozac, one of several notable fluorine-containing drugs Prozac pills.jpg
Prozac, one of several notable fluorine-containing drugs

Of all commercialized pharmaceutical drugs, twenty percent contain fluorine, including important drugs in many different pharmaceutical classes. [12] Fluorine is often added to drug molecules during drug design, as even a single atom can greatly change the chemical properties of the molecule in desirable ways.

Because of the considerable stability of the carbon–fluorine bond, many drugs are fluorinated to delay their metabolism, which is the chemical process in which the drugs are turned into compounds that allows them to be eliminated. This prolongs their half-lives and allows for longer times between dosing and activation. For example, an aromatic ring may prevent the metabolism of a drug, but this presents a safety problem, because some aromatic compounds are metabolized in the body into poisonous epoxides by the organism's native enzymes. Substituting a fluorine into a para position, however, protects the aromatic ring and prevents the epoxide from being produced. [13]

Adding fluorine to biologically active organic compounds increases their lipophilicity (ability to dissolve in fats), because the carbon–fluorine bond is even more hydrophobic than the carbon–hydrogen bond. This effect often increases a drug's bioavailability because of increased cell membrane penetration. [14] Although the potential of fluorine being released in a fluoride leaving group depends on its position in the molecule, [15] organofluorides are generally very stable, since the carbon–fluorine bond is strong.

Fluorines also find their uses in common mineralocorticoids, a class of drugs that increase the blood pressure. Adding a fluorine increases both its medical power and anti-inflammatory effects. [16] Fluorine-containing fludrocortisone is one of the most common of these drugs. [17] Dexamethasone and triamcinolone, which are among the most potent of the related synthetic corticosteroid class of drugs, contain fluorine as well. [17]

Several inhaled general anesthetic agents, including the most commonly used inhaled agents, also contain fluorine. The first fluorinated anesthetic agent, halothane, proved to be much safer (neither explosive nor flammable) and longer-lasting than those previously used. Modern fluorinated anesthetics are longer-lasting still and almost insoluble in blood, which accelerates the awakening. [18] Examples include sevoflurane, desflurane, enflurane, and isoflurane, all hydrofluorocarbon derivatives. [19]

Prior to the 1980s, antidepressants altered not only serotonin uptake but also the uptake of altered norepinephrine; the latter caused most of the side effects of antidepressants. The first drug to alter only the serotonin uptake was Prozac; it gave birth to the extensive selective serotonin reuptake inhibitor (SSRI) antidepressant class and is the best-selling antidepressant. Many other SSRI antidepressants are fluorinated organics, including Celexa, Luvox, and Lexapro. [20] Fluoroquinolones are a commonly used family of broad-spectrum antibiotics. [21]

Molecular structures of several fluorine-containing pharmaceuticals
Atorvastatin-3D-vdW.png Fluorouracil-3D-vdW.png Fludrocortisone-from-xtal-1972-matt-3D-sf.png Isoflurane-3D-vdW.png
Lipitor (atorvastatin)5-FU (fluorouracil)Florinef (fludrocortisone)Isoflurane

Scanning

PET scan for diagnosis of Alzheimer's disease PET scan-normal brain-alzheimers disease brain.PNG
PET scan for diagnosis of Alzheimer's disease

Compounds containing fluorine-18, a radioactive isotope that emits positrons, are often used in positron emission tomography (PET) scanning, because the isotope's half-life of about 110 minutes is usefully long by positron-emitter standards. One such radiopharmaceutical is 2-deoxy-2-(18F)fluoro-D-glucose (generically referred to as fludeoxyglucose), commonly abbreviated as 18F-FDG, or simply FDG. [22] In PET imaging, FDG can be used for assessing glucose metabolism in the brain and for imaging cancer tumors. After injection into the blood, FDG is taken up by "FDG-avid" tissues with a high need for glucose, such as the brain and most types of malignant tumors. [23] Tomography, often assisted by a computer to form a PET/CT (CT stands for "computer tomography") machine, can then be used to diagnose or monitor treatment of cancers, especially Hodgkin's lymphoma, lung cancer, and breast cancer. [24]

Natural fluorine is monoisotopic, consisting solely of fluorine-19. Fluorine compounds are highly amenable to nuclear magnetic resonance (NMR), because fluorine-19 has a nuclear spin of 1⁄2, a high nuclear magnetic moment, and a high magnetogyric ratio. Fluorine compounds typically have a fast NMR relaxation, which enables the use of fast averaging to obtain a signal-to-noise ratio similar to hydrogen-1 NMR spectra. [25] Fluorine-19 is commonly used in NMR study of metabolism, protein structures and conformational changes. [26] In addition, inert fluorinated gases have the potential to be a cheap and efficient tool for imaging lung ventilation. [27]

Oxygen transport research

Liquid fluorocarbons have a very high capacity for holding gas in solution. They can hold more oxygen or carbon dioxide than blood does. For that reason, they have attracted ongoing interest related to the possibility of artificial blood or of liquid breathing. [28]

Computer-generated model of nanocrystal of perflubron (red) and gentamicin (white, an antibiotic) Perflubron and gentamicin molecules.png
Computer-generated model of nanocrystal of perflubron (red) and gentamicin (white, an antibiotic)

Blood substitutes are the subject of research because the demand for blood transfusions grows faster than donations. In some scenarios, artificial blood may be more convenient or safe. Because fluorocarbons do not normally mix with water, they must be mixed into emulsions (small droplets of perfluorocarbon suspended in water) in order to be used as blood. [29] [30] One such product, Oxycyte, has been through initial clinical trials. [31] [32]

Possible medical uses of liquid breathing (which uses pure perfluorocarbon liquid, not a water emulsion) involve assistance for premature babies or for burn patients (if normal lung function is compromised). Both partial and complete filling of the lungs have been considered, although only the former has undergone any significant tests in humans. Several animal tests have been performed and there have been some human partial liquid ventilation trials. [33] One effort, by Alliance Pharmaceuticals, reached clinical trials but was abandoned because of insufficient advantage compared to other therapies. [34]

Nanocrystals represent a possible method of delivering water- or fat-soluble drugs within a perfluorochemical fluid. The use of these particles is being developed to help treat babies with damaged lungs. [35]

Perfluorocarbons are banned from sports, where they may be used to increase oxygen use for endurance athletes. One cyclist, Mauro Gianetti, was investigated after a near-fatality where PFC use was suspected. [36] [37] Other posited applications include deep-sea diving and space travel, applications that both require total, not partial, liquid ventilation. [38] [39] The 1989 film The Abyss depicted a fictional use of perfluorocarbon for human diving but also filmed a real rat surviving while cooled and immersed in perfluorocarbon. [40] (See also list of fictional treatments of perfluorocarbon breathing.)

Agrichemicals

An estimated 30% of agrichemical compounds contain fluorine. [41] Most of them are used as poisons, but a few stimulate growth instead.

Sign warning of poisonous sodium fluoroacetate baits 1080PoisonWarning gobeirne.png
Sign warning of poisonous sodium fluoroacetate baits

Sodium fluoroacetate has been used as an insecticide, but it is especially effective against mammalian pests. [42] The name "1080" refers to the catalogue number of the poison, which became its brand name. [43] Fluoroacetate is similar to acetate, which has a pivotal role in the Krebs cycle (a key part of cell metabolism). Fluoroacetate halts the cycle and causes cells to be deprived of energy. [43] Several other insecticides contain sodium fluoride, which is much less toxic than fluoroacetate. [44] Insects fed 29-fluorostigmasterol use it to produce fluoroacetates. If a fluorine is transferred to a body cell, it blocks metabolism at the position occupied. [45]

Trifluralin was widely used in the 20th century, for example, in over half of U.S. cotton field acreage in 1998. [46] Because of its suspected carcinogenic properties some Northern European countries banned it in 1993. [47] As of 2015, the European Union has banned it, although Dow made a case to cancel the decision in 2011. [48]

Biochemistry

South Africa's gifblaar is one of the few organisms that naturally produce fluorine compounds Gifblaar.jpg
South Africa's gifblaar is one of the few organisms that naturally produce fluorine compounds

Biologically synthesized organofluorines are few in number, although some are widely produced. [49] [50] The most common example is fluoroacetate, with an active poison molecule identical to commercial "1080". It is used as a defense against herbivores by at least 40 green plants in Australia, Brazil, and Africa; [43] other biologically synthesized organofluorines include ω-fluoro fatty acids, fluoroacetone, and 2-fluorocitrate. [50] In bacteria, the enzyme adenosyl-fluoride synthase, which makes the carbon–fluorine bond, has been isolated. The discovery was touted as possibly leading to biological routes for organofluorine synthesis. [51]

Fluoride is considered a semi-essential element for humans: not necessary to sustain life, but contributing (within narrow limits of daily intake) to dental health and bone strength. Daily requirements for fluorine in humans vary with age and sex, ranging from 0.01 mg in infants below 6 months to 4 mg in adult males, with an upper tolerable limit of 0.7 mg in infants to 10 mg in adult males and females. [52] [53] Small amounts of fluoride may be beneficial for bone strength, but this is an issue only in the formulation of artificial diets. [54] (See also fluoride deficiency.)

Hazards

NFPA 704
fire diamond
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
4
0
4
W
The fire diamond hazard sign for elemental fluorine. [55]
The U.S. hazard signs for commercially transported fluorine DOT hazmat signs - Fluorine.svg
The U.S. hazard signs for commercially transported fluorine

Fluorine gas

Elemental fluorine is highly toxic. Above a concentration of 25 ppm, it causes significant irritation while attacking the eyes, airways and lungs and affecting the liver and kidneys. At a concentration of 100 ppm, human eyes and noses are seriously damaged. [57] People can be exposed to fluorine in the workplace by breathing it in, skin contact, or eye contact. The Occupational Safety and Health Administration (OSHA) has set the legal limit (Permissible exposure limit) for fluorine exposure in the workplace as 0.1 ppm (0.2 mg/m3) over an 8-hour workday. The National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 0.1 ppm (0.2 mg/m3) over an 8-hour workday. At levels of 25 ppm, fluorine is immediately dangerous to life and health. [58]

Hydrofluoric acid

Typical HF burns: the outward signs may not be evident for 24 hours, after which calcium treatments are less effective. HF burned hands.jpg
Typical HF burns: the outward signs may not be evident for 24 hours, after which calcium treatments are less effective.

Hydrofluoric acid, the water solution of hydrogen fluoride (HF), is a contact poison. Even though it is from a chemical perspective a relatively weak acid, it is far more dangerous than conventional strong mineral acids, such as nitric acid, sulfuric acid, or hydrochloric acid. Owing to its lesser chemical dissociation in water (remaining a neutral molecule), hydrogen fluoride penetrates tissue more quickly than typical acids. Poisoning can occur readily through the skin or eyes or when inhaled or swallowed. From 1984 to 1994, at least nine workers died in the United States from accidents with HF. [60]

Once in the blood, hydrogen fluoride reacts with calcium and magnesium, resulting in electrolyte imbalances, potentially including hypocalcemia. The consequent effect on the heart (cardiac arrhythmia) may be fatal. [60] Formation of insoluble calcium fluoride also causes severe pain. [61] Burns with areas larger than 160 cm2, about the size of a man's hand, can cause serious systemic toxicity. [62]

Symptoms of exposure to hydrofluoric acid may not be immediately evident, with an eight-hour delay for 50% HF and up to 24 hours for lower concentrations. Hydrogen fluoride interferes with nerve function, meaning that burns may not initially be painful. If the burn has been initially noticed, then HF should be washed off with a forceful stream of water for ten to fifteen minutes to prevent its further penetration into the body. Clothing used by the person burned may also present a danger. [63] Hydrofluoric acid exposure is often treated with calcium gluconate, a source of Ca2+ that binds with the fluoride ions. Skin burns can be treated with a water wash and 2.5 percent calcium gluconate gel [64] [65] or special rinsing solutions. [66] Because HF is absorbed, further medical treatment is necessary. Calcium gluconate may be injected or administered intravenously. Use of calcium chloride is contraindicated and may lead to severe complications. Sometimes surgical excision of tissue or amputation is required. [62] [67]

Fluoride ion

Moroccan cow with fluorosis, from industrial contamination Fluworoze egzostozes1-800h.jpg
Moroccan cow with fluorosis, from industrial contamination

Soluble fluorides are moderately toxic. For sodium fluoride, the lethal dose for adults is 5–10 g, which is equivalent to 32–64 mg of elemental fluoride per kilogram of body weight. [68] The dose that may lead to adverse health effects is about one fifth of the lethal dose. [69] Chronic excess fluoride consumption can lead to skeletal fluorosis, a disease of the bones that affects millions in Asia and Africa. [69] [70]

The fluoride ion is readily absorbed by the stomach and intestines. Ingested fluoride forms hydrofluoric acid in the stomach. In this form, fluoride crosses cell membranes and then binds with calcium and interferes with various enzymes. Fluoride is excreted through urine. Fluoride exposure limits are based on urine testing, which is used to determine the human body's capacity for ridding itself of fluoride. [69] [71]

Historically, most cases of fluoride poisoning have been caused by accidental ingestion of insecticides containing inorganic fluoride. [72] Most calls to poison control centers for possible fluoride poisoning come from the ingestion of fluoride-containing toothpaste. [69] Malfunction of water fluoridation equipment has occurred several times, including an Alaskan incident that sickened nearly 300 people and killed one. [73]

Biopersistence

Because of the strength of the carbon–fluorine bond, organofluorines endure in the environment. Perfluorinated compounds (PFCs) have attracted particular attention as persistent global contaminants. These compounds can enter the environment from their direct uses in waterproofing treatments and firefighting foams or indirectly from leaks from fluoropolymer production plants (where they are intermediates). Because of the acid group, PFCs are water-soluble in low concentrations. [74] While there are other PFAAs, the lion's share of environmental research has been done on the two most well-known: perfluorooctanesulfonic acid (PFOS) and perfluorooctanoic acid (PFOA). The U.S. Environmental Protection Agency classifies these materials as "emerging contaminants" based on the growing but still incomplete understanding of their environmental impact. [75] [76] [77]

Trace quantities of PFCs have been detected worldwide, in organisms from polar bears in the Arctic to the global human population. Both PFOS and PFOA have been detected in breast milk and the blood of newborns. A 2013 review showed widely varying amounts of PFOS and PFOA in different soils and groundwater, with no clear pattern of one chemical dominating. PFC concentrations were generally higher in areas with more human population or industrial activity, and areas with more PFOS generally also had more PFOA. [78] the two chemicals have been found at different concentrations in different populations; for example, one study showed more PFOS than PFOA in Germans, while another study showed the reverse for Americans. PFCs may be starting to decrease in the biosphere: one study indicated that PFOS levels in wildlife in Minnesota were decreasing, presumably because 3M discontinued its production. [75] [76]

The PFOS molecule PFOS-3D-vdW.png
The PFOS molecule

In the body, PFCs bind to proteins such as serum albumin. Their tissue distribution in humans is unknown, but studies in rats suggest it is present mostly in the liver, kidney, and blood. They are not metabolized by the body but are excreted by the kidneys. Dwell time in the body varies greatly by species. Rodents have half-lives of days, while in humans they remain for years. Many animals show sex differences in the ability to rid the body of PFAAs, but without a clear pattern. Gender differences of half lives vary by animal species. [75] [76] [79]

The potential health impact of PFCs is unclear. Unlike chlorinated hydrocarbons, PFCs are not lipophilic (stored in fat), nor genotoxic (damaging genes). Both PFOA and PFOS in high doses cause cancer and the death of newborns in rodents. Studies on humans have not been able to prove an impact at current exposures. Bottlenose dolphins have some of the highest PFOS concentrations of any wildlife studied; one study suggests an impact on their immune systems. [75] [76] [79]

The biochemical causes of toxicity are also unclear and may differ by molecule, health effect, and even animal. PPAR-alpha is a protein that interacts with PFAAs and is commonly implicated in contaminant-caused rodent cancers. [75] [76] [79]

Less fluorinated chemicals (i.e. not perfluorinated compounds) can also be detected in the environment. Because biological systems do not metabolize fluorinated molecules easily, fluorinated pharmaceuticals like antibiotics and antidepressants can be found in treated city sewage and wastewater. [80] Fluorine-containing agrichemicals are measurable in farmland runoff and nearby rivers. [81]

See also

Related Research Articles

<span class="mw-page-title-main">Fluorocarbon</span> Class of chemical compounds

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 commercial polymers, refrigerants, drugs, and anesthetics.

Fluoride is an inorganic, monatomic anion of fluorine, with the chemical formula F−
, whose salts are typically white or colorless. Fluoride salts typically have distinctive bitter tastes, and are odorless. Its salts and minerals are important chemical reagents and industrial chemicals, mainly used in the production of hydrogen fluoride for fluorocarbons. Fluoride is classified as a weak base since it only partially associates in solution, but concentrated fluoride is corrosive and can attack the skin.

<span class="mw-page-title-main">Hydrofluoric acid</span> Solution of hydrogen fluoride in water

Hydrofluoric acid is a solution of hydrogen fluoride (HF) in water. Solutions of HF are colorless, acidic and highly corrosive. It is used to make most fluorine-containing compounds; examples include the commonly used pharmaceutical antidepressant medication fluoxetine (Prozac) and the material PTFE (Teflon). Elemental fluorine is produced from it. It is commonly used to etch glass and silicon wafers.

<span class="mw-page-title-main">Perfluorooctanoic acid</span> Perfluorinated carboxylic acid

Perfluorooctanoic acid is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes and as a material feedstock. PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure, which consists of a perfluorinated, n-heptyl "tail group" and a carboxylate "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic.

<span class="mw-page-title-main">Perfluorooctanesulfonic acid</span> Fluorosurfactant and persistent organic pollutant

Perfluorooctanesulfonic acid (PFOS) 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-made) fluorosurfactant, now regarded as a global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and related stain repellents. The acronym "PFOS" refers to the parent sulfonic acid and to various salts of perfluorooctanesulfonate. These are all colorless or white, water-soluble solids. Although of low acute toxicity, PFOS has attracted much attention for its pervasiveness and environmental impact. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009.

Fluoride toxicity is a condition in which there are elevated levels of the fluoride ion in the body. Although fluoride is safe for dental health at low concentrations, sustained consumption of large amounts of soluble fluoride salts is dangerous. Referring to a common salt of fluoride, sodium fluoride (NaF), the lethal dose for most adult humans is estimated at 5 to 10 g. Ingestion of fluoride can produce gastrointestinal discomfort at doses at least 15 to 20 times lower than lethal doses. Although it is helpful topically for dental health in low dosage, chronic ingestion of fluoride in large amounts interferes with bone formation. In this way, the most widespread examples of fluoride poisoning arise from consumption of ground water that is abnormally fluoride-rich.

<span class="mw-page-title-main">Sodium fluoride</span> Ionic compound (NaF)

Sodium fluoride (NaF) is an inorganic compound with the formula NaF. It is a colorless or white solid that is readily soluble in water. It is used in trace amounts in the fluoridation of drinking water to prevent tooth decay, and in toothpastes and topical pharmaceuticals for the same purpose. In 2020, it was the 265th most commonly prescribed medication in the United States, with more than 1 million prescriptions. It is also used in metallurgy and in medical imaging.

<span class="mw-page-title-main">Bromine pentafluoride</span> Chemical compound

Bromine pentafluoride, BrF5, is an interhalogen compound and a fluoride of bromine. It is a strong fluorinating agent.

<span class="mw-page-title-main">Hydrogen fluoride</span> Chemical compound

Hydrogen fluoride (fluorane) is an inorganic compound with chemical formula HF. It is a very poisonous, colorless gas or liquid that dissolves in water to yield an aqueous solution termed hydrofluoric acid. It is the principal industrial source of fluorine, often in the form of hydrofluoric acid, and is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is also widely used in the petrochemical industry as a component of superacids. Due to strong and extensive hydrogen bonding, it boils at near room temperature, much higher than other hydrogen halides.

<span class="mw-page-title-main">Microwave popcorn</span> Type of convenience food

Microwave popcorn is a convenience food consisting of unpopped popcorn in an enhanced, sealed paper bag intended to be heated in a microwave oven. In addition to the dried corn, the bags typically contain cooking oil with sufficient saturated fat to solidify at room temperature, one or more seasonings, and natural or artificial flavorings or both. With the many different flavors, there are many different providers.

Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.

<span class="mw-page-title-main">Fluorine</span> Chemical element, symbol F and atomic number 9

Fluorine is a chemical element; it has symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reactive, as it reacts with all other elements except for the light inert gases.

Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also an environmental contaminant found in people and wildlife along with PFOS and PFOA.

<span class="mw-page-title-main">Per- and polyfluoroalkyl substances</span> Class of perfluorinated chemical compounds

Per- and polyfluoroalkyl substances (PFAS or PFASs) are a group of 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 moiety, –CnF2n+1–. Beginning in 2021, the Organisation for Economic Co-operation and Development (OECD) expanded their terminology, stating that "PFASs are defined as fluorinated substances that contain at least one fully fluorinated methyl or methylene carbon atom (without any H/Cl/Br/I atom attached to it), i.e., with a few noted exceptions, any chemical with at least a perfluorinated methyl group (–CF3) or a perfluorinated methylene group (–CF2–) is a PFAS."

<span class="mw-page-title-main">Perfluorinated compound</span>

A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound lacking C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method for their production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.

<span class="mw-page-title-main">Perfluorooctanesulfonyl fluoride</span> Chemical compound

Perfluorooctanesulfonyl fluoride (POSF) is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.

Fluorine forms a great variety of chemical compounds, within which it always adopts an oxidation state of −1. With other atoms, fluorine forms either polar covalent bonds or ionic bonds. Most frequently, covalent bonds involving fluorine atoms are single bonds, although at least two examples of a higher order bond exist. Fluoride may act as a bridging ligand between two metals in some complex molecules. Molecules containing fluorine may also exhibit hydrogen bonding. Fluorine's chemistry includes inorganic compounds formed with hydrogen, metals, nonmetals, and even noble gases; as well as a diverse set of organic compounds. For many elements the highest known oxidation state can be achieved in a fluoride. For some elements this is achieved exclusively in a fluoride, for others exclusively in an oxide; and for still others the highest oxidation states of oxides and fluorides are always equal.

<span class="mw-page-title-main">Fluorochemical industry</span> Industry dealing with chemicals from fluorine

The global market for chemicals from fluorine was about US$16 billion per year as of 2006. The industry was predicted to reach 2.6 million metric tons per year by 2015. The largest market is the United States. Western Europe is the second largest. Asia Pacific is the fastest growing region of production. China in particular has experienced significant growth as a fluorochemical market and is becoming a producer of them as well. Fluorite mining was estimated in 2003 to be a $550 million industry, extracting 4.5 million tons per year.

<span class="mw-page-title-main">Hydrofluoric acid burn</span> Medical condition

A hydrofluoric acid burn is a chemical burn from hydrofluoric acid. Where it contacts the skin it results in significant pain, swelling, redness, and skin breakdown. If the fumes are breathed in swelling of the upper airway and bleeding may occur. Complications can include electrolyte, heart, lung, kidney, and neurological problems.

<span class="mw-page-title-main">Perfluorohexanesulfonic acid</span> Chemical compound

Perfluorohexanesulfonic acid (PFHxS) is a synthetic chemical compound. It is one of many compounds collectively known as per- and polyfluoroalkyl substances (PFASs). It is an anionic fluorosurfactant and a persistent organic pollutant with bioaccumulative properties. Although the use of products containing PFHxS and other PFASs 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.

References

  1. ↑ G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, B. McKusick "Fluorine Compounds, Organic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a11_349
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