Some important fluorocarbons.
A: fluoromethane
B: isoflurane
C: a CFC
D: an HFC
E: triflic acid
F: Teflon
G: PFOS
H: fluorouracil
I: Prozac

Fluorocarbons are chemical compounds that contain carbon-fluorine bonds. The relatively low reactivity and high polarity of the carbon-fluorine bond imparts unique characteristics to fluorocarbons. Fluorocarbons tend to be only slowly broken down in the environment and therefore many are considered persistent organic pollutants. Many commercially useful fluorocarbons also contain hydrogen, chlorine, or bromine. Image File history File links Download high-resolution version (292x2000, 366 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Fluorocarbon ... Image File history File links Download high-resolution version (292x2000, 366 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Fluorocarbon ... Fluoromethane, also known as methyl fluoride, Freon 41 and HFC-41, is a toxic, liquefiable, and flammable gas at standard temperature and pressure. ... Structural formula of isoflurane Isoflurane (1-chloro-2,2,2-trifluoroethyl difluoromethyl ether) is a halogenated ether used for inhalation anesthesia. ... Disclaimer and references Dichlorodifluoromethane (R-12), usually sold under the brand name Freon-12, is a chlorofluorocarbon halomethane used as a refrigerant and aerosol spray propellant until its manufacture was discontinued in 1995, due to concerns about damage to the ozone layer. ... 1,1,1,2-Tetrafluoroethane, also called simply tetrafluoroethane, R-134a or HFC-134a, is a refrigerant without an ozone depletion potential and thermodynamic properties similar to R-12 (dichlorodifluoromethane). ... Trifluoromethanesulfonic acid, also known as triflic acid or TfOH, is a sulfonic acid with the chemical formula CF3SO3H . ... Teflon is polytetrafluoroethylene (PTFE), a polymer of fluorinated ethylene. ... Perfluorooctanoic acid (PFOA) is an artificial acid that has many industrial uses. ... Fluorouracil (5-FU) is a drug that is used in the treatment of cancer. ... Fluoxetine hydrochloride is an antidepressant drug used medically in the treatment of depression, body dysmorphic disorder, obsessive-compulsive disorder, bulimia nervosa, premenstrual dysphoric disorder, hypochondriasis and panic disorder. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... A chemical bond is the physical phenomenon (or phenomena) responsible for the attractive interactions between atoms that confers stability to di- and polyatomic chemical compounds. ... Persistent organic pollutants (POPs) are a class of chemicals that persist in the environment, are capable of long-range transport, bioaccumulate in human and animal tissue, and have significant impacts on human health and the environment. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ...

Classes of fluorocarbons

Chlorofluorocarbons and hydrofluorocarbons

Main article: haloalkane

Chlorofluorocarbons (CFCs) are fluorocarbons that also contain chlorine atoms. They were formerly used widely in industry as refrigerants, propellants, and cleaning solvents (see also: uses. Dichlorodifluoromethane and chlorodifluoromethane were among the most widely used refrigerants. However, CFCs generally have potent ozone-depleting potential primarily due to homolytic cleavage of the carbon-chlorine bonds. Their use has now been mostly prohibited by the Montreal Protocol. The haloalkane (also known as halogenoalkanes) are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... A refrigerant is a compound used in a heat cycle that undergoes a phase change from a gas to a liquid and back. ... A propellant is a material that is used to move an object by applying a motive force. ... Some important fluorocarbons. ... Disclaimer and references Dichlorodifluoromethane (R-12), usually sold under the brand name Freon-12, is a chlorofluorocarbon halomethane used as a refrigerant and aerosol spray propellant until its manufacture was discontinued in 1995, due to concerns about damage to the ozone layer. ... Cl | F--C--F | H Chlorodifluoromethane or difluoromonochloromethane is a hydrochlorofluorocarbon (HCFC) with chemical formula CHClF2 and CAS number 75-45-6. ... The ozone layer, or ozonosphere layer (very rarely used term), is the part of the Earths atmosphere which contains relatively high concentrations of ozone (O3). ... In chemistry, homolysis is chemical bond dissociation of a neutral molecule generating two free radicals. ... The Montreal Protocol on Substances That Deplete the Ozone Layer is an international treaty designed to protect the ozone layer by phasing out the production of a number of substances believed to be responsible for ozone depletion. ...

Hydrofluorocarbons (HFCs) are hydrocarbons in which some, but not all, of the hydrogen atoms have been replaced with fluorine. The fluorine atoms in these compounds do not catalyse ozone destruction, therefore HFCs do not damage the ozone layer. Consequently, HFCs such as tetrafluoroethane have become favored replacements for CFCs. Tetrafluoroethane (CH2FCF3, technically 1,1,1,2-Tetrafluoroethane) is an inert gas found in cans of air used for blow-dusting computers and other miscellaneous items that are hard to reach or access. ...

Fluoropolymers

Main article: fluoropolymer

Fluorocarbon polymers are also well-known. These polymers are tough, chemical inert, and electrically insulating. The most famous example is DuPont's Teflon, a polymer of the monomer tetrafluoroethylene. Other important polymers include polyvinylidene fluoride ([CH₂CF₂]_n) and polychlorotrifluoroethylene ([CFClCF₂]_n or PCTFE, or Kel-F). A fluoropolymer is a polymer that contains atoms of fluorine. ... Polymer is a term used to describe large molecules consisting of repeating structural units, or monomers, connected by covalent chemical bonds. ... Teflon is polytetrafluoroethylene (PTFE), a polymer of fluorinated ethylene. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Tetrafluoroethylene, or tetrafluoroethene, C2F4, is a compound of carbon and fluorine. ... PVDF, or PolyVinylidine DiFluoride, is a highly non-reactive and pure thermoplastic fluoropolymer. ...

Uses

Anesthetics

Main article: anesthetic

Many volatile anesthetics used to render surgical patients unconscious are fluorocarbons, such as methoxyflurane, enflurane, isoflurane, sevoflurane and desflurane. The fluorine atoms reduce their flammability compared to the non-fluorinated anesthetics originally used, such as diethyl ether and cyclopropane, which are dangerously flammable. Anesthesia (AE), also anaesthesia (BE), is the process of blocking the perception of pain and other sensations. ... The volatile anaesthetics are a class of general anaesthetic drugs. ... Methoxyflurane (C3H4Cl2F2O) is an inhalation anesthetic used in the 1960s, but withdrawn because of detrimental effects on the kidneys. ... Structural formula of enflurane Enflurane (2-chloro-1,1,2,-trifluoroethyl-difluomethyl ether) is a halogenated ether that was commonly used for inhalational anesthesia during the 1970s and 1980s. ... Structural formula of isoflurane Isoflurane (1-chloro-2,2,2-trifluoroethyl difluoromethyl ether) is a halogenated ether used for inhalation anesthesia. ... Sevoflurane (2, 2, 2-trifluoro-1-(trifluoromethyl) ethyl ether), also called fluoromethyl, is a halogenated ether used for induction and maintenance of general anesthesia. ... Desflurane is a highly flourinated ether used for maintenance of general anaesthesia. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ...

Refrigerants

Main article: refrigerant

Some fluorocarbons (e.g. Freon) have been used as refrigerants. These fluorocarbons combine good thermodynamic properties (they have boiling points somewhat below typical target temperatures, a high heat of vaporization, a moderate density in liquid form and a high density in the gas phase) with a safe (low toxicity and flammability) and noncorrosive nature. Because of their negative effect on the ozone layer, many fluorocarbons have been banned as refrigerant after the Montreal Protocol. A refrigerant is a compound used in a heat cycle that undergoes a phase change from a gas to a liquid and back. ... Freon is a trade name for a group of chlorofluorocarbons used primarily as a refrigerant. ... A refrigerant is a compound used in a heat cycle that undergoes a phase change from a gas to a liquid and back. ... The ozone layer, or ozonosphere layer (very rarely used term), is the part of the Earths atmosphere which contains relatively high concentrations of ozone (O3). ... The Montreal Protocol on Substances That Deplete the Ozone Layer is an international treaty designed to protect the ozone layer by phasing out the production of a number of substances believed to be responsible for ozone depletion. ...

Propellants

Main article: aerosol spray

Compounds that have a boiling point just around room temperature, with a high vapour pressure can be used as propellant gas. Some fluorocarbons have these properties, and, before the Montreal Protocol, many of these low boiling fluorocarbons were used as propellants. Aerosol spray can Aerosol spray is the name given to type of spray can with what one might call Aerosol in it. ... The Montreal Protocol on Substances That Deplete the Ozone Layer is an international treaty designed to protect the ozone layer by phasing out the production of a number of substances believed to be responsible for ozone depletion. ... A propellant is a material that is used to move an object by applying a motive force. ...

Solvents

Flurocarbons are used as industrial solvents due to their specific properties, including: non-flammability, stability, excellent dielectric properties, low surface tension and viscosity, very low toxicity and a favourable environmental profile. A symbol for flammable chemicals Flammability is the ease with which a substance will ignite, causing fire or combustion. ... A dielectric, or electrical insulator, is a substance that is highly resistant to electric current. ... In physics, surface tension is an effect within the surface layer of a liquid that causes that layer to behave as an elastic sheet. ... The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... // Toxic and Intoxicated redirect here – toxic has other uses, which can be found at Toxicity (disambiguation); for the state of being intoxicated by alcohol see Drunkenness. ...

Prior to the Montreal Protocol, CFCs, such as Freon and chlorodifluoromethane were used as cleaning solvents. Also HFCs were developed with similar properties. Quite often these HFC's are blended with other fluids to obtain tailored properties for specific application.

Main applications are:

• Precision Cleaning (Degreasing)
• Electronic Assemblies Defluxing
• Particulate Removal
• Drying after Aqueous Cleaning
• as a Carrier Fluid
• as a Dielectric Coolant

HFCs, particularly 1,1,1,2-tetrafluoroethane, are used for specialist extraction of extremely important natural products; such as Taxol for cancer treatment from yew needles, evening primrose oil food supplement, and vanilla. The use of 1,1,1,2-tetrafluroethane compliments other methods of extraction, in being highly selective and allowing high quality and high yield extractions.^[1] 1,1,1,2-Tetrafluoroethane, also called simply tetrafluoroethane, R-134a or HFC-134a, is a refrigerant without an ozone depletion potential and thermodynamic properties similar to R-12 (dichlorodifluoromethane). ... Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their solution preferences for two different immiscible liquids, usually water and an organic solvent. ... -1... Paclitaxel is a drug used in the treatment of cancer. ... Species Taxus baccata - European Yew Taxus brevifolia - Pacific Yew Taxus canadensis - Canadian Yew Taxus chinensis - Chinese Yew Taxus cuspidata - Japanese Yew Taxus floridana - Florida Yew Taxus globosa - Mexican Yew Taxus sumatrana - Sumatran Yew Taxus wallichiana - Himalayan Yew Yews are small coniferous trees or shrubs in the genus Taxus in the... Species Oenothera biennis Oenothera fruticosa Oenothera speciosa et al Oenothera is a genus of about 125 species of annual, biennial and perennial herbs. ... For other uses, see vanilla (disambiguation). ...

Lubrication

Fluorocarbons are unreactive and are often used for demanding applications. Also, solid fluoropolymers have a low coefficient of friction, while fluid fluoropolymers can act as lubricants. The resistance to lateral motion when one attempts to slide the surface of one object over another surface is called friction or traction. ...

Teflon and other similar fluoropolymers are applied as layers to help reduce friction. Small, self-lubricated parts such as stopcocks for laboratory glassware may be entirely made of Teflon. Teflon is polytetrafluoroethylene (PTFE), a polymer of fluorinated ethylene. ... Friction is the force that opposes the relative motion or tendency of such motion of two surfaces in contact. ... A stopcock is a valve used to restrict or isolate the flow through a pipe of a liquid or gas. ... Brown glass jars with some clear lab glassware in the background Laboratory glassware refers to a variety of equipment, traditionally made of glass, used for scientific experiments and other work in science, especially in chemistry and biology laboratories. ... Teflon is polytetrafluoroethylene (PTFE), a polymer of fluorinated ethylene. ...

Fluorocarbon based greases are sometimes used in demanding applications. Advantages include low reactivity. Examples include Krytox by DuPont. Krytox is a trademark of a family of high performance synthetic lubricants (oils and greases) used in many things from spaceships to computer chips. ... This article is about the DuPont company. ...

Also used in certain firearm lubricants such as "Tetra Gun"

Water repellant and stain repellant products

In general, highly fluorinated organic compounds are hydrophobic and have water-repellant and stain-repellant properties. The original formulations of products such as Scotchgard contained fluorocarbons including perfluorobutane sulfonate and perfluorooctane sulfonate (PFOS). But many of these uses have been phased out due to environmental concerns, such as those associated with perfluorooctanoic acid, an intermediate in the manufacture of PFOS. Similarly, products containing Gore-Tex and Teflon are made from fluoropolymers. In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ... Scotchgard is a 3M brand of products used to protect fabric, furniture, and carpets. ... Perfluorooctanoic acid (PFOA) is an artificial acid that has many industrial uses. ... Perfluorooctanoic acid (PFOA), also known as C8, is an artificial acid that has many industrial uses. ... Gore-Tex membrane, electron microphotograph Gore-Tex (abbreviated GTX) is a registered trademark of W.L. Gore & Associates best known for its use in relation to waterproof/breathable fabrics. ... Teflon is polytetrafluoroethylene (PTFE), a polymer of fluorinated ethylene. ...

Fluorocarbons are also used in fishing line, in myriad precision plastics applications, and in highly precise lubrication applications.

Chemical reagents

Triflic acid (CF₃SO₃H) and trifluoroacetic acid (CF₃CO₂H) are important reagents in organic synthesis. They are valuable for their properties as very strong acids that are soluble in organic solvents. The electronegative nature of the fluorine atoms stabilizes the dissociated anions of triflic acid and trifluoroacetic acid, leading to stronger acidity compared to their unfluorinated analogs, methanesulfonic acid and acetic acid, respectively. The fluorine atoms also enhance the thermal and chemical stabilities of the conjugate bases. In fact, the polymeric analogue of triflic acid, nafion is used as a proton-exchange material in fuel cells. Triflate, more formally known as trifluoromethanesulfonate, has the structure CF3SO3-. It is an extremely stable polyatomic ion, being the conjugate base of triflic acid (CF3SO3H), one of the strongest acids known and a super acid. ... Trifluoroacetic acid (TFA) is a strong, hygroscopic, non-oxidizing, organic acid with a molecular formula C2HF3O2. ... Organic synthesis is the construction of organic molecules via chemical processes. ... For other uses, see Solvent (disambiguation). ... It has been suggested that Sulfonic acid/Temp be merged into this article or section. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... In the field of chemistry, in the Brønsted-Lowry (protonic) theory of acids and bases, a conjugate base is the basic member, X-, of a pair of compounds that differ only by the presence or absence of a proton at a certain position. ... Nafion® is a sulfonated tetrafluorethylene copolymer developed in the late 1960s by DuPont. ... A fuel cell is an electrochemical device similar to a battery, but differing from the latter in that it is designed for continuous replenishment of the reactants consumed; i. ...

The triflate-group (the conjugate base of the triflic acid) is a good leaving group in organic chemistry. A leaving group is an atom or molecule that detaches from an organic molecule, which, after detachment, is called the residual or main part. ...

Carbon-fluorine bonds have found application in non-coordinating anions. In these anions (e.g. BF₄^-, PF₆^-, B(C₆H₃(CF₃)₂)₄^-, and B(C₆F₅)₄^- the charge is 'smeared' out over many electronegative atoms. In chemistry, a non-coordinating anion is an anion that only weakly interacts with its cation. ...

Pollution effects

Main article: pollution

Main article: Ozone depletion

As mentioned above, chlorofluorocarbons have been criticized for their harm to the ozone layer. It is estimated that a single CFC molecule has the ability to decompose approximately 100,000 ozone molecules.^[2] Pollution is the release of environmental contaminants. ... Bold textItalic textRecent Developement 35 million dollar prize is now being offerred by a private agency to anybody who can propose a successful solution to the Ozone depletion problem Global monthly average total ozone amount The term ozone depletion is used to describe two distinct but related observations: a slow...

Biological role

Although there are thousands of known naturally-occurring organic compounds containing chlorine and bromine, there are only a handful of natural fluorocarbons.^[3] They have been found in microorganisms and plants, but not animals. The most common natural fluorocarbon is fluoroacetic acid, a potent toxin found in a few species of plants. Others included ω-fluoro fatty acids, fluoroacetone, and 2-fluorocitrate which are all believed to be biosynthesized from fluoroacetic acid. A space-filling model of sodium fluoroacetate 1080 is the commonly used name for sodium fluoroacetate (also known as sodium monofluoroacetate), a potent metabolic poison used primarily to control mammalian pests. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ...

Since the C-F bond is generally metabolically stable and fluorine is considered a bioisostere of the hydrogen atom, many pharmaceuticals contain C-F bonds. An example of this is fluorinated uracil. When elemental fluorine is reacted with uracil, 5-fluorouracil is produced. The resulting compound is an anticancer drug (antimetabolite) used to masquerade as uracil during the nucleic acid replication process.^[4] This can lead to the incorporation of 5-fluorouracil into DNA and RNA as well as inhibition of the enzymes that are responsible for the synthesis of the normal components of DNA. These factors can be toxic to cancer cells that need to rapidly produce normal nucleic acids in order to continue growing.^[5] In medicinal chemistry, bioisosteres are substituents or groups with similar physical or chemical properties that impart similar biological properties to a chemical compound. ... Uracil is a pyrimidine which is common and naturally occurring. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... Fluorouracil (5-FU) is a drug that is used in the treatment of cancer. ... An antimetabolite is a chemical with a similar structural to a substance (a metabolite) required for normal biochemical reactions, yet different enough to interfere with the normal functions of cells, including cell division. ... Look up Masquerade in Wiktionary, the free dictionary. ... The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of nucleotide monomers. ...

Well known pharmaceutical drugs incorporating fluorine include fluoxetine (Prozac), paroxetine (Paxil), ciprofloxacin (Cipro), mefloquine, fluconazole, and many more. Fluoxetine hydrochloride is an antidepressant drug used medically in the treatment of depression, body dysmorphic disorder, obsessive-compulsive disorder, bulimia nervosa, premenstrual dysphoric disorder, hypochondriasis and panic disorder. ... Paroxetine or paroxetine hydrochloride is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Ciprofloxacin is the generic international name for the synthetic antibiotic manufactured and sold by Bayer Pharmaceutical under the brand names Cipro and Ciproxin (and other brand names in other markets, e. ... Mefloquine is an orally administered antimalarial drug used as a prophylaxis against and treatment for malaria. ... Fluconazole (INN) (IPA: ) is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. ...

Chemical properties

The carbon-fluorine bond length is typically about 1.4 Å (1.39 Å in fluoromethane). This is shorter than any other carbon-halogen bond, and comparable in length to a carbon-hydrogen bond. Since fluorine is a very electronegative atom (much more so than carbon), the carbon-fluorine bond has a significant dipole moment. The carbon-fluorine bond is stronger than other carbon-halogen bonds. The bond dissociation energy is 552 kJ/mol for carbon-fluorine compared to 397, 288, 209 kJ/mol for bonds between carbon and chlorine, bromine and iodine, respectively.^[6] The strength of the carbon-fluorine bond is also significantly stronger than the carbon-hydrogen bond, which is only 338 kJ/mol. Fluoromethane, also known as methyl fluoride, Freon 41 and HFC-41, is a toxic, liquefiable, and flammable gas at standard temperature and pressure. ... It has been suggested that this article or section be merged with electronegativity. ... This article is about the electromagnetic phenomenon. ... The halogens are a chemical series of nonmetals. ... In chemistry, bond dissociation energy, D0, is one measure of the bond strength in a chemical bond. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ...

As a result of these unique features of the carbon-fluorine bond, an overarching theme in fluorocarbon chemistry is the contrasting set of physical and chemical properties in comparison to the corresponding hydrocarbons. Case studies follow.

Pentakis(trifluoromethyl)cyclopentadiene

Pentakis(trifluoromethyl)cyclopentadiene (C₅(CF₃)₅H) is a strong acid, with a pK_a = −2. Its high acidity and robustness is indicated by the fact that this compound is typically purified by distillation from H₂SO₄. In contrast, C₅(CH₃)₅H requires a strong base such as butyllithium for deprotonation, as is typical for a hydrocarbon.^[7] This compound is prepared in a multistep, one-pot reaction of potassium fluoride (KF) with 1,1,2,3,4,4-hexachlorobutadiene. An acid (often represented by the generic formula HA) is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a pH of less than 7. ... Laboratory distillation set-up using, without a fractionating column 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... 1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diolefin with the formula C5Me5H (Me = CH3). ... A base in chemistry is a chemical substance which has a free pair of electrons to bind a hydrogen ion commonly referred to as a proton (IUPAC definition). ... An organolithium reagent is a carbon nucleophile similar to a Grignard reagent. ... The chemical compound potassium fluoride (KF) is a metal halide composed of potassium and fluoride. ...

Hexafluoroacetone and its imine

The molecule hexafluoroacetone ((CF₃)₂CO), the fluoro-analogue of acetone, has a boiling point of −27 °C compared to +55 °C for acetone itself. This difference illustrates one of the remarkable effects of replacing C-H bonds with C-F bonds. Normally, the replacement of H atoms with heavier halogens results in elevated boiling points due to increased van der Waals interactions between molecules. Further demonstrating the remarkable effects of fluorination, (CF₃)₂CO forms a stable, distillable hydrate,^[8] (CF₃)₂C(OH)₂. Ketones rarely form stable hydrates. Continuing this trend, (CF₃)₂CO adds ammonia to give (CF₃)₂C(OH)(NH₂) which can be dehydrated with POCl₃ to give (CF₃)₂CNH.^[9] Compounds of the type R₂C=NH are otherwise quite rare. Hexafluoroacetone is an organic compound with the formula CF3-CO-CF3. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... In chemistry, the term van der Waals force originally referred to all forms of intermolecular forces; however, in modern usage it tends to refer to intermolecular forces that deal with forces due to the polarization of molecules. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ...

Methods for preparation of fluorocarbons

Since fluorocarbons very rarely occur naturally, they must be prepared using synthetic chemistry. Some methods include:

• Direct fluorination of hydrocarbons with F₂, often highly diluted with N₂.

R₃CH + F₂ → R₃CF + HF

Such reactions are important preparatively but require care because hydrocarbons can uncontrollably "burn" in F₂, analogous to the combustion of hydrocarbon in O₂. For example, butane burns in an atmosphere of fluorine. Combustion or burning is a complex sequence of chemical reactions between a fuel and an oxidant accompanied by the production of heat or both heat and light in the form of either a glow or flames. ...

C₄H₉ + 12.5 F₂ → 4 CF₄ + 9 HF

• Metathesis reactions employing alkali metal fluorides.

R₃CCl + MF → R₃CF + MCl (M = Na, K, Cs)

• From preformed fluorinated reagents. Many fluorinated building blocks are available: CF₃X (X = Br, I), C₆F₅Br, and C₃F₇I. These species form Grignard reagents that then can be treated with a variety of electrophiles.^[10]
• Decomposition of aryldiazonium tetrafluoroborates in the Sandmeyer reaction^[11] or Schiemann reaction:

ArN₂BF₄ → ArF + N₂ + BF₃

• Nucleophilic displacement of hydroxyl and carbonyl groups by so-called deoxofluorination agents. One method of fluoride for oxide exchange in carbonyl compounds is with sulfur tetrafluoride:

RCO₂H + SF₄ → RCF₃ + SO₂ + HF

DAST stands for dialkylaminosulfur trifluoride (NEt₂SF₃) but easily combustible above 90°C. A safer alternative is bis(2-methoxyethyl)aminosulfur trifluoride or deoxo-fluor:^[12]

Metathesis is a sound change that alters the order of phonemes in a word. ... The alkali metals are the series of elements in Group 1 (IUPAC style) of the periodic table (excluding hydrogen in all but one rare circumstance): lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), and francium (Fr). ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. ... The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts. ... The Schiemann reaction (also called the Balz-Schiemann reaction) is a chemical reaction in which anilines (1) are transformed to aryl fluorides (3) via diazonium fluoroborates (2). ... In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... Sulfur tetrafluoride is SF4. ... Sulfur tetrafluoride is SF4. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Image File history File links Download high-resolution version (971x291, 5 KB) Deoxo-Fluor_application I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ...

References

1. ^ Flurocarbons and Sulphur Hexafluoride, maintained by European Fluorocarbons Technical Committee (EFCTC)
2. ^ http://www.bom.gov.au/lam/Students_Teachers/ozanim/ozoanim.shtml
3. ^ D.B. Harper and D. O'Hagan. The Fluorinated Natural Products. Natural Product Reports, 1994, 123-133.
4. ^ Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997.
5. ^ Soong, Richiea and Diasio, Robert B. "Advances and challenges in fluoropyrimidine pharmacogenomics and pharmacogenetics." Pharmacogenomics 6(8): 835-847, December 2005.
6. ^ Webelements
7. ^ R. D. Chambers, A. J. Roche, J. F.S. Vaughan "Direct syntheses of Pentakis(trifluoromethyl)cyclopentadienide Salts and Related Systems" Canadian Journal of Chemistry volume 74, pages 1925-1929 (1996).
8. ^ Van Der Puy, M. ; Anello, L. G. “Hexafluoroacetone” Organic Syntheses, Collective Volume 7, page 251
9. ^ Middleton, W. J.; Carlson, H. D. "Hexafluoroacetoneimine" Organic Syntheses Collective Volume 6, page 664
10. ^ Crombie, A.; Kim, S.-Y.; Hadida, S; Curran, and D. P. “Synthesis of Tris(2-Perfluorohexylethyl)tin Hydride: A Highly Fluorinated Tin Hydride with Advantageous Features of Easy Purification” Organic Syntheses Collective Volume 10, page 712
11. ^ Flood, D. T. “Fluorobenzene” Organic Syntheses Collective Volume 2, page 295
12. ^ Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum deoxofluorinating agent with enhanced thermal stability Gauri S. Lal, Guido P. Pez, Reno J. Pesaresi and Frank M. Prozonic Chem. Commun., 1999, 215 - 216, DOI:10.1039/a808517j

Chemical Communications or ChemComm is a is a peer-reviewed scientific journal in the chemical sciences published since 1996 by the Royal Society of Chemistry. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• CFCs and Ozone Depletion Freeview video provided by the Vega Science Trust.

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