Perfluoroether

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Perfluoroethers are a class of organofluorine compound containing one or more ether functional group. In general these compounds are structurally analogous to the related hydrocarbon ethers, except for the distinctive properties of fluorocarbons.

Contents

The introduction of an ether function to a perfluoro-polymer chain also provides thermoplastic properties to the polymer, making thermal forming possible. This is a great technological advantage for producing a large variety of shapes (e.g., beakers, funnels, flasks for laboratory uses, etc...) and allows extrusion of highly chemically-resistant tubing. It also confers on the polymer a translucent appearance. [1]

Low molecular weight fluorinated ethers

PFA tubing is commonly used to handle aggressive chemicals Pfa tubing.jpeg
PFA tubing is commonly used to handle aggressive chemicals
Nafion is a fluoroether with strongly acidic sulfonic acid substituents Nafion2.svg
Nafion is a fluoroether with strongly acidic sulfonic acid substituents

Acyclic perfluoroethers are analogues of diethylether, e.g. O(C2F5)2, such perfluoro(2-ethoxyethane)sulfonic acid (PFEESA).

More interesting and more useful are the cyclic ethers, especially, the epoxides. Tetrafluoroethyene oxide and hexafluoropropylene oxide are two of the simplest cyclic perfluoroethers. These are precursors of perfluoro(methyl vinyl ether) (CF2=CFOCF3) and perfluoro(propyl vinyl ether), and are used as comonomers with tetrafluoroethylene.

Polymeric perfluoroethers

Perfluoroalkoxy alkanes (PFAs) are fluoropolymers with properties similar to polytetrafluoroethylene (PTFE). Methylfluoroalkoxy (MFA) is a polytetrafluoroethylene perfluoro methylvinylether prepared with a different ratio of PTFE and MVE monomers to that used for PFA. In these materials, the ether groups are pendant from the polymer backbone.

Krytox is a grease generated by the polymerization of hexafluoropropylene oxide. Its chemical formula is F−(CF(CF3)−CF2−O)n−CF2CF3. The ether groups are integral to the polymer chain. [2]

Nafion is a perfluorinated polyether with pendant sulfonic acid groups (RSO3H).

Precautions

At high temperatures or in a fire, perfluoroethers decompose and may release hydrogen fluoride. Any residue must be handled using protective equipment.

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Polytetrafluoroethylene</span> Synthetic polymer

Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene and is a PFAS that has numerous applications. The commonly known brand name of PTFE-based composition is Teflon by Chemours, a spin-off from DuPont, which originally discovered the compound in 1938.

<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.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

<span class="mw-page-title-main">Nafion</span> Brand name for a chemical product

Nafion is a brand name for a sulfonated tetrafluoroethylene based fluoropolymer-copolymer discovered in the late 1960s by Dr. Walther Grot of DuPont. Nafion is a brand of the Chemours company. It is the first of a class of synthetic polymers with ionic properties that are called ionomers. Nafion's unique ionic properties are a result of incorporating perfluorovinyl ether groups terminated with sulfonate groups onto a tetrafluoroethylene (PTFE) backbone. Nafion has received a considerable amount of attention as a proton conductor for proton exchange membrane (PEM) fuel cells because of its excellent chemical and mechanical stability in the harsh conditions of this application.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

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

Krytox is a registered trademark of The Chemours Company. It refers to a group of colourless synthetic lubricants (oils and greases) with a variety of applications. Invented by researchers at DuPont, Krytox oils are fluorocarbon ether polymers of polyhexafluoropropylene oxide, with a chemical formula: F−(CF(CF3)−CF2−O)n−CF2CF3, where the degree of polymerization, n, generally lies within the range of 10 to 60. These compounds are collectively known by many names including perfluoropolyether (PFPE), perfluoroalkylether (PFAE) and perfluoropolyalkylether (PFPAE). A unique identifier is their CAS registry number, 60164-51-4.

Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula C2F4. It is the simplest perfluorinated alkene. This gaseous species is used primarily in the industrial preparation of fluoropolymers.

<span class="mw-page-title-main">Fluorinated ethylene propylene</span>

Fluorinated ethylene propylene (FEP) is a copolymer of hexafluoropropylene and tetrafluoroethylene. It differs from the polytetrafluoroethylene (PTFE) resins in that it is melt-processable using conventional injection molding and screw extrusion techniques. Fluorinated ethylene propylene was invented by DuPont and is sold under the brandname Teflon FEP. Other brandnames are Neoflon FEP from Daikin or Dyneon FEP from Dyneon/3M.

<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">Caprolactone</span> Chemical compound

ε-Caprolactone or simply caprolactone is a lactone possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to caprolactam.

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">Hexafluoropropylene oxide</span> Chemical compound

Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers. This colourless gas is the epoxide of hexafluoropropylene, which is a fluorinated analog of propylene oxide, HFPO is produced by DuPont and 3M and as a precursor to the lubricant Krytox and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.

<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.

Perfluoroalkyl carboxylic acids (PFCAs), or perfluorocarboxylic acids are compounds of the formula CnF(2n+1)CO2H that belong to the class of per- and polyfluoroalkyl substances. The simplest example is trifluoroacetic acid. These compounds are organofluorine analogues of ordinary carboxylic acids, but they are stronger by several pKa units and they exhibit great hydrophobic character. Perfluoroalkyl dicarboxylic acids (PFdiCAs) are also known, e.g. C2F4(CO2H)2.

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">Perfluoroalkoxy alkane</span> Family of polymers

Perfluoroalkoxy alkanes (PFA) are fluoropolymers. They are copolymers of tetrafluoroethylene (C2F4) and perfluoroethers (C2F3ORf, where Rf is a perfluorinated group such as trifluoromethyl (CF3)). The properties of these polymers are similar to those of polytetrafluoroethylene (PTFE). Compared to PTFE, PFA has better anti-stick properties and higher chemical resistance, at the expense of lesser scratch resistance.

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

Vinylsulfonic acid is the organosulfur compound with the chemical formula CH2=CHSO3H. It is the simplest unsaturated sulfonic acid. The C=C double bond is a site of high reactivity. Polymerization gives polyvinylsulfonic acid, especially when used as a comonomer with functionalized vinyl and (meth)acrylic acid compounds. It is a colorless, water-soluble liquid, although commercial samples can appear yellow or even red.

References

  1. Günter Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN   3-527-30673-0.
  2. Michael G. Costello; Richard M. Flynn; John G. Owens (2001). "Fluoroethers and Fluoroamines". Kirk-Othmer Encyclopedia of Chemical Technology. Weinstein: Wiley-VCH. doi:10.1002/0471238961.0612211506122514.a01.pub2. ISBN   0-471-23896-1.