Names | |
---|---|
IUPAC name 2,2,3-Trifluoro-3-(trifluoromethyl)oxirane | |
Other names trifluoro(trifluoromethyl)oxirane | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | HFPO |
ChemSpider | |
ECHA InfoCard | 100.006.411 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C3F6O | |
Molar mass | 166.02 g/mol |
Appearance | colourless gas |
Density | 1300kg/m3 at 25 °C |
Melting point | −144 °C (−227 °F; 129 K) |
Boiling point | −27.4 °C (−17.3 °F; 245.8 K) |
Solubility | nonpolar solvents |
Vapor pressure | 660kPa at 25 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [1]
Fluoride catalyzes the formation of perfluorinated polyethers such as Krytox. The initial step entails nucleophilic attack at the middle carbon to give the perfluoropropoxide anion, which in turn attacks another monomer. This process generates a polymer terminated by an acyl fluoride, which is hydrolyzed to the carboxylic acid which is decarboxylated with fluorine. [2] The net polymerization reaction can be represented as:
Upon heating above 150 °C, HFPO decomposes to trifluoroacetyl fluoride and difluorocarbene:
The epoxide of tetrafluoroethylene is even more unstable with respect to trifluoroacetyl fluoride.
In the presence of Lewis acids the compound rearranges to hexafluoroacetone, another important chemical intermediate. This rearrangement can be of concern during storage as the rearrangement be catalyzed by the material of the storage cylinder's walls and leads to unwanted formation of HFA during storage. As a result of this, 3M recommends using all HFPO shipped in carbon-steel containers within 90 days of shipping. [3]
Methanolysis affords methyl trifluoropyruvate, a reagent useful in organic synthesis: [4]
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.
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams.
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.
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.
Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in contrast to molecular hydrides such as borane, methane, ammonia, water, and hydrogen fluoride. It is an ionic material that is insoluble in all solvents (other than molten Na), consistent with the fact that H− ions do not exist in solution. Because of the insolubility of NaH, all reactions involving NaH occur at the surface of the solid.
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor.
In organic chemistry a halohydrin is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups. The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers.
In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group. If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily breaks, producing free radicals of the form RO•. Thus, organic peroxides are useful as initiators for some types of polymerization, such as the acrylic, unsaturated polyester, and vinyl ester resins used in glass-reinforced plastics. MEKP and benzoyl peroxide are commonly used for this purpose. However, the same property also means that organic peroxides can explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful bleaching agents.
Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol (F
3C)
2C(OH)
2, a geminal diol.
Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry.
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.
Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species. Industrially, these compounds are mainly used for the production of polyolefins.
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.
Perfluorobutanoic acid (PFBA) is a perfluoroalkyl carboxylic acid with the formula C3F7CO2H. As the perfluorinated derivative of butyric acid, this colourless liquid is prepared by electrofluorination of the corresponding butyryl fluoride.
Fluorination by sulfur tetrafluoride produces organofluorine compounds from oxidized organic compounds, including alcohols, carbonyl compounds, alkyl halides, and others.
An insertion reaction is a chemical reaction where one chemical entity interposes itself into an existing bond of typically a second chemical entity e.g.:
Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3COOOH. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.
Peroxymonophosphoric acid is an oxyacid of phosphorus. It is a colorless viscous oil. Its salts are called peroxymonophosphates. Another peroxyphosphoric acid is peroxydiphosphoric acid, H4P2O8.