Perfluorovinyl

The reaction of OF2 and various unsaturated fluorocarbons has been examined (35,36) and it is claimed that OF2 can be used to chain-extend fluoropolyenes, convert functional perfluorovinyl groups to acyl fluorides and/or epoxide groups, and act as a monomer for an addition-type copolymerization with diolefins. 

Perfluorinated ethylene—propylene copolymers, Tetrafluoroethylene—ethylene copolymers, Tetrafluoroethylene—perfluorovinyl ether copolymers, Poly(vinyl fluoride),... 

Tetrafluoroethylene [116-14-3] and perfluorovinyl ether are copolymerized in aqueous (1,2) or nonaqueous (3) media. The polymer is separated and converted into various forms, such as extmded cubes, powders, beads, or dispersions. This family of products is manufactured by Du Pont, Daikin, and Hoechst and sold under the trade names of Teflon PEA, Neoflon AP, and Hostaflon TEA, respectively. 

Preparation. The preparation of tetrafluoroethylene has been described previously. Perfluorovinyl ethers (4—7) are prepared by the following steps. Hexafluoropropylene [116-15-4] (HEP) is oxidized to an epoxide HEPO [428-59-1] (5) which, on reaction with perfluorinated acyl fluorides, gives an alkoxyacyl fluoride. 

The perfluorovinyl ether comonomer used for PEA is expensive, as is PEA. Most PEA grades are sold as extmded, translucent cubes in various colors at 47.9—60.3/kg. Some PEA types are also marketed in nonextmded forms. 

Eor curing copolymers of tetrafluoroethylene and perfluorovinyl ether, addition of ca 4% TAG has been proposed (118). TEE—propylene copolymers have been cured by TAG and organic peroxide (119). Copolymers of TEE-propylene-vinyUdene fluoride are cured with TAG by heating at 200°C. 

Higher perfluorovinylic bromides other than trifluorovinyl bromide and pentafluoropropenyl bromide [55] have not been synthesized until recently [42, 54,... 

An extension ot this reaction provides a number of other perfluorovinylic halides [54] The type of reaction products from the thermal decomposition reaction and the type of hydrocarbon Grignard reagent used in the exchange reaction are solvent-dependent When an excess ot phenylmagnesium bromide is used, a variety of phenylated products are formed depending on the excess amount used [4S (equation 23)... 

Perfluorovinyl organotin compounds can be prepared from perfluorovinyl Grignard reagents and organotin halides [76] (equation 11) Yields are slightly improved under Barbier conditions [76]... 

Table 5. Preparation of Vinylcadmlum Reagents from Perfluorovinyl Halides and Cadmium Metal [143]...

Perfluorovinylmercury compounds can be prepared via the reaction of perfluorovinyl Grignard reagents with mercury salts [16] (equation 127), either mono- or bismercurials can be obtained. The use of alkyl or aryl mercury salts gives the mixed bismercurials, (Z)-CgFj3CF=CFHgC2H3 (50%) [16] and (Z)-... 

Perfluorovinyl iodides readily undergo stereospecific coupling with the tn-fluoroinethylcopper solution [224] (equation 151) prepared from dibromodifluo-romethane [210] With longer-chain perfluoroalkylcopper reagents, the coupling reaction is accompanied by some exchange processes [225] (equation 152)... 

The reaction of these acetylenic copper compounds with perfluorovinyl iodides stereospecifically gives the perfluoroeneynes [147, 755] (equations 172 and 173). 

The nucleophilic reaction of bromotrifluoroethene with alkoxides yields not only the expected addition and addition-elimination products but also a product from a bromophilic reaction of the carbanion intermediate [6] (equation 3) Similar are the reactions of sodium phenoxide with perfluorovinyl ethers in the presence of hexachloroethane or selected vicinal dibromoperfluoroalkanes The intermediate carbanion is trapped in high yield by these sources of Cl or Br, which suggests a... 

Since PTFE was first synthesized more than 50 years ago, fluoropolymers have been produced by radical polymerization and copolymerizaton processes, but without any functional groups, for several reasons. First, the synthesis of functional vinyl compounds suitable for radical polymerization is much more complicated and expensive in comparison with common fluoroolefins. In radical polymerization of one of the simplest possible candidates—perfluorovinyl sulfonic acid (or sulfonyl fluoride—there was not enough reactivity to provide high-molecular-weight polymers or even perfluorinated copolymers with considerable functional comonomer content. Several methods for the synthesis of the other simplest monomer—trifluoroacrylic acid or its esters—were reported,1 but convenient improved synthesis of these compounds as well as radical copolymerization with TFE induced by y-irradiation were not described until 1980.2... 

Perfluorinated polymers, 18 288-353. See also Perfluorinated ethylene-propylene (FEP) copolymers poly tetr afluoroethylene, 18 288—306 tetrafluoroethylene-ethylene copolymers, 18 316-329 tetrafluoroethylene-perfluorodioxole copolymers, 18 339-342 tetrafluoroethylene-perfluorovinyl ether, 18 329-339... 

Perfluorotributylamine, as blood substitute, 4 112-113 Perfluorovinyl ethers, preparation of, 18 329-330... 

Teflon HP Plus copolymers, 18 331 in lotus effect surfaces, 22 117 Teflon PFA. See also Tetrafluoroethylene-perfluorovinyl ether applications of, 18 338-339 chemical properties of, 18 332-333 economic aspects of, 18 338 electrical properties of, 18 334 health and safety factors related to, 18 338... 

Tetrafluoroethylene-(TFE)-perfluoropropyl vinyl ether copolymers, 7 641 Tetrafluoroethylene-perfluorovinyl ether, 48 329-339. See also Teflon PFA copolymerization of, 48 330—331 Tetrafluoroethylene-perfluorodioxole copolymers, 48 339—342. See also Teflon AF copolymers applications of, 48 342 economic aspects of, 48 341—342 health and safety factors related to, 48 342 monomer preparation, 48 339 synthesis of, 48 339-340 Tetrafluoroethylene (TFE) copolymerization with... 

Nucleophilic fluoroalkylation in the anomeric position has been performed with trifluorochloroethylene, or with perfluorovinyl ethers." The compound obtained with trifluorochloroethylene is an irreversible inhibitor of a-glycosidases (Figure 6.44). " Trifluoromethylzinc bromide can be used to perform the difluor-omethylation of hydroxyls in various positions, probably through a carbenic mechanism. 

PDD as well as other dioxoles have been copolymerized with monomers such as vinyl fluoride, vinylidene fluoride, tiifluoroediylene, perfluoroalkylethylenes, chlorotrifluoroethylene, hexafluoropropylene, and perfluorovinyl ethers, some of which contain functional groups. 

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