- Radical additions to fluoroolefins. Photochemical fluoroalkylation of alkanols and alkane diols with perfluoro vinyl ethers; photo-supported O-alkylation of butane-1,4-diol with hexafluoropropene
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Butane-1,4-diol was fluoroalkylated by its photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The reactivity of perfluoro vinyl ethers was studied ( tested) in their photoaddition reactions with alkanols that were less regioselective (up to 7% rel.of regioisomer) in comparison with hexafluoropropene. Surprisingly, photo-supported base-induced nucleophilic mono-and bis-addition of butane-1,4-diol onto hexafluoropropene was observed in acetonitrile.
- Cirkva, Vladimir,Polak, Radek,Paleta, Oldrich
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Read Online
- Synthetic method of hexafluoro-1-butanol
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The invention provides a synthetic method of hexafluoro-1-butanol. The synthetic method of hexafluoro-1-butanol comprises the following step: carrying out an addition reaction on a compound of a structure as shown in a formula (I) and hydrogen under catalyst of a noble metal catalyst to obtain hexafluoro-1-butanol. By taking the compound of the structure as shown in the formula (I): 1-trifluoromethyl-trifluorooxetane as an initial raw material, hexafluoro-1-butanol is obtained by means of hydrogenation under the special catalyst. The method is mature in reaction technology of steps, conventional in raw material and mild in reaction condition, and is an advantageous technical line. Experimental results verify that the total yield of hexafluoro-1-butanol is greater than 87% and the purity isgreater than 99%.
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Paragraph 0065; 0069; 0072; 0075; 0083; 0085; 0087-0099
(2018/05/16)
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- Promising prospects for using partially fluorinated alcohols as O-nucleophilic reagents in organofluoric synthesis
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Perfluoroolefins react with isopropyl alcohol under the conditions of radical initiation to form partially fluorinated aliphatic alcohols. The reactions of these alcohols with hexafluoropropylene and compounds containing labile halogen atoms (in particular, with allyl bromide and epichlorohydrin) were studied.
- Il'in,Il'in,Bakhmutov,Furin,Pokrovskii
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p. 405 - 418
(2008/02/02)
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- HYDROFLUOROETHER COMPOUNDS AND PROCESSES FOR THEIR PREPARATION AND USE
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A hydrofluoroether compound comprises two terminal fluoroalkyl groups and an intervening substituted or unsubstituted oxymethylene group, each of the fluoroalkyl groups comprising only one hydrogen atom and, optionally, at least one catenated (that is, in-chain) heteroatom; with the proviso that the hydrogen atom is part of a monofluoromethylene moiety.
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Page/Page column 20
(2008/06/13)
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- METHOD FOR THE PREPARATION OF 2, 2, 3, 4, 4, 4-HEXAFLUORO-1-BUTANOL
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The method for preparing 2,2,3,4,4,4-hexafluoro-1-butanol includes reacting methanol and hexafluoropropene in the presence of a free radical initiator such as di-isopropyl peroxydicarbonate at 25-50° C. and a pressure of 100-300 psi in an autoclave. An inert gas such as nitrogen and argon is added to the autoclave when the pressure is lower than 100 psi in the course of the reaction.
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- Process for producing a fluoroalkanol
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A process for producing a fluoroalkanol of high purity containing little evaporation residue, which can be industrially easily carried out with high selectivity, is provided. In the process, a radial initiator and CF2=CFR3 (formula 3) are continuously added to CHR1R2—OH (Formula 2) to react them to form H—(CFR3CF2)n—CR1R2—OH (formula 1). In the formulae, n is an integer of from 1 to 4, each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group, and R3 is a fluorine atom or a C1-4 perfluoroalkyl group.
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- PROCESS FOR PRODUCING FLUOROALKANOL
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A process for producing a fluoroalkanol of high purity containing little evaporation residue, which can be industrially easily carried out with high selectivity, is provided. In the process, a radial initiator and CF2=CFR3 (formula 3) are continuously added to CHR1R2-OH (Formula 2) to react them to form H-(CFR3CF2)n-CR1R2-OH (formula 1). In the formulae, n is an integer of from 1 to 4, each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group, and R3 is a fluorine atom or a C1-4 perfluoroalkyl group.
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Page column 6
(2008/06/13)
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- Photolysis of perfluoropropylene-methanol mixture in vacuum ultraviolet
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The products of reaction of C3F6 with CH 3OH, initiated by vacuum ultraviolet, were determined. The kinetics scheme of the process was proposed. The parameters of the kinetic processes were calculated. The feasibility of p
- Fokanov,Pavlov,Semenov,Maksimov,Morozov
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p. 1275 - 1279
(2007/10/03)
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- Free Radical Chemistry. Part 3. Substituent Effects in Additions of Ethers to Fluorinated Alkenes
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Systematic studies on free-radical addition of acyclic ethers to hexafluoropropene reveal the influence of steric effects on the competitive formation of mono-, di-, and tri-adducts.It is concluded that 'captodative' effects are not dominant in systems containing polyfluoroalkyl groups.Remarkably efficient free-radical additions of trialkyl borates, to fluorinated alkenes occur, but in a series X-OMe (X=MeCO, HCO, MeOCO etc.) reactivity is reduced by electron withdrawal.
- Chambers, Richard D.,Grievson, Brian,Kelly, Noel M.
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p. 2209 - 2214
(2007/10/02)
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