V. E. Kirichenko

Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol

The reactions of epoxy derivatives of internal perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 23–67% of the corresponding 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols, respectively. When N,N-dimethylacetamide was used as a solvent, the main reaction pathway was anionic isomerization of epoxides into ketones which were then converted into 2-perfluoroalkylbenzimidazoles (in the reactions with o-phenylenediamine) or 2-hydroxy-N-perfluoroalkanoylanilines (in the reactions with 2-aminophenol). The reaction of 3,4-epoxydodecafluorohexane with 2-aminophenol in N,N-dimethylacetamide was accompanied by unusual cyclization to afford 2-pentafluoropropanoyl-2-pentafluoroethyl-1,3-benzoxazolidine.

Determination of 1,2,3-benzotriazole in aqueous solutions and air by reaction-gas-liquid chromatography

A procedure is developed for the gas-chromatographic determination of 1,2,3-benzotriazole including preliminary derivatization with acetic anhydride in an aqueous solution followed by the extraction the derivative with toluene. The procedure is applied to the analysis of water samples, process solutions for treating metals, air of the working zone, and industrial emissions. Determination limits in water media are 0.01 mg/L and in the air of the working zone, 0.1 mg/m3.

Features of reaction between fluorine-containing glycidyl ethers and alcohols in basic medium

The reaction of fluorine-containing glycidyl ethers with various alcohols (i-PrOH, MeOH, PhOH, 2,2,3,3-tetrafluoropropanol) in basic medium resulted in products of regioselective opening of the oxirane ring. In reaction of 2,2,3,3-tetrafluoropropyloxymethyloxirane with 2-propanol under conditions of phase-transfer catalysis the main product was the corresponding 1,2-diol (yield 42%).

Preparation of Amino Derivatives from Industrial Mixtures of Polychlorobiphenyls

Chemical utilization (conversion) of polychlorobiphenyls by nitration of their industrial mixture was studied. Reduction of the nitro derivatives gave mixtures of aminopolychlorobiphenyls.

Products of the reaction of polychlorinated biphenyls with ethanol and potassium hydroxide in dimethyl sulfoxide

The reaction of a technical mixture of polychlorinated biphenyls with ethanol and potassium hydroxide in dimethyl sulfoxide was studied. The composition of the products formed in the process was determined by gas chromatography and gas chromatography mass spectrometry.

Reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol

The reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol in N,N-dimethylacetamide gave 3-(2-aminophenylsulfanyl)-1,1,1,3,4,4,4-heptafluorobutane-2,2-diol. In the reaction of the same compounds in dioxane, 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol was formed as a result of primary attack by the amino group in 2-aminobenzenethiol on the epoxy ring. The same product was obtained by treatment with 2-aminobenzenethiol of 2,3-bis(trifluoromethyl)-2H-1,4-benzoxazin-2-ol which was synthesized from 2,3-epoxyoctafluorobutane and 2-aminophenol.

Synthesis and GC-MS study of fluorinated esters derived from thrimethylolpropane

Zol-gel process was used to synthesize equilibrium mixtures of mono-, di-, and trimester derived from trimethylolpropane and perfluorocarboxylic acids. The elution order of the components of the mixtures from a weakly polar HP-5 column was established. The mass spectra of the synthesized compounds were studied. The GC-MS parameters of the products were compared with the respective parameters of their nonfluorinated analogs. The characteristics of the fluorinated esters have features determined by the esterification degree and the nature of the perfluoroalkyl groups, due to which these compounds can be identified in mixtures.