| Keywords | Fluorination / PPDA / N,N-Diethyl 1,1,2,3,3,3,-Hexafluoropropylamine / Terpenic Alcohols / さび止め性 / 抗菌性 |
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| Research Abstract |
Fluorination of fatty alcohols and terpenic alcohols with 1,1,2,3,3,3,-hexafluoropropyl diethylamine (PPDA) was investigated. A mixture of lauryl fluoride (yield 54 %) and lauryl 2,3,3,3,-tetrafluoro-propionate (yield 22%) was obtained from the reaction of PPDA and lauryl alcohol. Similar results were obtained from other fatty alcohols and terpenic alcohols. Fluorination of halogeno alcohols with PPDA was investigated. 2-Bromo-1-fluorobutane was obtained from the reaction of PPDA and 2-bromo-1-butanol (yield 50%). Similar results were obtained from other aliphatic and aromatic halogeno alcohols. However, the corresponding 2,3,3,3,-tetrafluoropropionate esters were obtained from the reactions of PPDA and -halogeno cycloalkanols, such as 2-chlorocyclohexanol.
The reaction of PPDA with hydroxy esters having PhC(H) (OH) groups gave their corresponding secondary fluorides. Fluorination of (R)-(-)-mandelic acid ethylester gave ethyl (S)-(+)-2-fluoro-2-fluoro-2 phenyl-acetate, The reaction mechanism of the fluorination by PPDA is suggested to the S_N2 type.<omega>-Fluoro carboxylic acid esters were prepared by the reaction of hydroxy esters with PPDA.
Fluorination of mono- and disubstituted glycerols with PPDA was attempted. From a disubstituted glycerol, the major product was the fluorinated propyl ester. With a monosubstituted glycerol, a cyclic adduct was obtained.
By reaction with PPDA, various monoesters of ethylene glycol gave a mixture of the corresponding monofluorides and 2,3,3,3,-tetrafluoropropionate esters. The antimicrobial properties of these fluorine compounds for a spent coolant were examined. The aqueous emulsions of benzoyloxyethl 2,3,3,3-tetra-fluoropropionate and 2-fluoropropyl benzoate showed considerable antimicrobial activity for spent coolant of water soluble cutting fluids. These new additives for water-based cutting fluids were not previously known. Ther fluorides did not show bioactive properties for some insects.
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