Síntese de surfactantes derivados da D-ribonolactona

Abstract

Surfactants are amphiphilic compounds widely used in cosmetics, food and paint industries. The need for products obtained from natural raw materials instead of petroleum derivatives has led searchers, to the development “natural surfactants” derivated from carbohydrates, biodegradable and atoxic. In this work, we describe the preparation of amphiphilic compounds derivated from D-(+)-ribonic γ-lactone, which can also act as antibacterial and antifungal agents. We describe the synthesis and characterization of N-alkyl diamines bearing carbonic chain of several extent, and its respective ribonamides, beyond of the synthesis of hydrazones derivative from D-(+)-ribonic γ-lactone. The monoalkylated diamines were prepared by reaction of the mesylates or alkyl chlorides with 1,2-ethanediamine and 1,3-propanediamine in ethanol under reflux. The ribonamides were obtained by condensation of these aminated intermediates with D(+)ribonic γ-lactone. The hydrazones were obtained by condensation of long chain aldehydes with hydrazide, latter preparated by reation of D-(+)-ribonic γ-lactone with hydrazine hydrate 80%. The structures of the obtained products were elucidated by infrared spectroscopy, 1H and 13C NMR spectroscopy and by elemental analyses, beyond mass spectrometry for any compounds. Surface tension measurements were done for determination of critical micelle concentration of some ribonamides. Biological activity against Mycobacterium tuberculosis, Cândida albicans, Staphylococcus aureus and Escherichia coli was evaluated for ribonamides and hydrazones.