Synthesis of polynitroalcohols by nucleophilic addition of butadiene–styrene nitrooligomer to acetaldehyde

Two types of secondary polynitroalcohols (PNA) were prepared by AN-reaction of butadiene–styrene nitrooligomer (BSNO) and acetaldehyde. The corresponding yields were 58–64% and 25–33%. The reaction was conducted in water–ethanol solution in the presence of alkaline base as catalyst at temperatures from 40 to 60 °C, for 3.5–4 h. Introduction of hydroxyethyl groups by AN-reaction of BSNO to acetaldehyde increased the polarity and thermal stability of PNA as compared to BSNO. By using IR spectroscopy and liquid absorption chromatography on silica gel, PNA were found to be polyfunctional compounds, that contained structurally and functionally heterogeneous fractions. The quantitative functional composition of the first PNA type as well as their main fractions were determined by evaluating the relative content of nitro-, carbonyl and hydroxyl groups in the products. PNA are considered to be starting materials for the preparation of polynitrourethanes and salts of N-containing sulphonic acids.