Synthesis and characterization of nitroglycerin-functionalized polystyrene

The synthesis and characterization of diethyl oxomalonate-, glycerol-, and nitroglycerin-functionalized polystyrene (DPS, GPS, and NGPS) from polystyr ene (PS) by the chemical-modification route were explored. DPS was synthesi zed by the Friedel-Crafts acylation of PS with diethyl oxomalonate in the p resence of SnCl4 by a batchwise-addition process. Proton NMR studies indica te that the acylation was essentially quantitative. IR spectroscopy was add itionally used to confirm the transformation. The reduction of DPS was carr ied out using various reduction agents and reaction conditions. The sodium hydride reduction in tetrahydrofuran resulted in a quantitative conversion to GPS as estimated by H-1 NMR spectroscopy. Treatment of GPS with a nitrat ing mixture of nitric and sulfuric acids results in the formation of NGPS. All the polymers were characterized using gel permeation chromatography, IR , UV, H-1 spectroscopic techniques, pyrolysis-mass spectrometry, and thermo gravimetric analysis. This is the first investigation on the syntheses of D PS, GPS, and NGPS. (C) 2001 John Wiley & Sons, Inc.