A Safe Two-Step Process for Manufacturing Glycidyl Nitrate from Glycidol Involving Solid-Liquid Phase-Transfer Catalysis

作者：Ochoa Gomez Jose R^*; Blanco Gomez Juan J

来源：Organic Process Research & Development, 2011, 15(6): 1454-1457.

DOI：10.1021/op200066e

A new and safer two-step process for manufacturing glycidyl nitrate from glycidol is reported. In the first step glycidyl tosylate is obtained by reacting glycidol with p-tosyl chloride in the presence of triethylamine according to any one of the well-known procedures for obtaining tosyl esters described in the literature. In the second step, glycidyl tosylate is reacted with NaNO(3) in refluxing acetonitrile under solid-liquid phase-transfer catalysis conditions using tetrabutylammonium nitrate as catalyst. Acetonitrile and the phase-transfer catalyst were recycled 12 times without deactivation, yielding 99% pure glycidyl nitrate in a cumulative isolated yield of 81.5% with a catalyst turnover number of 85.7 mol substrate per mol phase-transfer catalyst. This procedure avoids the use of the dangerous reactants used in the current manufacturing processes of glycidyl nitrate and could be useful as a safe and general method for obtaining nitrate esters.

• 出版日期2011-12