Sulfuric Acid → Isosorbide

Participants

Reaction Steps

Weighed amounts of aqueous 70% sorbitol solution were added to 12 separate glass reaction tubes. Each of these reaction tubes was connected to a water trap and set up according to the diagram in FIG. 1. The water trap contained 25 mL of water. Into each reaction tube was injected 483 μL of an aqueous solution containing 0.1075 g of concentrated sulfuric acid. The nitrogen purge into each tube was adjusted to 150 cm3/min. All of the reaction tubes were lowered at once into a 180° C. oil bath. Each tube was pulled from the oil bath at different times as listed in Table 1 to cool and stop the reaction. The mass of the crude remaining in each tube was determined. Small weighed samples of crude material (on the order of 150 mg) from each separate reaction tube were removed and diluted with a weighed amount of 1,9-nonanediol (external standard) contained in approximately 10 mL of anhydrous dimethylacetamide. Approximately 1 mL of each of these solutions was transferred to a gc vial, and treated with 0.150 ml of the silating agent trimethylsilylimidazole in order to determine and quantitate the components in each reaction tube by gas chromatographic analysis. The results of these experiments are presented in Table 1.

Provenance & Evidence