Succinic Acid → Isosorbide Succinic Acid

Participants

Reaction Conditions

Reaction Steps

To a 500 ml round bottomed flask equipped with a Dean-Stark trap and a condenser was added isosorbide (27.61 grams, 189 mmoles, available from Archer Daniels, Midland, Ill., USA), succinic acid (10.63 grams, 90 mmoles, available from Sigma Aldrich) and toluene (200 mL). The reaction mixture was heated gradually under inert atmosphere to about 120° C. (external bath temperature). The reaction mixture was heated at reflux overnight during which about 3 mL water was collected in the Dean Stark trap. The reaction mixture was cooled to room temperature and the crude product was collected as a brownish residue. Toluene was removed by decanting, and the crude product was dissolved in dichloromethane (600 mL) and washed with saturated solution of NaHCO3 (2×200 mL), followed by deionized water (1×200 mL). The solution was dried over MgSO4, and the solvent removed in vacuo and then dried under vacuum for 24 hrs, to affordan fluffy off-white solid. The product was further dried in a vacuum oven (about 200 mm-Hg at 120° C.) overnight, then cooled to room temperature to give a transparent solid material (15 grams). Glass transition (Tg) by DSC: 35° C., Viscosity at 130° C.: 515 cPs, viscosity at 60° C.: 7.3×106 cPs.

Provenance & Evidence