D-Erythrose → Ribonic acid

Participants

Reaction Steps

Sodium ribonate (15 mmoles) was dissolved in 20 mL of water. Cation exchange resin (Amberlite IRC747 H+ form) was added to lower the pH from 6.8 to 3.5 (or approximately 50% neutralization of the starting material). The solution was filtered to remove the cation resin, the ribonate starting material was diluted to 30 mL, and 25 mL transferred to glass cell for electrolysis. The initial ribonate solution was analyzed by HPLC against a standard and quantified to be 9.54 mmoles (0.38M). The 25 mL of starting material containing 9.54 mmoles of ribonate was stirred in the glass cell, while a constant current of 0.5 amps (100 mA/cm2) was applied. The cell voltage averaged about 6.5 volts, and the pH of the substrate increased from 3.5 to 7.6 after 2F/mole of charge was passed. Samples were taken at 603, 1206 and 1809 coulombs. The samples containing the erythrose product were reduced to erythritol with an excess amount of sodium borohydride, and analyzed for erythritol by HPLC-RI. The samples were quantified for erythritol based on a response factor determined from an erythritol standard, see Table 1.

Provenance & Evidence