Adipic Acid → Bis(2-hydroxyethyl) adipate

Participants

Reaction Steps

Adipic acid (36.5g, 0.25 mole) and the catalyst of Example II (0.4g) in methyl isobutyl ketone (250 ml) were heated at 160°C and subsequently ethylene oxide (24.23g, 0.55 mole) was added; the temperature was kept at 160°C. After 60 minutes, the pressure dropped from 103 psi to 57 psi. After solvent evaporation, the crude product (60.4g) was distilled under vacuum; a light yellow material (35.0g) was obtained boiling at 202°-203°C at 1 mm pressure in 60.0% yield, having a refractive index of 1.4619 at 25°C. The infrared spectrum was consistent with that expected for the ester (3450 cm-1 (OH), 2970 cm-1 (CH2), 1730 cm-1 (C=O), and 1180 cm-1 (C-O)). Anal. Calcd. for C10H18O6 : C, 51.28; H, 7.69; O, 41.03 Found: C, 50.80; H, 7.76; Molecular weight by hydroxy number: Theory: 234. Found: 234.

Provenance & Evidence