Methane → Bis(2-Hydroxyethyl)Sebacate

Participants

Reaction Conditions

Reaction Steps

Sebacic acid (50.5g, 0.25 mole), the catalyst of Example II (0.5g), and methyl isobutyl ketone (250 ml) were charged to the autoclave and heated to 150°C. Ethylene oxide (24.23g, 0.55 mole) was introduced from a nitrogen-pressurized cylinder to the autoclave. The temperature rose to 160°C and the pressure increased from 25 psi to 100 psi. After 60 minutes at 160°C, the pressure dropped to 88 psi and the system was vented. The light yellow green reaction mixture was mixed with carbon black, heated to boiling, and filtered through a sintered-glass funnel containing some Al2O3. Upon cooling to -30°C, the precipitated material was filtered, washed with cold hexane, dried in a vacuum desiccator for 48 hours and weighed (31.0g). The product was isolated in 44.0% yield and melted at 47°C. The infrared bands at 3350 cm-1 (OH), 2970 cm-1 (CH2) and 1730 cm-1 (C=O) were characteristic of the expected ester. Anal. Calcd. for C14H26O6 : C, 57.93; H, 8.97; O, 33.10. Found: C, 58.00; H, 9.02. Molecular weight by hydroxyl number. Theory: 290. Found: 289.

Provenance & Evidence