Methane → Bis(2-Hydroxyethyl)Sebacate

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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.

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