Itaconic acid → HCID 86676438, compound

Participants

Reaction Conditions

Reaction Steps

To a 3-neck 250 mL round-bottomed flask equipped with a dean stark trap and a condenser was added isosorbide (40.0 g, 273.9 mmol, obtained from Archer Daniels, Midland, Ill.), itaconic acid (32.39 g, 248.9 mmol, obtained from Sigma-Aldrich), and FASCAT 4201 dibutyl tin oxide catalyst (0.07 g, 0.1 wt %, obtained from Arkema Inc.). The mixture was slowly heated under argon to 120° C., during which time the reagents melted. The temperature was then raised to 180° C., and condensation began around 150° C. The reaction mixture was stirred at 180° C. overnight (˜20 h). Thereafter, vacuum (1-2 mm-Hg) was applied for ˜30 min. A total of 3.0 mL water was collected in the dean stark trap. The reaction mixture was cooled under argon to ˜100° C. and discharged into an aluminum tray and cooled to room temperature to give 65 g of product as a glassy material. Tg(DSC)=19.5° C.; viscosity @130° C.=769 cps; viscosity @70° C.=6.63×105 cps. Mn(GPC)=689; Mw(GPC)=1245; Pd(GPC)=1.80.

Provenance & Evidence