Succinic Acid → Isosorbide Succinic Acid

온도

120 °C

To a 500 ml round bottomed flask equipped with a Dean-Stark trap and a condenser was added isosorbide (27.61 grams, 189 mmoles, available from Archer Daniels, Midland, Ill., USA), succinic acid (10.63 grams, 90 mmoles, available from Sigma Aldrich) and toluene (200 mL). The reaction mixture was heated gradually under inert atmosphere to about 120° C. (external bath temperature). The reaction mixture was heated at reflux overnight during which about 3 mL water was collected in the Dean Stark trap. The reaction mixture was cooled to room temperature and the crude product was collected as a brownish residue. Toluene was removed by decanting, and the crude product was dissolved in dichloromethane (600 mL) and washed with saturated solution of NaHCO3 (2×200 mL), followed by deionized water (1×200 mL). The solution was dried over MgSO4, and the solvent removed in vacuo and then dried under vacuum for 24 hrs, to affordan fluffy off-white solid. The product was further dried in a vacuum oven (about 200 mm-Hg at 120° C.) overnight, then cooled to room temperature to give a transparent solid material (15 grams). Glass transition (Tg) by DSC: 35° C., Viscosity at 130° C.: 515 cPs, viscosity at 60° C.: 7.3×106 cPs.

1. customTo a 500 ml round bottomed flask equipped with a Dean-Stark trap and a condenser
2. temperatureThe reaction mixture was heated
3. customwas collected in the Dean Stark trap
4. temperatureThe reaction mixture was cooled to room temperature
5. customthe crude product was collected as a brownish residue
6. customToluene was removed
7. customby decanting
8. dissolutionthe crude product was dissolved in dichloromethane (600 mL)
9. washwashed with saturated solution of NaHCO3 (2×200 mL)
10. dry with materialThe solution was dried over MgSO4
11. customthe solvent removed in vacuo
12. customdried under vacuum for 24 hrs
13. customThe product was further dried in a vacuum oven (about 200 mm-Hg at 120° C.) overnight
14. temperaturecooled to room temperature

ORD 기록

ord-762258c7fc9a48a794faad0a84a8af2a

출처 데이터셋

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08888907B2