Succinic Acid → Isosorbide Succinic Acid

온도

180 °C

To a 1 L Parr reactor equipped with a double turbine agitator and distillation apparatus was charged 483.3 g isosorbide, 186.2 g succinic acid, and 2.0 g VERTEC AC422 catalyst (organic titanate obtained from Johnson Matthey, Tex.). The contents were heated to 180° C. over 3 h and allowed to stir for an additional 4 h; the temperature was then raised to 195° C. and the reaction mixture was allowed to stir overnight, during which 35 g water were collected. The pressure was then reduced to 200 mm-Hg for ˜1 h, after which the temperature was raised to 200° C. and the pressure was reduced to ˜1-2 mm-Hg for 1 h. The mixture was stirred for ˜2 hours at 200° C. under nitrogen and reduced pressure (1-2 mm-Hg) for an additional 1 h, after which the mixture was cooled under nitrogen and discharged into an aluminum pan at 120° C. During the reaction a total of 55 g of water was collected. NMR indicated the presence of residual isosorbide. About 150 g of the product was then added to a 1 L Erlenmeyer flask, dissolved in dichloromethane (˜300 mL), and washed with saturated NaHCO3 (2×200 mL) followed by washing with water (1×200 mL). The solution was dried with MgSO4, rotovapped to remove solvent, and dried on a vacuum pump overnight to give an off-white fluffy solid. The product was further dried in a vacuum oven (˜200 mm-Hg at 120° C.) overnight. The product was cooled to room temperature to give a glassy material (70 g). Tg(DSC)=33° C.; viscosity @130° C.=439 cps; viscosity @65° C.=1.7×106 cps. Mn(GPC)=1078; Mw(GPC)=1276; Pd(GPC)=1.18.

1. customTo a 1 L Parr reactor equipped with a double turbine agitator and distillation apparatus
2. temperaturethe temperature was then raised to 195° C.
3. customwere collected
4. waitThe pressure was then reduced to 200 mm-Hg for ˜1 h
5. temperatureafter which the temperature was raised to 200° C.
6. waitthe pressure was reduced to ˜1-2 mm-Hg for 1 h
7. stirringThe mixture was stirred for ˜2 hours at 200° C. under nitrogen
8. waitreduced pressure (1-2 mm-Hg) for an additional 1 h
9. temperatureafter which the mixture was cooled under nitrogen
10. customdischarged into an aluminum pan at 120° C
11. customDuring the reaction a total of 55 g of water
12. customwas collected
13. additionAbout 150 g of the product was then added to a 1 L Erlenmeyer flask
14. dissolutiondissolved in dichloromethane (˜300 mL)
15. washwashed with saturated NaHCO3 (2×200 mL)
16. washby washing with water (1×200 mL)
17. dry with materialThe solution was dried with MgSO4
18. customto remove solvent
19. customdried on a vacuum pump overnight
20. customto give an off-white fluffy solid
21. customThe product was further dried in a vacuum oven (˜200 mm-Hg at 120° C.) overnight
22. temperatureThe product was cooled to room temperature

ORD 기록

ord-d816a1c7b85842d1b144cbc4b8bfb8e3

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08968452B2