반응 #955901

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isosorbide

succinic acid

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material

수율 16.8%

Isosorbide Succinic Acid

수율 16.8%

용매

water

반응 조건

후처리

1. 1
   기타To a 1 L Parr reactor equipped with a double turbine agitator and distillation apparatus
2. 2
   온도the temperature was then raised to 195° C.
3. 3
   기타were collected
4. 4
   workup.WAITThe pressure was then reduced to 200 mm-Hg for ˜1 h
5. 5
   온도after which the temperature was raised to 200° C.
6. 6
   workup.WAITthe pressure was reduced to ˜1-2 mm-Hg for 1 h
7. 7
   workup.STIRRINGThe mixture was stirred for ˜2 hours at 200° C. under nitrogen
8. 8
   workup.WAITreduced pressure (1-2 mm-Hg) for an additional 1 h
9. 9
   온도after which the mixture was cooled under nitrogen
10. 10
    기타discharged into an aluminum pan at 120° C
11. 11
    기타During the reaction a total of 55 g of water
12. 12
    기타was collected
13. 13
    workup.ADDITIONAbout 150 g of the product was then added to a 1 L Erlenmeyer flask
14. 14
    workup.DISSOLUTIONdissolved in dichloromethane (˜300 mL)
15. 15
    세척washed with saturated NaHCO3 (2×200 mL)
16. 16
    세척by washing with water (1×200 mL)
17. 17
    건조The solution was dried with MgSO4
18. 18
    기타to remove solvent
19. 19
    기타dried on a vacuum pump overnight
20. 20
    기타to give an off-white fluffy solid
21. 21
    기타The product was further dried in a vacuum oven (˜200 mm-Hg at 120° C.) overnight
22. 22
    온도The product was cooled to room temperature

실험 절차

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.

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