Malic Acid → HCID 86676439, compound
Reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([OH:19])(=[O:18])[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[OH:13]>C([Sn](=O)CCCC)CCC>[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([OH:19])(=[O:18])[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[OH:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
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), malic acid (30.60 g, 228.22 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). 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 63 g of product as a glassy material. Tg(DSC)=23.2° C.; viscosity @130° C.=1019 cps; viscosity @70° C.=8.08×105 cps. Mn(GPC)=567; Mw(GPC)=868; Pd(GPC)=1.53.
Workup
- customTo a 3-neck 250 mL round-bottomed flask equipped with a dean stark trap and a condenser
- temperatureThe temperature was then raised to 180° C.
- customcondensation
- custombegan around 150° C
- customA total of 3.0 mL water was collected in the dean stark trap
- temperatureThe reaction mixture was cooled under argon to ˜100° C.
- temperaturecooled to room temperature
Sources & evidence
- ORD record
- ord-e035f9aea4634649abba4c6a3c0de7a9
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08968452B2
Reaction notes
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