Glycerol → epsilon-Caprolactone p-Dioxanone
Reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1[CH2:14][CH2:13][O:12][CH2:11][C:10]1=[O:15].OCC(CO)O.CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2]>C1(C)C=CC=CC=1>[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1[CH2:14][CH2:13][O:12][CH2:11][C:10]1=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A flame dried, 250 mL, round bottom single neck flask was charged with 57.1 grams (0.50 mole) of ε-caprolactone, 51.0 grams (0.50 mole) of p-dioxanone, 4.00 mL (55 mmol) of distilled glycerol, and 0.12 mL (40 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried mechanical stirrer. The flask was purged with nitrogen three times before venting with nitrogen. The reaction mixture was heated to 140° C. and maintained at this temperature for about 24 hours. The reaction mixture was then cooled to 110° C. and maintained at this temperature for 24 hours. The copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 32 hours to remove any unreacted monomer. The copolymer had an inherent viscosity of 0.14 dL/g in HFIP at 25° C. The copolymer was a liquid at room temperature. The molar ratio of PCL/PDS was found to be 53.2/46.8 by proton NMR.
Workup
- customA flame dried
- customThe flask was fitted with a flame
- customdried mechanical stirrer
- customThe flask was purged with nitrogen three times
- temperaturemaintained at this temperature for about 24 hours
- temperatureThe reaction mixture was then cooled to 110° C.
- temperaturemaintained at this temperature for 24 hours
- customThe copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 32 hours
- customto remove any unreacted monomer
- customat 25° C
- customat room temperature
Sources & evidence
- ORD record
- ord-3bacf7be336e4280a82138158c26db36
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599852
Reaction notes
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