2,3-Dihydroxybutanedioic Acid → Poliglecaprone

Reaction equation

[CH2:1]1[O:8][C:6](=[O:7])[CH2:5][O:4][C:2]1=[O:3].[C:9]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2].C(O)(=O)C(C(C(O)=O)O)O>>[C:9]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:1]1[O:8][C:6](=[O:7])[CH2:5][O:4][C:2]1=[O:3]

Participants

Reactant 4

HCID 8752,3-Dihydroxybutanedioic Acid

HCID 93182-ethylhexanoic acid tin(II) salt

HCID 10401epsilon-CAPROLACTONE

HCID 65432Glycolide

Product 1

HCID 65431Poliglecaprone

Conditions

Temperature: 150 °C

Procedure

Glycolide (0.08865 moles) was mixed with ε-caprolactone (1.455 moles) and a catalytic amount of stannous octoate (0.3 moles) and tartaric acid (0.075 moles). The system was heated at 150° C. and was stirred at this temperature for 6 hours. At the conclusion of the reaction, the unreacted monomer was removed by heating at 120° C. under reduced pressure for 30 minutes. The resulting polymer had a peak melting temperature of 49.1° C. as measured by DSC and an Mw of 151,948 as measured by GPC.