2,3-Dihydroxybutanedioic Acid → Poliglecaprone

HRID 379494

Reaction equation

HRID 379494 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

5

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 93182-ethylhexanoic acid tin(II) saltHCID 10401epsilon-CAPROLACTONEHCID 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.

Workup

  1. customAt the conclusion of the reaction
  2. customthe unreacted monomer was removed
  3. temperatureby heating at 120° C. under reduced pressure for 30 minutes

Sources & evidence

ORD record
ord-b319a34dd22e476b97bb99b4f886e3ff
Source dataset
uspto-grants-2001_10
Patent number
US06299631B1

Linked notes

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