Glycolic Acid → Poliglecaprone

HRID 1018875Notes

Reaction equation

HRID 1018875 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]1[O:16][C:14](=[O:15])[CH2:13][O:12][C:10]1=[O:11].C(O)(=O)CO.CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2]>>[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]1[O:16][C:14](=[O:15])[CH2:13][O:12][C:10]1=[O:11]

Participants

5

Reactant 4

HCID 757Glycolic AcidHCID 93182-ethylhexanoic acid tin(II) saltHCID 10401epsilon-CAPROLACTONEHCID 65432Glycolide

Product 1

HCID 65431Poliglecaprone

Conditions

Temperature
180 °C

Procedure

ε-Caprolactone (57.1 g, 0.5 mole), glycolide (1.1 g, 9.5 mmole), glycolic acid (7.6 g, 0.1 mole) and stannous octoate (0.5 ml of 0.1 M solution in toluene, 20 mg, 5×10−5 mole) were added to a glass reactor. The reactor was purged with dry nitrogen gas. The reactor was heated in an oil bath at 180° C. under nitrogen for 12 hours, while the contents were magnetically stirred. The final composition was determined by 1H NMR is shown to be essentially the same as the theoretical. The Tg is −62° C., and the Tm is 37° C.

Workup

  1. customThe reactor was purged with dry nitrogen gas
  2. customis 37° C.

Sources & evidence

ORD record
ord-ecf55405c32b432c9e46abb974969412
Source dataset
uspto-grants-2002_11
Patent number
US06485749B1

Reaction notes

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