Glycolic Acid → Poliglecaprone

HRID 259658

Reaction equation

HRID 259658 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 mole), glycolic acid (7.6 g, 0.1 mole) and stannous octoate (0.5 ml of 0.1M 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 Tm is -62° C., and the Tg is 37° C.

Workup

  1. customThe reactor was purged with dry nitrogen gas
  2. customis -62° C.

Sources & evidence

ORD record
ord-a6a7c0223c554eceb3a3605fe6897a0e
Source dataset
uspto-grants-1996_06
Patent number
US05522842

Linked notes

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