2-ethylhexanoic acid tin(II) salt → Poliglecaprone

HRID 861178Notes

Reaction equation

HRID 861178 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].CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2]>C(O)COCCO>[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 3

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

Product 1

HCID 65431Poliglecaprone

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
190 °C

Procedure

A flame dried 500 ml single-neck round-bottom flask is charged with 79.90 gm. (0.70 mole) of ε-caprolactone, 150.89 gm (1.30 mole) of glycolide, 0.228 ml (1.20 mmole/mole of total monomer) of distilled diethylene glycol and 0.135 ml stannous octoate (0.33 molar solution in toluene). The flask is fitted with a flame dried mechanical stirrer and appropriate adapters to provide a closed system. The reactor is purged three times before being vented with nitrogen. The reaction mixture is heated to 190° C. under nitrogen, and maintained at this temperature for about 16 to 18 hours. The copolymer is isolated, ground, and devolatilized (42 hours/110° C./0.1 mm Hg) to remove any unreacted monomers. A weight loss of 4.8% is observed upon devolatilization. The inherent viscosity (I.V.) of the copolymer is 1.46 dl/g in hexafluoroisoproponal (HFIP) at 25° C. The molar ratio of PCL/PGA is found to be 32.2/67.8 by NMR. The glass transition temperatures (Tg) and the melting point (Tm) of this copolymer are found to be 7° C./58° C. and 133° C., respectively, by DSC.

Workup

  1. customA flame dried 500 ml single-neck round-bottom flask
  2. additionis charged with 79.90 gm
  3. customThe flask is fitted with a flame
  4. customdried mechanical stirrer
  5. customappropriate adapters to provide a closed system
  6. customThe reactor is purged three times
  7. temperaturemaintained at this temperature for about 16 to 18 hours
  8. customThe copolymer is isolated
  9. custom(42 hours/110° C./0.1 mm Hg)
  10. customto remove any unreacted monomers
  11. customat 25° C
  12. customto be 7° C.
  13. custom58° C. and 133° C.

Sources & evidence

ORD record
ord-c7c986dcadbb4e7d98a89d63b95d6067
Source dataset
uspto-grants-1998_02
Patent number
US05713920

Reaction notes

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