Triethanolamine → Poliglecaprone

HRID 1516032Notes

Reaction equation

HRID 1516032 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].N(CCO)(CCO)CCO.CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2]>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 7618TriethanolamineHCID 93182-ethylhexanoic acid tin(II) saltHCID 10401epsilon-CAPROLACTONEHCID 65432Glycolide

Product 1

HCID 65431Poliglecaprone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ε-caprolactone (143 g, 1.254 mole) and glycolide (7.7 g, 0.066 mole) was charged into a predried reactor, equipped for mechanical stirring, under an anhydrous nitrogen atmosphere. To this was added triethanolamine (0.13 g, 8.71×10−4 mole) as the initiator and a catalytic amount of stannous octoate (1.1 ml of a 0.2 M solution in toluene, 2.2×10−4 mole). The system was heated at 40° C. under reduced pressure for at least 10 minutes and then purged with dry nitrogen. The charge was then heated to and kept at 160° C. while maintaining mechanical stirring until the resulting polymer was too viscous to stir. The polymerization was continued for 6 hours. At the conclusion of this period, the polymer was cooled, isolated, and ground. The ground polymer was dried at 40° C. under reduced pressure and characterized for identity by NMR and IR, thermal properties by DSC, and molecular weight using inherent viscosity and GPC. The GPC chromatograms indicated no significant level of residual monomer in the polymer. Analytical data of the polymer can be summarized as follows: Tm=50° C., ΔHf=67 J/g, I.V.=1.6, Mn(by GPC in THF)=121 kDa.

Workup

  1. additionwas charged into a predried reactor
  2. customequipped for mechanical stirring, under an anhydrous nitrogen atmosphere
  3. custompurged with dry nitrogen
  4. temperatureThe charge was then heated to and
  5. customkept at 160° C.
  6. temperaturewhile maintaining mechanical
  7. stirringto stir
  8. temperatureAt the conclusion of this period, the polymer was cooled
  9. customisolated
  10. customThe ground polymer was dried at 40° C. under reduced pressure
  11. customTm=50° C., ΔHf=67 J/g, I.V

Sources & evidence

ORD record
ord-56290dc16c0444ffb1640e210494e7a3
Source dataset
uspto-grants-2012_07
Patent number
US08226683B2

Reaction notes

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