1-Dodecanol → L-lactide epsilon-caprolactone

HRID 1449651Notes

Reaction equation

HRID 1449651 reaction equation
C(O)CCCCCCCCCCC.[CH3:14][CH2:15][CH2:16][CH2:17][CH:18]([C:21]([O-:23])=[O:22])[CH2:19]C.CCC[CH2:27][CH:28]([C:31]([O-:33])=[O:32])CC.[Sn+2]>>[C:21]1(=[O:23])[O:22][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[CH3:27][C@@H:28]1[O:23][C:21](=[O:22])[C@H:18]([CH3:19])[O:33][C:31]1=[O:32]

Participants

3

Reactant 2

HCID 81931-DodecanolHCID 93182-ethylhexanoic acid tin(II) salt

Product 1

HCID 131710947L-lactide epsilon-caprolactone

Procedure

The procedure in Example 1 was substantially repeated, except that 13.6 mL of 1-dodecanol instead of 4.00 mL of glycerol and 0.12 mL (40 μmol) instead of 0.10 mL of stannous octoate solution were used. The copolymer was dried under vacuum (0.1 mm Hg) at 110° C. for about 16 hours to remove any unreacted monomer. The copolymer had an inherent viscosity of 0.15 dL/g in HFIP at 25° C. The copolymer was viscous liquid at room temperature. The molar ratio of PCL/PLA was found to be 51.5/48.5 by proton NMR.

Workup

  1. customThe copolymer was dried under vacuum (0.1 mm Hg) at 110° C. for about 16 hours
  2. customto remove any unreacted monomer
  3. customat 25° C
  4. customat room temperature

Sources & evidence

ORD record
ord-80fc460e5aa84db2b23e82107bb1f815
Source dataset
uspto-grants-1997_02
Patent number
US05599852

Reaction notes

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