Propylene Glycol → TMC caprolactone

HRID 2265

Reaction equation

HRID 2265 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]1.C(O)C(O)C.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.[C:9]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 93182-ethylhexanoic acid tin(II) saltHCID 10401epsilon-CAPROLACTONEHCID 123834Trimethylene carbonate

Product 1

HCID 11275958TMC caprolactone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A flame dried, 250 mL, round bottom single neck flask was charged with 102.7 grams (0.90 mole) of ε-caprolactone, 10.2 grams (0.10 mole) of trimethylene carbonate, 2.9 mL (40 mmol) of propylene glycol (USP), and 0.10 mL (34 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried mechanical stirrer. The flask was purged with nitrogen three times before venting with nitrogen. The reaction mixture was heated to 160° C. and maintained at this temperature for about 18-20 hours. The copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 16 hours to remove any unreacted monomer. The copolymer had an inherent viscosity of 0.25 dL/g in HFIP at 25° C. The copolymer was a viscous liquid at room temperature.

Workup

  1. customA flame dried
  2. customThe flask was fitted with a flame
  3. customdried mechanical stirrer
  4. customThe flask was purged with nitrogen three times
  5. temperaturemaintained at this temperature for about 18-20 hours
  6. customThe copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 16 hours
  7. customto remove any unreacted monomer
  8. customat 25° C
  9. customat room temperature

Sources & evidence

ORD record
ord-8ed745f48d774f70a727a25216a3f78b
Source dataset
uspto-grants-1998_03
Patent number
US05728752

Linked notes

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