Malic Acid → HCID 70298316, compound

HRID 2227119Notes

Reaction equation

HRID 2227119 reaction equation
[CH2:1]1[O:8][C:6](=[O:7])[CH2:5][O:4][C:2]1=[O:3].[C:9]([OH:17])(=[O:16])[CH:10]([CH2:12][C:13]([OH:15])=[O:14])[OH:11].CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2]>>[CH2:1]1[O:8][C:6](=[O:7])[CH2:5][O:4][C:2]1=[O:3].[C:9]([OH:17])(=[O:16])[CH:10]([CH2:12][C:13]([OH:15])=[O:14])[OH:11]

Participants

4

Reactant 3

HCID 525Malic AcidHCID 93182-ethylhexanoic acid tin(II) saltHCID 65432Glycolide

Product 1

HCID 70298316HCID 70298316, compound

Conditions

Temperature
160 °C

Procedure

A flame-dried resin kettle equipped with a mechanical stirrer and an argon inlet was charged with glycolide (2.586 mole, 300 g), anhydrous malic acid (0.172 mole, 23 g), and stannous octoate (0.2 M in toluene, 862 ml, 0.172 m mole). The polymerization reactor and its contents were purged with dry argon several times. After melting the polymerization charge, the reactants were heated to and stirred at 160° C. until the polymer started to precipitate from the melt. Shortly after partial precipitation, the stirring was terminated and the reaction was continued at 160° C. for 2 hours. At the conclusion of the polymerization, the temperature was lowered below 120° C. and excess monomer was removed under reduced pressure. The composition of the isolated polymer was verified using infrared and NMR spectroscopy. Differential Scanning Calorimetry was used to determine the polymer melting temperature (Tm=206° C.). The solid polymer was ground to achieve average particle diameter of about 125 μm using a Wiley mill. Further reduction of the particle size to 5-10 μm diameter was achieved using a jet-mill receiving pressurized dry nitrogen. The resulting microparticles were rinsed with acetone to remove trace monomer and low molecular weight oligomers. The product was then dried under reduced pressure at 40° C. until used. The average diameter of the dry microparticle was determined using a particle size analyzer.

Workup

  1. customA flame-dried resin kettle equipped with a mechanical stirrer and an argon inlet
  2. customThe polymerization reactor and its contents were purged with dry argon several times
  3. additioncharge
  4. temperaturethe reactants were heated to and
  5. customto precipitate from the melt
  6. customShortly after partial precipitation
  7. customthe stirring was terminated
  8. customAt the conclusion of the polymerization
  9. customwas lowered below 120° C.
  10. customexcess monomer was removed under reduced pressure
  11. customthe polymer melting temperature (Tm=206° C.)
  12. washThe resulting microparticles were rinsed with acetone
  13. customto remove trace monomer and low molecular weight oligomers
  14. customThe product was then dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-f3714812f5ba43eaa4a99e1774eaa946
Source dataset
uspto-grants-2002_07
Patent number
US06413539B1

Reaction notes

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