2,3-Dihydroxybutanedioic Acid → HCID 131723362, compound

HRID 2227120Notes

Reaction equation

HRID 2227120 reaction equation
[CH2:1]1[O:8][C:6](=[O:7])[CH2:5][O:4][C:2]1=[O:3].[C:9]([OH:18])(=[O:17])[CH:10]([CH:12]([C:14]([OH:16])=[O:15])[OH:13])[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:18])(=[O:17])[CH:10]([CH:12]([C:14]([OH:16])=[O:15])[OH:13])[OH:11]

Participants

4

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 93182-ethylhexanoic acid tin(II) saltHCID 65432Glycolide

Product 1

HCID 131723362HCID 131723362, 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 tartaric acid (0.172 mole, 26.8 g), and stannous octoate (0.2 M in toluene, 862 ml, 0.0172 mmole). 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=204° 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 m diameter was achieved using a jet-mill receiving pressurized dry nitrogen. The resulting microparticles were rinsed with acetone to remove trace amounts of 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=204° C.)
  12. washThe resulting microparticles were rinsed with acetone
  13. customto remove trace amounts of monomer and low molecular weight oligomers
  14. customThe product was then dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-64c89dc01f74463487295ca180740451
Source dataset
uspto-grants-2002_07
Patent number
US06413539B1

Reaction notes

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