Ethylene Glycol → Lactic Acid

HRID 2041803Notes

Reaction equation

HRID 2041803 reaction equation
C(O)C[OH:3].[CH3:5][CH2:6][CH2:7][CH2:8][CH:9]([C:12]([O-:14])=[O:13])CC.CCC[CH2:18][CH:19]([C:22]([O-:24])=[O:23])CC.[Sn+2].C(Cl)Cl>C(OCC)C>[C:12]1(=[O:14])[O:13][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1.[C:22]([OH:24])(=[O:23])[CH:19]([CH3:18])[OH:3]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6344DichloromethaneHCID 93182-ethylhexanoic acid tin(II) salt

Product 2

HCID 612Lactic AcidHCID 10401epsilon-CAPROLACTONE

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

10 g of poly(ethylene glycol) methyl ether (PEG 1,500, Mn=1,500) and 0.2 g of stannous octoate, which is a catalyst, were put into a reactor, and were then dried in a vacuum at a temperature of 110° C. for 4 hours in order to remove moisture therefrom. Subsequently, the dried reactants were cooled, and then 6.0 g of ε-caprolactone (5.576 ml) and 1.43 g of D,L-lactide, which are biodegradable polyester polymer compounds, were added to the dried reactant in a nitrogen atmosphere to form a reaction mixture. Then, the reaction mixture was slowly heated to a temperature of 135° C. in a nitrogen atmosphere and then polymerized for 24 hours to form a reaction product. After the polymerization reaction, the reaction product was cooled to room temperature, and was then dissolved by adding a small amount of methylene chloride thereto. The dissolved reaction product was added to excess ethyl ether and then precipitated to remove unreacted materials therefrom. Then, the reaction product, from which unreacted material was removed, was dried in a vacuum at a temperature of 40° C. for 48 hours, thereby obtaining a triblock copolymer (PCLA-PEG-PCLA) in which hydroxy groups are provided at the ends of the formed poly(ethylene glycol) and biodegradable polyester polymer compound, ε-caprolactone and lactic acid. The yield of the triblock copolymer thus obtained was 91%.

Workup

  1. customwere put into a reactor
  2. customwere then dried in a vacuum at a temperature of 110° C. for 4 hours in order
  3. customto remove moisture
  4. temperatureSubsequently, the dried reactants were cooled
  5. additionwere added to the dried reactant in a nitrogen atmosphere
  6. customto form a reaction mixture
  7. custompolymerized for 24 hours
  8. customto form a reaction product
  9. customAfter the polymerization reaction
  10. temperaturethe reaction product was cooled to room temperature
  11. dissolutionwas then dissolved
  12. customThe dissolved reaction product
  13. customprecipitated
  14. customto remove unreacted materials
  15. customThen, the reaction product, from which unreacted material was removed
  16. customwas dried in a vacuum at a temperature of 40° C. for 48 hours
  17. customobtaining a triblock copolymer (PCLA-PEG-PCLA) in which hydroxy groups

Sources & evidence

ORD record
ord-13c588f871e8491bbc2414fc32681eec
Source dataset
uspto-grants-2013_11
Patent number
US08586087B2

Reaction notes

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