Glycolic Acid → Glyoxylic Acid

HRID 1755971Notes

Reaction equation

HRID 1755971 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N)CN.C(O)(=[O:13])CC.[C:15]([O-:19])(=[O:18])[CH2:16][OH:17].O=O>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:16]([OH:13])(=[O:17])[C:15]([OH:19])=[O:18]

Participants

8

Reactant 6

HCID 757Glycolic AcidHCID 977OxygenHCID 1032Propionic AcidHCID 3301EthylenediamineHCID 5460308HydroxyacetateHCID 178435160HCID 178435160, compound

Product 2

HCID 760Glyoxylic AcidHCID 971Oxalic Acid

Conditions

Temperature
15 °C

Procedure

Into a 2.5-cm ID×20 cm glass column equipped with a 20-μm polyethylene bed support was placed 10 mL of a solution containing glycolic acid (0.25M), ethylenediamine (0.33M), propionic acid (0.075M, HPLC internal standard), and flavin mononucleotide (0.2 mM). The column and its contents were cooled to 15° C., then 2.5 IU of spinach glycolate oxidase and 27,000 IU of Aspergillus niger catalase (co-immobilized on Eupergit C) were added to the solution. Oxygen was then passed through the porous bed support and bubbled through the reaction mixture at a rate of 10 mL/min. The reaction was monitored by taking a 100 μL aliquot of the reaction mixture at regular intervals, mixing the aliquot with 300 μL of 0.1N sulfuric acid to quench the reaction, filtering the aliquot and analyzing by HPLC. After 5.5 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 98%, 2%, and 0%, respectively, with complete conversion of glycolic acid. The final activities of glycolate oxidase and catalase were 95% and 65% of their initial values.

Workup

  1. custombubbled through the reaction mixture at a rate of 10 mL/min
  2. additionmixing the aliquot with 300 μL of 0.1N sulfuric acid
  3. customto quench
  4. customthe reaction
  5. filtrationfiltering the aliquot and analyzing by HPLC

Sources & evidence

ORD record
ord-a056e8e267f447c1a8ce3b302a5844a7
Source dataset
uspto-grants-1995_08
Patent number
US05439813

Reaction notes

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