Glycolic Acid → Glyoxylic Acid

HRID 1755975Notes

Reaction equation

HRID 1755975 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

7

Reactant 5

HCID 757Glycolic AcidHCID 977OxygenHCID 1032Propionic AcidHCID 3301EthylenediamineHCID 5460308Hydroxyacetate

Product 2

HCID 760Glyoxylic AcidHCID 971Oxalic Acid

Conditions

Temperature
15 °C

Procedure

A 300-mL EZE-Seal stirred autoclave (Autoclave Engineers) was charged with 100 mL of a solution containing glycolic acid (0.75M), ethylenediamine (0.86M, pH 9.0), propionic acid (0.075M, HPLC internal standard), and flavin mononucleotide (0.01 mM), and the solution cooled to 15° C. To the autoclave was then added 89 IU of spinach glycolate oxidase and 72,600 IU of Aspergillus niger catalase co-immobilized on ca. 28 g of Eupergit C. The resulting mixture was stirred at 500 rpm and 15° C. under 70 psig (483 kPa) of oxygen, while bubbling oxygen through the mixture at 100 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 3 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 100%, 0%, and 0%, respectively, with complete conversion of glycolic acid. The final activities of glycolate oxidase and catalase were 100% and 100% of their initial values.

Workup

  1. customwhile bubbling oxygen through the mixture at 100 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-34a6fe037e3d4d17a7fb839fa08a7e0a
Source dataset
uspto-grants-1995_08
Patent number
US05439813

Reaction notes

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