Glycolic Acid → Glyoxylic Acid

HRID 1755973Notes

Reaction equation

HRID 1755973 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]>C(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 4

HCID 757Glycolic AcidHCID 1032Propionic AcidHCID 3301EthylenediamineHCID 5460308Hydroxyacetate

Product 2

HCID 760Glyoxylic AcidHCID 971Oxalic Acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The reaction in Example 4 was repeated using 10 mL of a solution containing glycolic acid (0.75M), ethylenediamine (0.86M), propionic acid (0.075M, HPLC internal standard), flavin mononucleotide (0.2 mM), 2.5 IU of spinach glycolate oxidase immobilized on Eupergit C, and 14,000 IU of Aspergillus niger catalase immobilized on Eupergit C (the two enzymes were not co-immobilized on the same support). After 20 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 99%, 0.2%, and 0.5%, respectively, with a 100% conversion of glycolic acid. The final activities of glycolate oxidase and catalase were 72% and 66% of their initial values, respectively.

Workup

  1. customThe reaction in Example 4

Sources & evidence

ORD record
ord-c1a3c8d317d54126b2a17e6accc6c639
Source dataset
uspto-grants-1995_08
Patent number
US05439813

Reaction notes

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