Glycolic Acid → Glyoxylic Acid

HRID 1736281Notes

Reaction equation

HRID 1736281 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)[OH:9].C(O)(=O)C(C)C.[OH-].[Na+]>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:2]([OH:9])(=[O:3])[C:1]([OH:5])=[O:4]

Participants

6

Conditions

Temperature
5 °C

Procedure

A 300-mL EZE-Seal stirred autoclave reactor (Autoclave Engineers) was charged with 100 mL of a solution containing glycolic acid (0.500M), aminomethylphosphonic acid (0.375M), isobutyric acid (0.100M, HPLC internal standard), and flavin mononucleotide (0.01 mM) at pH 8.3 (adjusted with 50% NaOH), and the solution cooled to 5° C. Freshly-harvested Aspergillus nidulans FT17SYCSL/OL (37 g, 44 IU glycolate oxidase and 57,800 IU catalase) were washed with 4×100 mL of KH2PO4 (50 mM, pH 7.0)/FMN (0.01 mM) buffer at 5° C. and the washed cells added to the reactor with 1.4×106 units of Aspergillus niger soluble catalase (Sigma). The pH of the resulting mixture was re-adjusted to 8.3 with 50% NaOH, then stirred at 400 rpm and 5° C. under 120 psig of oxygen while bubbling oxygen through the mixture at 50 mL/min. After 15 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 84%, 0%, and 9.4%, respectively, with 6.4% recovery of glycolic acid.

Workup

  1. washFreshly-harvested Aspergillus nidulans FT17SYCSL/OL (37 g, 44 IU glycolate oxidase and 57,800 IU catalase) were washed with 4×100 mL of KH2PO4 (50 mM, pH 7.0)/FMN (0.01 mM) buffer at 5° C.
  2. additionthe washed cells added to the reactor with 1.4×106 units of Aspergillus niger soluble catalase (Sigma)
  3. customwhile bubbling oxygen through the mixture at 50 mL/min

Sources & evidence

ORD record
ord-d6d4acdac10548d2850c5d210f3cd55f
Source dataset
uspto-grants-1996_07
Patent number
US05541094

Reaction notes

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