Glycolic Acid → Glyoxylic Acid

HRID 1736279Notes

Reaction equation

HRID 1736279 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)O.C(O)(=[O:16])C(C)C.[OH-].[Na+].[C:20]([O-:24])(=[O:23])[CH2:21][OH:22].O=O>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:21]([OH:16])(=[O:22])[C:20]([OH:24])=[O:23]

Participants

8

Reactant 6

HCID 757Glycolic AcidHCID 977OxygenHCID 6590Isobutyric AcidHCID 14017(Aminomethyl)phosphonic acidHCID 14798Sodium Hydroxide2×HCID 5460308Hydroxyacetate

Product 2

HCID 760Glyoxylic AcidHCID 971Oxalic Acid

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. To the reactor was then added 15 g of frozen (-80° C.) Aspergillus nidulans FT17SYCSL/OL (72 IU glycolate oxidase and 33,300 IU catalase) and 1.4×106 units of Aspergillus niger soluble catalase (Sigma), the cells allowed to thaw at 5° C., and the pH of the resulting mixture re-adjusted to 8.3 with 50% NaOH. This mixture was stirred at 400 rpm and 5° C. under 120 psig of oxygen while bubbling oxygen through the mixture at 50 mL/min. After 17 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 76%, 0%, and 4.1%, respectively, with 16.8% recovery of glycolic acid. The final activities of glycolate oxidase and Aspergillus niger catalase were 7% and 49% of their initial values.

Workup

  1. additionTo the reactor was then added 15 g
  2. temperatureof frozen (-80° C.)
  3. customthaw at 5° C.
  4. customwhile bubbling oxygen through the mixture at 50 mL/min

Sources & evidence

ORD record
ord-889d40630ef74b57989993b10c62358f
Source dataset
uspto-grants-1996_07
Patent number
US05541094

Reaction notes

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