Butyric Acid → Formate

HRID 1646707Notes

Reaction equation

HRID 1646707 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)[OH:9].[C:12]([OH:17])(=[O:16])CCC.[C:18]([O-:22])(=[O:21])[CH2:19][OH:20]>>[C:1]([O-:5])(=[O:4])[CH:2]=[O:3].[CH:12]([O-:17])=[O:16].[C:19]([O-:9])(=[O:20])[C:18]([O-:22])=[O:21]

Participants

7

Conditions

Temperature
5 °C

Procedure

Into a 3 oz. Fischer-Porter glass aerosol reaction vessel was placed a magnetic stirring bar and 10 mL of an aqueous solution containing glycolic acid (0.50M), aminomethylphosphonic acid (AMPA, 0.40 m), FMN (0.01 mM), butyric acid (HPLC internal standard, 0.10M), glycolate oxidase (from spinach, 1.0 IU/mL), and catalase (from Aspergillus niger, 14,000 IU/mL) at pH 8.5. The reaction vessel was sealed and the reaction mixture was cooled to 5° C., then the vessel was flushed with oxygen by pressurizing to 70 psig and venting to atmospheric pressure five times with stirring. The vessel was then pressurized to 70 psig of oxygen and the mixture stirred at 5° C. Aliquots (0.10 mL) were removed by syringe through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC to monitor the progress of the reaction. After 17.5 h, the HPLC yields of glyoxylate, formate, and oxalate were 91.0%, 2.9%, and 2.9%, respectively, and 4.1% glycolate remained. The final pH of the reaction mixture was 6.7.

Workup

  1. customFischer-Porter glass aerosol reaction vessel
  2. customThe reaction vessel was sealed
  3. customthe vessel was flushed with oxygen
  4. stirringthe mixture stirred at 5° C
  5. customAliquots (0.10 mL) were removed by syringe through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC
  6. customthe progress of the reaction

Sources & evidence

ORD record
ord-2150bfc4c4f84eed8a31e804d359d183
Source dataset
uspto-grants-1993_01
Patent number
US05180846

Reaction notes

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