Hydrochloric Acid → Glycolic Acid

HRID 1934303Notes

Reaction equation

HRID 1934303 reaction equation
P([O-])([O-])([O-])=[O:2].[K+].[K+].[K+].[C:9](#[N:12])[CH2:10][OH:11].Cl.[OH2:14]>>[C:9](#[N:12])[CH2:10][OH:11].[C:10]([OH:11])(=[O:2])[CH2:9][OH:14].[C:9]([NH2:12])(=[O:14])[CH2:10][OH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7857Hydroxyacetonitrile2×HCID 62657Potassium Phosphate, Tribasic

Product 3

HCID 757Glycolic AcidHCID 7857HydroxyacetonitrileHCID 690212-Hydroxyacetamide

Procedure

The reaction described in Example 1 is repeated except that the mutant strains A. facilis 72-PF-15 or 72-PF-17 are used instead of A. facilis 72W. A suspension of 0.50 g (wet cell paste) A. facilis 72-PF-15 or 72-PF-17 in 8.44 mL of 0 020 M potassium phosphate buffer (pH 6.0) is placed into a 15-mL polypropylene centrifuge tube. To the tube is then added 1.06 mL of a 55 wt % solution of glycolonitrile in water (1.0 M final concentration of glycolonitrile in the suspension), and the resulting suspension mixed on a rotating platform at 25° C. Samples of the suspension for analysis (0.200 mL) are first adjusted to pH 2.5 with 6 N HCl to stop the reaction, centrifuged, and the supernatant filtered using a 0.2 micron filter. After sufficient time, complete conversion of glycolonitrile to glycolic acid is obtained with no production of byproduct glycolamide.

Workup

  1. additionA suspension of 0.50 g (wet cell paste) A
  2. additionmixed on a rotating platform at 25° C
  3. customthe reaction
  4. filtrationthe supernatant filtered
  5. filtrationfilter

Sources & evidence

ORD record
ord-d34f6d0544494e0491cc6e75e55af3b7
Source dataset
uspto-grants-2002_05
Patent number
US06383786B1

Reaction notes

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