Trimethylolethane → Dimethylolpropionic acid

HRID 861812Notes

Reaction equation

HRID 861812 reaction equation
P([O-])([O-])([O-])=[O:2].[K+].[K+].[K+].[OH:9][CH2:10][C:11]([CH2:15][OH:16])([CH2:13][OH:14])[CH3:12]>>[OH:14][CH2:13][C:11]([CH2:15][OH:16])([CH3:12])[CH:10]=[O:9].[OH:9][CH2:10][C:11]([CH2:15][OH:16])([CH3:12])[C:13]([OH:2])=[O:14]

Participants

4

Reactant 2

HCID 6502Trimethylolethane2×HCID 62657Potassium Phosphate, Tribasic

Product 2

HCID 78501Dimethylolpropionic acidHCID 87688Propanal, 3-hydroxy-2-(hydroxymethyl)-2-methyl-

Conditions

Temperature
30 °C

Procedure

One loopful bacterial cells of Agrobacterium sp. SD807 strain were inoculated in 5 ml of a culture medium having the same composition as culture medium 2 shown in Table 3 and incubated with shaking at 30° C. for 1 day. After completion of the cultivation, the bacterial cells were harvested by centrifugation and a 50 mM potassium phosphate buffer solution containing 1,1,1-tris(hydroxymethyl)ethane in a concentration of 5 g/l was added thereto to prepare a resting cell suspension reaction mixture. This was shaken at 30° C. The reaction mixture had a turbidity in terms of absorbance of 0.2 at 660 nm. A portion of the reaction mixture was analyzed by high performance liquid chromatography and as a result, it was found that 4.9 g/l of 1,1,1-tris(hydroxymethyl)ethane had been oxidized at 66 hours of the reaction to produce 0.1 g/l of 2,2-bis (hydroxymethyl)propionaldehyde and 4.8 g/l of 2,2-bis (hydroxymethyl)propionic acid. Conversion rate of 1,1,1-tris(hydroxymethyl)ethane to 2,2-bis(hydroxymethyl)propionic acid was about 88%.

Workup

  1. additionwas added
  2. customto prepare
  3. customa resting cell suspension reaction mixture
  4. stirringThis was shaken at 30° C
  5. customhad been oxidized at 66 hours of the reaction

Sources & evidence

ORD record
ord-fe878ad13bb646cb8fadb1fb5cdd52b0
Source dataset
uspto-grants-1998_02
Patent number
US05716815

Reaction notes

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