Acetic Acid → 2-Acetoxypropionic Acid

HRID 1612394Notes

Reaction equation

HRID 1612394 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:11])(=[O:10])[CH:7]([CH3:9])[OH:8].O.[C:13](O)(=[O:15])[CH3:14]>>[C:13]([O:8][CH:7]([CH3:9])[C:6]([OH:11])=[O:10])(=[O:15])[CH3:14]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 612Lactic AcidHCID 962WaterHCID 1118Sulfuric Acid

Product 1

HCID 790412-Acetoxypropionic AcidYield 90%

Conditions

Temperature
114 °C

Procedure

In a distillation reactor at atmospheric pressure, an acid solution formed by combining 30 ml of glacial acetic acid with 0.5 ml concentrated sulfuric acid was maintained at approximately 114° C. A reactant solution was prepared by combining 5.0 ml of an 85% lactic acid solution, by weight (15% water) with 20 ml of glacial acetic acid, and was added dropwise to the distillation reactor. The resulting distillate was collected and analyzed by NMR. After 1 hour, the 2-acetoxy propionic acid product yield was greater than about 90%. A small amount of dimer or polymer was also detected.

Workup

  1. customIn a distillation reactor at atmospheric pressure, an acid solution formed
  2. customA reactant solution was prepared
  3. distillationThe resulting distillate was collected

Sources & evidence

ORD record
ord-4ca010ffde294b79897b8753381f0c83
Source dataset
uspto-grants-2006_01
Patent number
US06992209B2

Reaction notes

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