Acetic Acid → Methyl diacetate

HRID 1588084Notes

Reaction equation

HRID 1588084 reaction equation
[C:1]([O:4][CH3:5])(=[O:3])[CH3:2].O1CCCOO1.[C:12]([OH:15])(=[O:14])[CH3:13].I.[C]=O>>[C:1]([O:4][CH2:5][O:15][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6584Methyl AcetateHCID 24841Hydrogen iodideHCID 19593658CID 19593658HCID 178418416HCID 178418416, compound

Product 1

HCID 12345Methyl diacetate

Conditions

Temperature
200 °C

Procedure

A 1-liter, magnetically stirred autoclave was charged with 0.001 mol of Rh(CO)2Cl, sealed and flushed with nitrogen followed by carbon monoxide. The autoclave was then charged with 1 mol of methyl acetate, 1 mol of trioxane, 0.5 mol of acetic acid and 0.056 mol of hydrogen iodide. The autoclave was sealed, pressured to 1000 psig with carbon monoxide, and rapidly heated to 200° C. After 16 hours at 200° C., the reaction was terminated, the autoclave was opened and the reaction mixture analyzed by nuclear magnetic resonance spectroscopy, infrared spectroscopy and gas-liquid chromatography. The conversion of methyl acetate was 49% and the yield of methylene bis-acetate, ##STR9## based on converted methyl acetate, was 28%.

Workup

  1. customsealed
  2. customflushed with nitrogen
  3. customThe autoclave was sealed
  4. customthe reaction was terminated

Sources & evidence

ORD record
ord-ddd92e3bb08c4a8595afc1df43f64750
Source dataset
uspto-grants-1993_06
Patent number
US05220060

Reaction notes

Loading…