Acetic Acid → Ethylene glycol diacetate

HRID 1763701

Reaction equation

HRID 1763701 reaction equation
[I-].[K+].[N+]([O-])(O)=O.O=O.[CH2:9]=[CH2:10].[C:11]([OH:14])(=[O:13])[CH3:12]>>[CH3:12][C:11]([O:14][CH2:9][CH2:10][O:14][C:11]([CH3:12])=[O:13])=[O:13]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 944Nitric AcidHCID 977OxygenHCID 4875Potassium IodideHCID 6325Ethylene2×

Product 1

HCID 8121Ethylene glycol diacetate

Conditions

Temperature
65 °C

Procedure

To a reactor similar to that described in Example 1 were added 3.3 g (20 millimoles) of potassium iodide, 1 ml (10 millimoles) of nitric acid, 0.5 g of activated carbon prepared from coconut shells (manufactured by Dai-ichi Carbon Industries Company) and 80 ml of acetic acid. The flask was set up in an oil bath maintained at 65° C. A gas mixture comprising by volume 8.5% of oxygen, 80% of nitrogen and 11.5% of ethylene was fed through the reaction mixture at a rate of 1.15 standard liters per hour with continuous stirring of the reaction mixture. At the conclusion of the one hour reaction period, the conversion of ethylene was 90%. The combined yields of EGDA and EGMA were 95% based on the reacted ethylene. Trace amounts of EDA and AcH were detected as by-products.

Workup

  1. customTo a reactor similar to that described in Example 1
  2. customThe flask was set up in an oil bath
  3. customAt the conclusion of the one hour reaction period

Sources & evidence

ORD record
ord-725c87b1607a4b98935edf18f307b755
Source dataset
uspto-grants-1978_09
Patent number
US04112241

Linked notes

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