Ethanol → Ethyl 3-ethoxypropionate

HRID 1709355

Reaction equation

HRID 1709355 reaction equation
O.[OH-].[Na+].[C:4]([O:8][CH2:9][CH3:10])(=[O:7])[CH:5]=[CH2:6].[CH2:11]([OH:13])[CH3:12]>CO.CO.C(O)C>[CH3:11][O:13][CH2:6][CH2:5][C:4]([O:8][CH2:9][CH3:10])=[O:7].[CH2:11]([O:13][CH2:6][CH2:5][C:4]([O:8][CH3:9])=[O:7])[CH3:12].[CH2:11]([O:13][CH2:6][CH2:5][C:4]([O:8][CH2:9][CH3:10])=[O:7])[CH3:12].[CH3:11][O:13][CH2:6][CH2:5][C:4]([O:8][CH3:9])=[O:7]

Participants

10

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 8821Ethyl AcrylateHCID 14798Sodium Hydroxide

Product 4

HCID 12989Ethyl 3-ethoxypropionateHCID 19710Methyl 3-methoxypropionateHCID 82767Propanoic acid, 3-methoxy-, ethyl esterHCID 14876011Methyl 3-ethoxypropanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A 50 cm long, 5 cm diameter water-jacketted reactor (Reactor C) was charged with 1 liter of Dowex MSA 1 strong base resin. The resin was treated in sequence with 2000 ml of ethanol, 2000 ml of water, 3800 ml of 4 weight percent aqueous sodium hydroxide, and 5000 ml of methanol-ethanol mixture. This reactor was used to react mixtures containing ethyl acrylate and both methanol and ethanol to produce mixtures of ethyl 3-methoxypropanoate, methyl 3-ethoxypropanoate, ethyl 3-ethoxypropanoate and methyl 3-methoxypropanoate. In each run about 7.5 liters of a feed solution containing the components identified in Table IV was used. There was no problem of ethyl acrylate breakthrough at the end of each run. The mixture was recovered by distillation to remove the alcohols.

Workup

  1. additionwas charged with 1 liter of Dowex MSA 1 strong base resin
  2. customThis reactor was used
  3. customto react mixtures

Sources & evidence

ORD record
ord-a3d1abebb6e4430795f146056341db88
Source dataset
uspto-grants-1990_08
Patent number
US04948915

Linked notes

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