Acetaldehyde → N-(1-methoxyethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture was prepared containing 19.1 g of a mixture comprising 6.9 wt % acetamide, 57.4 wt % N-vinylacetamide and 35.6 wt % N-(1-methoxyethyl)acetamide (hereunder referred to as "NVA mixture"), 726.5 g of a mixture comprising 96.0 wt % dimethylacetal, 0.1 wt % acetaldehyde, 2.9 wt % methanol, 0.23 wt % water and 0.27 wt % hemiacetal (hereunder referred to as "acetal starting material"), 86.7 g of acetaldehyde, 126.7 g of methanol, 27.8 g of acetamide, 6.8 g of N-vinylacetamide and 9.9 g of water. The molar ratio of the N-vinylacetamide and the N-(1-methoxyethyl)acetamide, acetamide, acetal, acetaldehyde, water and methanol in the mixture was 1:0.36:2.4:37.2:9.7:3.1:22.3. In terms of "moieties" the proportion was "amide":"ethylidene":"methoxy":"water"=1:12.9:26.0:3.4. The components were thoroughly mixed to prepare the reaction starting solution, and 50 ml thereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm filled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark). Warm water at 40° C. was poured over the jacket of the reactor to maintain a reaction temperature of 40° C. The reaction results were calculated based on quantitative analysis by gas chromatography, after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor. Based on the reaction results after 7 hours, the N-(1-methoxyethyl)acetamide yield (with respect to acetamide+N-(1-methoxyethyl)acetamide+N-vinylacetamide) was 87.4%, and the ethylidene bisacetamide yield as a reaction by-product (calculated on the same standard as the N-(1-methoxyethyl)acetamide yield) was 5.2%.

Provenance & Evidence