Acetaldehyde → N-(1-methoxyethyl)acetamide

HRID 1276835

Reaktionsgleichung

Reaktionsgleichung von HRID 1276835
[C:1]([NH2:4])(=[O:3])[CH3:2].[CH:5]([NH:7][C:8](=[O:10])[CH3:9])=[CH2:6].[CH3:11][O:12][CH:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14].C(=O)C>O.CO>[CH3:11][O:12][CH:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14].[C:1]([NH2:4])(=[O:3])[CH3:2].[CH3:11][O:12][CH:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14].[CH:5]([NH:7][C:8](=[O:10])[CH3:9])=[CH2:6]

Komponenten

8

Edukt 4

HCID 177Acetaldehyde3×HCID 178Acetamide3×HCID 78875N-Vinylacetamide3×HCID 10986197N-(1-methoxyethyl)acetamide2×

Produkt 2

HCID 10986197N-(1-methoxyethyl)acetamideHCID 22116799acetamide N-(1-methoxyethyl)acetamide N-vinylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittel5×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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%.

Aufarbeitung

  1. customA mixture was prepared
  2. additionThe components were thoroughly mixed
  3. customto prepare the reaction
  4. customthereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm
  5. additionfilled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark)
  6. customThe reaction results
  7. customafter neutralization of the reaction solution obtained through the outlet at the bottom of the reactor
  8. customresults after 7 hours

Quellen und Nachweise

ORD-Eintrag
ord-951a51b0d8554316b4629ad867d22f5d
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166253

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