Journal of Japan Oil Chemists' Society
Online ISSN : 1884-2003
ISSN-L : 0513-398X
Studies on Alkyl Ketene Dimers. III.
Reactions of Alkyl Ketene Dimer and Amine Compounds
Ichiro IMAITakeo WAKABAYASHI
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JOURNAL FREE ACCESS

1961 Volume 10 Issue 3 Pages 165-168

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Abstract

Reaction products of tetradecyl ketene dimer and amine compounds were investigated. As the amine compounds, NH3 (I), CH3NH2 (II), C6H5NH2 (III), H2NC2H4OH (IV), NH (C2H4OH) 2 (V) were used. One mol of tetradecyl ketene dimer was reacted with two mols of amine compounds.
By reacting (I) in the medium of benzene at 40 to 45°C, 2-tetradecyl-3-keto-octadecanoic-acid amide (mp 118.1118.4°C) was obtained with about 88 percent yield. When reacted in the medium of water, same product was obtained.
By reacting (II) in the medium of benzene at 40 to 45°C, 2-tetradecyl-3-keto octadecanoic-acid N-methyl amide (mp 103.0103.5°C) was obtained with theoretical yield.
By reacting (III), (IV) and (V) in the medium of ethyl ether, 2-tetradecyl-3-keto-octadecanoic-acid anilide (mp 95.695.8°C), N-monoethanol amide (mp 109.5109.9°C) and diethanol amide (mp 35.435.8°C) were obtained. The yields were about 80, 80 and 75 percent respectively.
Reaction products were identified by ultimate analysis and infrared spectrophotometer.

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