Ethoxylation of fatty amines

Abstract

Abstract It is well known that long chain alcohols and phenols cannot react with ethylene oxide in the absence of catalysts, whereas primary fatty amines can take up at least two moles of oxide to form tertiary amines. It has been found that further ethoxylation of this two mole adduct in the absence of added catalyst can proceed only if ethoxylation temperatures are lowered considerably. The present paper demonstrates that this low‐temperature ethoxylation is really catalyzed by a previously overlooked highly alkaline compound generated during the course of the reaction. It is shown that this is a long‐chain quaternary ammonium compound, and the mechanism of its formation is described. As the addition of ethylene oxide proceeds, this quaternary gradually decomposes and the reaction essentially comes to a halt when it has all disappeared.