Copper catalyzed amination of ethylene glycol

• Published in: Applied catalysis Vol. 17; no. 2; pp. 309 - 319
• Main Authors: Runeberg, Johan, Baiker, Alfons, Kijenski, Jacek
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.08.1985; Elsevier
• Subjects: Chemical reactivity; Chemistry; Exact sciences and technology; Organic chemistry; Reactivity and mechanisms; Diamine; Catalytic reaction; Temperature; Aminoalcohol; Amination; Enamine; Selectivity; Copper; Alumina; Supported catalyst; Glycol
• ISSN: 0166-9834
• DOI: 10.1016/S0166-9834(00)83211-X

The amination of ethylene glycol by dimethylamine on alumina supported copper has been studied in a continuous fixed-bed reactor at atmospheric pressure. Main reaction products were 2-dimethylaminoethanol, N,N,N′,N′-tetramethyl-1,2-diaminoethene (enamine) and N,N,N′,N′-tetramethylethylenediamine (diamine). The selectivity to 2-dimethylaminoethanol exhibited a maximum at 230°C, reaching more than 70 wt%. Selectivities to the enamine and to the diamine were much lower and did not show a maximum in the range 190° – 250°C. Ethylene glycol conversion was virtually independent of the hydrogen partial pressure and of the reactant ratio, dimethylamine : glycol, in the range 1.25 – 2.25. In contrast, the selectivities to 2-dimethylaminoethanol and to the enamine were markedly influenced when the reactant ratio was changed in this range. The selectivity to the enamine could be increased to 55 %, when hydrogen was substituted by nitrogen in the feed.