Research on the N-alkylation of morpholine with alcohols catalyzed by CuO–NiO/γ–Al2O3

Abstract

The N-alkylation of morpholine with alcohols in gas-solid phase was investigated in a fixed-bed reactor over CuO-NiO/c-Al 2 O 3 catalyst prepared by the impregnation method. The N-methylation of morpholine with methanol gave a 95.3% conversion with a 93.8% selectivity of N-methylmorpholine under the optimum reaction condition, and the corresponding apparent activation energy is 46.20 kJ mol -1 . The present catalytic system is also applicable to other low-carbon primary alcohols. However, secondary alcohols enjoy relatively low product selectivity for the resulting ketone is a poorer electrophile than an aldehyde. For cyclohexanol, the low conversion and selectivity are mainly due to steric effects. The catalyst shows a high catalytic activity without obvious fluctuation during a long period of 120 h.

Synthesis and Characterization of Nano CuO-NiO Mixed Oxides

“…In addition pure and doped copper-nickel mixed oxides have been investigated [37][38][39][40]. CuO-NiO supported γ-Al 2 O 3 was efficiently used in N-Alkylation of ethylenediamine [41] and morphine [42] with alcohols.…”

Study on deactivation of the CuO‐NiO/γ‐Al2O3 catalyst in the synthesis of N‐alkylmorpholines

“…Compared with the homogeneously catalyzed system, the gas or liquid–solid heterogeneous system allows easier separation of catalysts and products. What is more, the heterogeneous catalyst, such as CuO‐NiO/γ‐Al 2 O 3 is not only with good activity and selectivity but also cheap and accessible . Lu studied the synthesis of cyclohexylamine with the CuO‐NiO/γ‐Al 2 O 3 catalyst and explored the effects of the reaction condition and the catalyst preparation on the reaction conversion and product selectivity.…”

Synthesis of N-Methylmorpholine from Morpholine and Dimethyl Carbonate

“…N-Methylmorpholine (NMM) is one kind of heterocyclic amine, it is significantly important in the bulk and fine chemical industry as versatile building blocks for pesticide, herbicide, fungicide, coolant lubricant, surfactant 1 . N-Methylmorpholine is also used as an extractive solvent and anticorrosive agent 2 .…”

“…With the growing wide range of applications, the development of efficient methods for the synthesis of N-methylmorpholine continues to be a challenging and active area of research. The conventional process is via methylating of morpholine with methyl halides but this process is limited due to the storage of the toxic methyl halides and byproduct waste salts 1 . The Nmethylation of morpholine by methanol was carried out by Zotto et al 5 and Chen et al 1 who used ruthenium complexes or CuO-NiO/γ-Al2O3 catalyst.…”

“…The conventional process is via methylating of morpholine with methyl halides but this process is limited due to the storage of the toxic methyl halides and byproduct waste salts 1 . The Nmethylation of morpholine by methanol was carried out by Zotto et al 5 and Chen et al 1 who used ruthenium complexes or CuO-NiO/γ-Al2O3 catalyst.…”