Issue 56, 2016

Methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to dimethylhexane-1,6-dicarbamate over Zn/SiO2 catalyst

Abstract

The heterogeneous Zn/SiO2 catalysts for the synthesis of dimethylhexane-1,6-dicarbamate (HDC) from 1,6-hexanediamine (HDA) and dimethyl carbonate (DMC) were prepared by incipient impregnation. The catalysts were characterized by BET, TG, FT-IR, TEM and XPS, and the results revealed that the activated Zn(OAc)2 in catalysts was responsible for the main active sites for the reaction. The Zn/SiO2(300) catalyst exhibited the best catalytic performance with HDA conversion of 96.0% and HDC yield of 68.5% owing to the most amount of activated Zn(OAc)2 and the highest binding energy of Zn 2p3/2. No obvious deactivation on the catalyst was found after 5 recycles due to the appropriate interaction between Zn(OAc)2 and SiO2. In addition, the results of in situ FT-IR experiments revealed that DMC was activated by the catalyst to form a stable intermediate that was then attacked by HDA with a typical nucleophilic addition–elimination reaction to produce HDC.

Graphical abstract: Methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to dimethylhexane-1,6-dicarbamate over Zn/SiO2 catalyst

Supplementary files

Article information

Article type
Paper
Submitted
02 Apr 2016
Accepted
18 May 2016
First published
20 May 2016

RSC Adv., 2016,6, 51446-51455

Methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to dimethylhexane-1,6-dicarbamate over Zn/SiO2 catalyst

L. Zhang, H. Li, F. Li, Y. Pu, N. Zhao and F. Xiao, RSC Adv., 2016, 6, 51446 DOI: 10.1039/C6RA08492C

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