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Catalysts screening, optimization and mechanism studies of dimethylhexane-1,6-dicarbamate synthesis from 1,6-hexanediamine and dimethyl carbonate over Mn(OAc)(2) catalyst
Zhao, Liyan1,2; He, Peng1; Wang, Liguo1; Ammar, Muhammad1,2; Cao, Yan1; Li, Huiquan1
2017-03-01
Source PublicationCATALYSIS TODAY
ISSN0920-5861
Volume281Pages:392-401
Abstract

The catalytic synthesis of dimethylhexane-1,6-dicarbamate (HDC) from 1,6-hexanediamine (HDA) and dimethyl carbonate (DMC) over a series of homogeneous catalysts (e.g., metallic nitrates and acetates) were investigated. Mn(OAc)(2) was found to be the most effective catalyst for this reaction. Under the optimum reaction conditions (reaction temperature of 363 K, DMC-to-HDA molar ratio of 4:1, catalyst concentration of 7 wt% (based on HDA), and reaction time of 5 h), HDC yield can reach as high as 98.0% with HDA totally converted. Online in-situ Fourier Transform Infrared (FTIR) and Density Functional Theory (DFT) calculations were used together to investigate the interactions between Mn(OAc)(2) and substrates. The results indicated that both of HDA and DMC had interactions with Mn(OAc)(2), but the energy barriers of the transition states (TS) of DMC (DMC-TS) was higher than that of HDA (HDA-TS), which meant that HDA was easier to interact with Mn(OAc)(2) to form new complex than DMC. The whole process can be proposed that, the new species II, which was formed by the interaction of HDA and Mn(OAc)(2), attacked carbonyl carbon of DMC to generate intermediate HMC and finally to HDC. The experimental data and calculation results are in good agreement with each other. (C) 2016 Elsevier B.V. All rights reserved.

KeywordDimethyl Carbonate (Dmc) Mechanism Dimethylhexane-1 Homogeneous Catalyst 6-dicarbamate (Hdc)
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences ; Technology
DOI10.1016/j.cattod.2016.02.059
Indexed BySCI
Language英语
WOS KeywordZinc Acetate ; Polyatomic-molecules ; Diethyl Carbonate ; Transition-states ; Alkyl Carbamate ; Methoxycarbonylation ; 1,6-hexamethylenediamine ; Dicarbamate ; Methanol ; Dioxide
WOS Research AreaChemistry ; Engineering
WOS SubjectChemistry, Applied ; Chemistry, Physical ; Engineering, Chemical
WOS IDWOS:000390623300020
Citation statistics
Cited Times:9[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/21862
Collection湿法冶金清洁生产技术国家工程实验室
Affiliation1.Chinese Acad Sci, Key Lab Green Proc & Engn, Natl Engn Lab Hydromet Cleaner Prod Technol, Inst Proc Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhao, Liyan,He, Peng,Wang, Liguo,et al. Catalysts screening, optimization and mechanism studies of dimethylhexane-1,6-dicarbamate synthesis from 1,6-hexanediamine and dimethyl carbonate over Mn(OAc)(2) catalyst[J]. CATALYSIS TODAY,2017,281:392-401.
APA Zhao, Liyan,He, Peng,Wang, Liguo,Ammar, Muhammad,Cao, Yan,&Li, Huiquan.(2017).Catalysts screening, optimization and mechanism studies of dimethylhexane-1,6-dicarbamate synthesis from 1,6-hexanediamine and dimethyl carbonate over Mn(OAc)(2) catalyst.CATALYSIS TODAY,281,392-401.
MLA Zhao, Liyan,et al."Catalysts screening, optimization and mechanism studies of dimethylhexane-1,6-dicarbamate synthesis from 1,6-hexanediamine and dimethyl carbonate over Mn(OAc)(2) catalyst".CATALYSIS TODAY 281(2017):392-401.
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