CH3COONa As An Effective Catalyst For Methoxycarbonylation Of 1,6 ...

Jump to main content Jump to site search Issue 3, 2010

• Previous Article
• Next Article

From the journal:

Green Chemistry

CH3COONa as an effective catalyst for methoxycarbonylation of 1,6-hexanediamine by dimethyl carbonate to dimethylhexane-1,6-dicarbamate†

Da-Lei Sun,ac Shun-Ji Xie,a Jian-Ru Deng,a Cai-Juan Huang,a Eli Ruckenstein*b and Zi-Sheng Chao*a Author affiliations

* Corresponding authors

a College of Chemistry and Chemical Engineering; Key Laboratory of Chemometrics & Chemical Biological Sensing Technologies, Ministry of Education, Hunan University, Changsha, China E-mail: [email protected] Tel: +86-731-8713257

b Department of Chemical and Biological Engineering, State University of New York at Buffalo, Buffalo, NY, USA E-mail: [email protected] Tel: +1-716-6451179

c Department of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, China

Abstract

Methoxycarbonylation of 1,6-hexanediamine (HDA) by dimethyl carbonate (DMC) was carried out, using, for the first time, CH3COONa as catalyst. The effects of the solvent, reaction temperature, reaction time, and catalyst amount, were investigated. A yield as high as 99.0% of dimethylhexane-1,6-dicarbamate 2 has been obtained at a temperature of 348 K and a reaction time of 6 h. Mechanistic studies revealed that N-substituted acetamide, as the active intermediate product, and NaOH were first formed via the reaction between HDA and CH3COONa. A further reaction between the N-substituted acetamide and DMC generated carbamates and methyl acetate, via a hexatomic ring intermediate. The CH3COONa catalyst was finally recovered through the reaction between NaOH and methyl acetate, which thus completed the catalytic cycle.

You have access to this article Please wait while we load your content... Something went wrong. Try again? About Cited by Related Download options Please wait...

Supplementary files

• Experimental data PDF (335K)

Article information

DOI https://doi.org/10.1039/B915023B Article type Paper Submitted 17 Apr 2009 Accepted 06 Jan 2010 First published 28 Jan 2010

Download Citation

Green Chem., 2010,12, 483-490 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS

Permissions

Request permissions

CH3COONa as an effective catalyst for methoxycarbonylation of 1,6-hexanediamine by dimethyl carbonate to dimethylhexane-1,6-dicarbamate

D. Sun, S. Xie, J. Deng, C. Huang, E. Ruckenstein and Z. Chao, Green Chem., 2010, 12, 483 DOI: 10.1039/B915023B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Tweet Share

Search articles by author

Da-Lei Sun Shun-Ji Xie Jian-Ru Deng Cai-Juan Huang Eli Ruckenstein Zi-Sheng Chao

Fetching data from CrossRef. This may take some time to load.

Loading related content

Spotlight

Advertisements

This website collects cookies to deliver a better user experience. See how this site uses Cookies. Do not sell my personal data. Este site coleta cookies para oferecer uma melhor experiência ao usuário. Veja como este site usa Cookies. Publishing

Journals

• Current Journals
• Archive Journals
• All Journals

Books

• Browse Books
• Series
• For Authors and Editors
• About

Databases

• Literature Updates
• ChemSpider
• The Merck Index*
• MarinLit

More

• For Members
• For Librarians
• Subscribe
• RSS Feeds
• Blogs
• Chemistry World
• Education in Chemistry
• Open Access
• Historical Collection