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Enzymatic synthesis of N-alkanoyl-N-methylglucamide surfactants: solvent-free production and environmental assessment

Gaber, Yasser LU ; Törnvall, Ulrika LU ; Orellana Coca Åkerman, Cecilia LU ; Amin, Magdy Ali and Hatti-Kaul, Rajni LU (2010) In Green Chemistry 12(10). p.1817-1825
Abstract
A biocatalysis based method for the solvent-free production of N-alkanoyl-N-methylglucamide (MEGA) surfactants was developed and used as a case study for the evaluation of different environmental assessment tools, such as the freeware package EATOS (Environmental Assessment Tool for Organic Synthesis). In order to also consider energy usage and process facilities, e. g. heating, stirring and vacuum, a complementary tool was needed; hence the EcoScale method and the use of an energy monitoring socket were also exploited. The solvent-free method followed by a simple hydrolysis step gave a final amide yield of 99% and a product essentially free of remaining substrate, N-methylglucamine (MEG). The latter is important since MEG can potentially... (More)
A biocatalysis based method for the solvent-free production of N-alkanoyl-N-methylglucamide (MEGA) surfactants was developed and used as a case study for the evaluation of different environmental assessment tools, such as the freeware package EATOS (Environmental Assessment Tool for Organic Synthesis). In order to also consider energy usage and process facilities, e. g. heating, stirring and vacuum, a complementary tool was needed; hence the EcoScale method and the use of an energy monitoring socket were also exploited. The solvent-free method followed by a simple hydrolysis step gave a final amide yield of 99% and a product essentially free of remaining substrate, N-methylglucamine (MEG). The latter is important since MEG can potentially be converted to carcinogenic nitrosamines. The absence of solvent in the reaction medium was also found to result in a significantly reduced potential environmental impact. The environmental tools used in this study were further scrutinized, and even if they represent some of the best freely available tools for evaluation of early stage process development, some points for further improvements are suggested. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Green Chemistry
volume
12
issue
10
pages
1817 - 1825
publisher
Royal Society of Chemistry
external identifiers
  • wos:000282586000020
  • scopus:78149448787
ISSN
1463-9270
DOI
10.1039/c004548a
language
English
LU publication?
yes
id
29a41265-086c-4208-b4b9-0cc108bc7cd2 (old id 1727220)
date added to LUP
2010-11-26 14:21:28
date last changed
2018-05-29 10:27:52
@article{29a41265-086c-4208-b4b9-0cc108bc7cd2,
  abstract     = {A biocatalysis based method for the solvent-free production of N-alkanoyl-N-methylglucamide (MEGA) surfactants was developed and used as a case study for the evaluation of different environmental assessment tools, such as the freeware package EATOS (Environmental Assessment Tool for Organic Synthesis). In order to also consider energy usage and process facilities, e. g. heating, stirring and vacuum, a complementary tool was needed; hence the EcoScale method and the use of an energy monitoring socket were also exploited. The solvent-free method followed by a simple hydrolysis step gave a final amide yield of 99% and a product essentially free of remaining substrate, N-methylglucamine (MEG). The latter is important since MEG can potentially be converted to carcinogenic nitrosamines. The absence of solvent in the reaction medium was also found to result in a significantly reduced potential environmental impact. The environmental tools used in this study were further scrutinized, and even if they represent some of the best freely available tools for evaluation of early stage process development, some points for further improvements are suggested.},
  author       = {Gaber, Yasser and Törnvall, Ulrika and Orellana Coca Åkerman, Cecilia and Amin, Magdy Ali and Hatti-Kaul, Rajni},
  issn         = {1463-9270},
  language     = {eng},
  number       = {10},
  pages        = {1817--1825},
  publisher    = {Royal Society of Chemistry},
  series       = {Green Chemistry},
  title        = {Enzymatic synthesis of N-alkanoyl-N-methylglucamide surfactants: solvent-free production and environmental assessment},
  url          = {http://dx.doi.org/10.1039/c004548a},
  volume       = {12},
  year         = {2010},
}