Trimethylsilyldiazomethane: A safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications

T.J van 't Erve; R.H Rautiainen; L.W Robertson; G Luthe

doi:10.1016/j.envint.2010.02.011

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Trimethylsilyldiazomethane: A safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications

Journal article

Peer reviewed

Trimethylsilyldiazomethane: A safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications

T.J van 't Erve, R.H Rautiainen, L.W Robertson and G Luthe

Environment international, Vol.36(8), pp.835-842

2010

DOI: 10.1016/j.envint.2010.02.011

PMCID: PMC4090112

PMID: 20385409

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https://doaj.org/article/03b1581eca9542f985f7568ddb8ee74dView

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Abstract

Diazomethane is a highly explosive and toxic gas routinely employed for the quantitative and clean derivatization of phenols. We investigated the commercially available trimethylsilyldiazomethane in the presence of diisopropylethylamine as a safe, non-explosive and less-toxic alternative using six phenolic polychlorinated biphenyls as model analytes and fluoro-tagged analogues as internal standards. We compared yields and derivatization times of each method employing a liver microsomal extract as a real matrix. Steric hindrance and electronic properties of the analytes were also investigated. The alternative method afforded equal to higher derivatization yields with increased reaction times, up to 100 min, while explosion and toxic exposure risks were minimized and cost efficiency was increased above 25%. These findings demonstrate that non-explosive trimethylsilyl diazomethane produces comparable derivatization results to the dangerous diazomethane under the conditions studied.

Phenols

O-methylation

Hydroxylated polychlorinated biphenyls

Diazocompounds

Derivatization

Diazomethane

Details

Title: Subtitle: Trimethylsilyldiazomethane: A safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications
Creators: T.J van 't Erve - Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA, United States
R.H Rautiainen - Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA, United States
L.W Robertson - Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA, United States
G Luthe - Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA, United States
Resource Type: Journal article
Publication Details: Environment international, Vol.36(8), pp.835-842
DOI: 10.1016/j.envint.2010.02.011
PMID: 20385409
PMCID: PMC4090112
NLM abbreviation: Environ Int
ISSN: 0160-4120
eISSN: 1873-6750
Publisher: Elsevier Ltd
Language: English
Date published: 2010
Academic Unit: Occupational and Environmental Health
Record Identifier: 9984002431602771

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