Document Detail

A derivatisation and liquid chromatography/electrospray ionisation multistage mass spectrometry method for the characterisation of naphthenic acids.
MedLine Citation:
PMID:  18988206     Owner:  NLM     Status:  MEDLINE    
Naphthenic acids (NAs) are partially uncharacterised complex mixtures of carboxylic acids, resulting from the microbial oxidation of petroleum hydrocarbons. They are associated with the fouling of pipelines and process equipment in oil production and with corrosion in oil refineries. As by-products of the rapidly expanding oil (tar) sands industries, NAs are also pollutants and have proved to be toxic to a range of organisms. They also have important beneficial uses as fungicides, tyre additives and, paradoxically, also in the manufacture of corrosion inhibitors. These features make the characterisation of NAs an important goal for analytical chemists. Here we describe the synthesis of amide derivatives of NAs for characterisation by liquid chromatography/electrospray ionisation multistage mass spectrometry (LC/ESI-MS(n)). The method was applied to commercially available carboxylic acids, novel synthetic NAs, commercial NAs refined from crude oils, crude oil NAs and Athabasca oil sands NAs. In addition to confirming the number of alicyclic rings and length of alkyl side chain substituents (confirming information from existing methods), the MS(n) results provided further structural information. Most important of these was the finding that bi- to polycyclic acids containing ethanoate side chains, in addition to alkyl substituents, were widespread amongst the oil and oil sands NAs. The latter NAs are known end members of the beta-oxidation of NAs with even carbon number alkanoate chains. Since such NA mixtures are toxic, they should be targets for bioremediation. Bioremediation of NAs can also be monitored better by application of the methods described herein.
B E Smith; S J Rowland
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  22     ISSN:  0951-4198     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2008 Dec 
Date Detail:
Created Date:  2008-11-17     Completed Date:  2009-05-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  3909-27     Citation Subset:  IM    
School of Earth, Ocean & Environmental Sciences, University of Plymouth, Drake Circus, Plymouth PL4 8AA, UK.
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MeSH Terms
Carboxylic Acids / analysis*,  chemical synthesis,  chemistry
Chromatography, Liquid / methods*
Nuclear Magnetic Resonance, Biomolecular / methods
Petroleum / analysis*
Solid Phase Extraction / methods
Spectrometry, Mass, Electrospray Ionization / methods*
Spectrophotometry, Infrared / methods
Tandem Mass Spectrometry / methods
Reg. No./Substance:
0/Carboxylic Acids; 0/Petroleum; 1338-24-5/naphthenic acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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