Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands
RATIONALE Naphthenic acids (NAs) accumulate in oil sands process‐affected water (OSPW) as a result of the water‐based extraction processes, and represent one of the toxic fractions in OSPW. They exist as a complex mixture and so the development of an analytical method to characterize and quantify in...
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Veröffentlicht in: | Rapid communications in mass spectrometry 2014-10, Vol.28 (19), p.2075-2083 |
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creator | Bowman, David T. Slater, Greg F. Warren, Lesley A. McCarry, Brian E. |
description | RATIONALE
Naphthenic acids (NAs) accumulate in oil sands process‐affected water (OSPW) as a result of the water‐based extraction processes, and represent one of the toxic fractions in OSPW. They exist as a complex mixture and so the development of an analytical method to characterize and quantify individual acids has been an on‐going challenge. The multidimensional separation technique of two‐dimensional gas chromatography (GC × GC) has the potential to provide a fingerprint of the sources of NAs and can potentially resolve individual analytes for target analysis. However, the identity and toxicity of a large proportion of the acids present in tailing waters are still unknown.
METHODS
Comprehensive two‐dimensional gas chromatography/time‐of‐flight mass spectrometry (GC × GC/TOFMS) was used to characterize NAs in a pore water sample from a Syncrude composite tailings (CT) deposit in Fort McMurray, Alberta, Canada. The extractable organic acid fraction was derivatized with diazomethane and the structures of selected resolved esters were elucidated through interpretation of their electron ionization (EI) mass spectra and, if available, confirmed by comparison with the spectra of reference standards.
RESULTS
The high resolving power of the GC × GC/TOFMS technique allowed for the structural elucidation of numerous as yet unidentified acids in the CT pore water sample such as carboxylic acids containing a thiophene, indane, tetralin or cyclohexane moiety. Seventeen members of the previously reported class of adamantane‐type carboxylic acids in oil sands process water could also be identified in the sample.
CONCLUSIONS
This study underlines the complexity of naphthenic acid isomer distributions in composite tailings and provides a useful inventory of individual acids. Copyright © 2014 John Wiley & Sons, Ltd. |
doi_str_mv | 10.1002/rcm.6996 |
format | Article |
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Naphthenic acids (NAs) accumulate in oil sands process‐affected water (OSPW) as a result of the water‐based extraction processes, and represent one of the toxic fractions in OSPW. They exist as a complex mixture and so the development of an analytical method to characterize and quantify individual acids has been an on‐going challenge. The multidimensional separation technique of two‐dimensional gas chromatography (GC × GC) has the potential to provide a fingerprint of the sources of NAs and can potentially resolve individual analytes for target analysis. However, the identity and toxicity of a large proportion of the acids present in tailing waters are still unknown.
METHODS
Comprehensive two‐dimensional gas chromatography/time‐of‐flight mass spectrometry (GC × GC/TOFMS) was used to characterize NAs in a pore water sample from a Syncrude composite tailings (CT) deposit in Fort McMurray, Alberta, Canada. The extractable organic acid fraction was derivatized with diazomethane and the structures of selected resolved esters were elucidated through interpretation of their electron ionization (EI) mass spectra and, if available, confirmed by comparison with the spectra of reference standards.
RESULTS
The high resolving power of the GC × GC/TOFMS technique allowed for the structural elucidation of numerous as yet unidentified acids in the CT pore water sample such as carboxylic acids containing a thiophene, indane, tetralin or cyclohexane moiety. Seventeen members of the previously reported class of adamantane‐type carboxylic acids in oil sands process water could also be identified in the sample.
CONCLUSIONS
This study underlines the complexity of naphthenic acid isomer distributions in composite tailings and provides a useful inventory of individual acids. Copyright © 2014 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0951-4198</identifier><identifier>EISSN: 1097-0231</identifier><identifier>DOI: 10.1002/rcm.6996</identifier><identifier>PMID: 25156597</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>Alberta ; Carboxylic acids ; Mass spectrometry ; Naphthenic acids ; Oil sands ; Porosity ; Tailings</subject><ispartof>Rapid communications in mass spectrometry, 2014-10, Vol.28 (19), p.2075-2083</ispartof><rights>Copyright © 2014 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3876-452755ad6808e39c0085dabffec47d0a0e74f7a1e81984f5aa5135b80818188f3</citedby><orcidid>0000-0001-7418-7566</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Frcm.6996$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Frcm.6996$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25156597$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bowman, David T.</creatorcontrib><creatorcontrib>Slater, Greg F.</creatorcontrib><creatorcontrib>Warren, Lesley A.</creatorcontrib><creatorcontrib>McCarry, Brian E.</creatorcontrib><title>Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands</title><title>Rapid communications in mass spectrometry</title><addtitle>Rapid Commun. Mass Spectrom</addtitle><description>RATIONALE
Naphthenic acids (NAs) accumulate in oil sands process‐affected water (OSPW) as a result of the water‐based extraction processes, and represent one of the toxic fractions in OSPW. They exist as a complex mixture and so the development of an analytical method to characterize and quantify individual acids has been an on‐going challenge. The multidimensional separation technique of two‐dimensional gas chromatography (GC × GC) has the potential to provide a fingerprint of the sources of NAs and can potentially resolve individual analytes for target analysis. However, the identity and toxicity of a large proportion of the acids present in tailing waters are still unknown.
METHODS
Comprehensive two‐dimensional gas chromatography/time‐of‐flight mass spectrometry (GC × GC/TOFMS) was used to characterize NAs in a pore water sample from a Syncrude composite tailings (CT) deposit in Fort McMurray, Alberta, Canada. The extractable organic acid fraction was derivatized with diazomethane and the structures of selected resolved esters were elucidated through interpretation of their electron ionization (EI) mass spectra and, if available, confirmed by comparison with the spectra of reference standards.
RESULTS
The high resolving power of the GC × GC/TOFMS technique allowed for the structural elucidation of numerous as yet unidentified acids in the CT pore water sample such as carboxylic acids containing a thiophene, indane, tetralin or cyclohexane moiety. Seventeen members of the previously reported class of adamantane‐type carboxylic acids in oil sands process water could also be identified in the sample.
CONCLUSIONS
This study underlines the complexity of naphthenic acid isomer distributions in composite tailings and provides a useful inventory of individual acids. Copyright © 2014 John Wiley & Sons, Ltd.</description><subject>Alberta</subject><subject>Carboxylic acids</subject><subject>Mass spectrometry</subject><subject>Naphthenic acids</subject><subject>Oil sands</subject><subject>Porosity</subject><subject>Tailings</subject><issn>0951-4198</issn><issn>1097-0231</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpdkcFu1DAQhi0EoktB4gmQJS4cSLGTOE6O1ardViogIRBHa-JMWBcnDrZDN0_Ea-KwpUhoDjOa-fRrZn5CXnJ2xhnL33k9nFVNUz0iG84ambG84I_JhjWCZyVv6hPyLIRbxjgXOXtKTnLBRSUauSG_rjsco-mNhmjcSF1PzdiZn6abwdK4N27a44jZ27UNf4qI0YM1Yyr1oq3b4-E4gLGj0MEAY1wbcZmQavCtOyzWaAradCHJUO2GyQUTkUYwSehboJPzSO8goqe9dwM9ty36CNQZS0PSDc_Jkx5swBf3-ZR8ubz4vL3Kbj7urrfnN5kualllpcilENBVNauxaDRjteig7XvUpewYMJRlL4Fjnb5S9gJA8EK0ieYp6r44JW-OupN3P2YMUQ0maLQ2XeTmoHiVM1ZKlpcJff0feutmP6btFBdCNLmsRZOoV_fU3A7YqcmbAfyi_lqQgOwI3BmLy8OcM7Vaq5K1arVWfdq-X_M_3oSIhwce_HdVyUIK9fXDTuWS7_jVpVC8-A3vBKXQ</recordid><startdate>20141015</startdate><enddate>20141015</enddate><creator>Bowman, David T.</creator><creator>Slater, Greg F.</creator><creator>Warren, Lesley A.</creator><creator>McCarry, Brian E.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>JQ2</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-7418-7566</orcidid></search><sort><creationdate>20141015</creationdate><title>Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands</title><author>Bowman, David T. ; Slater, Greg F. ; Warren, Lesley A. ; McCarry, Brian E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3876-452755ad6808e39c0085dabffec47d0a0e74f7a1e81984f5aa5135b80818188f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alberta</topic><topic>Carboxylic acids</topic><topic>Mass spectrometry</topic><topic>Naphthenic acids</topic><topic>Oil sands</topic><topic>Porosity</topic><topic>Tailings</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bowman, David T.</creatorcontrib><creatorcontrib>Slater, Greg F.</creatorcontrib><creatorcontrib>Warren, Lesley A.</creatorcontrib><creatorcontrib>McCarry, Brian E.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Rapid communications in mass spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bowman, David T.</au><au>Slater, Greg F.</au><au>Warren, Lesley A.</au><au>McCarry, Brian E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands</atitle><jtitle>Rapid communications in mass spectrometry</jtitle><addtitle>Rapid Commun. Mass Spectrom</addtitle><date>2014-10-15</date><risdate>2014</risdate><volume>28</volume><issue>19</issue><spage>2075</spage><epage>2083</epage><pages>2075-2083</pages><issn>0951-4198</issn><eissn>1097-0231</eissn><abstract>RATIONALE
Naphthenic acids (NAs) accumulate in oil sands process‐affected water (OSPW) as a result of the water‐based extraction processes, and represent one of the toxic fractions in OSPW. They exist as a complex mixture and so the development of an analytical method to characterize and quantify individual acids has been an on‐going challenge. The multidimensional separation technique of two‐dimensional gas chromatography (GC × GC) has the potential to provide a fingerprint of the sources of NAs and can potentially resolve individual analytes for target analysis. However, the identity and toxicity of a large proportion of the acids present in tailing waters are still unknown.
METHODS
Comprehensive two‐dimensional gas chromatography/time‐of‐flight mass spectrometry (GC × GC/TOFMS) was used to characterize NAs in a pore water sample from a Syncrude composite tailings (CT) deposit in Fort McMurray, Alberta, Canada. The extractable organic acid fraction was derivatized with diazomethane and the structures of selected resolved esters were elucidated through interpretation of their electron ionization (EI) mass spectra and, if available, confirmed by comparison with the spectra of reference standards.
RESULTS
The high resolving power of the GC × GC/TOFMS technique allowed for the structural elucidation of numerous as yet unidentified acids in the CT pore water sample such as carboxylic acids containing a thiophene, indane, tetralin or cyclohexane moiety. Seventeen members of the previously reported class of adamantane‐type carboxylic acids in oil sands process water could also be identified in the sample.
CONCLUSIONS
This study underlines the complexity of naphthenic acid isomer distributions in composite tailings and provides a useful inventory of individual acids. Copyright © 2014 John Wiley & Sons, Ltd.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>25156597</pmid><doi>10.1002/rcm.6996</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-7418-7566</orcidid></addata></record> |
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subjects | Alberta Carboxylic acids Mass spectrometry Naphthenic acids Oil sands Porosity Tailings |
title | Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands |
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