Structure-dependent degradation of polar compounds in weathered oils observed by atmospheric pressure photo-ionization hydrogen/deuterium exchange ultrahigh resolution mass spectrometry.
The resin fractions of fresh mixtures of three oils spilled during the M/V Hebei Spirit oil spill, as well as weathered oils collected at weathering stages II and IV from the oil spill site were analyzed and compared by atmospheric pressure photo-ionization hydrogen/deuterium exchange mass spectrometry (HDX MS). The significantly decreased abundance of N(+) and [N-H+D](+) ions suggested that secondary and tertiary amine-containing compounds were preferentially degraded during the early stage of weathering. [N+H](+) and [N+D](+) ions previously attributed to pyridine-type compounds degraded more slowly than secondary and tertiary amine-containing compounds. The preferential degradation of nitrogen-containing compounds was confirmed by photo-degradation experiments using 15 standard compounds. In addition, significant increases of [S1O1+H](+) and [S1O1+D](+) ions with higher DBE values were observed from fresh oil mixtures as compared to stages II and IV samples, and that could be linked with the decrease of higher DBE compounds of the S1 class. This study presented convincing arguments and evidence demonstrating that secondary and tertiary amines were more vulnerable to photo-degradation than compounds containing pyridine, and hence, preferential degradation depending on chemical structures must be considered in the production of hazardous or toxic components.
Kyungpook National University, Department of Chemistry, Daegu 702-701, Republic of Korea.
Ananna
A
Islam
Kyungpook National University, Department of Chemistry, Daegu 702-701, Republic of Korea.
Donghwi
D
Kim
Oil and POPs Research Group, Korea Institute of Ocean Science and Technology, KIOST, Geoje 656-834, Republic of Korea.
Un Hyuk
UH
Yim
Oil and POPs Research Group, Korea Institute of Ocean Science and Technology, KIOST, Geoje 656-834, Republic of Korea.
Won Joon
WJ
Shim
Kyungpook National University, Department of Chemistry, Daegu 702-701, Republic of Korea; Green Nano Center, Department of Chemistry, Daegu 702-701, Republic of Korea. Electronic address: sunghwank@knu.ac.kr.
Sunghwan
S
Kim
D001274:Atmospheric Pressure; D041961:Deuterium Exchange Measurement / Q000379:methods; D004784:Environmental Monitoring / Q000295:instrumentation / Q000379:methods*; D052918:Environmental Restoration and Remediation; D013058:Mass Spectrometry / Q000379:methods; D010578:Petroleum / Q000032:analysis*; D059392:Petroleum Pollution / Q000032:analysis*; D056910:Republic of Korea; D014874:Water Pollutants, Chemical / Q000032:analysis* / Q000737:chemistry; D014887:Weather
D010578:Petroleum; D014874:Water Pollutants, Chemical
Atmospheric pressure photo-ionization hydrogen/deuterium exchange mass spectrometry (HDX MS); Double bond equivalent; Oil spill; Petroleum; Photo-degradation; Ultrahigh resolution mass spectrometry