Identification of ester metabolites from petroleum hydrocarbon biodegradation in groundwater using GC×GC‐TOFMS

O’Reilly, Kirk T.; Mohler, Rachel E.; Zemo, Dawn A.; Ahn, Seung Ho; Tiwary, Asheesh K.; Magaw, Renae; Devine, Catalina Espino; Synowiec, Karen A.

doi:10.1002/etc.3022

Cited by 24 publications

(23 citation statements)

References 15 publications

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“…Mohler et al () were able to match 750 compounds to known standards but this represented only 23% of the total ion chromatogram. Some of these compounds have been identified as alcohols, organic acids (Cozzarelli et al ), aldehydes, ketones, and esters (Zemo et al ; O'Reilly et al ), but Mao et al () identified complex structures with multiple oxygen molecules that are not readily placed into these categories. The majority of the compounds identified in these studies have carbon numbers less than 18 carbons whereas at Bemidji, the partial degradation products recovered have carbon numbers per average molecule of 18 and higher (Thorn and Aiken ), so metabolites in crude oil plumes may differ from those in gasoline plumes.…”

Section: Discussionmentioning

confidence: 99%

Crude Oil Metabolites in Groundwater at Two Spill Sites

et al. 2016

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Two groundwater plumes in north central Minnesota with residual crude oil sources have 20 to 50 mg/L of nonvolatile dissolved organic carbon (NVDOC). These values are over 10 times higher than benzene and two to three times higher than Diesel Range Organics in the same wells. On the basis of previous work, most of the NVDOC consists of partial transformation products from the crude oil. Monitoring data from 1988 to 2015 at one of the sites located near Bemidji, MN show that the plume of metabolites is expanding toward a lakeshore located 335 m from the source zone. Other mass balance studies of the site have demonstrated that the plume expansion is driven by the combined effect of continued presence of the residual crude oil source and depletion of the electron accepting capacity of solid phase iron oxide and hydroxides on the aquifer sediments. These plumes of metabolites are not covered by regulatory monitoring and reporting requirements in Minnesota and other states. Yet, a review of toxicology studies indicates that polar metabolites of crude oil may pose a risk to aquatic and mammalian species. Together the results suggest that at sites where residual sources are present, monitoring of NVDOC may be warranted to evaluate the fates of plumes of hydrocarbon transformation products.

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Section: Discussionmentioning

confidence: 99%

Crude Oil Metabolites in Groundwater at Two Spill Sites

et al. 2016

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“…Mohler et al () listed 768 TICs that occurred in source area and downgradient samples from five fuel terminals ( n = 22), but information was not presented as to how often the specific individual compounds had been detected or how the mixture of individual compounds differed between samples. O'Reilly et al () listed individual esters tentatively identified in 61 samples. Results are now available from 113 groundwater samples collected from 51 monitoring wells at 17 fuel terminals and 5 service station sites.…”

Section: Introductionmentioning

confidence: 99%

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

O’Reilly

Mohler

Zemo³

et al. 2019

Groundwater Monitoring Rem

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This research continues a 7‐year study of oxygen‐containing organic compounds present in groundwater at gasoline and diesel fuel release sites that are quantified as diesel‐range “total petroleum hydrocarbons” when measured by methods utilizing solvent extraction and gas chromatography. Two‐dimensional gas chromatography with time‐of‐flight mass spectrometry was used to tentatively identify 1162 compounds (TICs) in 113 groundwater samples from 22 sites. Samples were collected from wells either upgradient of the release, within the source zone, or downgradient of the source but still within the plume of dissolved organics associated with release. The names and formulas of all TICs found in samples from each well type are presented and the results from upgradient and downgradient locations are compared in detail. About 60% of the most frequently detected TICs in downgradient wells were also detected in upgradient wells. A majority of these were saturated straight chain alkyl acids, commonly called fatty acids, or fatty acid esters. Of TICs frequently detected in downgradient wells but not upgradient wells, over half were branched alkyl alcohols. Hierarchical cluster analysis results suggest about 80% of the chemical composition of downgradient samples is more similar to upgradient samples than to source area samples. This similarity is due to the presence of the same types of fatty acids and esters. Principal component analysis indicates a continuum of biodegradation between the source area and downgradient samples with the latter becoming more consistent with upgradient samples. Results suggest some TICs may not be petroleum degradation intermediates but compounds synthesized by microorganisms through secondary production and carbon cycling.

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“…The presence of a nonaqueous‐phase liquid (NAPL) has been shown to act as an additional partitioning phase for PAHs and PCBs , with sediment–water distribution coefficients ( K d ) gradually increasing at oil concentrations above those resulting in a NAPL . The bioavailability of petroleum hydrocarbon constituents via the soil pore‐water will be a function of their partitioning behavior between water, the soil organic carbon, and the NAPL (see also http://www.api.org/~/media/Files/EHS/Clean_Water/Bulletins/14_Bull.pdf).…”

Section: Discussionmentioning

confidence: 99%

“…The degree of partitioning to a NAPL is dependent on the amount of NAPL present . Thus, the bioavailability of petroleum hydrocarbons, and their toxicity on a soil concentration basis, will depend on the size of a NAPL present.…”

Section: Discussionmentioning

confidence: 99%

TOXICITY AND TOXICOKINETICS OF BINARY COMBINATIONS OF PETROLEUM HYDROCARBON DISTILLATES WITH THE EARTHWORM EISENIA ANDREI

Cermak

Stephenson

Birkholz³

et al. 2013

Enviro Toxic and Chemistry

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Petroleum hydrocarbons (PHCs) act via narcosis and are expected to have additive toxicity. However, previous work has demonstrated less-than-additive toxicity with PHC distillates and earthworms. A study was initiated to investigate this through toxicity and toxicokinetic studies with the earthworm Eisenia andrei. Three petroleum distillate fractions, F2 (>C10-C16), F3a (>C16-C23), and F3b (>C23-C34), were used in two binary combinations, F2F3a and F3aF3b. In the toxicity study, clean soil was spiked with equitoxic combinations of the two distillates ranging from 0.5 to 2.5 toxic units. In the toxicokinetic study, a binary combination consisting of one concentration of each distillate was used. On a soil concentration basis, the toxicity of the binary combinations of distillates was less than additive. Accumulation of the individual distillates, however, was generally reduced when a second distillate was present, resulting in lower body burden. This is thought to be due to the presence of a nonaqueous-phase liquid at the soil concentrations used. On a tissue concentration basis, toxicity was closer to additive. The results demonstrate that tissue concentrations are the preferred metric for toxicity for earthworms. They also demonstrate that the Canada-wide soil standards based on individual distillates are likely protective.

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Identification of ester metabolites from petroleum hydrocarbon biodegradation in groundwater using GC×GC‐TOFMS

Cited by 24 publications

References 15 publications

Crude Oil Metabolites in Groundwater at Two Spill Sites

Crude Oil Metabolites in Groundwater at Two Spill Sites

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

TOXICITY AND TOXICOKINETICS OF BINARY COMBINATIONS OF PETROLEUM HYDROCARBON DISTILLATES WITH THE EARTHWORM EISENIA ANDREI

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