Biocatalytic Detoxification of 2-Chloroethyl Ethyl Sulfide

Kilbane, John J.; Jackowski, Kathy

doi:10.1002/(sici)1097-4660(199604)65:4<370::aid-jctb445>3.0.co;2-2

Cited by 22 publications

(10 citation statements)

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“…Van Hamme et al (45) have shown that a variety of white-rot fungi oxidize dibenzyl sulfide to dibenzyl sulfoxide and dibenzyl sulfone prior to further degradation. However, other examples of the microbial degradation of compounds containing this type of bond (e.g., 2-chloroethyl sulfide and thiodiglycol) give no evidence for direct sulfur oxidation followed by COS bond cleavage without degradation of the alkyl or aromatic moieties (20,29,36,40). For example, metabolism by Nocardioides simplex of 1-(phytanylsulfanyl)-octadecane (used as a model compound for sulfide bridges in high-molecular-weight fractions of sulfur-rich petroleum) has been described previously (18); although the sulfur was oxidized, no COS bond cleavage was observed.…”

mentioning

confidence: 99%

Use of a Novel Fluorinated Organosulfur Compound To Isolate Bacteria Capable of Carbon-Sulfur Bond Cleavage

Hamme

Fedorak

Foght

et al. 2004

Appl Environ Microbiol

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The vacuum residue fraction of heavy crudes contributes to the viscosity of these oils. Specific microbial cleavage of COS bonds in alkylsulfide bridges that form linkages in this fraction may result in dramatic viscosity reduction. To date, no bacterial strains have been shown conclusively to cleave COS bonds within alkyl chains. Screening for microbes that can perform this activity was greatly facilitated by the use of a newly synthesized compound, bis-(3-pentafluorophenylpropyl)-sulfide (PFPS), as a novel sulfur source. The terminal pentafluorinated aromatic rings of PFPS preclude growth of aromatic ring-degrading bacteria but allow for selective enrichment of strains capable of cleaving COS bonds. A unique bacterial strain, Rhodococcus sp. strain JVH1, that used PFPS as a sole sulfur source was isolated from an oil-contaminated environment. Gas chromatography-mass spectrometry analysis revealed that JVH1 oxidized PFPS to a sulfoxide and then a sulfone prior to cleaving the COS bond to form an alcohol and, presumably, a sulfinate from which sulfur could be extracted for growth. Four known dibenzothiophene-desulfurizing strains, including Rhodococcus sp. strain IGTS8, were all unable to cleave the COS bond in PFPS but could oxidize PFPS to the sulfone via the sulfoxide. Conversely, JVH1 was unable to oxidize dibenzothiophene but was able to use a variety of alkyl sulfides, in addition to PFPS, as sole sulfur sources. Overall, PFPS is an excellent tool for isolating bacteria capable of cleaving subterminal COS bonds within alkyl chains. The type of desulfurization displayed by JVH1 differs significantly from previously described reaction results.Microbial methods of removing sulfur from organosulfur compounds are of interest to the petroleum industry for reducing sulfur emissions and, more recently, for reducing heavy oil viscosity. As conventional crude oils are consumed throughout the world, heavier oils are being exploited which, due to their high viscosity, cannot be transported from remote field sites to refineries without adding diluents. The vacuum residue fraction of crude oils (boiling point Ն 524°C [975°F]) contributes to viscosity, and recent models indicate that alkyl sulfides compose important bridges in the network of high-molecularweight molecules in this fraction (34). Up to 40% of the sulfur in these fractions is in the form of alkyl sulfides; if these alkyl COS bonds can be selectively cleaved using a biological catalyst, reductions in molecular size and viscosity could occur.The first requirement for developing a biological process for heavy oil viscosity reduction is obtaining a microorganism capable of alkyl COS bond cleavage without reducing the carbon value of the substrate. Precedence for this type of reaction with aromatic heterocycles can be found in the well-characterized 4S pathway that selectively removes sulfur from dibenzothiophene (DBT) (35). The dsz or sox operon (genes responsible for DBT desulfurization) (7,38) in Rhodococcus sp. strain IGTS8 has been observed in a variety of ...

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confidence: 99%

Use of a Novel Fluorinated Organosulfur Compound To Isolate Bacteria Capable of Carbon-Sulfur Bond Cleavage

Hamme

Fedorak

Foght

et al. 2004

Appl Environ Microbiol

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“…The results with acetonitrile, a toxic compound with poor biokinetic properties, further suggest that drip-feed biotreatment would offer a safe alternative for the treatment of other highly toxic, but biodegradable substances, such as sarin, VX, and mustard (Kilbane and Jackowski 1996, Lee et al 1996, Shem et al 1995. Challenges facing the safe disposal of chemical warfare materiel (CWM) is similar to the challenges facing the safe disposal of mixed wastes.…”

Section: Drip-feed Bioreactor Operationmentioning

confidence: 99%

“…Biological treatment of mustard and mustard hydrolysis products have been demonstrated (Kilbane and Jackowski 1996, Lee et al 1996, NRC 2000, NRC 2002, Shem et al 1995, but projects examining the biological treatment of nerve agents have failed due to poor bioreactor design (NRC 2000). Novel reactor configurations, such as the drip-feed bioreactor, could offer practical alternatives to the disposal of difficult to handle waste streams.…”

Section: Drip-feed Bioreactor Operationmentioning

confidence: 99%

Biological treatment of concentrated hazardous, toxic, andradionuclide mixed wastes without dilution

Stringfellow¹,

Komada²,

Chang³

2004

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Approximately 10% of all radioactive wastes produced in the U. S. are mixed with hazardous or toxic chemicals and therefore can not be placed in secure land disposal facilities.Mixed wastes containing hazardous organic chemicals are often incinerated, but volatile radioactive elements are released directly into the biosphere. Some mixed wastes do not currently have any identified disposal option and are stored locally awaiting new developments.Biological treatment has been proposed as a potentially safer alternative to incineration for the treatment of hazardous organic mixed wastes, since biological treatment would not release volatile radioisotopes and the residual low-level radioactive waste would no longer be restricted from land disposal. Prior studies have shown that toxicity associated with acetonitrile is a significant limiting factor for the application of biotreatment to mixed wastes and excessive dilution was required to avoid inhibition of biological treatment. In this study, we demonstrate that a novel reactor configuration, where the concentrated toxic waste is drip-fed into a complete-mix bioreactor containing a pre-concentrated active microbial population, can be used to treat a surrogate acetonitrile mixed waste stream without excessive dilution. Using a drip-feed bioreactor, we were able to treat a 90,000 mg/L acetonitrile solution to less than 0.1 mg/L final concentration using a dilution factor of only 3.4. It was determined that the acetonitrile degradation reaction was inhibited at a pH above 7.2 and that the reactor could be modeled using conventional kinetic and mass balance approaches. Using a drip-feed reactor configuration addresses a major limiting factor (toxic inhibition) for the biological treatment of toxic, hazardous, or radioactive mixed wastes and suggests that drip-feed bioreactors could be used to treat other concentrated toxic waste streams, such as chemical warfare materiel.

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“…There are comparatively few reports of the degradation of aliphatic sulfides, particularly of carbon-sulfur bond cleavage in high molecular weight representatives of this class of compound. Small compounds, including methyl, ethyl, propyl and butyl sulfides Taylor 1993a, 1993b), 2-chloroethyl ethyl sulfide (Kilbane and Jackowski 1996) and thiodiglycol (Lee et al 2001), are cleaved at the sulfur atom. The latter two compounds were used to investigate the potential for biological treatment of the chemical warfare agent sulfur mustard (2,2¢-dichlorodiethyl sulfide).…”

Section: Introductionmentioning

confidence: 99%

Bacterial biodegradation of aliphatic sulfides under aerobic carbon- or sulfur-limited growth conditions

Kirkwood¹,

Ebert

Foght

et al. 2005

J Appl Microbiol

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Aims: To isolate bacteria capable of cleaving aliphatic carbon-sulfur bonds as potential biological upgrading catalysts for the reduction of molecular weight and viscosity in heavy crude oil. Methods and Results: Thirty-one bacterial strains isolated from enrichment cultures were able to biotransform model compounds representing the aliphatic sulfide bridges found in asphaltenes. Using gas chromatography and mass spectrometry, three types of attack were identified: alkyl chain degradation, allowing use as a carbon source; nonspecific sulfur oxidation; and sulfur-specific oxidation and carbon-sulfur bond cleavage, allowing use as a sulfur source. Di-n-octyl sulfide degradation produced octylthio-and octylsulfonyl-alkanoic acids, consistent with terminal oxidation followed by b-oxidation reactions. Utilization of dibenzyl sulfide or 1,4-dithiane as a sulfur source was regulated by sulfate, indicating a sulfur-specific activity rather than nonspecific oxidation. Finally, several isolates were also able to use dibenzothiophene as a sulfur source, and this was the preferred organic sulfur substrate for one isolate. Conclusions: The use of commercially available alkyl sulfides in enrichment cultures gave isolates that followed a range of metabolic pathways, not just sulfur-specific attack. Significance and Impact of the Study: These results give new insight into biodegradation of organosulfur compounds from petroleum and for biotreatment of such compounds in chemical munitions.

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Biocatalytic Detoxification of 2-Chloroethyl Ethyl Sulfide

Cited by 22 publications

References 0 publications

Use of a Novel Fluorinated Organosulfur Compound To Isolate Bacteria Capable of Carbon-Sulfur Bond Cleavage

Use of a Novel Fluorinated Organosulfur Compound To Isolate Bacteria Capable of Carbon-Sulfur Bond Cleavage

Biological treatment of concentrated hazardous, toxic, andradionuclide mixed wastes without dilution

Bacterial biodegradation of aliphatic sulfides under aerobic carbon- or sulfur-limited growth conditions

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