Ethylene glycol ethers: An environmental risk assessment

Staples, Charles A.; Boatman, Rodney J.; Cano, Manuel L.

doi:10.1016/s0045-6535(97)10056-x

Cited by 36 publications

(20 citation statements)

References 13 publications

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“…The DCM/water partitioning coefficients (log P DCM/water ) of the autoxidation byproducts were found to be À0.004, 0.56, and 0.48 for DEGBE, DEGBE-acetate, and butyl acetate, respectively. Values reported in the literature for the octanol/water partitioning coefficients (log P oct/water ) for these compounds are found to agree reasonably with values reported in the present study for log P DCM/water [12,13]. This means that 51, 77, and 75% of the total DEGBE, DEGBEacetate, and butyl acetate, respectively, partitioned to the DCM phase during solvent extraction.…”

Section: Results and Analysissupporting

confidence: 91%

“…Values reported in the literature for the octanol/water partitioning coefficients (log P oct/water ) for these compounds are found to agree reasonably with values reported in the present study for log P DCM/water [12,13]. The partitioning of these compounds between the DCM solvent phase and the aqueous phase was estimated by standard spikes of the pure compounds in deionized water followed by liquidliquid extraction with DCM.…”

Section: Results and Analysissupporting

confidence: 90%

“…Formation of similar products was also documented by other researchers [26,27]. However, those diethylene glycols as well as butyl acetate are not expected to pose a serious long-term threat in aquatic systems, because they have been shown to be readily biodegradable [12,28]. The formation of the diethylene glycols in the WAF of commercial soybean biodiesel, but not in the laboratory-transesterified one or in the pure FAMEs, suggests the presence of a putative catalyst in the former.…”

Section: Discussionsupporting

confidence: 75%

“…The formation of the diethylene glycols in the WAF of commercial soybean biodiesel, but not in the laboratory-transesterified one or in the pure FAMEs, suggests the presence of a putative catalyst in the former. However, those diethylene glycols as well as butyl acetate are not expected to pose a serious long-term threat in aquatic systems, because they have been shown to be readily biodegradable [12,28]. Whatever the cause of excessive autoxidation may be, it does not appear to be influenced by the source of the biodiesel feedstock itself because the FAME molecules were determined to be nontoxic, and only the autoxidation byproducts of C18:1-ME and C18:3 were.…”

Section: Discussionmentioning

confidence: 99%

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Microtox aquatic toxicity of petrodiesel and biodiesel blends: The role of biodiesel's autoxidation products

Yassine

Suidan

et al. 2012

Enviro Toxic and Chemistry

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The acute Microtox toxicity of the water accommodated fraction (WAF) of six commercial soybean biodiesel/petrodiesel blends was investigated at different oil loads. We analyzed five fatty acid methyl esters (FAMEs), C10-C24 n-alkanes, four aromatics, methanol, and total organic carbon (TOC) content. At high oil loads, the WAFs' toxicity was significantly higher for blends containing biodiesel. At the lowest load, the WAFs' toxicity decreased almost linearly with decreasing biodiesel in the blend. At intermediate loads, the WAFs of all the blends appeared to have a similar toxicity. Analysis of WAFs confirmed the presence of autoxidation byproducts of FAMEs at high oil loads. Pure unsaturated FAMEs and n-alkanes were nontoxic when present in water at their reported solubility limits. However, 24-h equilibrated WAFs of pure FAMEs were highly toxic for C18:1 and C18:3, but not for C18:2. The authors concluded that at high oil loads, the acute toxicity of the WAFs was caused by FAMEs' autoxidation byproducts, whereas at low oil loads, the toxicity appeared to be caused primarily by the aromatic compounds present in petrodiesel. The addition of a synthetic antioxidant in biodiesel did not appear to affect the concentration of autoxidation byproducts in the WAF but resulted in a slight decrease in its toxicity. The major autoxidation byproducts identified in the WAF of commercial biodiesel were present neither in the WAFs of pure unsaturated FAMEs nor in the WAF of a different soybean biodiesel that was transesterified in our laboratory, which was nontoxic. We concluded that the process of transesterification of biodiesel might be a more critical factor in determining the aquatic toxicity of the fuel than the source of feedstock itself.

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Section: Results and Analysissupporting

confidence: 91%

Section: Results and Analysissupporting

confidence: 90%

Section: Discussionsupporting

confidence: 75%

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Microtox aquatic toxicity of petrodiesel and biodiesel blends: The role of biodiesel's autoxidation products

Yassine

Suidan

et al. 2012

Enviro Toxic and Chemistry

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“…Worldwide production was more than 1 million metric tons in 1999 (34). Many glycol ethers are biodegradable, and numerous toxicology studies have been published (35)(36)(37)(38)(39).…”

Section: Introductionmentioning

confidence: 99%

Use of Glycol Ethers for Selective Release of Periplasmic Proteins from Gram-Negative Bacteria

et al. 2007

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Genetic modification of Gram-negative bacteria to express a desired protein within the cell's periplasmic space, located between the inner cytoplasmic membrane and the outer cell wall, can offer an attractive strategy for commercial production of therapeutic proteins and industrial enzymes. In certain applications, the product expression rate is high, and the ability to isolate the product from the cell mass is greatly enhanced because of the product's compartmentalized location within the cell. Protein release methods that increase the permeability of the outer cell wall for primary recovery, but avoid rupturing the inner cell membrane, reduce contamination of the recovered product with other host cell components and simplify final purification. This article reports representative data for a new release method employing glycol ether solvents. The example involves the use of 2-butoxyethanol (commonly called ethylene glycol n-butyl ether or EB) for selective release of a proprietary biopharmaceutical protein produced in the periplasmic space of Pseudomonas fluorescens. In this example, glycol ether treatment yielded approximately 65% primary recovery with approximately 80% purity on a protein-only basis. Compared with other methods including heat treatment, osmotic shock, and the use of surfactants, the glycol ether treatment yielded significantly reduced concentrations of other host cell proteins, lipopolysaccharide endotoxin, and DNA in the recovered protein solution. The use of glycol ethers also allowed exploitation of temperature-change-induced phase splitting behavior to concentrate the desired product. Heating the aqueous EB extract solution to 55 degrees C formed two liquid phases: a glycol ether-rich phase and an aqueous product phase containing the great majority of the product protein. This phase-splitting step yielded an approximate 10-fold reduction in the volume of the initial product solution and a corresponding increase in the product's concentration.

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Ethers of Ethylene Glycol and Derivatives

Kelsey

2023

Patty's Toxicology

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E series Glycol ethers are alkyl ethers of ethylene glycol along with their acetate esters. They are commonly used in paints and cleaners and typically have a higher boiling point in conjunction with the favorable solvent properties of lower‐molecular weight ethers, esters, and alcohols. They are colorless liquids that have mild earthy or fruity odors. The ethers are miscible with water and/or with numerous organic solvents making them useful as solvents in oil‐water compositions. Their relatively slow rate of evaporation also makes them useful as solvents and coalescing agents in paints and inks. The surface tension and solvent properties of the ethers make them useful in cleaners. Other uses of the ethers include process solvents and deicers. The ethers of the higher glycols are used as hydraulic fluids. Occupational exposure to glycol ethers occurs dermally and by inhalation. Most glycol ethers have low acute, single‐dose toxicity to humans. The most notable and well‐known effect relevant to humans is toxicity to male fertility and developmental toxicity produced by those glycol ethers that can metabolize to produce significant amounts of methoxyacetic acid such as methoxy ethanol and the methyl glymes.

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Ethylene glycol ethers: An environmental risk assessment

Cited by 36 publications

References 13 publications

Microtox aquatic toxicity of petrodiesel and biodiesel blends: The role of biodiesel's autoxidation products

Microtox aquatic toxicity of petrodiesel and biodiesel blends: The role of biodiesel's autoxidation products

Use of Glycol Ethers for Selective Release of Periplasmic Proteins from Gram-Negative Bacteria

Ethers of Ethylene Glycol and Derivatives

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