ethylene dichlorides

Summary

Summary: Toxic, chlorinated, saturated hydrocarbons. Include both the 1,1- and 1,2-dichloro isomers. The latter is considerably more toxic. It has a sweet taste, ethereal odor and has been used as a fumigant and intoxicant among sniffers. Has many household and industrial uses.

Top Publications

  1. Nagano K, Umeda Y, Senoh H, Gotoh K, Arito H, Yamamoto S, et al. Carcinogenicity and chronic toxicity in rats and mice exposed by inhalation to 1,2-dichloroethane for two years. J Occup Health. 2006;48:424-36 pubmed
    ..The present findings suggest that those carcinogenic responses be primarily considered for standard setting of occupational and environmental exposure to DCE. ..
  2. Grostern A, Edwards E. Characterization of a Dehalobacter coculture that dechlorinates 1,2-dichloroethane to ethene and identification of the putative reductive dehalogenase gene. Appl Environ Microbiol. 2009;75:2684-93 pubmed publisher
    ..As a collective, the genus Dehalobacter has been show to dechlorinate many diverse compounds, but individual species seem to each have a narrow substrate range...
  3. Grostern A, Edwards E. Growth of Dehalobacter and Dehalococcoides spp. during degradation of chlorinated ethanes. Appl Environ Microbiol. 2006;72:428-36 pubmed
    ..This demonstrated that in mixed cultures containing multiple dechlorinating microorganisms, these organisms can have either competitive or complementary dechlorination activities, depending on the chloro-organic substrate...
  4. Marzorati M, de Ferra F, Van Raemdonck H, Borin S, Allifranchini E, Carpani G, et al. A novel reductive dehalogenase, identified in a contaminated groundwater enrichment culture and in Desulfitobacterium dichloroeliminans strain DCA1, is linked to dehalogenation of 1,2-dichloroethane. Appl Environ Microbiol. 2007;73:2990-9 pubmed
    ..In conclusion, these data suggest that the newly described RDs are specifically adapted to 1,2-DCA dechlorination...
  5. De Wildeman S, Diekert G, Van Langenhove H, Verstraete W. Stereoselective microbial dehalorespiration with vicinal dichlorinated alkanes. Appl Environ Microbiol. 2003;69:5643-7 pubmed
    ..This unique dehalorespiratory biochemistry has shown promising application possibilities for bioremediation purposes and fine-chemical synthesis...
  6. Maes A, Van Raemdonck H, Smith K, Ossieur W, Lebbe L, Verstraete W. Transport and activity of Desulfitobacterium dichloroeliminans strain DCA1 during bioaugmentation of 1,2-DCA-contaminated groundwater. Environ Sci Technol. 2006;40:5544-52 pubmed
    ..This study showed that strain DCA1 can be successfully applied for the removal of 1,2-DCA under field conditions and that its limited retardation offers perspectives for large-scale cleanup processes of industrial sites...
  7. Baur X, Poschadel B, Budnik L. High frequency of fumigants and other toxic gases in imported freight containers--an underestimated occupational and community health risk. Occup Environ Med. 2010;67:207-12 pubmed publisher
    ..Our findings indicate a health risk for dockworkers, container unloaders and even end-consumers, especially as many of the cancerogenic or toxic gases elude subjective detection. ..
  8. Silberstein M, Damborsky J, Vajda S. Exploring the binding sites of the haloalkane dehalogenase DhlA from Xanthobacter autotrophicus GJ10. Biochemistry. 2007;46:9239-49 pubmed
  9. Qu G, Sun M, Li S, Sun C, Liu T, Xu S, et al. Phase-transition induced changes in the electron-phonon coupling of all-trans-?-carotene. Spectrochim Acta A Mol Biomol Spectrosc. 2013;104:92-6 pubmed publisher
    ..The changes in the combination and harmonic modes are interpreted using the aforementioned model as well as the theory of electron-phonon interaction. ..

More Information

Publications62

  1. Lai Q, Huang F, Li W, Huang W. [MRI image analysis of 1,2-dichloroethane chronic toxic encephalopath]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2011;29:62-4 pubmed
    ..Combined with a history of exposure, the show of varying degrees of abnormal signal of white matter in 1,2-dichloroethane Chronic Toxic Encephalopathy cases are characteristic. ..
  2. Qi Y, Shi L, Gao L, Wang G, Li G, Lv X, et al. [Influence of 1, 2-dichloroethane on open field behavior and levels of neurotransmitters in brain of mice]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2011;29:413-6 pubmed
  3. Pant D, Girault H. Time-resolved total internal reflection fluorescence spectroscopy. Part I. Photophysics of Coumarin 343 at liquid/liquid interface. Phys Chem Chem Phys. 2005;7:3457-63 pubmed
    ..Aggregation is significant in the interfacial layer. The decrease in monomer lifetime at the interface compared to that in the bulk solution is interpreted in terms of excitation energy migration between the dye molecules. ..
  4. Arjoon A, Olaniran A, Pillay B. Enhanced 1,2-dichloroethane degradation in heavy metal co-contaminated wastewater undergoing biostimulation and bioaugmentation. Chemosphere. 2013;93:1826-34 pubmed publisher
    ..Results obtained in this study have significant implications for developing innovative bioremediation strategies for treating water co-contaminated with chlorinated organics and heavy metals. ..
  5. Sweeney L, Saghir S, Gargas M. Physiologically based pharmacokinetic model development and simulations for ethylene dichloride (1,2-dichloroethane) in rats. Regul Toxicol Pharmacol. 2008;51:311-23 pubmed publisher
  6. Segneanu A, Grozescu I, Cziple F, Berki D, Damian D, Niculite C, et al. Helleborus purpurascens-Amino Acid and Peptide Analysis Linked to the Chemical and Antiproliferative Properties of the Extracted Compounds. Molecules. 2015;20:22170-87 pubmed publisher
    ..Moreover, the two biologically tested fractions exerted a major antiproliferative effect, thereby suggesting potential anticancer therapeutic activity. ..
  7. Gulaboski R, Pereira C, Cordeiro M, Bogeski I, Ferreira E, Ribeiro D, et al. Electrochemical study of ion transfer of acetylcholine across the interface of water and a lipid-modified 1,2-dichloroethane. J Phys Chem B. 2005;109:12549-59 pubmed
    ..Additional characterization of those interactions has been made by using the surface tension measurements. ..
  8. Liu J, Fang S, Ding M, Chen Z, Zhou J, Sun F, et al. Toxic encephalopathy caused by occupational exposure to 1, 2-Dichloroethane. J Neurol Sci. 2010;292:111-3 pubmed publisher
    ..Moreover, extensive brain edema, secondary to blood-brain barrier damage or neuronal injury, is the major neuroimaging feature and the cause of clinical manifestations. Early diagnosis and prompt treatment leads to a good outcome. ..
  9. de Rivas B, López Fonseca R, Gutiérrez Ortiz M, Gutiérrez Ortiz J. Role of water and other H-rich additives in the catalytic combustion of 1,2-dichloroethane and trichloroethylene. Chemosphere. 2009;75:1356-62 pubmed publisher
    ..However, the increased presence of hydrogen atoms in the stream notably promoted the selectivity to hydrogen chloride instead of molecular chlorine. ..
  10. Mileva A, Sapundzhiev T, Beschkov V. Modeling 1,2-dichloroethane biodegradation by Klebsiella oxytoca va 8391 immobilized on granulated activated carbon. Bioprocess Biosyst Eng. 2008;31:75-85 pubmed
    ..Furthermore, immobilized cells were found to tolerate much higher substrate concentration and dilution rates in continuous culture than the free cells. ..
  11. Tsegay S, Williams R, Williams S. Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates. Carbohydr Res. 2012;357:16-22 pubmed publisher
    ..Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion. ..
  12. De Wildeman S, Linthout G, Van Langenhove H, Verstraete W. Complete lab-scale detoxification of groundwater containing 1,2-dichloroethane. Appl Microbiol Biotechnol. 2004;63:609-12 pubmed
    ..Furthermore, complete groundwater detoxification happens within a short time-frame (days) and is robust in terms of bacterial competition, oxygen tolerance, high ionic strength, and pH range. ..
  13. Koenig J, Boparai H, Lee M, O Carroll D, Barnes R, Manefield M. Particles and enzymes: Combining nanoscale zero valent iron and organochlorine respiring bacteria for the detoxification of chloroethane mixtures. J Hazard Mater. 2016;308:106-12 pubmed publisher
    ..At field sites where nZVI was applied, it is likely that in situ nZVI concentrations were below the threshold of negative consequences. ..
  14. Ma J, Li H, Spiese R, Wilson J, Yan G, Guo S. Vapor intrusion risk of lead scavengers 1,2-dibromoethane (EDB) and 1,2-dichloroethane (DCA). Environ Pollut. 2016;213:825-832 pubmed publisher
    ..As more field data of EDB and DCA become available, we recommend that USEPA consider including these data in the existing PVI database and possibly revising the PVI Guidance as necessary. ..
  15. Nikpassand M, Mamaghani M, Tabatabaeian K, Kupaei Abiazi M. KSF: an efficient catalyst for the regioselective synthesis of 1,5-diaryl pyrazoles using Baylis-Hillman adducts. Mol Divers. 2009;13:389-93 pubmed publisher
    ..A facile and convenient protocol was developed for the regioselective synthesis of 1,5-diarylpyrazoles using Baylis-Hillman adducts over KSF catalyst in high yields (70-90%) and low reaction times. ..
  16. Prudent M, Mendez M, Jana D, Corminboeuf C, Girault H. Formation and study of single metal ion-phospholipid complexes in biphasic electrospray ionization mass spectrometry. Metallomics. 2010;2:400-6 pubmed publisher
    ..The large number of ligands observed involves the formation of solvent free single ion-phospholipid complexes. ..
  17. Gwinn M, Johns D, Bateson T, Guyton K. A review of the genotoxicity of 1,2-dichloroethane (EDC). Mutat Res. 2011;727:42-53 pubmed publisher
    ..Taken together, these studies demonstrate that EDC exposure, in the presence of key enzymes (including CYP450s and/or GSTs), leads to DNA adduct formation, gene mutations and chromosomal aberrations. ..
  18. Cao X, Feng G, Gao H, Luo X, Lu H. Nanosized gamma-Al2O3 + Nd2O3-based cataluminescence sensor for ethylene dichloride. Luminescence. 2005;20:104-8 pubmed
    ..No interference or only very low levels of significant interference were observed when substances such as formaldehyde, n-hexane, methyl benzene, carbon tetrachloride, chloroform and benzene were passed through the sensor. ..
  19. Chen H, Chen H, Cooks R, Bagheri H. Generation of arylnitrenium ions by nitro-reduction and gas-phase synthesis of N-heterocycles. J Am Soc Mass Spectrom. 2004;15:1675-88 pubmed
    ..This probably involves an analogous reduction reaction by the reagent ion CH2 = CH-Cl+*. ..
  20. Schaming D, Hojeij M, Younan N, Nagatani H, Lee H, Girault H. Photocurrents at polarized liquid|liquid interfaces enhanced by a gold nanoparticle film. Phys Chem Chem Phys. 2011;13:17704-11 pubmed publisher
  21. Tang Y, Krajmalnik Brown R, Rittmann B. Modeling trichloroethene reduction in a hydrogen-based biofilm. Water Sci Technol. 2013;68:1158-63 pubmed publisher
    ..Simultaneous low concentrations of nitrate and the three chlorinated ethenes can occur as long as the influent ratio of NO3(-) to TCE is not too large, so that DHC are a significant fraction of the biofilm. ..
  22. Cottalasso D, Domenicotti C, Traverso N, Pronzato M, Nanni G. Influence of chronic ethanol consumption on toxic effects of 1,2-dichloroethane: glycolipoprotein retention and impairment of dolichol concentration in rat liver microsomes and Golgi apparatus. Toxicology. 2002;178:229-240 pubmed
    ..These data suggest that chronic ethanol consumption increases DCE liver toxicity by affecting protein glycosylation processes and impairing glycolipoprotein secretion, with a concomitant retention at the level of the Golgi apparatus. ..
  23. Laanait N, Yoon J, Hou B, Vanysek P, Meron M, Lin B, et al. Communications: Monovalent ion condensation at the electrified liquid/liquid interface. J Chem Phys. 2010;132:171101 pubmed publisher
    ..Calculations from a Poisson-Boltzmann equation that incorporates a nonmonotonic ion-specific potential of mean force are in good agreement with the data. ..
  24. Shi Y, DU X, Li H, Xu Z, Wang Q, Meng X, et al. Effects of soil temperature and agitation on the removal of 1,2-dichloroethane from contaminated soil. Sci Total Environ. 2012;423:185-9 pubmed publisher
    ..This study aims to improve the remediation of contaminated sites, especially large areas contaminated by volatile organic contaminants. ..
  25. Rodriguez Arnaiz R. Biotransformation of several structurally related 2B compounds to reactive metabolites in the somatic w/w+ assay of Drosophila melanogaster. Environ Mol Mutagen. 1998;31:390-401 pubmed
    ..The chemicals DCP, 5P2TU, and STY proved to be overall negative in IR as well as in IS strains, and SO was negative in the standard stock. Biotransformation mediated by cytochrome P450 monoxigenases to reactive metabolites is discussed. ..
  26. Maymó Gatell X, Nijenhuis I, Zinder S. Reductive dechlorination of cis-1,2-dichloroethene and vinyl chloride by "Dehalococcoides ethenogenes". Environ Sci Technol. 2001;35:516-21 pubmed
  27. Zhao R, Heng Z. [Improvement of the silver-stain and it's test and verification in comet assay]. Wei Sheng Yan Jiu. 2003;32:107-9 pubmed
    ..It can even dye the small fragments that EB-stain cannot. It is suggested that in comet assay, the silver-stain can substitute the EB-stain completely. ..
  28. Dryfe R, Hill S, Davis A, Joos J, Roberts E. Electrochemical quantification of high-affinity halide binding by a steroid-based receptor. Org Biomol Chem. 2004;2:2716-8 pubmed
    ..The strength of binding between a cholapod receptor and halide anions is quantified using voltammetry at the liquid/liquid interface, revealing very high affinities and size-selectivity peaking at chloride. ..
  29. Song J, Lee D, Lee K, Kim C. Genetic organization of the dhlA gene encoding 1,2-dichloroethane dechlorinase from Xanthobacter flavus UE15. J Microbiol. 2004;42:188-93 pubmed
    ..This unique structure of the dhlA gene organization in X. flavus strain UE15 suggested that the dechlorinase gene, dhlA, is transferred with the help of the transposase gene...
  30. Pimblott S, Milosavljevic B, Laverne J. Radiolysis of aqueous solutions of 1,1- and 1,2-dichloroethane. J Phys Chem A. 2005;109:10294-301 pubmed
  31. Falta R, Bulsara N, Henderson J, Mayer R. Leaded-gasoline additives still contaminate groundwater. Environ Sci Technol. 2005;39:379A-384A pubmed
  32. Strycharz S, Woodard T, Johnson J, Nevin K, Sanford R, Löffler F, et al. Graphite electrode as a sole electron donor for reductive dechlorination of tetrachlorethene by Geobacter lovleyi. Appl Environ Microbiol. 2008;74:5943-7 pubmed publisher
  33. Naested H, Fennema M, Hao L, Andersen M, Janssen D, Mundy J. A bacterial haloalkane dehalogenase gene as a negative selectable marker in Arabidopsis. Plant J. 1999;18:571-6 pubmed
    ..The dhlA marker therefore provides haloalkane dehalogenase reporter activity and substrate dependent negative selection in transgenic plants...
  34. Kim Y, Arp D, Semprini L. Kinetic and inhibition studies for the aerobic cometabolism of 1,1,1-trichloroethane, 1,1-dichloroethylene, and 1,1-dichloroethane by a butane-grown mixed culture. Biotechnol Bioeng. 2002;80:498-508 pubmed
    ..Thus, determining inhibition type and measuring inhibition coefficients is important in designing CAH treatment systems. ..
  35. Randazzo S, Scialdone O, Brillas E, Sirés I. Comparative electrochemical treatments of two chlorinated aliphatic hydrocarbons. Time course of the main reaction by-products. J Hazard Mater. 2011;192:1555-64 pubmed publisher
    ..Chlorine was released as Cl(-), being further oxidized to ClO(3)(-) and, mostly, to ClO(4)(-), due to the action of the largely generated BDD(OH) and OH. ..
  36. Zabrodskii P, Troshkin N, Mandych V. Stimulation of immunotoxicity of chemicals metabolizing in vivo into highly toxic compounds by the monooxygenase system inductors. Bull Exp Biol Med. 2004;138:369-71 pubmed
    ..0 LD50) metabolizing in the body to compounds with higher toxicity (phenomenon of lethal synthesis) increased immunotoxicity of these inductors. ..
  37. Zhang Q, Niu Q, Li L, Yang L, Guo X, Huang J, et al. Establishment of a poisoned animal model of toxic encephalopathy induced by 1,2-dichloroethane. Int J Immunopathol Pharmacol. 2011;24:79S-83S pubmed
    ..To declare that 1,2-DCE could induce toxic encephalopathy with a pathological feature of cerebral edema is very important for the medical rescue in urgent toxic accidents. ..
  38. Vilve M, Vilhunen S, Vepsäläinen M, Kurniawan T, Lehtonen N, Isomäki H, et al. Degradation of 1,2-dichloroethane from wash water of ion-exchange resin using Fenton's oxidation. Environ Sci Pollut Res Int. 2010;17:875-84 pubmed publisher
    ..Residual sludge, the main disadvantage in Fenton process, can be reduced by optimizing the ferrous dose or by using heterogeneous treatment where most of the reusable iron remains in the solid phase. ..
  39. Koutinas M, Baptista I, Peeva L, Ferreira Jorge R, Livingston A. The use of an oil absorber as a strategy to overcome starvation periods in degrading 1,2-dichloroethane in waste gas. Biotechnol Bioeng. 2007;96:673-86 pubmed
    ..The results of this study show that the OAB system can effectively sustain the biological treatment of waste gas during starvation periods of inhibitory pollutants...
  40. Guo J, Yuan Y, Amemiya S. Voltammetric detection of heparin at polarized blood plasma/1,2-dichloroethane interfaces. Anal Chem. 2005;77:5711-9 pubmed
    ..Despite interferences by Na+, Cl-, and plasma proteins such as serum albumin, a detection limit of 0.13 unit/mL was obtained in sheep blood plasma with the stripping method. ..
  41. Axelsson G, Barregard L, Holmberg E, Sallsten G. Cancer incidence in a petrochemical industry area in Sweden. Sci Total Environ. 2010;408:4482-7 pubmed publisher
    ..50 (0.82-2.53). VOC levels were low. Taking estimated exposure and demographic factors into account, our assessment is that occurrence of cancer was not affected by industrial emissions in any of the studied sites. ..
  42. Zhang Q, Wang L, Guo X, Niu Q. [Effect of 1, 2-dichloroethane on blood brain barrier]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2006;24:239-42 pubmed
    ..1, 2-DCE can damage blood brain barrier and induce cerebral edema. ..
  43. Preisser A, Budnik L, Hampel E, Baur X. Surprises perilous: toxic health hazards for employees unloading fumigated shipping containers. Sci Total Environ. 2011;409:3106-13 pubmed publisher
    ..These findings also emphasize the necessity for international standards on permitted fumigants, appropriate labeling in the shipping documents and handling of fumigated containers. ..
  44. Tseng T, Wang L, Ho C, Chu H. The destruction of dichloroethane over a gamma-alumina supported manganese oxide catalyst. J Hazard Mater. 2010;178:1035-40 pubmed publisher
    ..HCl and Cl(2) are the other main products with little halogenated VOC intermediates. ..
  45. Imai Y, Sugihara T, Osakai T. Electron transfer mechanism of cytochrome c at the oil/water interface as a biomembrane model. J Phys Chem B. 2012;116:585-92 pubmed publisher
    ..These findings would offer a useful suggestion for the behaviors of Cyt c in vivo. ..
  46. Alstrup Lie M, Schiøtt B. A DFT study of solvation effects on the tautomeric equilibrium and catalytic ylide generation of thiamin models. J Comput Chem. 2008;29:1037-47 pubmed
    ..Furthermore, inclusion of two water molecules to model the apoenzymatic environment lowers the activation energies of both direct and water-mediated ylide generation. ..
  47. Cui R, Li Q, Gross D, Meng X, Li B, Marquez M, et al. Anion transfer at a micro-water/1,2-dichloroethane interface facilitated by beta-octafluoro-meso-octamethylcalix[4]pyrrole. J Am Chem Soc. 2008;130:14364-5 pubmed publisher
    ..Studies such as these are expected to be useful in understanding the mechanism of anion transport at soft interfaces and for the design of yet-improved anion receptors and carriers. ..
  48. Nobre R, Nobre M. Natural attenuation of chlorinated organics in a shallow sand aquifer. J Hazard Mater. 2004;110:129-37 pubmed
    ..Therefore, a pilot test to evaluate the enhancement of these processes is being carried out through the use of a biosparging system. This test is being implemented near the source to achieve sequential aerobic-anaerobic treatment zones. ..
  49. Hage J, Van Houten R, Tramper J, Hartmans S. Membrane-aerated biofilm reactor for the removal of 1,2-dichloroethane by Pseudomonas sp. strain DCA1. Appl Microbiol Biotechnol. 2004;64:718-25 pubmed
    ..As a result, direct aeration of the water, which leads to undesired coagulation of iron oxides, could be avoided. ..
  50. Hsieh H, Wang J, Chen P, Cheng T. Synergistic effect of hepatitis virus infection and occupational exposures to vinyl chloride monomer and ethylene dichloride on serum aminotransferase activity. Occup Environ Med. 2003;60:774-8 pubmed
    ..Assessment of fitness for work should be considered in workers with hepatitis B and C infection, when they have potential exposure to hepatotoxins in the workplace. ..
  51. Zabrodskii P, Kirichuk V, Ivanov D, Mandych V. [Use of acetylcysteine and polyoxydonium for the correction of immune homeostasis and antioxidant system impaired by combined action of 1,2-dichloroethane and heavy mechanical trauma]. Eksp Klin Farmakol. 2007;70:56-8 pubmed
    ..5 LD50) reduces the suppression of immune responses and the activation of lipid peroxidation caused by these factors. ..
  52. Schultz K, Ghosh L, Banerjee S. Neoplastic expression in murine cells induced by halogenated hydrocarbons. In Vitro Cell Dev Biol. 1992;28A:267-72 pubmed
    ..These neoplastic cell lines will be useful as an in vitro model to study the role of genetic changes in the transformation processes induced by halogenated hydrocarbons. ..
  53. Jing P, Kim Y, Amemiya S. Voltammetric extraction of heparin and low-molecular-weight heparin across 1,2-dichloroethane/water interfaces. Langmuir. 2009;25:13653-60 pubmed publisher
    ..Another highly lipophilic guanidinium ionophore, N,N-dioctadecylguanidinium, cannot completely extract even Arixtra, which indicates the importance of elaborate ionophore design for heparin extraction. ..