Bis 2-chloroethyl ether

Data were last reviewed in lARC (1975) and the eompound was classified in lARC Monographs Supplement 7 (1987). 

Services Reg. No. 111-44-4 Systematic name I.I -Oxybis(2-choro)cthanc 

2 Structural and molecular formulae and relative molecular mass 

It is not clear whether bis(2-chloroethyl)ether is still produced commercially. It has been used as a solvent, a chemical intermediate and as a soil fumigant (lARC, 1975 WHO, 1998). 

Two studies have examined the risk of cancer among chlorohydrin production workers potentially exposed to bis(2-chloroethyl)ether as well as 1,2-dichloroethane and ethylene chlorohydrin (see the monograph on 1,2-dichloroethane in this volume for a detailed description of the study methods). In one study there was an excess of pancreatic, lymphatic and haematopoietic cancers (Benson Tcta, 1993), while in the other there was not (Olsen et al., 1997). In neither study was it possible to link mortality to any particular chemical exposure. 

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Chlorohydrin Process. Ethylene oxide is produced from ethylene chlorohydrin by dehydrochlorination using either sodium or calcium hydroxide (160). The by-products include calcium chloride, dichloroethane, bis(2-chloroethyl) ether, and acetaldehyde. Although the chlorohydrin process appears simpler, its capital costs are higher, largely due to material of constmction considerations (197). 

Chemical Designations - Synonyms Bis(2-chloroethyl) Ether 2,2 -Dichloroethyl Ether Dichlorodiethyl Ether Di-(2-chloroethyl) Ether Chlorex DCEE beta,beta -Dichloroethyl Ether Chemical Formula (ClCHjCH2)20. 

Pedersen s preparation of dibenzo-18-crown-6 involves catechol and bis(2-chloroethyl) ether. In this procedure, sodium hydroxide is used as base and M-butanol as solvent. The reactants are heated overnight and the crude crown is obtained by precipitation from acetone in which it is almost completely insoluble. The yield range specified is 39—48% and is readily realized. The overall preparation is illustrated in Eq. (3.11). 

C4H8CI2O Bis(2-chloroethyl)ether C4H1QO Diethyl ether... 

Tetrachloroethane Chloroethane Bis(2-chloroethyl)ether 2-Chloroethyl vinyl ether (mixed)... 

HP Sulfur Mustard and Bis(2-chloroethyl) Ether Mixture C03-A001... 

An index is included at the end of the book which lists potential sources or origins for the contaminant of concern of interest. The index also includes compounds for which degradation products are known, e.g., the presence of 1,1-dichloroethane at a site may be indicative of a release containing 1,1,1-trichloroethane (where 1,1-dichloroethane is present as an impnrity) or it may be a degradation product of 1,1,1-trichloroethane. Therefore, under the 1,1-dichloroethane entry, the reader is directed to the chemical profile 1,1,1-trichloroethane. Moreover, the index inclndes compounds which occur as additives to various products, e.g., acrolein nsually contains hydroqninone to prevent polymerization. Many commercial prodncts released into the enviromnent may contain other compounds present as impurities, e.g., 1,4-dioxane may contain the impurities acetic acid, 2-methyl-1,3-dioxolane, and bis(2-chloroethyl) ether. 

Note Bis(2-chloroethyl) ether is produced by the chlorination of ethylene glycol or by treating ethylene chlorohydrin with sulfuric acid. Therefore, either ethylene glycol or ethylene chlorohydrin may be present as impurities. 

Biological. When 5 and 10 mg/L of bis(2-chloroethyl) ether were statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, complete degradation was observed after 7 d (Tabak et al, 1981). 

Soil Based on data obtained from a 97-d soil column study, the estimated half-life of bis(2-chloroethyl) ether in soil is approximately 16.7 d (Kincannon and Lin, 1985). 

Chemical/Physical. The hydrolysis rate constant for bis(2-chloroethyl) ether at pH 7 and 25 °C was determined to be 2.6 x 10 Vh, resulting in a half-life of 3.0 yr. Products of hydrolysis include 2-(2-chloroethoxy)ethanol, bis(2-hydroxyethyl) ether, HCl, and/or 1,4-dioxane (Ellington et al., 1988 Enfield and Yates, 1990 Kollig, 1993). 

A rate constant for the vapor phase reaction of bis(2-chloroethyl) ether with OH radicals in the atmosphere has been estimated to be 3.2 x 10 cm /molecule-sec at 25 °C. At an atmospheric concentration of 5 x 10 OH radicals/cm , the corresponding half-life is 5 d (Meylan and Howard, 1993). 

Source Bis(2-chloroethyl) ether does not occur naturally in the environment. In Canada, this compound enters the environment as a by-product from chlorination of waste streams containing ethylene, propylene (Environment Canada, 1993) or ethyl ether (quoted, Verschueren, 1983). 

Note May contain acetic acid, 2-methyl-l,3-dioxolane, and bis(2-chloroethyl) ether as impurities. May be inhibited with butylated hydroxytoluene. 

Analysis of Bis(2-chloroethyl) Ether and Hydrolysis Products by Direct Aqueous Injection GC/Fourier Transform... 

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