BIS(CHLOROMETHYL)ETHER Chemical Properties
- Melting point:171℃
- Boiling point:106℃
- Density 1.267
- vapor pressure 30 at 22 °C (Dreisbach, 1952)
- refractive index 1.44433
- Flash point:75℃
- storage temp. -20°C Freezer
- solubility Soluble in alcohol, ether (Weast, 1986), benzene (Hawley, 1981), and other solvents including acetone and chloroform.
- form Colorless liquid
- color Colorless liquid with a suffocating odor
- Exposure limitsTLV-TWA 0.0047 mg (0.001 ppm)/m3 (Hu man Carcinogen) (ACGIH); Human and Animal Carcinogen-Sufficient Evidence (IARC); Carcinogen (OSHA).
- IARC1 (Vol. 4, Sup 7, 100F) 2012
- EPA Substance Registry SystemBis(chloromethyl) ether (542-88-1)
BIS(CHLOROMETHYL)ETHER Usage And Synthesis
- Chemical Propertiescolorless liquid
- Chemical PropertiesBis(chloromethyl) ether is a clear liquid with a strong unpleasant odor. It does not occur naturally. It dissolves easily in water, but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities produced are only used in enclosed systems to make other chemicals. However, small quantities of bis(chloromethyl) ether may be formed as an impurity during the production of chloromethyl methyl ether. Along with other chemicals, rain, and sunlight, it undergoes chemical reactions and breaks down as formaldehyde and hydrochloric acid
- Chemical PropertiesBis(chloromethyl)ether is a colorless, volatile liquid with a suffocating odor.
- UsesBis(chloromethyl)ether (BCME) is used asan intermediate in anion-exchange quater nary resins. Its use as a chloromethylationreagent in industry is being discontinuedbecause of its high carcinogenic properties.Exposure risks associated with this com pound can arise during the use or productionof chloromethyl methyl ether when the lat ter compound comes in contact with tracesof water in the presence of hydrogen orhydroxyl ions. It may occur in trace amountsin chloromethyl methyl ether.
- UsesBis(chloromethyl) ether is a clear liquid with a strong unpleasant odour. It does not occur naturally. It dissolves easily in water but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities that are produced are only used in enclosed systems to make other chemicals.
- UsesReagent used in the formation of ether linked dimers
- General DescriptionA colorless volatile liquid with a chloroform-like odor. Toxic by inhalation, skin absorption and ingestion. Dangerous fire risk - flash point below 0°F. Vapors much denser than air. Insoluble in water and denser than water. Used to make paints and varnish, and as a solvent.
- Air & Water ReactionsHighly flammable. Insoluble in water. Reacts with water to form hydrochloric acid & formaldehyde.
- Reactivity ProfileDICHLORODIMETHYL ETHER is incompatible with the following: Acids, water [Note: Reacts with water to form hydrochloric acid & formaldehyde.] .
- HazardA carcinogen. Toxic by ingestion.
- Health HazardBCME is a highly toxic and carcinogeniccompound. The inhalation toxicity and car cinogenicity of this compound are greatestamong the haloethers
Exposure to its vapors can cause irritationof the eyes, nose, and throat in humans. Theprimary target organ is the lungs. Inhalationof 100 ppm of this compound in air for afew minutes can cause death to humans.Irritation of the eyes can be moderate tosevere and conjunctival. The acute oral anddermal toxicity of this compound, however,is moderate and comparable to that of bis(2-chloroethyl)ether
LC50 value, inhalation (rats): 33 mg (7ppm)/m3/7 hr
LD50 value, oral (rats): 210 mg/kg (NIOSH1986)
Tests on animals have confirmed the car cinogenic action of BCME. It is carcinogenicby inhalation and by subcutaneous and skinapplications. In humans it can produce lungcancer — a fact that is now well established.Tests on rats indicate that exposure to 0.1-ppm concentrations in air for 6 hours per dayfor 6 months produced tumors in the noseand lungs. Subcutaneous and skin applicationsproduced tumors at the site of application.
- Health HazardAcute toxicity is high by ingestion, inhalation, and skin irritation. Small quantities may cause death or permanent injury after very short exposure. Chloromethyl ether is an alkylating agent which is a recognized human carcinogen. There is a strong association between industrial exposure and excess lung cancer.
- Health HazardExposures to bis(chloromethyl) ether cause irritation to the skin, eyes, throat, and lungs, and in cases of severe exposures cause damage to the lungs (swelling and bleeding) and death. Breathing low concentrations will cause coughing and nose and throat irritation.
- Fire HazardContainer may explode in heat of fire. When heated to decomposition, BIS(CHLOROMETHYL)ETHER emits very toxic fumes of chlorides. Decomposed by water to hydrochloric acid and formaldehyde. Avoid water: hydrolyzes very rapidly (half life 10-40 seconds) on contact with water. Avoid decomposing heat, powerful oxidizers, areas of high fire hazard and moist air.
- Potential ExposureExposure to bis(chloromethyl)ether may occur in industry and in the laboratory. This substance can form spontaneously in warm moist air by the combination of formaldehyde and hydrogen chloride. This compound is used as an alkylating agent in the manufacture of polymers; as a solvent for polymerization reactions; in the preparation of ion exchange resins; and as an intermediate for organic synthesis. Haloethers, primarily α-chloromethyl ethers, represent a category of alkylating agents of increasing concern due to the establishment of a causal relationship between occupational exposure to two agents of this class and lung cancer in the United States and abroad. The cancers are mainly oat cell carcinomas. Potential sources of human exposure to BCME appear to exist primarily in areas including: (1) its use in chloromethylating (crosslinking) reaction mixtures in anion-exchange resin production; (2) segments of the textile industry using formaldehydecontaining reactants and resins in the finishing of fabric and as adhesive in the laminating and flocking of fabrics; and (3) the nonwoven industry which uses as binders, thermosetting acrylic emulsion polymers comprising methylol acrylamide, since a finite amount of formaldehyde is liberated on the drying and curing of these bonding agents. NIOSH has confirmed the spontaneous formation of BCME from the reaction of formaldehyde and hydrochloric acid in some textile plants and is now investigating the extent of possible worker exposure to the carcinogen. However, this finding has been disputed by industrial tests in which BCME was not formed in air by the reaction of textile systems employing hydrochloric acid and formaldehyde.
- CarcinogenicityBis(chloromethyl) ether (BCME) is known to be human carcinogens based on sufficient evidence of carcinogenicity from studies in humans.
- Sourcesym-Dichloromethyl ether may form as an intermediate by-product when form-aldehyde
reacts with chloride ions under acidic conditions (Frankel et al., 1974; Tou and Kallos, 1974a;
Travenius, 1982). Tou and Kallos (1974) reported that the reactants (formaldehyde and chloride
ions) must be in concentrations of mg/L to form sym-dichloromethyl ether at concentrations of
Chloromethyl methyl ether may contain 1 to 8% sym-dichloromethyl ether as an impurity (Environment Canada, 1993a).
- Environmental FateChemical/Physical. Reacts rapidly with water forming HCl and formaldehyde (Fishbein, 1979;
Tou et al., 1974). Tou et al. (1974) reported a hydrolysis half-life of 38 sec for sym-dichloromethyl
ether at 20 °C.
Anticipated products from the reaction of sym-dichloromethyl ether with ozone or OH radicals in the atmosphere, excluding the decomposition products formaldehyde and HCl, are chloromethyl formate and formyl chloride (Cupitt, 1980).
- ShippingUN2249 Dichlorodimethyl ether, symmetrical, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 3— Flammable liquid.
- Toxicity evaluationNo information is available on the transport and partitioning
of BCME in the environment. Due to the relatively short
half-life in both air and water, it is unlikely that significant
partitioning between media or transport occurs. Primary
process for BCME degradation in air is believed to be reaction
with photochemically generated hydroxyl radicals to yield
chloromethyl formate ClCHO, formaldehyde, and HCl.
Atmospheric half-life due to reaction with hydroxyl radicals is
estimated to be 1.36 h. Hydrolysis in the vapor phase is found
to be slower with an estimated half-life of 25 h.
BCME is rapidly hydrolyzed in water to yield formaldehyde and HCl, and the hydrolysis rate constant is estimated to be 0.018 s-1at 20°C, which is equal to a half-life of ～35 s.
No information is available on the fate of BCME in soil. It is probable that BCME would rapidly degrade upon contact with moisture in soil. Due to its high volatile nature, it is not expected that BCME would persist in soil for significant periods.
- IncompatibilitiesMay form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Decomposes on contact with water, moist air, and heat, forming corrosive hydrochloric acid, hydrogen chloride, and formaldehyde vapors. May form shocksensitive compounds on contact with oxidizers, peroxides, and sunlight. Attacks many plastics.
- Waste DisposalIncineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
BIS(CHLOROMETHYL)ETHER Preparation Products And Raw materials
- Preparation Products3,4-DimethylanilineDiethyl(acetylamino)((2-((bis(2-hydroxyethyl)amino)methyl)-5-nitrophenyl)methyl)propanedioateIsofluraneDIETHYL 2-(ACETAMIDO)-2-(2-(BROMOMETHYL)-5-NITROBENZYL)MALONATEDiethyl(acetylamino)((2-((bis(2-chloroethyl)amino)methyl)-5-nitrophenyl)methyl)propanedioateDIETHYL 2-(ACETAMINDO)-2-(2-METHYL-5-NITROBENZYL)MALONATE2-(Chloromethyl)-1-methyl-4-nitrobenzene
- Raw materialsParaformaldehyde
- Diphosgene BIS(CHLOROMETHYL)ETHER BIS(2-CHLOROISOPROPYL)ETHER Glycerine α,γ-bis(chloromethyl) ether Ethylene glycol bis(chloromethyl) ether 1-Chloroethyl chloroformate 2-CHLORO-2-(CHLORODIFLUOROMETHOXY)-1,1,1-TRIFLUOROETHANE ALPHA-CHLORO-2-(TRIFLUOROMETHYL)BENZYL CHLOROFORMATE SALOR-INT L160873-1EA ISOBENZAN BIS(ALPHA-CHLOROETHYL)ETHER AKOS BBS-00005207 Chloromethyl chloroformate 1,2,3-Trichloropropane-2,3-oxide tetrachloroepoxyethane DIPHOSGENE [CARBONYL-14C] 1,1-DICHLORO-2,2,2-TRIFLUOROETHYL CHLORODIFLUOROMETHYL ETHER (+/-)-1,2,2,2-TETRACHLOROETHYL CHLOROFORMATE