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BIS(CHLOROMETHYL)ETHER

CAS No.
542-88-1
Chemical Name:
BIS(CHLOROMETHYL)ETHER
Synonyms
BCME;Bis-CME;bis-chloromethyl;bis(chloromethyl);chloromethylether;Chloromethyl ether;rcrawastenumberp016;oxybis(chloro-methan;Dichloromethyl ether;oxybis[chloro-methan
CBNumber:
CB8120955
Molecular Formula:
C2H4Cl2O
Formula Weight:
114.96
MOL File:
542-88-1.mol

BIS(CHLOROMETHYL)ETHER 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 limits TLV-TWA 0.0047 mg (0.001 ppm)/m3 (Hu man Carcinogen) (ACGIH); Human and Animal Carcinogen-Sufficient Evidence (IARC); Carcinogen (OSHA).
FDA UNII 77382IHE37
IARC 1 (Vol. 4, Sup 7, 100F) 2012
Proposition 65 List Bis(chloromethyl) Ether
EPA Substance Registry System Bis(chloromethyl) ether (542-88-1)

SAFETY

Risk and Safety Statements

Hazard Codes  T+
Risk Statements  10-36/37/38-40-26-24-22-45
Safety Statements  26-36/37/39-45-53
RIDADR  2249
HazardClass  6.1(a)
PackingGroup  I
Toxicity Acute oral LD50 for rats is 210 mg/kg (quoted, RTECS, 1985).
NFPA 704
3
4 1

BIS(CHLOROMETHYL)ETHER Chemical Properties,Uses,Production

Chemical Properties

Bis(chloromethyl)ether is a colorless, volatile liquid with a suffocating odor.

Chemical Properties

Bis(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 Properties

colorless liquid

Uses

Reagent used in the formation of ether linked dimers

Uses

Bis(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. 

Uses

Bis(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.

General Description

A 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 Reactions

Highly flammable. Insoluble in water. Reacts with water to form hydrochloric acid & formaldehyde.

Reactivity Profile

DICHLORODIMETHYL ETHER is incompatible with the following: Acids, water [Note: Reacts with water to form hydrochloric acid & formaldehyde.] .

Hazard

A carcinogen. Toxic by ingestion.

Health Hazard

BCME 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 Hazard

Acute 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 Hazard

Exposures 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 Hazard

Container 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 Exposure

Exposure 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.

Carcinogenicity

Bis(chloromethyl) ether (BCME) is known to be human carcinogens based on sufficient evidence of carcinogenicity from studies in humans.

Source

sym-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 μg/L.
Chloromethyl methyl ether may contain 1 to 8% sym-dichloromethyl ether as an impurity (Environment Canada, 1993a).

Environmental Fate

Chemical/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).

Shipping

UN2249 Dichlorodimethyl ether, symmetrical, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 3— Flammable liquid.

Toxicity evaluation

No 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.

Incompatibilities

May 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 Disposal

Incineration, 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.

50-00-0
542-88-1
Synthesis of BIS(CHLOROMETHYL)ETHER from Formaldehyde
alpha,alpha’-dichlorodimethylether alpha,alpha'-Dichlorodimethyl ether BCME bis(chloromethyl) bis-chloromethyl Bis-CME Chloro(chloromethoxy) methane chloro(chloromethoxy)methane Chloromethyl ether chloromethylether Dichlordimethylaether Dichlorodimethyl ether Dichlorodimethyl ether, symmetrical dichlorodimethylether dichlorodimethylether,symmetrical dichloromethylether,symmetrical dimethyl-1,1’-dichloroether Dimethyl-1,1-dichloroehter Dimethyl-1,1'-dichloroether Ether, bis(chloromethyl) ether,bis(chloromethyl) l’etherdebis(chloromethyle) Methane, oxybis*chloro- Methane,oxybis[chloro- oxybis(chloro)-methan oxybis(chloro-methan sym-Dichloromethyl ether sym-dichloromethylether BIS(CHLOROMETHYL)ETHER DICHLORO(ALPHA, ALPHA'-)METHYLMETHYL ETHER Dichloromethyl ether BIS(2-CHLOROMETHYL) ETHER Bis(chloromethyl)ether? chloromethyl ether syn-Dichlorodimethyl ether 2,2'-Dichlorodimether A,ADICHLORODIMETHYL ETHER Bis-(chlormethyl)ether oxybis(chloromethane) oxybis[chloro-methan oxybis[chloro-Methane Oxybis[chloromethane] oxydededichlorodimethylesymetrique Rcra waste number P016 rcrawastenumberp016 s-Di(chloromethyl) ether sym-Dichloro-dimethyl ether sym-dichlorodimethylether sym-dichloro-dimethylether bis (chloromethyl) ether oxybis(chloromethane) 1,1'-Oxybis[1-chloro-methane Bis(chloromethyl)ether Solution Methane, 1,1'-oxybis[1-chloro- Bis(chloromethyl) Ether pure, 96% 542-88-1 C2H4CI2O Miscellaneous Reagents pharmacetical Organics