| | BIS(CHLOROMETHYL)ETHER Basic information |
| | 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 | | Fp | 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). | | IARC | 1 (Vol. 4, Sup 7, 100F) 2012 | | EPA Substance Registry System | Bis(chloromethyl) ether (542-88-1) |
| | BIS(CHLOROMETHYL)ETHER Usage And Synthesis |
| Description | Bis(chloromethyl) ether is a colorless, volatileliquid with a suffocating odor. Molecular weight=115.0.Specific gravity (H2O:1)=1.32 at 25℃; Boilingpoint=106.1℃; Freezing/Melting point=-42℃; Vaporpressure=30 mmHg at 25℃; Flash point=# 18.8℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 4, Flammability 3, Reactivity 1 .Insoluble in water (decomposes, creating hydrogenchloride). | | 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 | | Chemical Properties | Bis(chloromethyl)ether is a colorless, volatile
liquid with a suffocating odor. | | 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. | | 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 | Reagent used in the formation of ether linked dimers | | Definition | ChEBI: Bis(chloromethyl) ether is an ether that is dimethyl ether in which one of the hydrogens attached to each of the methyl group has replaced by a chlorine. It has a role as a carcinogenic agent and an alkylating agent. It is an ether and an organochlorine compound. | | 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 | 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. | | 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. | | 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. | | First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray. | | 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). | | storage | (1) Color Code—Red: Flammability Hazard:Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactivematerials. (2) Color Code—Blue: Health Hazard/Poison:Store in a secure poison location. Color Code—White:Corrosive or Contact Hazard; Store separately in a corrosion-resistant location. Color Code—Green: General storage may be used. Prior to working with this chemical youshould be trained on its proper handling and storage.Before entering confined space where this chemical maybe present, check to make sure that an explosive concentration does not exist. Store in airtight containers in a cool,dry, well-ventilated area. Metal containers involving thetransfer of this chemical should be grounded and bonded.Where possible, automatically pump liquid from drums orother storage containers to process containers. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof this chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard. A regulated, marked area shouldbe established where this chemical is handled, used, orstored in compliance with OSHA Standard 1910.1045. | | 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. |
| | BIS(CHLOROMETHYL)ETHER Preparation Products And Raw materials |
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