Bis(2-chloroethoxy)methane

173.04

173.04

203-920-2

5288KK0810

5212

2810

DTXSID4023917

Colorless liquid

2909199090

18.5

0.75 (est)

Bis(2-chloroethoxy)methane, [liquid] appears as a colorless liquid. Boiling point 217.5°C, Flash point 230°F. Density 1.23 g / cm3. May be toxic by ingestion or inhalation. Severely irritates skin, eyes, and mucous membranes. Used as a solvent.

1.2339 g/cm³ @ Temp: 20 °C

-32 °C

218.1 °C

230 DEG F (110 DEG C) (OPEN CUP)

1.45

In water, 7,800 mg/l at 20 deg C

Materials which are toxic as stored or which can decomp into toxic components due to contact with heat, moisture, acid, or acid fumes, should be stored in cool, well-ventilated place, out of direct rays of sun, away from areas of high fire hazard and should be periodically inspected and monitored.

1 at 53 °C (Weast, 1986)

5.9 (Air= 1)

Acute oral LD 50 for rats 65 mg/kg (quoted, RTECS, 1985).

Decomp by mineral acids|Conversion factors: 1 mg/l= 141 ppm; 1 ppm= 7.1 mg/cu m

Slightly soluble in water.

Ethers

BIS(2-CHLOROETHOXY)METHANE, [LIQUID], the b-chloroethyl acetal of formaldehyde, is incompatible with oxidizing agents.

12908.9 G CAL/G MOLE

III

6.1(b)

2810

25

45

Xi,T

P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

H301

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U024, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

Oxidizing materials.|On contact with acids or acid fumes they evolve highly toxic /hydrogen chloride/ fumes. /Chlorides/

USEPA; Ambient Water Quality Criteria Doc: Chloroalkyl Ethers (1980) EPA 440/5-80-030.|USEPA; Health and Environmental Effects Profile for Bis(2-chloroethoxy) methane; (1980) ECAO-CIN-23.

Not Flammable. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P307+P311, P310, P312, P314, P320, P321, P322, P330, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 106 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)

Combustible.|Combustible when exposed to heat or flame.

To fight fire, use alcohol foam, foam, CO2 or dry chemical.|"Alcohol" foam. Water or foam may cause frothing.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

Irritating to skin and eyes.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

The major hazards encountered in the use and handling of bis(2-chloroethoxy) methane stem from its toxicologic properties. Toxic primarily via dermal contact and inhalation, exposure to this colorless liquid may occur from its manufacture and use as a solvent and intermediate for polysulfide rubbers. Effects from exposure may include irritation of the skin and eyes. Local exhaust ventilation should be used to limit exposure. In activities and situations where over-exposure may occur, wear a full facepiece, self-contained breathing apparatus. While bis(2-chloroethoxy) methane must be preheated before ignition can occur, when heated to decomposition it emits toxic fumes of hydrochloric acid. For fires involving this substance, extinguish with dry chemical or CO2. Also, water fog gently applied to the surface of the liquid will cause a frothing which will extinguish the fire. This substance should be stored in cool, well-ventilated areas, away from direct rays of the sun, fire hazards, moisture, acids, and other oxidizing materials. Bis(2-chloroethoxy) methane is a potential candidate for disposal by fluidized bed, rotary kiln, or liquid injection forms of incineration.

U024; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U024; As stipulated in 40 CFR 261.33, when dichloromethoxy ethane, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

... Has been monitored in rubber plant effluents at a maximum level of 140 mg/l.|Bis(2-chloroethoxy)methane was qualitatively detected in disposal trench leachate samples collected from commercially operated low-level radioactive disposal sites at Maxey Flats, KY, and at West Valley, NY(1). Bis(2-chloroethoxy)methane was detected in 1.0% of 1,243 samples from the USEPA STORET Data Base with a median concn less than 10 ug/l(2). Bis(2-chloroethoxy)methane was detected in 11 of 129 raw water extracts at 11 water utilities in the Ohio River Basin (between 1977-78) at concn less than 0.1 ug/l(3).

From the USEPA STORET Data Base, bis(2-chloroethoxy)methane has been detected in 0% of 344 sediment samples. Bis(2-chloroethoxy)methane was not found in sediments from Lake Pontchartrain, LA(2).

LD50 Rat (Sherman) oral 65 mg/kg|LD50 Guinea pig dermal 170 mg/kg

Bis(2-chloroethoxy)methane's production and use as a solvent and chemical intermediate for polysulfide rubber(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a water solubility of 7,800 mg/l(2) and a regression-derived equation(3), indicates that bis(2-chloroethoxy)methane is expected to have very high mobility in soil(SRC). Volatilization of bis(2-chloroethoxy)methane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.132 mm Hg(4), and water solubility, 7,800 mg/l(2). Bis(2-chloroethoxy)methane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Based upon studies in water(5,6), bis(2-chloroethoxy)methane is not expected to degrade in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a water solubility of 7,800 mg/l(2) and a regression-derived equation(3), indicates that bis(2-chloroethoxy)methane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.132 mm Hg(4), and water solubility, 7,800 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8.4 and 96 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 4(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-life for similar beta-chloro ethers has been estimated at 0.5-2 years, a process which is pH independent(7). Bis(2-chloroethoxy)methane is not expected to readily biodegrade in the environment(SRC); bis(2-chloroethoxy)methane underwent 0% biodegradation using a settled domestic wastewater inoculum and biodegradation remained at 0% through three subcultures(8,9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-chloroethoxy)methane, which has a vapor pressure of 0.132 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase bis(2-chloroethoxy)methane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.1 days(SRC), calculated from its rate constant of 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Bis(2-chloroethoxy)methane would not be expected to undergo direct photolysis in surface waters or the troposphere since the compound does not possess any chromophores that absorb radiation in the visible or near ultraviolet regions of the electromagnetic spectrum.|There are two sites within this molecule wherein hydrolysis could take place: (1) the carbon-oxygen bonds of the acetal linkage and (2) the carbon-chlorine bonds. The maximum hydrolytic half-life in pure water at pH 7 and 25 °C has been estimated to be within the range of thousands of years for the acetal linkage and approximately six months for the carbon-chloride bonds.|The rate constant for the vapor-phase reaction of bis(2-chloroethoxy)methane with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The estimated hydrolysis half-life of bis(2-chloroethoxy)methane was reported as 0.5-2 years (pH independent), based on analogy to similar beta-chloro ethers(3). Bis(2-chloroethoxy)methane is not expected to directly photolyze due to the lack of absorption in the environmental portion of the UV spectrum (>290 nm)(SRC).

An estimated BCF of 4 was calculated for bis(2-chloroethoxy)methane(SRC), using a water solubility of 7,800 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

61.66 L/kg|The Koc of bis(2-chloroethoxy)methane is estimated as 32(SRC), using a water solubility of 7,800 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bis(2-chloroethoxy)methane is expected to have very high mobility in soil(SRC).

The Henry's Law constant for bis(2-chloroethoxy)methane is estimated as 3.9X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 0.132 mm Hg(1), and water solubility, 7,800 mg/l(2). This Henry's Law constant indicates that bis(2-chloroethoxy)methane is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 8.4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 96 days(SRC). Bis(2-chloroethoxy)methane's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur slowly(SRC). Bis(2-chloroethoxy)methane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: Bis(2-chloroethoxy)methane was detected in 0.1% of 834 samples from the USEPA STORET Data Base, with a median concn less than 10 ug/l(1). Bis(2-chloroethoxy)methane was not detected in 86 samples from 51 rainwater runoff catchments located throughout the United States (detection limits not given)(2). Bis(2-chloroethoxy)methane was identified in one of eleven samples and three of ten samples along the Ohio River, Wheeling, WV, (mile point 86.8) and Evansville, KY (mile point 791.5), respectively, in concn less than or equal to 0.1 ug/l, between the years 1977-1978(3). This compound was not found in eighty-two other stations along the river(3).

Occupational exposure to bis(2-chloroethoxy)methane may occur through inhalation and dermal contact with this compound at workplaces where bis(2-chloroethoxy)methane is produced or used. (SRC)

Reaction product contains ethylene chlorohydrin impurity ... for use in polysulfide polymers, the ethylene chlorohydrin must be removed because it would act as a chain terminator in the polymerization

ACUTE/CHRONIC HAZARDS: Toxic by inhalation and ingestion; Strong irritant. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/HUMAN EXPOSURE STUDIES/ Toxic by inhalation and ingestion, strong irritant.

bis(2-chloroethoxy)methane

Essentially 100% as chemical intermediate for polysulfide rubbers.

Ethane, 1,1'-[methylenebis(oxy)]bis[2-chloro-: ACTIVE

Method: EPA-EAD 611, Haloethers in Water by GC/Electrolytic Conductivity Detector; Analyte: bis(2-chloroethoxy)methane; Matrix: water; Detection Level: 0.5 ug/L.|Method: EPA-NERL 625, Base/Neutrals and Acids; Analyte: bis(2-chloroethoxy)methane; Procedure: GC/MS; Matrix: water; Detection Level: 5.3 ug/L.|Method: DOE OM100R, Semivolatile Organic Compounds in Multimedia Samples by Capillary Column Ion Trap MS; Analyte: bis(2-chloroethoxy)methane; Matrix: water; Detection Level: 56 ug/L.|Method: EPA-OSW 8270D, Semivolatile Organic Compounds by GC/MS; Analyte: bis(2-chloroethoxy)methane; Matrix: various (solid waste matrices, soils, air sampling media and water samples); Detection Level: 10 ug/L.|For more Analytic Laboratory Methods (Complete) data for BIS(2-CHLOROETHOXY)METHANE (6 total), please visit the HSDB record page.