Grundinformationen
- Standard-SMILES
ClCOCCl- InChIKey
HRQGCQVOJVTVLU-UHFFFAOYSA-N- Summenformel
- C2H4Cl2O
- Durchschnittliche Molmasse
- 114,96 g/mol
- Monoisotopische Masse
- 113,96392011
Überblick
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. In the past, it 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. However, small quantities of bis(chloromethyl) ether may be formed as an impurity during the production of another chemical, chloromethyl methyl ether.
Namen und Bezeichner
- Bevorzugter Name
- Bis(Chloromethyl) Ether
- IUPAC
- chloro(chloromethoxy)methane
- Englischer Name
- Dimethyl-1,1-dichloroether
- Summenformel
- C2H4Cl2O
- Molmasse
- 0
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
542-88-1- PubChem CID
- 10967
- DTXSID
DTXSID8020173- ChEMBL
CHEMBL3185875- ChEBI
CHEBI:82270- UNII
- 77382IHE37
- EC Number
- 208-832-8
- Nikkaji
- J3.293J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 9,2 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 5
- Formalladung
- 0
- Komplexität
- 15,1
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Hazardous Air Pollutants (HAPs)
Other Classes -> Halogenated Ethers
Carcinogens
LogP
log Kow = 1.04
1.05
Density
1.315 at 68 °F (EPA, 1998) - Denser than water; will sink
1.323 g/cu cm at 15 °C
Density: 1.315 at 20 °C/4 °C
Relative density (water = 1): 1.3
1.32
1.323 @ 15°C
Solubility
Reacts with water (NIOSH, 2024)
In water, 1,020 mg/L at 25 °C
In water, 2.20X10+4 mg/L at 25 °C
Miscible with ethanol, ethyl ether
Miscible with many organic solvents
Solubility in water: reaction
Flash Point
Less than 66.2F (EPA, 1998)
Flash point < 19 °C
<19 °C (closed cup)
<66 °F
Boiling Point
223 °F at 760 mmHg (EPA, 1998)
104 °C
104-106 °C
223 °F
106 °C @760 [mm Hg]
Decomposition
Decomposed by water to /hydrochloric acid/ and formaldehyde.
When heated to decomposition it emits very toxic fumes of /chloride/.
Decomposes on contact with water, moist air, and heat, forming corrosive hydrochloric acid, hydrogen chloride, and formaldehyde vapors.
Melting Point
-42.7 °F (EPA, 1998)
-41.5 °C
-42 °C
-43 °F
-41.5 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- -41.5 °C · -41.5 °C
- Siedepunkt
- 105 °C · 105°C
- Dichte
- 1.315 at · 1.315 at 20°C
- Dampfdichte
- 4 · 4
- Flammpunkt
- 19 ° · <19°
- Farbe
- Volatile liquid
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P317, P302+P352, P303+P361+P353, P304+P340, P316, P318, P320, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P317, P302+P352, P303+P361+P353, P304+P340, P316, P318, P320, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Hazard Traits - Carcinogenicity; Dermatotoxicity; Ocular Toxicity; Respiratory Toxicity
Bis(chloromethyl) ether: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Container may explode in heat of fire. When heated to decomposition, it 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. (EPA, 1998)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Highly flammable. Vapour/air mixtures are explosive.
Fire Potential
A dangerous fire hazard.
This chemical is a flammable liquid.
Health Hazards
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. (EPA, 1998)
· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.
Hazards Summary
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. In the past, it 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. However, small quantities of bis(chloromethyl) ether may be formed as an impurity during the production of another chemical, chloromethyl methyl ether.
Bis(chloromethyl)ether (BCME) is no longer used commercially in the United States. In humans, acute (short-term) exposure to BCME may cause skin, mucous membrane, and respiratory tract irritation. Chronic bronchitis, chronic cough, and impaired respiratory function have been observed in humans following chronic (long-term) inhalation exposure. Several occupational studies have reported increased incidences of lung cancer among exposed workers. Animal studies indicate that BCME is a potent carcinogen with a short latency period. Increased incidences of respiratory tract tumors have been reported in rodents exposed by inhalation. EPA has classified BCME as a Group A, known human carcinogen.
A corrosive substance that can cause pulmonary edema; [ICSC] Bis(chloromethyl) ether and Chloromethyl methyl ether (technical grade) are listed in Table 18-3 as substances that are known human carcinogens (IARC Group 1) after occupational exposure causing lung cancer (oat cell). [Siemiatycki, p. 327]
The major hazards encountered in the use and handling of bis(chloromethyl) ether stem from its toxicologic properties and flammability. Exposure to this highly volatile, colorless liquid may occur via inhalation, ingestion, or dermal absorption from activities associated with its use as a chemical intermediate and in laboratory research. In addition, conflicting evidence exists for its spontaneous formation from formaldehyde and chloride ions (eg, hydrochloric acid (HCL) in moist air. Bis(chloromethyl) ether vapor is severely irritating to the skin, mucous membranes, and eyes. More importantly, this substance is a confirmed human carcinogen. As an OSHA regulated carcinogen, bis(chloromethyl) ether operations are prohibited in open vessels, and must employ the use of exhaust fans, protective equipment and clothing, warning signs, and labels. While mechanical ventilation must be used to minimize exposure, full body protective clothing and gloves also should be used on entering areas of potential exposure. Further, those employed in handling operations should wear full face supplied-air respirators of the continuous flow or pressure-demand type. Workers should remove and leave protective clothing and equipment at the end of the work shift for decontamination, and shower before dressing in street clothes. Smoking, drinking, application of cosmetics, and presence of food should be prohibited in the work area. Bis(chloromethyl) ether is a particularly dangerous fire hazard. In addition to being easily ignited by sparks or flames (flash point: <19 °C, closed cup), when heated to decomposition, this substance can emit hydrogen chloride fumes. Also, upon standing, this substance can form peroxides. If the substance is then heated, it can detonate. For small fires involving bis(chloromethyl) ether, extinguish with dry chemical, CO2, water spray, or foam, and for large fires use water spray, fog, or foam. Runoff from fire control water may give off poisonous gases and cause water pollution. Storage of bis(chloromethyl) ether should be in a cool, dry area, away from acids, oxidizers, or any sources of ignition (eg, open flames, hot plates). Adding antioxidants and keeping containers electrically grounded will reduce explosion potential. Containers of bis(chloromethyl) ether may be shipped via road and water (forbidden on passenger aircraft and railcar), and should be affixed with labels stating, "Poison". Before transporting bis(chloromethyl) ether, the regulatory requirements of the DOT should be consulted. For large spills of bis(chloromethyl) ether first isolate the hazard area and deny entry. Keeping upwind and staying out of low areas, use water spray to reduce vapor. Runoff should be prevented by diking. Protective clothing and a positive pressure breathing apparatus should be worn for all remedial operations. If the spill is in an enclosed space, ventilate before entering. Bis(chloromethyl) ether is a potential candidate for liquid injection, rotary kiln, and fluidized bed forms of incineration. Another method of treatment leading to the decomposition of bis(chloromethyl) ether is to inject it with ammonia in an aqueous or methanol solution. Prior to implementing land disposal of waste residue, consult with environmental regulatory agencies for guidance. Under RCRA, when bis(chloromethyl) ether becomes a waste, it must be managed according to federal and/or state hazardous waste regulations.
Special Reports
Danielson G; Hygenic Threshold Limits 5: 1-63 (1984). Tabulations of hygenic threshold limits for chemical exposures in Sweden are presented. Statutes of the Swedish Labor Board pertaining to the threshold limit values are given.
Pepelko WE; Environ Res 33 (1): 144-88 (1984). Procedures for conducting experimental studies of respiratory carcinogenesis are reviewed. Advantages and disadvantages of mice, rats, or hamsters in studies of respiratory carcinogenesis are assessed.
HHS/ATSDR; Toxicological Profile for Bis(chloromethyl) ether (1989) ATSDR/TP-89/03
RCRA Requirements
P016; As stipulated in 40 CFR 261.33, when bis(chloromethyl)ether, 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 container or inner liner used to hold this waste or 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(e)).
Sicherheit und Schutzausrüstung
Fire Fighting
Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.
Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.
Wear protective gloves when administering first aid. First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention .
Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Note: Chloromethyl ether is a recognized human carcinogen.
General First Aid:
Firefighting Hazards
Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions.
Fire Fighting Procedures
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 foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Use dry chemical, carbon dioxide, water spray, or foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces are are operated in a pressure-demand or other positive-pressure mode.
Storage Conditions
Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials. ... Store in a secure poison location. ... Store separately in a corrosive-resistant location. ... . Prior to working with this chemical you should be trained on its proper handling and storage. Before entering confined space where this chemical may be 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 the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHA Standard 1910.1045.
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
Cleanup Methods
Evacuate area. Seek professional environmental engineering assistance from the US EPA Environmental Response Team ... . Full body protective clothing and gloves should be used on entering areas of potential exposure. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. Small spills: Absorb with sand or other noncombustible material and place into containers for later disposal. Large spills: Dike far ahead of spills for later disposal. Do not let this chemical enter the environment (extra personal protection: complete protective clothing including self-contained breathing apparatus). Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.
PRECAUTIONS FOR "CARCINOGENS": A high efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms. ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal. ... The plastic bag should be sealed immediately. ... The sealed bag should be labelled properly. ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated. ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P016, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for 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.
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. 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 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.
For more Disposal Methods (Complete) data for Bis(chloromethyl) ether (11 total), please visit the HSDB record page.
Toxikologische Informationen
Interactions
... /Administration/ to skin of single dose of 1 mg ... dissolved in 0.1 mL benzene, followed by thrice weekly applications of acetone solution of 0.025 mg in 0.1 mL mixed phorbol esters from croton oil 14 days after initiation treatment ... 2 mice had squamous cell carcinomas, 1 with metastases to lung. Median survival time ... 474 days. /Controls for this experiment not discussed in this review./
... /Skin administration/ of ... a single dose of 1 mg bis(chloromethyl) ether dissolved in 0.1 mL benzene, followed by thrice weekly applications of acetone solution of 0.025 mg in 0.1 mL mixed phorbol esters from croton oil 14 days after initiation treatment, yielded papillomas in 5/20 female mice, first papilloma ... at 76 days. No tumors were seen in a control group /of mice/ which received /1 mg bis(chlormethyl) ether dissolved in 0.1 mL benzene/ as initiator and no promoting treatment.
... Pre-treatment /of mouse skin/ with 0.15 mg benzo(a)pyrene in 0.1 mL benzene solution, followed 2 wk later by thrice weekly applications of bis(chloromethyl) ether (2 mg in 0.1 mL phorbol esters) ... papillomas ... in 13/20 mice, 12 ... progressed to carcinomas. Latent period ... 98 days ... /Controls for this experiment not discussed in this review./
A possible prophylactic effect of ascorbic acid was studied in a group of 77 workers occupationally exposed to bis(chloromethyl) ether. ... The effect of prophylactic treatment was assessed by cytogenetic analysis of chromosome aberrations, of blastic transformation and mitotic index in peripheral lymphocytes. Blood samples were taken at the beginning and end of 5 mo ascorbic acid prophylaxis. ... Administration of ascorbic acid in daily doses of 1 g, 5 days/wk, decreased the frequency of aberrant cells from 3.73% to 2.13% and increased the percent of blastic transformation from 59.15 to 67.26 and mitotic index from 1.04 to 1.42. ... Smoking habits had no clear-cut effect on detected changes. Thus, the risk of genetic injury, if assessed by the frequency of chromosome aberrations in peripheral lymphocytes, was considerably reduced after ascorbic acid prophylaxis in workers occupationally exposed to halogenated ethers.
Environmental Fate
TERRESTRIAL FATE: Bis(chloromethyl) ether hydrolyzes rapidly in water(1-2). As a result, adsorption, leaching, volatilization and biodegradation in moist soil are not expected to be important environmental fate processes(SRC). Bis(chloromethyl) ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 29.4 mm g at 25 °C(3).
AQUATIC FATE: Bis(chloromethyl) ether hydrolyzes rapidly in water(1-2). As a result, adsorption to suspended solids and sediment, biodegradation, volatilization, and bioconcentration are not expected to be important fate processes in aquatic systems(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(chloromethyl) ether, which has a vapor pressure of 29.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase bis(chloromethyl) ether 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 22 days(SRC), calculated from its rate constant of 7.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Bis(chloromethyl) ether does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). Bis(chloromethyl) ether is reported to hydrolyze in humid air with half-lives of at least 18 hours(5) and >25 hours(6). However, results suggest that the hydrolysis is surface catalyzed and, therefore, may not represent the true half-life in atmospheric room air or outside air(7).
Toxicity Summary
IDENTIFICATION AND USE: Bis(chloromethyl) ether (BCME) is a colorless liquid. Historical uses of BCME include crosslinking of cellulose, preparation of styrene and other polymers, surface treatment of vulcanized rubber to increase adhesion, and manufacture of flame-retardant fabrics. It is used in the manufacture of plastics and ion exchange resins, and as a laboratory reagent. HUMAN STUDIES: Potential symptoms of overexposure include irritation of the eyes, skin, mucous membranes and respiratory system, as well as pulmonary congestion, edema, corneal damage, necrosis, decreased pulmonary function, coughing, dyspnea and wheezing, blood stained sputum, and bronchial secretions. A retrospective investigation of a small group of workers exposed to the compound between 1956 and 1962 revealed 6 cases of lung cancer among 18 men employed in a testing laboratory. Five of the 6 men were moderate smokers and 1 was a non-smoker. Two further cases were found among a group of 50 production workers. Five of the total 8 reported cases are stated to have been oat cell carcinomas. The exposure period ranged from 6-9 years and the latent period from first exposure to diagnosis was from 8-16 years. BCME induced unscheduled DNA synthesis and cell transformation in cultured human fibroblasts. A slight increase in the incidence of chromosomal aberrations was observed in blood lymphocytes of workers exposed to BCME during the preparation of ion-exchange resins. ANIMAL STUDIES: Exposure of rabbits for 3 min to atmosphere saturated with BCME caused milky corneal opacity and CNS depression. During inhalation of BCME in laboratory animal studies, irritation of the eyes and respiratory tract were noted as well as necrotizing bronchitis. Skin application resulted in erythema and necrosis. Increased mortality and tracheal hyperplasia were observed in rats and hamsters following multiple inhalation exposure. Carcinogenicity studies in experimental animals (mice and rats) exposed to BCME showed significantly elevated incidence of pulmonary adenomas and respiratory tumors. In mice, inhalation exposure also showed evidence of an elevated incidence of lung tumors. Incidence of pulmonary squamous cell carcinomas and esthesioneuroepitheliomas of the nose was described in a small series of rats exposed to inhalation of BCME in a concentration of 0.1 ppm. BCME was mutagenic in bacteria, but it did not cause chromosomal aberrations in bone-marrow cells of rats exposed to vapors for six months. BCME is among the most potent animal and human carcinogens known. Sufficient information is available to support a genotoxic mode of action.
Signs and Symptoms
Cough. Burning sensation. Wheezing. Shortness of breath. Headache. Vomiting. Laboured breathing.
MAY BE ABSORBED! Redness. Burning sensation. Skin burns.
Redness. Pain. Blurred vision. Severe deep burns.
Burns in mouth and throat. Burning sensation behind the breastbone. Abdominal pain. Shock or collapse.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for bis(chloromethyl) ether is available.[Available from, as of March 27, 2018: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]
EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of March 27, 2018: http://actor.epa.gov/dashboard/]
Effluent Concentrations
USEPA STORET DATABASE, 977 effluent data points, 1.4% pos, median <1.0 ug/L(1). Municipal solid waste leachate, Wisconsin, 5 sites, 20% pos, 250 ppb bis(chloromethyl) ether(2). Bis(chloromethyl) ether was measured (results not reported) in a 1990 hazardous air pollutants study conducted in the US(3). Bis(chloromethyl) ether was not detected in any effluent streams (total waste, total release, fugitive air, stack air, surface water) generated from Dow's Midland, MI chemical manufacturing plant in 1996(4).
EPA IRIS Information
Bis(chloromethyl)ether (BCME)
Respiratory
Regulatorische Informationen
RCRA Requirements
P016; As stipulated in 40 CFR 261.33, when bis(chloromethyl)ether, 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 container or inner liner used to hold this waste or 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(e)).
Atmospheric Standards
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Bis(chloromethyl)ether is included on this list.
CERCLA Reportable Quantities
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 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Chloromethyl ether is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.
Clean Water Act Requirements
For the maximum protection of human health from the potential carcinogenic effects of exposure to bis(chloromethyl) ether through ingestion of contaminated water and contaminated aquatic organisms, the ambient water concentrations should be zero, based on the nonthreshold assumption for this chemical. However, zero level may not be attainable at the present time. Therefore, the levels which may result in incremental increase of cancer risk over the lifetime are estimated at 10-5, 10-6, and 10-7. The corresponding recommended criteria are 37.6 x 10-6 ug/L, 3.76 x 10-6 ug/L, and 0.376 x 10-6 ug/L, respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 18.4 x 10-3 ug/L, 1.84 x 10-3 ug/L, and 0.184 x 10-3 ug/L, respectively.
Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chloroalkyl ethers/
DHS Chemicals of Interest (COI)
Chloromethyl ether
1
1000
Toxic chemical that can be released at a facility.
State Drinking Water Guidelines
(FL) FLORIDA 10 ug/L
(MN) MINNESOTA 0.002 ug/L
(NH) NEW HAMPSHIRE 0.00016 ug/L
Sicherheitsdaten
- ridadr
- UN 2249
- Toxizität
- LD50 orl-rat: 210 mg/kg AIHAAP 30,470,69
- hazard_class
- 6.1
- packing_group
- I
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Uses
In the past, BCME was used for chloromethylation and as an alkylating agent in the manufacture of polymers. BCME is no longer used commercially in the United States. It is used as a research chemical and lab reagent.
Used in the past to make polymers, resins, and textiles; Currently, only small amounts are used in enclosed systems in the chemical industry. [ACGIH]
Regulated as a carcinogen; See 29CFR1910.1003;
Historical uses of BCME include crosslinking of cellulose, preparation of styrene and other polymers, surface treatment of vulcanized rubber to increase adhesion, and manufacture of flame-retardant fabrics.
Intermediate for ion-exchange resins; laboratory reagent.
... No longer used for chloromethylation in industry; however, it is used as the monitoring indicator for chloromethyl ether, because of its greater stability in workroom air.
U.S. Production
(1977) AT LEAST 4.54X10+7 G
(1982) NOT PRODUCED COMMERCIALLY IN USA
ALTHOUGH BIS(CHLOROMETHYL) ETHER MAY BE PRODUCED IN UNITED STATES AS CHEM INTERMEDIATE, NO EVIDENCE WAS FOUND THAT IT IS PRODUCED ON A COMMERCIAL SCALE FOR SALE TO OTHERS. ... SALES ... LIMITED TO LAB QUANTITIES.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…