Bis(chloromethyl) ether and technical-grade chloromethyl methyl ether
Bis(chloromethyl) ether (BCME) and technical-grade chloromethyl methyl ether (CMME) are chloroalkyl ether chemicals known for their clear, flammable liquid form and strong, unpleasant odor. Both compounds have been recognized as human carcinogens since 1980, with significant associations to lung cancer, particularly the oat-cell type, which is generally unlinked to tobacco use. Exposure to BCME and CMME can occur through inhalation, skin contact, or ingestion of contaminated water, primarily affecting workers in chemical production and research settings. These chemicals are predominantly found in chemical plants, research laboratories, and landfill sites where they have been released or disposed of. BCME can also form as a byproduct during the production of CMME, and CMME may convert to BCME through hydrolysis. The decline in the production of both chemicals in the U.S. began around 1976, with CMME remaining the only chemical still manufactured since 1982. Historically, these compounds have been utilized in various applications, including the treatment of vulcanized rubber and the manufacture of polymers and flame-retardant fabrics. Understanding the risks associated with these chemicals is crucial for those working in environments where exposure may occur.
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Bis(chloromethyl) ether and technical-grade chloromethyl methyl ether
ROC STATUS: Known human carcinogen since 1980
ALSO KNOWN AS: BCME, chloro(chloromethoxy) methane dichloromethyl ether, CMME, dimethylchloroether, methyl chloromethyl ether
RELATED CANCER: Lung cancer
DEFINITION:Bis (chloromethyl) ether (BCME) and technical-grade chloromethyl methyl ether (CMME) are chemicals known as chloroalkyl ethers. Both are clear, flammable liquids with strong, unpleasant odors.
Exposure routes: After BCME and CMME are released into the air, humans can be exposed by inhalation, dermal contact, and oral exposure via contaminated water. Potential exposure by inhalation can occur to workers who are involved in the production of BCME and CMME.
![Bis(chloromethyl ether)2. Methyl chloromethyl ether. By Toxicotravail (en.wikipedia.org/wiki/Chloroalkyl_ether) [GFDL (www.gnu.org/copyleft/fdl.html) or CC-BY-SA-3.0-2.5-2.0-1.0 (creativecommons.org/licenses/by-sa/3.0)], via Wikimedia Commons 94461852-94484.jpg](https://imageserver.ebscohost.com/img/embimages/ers/sp/embedded/94461852-94484.jpg?ephost1=dGJyMNHX8kSepq84xNvgOLCmsE2epq5Srqa4SK6WxWXS)
![Chloromethyl methyl ether 3D ball. Ball-and-stick model of the chloromethyl methyl ether molecule, an alkylating agent. By Jynto [CC0], via Wikimedia Commons 94461852-94485.jpg](https://imageserver.ebscohost.com/img/embimages/ers/sp/embedded/94461852-94485.jpg?ephost1=dGJyMNHX8kSepq84xNvgOLCmsE2epq5Srqa4SK6WxWXS)
Where found: BCME and CMME are found at production sites where they have been released into the air and at landfill sites where they have been transferred for disposal. Both are found in chemical plants where they are manufactured and in research laboratories where manufacturers use them to produce other chemicals. BCME and CMME can also be found in plants where they have been used to make several types of polymers, resins, plastics, and textiles. Small quantities of BCME can be formed as an impurity during the production of CMME. CMME can be converted to BCME through hydrolysis.
At risk: The greatest risk for contamination from BCME and CMME is to chemical-plant workers, laboratory workers, ion-exchange resin makers, and polymer producers. The general public experiences some risk from both chemicals around sites where they are produced or where they are discarded, such as landfills and surface impoundments.
Etiology and symptoms of associated cancers: Individuals exposed to BCME and CMME show significant increases in the incidence of lung carcinomas, mostly of the oat-cell type, which is generally not associated with smoking tobacco. The number of lung carcinomas is much higher in people exposed to just BCME, as compared with individuals who are exposed to both BCME and CMME. When exposed to BCME or CMME, individuals have shown a slight increase of incidence of chromosomal aberrations in peripheral lymphocytes. Both chemicals can induce unscheduled synthesis of deoxyribonucleic acid (DNA) in human fibroblasts in vitro.
History: Although BCME and CMME were previously manufactured in the United States, use of both chemicals in the United States has dropped significantly since 1976. Since 1982, only CMME is produced in the United States. In the past, BCME was used to treat vulcanized rubber to increase adhesion and in the production of flame-retardant fabrics. CMME is used as an alkylating agent and solvent in manufacturing polymers, ion-exchange resins, and water repellants.
Bibliography
Albert, R. E., et al. “Mortality Patterns among Workers Exposed to Chloromethyl Ethers: A Preliminary Report." Environmental Health Perspectives 11 (1975): 209–14. Print.
Anttila, Sisko, and Paolo Boffetta. Occupational Cancers. London: Springer, 2014. Print.
Dikshith, T. S. S. Handbook of Chemicals and Safety. Boca Raton: CRC, 2011. Digital file.
Dikshith, T. S. S. Hazardous Chemicals: Safety Management and Global Regulations. Boca Raton: CRC, 2013. Digital file.
Natl. Inst. of Environmental Health Sciences. “Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether.” Report on Carcinogens, Twelfth Edition. Research Triangle Park: US Dept. of Health and Human Services, 2011. Print.
National Toxicology Program. "Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether." 15th Report on Carcinogens, 21 Dec. 2021. www.ncbi.nlm.nih.gov/books/NBK590788/. Accessed 3 July 2024.
US Dept. of Labor. “Bis(Chloromethyl) ether.” OSHA. Occupational Safety and Health Administration, 13 May 2008. Web. 1 Oct. 2014.
US Natl. Research Council, Div. on Earth and Life Studies. Acute Exposure Guideline Levels for Selected Airborne Chemicals. Washington, DC: Natl. Acad. P, 2014. Print.