“Bis(chloromethyl) ether”的意思、由来-开放百科全书

Bis(chloromethyl) ether is an organic compound with the chemical formula (CH₂Cl)₂O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale, but was found to be highly carcinogenic and thus such production has all but ceased.

Synthesis

It was produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid.^[3] It is also produced as a by-product in the Blanc chloromethylation reaction, formed when formaldehyde (the monomer, paraformaldehyde or formalin) and concentrated hydrochloric acid are mixed, and is a known impurity in technical grade chloromethyl methyl ether.

Because of their carcinogenic potency, the industrial production of chloromethyl ethers ended in most countries in the early 1980s. Bis(chloromethyl) ether was no exception to this with production in the U.S.A. ending in 1982.

Uses

Bis(chloromethyl) ether has been extensively used in chemical synthesis, primarily as a crosslinking agent in the manufacture of ion-exchange resins and in the textile industry. It was also used as a linker in the synthesis of certain nerve agent antidotes (asoxime chloride, obidoxime).

Bis(chloromethyl) was also effective for chloromethylation of aromatic substrates.^[4]

Safety

Bis(chloromethyl) ether is carcinogenic.^[5]^[6] It is one of 13 chemicals considered an OSHA-regulated occupational carcinogen.^[7] Chronic exposure has been linked to in increased risk of lung cancer.^[5]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[8]

See also

References

1. ^{{cite journal|last1=Evans|first1=L.|last2=Gray|first2=R.|title=Notes - Preparation of Certain Polychlorodimethyl Ethers|journal=The Journal of Organic Chemistry|date=May 1958|volume=23|issue=5|pages=745–746|doi=10.1021/jo01099a602}}
2. ^¹²³⁴⁵{{PGCH|0128}}
3. ^Wilhelm Heitmann, Günther Strehlke, Dieter Mayer “Ethers, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI| 10.1002/14356007.a10_023}}
4. ^{{cite journal|last1=Olah|first1=George A.|last2=Beal|first2=David A.|last3=Olah|first3=Judith A.|title=Aromatic substitution. XXXVIII. Chloromethylation of benzene and alkylbenzenes with bis(chloromethyl)ether, 1,4-bis(chloromethoxy)butane, 1-chloro-4-chloromethoxybutane, and formaldehyde derivatives|journal=The Journal of Organic Chemistry|date=April 1976|volume=41|issue=9|pages=1627–1631|doi=10.1021/jo00871a032}}
5. ^¹{{cite web|title=Bis(chloromethyl)ether (BCME) (CASRN 542-88-1)|url=http://www.epa.gov/iris/subst/0375.htm|publisher=U.S. environmental protection agency|accessdate=26 November 2014|ref=EPA}}
6. ^{{cite journal|last1=Van Duuren|first1=BL|title=Comparison of potency of human carcinogens: vinyl chloride, chloromethylmethyl ether and bis(chloromethyl)ether.|journal=Environmental research|date=August 1989|volume=49|issue=2|pages=143–51|pmid=2526731|doi=10.1016/s0013-9351(89)80059-3}}
7. ^{{cite web|title=NIOSH Pocket Guide to Chemical Hazards: bis-Chloromethyl ether|url=https://www.cdc.gov/niosh/npg/npgd0128.html|publisher=Centers for Disease Control and Prevention|accessdate=26 November 2014}}
8. ^{{Cite journal | publisher = Government Printing Office | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = July 1, 2008 | accessdate = October 29, 2011 | postscript=.}}