Chemistry:Tetrachlorobenzene
From HandWiki
Tetrachlorobenzene is any of three isomeric chlorobenzenes with the molecular formula C
6H
2Cl
4. They differ by the positions of the chlorine atoms around the ring. Tetrachlorobenzenes are colorless crystalline compounds.[1]
Properties
| isomer | m.p. (°C) | b.p. (°C) | m.p. (g/cm3 @100 °C) |
|---|---|---|---|
| 1,2,3,4 | 47 | 254 | 1.539 |
| 1,2,3,5 | 51.5 | 246 | 1.523 |
| 1,2,4,5 | 141 | 245 | 1.454 |
Synthesis
1,2,4,5-Tetrachlorobenzene can be produced by electrophilic halogenation of benzenes and some chlorobenzenes.[2] 1,2,3,4-Tetrachlorobenzene can only be produced by chlorination of 1,3,5-trichlorobenzene.
Uses
1,2,4,5-Tetrachlorobenzene once was used in the production of the herbicide 2,4,5-trichlorophenoxyacetic acid. This method has been discontinued because it produced highly toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin as a waste product.[1][3][4]
See also
- Tetrabromobenzene
- Tetraiodobenzene
References
- ↑ 1.0 1.1 Beck, Uwe; Löser, Eckhard (2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o06_o03. ISBN 9783527303854.
- ↑ "US4205014A Process for 1,2,4,5-tetrachlorobenzene". Espacenet. https://worldwide.espacenet.com/patent/search/family/026711356/publication/US4205014A?q=pn%3DUS4205014A.
- ↑ (in en) NTP Toxicity Study Reports. National Toxicology Program. 1991. p. 11. https://books.google.com/books?id=4mrSWQi2luwC&dq=%2522Tetrachlorobenzene%2522&pg=PA11. Retrieved 22 June 2023.
- ↑ "New Chlorobenzene Pesticides, Their Impacts on Environment and Food Quality". International Journal of Engineering Research and Science & Technology. November 2012. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=272780c09baeee7985e9fab16809f267ce415801.
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