2,3,6,7-tetrachloronaphthalene
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| General | ||||||||||
| Surname | 2,3,6,7-tetrachloronaphthalene | |||||||||
| other names |
PCN 48 |
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| Molecular formula | C 10 H 4 Cl 4 | |||||||||
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| properties | ||||||||||
| Molar mass | 265.95 g mol −1 | |||||||||
| Physical state |
firmly |
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| density |
1.676 g cm −3 |
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| Melting point |
203-204 ° C |
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| Sublimation point |
135 ° C |
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| safety instructions | ||||||||||
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| MAK |
Switzerland: 2 mg m −3 (measured as inhalable dust ) |
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| Toxicological data |
> 3 mg · kg -1 ( LD 50 , guinea pigs , oral ) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
2,3,6,7-Tetrachloronaphthalene is a chlorinated derivative of naphthalene . Although the structure is similar to the Sevesodioxin become known compound 2,3,7,8-Tetrachlorodibenzodioxin , but one of the p oly c hlorierten N aphthalinen (short PCN ) and not to the dioxins .
Extraction and presentation
The 2,3,6,7-tetrachloronaphthalene can be prepared in an 11-step synthesis from 3,4-dichlorophthalic anhydride . In 1962 it was first synthesized by Reimlinger and King.
properties
Physical Properties
2,3,6,7-Tetrachloronaphthalene forms white needles and sublimates at 135 ° C. The compound crystallizes in a monoclinic lattice. In the infrared spectrum of the substance, absorption bands appear at the wave numbers 1638, 1478, 1458, 1346, 1177, 965, 902, 761 and 650. In the nuclear magnetic resonance spectrum, a solution in hexadeuterobenzene shows hydrogen atoms at 7.10 ppm (400 M Hz , s, 4 H), carbon atoms at 128.4 (quart.), 127.6 (quart.) And 128, 0 (tert.) Ppm (100 MHz).
Chemical properties
In a 15-hour electrolysis at −2.2 volts on the working electrode , up to 98% of 2,3,6,7-tetrachloronaphthalene could be degraded to low-chlorinated or halogen-free naphthalene derivatives.
Individual evidence
- ↑ a b c d e Reimlinger, H .; King, G .: About the representation of some polychloronaphthalenes in Chem. Ber. 95 (1962), 1043-1048, doi : 10.1002 / cber.19620950436 .
- ↑ a b c Levy, LA: The Synthesis Of 2,3,6,7-Tetrasubstituted Naphthalenes: 2,3,6,7-Tetrachloronaphthalene in Synth. Common. 13 (1983), 639-648, doi : 10.1080 / 00397918308060343 .
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 34588-40-4 or 2,3,6,7-tetrachloronaphthalene ), accessed on November 2, 2015.
- ^ Concise International Chemical Assessment Document (CICAD) for Chlorinated Naphthalenes , accessed December 9, 2014.
- ^ Giachino, GG: Phosphorescence spectra and lifetimes of symmetrical tetrachloronaphthalenes in J. Phys. Chem. 84 (1980), 3522-3524, doi : 10.1021 / j100463a006 .
- ↑ J. Voss , M. Altrogge, D. Golinske, O. Kranz, D. Nünnecke, D. Petersen, E. Waller: Degradation of Chlorinated Arenes by Electroreduction in Treatment of Contaminated Soil - Fundamentals, Analysis, Applications (Eds .: R. Stegmann, G. Brunner, W. Calmano, G. Matz), Springer Verlag, Berlin, Heidelberg, New York, 2001, pp. 547-563, doi : 10.1007 / 978-3-662-04643-2 ( restricted Preview in Google Book Search, especially pp. 550–551).