Terphenyle

Die Terphenyle bilden eine Stoffgruppe, die aus einem zentralen Benzolring und zwei miteinander verbundenen Phenylresten und damit aus drei Phenylringen bestehen. Durch deren unterschiedliche Anordnung der Phenylreste ergeben sich drei Konstitutionsisomere. Als kommerziell erhältliches Produkt Terphenyl stellt es eine Mischung der drei Isomere dar.

Vertreter

Name o-Terphenyl m-Terphenyl p-Terphenyl
Andere Namen 1,2-Diphenylbenzol 1,3-Diphenylbenzol 1,4-Diphenylbenzol
Strukturformel ortho-Terphenyl meta-Terphenyl para-Terphenyl
CAS-Nummer 84-15-1 92-06-8 92-94-4
26140-60-3 (Isomerengemisch)
PubChem 6766 7076 7115
Summenformel C18H14
Molare Masse 230,31 g·mol−1
Aggregatzustand fest
Kurzbeschreibung weißes, brennbares Pulver
Schmelzpunkt 54–56 °C[1] 84–88 °C[2] 213 °C[3]
Siedepunkt 332 °C[1] 379 °C[2] 404 °C[3]
Dichte 1,14 g·cm−3[1] 1,23 g·cm−3[3]
Löslichkeit Praktisch unlöslich in Wasser[3]
GHS-
Kennzeichnung
Gefahrensymbol
Achtung[1]
Gefahrensymbol Gefahrensymbol
Achtung[2]
Gefahrensymbol Gefahrensymbol
Achtung[3]
H- und P-Sätze 302 315​‐​319​‐​335​‐​400 315​‐​319​‐​335​‐​400
keine EUH-Sätze
260​‐​262 273​‐​280​‐​305+351+338​‐​337+313​‐​391 261​‐​273​‐​305+351+338
MAK Schweiz: 0,5 ml·m−3 bzw. 5 mg·m−3[4]
Toxikologische Daten 1900 mg·kg−1 (LD50, Ratte, oral)[1] 2400 mg·kg−1 (LD50, Ratte, oral)[5] 500 mg·kg−1 (LDLo, Ratte, oral)[6]

Verwendung

Das am weitesten verbreitete Terphenyl ist p-Terphenyl, welches als Farbstoff (z. B. als Dotierung von Terrylen), als Lasermaterial (z. B. für Excimerlaser mit einem Fluoreszenzmaximum bei 343 nm), als Szintillationszähler und in Sonnencremes verwendet wird. o-Terphenyl wird als Synthesechemikalie verwendet.[1] Die von den Terphenylen durch Suzuki-Kupplung abgeleiteten polychlorierten Terphenyle (PCT) weisen ähnliche physikalisch-chemische Stoffeigenschaften auf wie die polychlorierten Biphenyle (PCB) und wurden unter anderem als Wärmetauscher und Dielektrikum in Transformatoren eingesetzt.[7]

Verwandte Verbindungen

Einzelnachweise

  1. ↑ a b c d e f Eintrag zu o-Terphenyl in der GESTIS-Stoffdatenbank des IFA, abgerufen am 20. April 2017. (JavaScript erforderlich)
  2. ↑ a b c Datenblatt m-Terphenyl bei Sigma-Aldrich, abgerufen am 20. April 2017 (PDF).
  3. ↑ a b c d e Eintrag zu p-Terphenyl in der GESTIS-Stoffdatenbank des IFA, abgerufen am 20. April 2017. (JavaScript erforderlich)
  4. ↑ Schweizerische Unfallversicherungsanstalt (Suva): Grenzwerte – Aktuelle MAK- und BAT-Werte (Suche nach 26140-60-3), abgerufen am 8. Dezember 2019.
  5. ↑ Eintrag zu m-Terphenyl bei TCI Europe, abgerufen am 20. April 2017.
  6. ↑ National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review., 5(26), 1953.
  7. ↑ A. Pieper, H. Wichmann, Müfit Bahadir: Synthese und Verhalten von Polychlorierten Terphenylen (PCT) bei thermischer Belastung (Memento vom 26. September 2016 im Internet Archive)

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