Phenanthrene

Colorless plates or leaflets

Fixed

1.18 g · cm -3 ( 25 ° C)

98.5 ° C

332 ° C

12 MPa (20 ° C)

• Insoluble in water
• Soluble in benzene, diethyl ether, and glacial acetic acid

Attention

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Phenanthrene (composed of phenyl and anthracene ) is a colorless to pale yellow, crystalline solid. It is a polycyclic aromatic hydrocarbon and contains three fused benzene rings. The aromatic character is compared to the isomeric anthracene slightly more pronounced, as evidenced by a higher delocalization energy of 387 kJ / mol compared to 351.5 kJ / mol for anthracene. Phenanthrene can be found in the fraction of anthracene in coal tar, from which it is gained mainly. A derivative of phenanthrene, the sterane, is the backbone for the steroids. Phenanthrene is used for the synthesis of dyes.

Occurrence

Of course phenanthrene occurs in the form of the very rare mineral Ravatit.

Properties

Physical Properties

The colorless to yellowish crystals are odorless and fluoresce when dissolved in benzene. High purity phenanthrene melts at 98.5 ° C. The heat of fusion is 18.13 kJ / mol. At 72.8 ° C, a phase transition of higher order is observed, with a polymorphic transformation of a low temperature to a high temperature crystal form takes place. The boiling point is 332 ° C. The vapor pressure function is given by Antoine corresponding log10 (P) = A- ( B / ( T C )) ( P in bar, T in K) with A = 4.51922, B = 2428.448 and C = -70.96 in temperature range of 373 K to 423 K and with A = 4.68940 B = C = -40.7 2673.320 and in the temperature range of 477 K to 620 K. phenanthrene is almost insoluble ( 0.0011 g / l ) in water, in carbon tetrachloride, ether, benzene, toluene, and other polar organic solvents, it is readily soluble.

The flash point of the melt is 171 ° C. The ignition temperature is above 450 ° C.

Chemical Properties

The chemical behavior is determined by the specific reactivity in the 9 - and 10 - marked position. Thus, the bromination leads to the 9,10- dibromo -9 ,10- dihydrophenanthrene. When heated, this compound is an aromatic system is formed, however, under elimination of HBr with 9- bromophenanthrene again.

Reduction with lithium leads to 9,10- dihydrophenanthrene. The oxidation with chromium VI oxide yields the 9,10- phenanthrenequinone. Nitration or sulphonation, again in the 9-position.

Dangers and Metabolism

Phenanthrene irritating to eyes and skin, it is hazardous to water ( WCG 2). Phenanthrene is oxidized in the body to naphthalene, 2-diol -1.