Anthracene products

Diels-Alder reaction releasing, besides nitroxyl which can be converted to nitric oxide, a strongly blue fluorescent anthracene product 64 (Scheme 22) [99]. This reaction can therefore be followed sensitively in cell culture supernatants. Using early screening we have isolated seven different catalytic antibodies for the reaction out of approximately 12,000 individual cell culture wells resulting from fusions with ten different immunized mice. Due to early screening, the experiment was completed in a matter of weeks and comprised cloning of only a handful of antibodies [100]. 

The feedstock for anthracene production from coal tar is the anthracene fraction ( anthracene oil ), which boils between 300 and 400 °C and contains around 6% anthracene (Table 11.1). 

As a feedstock for the production of phenanthrene, the filtrate from pure anthracene production is particularly suitable (see Chapter 11.1), containing around 65% phenanthrene with an anthracene content below 10%. Distillation produces 90% pure phenanthrene the major contaminants, in terms of quantity. 

It is recovered by redistillation of the fluorene oil fraction, which boils between 290 and 305 °C (or from the distillation fore-runnings in anthracene production), followed by recrystallization, for example, from solvent naphtha. Technical fluorene, 95% pure, is commonly used to produce fluorenone by liquid-phase oxidation with air/oxygen at around 100 °C. Fluorenone can principally be used as a mild oxidant for Oppenauer oxidation, particularly in steroid chemistry. 

The first synthesis of a tri-annelated system occurred 30 years after its initial discovery from coal-tar in 1832 by Dumas and Laurent when Limpricht hydrolyzed benzyl chloride under heat to afford anthracene [laj. The most significant improvement on anthracene production, however, came in 1868 when Liebermann and Graebe obtained it via Zn-dust distillation of the natural product alizarin [la]. An interesting dimer, known as dianthracene or p-anthracene 11, was obtained by several groups in the 1890s by irradiation of anthracene solutions (Scheme 1.3) [9]. Irradiation of several anthracene derivatives afforded similarly novel structures... 

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