Diphenic acid from phenanthrene

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

Diphenic acid was first prepared by oxidizing phenanthrene-quinone with chromic acid.1 Many later workers2 have modified this process in minor details. Vorlander and Meyer 3 were the first to prepare diphenic acid from diazotized anthranilic add and cuprous oxide, but their process is not well adapted to large scale preparation. Inasmuch as pure phenanthrene is now very difficult to obtain in quantity, the present process was devised for relatively large scale operation. 

Bezalel et al. (1996) reported that the white rot fungus Pleurotus ostreatus, grown in basidiomycetes rich medium, metabolized 94% of the phenanthrene added. Approximately 52% was converted to /rans-9,10-dihydroxy-9,10-dihydrophenanthrene (28%), 2,2 -diphenic acid (17%), and unidentified metabolites (17%). In addition, 3% was mineralized to carlaon dioxide. Sack et al. (1997) reported that phenanthrene was degraded by an Aspergillus niger sixain isolated from a mineral oil-contaminated soil in La Plata, Argentina. The major metabolite was identified via GC/MS as 1-methoxyphenanthrene. Two minor metabolites identified were 1- and 2-phenanthrol. 

Anthracene and phenanthrene are stereoisomers that are crystals in pure form. Anthracene is a pale yellow crystal, while phenanthrene exhibits a yellow to brown hue. Besides its common name, anthracene is referred to as anthracin, green oil, or paranaphthalene. The compound is commercially produced by recovery from the coal tar distillation fraction known as anthracene oil or green oil. Anthracene is the key ingredient in the production of anthraquinone. However, it and phenanthrene are also used for the manufacture of dyes, fibers, plastics, and wood preservatives. ° Phenanthrene, also known as phenanthrin, can be produced by high-temperature fractional distillation of coal tar oil. It is additionally used for the oxidation of diphenic acid for use in polymers, as well as the production of chemical softeners, explosives, and some pharma-ceuticals. Recent research has extended the application of both isomers to scintillation counters, semiconductors, and photoconductors. ... 

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