Naphthalene phenanthrene mixture

Guha, S., Peters, C. A. and Jaffe, P. R. (1999). Multisubstrate biodegradation kinetics of naphthalene, phenanthrene, and pyrene mixtures, Biotechnol. Bioeng., 65, 491-499. 

Liquid products were characterised using GC-MS. A range of aromatic compounds were identified in which the concentrations of aJkybenzenes are greater than those of alkylindans and naphthalenes while polynuclear aromatic compounds (PACs) were only minor constituents. The prominent group of constituents eluting between n-pentadecane and n-hexadecane are mixtures of alkenes, alley (benzenes and naphthalenes. Phenanthrene addition had no significant effect on the overall liquid product distribution. 

Unsubstituted Aromatics. The analyses indicated that the mixture was simplified during pyrolysis until it consisted primarily of unsubstituted aromatics such as benzene, naphthalene, phenanthrene, and pyrene. Of course, aromatization is not the only mechanism occurring since liquid products with both higher and lower molecular weights than the starting liquids, as well as gases and carbon, were formed. 

Figure 6. (a) Fluorescence spectrum of a mixture of naphthalene, phenanthrene, anthracene, perylene, ana tetracene (Xga. = 258 nm). (b) Synchronous signal (AX = 3 nm) of the same mixture. 

Schmitt (1984) verified the entrainer behavior reported by Kurnik and Reid. Schmitt and Reid (1984) show that very small amounts of an entrainer in the SCF-rich phase have very little effect on the solubility of a second component in that phase. This observation is consistent with the work of Kohn and Luks for ternary mixtures at cryogenic temperatures. The data of Kurnik and Reid have been corroborated for the naphthalene-phenanthrene-carbon dioxide system (Gopal et al., 1983). Lemert and Johnston (1989, 1990) also studied the solubility behavior of solids in pure and mixed solvents at conditions close to the upper critical end points. Johnston finds that adding a cosolvent can reduce the temperature and pressure of the UCEP while simultaneously increasing the selectivity of the solid in the SCF-rich phase. In these studies Johnston found the largest effects with a cosolvent capable of hydrogen bonding to the solute. 

Photocyanation of aromatic compounds is dealt with in several papers this year. In the presence of an electron acceptor such as p-dicyanobenzene, aromatic hydrocarbons such as naphthalene (81), substituted naphthalenes, phenanthrene, or anthracene give mixtures of products on irradiation with sodium cyanide. The major products involve substitution of hydrogen by cyanide or addition of hydrogen cyanide to the aromatic hydrocarbon. When oxygen is present, the product mixture is less complex, and a good yield of cyano-substituted compound is obtained. It is proposed that the aromatic radical cation is involved in the... 

All columns were checked by chromatography of a mixture of benzene, naphthalene, phenanthrene and anthracene with methanol-water (70 30) as the mobile phase. For Polygosil, methanol-water (60 40) had to be used to obtain separation. 

Coal tar is a complex mixture consisting almost exclusively of aromatic compounds. The main components of coal tar are naphthalene, phenanthrene, fluoranthene, pyrene, acenaphthene, anthracene, the heterocyclics carbazole, quinoline and isoquinoline, phenol and benzofuran-derivatives, as well as sulfur compounds such as thianaphthene. Olefinic compounds are also present in coal tar (Table 3.1). The total number of constituents is estimated at 10,000. 

Photochemical cyanation of aromatic hydrocarbons in acetonitrile solution is a higher yield process when the potassium cyanide complex of 18-crown-6 is the cyanide ion source [31] compared to similar reactions in mixed organic aqueous solvent systems [32] (see Eq. 7.16). A ten-fold excess of 18-crown-6/KCN over the aromatic hydrocarbon (present in 10 " M) was used. The yield improvements were attributed to increased activity of cyanide due to diminished hydration of the ion. Biphenyl, naphthalene, phenanthrene, and anthracene were photocyanated in 50%, 15%, 25% and 20% yields respectively the latter being an equimolar mixture of mono and dicyanation products [31]. 

In principle, the double photocycHzation of 1,4-distyrylbenzenes offers a convenient route to dibenz[a,h]anthracenes and [5]helicenes dependent on the sites of reaction. In the first report of the photochemistry of 1,4-phenylene bisjphenylmaleic anhydride) 27, the product was identified as the dibenz[a,h]anthracene 28," but more recently it has been shown that a mixture of isomers is formed (overall yield of 80%), in which 28 comprises less than 5%, with the (5]helicene 29 as the major product. This approach towards the synthesis of polynuclear arenas, including helicenes, is complemented by the photocyclizations of styryl-naphthalenes, -phenanthrenes, etc. and of 1,2-dipolyarylethenes. Examples of these processes pubhshed during the review period are now considered. 

Fig. 5. SolubiHty of naphthalene (squares) and phenanthrene (circles) in mixtures of toluene expanded with carbon dioxide at 25°C (B,0), in pure toluene...

The arene (5 mmol) in CHCl3 (100 ml) is added to aqueous NaOCl (0.6 M, 250 ml) and the pH is adjusted to 8-9 by the addition of cone. HCl. TBA-HS04 (0.34 g, l mmol) is added and the mixture is stirred until TLC analysis shows complete conversion of the arene. The organic phase is separated, washed well with H20, dried (K2CO ), and evaporated to yield the epoxide (e.g. 90% from phenanthrene, 76% from 1,2-benz-anthracene, 70% from acenaphthene, 19% 2,3 4,5-bis-epoxide from naphthalene). 

The formation of reactive carbenes from alkylidene Meldrum s acids has also been observed. Thus pyrolysis of 1-indanylidene Meldrum s acid at 640 °C gave the corresponding carbene which further rearranged to benzofulvene and naphthalene (Scheme 12) <1998JA8315>. Similarly, EVP of 9-fluorenylidene Meldrum s acid at 1100°C provided a mixture of phenanthrene and biphenylene <1996TL6819>. 

NFTh (21) has been effectively used for selective fluorination of polycyclic aromatics. Thus, naphthalene can be site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene.94,97 NFTh reacts with acetanilide to give a mixture of 2- and 4-fluoroacetanilide (67 33).91... 

Fig. 25. Sensitized anti-Stokes delayed fluorescence from naphthalene.60 (1, 2) Delayed fluorescence from 10 "s3/ phenanthrene, and from mixture of phenanthrene (10"W) and naphthalene (3 X 10-3M), in ethanol. (3) Normal fluorescence from solutions 1 and 2 at 260 times less sensitivity. (4) Spectral distribution of exciting light for curves 1, 2, and 3, 0.7 X IQ-8 einstein liter"1 sec.-1 absorbed. (5, 6) Normal and delayed fluorescence from 3 X 10 lM naphthalene in ethanol excited by 313 m/i, 2 X 10-4 einstein liter-1 sec.-1 absorbed. Curve (5) at a sensitivity 100 times less than curve (6). Temperature for all curves was — 72° 3°C.

Dolbier and co-workers have studied the thermolysis of the fluorinated hexa-1,3,5-triene system using l,2-bis(trifluorovinyl)naphthalene and 9,10-bis(trifluorovinyl)phenanthrene as models. These compounds form a mixture of products thermally, of which cyclopentane derivatives... 

The reactions of the higher hydrocarbons with electrophilic reagents are more complex than of naphthalene. For example, phenanthrene can be nitrated and sulfonated, and the products are mixtures of 1-, 2-, 3-, 4-, and 9-substituted phenanthrenes ... 

Figure 3. Four parameter, simplex-optimized SFC separation of a 12-component mixture. Chromatographic conditions as in Vertex 13 of Table II. Sample components isoquinoline, n-octadecane (n-CigH3g), naphthalene, quinoline, acetophenone, undecylbenzene, benzophenone, 2 -acetonaphthone, diphenylamine, o-dioctylphthalate, unidentified impurity, N-phenyl-1-naphthylamine, phenanthrene quinone. Other conditions as described in the experimental section.

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