Naphthalene and biphenyl

Gore et al.426 have used chloroform as a solvent for acetylation catalysed by aluminium chloride and at 45-55 °C find that a 2-methoxy substituent in naphthalene increases the reactivity of the 1 position 1.72 times, of the 6 position 3.8 times, and of the 8 position, 0.9 times the former and latter of these results indicate a considerable steric effect. Likewise, a 2-bromo substituent caused the reactivity of the 6 and 8 positions to be 0.63 and 0.58 times that of the corresponding positions in the unsubstituted compound. At 20-25 °C the relative reactivities of some polycyclics were as follows427 1-naphthyl, 1.0 3-phenanthryl 0.64 9-phenanthryl, 0.02 1-phenanthryl, 0.29 2-naphthyl, 0.28 2-phenanthryl, 0.12 4-phenanthryl, 0.0085. Some of these results seem to be due to steric hindrance, and the large difference in reactivity of naphthalene and biphenyl seems erroneous. 

Atkinson R, J Arey, B Zielinska, SM Aschmann (1987b) Kinetics and products of the gas-phase reactions of OH radicals and NjOj with naphthalene and biphenyl. Environ Sci Technol 21 1014-1022. 

A strain of Rhodococcus sp. was capable of degrading a number of chlorinated aliphatic hydrocarbons including vinyl chloride and trichloroethene, as well as the aromatic hydrocarbons benzene, naphthalene, and biphenyl (Malachowsky et al. 1994). 

Pellizari VH, S Bezborodnikov, IF Quensen, JM Tiedje (1996) Evaluation of strains isolated by growth on naphthalene and biphenyl for hybridization of genes to dioxygenase probes and polychlorinated biphenyl-degrading ability. Appl Environ Microbiol 62 2053-2058. 

The enzymes of alternative pathways may be induced in a given strain by growth with different substrates for example, growth of Pseudomonas putida R1 with salicylate induces enzymes of the extradiol fission pathway, whereas growth with benzoate induces those of the intradiol pathway (Chakrabarty 1972). As a broad generalization, the extradiol fission is preferred for the degradation of more complex compounds such as toluene, naphthalene, and biphenyl (Furukawa et al. 1983). 

Concentrations of the gaseous nitroarenes, 1- and 2-nitronaphthalene, and 3-nitrobiphenyl in these 18 samples were determined concurrently with the PAHs, in this case sampling with a Teflon-impregnated glass fiber filter (TIGF)/polyurethane foam (PUF) apparatus (Fig. 10.4). The PUF plugs quantitatively trapped the gas-phase nitroaromatics, but not naphthalene and biphenyl and several 3-ring PAHs. 

N205 with Naphthalene and Biphenyl, Environ. Sci. Technoi, 21, 1014-1022 (1987b). 

Organic compounds, aromatic solvents (benzene, toluene, nitrobenzenes, and xylene), chlorinated aromatics (PCBs, chlorobenzenes, chloronaphthalene, endrin, and toxaphene), phenols and chlorophenols (cresol, resorcinol, and nitrophe-nols), polynuclear aromatics (acenaphthene, benzopyrenes, naphthalene, and biphenyl), pesticides and herbicides (DDT, aldrin, chlordane, BHCs, heptachlor, carbofuran, atrazine, simazine, alachlor, and aldicarb), chlorinated... 

A rough prediction of desorption and recovery can be made by extrapolation from similar compounds however, until we know more about the factors involved, this practice can lead to difficulties as illustrated in Table II. The recovery of naphthalene and biphenyl from charcoal are much lower than one would predict from the recoveries of other aromatic compounds, and this stronger attraction may be related to bond angles or steric effects. The order of recovery, ortho (84%) > meta (81%) > para (76%) methyl biphenyl, supports this theory. One may predict from this information that the recovery of benzene would be very poor, which is not the case. 

Further analyses of representative extracts of each of the Amberlite resins employing GC-MS indicated the presence of significant concentrations of a variety of aromatic hydrocarbons, including alkylated derivatives of benzene, styrene, naphthalene, and biphenyl. A more comprehensive listing of these contaminants, including their approximate concentrations in the sorbent matrix, is provided in Table I. 

Amberlite XAD-2 and XAD-4 resins, for example, contain significant quantities of alkyl derivatives of benzene, styrene, naphthalene, and biphenyl as received from the supplier. PUF products, on the other hand, generally contain numerous contaminants peculiar to one of the several patented commercial manufacturing processes. These include, but are not limited to, the following classes of chemical contaminants isocyanate derivatives (e.g., toluene diisocyanates), alkyl amines, aliphatic acids, and brominated aromatics (e.g., fire retardants). 

The resulting materials were used in the separation of three organic molecules commonly studied in environmental applications of HPLC benzene, naphthalene, and biphenyl (Figure 2). Cg-APMS and Cg-MCM-48 both provide excellent separation of these molecules, with... 

Method of Wakita, Yoshlmoto, Miyamoto, and Watanabe The Wakita et al. method [46] has been derived with a set of 307 liquid compounds, including alkanes, alkenes, alkynes, halogenated alkanes, alkanols, oxoalkanes, alkanones, alkyl alkanoates, alkanethiols, alkanenitriles, nitroalkanes, and substituted benzenes, naphthalenes, and biphenyles. The model equation is... 

Woemer et al. 373) produced polyacetylene with locally oriented regions and an optical anisotropy of 2 x by polymerization on crystals of biphenyl. Yamashita and co-workers 374,375) have recently reported epitaxial polymerization of acetylene on crystals of anthracene, naphthalene and biphenyl where fibrils of cis- or trans-polymer formed, crystallographically aligned with the substrate. Fincher et al. 376) produced a 3 x extension which gave a 4 x optical anisotropy. 

Olivo, D. Parker, Oxidation of 2-methoxy-naphthalene by toluene, naphthalene and biphenyl dioxygenases structure and absolute stereochemistry of metabolites, Bioorg. Med. Chem. 1994, 2, 727-734. 

McHugh, M. Paulaitis, M. E. Solid Solubilities of Naphthalene and Biphenyl in Supercritical Carbon Dioxide. J. Chem. Eng. Data 1980, 25, 326-329. 

Comparison of the data on hydrogen exchange kinetics in naphthalene and biphenyl (Shatenshtein, 1958, 1960b) clearly shows that there is a difference in the electron mechanism of transmission of the influence of one benzene ring on another in the above two compounds (cf. Section XV, A). 

Comparison of the rate constants for hydrogen exchange in naphthalene and biphenyl with a KNH2 solution in NH3 and with HBr also shows that the first medium is very effective in suppressing differences in the reactivity of non-equivalent CH bonds in the molecule of the hydrocarbon (p. 163), while in the second medium they are clearly differentiated. 

Aminosulfonic adds of the naphthalene and biphenyl series also have been deaminated, but the smoothness of the reaction cannot be estimated from the available experimental data. 

The experimental apparatus and technique has been described in detail elsewhere.(20>21) The retention factors of naphthalene and biphenyl under isothermal conditions at various pressures were obtained using capillary columns coated with a cross-linked phenyl polymethylphenyl-slloxane stationary phase with carbon dioxide as the fluid mobile phase. A Varian 8500 syringe pump was operated under computer control providing accurate, pulsefree control of the fluid pressure. 

Solute retention as a function of pressure has been determined experimentally for a wide number of solutes over a range of temperatures and pressures.(1,23-25) The tcend in retention of a solute with pressure can be predicted within the limitations of our assumptions using eq. 11. The calculations are then compared with experimental data for the retention of naphthalene and biphenyl at various temperatures and pressures were obtained with supercritical CC. ... 

In addition to naphthalene and biphenyl, about 1 % each of biphenylene and triphenylene was found in the hydrocarbon portion of the phthalic anhydride pyrolysate. Neither was found in the benzene pyrolysis. These results indicated that phthalic anhydride gave benzyne on pyrolysis, and the benzyne subsequently reacted with benzene ... 

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