With polycyclic aromatics

Aitken MD, WT Stringfellow, RD Nagel, C Kazuga, S-H Chen (1998) Characteristics of phenanthrene-degrading bacteria isolated from soils contaminated with polycyclic aromatic hydrocarbons. Can J Microbiol 44 143-152. 

Andersson BE, T Henrysson (1996) Accumulation and degradation of dead-end metabolites during treratment of soil contaminated with polycyclic aromatic hydrocarbons with five strains of white-rot fungi. Appl Microbiol Biotechnol 46 647-652. 

The reactions of the tetrahalogenobenzynes with polycyclic aromatic compounds follow the expected paths. Thus with naphthalenes 54,57) cyclo-addition at the 1,4-positions occurs even with 1,4,5,8-tetramethyl-naphthalene 64>. Thus the tetrahalogenobenzynes are only able to destroy the aromaticity of one ring to form example the compound (46). 

Paschke, A., Popp, P., Schuurmann, G. (1999) Solubility and partitioning studies with polycyclic aromatic hydrocarbons using an optimized SPME procedure. Fresenius J. Anal. Chem. 363, 426 -28. 

Following an aviation kerosin spill, hydrocarbons were detected in trout stream sediments and fish up to 14 months after the spill [13]. After a fire at a weed treatment plant in 1970 a large area of mixed forested ecosystem became contaminated with polycyclic aromatic hydrocarbons and creosote [66], High polyaromatic concentrations in stream sediments adversely affected micro- and meiobenthic communities at all trophic levels. Stein et al. [67] have studied the uptake by bethnic fish (English sole, Parophrys vetulus) of benzopyrene and polychlorinated biphenyls from sediments. Accumulation of contaminants from sediments was a significant route of uptake by English sole. 

The alteration of hemoprotein(s) P-450 subpopulations in the rat may be observed spectrally, because after treatment of rats with polycyclic aromatic hydrocarbons, the Soret maximum of the carbonmonoxyferrocytochrome complex undergoes a hypsochromic shift from 450 to 448nm (50). This blue shift was not seen with rainbow trout hepatic microsomes (29,30). However, this does not preclude the induction of novel hemoproteins P-450 since (a) the induced hemoprotein(s) maty not differ spectrally from the constitutive enzymes and (b) the induced-hemoprotein may account for only a small proportion of total hemoprotein P-450, and hence its contribution to the position of the Soret maximum of carbon monoxide-treated reduced microsomes may be negligible. The latter suggestion is supported by the work of Bend et al. with the little skate. These workers have shown that hepatic microsomes from 1, 2,3,4-dibenzanthracene treated skates did not exhibit a hypsochromic shift when compared to control microsomes, however, partially purified hemoprotein exhibited an absorbance maxima at 448 nm (51). 

Roy TA, Johnson SW, Blackburn GR, et al Correlation of mutagenic and dermal carcinogenic activities of mineral oils with polycyclic aromatic content. Fundam Appl Toxicol 10(3) 466-476, 1988... 

Dewar MJS, Rogers H (1962) Pi-complexes. 2. Charge transfer spectra of pi-complexes formed by tetracyanoethylene with polycyclic aromatic hydrocarbons and with heteroaromatic boron compounds. J Am Chem Soc 84 395... 

At a former manufactured gas plant, 3 million gallons of wastewater contaminated with polycyclic aromatic hydrocarbons (PAHs) oil benzene, toluene, ethylbenzene, and xylenes (BTEX) and heavy metals were treated using an organoclay treatment train. The system consisted of an oil/water separator bag filters 9000 lb of organoclay and 6000 lb of GAC. Treatment costs were approximately 0.12/gal of treated water (D21556F, p. 12 D17268T, p. 29). 

In 1993, the Daramend process was used to treat 150 metric tons of sediment contaminated with polycyclic aromatic hydrocarbons (PAHs) from Hamilton Harbor. According to the vendor, the cost of this demonstration was approximately 26,250 or 175 per ton (D10085W, p. 15 D169839). 

Approximately 3000 yd of soil contaminated with polycyclic aromatic hydrocarbons (PAH) was treated nsing this technology at an oil refinery in Perth Amboy, New Jersey. The vendor estimated that the cost of this project was 50/yd (D213718, p. 8). 

Oxygenation of an aquifer contaminated with polycyclic aromatic hydrocarbons using membrane gas transfer modules cost approximately 2.75 per day in 1995 (D130585, p. 526). 

According to the vendor. Microbial Fence has been used to treat groundwater contaminated with polycyclic aromatic hydrocarbons (PAHs) benzene, toluene, ethylbenzene, and xylenes (BTEX) and volatile organic hydrocarbons (VOCs) at petroleum, chemical, and wood treating facilities and manufactured gas plants. Microbial Fence was used alone or in conjunction with soil venting/bioventing, aquifer aeration, pump-and-treat methods, and/or recovery of non-aqueous-phase liquids (NAPLs). 

From Table 8 it is obvious that the resolution always increases with an increase of the number of benzene rings and that riboflavine is a more powerful selector than the nucleotides, but not as good as TAPA. An interesting experiment shows that it is not always necessary to have the selector coated or bound to the solid phase but that it can sometimes be used as well, dissolved in the mobile phase. The n-dodecyl ester of N-(2,4-dinitrophenyl)-L-alanine is able to discriminate between the enantiomers of l-aza-[6]-helicene, when used as a chiral dopant in the mobile phase in HPLC on a reversed phase column 93) (see Table 9). The usefulness of this dopant must be due to the known ability of a dinitrophenyl moiety to form CT-complexes with polycyclic aromatic hydrocarbons the presence of a chiral site near this group causes resolution of helicenes, because the steric interactions in diastereomeric complexes will be quite different. 

Two types of reaction are observed for thioketones that do not have parallels in ketone photochemistry. The first is photocyclization in thioketones with polycyclic aromatic groups (4.104), where the sulfur atom forms a new bond to the aromatic system. The second is photo-oxidation by singlet oxygen to give the corresponding carbonyl compound 4.10S), possibly via a 1,2,3-dioxathietane formed as a result of initial cycloaddition. 

The coordinated induction of the two degradative operons is not a universal characteristic of the system. In Rbodococcus sp. strain B4, isolated from a soil sample contaminated with polycyclic aromatic hydrocarbons, salicylate does not induce the genes of the naphthalene-degradative pathway (Grund et al., 1992). 

TNT forms charge-transfer, or 7r, complexes with polycyclic aromatic hydrocarbons, aromatic amines, and aromatic nitro compds a number of these are listed below in Table 2. The complexes with three amines (diphenylamine, diethyl-aniline, p-anisidine) have characteristic colors this forms the basis for a rapid and convenient thin-layer chromatographic analytical procedure (Ref 34) for the identification of very small amounts of TNT. (For a discussion of the many color reactions of TNT, and of composite expls containing it, see Vol 3, C405-L ff)... 

Esteve W, Budzinski H, Villenave E (2006) Relative rate constants for the heterogeneous reactions of N02 and OH radicals with polycyclic aromatic hydrocarbons adsorbed on carbonaceous particles. Part 2 PAHs adsorbed on diesel particulate exhaust SRM 1650a. Atmos Environ 40 201-211... 

Aalbersberg and co-workers ( 7) examined the interaction of BF3 with polycyclic aromatic hydrocarbons as anthracene, perylene, and tetracene. The interaction was weak, and could be reversed... 

The point of the preceding examples is to demonstrate that a single reagent, BF3, can react in completely different ways with polycyclic aromatic hydrocarbons, graphite and certain coals. 

Mayer P, Holmstrup M. 2008. Passive dosing of soil invertebrates with polycyclic aromatic hydrocarbons limited chemical activity explains toxicity cutoff. Environ Sci Technol 42 7516-7521. 

Although this obituary is primarily concerned with Hirst s achievements in carbohydrate chemistry, it must be emphasized that the Edinburgh laboratories contained research groups active in other branches of organic chemistry. The largest of these dealt with polycyclic, aromatic hydrocarbons, and was directed by Dr. (later Professor) Neil Campbell, who, throughout the period, was an effective lieutenant in... 

Andersson, B. E., Welinder, L., Olsson, P. A., Olsson, S. Hemysson, T. (2000). Growth of inoculated white-rot fungi and their interactions with the bacterial community in soil contaminated with polycyclic aromatic hydrocarbons, as measured by phospholipid fatty acids. Bioresource Technology, 73, 29-36. 

Maliszewska-Kordybach, B. Smreczak, B. (2000). Ecotoxicological activity of soils polluted with polycyclic aromatic hydrocarbons (PAHs)-Eirect on plants. Environmental Technology, 21, 1099-110. 

Isopropyl alcohol under UV irradiation converts bromobenzene to benzene in 72% yield (Table 4). Similar replacement of bromine by hydrogen is accomplished by treatment of aryl bromides dissolved in dichloromethane with a mixture of ethanethiol and anhydrous aluminum chloride. This hard acid-soft base combination reacts with polycyclic aromatic halides and halogenated phenols by an addition-elimination mechanism, leading to an aryl ethyl sulfide through a radical anion intermediate. This is converted by another molecule of ethanethiol to the debrominated arene and diethyl disulfide. 1-Bro-monaphthalene is thus transformed into naphthalene (equation 59), 2,4,6-tribromophenol into phenol (equation 60), and bromochlorophenols into chlorophenols in 61-91% yields. ... 

According to ( erfontain 24] tetrafluorohydrazine can roiicl with polycyclic aromatic hydrocarbons in iso-octane as a solvent at 40 C. Thus aiitlujcone yielded 9,10-bisfluoroamino-9,10-dihydroanthracene. The product does not show good stability, it decomposed above I30 C with a gas evolution and at 220 C yielded mainly the parent hydrocarbon. Similarly the product of the reaction of stilbene with tetrafluorohydrazine (which was l.2-bisdinuo[oamim>-1,2-diphenylethane) decomposed above 80 ( ... 

Roos PH, Tschirbs S, Weige P, et al. Induction of cytochrome P450 1A1 in multiple organs of minipigs after oral exposure to soils contaminated with polycyclic aromatic hydrocarbons. Arch Toxicol2002 76(5-6) 326-34. 

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