Polyaromatic hydrocarbons anthracenes

K. Hosoya, Y. Iwakoshi, K. Yoshizako, K. Kimata, N. Tanaka, H. Takehira and J. Haginaka, An unexpected molecular imprinting effect for a polyaromatic hydrocarbon, anthracene, using uniform size ethylene dimethacrylate particles, HRC, J. High Resolut. Chromatogr., 22 (5) 256-260, 1999. 

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

Figure 5.12 Polyaromatic hydrocarbon species (1) phenanthrene, (2) anthracene, (3) pyrene, (4) benz[o]anthracene, (5) chrysene, (6) naphthacene, (7) benzo[c]phenanthrene, (8) benzo[ghi] fluoranthene, (9) dibenzo[c,g]phenanthrene, (10) benzo[g/ ]perylene, (11) triphenylene, (12) o-terphenyl, (13) m-terphenyl, (14) p-terphenyl, (15) benzo[o]pyrene, (16) tetrabenzonaphthalene, (17) phenanthro[3,4-c]phenanthrene, (18) coronene...

Polyaromatic hydrocarbons Synthetic 10"5-10"7 mol L"1 (anthracene, rubrene, pyrene)... 

Fowlie and Bulman [43] have carried out a detailed study of the extraction of anthracene and benzo[tf]pyrene from soil. They carried out a replicated [24] factorial experiment using Soxhlet extraction and Polytron techniques. Soxhlet extraction followed by thin layer chromatography gave higher recoveries of the two polyaromatic hydrocarbons. 

In this study the soil samples were spiked with labelled and unlabelled benzo[<2]pyrene, or anthracene at 5 and 50pg/g soil. The samples were incubated in biometer flasks at 20°C for three and five months for anthracene and benzo[a]pyrene, respectively, allowing degradation to be monitored and the polyaromatic hydrocarbon to interact with the soil matrix. 

The polyaromatic hydrocarbons in the soil sample were quantitated by using an external standard of anthracene. The results reportedly for a polluted soil and sediment sample indicate that this flash evaporation-pyrolysis technique combined with gas chromatography-mass spectrometry is a valuable tool for rapidly screening polluted samples for virtually all types of anthropogenic contaminants except for heavy metals. 

Anthracene is a three-ring polyaromatic hydrocarbon (PAH) with the following structure. 

Polyaromatic hydrocarbons (benzene, toluene, naphthalene, acenaphthylene, fluor-ene, anthracene, 1,2-benzanthracene, phenol, acetone) ODS Hypersil, 5 pm Gradient acetonitrile-water (from 60 40 to 90 10) 500 mm x 75 pm i.d. 200 mm packed length, flow-injection analysis... 

Polyaromatic hydrocarbons Nucleosil ODS, 5 pm (naphthalene, fluorene, phenanthrene, anthracene), acetone... 

Polyaromatic hydrocarbons (naphthalene, fluorene, phen-anthrene, pyrene, benz[a]anthracene Linear polymer coated capillary [poly(N-tert.-butyl acrylamide-co-2-acrylamido-2-methyl-1 -propanesulfonic acid] Acetonitrile-50 mA/Tris buffer, pH 7.3 (30 70) 600 mm x 25 pm i.d. 450 mm effective column length 11... 

Fig. 4.45. Luminescent sensor for polyaromatic hydrocarbons (e.g. anthracene) based on a derivatised Tb(III)-DOTA complex. Redrawn from D. Parker et al., J. Chem. Soc., Perkin Trans. 2,1329, 2000.

There are many examples of molecules in which benzene rings are forced out of planarity, including 7-circulene (40), ° 9,8-diphenyltetrabenz[fl,c,/i,7 ]anthracene (41), and 42 (see also p. 230). These have been called tormented aromatic systems. The record for twisting an aromatic 7i-electron system appears to be 9,10,11,12,13,14,15,16-octaphenyldibenzo[fl,c]naphthacene (43), which has an end-to-end twist of 105°. This is >1.5 times as great as that observed in any previous polyaromatic hydrocarbon. 

Like many organic compounds, excessive acute exposure to dibenz[d, /i]anthracene can lead to dizziness, nausea, and general central nervous system disturbances that resemble intoxication. Previous exposure to polyaromatic hydrocarbons or genetic predisposition can increase the MFO system that activates dibenz[d, /i]anthracene to the reactive epoxide. In addition, personal habits such as smoking can significantly increase a person s exposure to these compounds. 

Dibenz[a,h]anthracene is classified as a probable human carcinogen and therefore chronically may produce cancer. In addition, carcinogenic polyaromatic hydrocarbons have been implicated in immunosuppressive activity. 

A valuable goal appears to be the anodic conversion of substituted toluenes into the corresponding aldehydes. The reaction can be achieved either in methanol [194] (intermediate formation of a ketal) or in aqueous solution in an indirect manner (presence of Mm11 or/and Cem ions as mediators [195]). The indirect oxidation of polyaromatic hydrocarbons (naphthalene, anthracene) into the corresponding quinones could be achieved in the presence of electrogenerated ceric ions. 

Fig. 4.4.10. Separation of a polyaromatic hydrocarbon mixture on 5 different brands of chemically bonded ODS-silica, the carbon content of the individual materials are given in brackets, a, HC-ODS (8.5%) b, LiChrosorb RP-18 (19.8%) c, Partisil-10 ODS-2 (16%) d, Zorbax ODS (10%) e, pBondapak C,g (10%). Peaks 4, benz[a]anthracene 5, chrysene 6, benzo[e]pyrene 7, benzo b]fluoroanthrene 8, benzo k]fIuoroanthrene 11, benzo[ghi]perylene 12, indeno[l,2,3-c,d]pyrene. Reprinted from Ref. 14 with permission.

In the search for sorbents that effectively remove polyaromatic hydrocarbons (PAH), ranging from two to four condensed rings, from aqueous solutions, Valderrama et al. [83, 84] studied the kinetics of sorption for naphthalene, fluorene, anthracene, acenaphthene, pyrene, and fluoranthene onto MN-200 and a granulated activated carbon. The better kinetic properties of MN-200 are transduced in lower hydrauhc residence time and consequently in lower barrier thickness. A simulation of the barrier thickness to... 

In this study, a spectrographic analysis of the by-products of the decomposition of methane revealed the presence of large amounts of acetylene, ethylene, and benzene, plus a variety of compounds consisting mostly of the polyaromatic hydrocarbons (PAH) such as naphthalene, anthracene, phenantrene, acenaphthylene, pyrene, and fluoranthene, in addition to the deposited pyrolytic graphite. Some of these compounds form the soot and tar-like deposits which are often observed on the wall of CVD reactors during carbon deposition. 

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