Indeno fluorenes

Fig. 10 Composition and spatial distribution of the main patterns of contamination identified in sediment of the Ebro River basin from year 2004 to 2006. Different temporal distribution of the PAHs pattern of contamination over the territory and constant distribution in time of the APs and heavier PAHs as well as the OCs pattern. Big circles representing higher levels of pattern contribution than small circles. Variables identification 1, naphthalene 2, acenaphtylene 3, acenapthene 4, fluorene 5, phenanthrene 6, anthracene 7, fluoranthene 8, pyrene 9, benzo(a) anthracene 10, chrysene 11, benzo(b)fluoranthene 12, benzo(k)fluoranthene 13, benzo(a)pyr-ene 14, indeno(l,2,3-cd)pyrene 15, dibenzo(a,h)anthracene 16, benzo(g,h,i)perylene 17, octyl-phenol 18, nonylphenol 19, tributylphosphate 20, a-HCH 21, HCB 22,2,4-DDE 23,4,4-DDE 24, 2,4-DDD 25, 4,4-DDD 26, 2,4-DDT 27, 4,4-DDT...

FIGURE1.15 Separation of the 16 EPA priority pollutants PAHs with ODS column using an acetonitrile water 70 30 (v/v) solution as mobile phase. Thiourea was used as standard. Detection performed at 254 nm and 30°C. PAHs 1, naphthalene 2, acenaphtylene 3, fluorene 4, acenaphthene 5, phenanthrene 6, anthracene 7, fluoranthene 8, pyrene 9, chrysene 10, benz(a)anthracene 11, benzo(fc)fluoranthene 12, benzo(l )fluoranthene 13, benzo(a)pyrene 14, dibenz(a,/i)anthracene 15, indeno(l,2,3-cd)pyrene and 16, benzo(g,/j,/)perylene). (Reprinted from Nunez, O. et al., J. Chromatogr. A, 1175, 7, 2007. Copyright 2007, with permission from Elsevier.)... 

FIGURE 19.24 HPLC separation of a standard mixture of 16 EU-priority PAHs plus EPA-priority PAHs, benzo[e]pyrene and benzo[fc]chrysene. Na=naphthalene, Ac = acenaphthylene, E=fluorene, Pa=phenan-threne, A = anthracene, El = fluoranthene, P = pyrene, BcE = benzo[c]fluoranthene, CPP = cyclopenta[c,4] pyrene, BaA = benz[a]anthracene, Ch = chrysene, 5-MeCh = 5 methylchrysene, BeP = benzo[e]pyrene, BjE = benzo[/ ]fluoranthene, BbF = benzo[h]fluoranthene, BkE = benzo[l ]fluoranthene, BaP = benzo[a]pyrene, DBahA = dibenz[a,/j]anthracene, DBalP = dibenzo[a,l]pyrene, BghiP = benzo[g,/j,i]perylene, IP = indeno [l,2,3-c4]pyrene, DBaeP = dibenzo[a,e]pyrene, BbCh = benzo[h]chrisene, DBaiP = dibenzo[a,i]pyrene,... 

Furthermore, the concentrations of the gas phase 2-and 3-ring PAHs are generally far higher than those of the 5- and 6-ring particle-phase species. Thus, as seen in Fig. 10.2, average concentrations in urban southern California air at four sites (shown in Figure 10.23) were 6000, 30, and 50 ng m-3 for gas phase naphthalene, fluorene, and phenanthrene, compared to 0.14, 0.29, and 0.77 ng m-3 for BaP, indeno[l,2,3-cz ]pyrene and benzo[g/ ]perylene, respectively in the particle phase (Fraser et al., 1998). Although the temperatures were... 

To a solution of the S-(+)-4-acethoxy-9-[2-(5-ethyl-l,2,3,6-tetrahydro-pyridin-3yl)-l-(lH-indol-2-yl)-l-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,ll,12,12b-octahydro-lH-6,12a-diaza-indeno[7,l-ca]fluorene-5-carboxylic acid methyl ester in dioxane and glacial acetic acid was added 37% aqueous formaldehyde and the mixture stirred at 35°C for 24 h. The solution was evaporated in vacuo and the residue suspended in chloroform and washed with cold aqueous 5% K2C03 solution. The chloroform layer was dried (MgS04), filtered, and evaporated. The residue was chromatographed eluting with EtOAc/MeOH, 10% NH4OH to give the product navelbine. 

Fig. 10.1. Separation of polycyclic aromatic hydrocarbons (PAHs) on columns packed with Spherisorb ODS particles. Conditions (A) 35(43) cm x 50 pm i.d. fused silica capillary column packed with 3 pm Spherisorb ODS-1 particles (B) 41(53) cm x 75 pm i.d. fused-silica capillary column packed with 5 pm Spherisorb ODS-1 particles 30 kV applied voltage 5 kV, 5 s electrokinetic injection acetonitrile-50 mM Tris buffer, pH 8.1 (80 20 v/v). Peak identifications 1, benzene 2, naphthalene 3, acenaphthylene 4, fluorene 5, acenaphthene 6, phenanthrene 7, anthracene 8, fluoranthene 9, pyrene 10, benz[n]anthracene 11, chrysene 12, benzo[6]fluoranthene 13, benzo[fc]fluoranthene 14, benzo[a]pyrene 15, dibenz[n,/i]anthracene 16, indeno[7,2,3-af]pyrene 17,...

Soil PAH 14 (fluorene to indeno [1,2A-Qc/ pyrene) ug/kg dry wt 3940 2180 695 Rouen, Honfleur, Forest of Brotonne Motelay-Massei ef a/. 2004 ... 

Figure 11.3 Chromatogram of 16 PAH standards using gradient elution (50% aqueous acetonitrile to 100% acetonitrile). 1, Naphthalene 2, Acenaphthene 3, Fluorene 4, Phenan-threne 5, Anthracene 6, Fluoranthene 7, Pyrene 8, Benz(a]anthracene 9, Chrysene 10, Benzo[ ]pyrene 11, Benzo(6]fluoranthene 12, Benzo[A ]fluoranthene 13, Benzo( Jpyrene 14, Dibenz[a,A]anthracene 15, Benzo[g/ii]perylene 16, Indeno(123cd)pyrene 17, Perylene.

Fig. 7.20. Extraction efficiency achieved in the SFE of PAHs from fly ash. (A) By adding various binary modifiers to CO, [bars represent the following combinations from left to right trifluoroacetic acid (TFA) in toluene, triethylamine (TEA) in toluene, isopropylamine in toluene, pure toluene, tetra-butylammonium hydroxide in methanolt-toluene, citric acid in a methanol-toluene mixture and the absence of modifier]. (B) By successive application of a liquid modifier (four times) compared to Soxhiet extraction (shaded, left bars) and conventional SFE with CO,/pure toluene (right bars) CO,/TEA in toluene (-0-) and CO,/TFA in toluene (-A-). Fluo fluorene, phen phenanthrene, Anth anthracene, F fluoranthene, Py pyrene, B(a)A benz(a)anthracene, Chry chrysene, B(b)F benzo(b)flu-oranthene, B(k)F benzo(k)fluoranthene, B(a)P benzo(a)pyrene, D(ah)A dibenz(a,h)anthracene, B(ghi)P benzo(g,h,i)-perylene, I(cd)P indeno(l,2,3-c,d)pyrene. (Reproduced with permission of Springer-Verlag.)...

Fig. 1 Gas chromatography-flame ionization detection chromatogram of a complex mixture of PAHs extracted by SFE from a contaminated soil. (1) naphthalene (2) 2-methylnaphthalene (3) 1-methylnaphthalene (4) acenaphthene (5) fluorene (6) dibenzothiophene (7) phenanthrene (8) anthracene (9) fluoranthene (10) pyrene (11) benzo(a)anthracene (12) chrysene (13) benzo(e)pyrene (14) benzo(a)pyrene (15) indeno(l,2,3-cd)pyrene (16) dibenzo(a,h)anthracene (17) benzo(g,h,i)perylene. (From Ref. [12].)...

Pyka separated 16 PAHs (naphthalene, acenaphthylene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo [a] anthracene, chrysene, benzo[/>]fluoranthene, benzo[fe]fluoranthene, benzo[a]py-rene, dibenzo[a,/z]anthracene, benzo[g,/i,i]perylene, and indeno[l,2,3-C(i]pyrene) according to the Environmental Protection Agency (EPA) by gradient HPLC on a LiChrospher PAH column using acetonitrile and water as mobile phases. Retention times fr (sec) of investigated PAHs were correlated with topological indices based on the adjacency matrix (M, 012) and the... 

Other related metallations by n-BuLi include those of 7bH-indeno[l,2,3jk]fluorene , 4,ll-dihydrodicyclopenta[def,pqr]tetraphenylene and syn- or anti-[2.2](2,7)fluorene-phane . ... 

In analogy to fluorene the more acidic 5H-indeno(l,2-b)pyridine (= 4-azafluorene) (133) smoothly condenses with (7i) to (134) which cyclize uniformly to 6-phenyl-acenaphtho(l,2-b)pyridine (= 2-phenyl-7-azafluoranthene) (75J)44 ... 

PAHs1 NA 0.6 mg/kg/day (intermediate, acenaphthene) 0.4 mg/kg/day (intermediate, fluoranthene fluorene) 10 mg/kg/day (intermediate, anthracene) Group 2A benz(a)anthracene, benzo(a)pyrene Group 2B benzo(b)fluoranthen e benzo(j)fluoranthene, ideno(1,2,3-c,d) pyrene Group 3 anthracene, benzo(g,h,i)perylene, additional PAHs Group B2 benz(a)anthracene, benzo(b)fluoranthene, benzo(a)pyrene, chrysene, dibenz(a,h)- anthracene, indeno(1,2,3-c,d)- pyrene Group D acenaphthylene, anthracene, fluoranthene... 

In some cases the indazole and spiroindazole route did not lead to isolable cycloproparenes. Thus, the attempted synthesis of a 1,1-diphenylbenzocyclopropene or 1-phenylbenzocyclo-propene-l-carbonitrile by this route resulted instead in isolation of fluorene derivatives. The photolysis or pyrolysis of spiro[fluorene-9,3 -3//-indazole] gave fluoradene (4b//-indeno-[l,2,3-y, ]fluorene) as the major product (80%). The cycloproparene, spiro[17/-bcnzocyclo-propene-l,9 -fluorene], although formed as a reaction intermediate, was not isolable. Similarly, the thermolysis and photolysis of 9,10-dihydrospiro[anthracene-9,3 -3 /f-indazole]-10-one gave spirocycloproparenes as (non-isolable) reactive intermediates. ... 

From what is currently known about benzo[a]pyrene. the federal government has developed regulatory standards and guidelines to protect people from the potential health effects of PAHs in drinking water. EPA has provided estimates of levels of total cancer-causing PAHs in lakes and streams associated with a risk of human cancer development. If the following amounts of individual PAHs are released to the environment within a 24-hour period, EPA must be notified 1 pound of benzo[b]fluoranthene, benzo[a]pyrene, or dibenz[a.h]anthracene 10 pounds of benz[a]anthracene 100 pounds of acenaphthene, chrysene, fluoranthene, or indeno[1,2,3-c,d]pyrene or 5,000 pounds of acenaphthylene, anthracene, benzo[k]fluoranthene, benzo[g,h,i]perylene, fluorene, phenanthrene, or pyrene. 

Complete Carcinogenesis Studies. Studies in laboratory animals have demonstrated the ability of benz[a]anthracene, benzo[b]fluoranthene, benzo[j]fluoranthene, benzo[a]pyrene, chrysene, dibenz[a,h,]anthracene, and indeno[1,2,3-c,d]pyrene to induce skin tumors (i.e., they are complete carcinogens) following intermediate dermal exposure. Anthracene, fluoranthene, fluorene, phenanthrene, and pyrene do not act as complete carcinogens. The data supporting these conclusions are discussed below by chemical. Only those studies considered adequate and reliable with respect to study design and adequacy of reporting are presented in Table 2-3. 

Interactions between selected noncarcinogenic PAHs and carcinogenic benzo[a]pyrene have also been documented to reduce the carcinogenic potential of benzo[a]pyrene in animals. Benzo[a]fluoranthene, benzo[k]fluoranthene, chrysene, perylene, and a mixture of anthracene, phenanthracene, and pyrene significantly inhibited benzo[a]pyrene-induced injection-site sarcomas. However, other PAHs including anthracene, benzo[g,h,i]perylene, fluorene, and indeno[1,2,3-c,d]pyrene had no antagonistic effects (Falk et al. 1964). Coexposure of tracheal explants to benzo[e]pyrene and benzo[a]pyrene resulted in an increased incidence of tracheal epithelial sarcomas over that seen with either PAH alone (Topping et al. 1981). Phenanthrene administration with benzo[a]pyrene decreased the DNA adduct formation in mice (Rice et al. 1984). 

PAHs may also volatilize from soil. Volatilization of acenaphthene, acenaphthylene, anthracene, fluorene, and phenanthrene (low molecular weight PAHs) from soil may be substantial (Coover and Sims 1987 Southworth 1979 Wild and Jones 1993). However, of 14 PAHs studied in two soils, volatilization was found to account for about 20% of the loss of 1 -methyinaphthalene and 30% of the loss of naphthalene volatilization was not an important loss mechanism for anthracene, phenanthrene, fluoranthene, pyrene, chrysene, benz[a]anthracene, benzo[b]fluoranthene, dibenz[a,h]anthracene, benzo[a]pyrene, and indeno[1,2,3-c,d]pyrene (Park et al. 1990). 

PAHs have been detected in surface waters of the United States. In an assessment of STORET data covering the period 1980-82, Staples et al. (1985) reported median concentrations in ambient water of >10 ug/L for 15 PAHs (acenaphthene, acenaphthylene, anthracene, benz[a]anthracene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[g,h,i]perylene, benzo[a]pyrene, chrysene, fluoranthene, fluorene, indeno[1,2,3-c,d]pyrene, naphthalene, phenanthrene, and pyrene). The number of samples ranged from 630 (naphthalene) to 926 (fluoranthene) the percentage of samples in which these PAHs were detected ranged from 1.0 (benzo[g,h,i]perylene) to 5.0 (phenanthrene) and 7.0 (naphthalene). 

Figure 7.4 Results obtained for the Soxhlet extraction of various polycyclic aromatic hydrocarbons from contaminated soil 1, naphthalene 2, acenaphthylene 3, acenaphthene 4, fluorene 5, phenanthene 6, anthracene 7, fluoranthene 8, pyrene 9, benz[a]anthracene 10, chrysene 11, benzo[fc, ]fluoranthene 12, benzo[a]pyrene 13, indeno[l,2,3-a/]pyrene 14, benzo[g/z/]pyrene [1] (cf. DQ 7.2).

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