Phenanthrene solubility

The table also shows the results of experiments with the donors and coal in phenanthrene as solvent. Consistent with the transfer of hydrogen in a radical process, those donors less reactive toward C130 than Tetralin are also less effective than Tetralin in conversion of coal to a phenanthrene-soluble product. However, in contrast to the chemistry of Step 2 we see that those donors that are more reactive toward C130 than Tetralin are also less effective in their action with coal. Thus this simple conversion scheme is suspect. 

The extract yields are shown in Table II. More than 90% of the organic coal substance was dissolved in the extraction of Ireland Mine vitrain concentrate and about 85% in the case of Bruceton coal. The yield of the phenanthrene soluble fraction was not determined in the extraction of Ireland Mine coal. In that run the products were worked up with a different procedure, and the phenanthrene soluble and phenanthrene insoluble fractions were not separated. 

Yield is given on a loss-free basis. It refers to the sum of benzene soluble, phenanthrene soluble, and phenanthrene insoluble fractions. 

C-H infrared band in the phenanthrene soluble fraction relative to the original coal and also a shift in the position of the bands.. These observations agree with the postulated mechanism. 

A common feature of solubility data for single solutes dissolved in a supercritical fluid is the existence of what has been termed crossover pressure (Chimowitz and Pennisi 1986). This is a pressure around which isotherms at various near-critical temperatures tend to converge. Figure 3 shows this behavior for phenanthrene solubility in carbon dioxide. Below the crossover pressure, an isobaric increase in temperature causes a solubility decrease, so that the solute is retrograde. 

Table I. Phenanthrene Solubility Dependence on the Aqueous Flow Rate Through a Generator Column...

Miscible solvents can significantly enhance PAH desorption and solubilization from the environment. According to Li, Cheung, and Reddy (2000), each of three cosolvents, n-butylamine, acetone, and tetrahydrofuran, increased phenanthrene solubility by more than five orders of magnitude, compared to a cosolvent-free control. Moreover, Peters and Luthy (1993) found that n-butylamine more readily solubilized coal tar into the cosolvent-water phase than did isopropyl alcohol or acetone. This indicates that cosolvents of higher molecular weight, and with few polar... 

Naphthalene, CioHs, colourless solid, m.p. 80°, insoluble in water, soluble in alcohol, characteristic odour. Anthracene, CjH4 C2H2 CjH4, m.p. 216°, white crystals when pure, with a faint blue fluorescence, but often very pale yellow crystals insoluble in water, slightly soluble in alcohol. Phenanthrene, m.p. 98°, and biphenyl, m.p. 69°, are white solids. 

Blackley548 measured the rates of deuteration of biphenylene, fluorene, tri-phenylene, and phenanthrene relative to o-xylene as 6.15 5.85 1.08 1.32, which is in very good agreement with the values of 8.80 7.00 - 1.14 which may be deduced from the detritiation data in Table 159, obtained using anhydrous trifluoroacetic acid. Aqueous trifluoroacetic acid (with the addition in some cases of benzene to assist solubility) was used by Rice550, who found that triptycene was 0.1 times as reactive per aromatic ring as o-xylene (cf. 0.13 derivable from Table 159) whereas the compound (XXXI) was 0.9 times as reactive as o-xylene. An exactly comparable measure is not available from Table 158, but dihydroanthracene (XXXII), which is similar, was 0.51 times as reactive as o-xylene and... 

The coal residue was separated into a THF-soluble fraction and a THF-insoluble residue. The wt % yields and atom % 2H compositions are given in Table I. The coal residue was 6 wt % soluble in tetrahydrofuran. The soluble fraction had 23 atom % 2H content. Evaluation of the 2H NMR data showed that 85 wt % of this fraction was derived from the coal and that its deuterium content was 10%. The chemically-bonded naphthalene-d8 content of the THF-soluble fraction, estimated from the 2H NMR data, was about 15 wt % or approximately 1 wt % of the coal. The insoluble residue had 6 atom % 2H content. This indicates that the residue contained approximately 1 wt % chemically-bonded naphthalene which was estimated from the difference in the atom % 2H content of the insoluble residue and recovered naphthalene-d8. This gives a total chemically-bonded naphthalene-d8 content of approximately 2 wt %. Similar results were obtained in extraction experiments made with phenanthrene (30), where it was found that 3-7 wt % of the phenanthrene was chemically linked to the coal product. 

Aquan-Yuen, M., Mackay, D., Shiu, W.Y. (1979) Solubility of hexane, phenanthrene, chlorobenzene, and p-dichlorobenzene in aqueous electrolyte solutions. J. Chem. Eng. Data 24, 30-34. 

Reported aqueous solubilities of phenanthrene at various temperatures 1 ... 

FIGURE 4.1.1.23.1 Logarithm of mole fraction solubility (In x) versus reciprocal temperature for phenanthrene. 

The most famous of these compounds is combretastatin A-4 (CA-4,7), isolated by Pettit et al. in 1989 [30]. Pettit s research led to the isolation and structural determination of a series of phenanthrenes, dihydrophenanthrene, stilbene, and bibenzyl compounds [31]. CA-4 (7), alongside CA-1 (8), was found to be an extremely active inhibitor of tubulin polymerization [30,32]. The major problems associated with these compounds were poor bioavailability and low aqueous solubility [33,34], and hence, research in the field was turned to designing better alternatives with the hope of eradicating the negative properties of these potent compounds. 

Environmental chemicals occur as pure liquid or solid compounds, dissolved in water or in nonaqueous liquids, volatilised in gases, dissolved in solids (absorbed) or bound to interfaces (adsorbed). Figure 5 gives a schematic view of the different physical states at which substrates are taken up by microbial cells. There is a consensus that water-dissolved chemicals are available to microbes. This is obvious for readily soluble chemicals, but there is also clear evidence for microbial uptake of the small dissolved fractions of poorly water soluble compounds. Rogoff already had shown in 1962 that bacteria take up phenanthrene from aqueous solution [55], In the intervening time many other researchers have made the same observation with various combinations of microorganisms and poorly soluble compounds [14,56,57]. 

Evaluating the effect of hydroxypropyl cyclodextrine (HPCD) on phenan-threne solubilization and biodegradation, showing HPCD significantly increased the apparent solubility (i.e., the bio availability) of phenanthrene, having a major impact on the biodegradation rate of phenanthrene [193]. 

A combined effect of natural organic matter and surfactants on the apparent solubility of polycyclic aromatic hydrocarbons (PAHs) is reported in the paper of Cho et al. (2002). Kinetic studies were conducted to compare solubilization of hydro-phobic contaminants such as naphthalene, phenanthrene, and pyrene into distilled water and aqueous solutions containing natural organic matter (NOM) and sodium dodecyl sulfate (SDS) surfactant. The results obtained after 72hr equilibration are reproduced in Fig. 8.19. The apparent solubility of the three contaminants was higher in SDS and NOM solutions than the solubility of these compounds in distilled water. When a combined SDS-NOM aqueous solution was used, the apparent solubility of naphthalene, phenanthrene, and pyrene was lower than in the NOM-aqueous solution. 

The solubility of fuel oil no. 2, particularly the alkane and isoprenoid fractions, in seawater is increased by the presence of fulvic acid, although the solubilities of phenanthrene or anthracene, both polycyclic aromatic hydrocarbons, are unaffected by the presence of humic materials (Boehm and Quinn 1973). Unfiltered Narragansett Bay water was able to dissolve 1,560 g/L of fuel oil no. 2, although removal of... 

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