Naphthalene solubility test

A) Test for Solubility. Obtain 1 g each of acetanilide, benzoic acid, and naphthalene, and test their solubility with each of the following solvents water, ethyl alcohol or methyl alcohol, and... 

There are indications that pure naphthalene (a constituent of mothballs, which are, by definition, toxic to moths) and alkylnaphthalenes are from three to 10 times more toxic to test animals than are benzene and alkylbenzenes. In addition, and because of the low water solubility of tricyclic and polycyclic (polynuclear) aromatic hydrocarbons (i.e., those aromatic hydrocarbons heavier than naphthalene), these compounds are generally present at very low concentrations in the water-soluble fraction of oil. Therefore, the results of this smdy and others conclude that the soluble aromatics of crude oil (such as benzene, toluene, ethylbenzene, xylenes, and naphthalenes) produce the majority of its toxic effects in the enviromnent. 

Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24-25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average naphthalene concentrations reported in water-soluble fractions unleaded gasoline, kerosene, and diesel fuel were 989, 644, and 167 ug/L. 

In their test system, the researchers used the ionic liquid l-butyl-3-methylimidazol-ium hexafluorophosphate (bmim)(PF6), which is stable in the presence of oxygen and water, with naphthalene as a low-volatility model solute. Spectroscopic analysis revealed quantitative recovery of the solute in the supercritical CO2 extract with no contamination from the ionic liquid. They found that CO2 is highly soluble in (bmim)(PF6) reaching a mole fraction of 0.6 at 8 MPa, yet the two phases are not completely miscible. The phase behavior of the ionic liquid-C02 system resembles that of a cross-linked polymer-solvent system (Moerkerke et al., 1998), even though... 

A simple equation for calculating the solubilities of solid substances in gaseous mixtures of a supercritical fluid with another supercritical one or an inert gas was derived. This equation involves only the solubilities of the solid in the individual constituents of the gaseous mixture and the molar volumes of the latter. The equation was tested for the solubilities of naphthalene, benzoic acid, caffeine, cholesterol, and soybean oil in gaseous mixtures containing at least one supercritical fluid. In all cases good agreement with experimental data was found. 

Testing New Mixing Rules for the Supercritical Mixture CO2 N aphthalene The mixture CO2 + naphthalene was selected to test the new mixing rules because the solubility of naphthalene in supercritical CO2 was determined in numerous papers and reliable data at several temperatures are available. The calculations were carried out at three different temperatures (308, 318, and 328 K). The critical temperatures and pressures of naphthalene and CO2 were taken from refs 24 and 25 and the values ofP and for naphthalene... 

Much less data is available for the solubilities of HOP in multicomponent aqueous solvents. The literature provides the solubilities of naphthalene and anthracene in ternary, quaternary and quinary aqueous mixed solvents. Detailed information about the experimental data used in our calculations is listed in Table 2. So far there is no method for testing the self-consistency of the experimental data regarding the solubility of a poorly soluble solid in mixed solvents and the accuracy of the data in Table 2 could not be verified. 

Properties of Naphthalene (SECTIONS 446-448).—(a) Solubility of naphthalene.—Test the solubility of naphthalene in hot and in cold water, alcohol, and ether. 

Roesijadi G, Anderson JW, Blaylock JW (1977) Uptake of hydrocarbons from marine sediments contaminated with Prudhoe Bay Crude Oil influence of feeding type of test species and availability of polycyclic aromatic hydrocarbons. J Fish Res Board Can 35 608-614 Rossi SS (1977) Bioavailability of petroleum hydrocarbons from water, sediments and detritus to the marine annelid, Neanthes arenaceodentata. Proc. 1977 oil spill conference (Prevention, behaviour, control, cleanup) Washington DC, Am Petrol Inst, pp 621-626 Rossi SS, Anderson JW (1977) Accumulation and release of fuel-oil-derived diaromatic hydrocarbons by the polychaete Neanthes arenaceodentata. Mar Biol 39 51-55 Rossi SS, Anderson JW, Ward GS (1976) Toxicity of water-soluble fractions of four test oils for the polychaetous annelids, Neanthes arenaceodentata and Capitella capitata. Environ Pollut 10 9-18 Sanborn HR, Malins DC (1977) Toxicity and metabolism of naphthalene a study with marine larval invertebrates. Proc Soc Exp Biol Med 154 151-155 Sanborn HR, Malins DC (1980) The disposition of aromatic hydrocarbons in adult spot shrimp Pandalus platyceros) and the formation of metabolites of naphthalene in adult and larval spot shrimp. Xenobiotica 10 193-200... 

Quite spectacular solubility enhancement can sometimes be obtained in this way. For example Wong and Johnston [5] obtained a hundred-fold enhancement of the solubility of cholesterol in compressed CO2 using 9% methanol as entrainer and Kumik and Reid [6] have reported an even greater effect on the solubility of hydroquinone using 2% tributyl phosphate as entrainer. They also found that the solubility of phenanthrene increased by factors of between 2 and 3 in the presence of naphthalene. Larson and King [7] found that a ten-fold increase occurred in the solubility of a typical steroid in compressed CO2 at 350 bar and 40°C when 5% methanol was added to the solvent, though an amino acid which they tested remained virtually insoluble. Kim et al. [8] found that the solubility of benzoic acid in CO2 at 35°C and 200 bar is approximately doubled when 8 wt% SO2 is added to the solvent. There are many other examples of this type. 

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