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Coal Tar Dissolution in Water-Miscible Solvents: Experimental Evaluation

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Coal Tar Dissolution in Water-Miscible Solvents: Experimental Evaluation Environ. Sci. Technol. 1993, 27, 2831-2843 Coal Tar Dissolution in Water-Miscible Solvents: Experimental Evaluation Catherine A. Peters' and Richard G. Luthy Department of Civil Engineering, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213 that could be applied either in an in situ injection/recovery Coal tar, a dense nonaqueous phase liquid (NAPL), is a system or in an aboveground treatment operation. The common subsurface contaminant at sites of former man- primary objective of this work was to investigate the extent ufactured gas plants. A proposed remediation technology to which organic water-miscible solvents increase the is water-miscible solvent extraction, which requires un- solubility of coal tar and its constituent compounds. This derstanding of the effect of water-miscible solvents on the work was part of a larger project, presented in Luthy et solubility of coal tar. This study investigated this effect al. (7),aimed at investigating the feasibility of in situ and the extent to which multicomponent coal tar could be solvent extraction for remediation of coal tar contaminated represented as a pseudocomponent in thermodynamic sites. Other aspects of the project included examination modeling. The coal tar used in this study showed a of the mass transfer limitationsto insitu solvent extraction predominance of polycyclic aromatic hydrocarbons with of contaminated soils (8) and large-scale subsurface no single compound accounting for more than 4% (wt). modeling of an in situ solvent extraction process to explore The bulk solubility of coal tar in water was estimated to deployment options and estimate cleanup times (9). be 16 mg/L using composition data and Raoult's law assumption for aqueous solubility. For three solvents, The primary challenge in studying coal tar NAPLs is n-butylamine, acetone, and 2-propanol, equilibrium phase that they are mixtures of hundreds of compounds, pri- compositionsof two-phase coal tar/solvent/water mixtures marily polycyclic aromatic hydrocarbons (PAHs). It would were experimentally determined using radiolabeled ma- be an insurmountable task to completely characterize the terials and are presented as ternary phase diagrams. equilibrium-phase compositions of coal tar/solvent/water Results showed n-butylamine to be a good water-miscible mixtures by measuring and describing the partitioning of solvent for coal tar dissolution. The validity of thermo- every individual compound. The experimental data dynamic modeling of coal tar as a pseudocomponent was required to calibrate models describing phase equilibria explored by examiningthe liquid-liquid solute partitioning for a mixture increases very sharply as the number of of naphthalene, phenanthrene and pyrene and by assessing components in the mixture increases. Even for a ternary the effect of solvent extraction on coal tar phase compo- mixture, the experimental effort required is almost 1order sition. It was found that coal tar partitions as a pseu- of magnitude larger than that needed for a binary mixture docomponent in systems with appreciable solvent, but not (IO). Furthermore, of the many constituent compounds in systems with only coal tar and water. that make up coal tar, only a portion can be identified and quantified through chromatographic methods. The chal- lenge, then, is to adequately describe the dissolution Introduction behavior of a multicomponent mixture such as coal tar, which itself cannot be fully characterized, without the Today there is growing concern about nonaqueous phase burden of enormous data requirements. The approach liquids (NAPLs), a class of subsurface contaminants that used in this investigation involves a simplification, referred are immiscible in water (I). Coal tar is a NAPL that is to here as the pseudocomponent simplification, in which denser than water and often very viscous. Subsurface coal tar is treated as a single component in a system with contamination with coal tar exists today as a result of two other components: solvent and water. Coal tar uncontrolled disposal of process residuals at former solubility was explored by studying the equilibrium phase manufactured gas plant (MGP) sites. The manufactured compositions of two-phase liquid mixtures of coal tar, gas industry ended during the 1950sdue to the widespread solvent, and water for several water-misciblesolvents. The use of natural gas and the exploitation of petroleum. coal tar pseudocomponent simplification allows the com- Groundwater contaminationat MGP sites persists decades position of the two immiscibleliquid phases to be described later because of the slow, continuous dissolution of in terms of volume fractions of only three components. constituent compounds from subsurface coal tar (2-5). This simplification facilitates experimental analysis and There are as many as 1000 MGP sites in the United States data representation using ternary phase diagrams and and likely more (6). Numerous MGP site investigations makes thermodynamic modeling tractable (II), as is have verified the presence of coal tar and subsequent presented in a forthcoming paper (12). groundwater contamination, but cleanup efforts have been only sparsely applied. Conventionalremediation methods, This paper addresses four specific objectives. First, detailed composition analyses of the coal used through- such as direct coal tar pumping or groundwater pump- tar and-treat, have proven to be of limited practical use to out this project are presented. Second, the validity of the achieve low residual concentrations, as is discussed in detail pseudocomponent simplification for semi-empirical ther- elsewhere (5, 7). modynamic modeling is explored using composition anal- yses of coal tar before and after extraction and using The use of water-miscible solvents for the extraction of measurements of the partitioning behavior of three PAH coal tar from contaminated soils is a soil treatment option compounds. Third, an estimate is made of the bulk solubility of coal tar in water, which serves as a baseline * To whom correspondence should be addressed at her present address: Environmental and Water Resources Engineering, De- for comparison with experiments using solvents and partment of Civil and Environmental Engineering, The University indicates the possible extent of groundwater contamination of Michigan, Ann Arbor, Michigan 48109-2125. in terms of all constituent compounds. Finally, phase 0013-936X/93/0927-2831$04.00/0 0 1993 American Chemical Society Environ. Sci. Technol., Voi. 27, No. 13, 1993 2831 equilibria of coal tar/solvent/water systems based on nent. The premise that the composition of the dissolved experimental measurements of water and solvent parti- coal tar is similar to that of the undissolved coal tar, means tioning are presented in the form of ternary phase that diagrams. Theory Pseudocomponent Simplification. The character- where the superscripts sw and ct denote the solvent/water ization of phase equilibria of complex mixtures can be and coal tar phases, respectively. Rearranging eq 1gives accomplished in a number of ways. Petroleum products the partition coefficient, Kctlawi,the ratio of the concen- are often characterized using boiling point curves in which tration of i in the coal tar phase to the concentration in the mixture is thought of as a continuum of infinitesimal the solvent/water phase: fractions of pseudocomponents (13). Researchers studying coal tar or other mixture NAPLs have, for the most part, nct Fnct described dissolution in terms of individual compounds for all i (14-19). This approach is necessary when assessing groundwater contamination because cleanup standards Thus, an important implication is that for a given mixture are specified for individual compounds, usually those on the partition coefficients of all coal tar constituent the priority pollutant list. The individual compound compounds must be similar to each other and similar to approach was not useful for this project since the objective the overall partitioning of the coal tar pseudocomponent. was to assess the bulk solubility of coal tar based on the Semi-empirical thermodynamic modeling of ternary coal representation of the entire coal tar mixture as a pseu- tar/solvent/water systems is strictly valid only for systems docomponent. for which eq 2 is true, and the extent to which predictions For most water-miscible solvents and over a large range can be made in composition regions beyond where ex- of compositions, mixtures of coal tar, solvent, and water perimental data were used for calibration is determined will separate into two immiscible liquid phases, which are by the extent to which eq 2 is true for a wide range of referred to here as the “coal tar phase” and the “solvent/ system compositions. water phase”. The coal tar phase consists primarily of This concept was explored experimentally using the undissolved coal tar and small amounts of solvent and solvent n-butylamine, which has been identified as a good water incorporated into this organic phase. The solvent/ water-miscible solvent for coal tar dissolution (7). First, water phase consists of solvent, water, and dissolved coal solute partitioning tests were done for three coal tar tar. The coal tar pseudocomponent comprises all the constituent compounds: naphthalene, phenanthrene, and constituent compounds in coal tar, which can be thought pyrene, which represent compounds with a range of of as everything in the system except the solvent and the aqueous solubilities. Second, the effect of extraction with water.
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