Solubility of Imidazoles, Benzimidazoles, and Phenylimidazoles in Dichloromethane, 1-Chlorobutane, Toluene, and 2-Nitrotoluene

Department of Physical Chemistry, Warsaw University of Technology, Warszawa, Masovian Voivodeship, Poland
Journal of Chemical & Engineering Data (Impact Factor: 2.04). 07/2004; 49(4). DOI: 10.1021/je049907t


Solubilities of seven imidazoles (1H-imidazole, 2-methyl-1H-imidazole, benzimidazole, 2-methylbenzimi-dazole, 2-phenylimidazole, 4,5-diphenylimidazole, and 2,4,5-triphenylimidazole) in organic solvents (dichloromethane, 1-chlorobutane, toluene, and 2-nitrotoluene) have been measured using a synthetic method and liquid chromatography. The interactions of the imidazoles, benzimidazoles, or phenylimi-dazoles with different solvents are discussed. The solubilities of these imidazoles in chloroalkanes were very low. In all solvents studied, the solubility of phenylmidazoles was significantly lower than the solubility of 1H-imidazole or benzimidazoles. Experimental results of solubility were correlated by means of the Wilson, UNIQUAC, and NRTL equations utilizing parameters derived from solid-liquid equilibria results. The existence of a solid-solid first-order phase transition in the solute has been taken into consideration in the solubility calculation. The best correlation of the solubility data was obtained by the Wilson equation with the average root-mean-square deviation σ T equal to 3.2 K.

Download full-text


Available from: Aneta Pobudkowska
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Sustainable development in chemical engineering offers technical, industrially relevant solutions to environmental and economic issues. This work focuses on three specific issues; improving solvent selection and reducing costly experimentation, improving catalyst recovery while reducing reaction time, and producing commercial viable biofuels by cost effective pretreatments and valuable side product extractions. Novel solvent systems are a sustainable solution because they provide the ability to replace costly solvents with cheap, benign, and recyclable systems. Specifically, this work investigated the use of one novel solvent system, Gas Expanded Liquids (GXL).When a solvent is exposed to a gas in which it is miscible at modest pressures and temperatures, the liquid solvent becomes expanded, providing a unique tunable and reversible solvent with properties that can be much different then that of the solvent itself. If you apply this gas to a mixture of two liquids of a solid dissolved in a liquid phase, it can often provide a miscibility switch, aiding in separation, crystallization, and recovery of products or catalysts. In this work several different applications for organic solvents expanded with carbon dioxide were studied including miscibility switches for catalyst recycle, pretreatment of biomass for improved bio-ethanol production, and extraction of valuable chemicals from lignin waste in the pulp and paper industry. Solid solubility models to improve solvent selection and predict unique solvent mixtures during crystallization were also studied. The results reported here show promise for the use of GXL novel solvent systems and solid solubility models in many sustainable applications. Dr. Amyn S. Teja, Committee Member ; Dr. Wm. James Fredrick, Jr., Committee Member ; Dr. Arthur J. Ragauskas, Committee Member ; Dr. Charles L. Liotta, Committee Co-Chair ; Dr. Charles A. Eckert, Committee Chair. Thesis (Ph. D.)--Chemical and Biomolecular Engineering, Georgia Institute of Technology, 2008.
    Preview · Article ·
  • [Show abstract] [Hide abstract]
    ABSTRACT: The solubilities of erythritol in different solvents were measured using a synthetic method. The laser monitoring observation technique was used to determine the disappearance of the solid phase in a solid + liquid mixture. The effect of solvent composition and temperature on the solubility was discussed. The solubility data was correlated with an empirical equation.
    No preview · Article · May 2005 · Journal of Chemical & Engineering Data
  • [Show abstract] [Hide abstract]
    ABSTRACT: The liquid–liquid equilibria (LLE) of eight binary systems containing 1-methylimidazole and n-alkanes (n-pentane, n-hexane), cyclohydrocarbons (cyclopentane, cyclohexane), aromatic hydrocarbons (hexylbenzene) or ethers (di-n-propyl ether, di-n-butyl ether, di-n-pentyl ether) have been measured from 270K to the boiling temperature of the solvent using a “cloud point” method. Experimental solubility results are compared with values calculated by means of the NRTL equation utilizing parameters derived from LLE results.Solubility of 1-methylimidazole in many other organic solvents (aromatic hydrocarbons, branch chain ethers and ketones) has been measured at temperatures higher than 293K and no miscibility gap was observed. The interaction of 1-methylimidazole with different solvents is discussed.
    No preview · Article · Dec 2005 · Fluid Phase Equilibria
Show more