Recrystallization is a widely-used technique to purify a solid mixture. The desired product is isolated from its impurities by differences in solubility. Insoluble impurities and colored impurities can be removed from hot solvent through the use of activated carbon and filtration. Soluble impurities remain in the cold solvent after recrystallization. The desired product should be as soluble as possible in hot solvent and as insoluble as possible in cold solvent. The selection of solvent is, therefore, critical to the successful recrystallization.
Recrystallization is a purification procedure, which requires solubility of the impure solid in a heated solution and crystallization of the solid upon cooling. Clearly, this operation depends upon solute-solvent in traction involving a number of parameters including concentration, polarity of solute and solvent (like dissolves like), etc.
CHEM 2423 Preparation and Recrystallization of Acetanilide Dr. Pahlavan
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Choice of a solvent or solvent pair for recrystallization experiments generally involves preliminary tests using a small sample and various solvent systems. To determine the proper solvent or solvent system, the following steps are commonly performed.
I) The crude crystals should have low solubility in the chosen solvent at room temperature.
II) The crude crystals should have high solubility in the chosen solvent when heated to boiling.
III) The crude crystals should not react with the solvent
IV) The solvent should boil at temperature below the solid melting point.
V) The solvent should moderately be volatile so crystals dried readily.
VI) The solvent should be non-toxic, non-flammable, and inexpensive
The procedure illustrated in this experiment involve recrystallization, gravity filtration, suction filtration, melting and mixture melting points, as well as calculations of theoretical and percentage yields.
Gravity-filtration utilizes a “fluted” filter paper in the decolorizing or recrystallization step. In gravity filtration, generally the filtrate is the desired material, which is used further in the experiment.
In suction filtration, a Büchner funnel is employed to collect the desired crystals resulting from a reaction or recrystallization attempt. Be sure to “wet the filter paper” with the solvent/solid mixture to be filtered. When performing a suction filtration, it is usually advisable to install a trap between the aspirator and the suction flask. In any case always break the vacuum before turning the water off. In this operation, the filtrate or “mother liquor” may be concentrated to obtain a second crop, etc. ( or may be disposed- consult with you instructor).
This experiment involves four functional groups common in organic chemistry. The substrate (reactants) are both liquids and one of the products is solid. The reaction of aniline with acetic anhydride is a transformation in which products, acetanilide and acetic acid, are obtained. A solid product is often desirable since it may be recrystallized and a melting point determined. Solids prepared in this manner serve a derivative, whose melting point may be correlated with known values and thus is a means of identification and serves as a test for homogeneity or purity.