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ORGANIC CHEMISTRY I LABORATORY 220L-Tue 1-4pm

Purification of an Unknown Compound and Recrystallization

Kathleen Swanson 10/15/2013

Introduction:

Recrystallization of a compound is a very effective method by which one can purify an organic compound and strip away any impurities. Crystallization refers to the 3-dimensional structure/arrangement of molecules held together by London dispersion forces. This arrangement is ideal for purposes of purification because it allows for the compound of interest to be dissolved or melted at high temperatures, releasing the impurities that were previously trapped within its solid state and preventing the compound from fully forming a crystalline structure. Upon release of these impurities into the solvent (when dissolved in solvent or in molten state), the compound of interest is allowed to cool at a slow rate, and will form a crystalline structure, once free of the impurities that have been taken up by the solvent.

Selection of an appropriate solvent is vital to the process of purification through recrystallization. An ideal solvent must have a boiling point that is less than the melting point of the compound, the solvent should not be reactive with the compound otherwise the desired compound could be lost. The solvent should be volatile enough to be easily removed from the solution after the compound has completed recrystallization. The appropriate solvent will also either completely dissolve all of the impurities, or the impurities entirely insoluble in the solvent. Either of these will allow for their efficient removal from the pure compound. In this particular case and in consideration of the experimental design we sought a solvent that would completely dissolve the impurities so both they and the solvent could be filtrated and pulled away from the desired compound. The compound of interest should not be dissolved in the solvent at room temperature yet either dissolve or melt in the solvent at high temperatures. This allows us to keep impurities dissolved in the solvent upon cooling while the desired compound forms a solid, crystalline structure. In the event that a suitable single solvent cannot be found for a particular compound, it is then appropriate to choose a solvent pair.

Solvent pairs should be chosen carefully so that the first, primary solvent dissolves the compound completely. The second solvent should not dissolve the compound, yet both solvents must be miscible with each other (Williamson, 2011). The smalls, careful addition of a second solvent decreases the

solubility of the desired compound just slightly enough to allow for a saturated solution and for recrystallization to occur upon cooling.

This laboratory required solubility testing, to choose an appropriate solvent that met the above criteria, and served to mediate the purification of an unknown organic compound via recrystallization. Solubility tests for the unknown organic compound were conducted with the solvents Water Ethanol and Ligroin. After choosing the appropriate solvent recrystallization process was carried out using a single solvent system. At a later date, a solvent pair was used, composed of Water and Methanol, to purify the same organic compound through recrystallization. Confirmation of the unknown compound was achieved by determination of a melting point range and comparing experimental values to known melting points of organic compounds (Table 3.2, Williamson, 2001). While the first exercise required applying the knowledge of solubility testing and qualifications for selecting an appropriate solvent to carry out recrystallization, both experiments were intended to purify a solid compound leaving a pure, crystalline compound while retaining the largest possible yield of purified compound as determined by calculating a final percent yield at the experiments conclusion. Compounds used:

TABLE OF PHYSICAL PROPERTIES:


MW Compound (g/mol) Water 18.02 g/mole H2O Methanol 32.04 g/mole CH3OH Ethanol 46.405 g/mol C2H5OH 0.7915 g/mL 1.0 .790g 2.46 x Eye, skin, inhalation, ingestion risk Flammable liquid and vapor Skin/Eye irritant Extremely Flammable Ligroin 87-114 g/mol unknown 1.0 unknown Fatal if swallowed 1.0 g/mL 1.0 1g 5.55 x (g/mL) (mL) (g) Density Vol. Mass mol Hazard

0.790 g/mL at 20C

1.0

.790g

2.12 x

Benzoic acid 122.12 g/mole C6H5COOH 1.2659 g/mL .1 g 8.19 x

Irritant (skin eyes, inhalation, ingestion)

Experimental:

Experiment 1: An unknown sample was acquired, along with three potential solvents (water, ethanol, and ligroin) for the purpose of recrystallization. Solubility tests were conducted with the unknown compound with each of the three solvents seeking to find one that first previously mentioned criteria, dissolving the compound only when heat was applied, but not soluble at room temperature. Water was ultimately selected for the purification of the unknown compound

Purification was obtained by adding the minimum solvent needed to dissolve 0.1g of the unknown compound (compound was crushed to increase chances of using as little solvent as possible). Heat was applied to the solvent and compound until the solid compound was completely dissolved. The solvent was then allowed to cool at room temperature, and then further cooled by placement in an ice bath. This process allowed for the crystallization of the pure organic compound, while leaving any impurities previously trapped within the solid compound, dissolved in the solvent. Once the recrystallization process is complete, a funnel and suction filtration system was set up using an attached vacuum to separate the crystallized compound from the solvent and impurities and completely dry the compound of any remaining solvent. A cold solvent rinse is used during suction filtration to rinse the crystallized compound of any remaining solvent and/or impurities.

Experiment 2: The second purification process was conducted using a solvent pair: Water and Methanol. These two solvents were chosen based upon previously mentioned criteria. Since methanol was observed to readily dissolve the compound it was used to cover the 0.1g of unknown compound and heat was applied until the compound was completely dissolved. The second solvent was then added one drop at a time until the solution became cloudy. This appearance of cloudiness is called oiling out. This denotes

a liquid/oil state of the compound that is beginning to separate from the solution. This addition of drops of the second solvent is necessary to ensure a saturated solution necessary to bring the solution and the containing compound to the brink of recrystallization just before removing the solution from the heat source and allowing it to cool at room temperature.

The remainder of the purification process was carried out as described in Experiment 1. Once a dry, purified sample of the unknown compound was obtained from the suction filtration process, the sample was weighed to obtain a value of percent yield allowing us to evaluate the efficiency of the purification process. Also a Mel-Temp apparatus was used to determine the melting point range of the unknown compound to allow for identification.

Discussion:

The Solubility tests conducted in Experiment 1, revealed that water was the most suitable solvent as the unknown compound, later identified as Benzoic Acid was not soluble in water at room temperature, yet dissociated when heat was applied. Water fully dissolved all of the impurities contained in the initial sample also making it a perfect choice for suction filtration of the crystalline sample.

Experiment 2 utilized the same compound that was revealed to be Benzoic acid. A solvent pair of methanol and water was used in this purification process. The methanol readily dissolved the Benzoic acid when heated, and 3-4 drops of water caused the clear solution (methanol and benzoic acid (l)) became cloudy as the water was added. This addition allowed for our solution to be saturated and crystallization occurred almost immediately upon removal of the compound from the heat source. The crystallization seemed to occur at a faster rate than the first experiment using only water.

Upon completion of the filtration and drying out of the benzoic acid in crystalline (pure) form, the sample was weighed and a percent yield was calculated as follows:

This degree of recovery seemed to be a reasonable amount, demonstrating the efficiency of the methods. The melting point determination showed a range of 124C-126C identifying the
unknown compound as Benzoic acid. The samples of pure crystalline compounds were used to compare melting point range to the impure samples and a narrowing of the melting point range, 2C was observed, as well as an overall upward displacement of the range by 2.5C. In addition to the formation of crystalline solid and decreased in mass post crystallization, the narrowing of the melting point range and upward displacement of the range also confirmed that the original impure sample was in fact purified from the recrystallization procedure.

Resources

Macroscale and Microscale Organic Experiments, Williamson, K.L., 2nd Edition. D.C. Health and Company

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