Name: purifying crystals by solubility
Uploaded: 2020-03-26T07:22:27.000Z
Duration: 3 min 12 s
Channel: JoVE

Most products contain impurities. One way to purify these products is by recrystallization. Recrystallization begins with dissolving the impure product in just enough hot solvent to form a saturated solution, where as much solute is dissolved in the solvent as possible. Any additional solute will not seem to dissolve.
A hot solvent is used because solubility typically increases with temperature. As temperature increases, the amount of solute that can be dissolved in the solvent increases. As the solution cools, the solubility of the product decreases, and solute molecules come together to form small stable crystals called nuclei.
This is the first step of crystallization, called nucleation. Additional crystal growth happens on the nuclei because solute molecules have a greater affinity for joining existing solute crystals than forming new crystals. Soluble impurities are left in solution.
Crystallization can happen spontaneously or can be encouraged by scratching the inside of the flask, agitating the solution, or adding a seed crystal of the compound, all of which provide a surface for further growth.
Recrystallization into large, pure, regularly shaped crystals only works when an appropriate solvent is used. The compound should be insoluble in the solvent at room temperature and soluble at high temperatures. Ideally, the impurities should be either insoluble in the solvent at high temperature or soluble in the solvent at room temperature.
If the impurities are insoluble in hot solvent, they are filtered out before crystallization. After recrystallization, the crystals are filtered out and washed with cold solvent to remove impurities from the surfaces. Now, the purity of the crystals can be analyzed.
When choosing a solvent, keep in mind that the greater the difference in solubility between high temperatures and low temperatures, the more likely the solute will come out of solution as it cools to form crystals. The rate of cooling is also important in recrystallization.
Rapid cooling favors the formation of many nucleation sites and the growth of smaller crystals, whereas cooling slowly induces the formation of fewer nucleation sites and the growth of fewer, larger but purer crystals. So, slower cooling is preferred.
In this lab, you will recrystallize two impure organic compounds, acetanilide and trans-cinnamic acid, and then assess the purity of the recovered compounds by comparing their melting point range to values in the literature.

recrystallization

Recrystallization
Often, the desired product of a chemical reaction is part of a more complex reaction mixture, which can be composed of the solvent, starting materials, and impurities. Learning how to purify organic compounds properly is a valuable technique in organic chemistry. Recrystallization harnesses the differences in solubility of the desired compound and the impurity in the solvent to purify the desired product as a solid. There are three standard methods of purification: distillation, extraction, and recrystallization.
Solubility
The solubility of a substance is the maximum amount that dissolves in a fixed volume of a given solvent at a given temperature. Different solutes have different solubilities and dissolve in different solvents. Solutes may have defining characteristics that lend themselves to be exploited for recrystallization. Compounds exhibit one of the following behaviors in a solvent. First, the compound can be insoluble or have very low solubility in the solvent at all temperatures. Second, the compound can be soluble in the solvent at higher temperatures. Third, the compound can be soluble in the solvent at all temperatures.
A major factor in determining whether a solute dissolves in a solvent and forms a solution is the strength and type of intermolecular forces between the solute and solvent. The general rule of thumb is &#8220;like dissolves like,&#8221; meaning that substances with similar types of intermolecular forces dissolve in each other. For example, polar substances such as table salt (NaCl), dissolve well in polar water.
Another key factor that improves solubility is temperature. For many substances, solubility greatly increases at higher temperatures. This is due to the fact that the increased kinetic energy at higher temperatures breaks the solute intermolecular forces that keep molecules together. This is seen in everyday life. For example, we know that table salt (NaCl) dissolves well in water; however, more dissolves at higher temperatures than at lower temperatures.
Qualitatively, a solution is considered unsaturated if the maximum amount of dissolved solute has not yet been reached. When the maximum possible solute has dissolved, the solution is saturated. A supersaturated solution contains more dissolved solute than the maximum possible amount under typical conditions.
<h4>Recrystallization </h4>
Recrystallization takes advantage of the differences in solubility between the desired product and the contaminants at high temperatures. The first step of recrystallization is to dissolve the product mixture in a minimal volume of heated solvent that still results in a saturated &#8212; but not supersaturated &#8212; solution. Then, the solution is cooled to room temperature, decreasing the solubility of both the desired compound and the impurity.
As the solution cools, crystallization of the pure component begins, while the still soluble impurities do not. This occurs when the component of interest is in a significantly higher concentration than the impurity. First, in the nucleation phase, the solvent initiates the random agglomeration of the solute molecules, forming the first crystal called a seed or nucleus. Next, in the particle growth or crystallization phase, more molecules are added to the seed, forming a crystal. The crystal contains the pure compound, while the impurity remains in the solvent.
Nucleation proceeds faster than particle growth in a supersaturated solution. With more seeds, each crystal is smaller. Thus, if the solution is saturated, rather than supersaturated, fewer seeds form, resulting in larger crystals. Heating the solution to a higher temperature before cooling to room temperature enables the dissolution of a higher concentration of solute, decreasing supersaturation. Additionally, rapid cooling results in quick nucleation, forming many small crystals and trapping the impurity inside of the crystals. Slow cooling is preferred to achieve fewer, larger crystals.
Once the solution has cooled to room temperature, and the crystals have formed, the solution is filtered using vacuum filtration. Then, the crystals are allowed to dry. The percent recovery is calculated by dividing the mass of the recovered product by the mass of the crude product.
<img src="/CDNSource/lm/labs/58/58_Concepts_1.jpg" alt="Percent recovery formula; equation for calculating efficiency in chemical yield processes." data-altupdatedat="1761830439000" />
The recovery is rarely 100%, as the solubility of the compound at low temperatures governs how much of the compound is crystallized.
<h4>Selecting a Solvent</h4>
For crystallization to be effective, the optimal solvent must be used. The desired product should have low solubility in the selected solvent at room temperature but high solubility in the solvent at a higher temperature. Ideally, the impurities should be soluble in the solvent at all temperatures. Thus, when the mixture is added to the solvent at a high temperature, the desired product and impurities dissolve readily.
As the solution is cooled, the solubility of the desired product decreases and crystallization begins to occur, forming purified product. Occasionally, impurities may remain insoluble in the solvent of choice, even at high temperatures. Hot gravity filtration of the solution that contains dissolved product can remove the solid impurities. The product can then be recrystallized by cooling the sample.
Ideally, the solvent to be used should be able to boil at a temperature well below the melting point of the desired product. The solvent should also be inert and not react with the desired purified product.
<h4>References</h4>
<ol>
	<li style="font-size:17px">Kotz, J.C., Treichel Jr, P.M., Townsend, J.R. (2012). Chemistry and Chemical Reactivity. Belmont, CA: Brooks/Cole, Cengage Learning.</li>
	<li style="font-size:17px">Silberberg, M.S. (2009) Chemistry: The Molecular Nature of Matter and Change. Boston, MA: McGraw Hill.</li>
	<li style="font-size:17px">Harris, D.C. (2015). Quantitative Chemical Analysis. New York, NY: W.H. Freeman and Company.</li>
</ol>

Recrystallization

Recrystallization
Often, the desired product of a chemical reaction is part of a more complex reaction mixture, which can be composed of the solvent, ...

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purifying crystals by solubility

Purifying crystals by solubility is a key organic chemistry technique. Recrystallization uses differences in solubility to separate a desired solid product from starting materials, solvent, and impurities. It is one of the three standard purification methods, along with distillation and extraction.

Solubility is the maximum amount of a substance that can dissolve in a fixed volume of solvent at a given temperature. Different solutes dissolve in different solvents, and their behavior can vary widely. A compound may stay insoluble or only slightly soluble at all temperatures, it may dissolve better at high temperature, or it may remain soluble at all temperatures. The main reason is the strength and type of intermolecular forces between the solute and the solvent. The rule “like dissolves like” applies here, so substances with similar intermolecular forces tend to dissolve in each other. For example, polar table salt (NaCl) dissolves well in polar water. Temperature also matters. In many cases, solubility rises as temperature rises because added kinetic energy helps break the forces holding solute molecules together. A solution is unsaturated when more solute can still dissolve. It is saturated when it has reached the maximum amount. A supersaturated solution contains more dissolved solute than expected under normal conditions.

Recrystallization uses those solubility differences at high temperature and low temperature. The crude product is first dissolved in a minimal volume of heated solvent. The goal is a saturated solution, but not a supersaturated one. The solution is then cooled to room temperature. As it cools, the solubility of both the desired compound and the impurity drops. The pure compound begins to crystallize first, while impurities that are still soluble remain in the liquid. This works best when the compound of interest is present at a much higher concentration than the impurity.

Crystal formation happens in two stages. In nucleation, the solvent helps solute molecules gather into the first tiny crystal, called a seed or nucleus. In particle growth, more molecules attach to that seed and the crystal gets larger. The crystal contains the pure compound, while the impurity stays in the solvent. In a supersaturated solution, nucleation happens faster than particle growth, so more seeds form and the crystals stay small. If the solution is only saturated, fewer seeds form and the crystals become larger. Heating the solution more before cooling can reduce supersaturation by dissolving a higher concentration of solute. Slow cooling is also preferred because rapid cooling makes many small crystals and can trap impurity inside them.

After the crystals form, the solution is filtered by vacuum filtration and the crystals are allowed to dry. The percent recovery is found by dividing the mass of the recovered product by the mass of the crude product. Recovery is rarely 100% because the compound’s low-temperature solubility limits how much can crystallize. Choosing the right solvent is important for successful crystallization. The desired product should be poorly soluble at room temperature but highly soluble when hot. Ideally, impurities stay soluble at all temperatures, so they remain in solution as the product crystallizes. If some impurities do not dissolve even when hot, hot gravity filtration can remove them before the sample is cooled again. The solvent should also boil well below the melting point of the desired product and should not react with it.

Purifying Crystals by Solubility

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Purifying Crystals by Solubility

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