Name: separating mixtures with solvent extraction
Uploaded: 2020-03-26T07:22:28.000Z
Duration: 2 min 55 s
Channel: JoVE

Extraction is a technique to separate components from a mixture. You are already familiar with extraction. Any time you steep tea, you&#39;re extracting water-soluble compounds, like caffeine and flavors, from the tea leaves into your hot water. This is an example of a solid-liquid extraction.
Liquid-liquid extraction is another type of extraction where the mixture is dissolved in two immiscible liquid phases. The solvents must be immiscible, meaning they do not mix and are separate phases. Liquid-liquid extractions are performed in a separatory funnel so that the more dense solvent will settle to the bottom and the less dense solvent will sit on top. Then, each solute compound will transfer to the phase in which it is most soluble. Therefore, it is important to choose solvents with different polarities.
In general, non-polar solutes will partition into the organic phase, and polar solutes will partition into the aqueous phase. The partition coefficient, K, is the ratio of solute concentration in the organic phase to that in the aqueous phase. Once the solutes have separated, the two different phases are collected. Keep in mind that it is likely that there will be residue of each component in both phases.
An acid-base extraction is a special type of liquid-liquid extraction that separates acidic and basic compounds based on the solubility differences. Recall that an acid is a compound that donates a proton when dissolved in water, and a base is a compound that accepts a proton.
To separate acidic compounds, a base is added to the mixture. The base will accept a proton from the acidic compound, making it ionic. Conversely, adding an acid would transfer a proton to a basic compound. In both instances, the ionic compound will transfer to the aqueous phase, and the neutral compounds will partition to the organic phase. The ionic compound is collected and then either deprotonated or reprotonated to convert it back to its original compound.
In this lab, you will separate a mixture of cellulose, benzoic acid, and caffeine. First, you will use extraction and filtration to isolate cellulose. Then, you will perform an acid-base extraction to separate benzoic acid and caffeine.

extraction

Extraction
Extraction is a common technique used in organic chemistry to isolate a target compound. In the extraction process, a solute is transferred from one phase to another to separate it from unreacted starting materials or impurities. Extraction is also used to facilitate the isolation of a solute from a reaction solvent that is difficult to remove by evaporation, such as a solvent with a high boiling point.<span style="color: rgb(0, 0, 0); font-family: Roboto, RobotoDraft, Helvetica, Arial, sans-serif; font-size: 13px; font-style: normal; font-variant-ligatures: normal; font-variant-caps: normal; font-weight: 400; letter-spacing: normal; orphans: 2; text-align: start; text-indent: 0px; text-transform: none; white-space: pre-wrap; widows: 2; word-spacing: 0px; -webkit-text-stroke-width: 0px; background-color: rgb(255, 255, 255); text-decoration-style: initial; text-decoration-color: initial; display: inline !important; float: none;"> Generally, there are three types of extractions. First, in solid-liquid extraction, the solute is transferred from a solid phase to a liquid phase. In liquid-liquid extraction, a solute is transferred from one liquid to another. In acid-base extraction, a solute is transformed into an ionic compound and transferred from an organic phase to an aqueous phase. A common example of extraction is the brewing coffee or tea. The solid phase, which contains the caffeine, plant flavors, and odors, is extracted by the hot water into the liquid phase.
Liquid-Liquid Extraction
A liquid-liquid extraction either transfers an organic compound that is dissolved in an aqueous phase to an organic solvent, or it is used to transfer unreacted reactants, salts, and other water-soluble impurities to the aqueous phase while leaving the organic compound of interest in the organic phase. Immiscible liquids are liquids that never form a homogenous solution, even when thoroughly mixed. Instead, immiscible liquids separate into different phases, like oil and water.
A liquid-liquid extraction transfers an organic compound that is dissolved in an aqueous phase to an organic solvent. To perform a liquid-liquid extraction, first, the aqueous solution containing the solute is added to a separatory funnel. Then, a non-water-soluble organic solvent is added to the separatory funnel. When the contents of the funnel are mixed well, the organic compound partitions into the organic phase based on its higher solubility in the organic phase than the aqueous phase.
Since the two solvents are immiscible, the two liquids form discrete layers, with the dense liquid on the bottom and the less dense liquid on the top. Once the two phases settle back into two layers, they are separated by opening the stopcock at the bottom of the separatory funnel and allowing one layer to flow out. The liquid that had the solute removed is called the raffinate, while the liquid that gained the solute is called the extract.
The organic compound is partitioned between the two layers based on its solubility in each phase. Equilibrium is reached when the chemical potential of the solute is the same in the two phases. The partition coefficient for a solute, K, is the ratio of the concentration of the sample in the organic layer divided by the concentration in the aqueous phase. The partition coefficient is a constant dependent on both the solute and the pair of solvents used in the extraction. The partition coefficient is an expression of preference of the solute for each of the two solvents. Solutes with a large partition coefficient have a higher tendency to be extracted into the organic solvent layer. Solutes with small partition coefficients prefer to transition into the aqueous phase.
Determining which solvent pair to use for a liquid-liquid extraction is a vital step. Consider the following when choosing which solvents to use: First, the solute must be more soluble in the solvent than in water. Therefore, knowing the partition coefficient of the solute in a potential solvent pair is necessary. Second, the solvent-pair must be immiscible in water and not form a homogeneous solution when mixed. Third, the solvents must be inert and not react with the solute. The solvent should also be volatile so that it can be removed from the solute easily. The water-immiscible organic solvent generally possesses a non-polar or low polarity.
It is also critical to know the densities of the solvents to determine the identities of the top and bottom layers. Most organic liquids have a lower density than water, with the exception of chlorinated organic solvents, and will settle to the bottom of the separatory funnel.
Acid-Base Extraction
Acid-base extraction is a type of liquid-liquid extraction that separates organic compounds based on their acid-base properties. If a solute is an acid or base, its charge changes as the pH is changed. Generally, most organic compounds are neutral, and therefore more soluble in organic solvents than they are in water. However, if the organic compound becomes ionic, then it becomes more soluble in water. This is useful in extracting an organic acid or base compound from an organic phase to an aqueous phase.
Acid-base extraction harnesses this property by transforming the solute into its water-soluble salt form, thereby changing its solubility. The solubility of the organic compound and its salt must be dramatically different in order for the technique to be effective.
For example, consider a mixture containing an organic carboxylic acid, an amine, and a neutral compound. Carboxylic acids consisting of six carbons or more are insoluble in water and entirely soluble in organic solvents. However, their conjugate bases (an ionic compound) are water-soluble and insoluble in organic solvents. An amine consisting of at least seven carbons is insoluble in water but soluble in organic solvents. The conjugate acid of that amine (an ionic compound) is water-soluble and insoluble in organic solvents.
When reacted with a base, the carboxylic acid is neutralized to its salt form. The other compounds in the mixture remain neutral. Once the carboxylic acid is transformed into a salt, it will partition to the aqueous phase, while the neutral compounds remain in the organic phase.
Acid-base extraction is also used to separate two weak acids or two weak bases with a significant difference in their pKa. In the case of the acids, the relatively stronger acid, having a small pKa value, is neutralized to a salt using a weak base. The weak base does not efficiently react with the weaker acid, and only the stronger acid is transformed to a salt. Then, the salt is extracted into the aqueous phase during extraction. The process follows similarly for weak bases, where the relatively stronger base is neutralized to a salt using a weak acid.
References
<ol>
	<li style="font-size:17px">Harris, D.C. (2015). Quantitative Chemical Analysis. New York, NY: W.H. Freeman and Company.</li>
</ol>

Extraction

Extraction
Extraction is a common technique used in organic chemistry to isolate a target compound. In the extraction process, a solute is transferred ...

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separating mixtures with solvent extraction

Solvent extraction is a common way to separate and isolate a target compound in organic chemistry. In this process, a solute moves from one phase to another so it can be separated from unreacted starting materials or impurities. Extraction is also useful when a product is dissolved in a reaction solvent that is hard to remove by evaporation, such as a solvent with a high boiling point.

There are three main types of extraction. In solid-liquid extraction, the solute moves from a solid phase into a liquid phase. In liquid-liquid extraction, the solute moves from one liquid into another. In acid-base extraction, the solute is changed into an ionic compound and moved from an organic phase into an aqueous phase. A familiar example is brewing coffee or tea, where hot water extracts caffeine, plant flavors, and odors from the solid material.

Liquid-liquid extraction is used when an organic compound is dissolved in water or when water-soluble impurities need to be removed from an organic product. It works with immiscible liquids, which are liquids that do not form one uniform solution, even after mixing. Oil and water are a common example. To carry out this extraction, the aqueous solution is placed in a separatory funnel, and a non-water-soluble organic solvent is added. After mixing, the compound partitions into the phase where it is more soluble.

Because the two liquids are immiscible, they separate into layers after settling. The denser liquid forms the bottom layer, and the less dense liquid stays on top. The layers are then separated by opening the stopcock at the bottom of the separatory funnel and letting one layer drain out. The layer that loses the solute is called the raffinate, and the layer that gains the solute is called the extract. At equilibrium, the solute has the same chemical potential in both phases.

The partition coefficient, K, describes how a solute divides between the two layers. It is the concentration in the organic layer divided by the concentration in the aqueous layer. This value depends on the solute and the solvent pair used. A large partition coefficient means the solute prefers the organic layer. A small partition coefficient means the solute prefers the aqueous layer. Choosing the right solvent pair is important, so the solute should be more soluble in that solvent than in water, the two solvents should be immiscible, and the solvents should be inert and volatile. The water-immiscible organic solvent is usually non-polar or low in polarity.

Knowing density is also important because it tells which layer is on top and which is on the bottom. Most organic liquids are less dense than water and rise to the top, although chlorinated organic solvents are an exception and can settle to the bottom. Acid-base extraction is a special type of liquid-liquid extraction that separates organic compounds based on acid-base behavior. When pH changes, the charge on an acid or base can change too. Neutral organic compounds are usually more soluble in organic solvents, but ionic forms are more soluble in water.

This property lets chemists turn an organic acid or base into a water-soluble salt. The salt and the neutral compound must have very different solubilities for the method to work well. For example, a mixture may contain an organic carboxylic acid, an amine, and a neutral compound. Carboxylic acids with six carbons or more are insoluble in water and soluble in organic solvents, but their conjugate bases are water-soluble and insoluble in organic solvents. Amines with at least seven carbons are insoluble in water and soluble in organic solvents, while their conjugate acids are water-soluble and insoluble in organic solvents.

When a base is added, the carboxylic acid is neutralized to its salt form, while the other compounds remain neutral. The salt then moves into the aqueous phase, and the neutral compounds stay in the organic phase. Acid-base extraction can also separate two weak acids or two weak bases when their pKa values are far enough apart. For weak acids, the stronger acid with the smaller pKa is converted to a salt using a weak base, while the weaker acid is not reacted much. The same idea applies to weak bases, but a weak acid is used to neutralize the stronger base.

Separating Mixtures with Solvent Extraction

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Separating Mixtures with Solvent Extraction

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