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Separation By Extraction Of Benzoic Acid And Nitrotoluene

Aim: To work with the extraction parting technique to be able to separate an assortment of benzoic acid and 4-nitrotoluene provided. That is carried out to be able to obtain the individual the different parts of the concoction in a purified form by recrystallisation process and whose metling point is set to demonstrate the personality of the ingredient obtained.

1. Benefits:

Separation by extraction is a technique that allows the parting of compounds based on their difference in solubility in two immiscible solvents.

If a solute X is permitted to disperse itself bewteen two immiscible solvents, A and B, then the following equilibrium will be reached:

X (A) X (B)

where A is usually drinking water, the aqueous stage and B is the water-immiscible organic and natural solvent, such as diethyl ether as in this case.

The equilibrium frequent because of this process is known as the circulation coefficient or the partition coefficient, KD or BDA and it is distributed by:

KD (X) = BDA (X) = the concentration of X in phase B = [X]B

the attentiveness of X in stage A [X]A

similarly, for solutes X and Y distributed into two immiscible solvents A and B we may define the following equilibria:

X (A) X(B)

Y (A) Y(B)

and for effective parting by removal of X and Y using solvents A and B, we require that:

KD (X) >> KD (Y)

in which circumstance the majority of X will find itself in solvent B and the majority of Y will find itself in solvent B, or,

KD (X) << KD (Y)

in which case the majority of X will see itself in solvent A and the majority of Y will find itself in solvent B.

Structural method of 4-nitrotoluene

Structural method of benzoic acidAll this is merely a brief background simply showing that the aqueous level, being normal water and the ether, which can be both solvents and are known as A and B, are in equilibrium with one another. Then your benzoic acid / 4-nitrotoluene mix to be separated by extraction, known as Y and X, are the solutes. These types are both insoluble in drinking water and so don't like the polar environment. Hence this is the reason why sodium bicarbonate solution is used. This is useful as to convert the benzoic acid to this inflatable water soluble sodium benzoate. This will then go into the aqueous layer rather than staying in the ether covering. Then focused hydrochloric acid can be used to convert back again to benzoic acid because the benzoic acid must be collected and be purified!

C6H5COOH(s) + NaHCO3 (l) C6H5COO-Na+ (aq) + H2O (l) + CO2 (g)

C6H5COO-Na (aq) + HCl (l) C6H5COOH (s) + NaCl (aq)

Adding on the above mentioned equations one could also mention the actual fact that based on the Bronsted - Lowry classification, an organic acidity is a mixture that reacts to contribute a proton (H+) to basics such as OH- ion.

R-COOH (s) + OH- (aq) R-COO- (aq) + H2O (l)

Organic acid solution conjugate base

(insoluble in water) (soluble in drinking water)

As can be seen from this reaction, the result of the loss of a proton causes the forming of the carboxylic acid's conjugate basic with a negative charge. This fee now allows the chemical substance to dissolve in drinking water. A carboxylic acid's property of creating an ionic conjugate bottom pays to as it allows the separation of carboxylic acids from other chemical substances that do not have this chemical substance property.

In real practice the acid and non - acidity blend is first dissolved in ether, an organic and natural solvent that dissolves most organic compounds. It is noted that a lot of ingredients will dissolve in ether or in drinking water, however, not in both.

In order to conclude once the mixture is segregated by removal, recrystallisation procedures are carried out in order to obtain the individual purified substances. Then the melting point is determined for each to be able to verify the purity of the compound obtained.

2. Method:

2. 1 Chemicals used






Riedel de Haem

Benzoic acid






Sodium hygrogen carbonate



Hydrochloric acid


Riedel de Haem




2. 2 Apparatus

a spatula, goblet rod, digital balance, Bunsen burner, capillary pipes, melting point apparatus, thermometre, separating funnel, stopper, measuring cylinder, 250 mL conical flasks, 100 mL conical flask, beaker, Buchner flask, Buchner funnel, cork, filtration system paper, fluted filter newspaper, stemless funnel, range, steam shower (flameless range) in the fume cupboard, ice-cold normal water, distilled water.

2. 3 Procedure

Part a) Separating the benzoic acid solution and 4-nitrotoluene mixture

2. 001 g benzoic acid solution / 4-nitrotoluene concoction were weighed on an electric balance and positioned in a 250 mL conical flask by means of spatula.

20 mL of diethyl ether were measured by using a measuring cylinder and put into the mixture in the conical flask.

The concoction was the transferred to a separating funnel and 20 mL diethyl sodium bicarbonate solution (5% by mass) were put into it. It was noted that this coverted the benzoic acidity to this soluble sodium benzoate.

The separating funnel was stoppered and shaken for some time. Then it was inverted and the faucet was exposed so that pressure was released. It was then finished and shaking was extended, and the pressure was released frequently until further shaking developed little if any additional pressure.

Finally the tiers were allowed to separate for quite a while and then the bottom covering was run off into a 100 mL conical flask.

Then 10 mL of water were added to the separating funnel and the aqueous level was run off in to the same conical flask.

Part b) Recovering benzoic acid and screening its purity

A few drops of concentrated hydrochloric acid solution were added to the aqueous stage until the pH was significantly less than 2. The pH was checked out with the addition of a drop with the a glass fishing rod onto pH documents provided and the color obtained was examined and weighed against the people provided on paper for reference. The colour seen was orange.

The solution was permitted to stand until crystallisation of benzoic acidity was complete. The beaker was positioned in ice-cold water so that all the solid was permitted to form.

Vacuum filtration was carried out. The equipment was set up and the answer was filtered under suction. The crude benzoic acidity crystals were accumulated in the Buchner funnel on the filtration paper. The crystals were washed twice with normal water and allowed to drain.

They were then recrystallised from drinking water and the benzoic acid solution crystals accumulated were now purified and were used in a clean watch cup by using a spatula. They were permitted to dried on the bench for quite a while.

The mass of the purified benzoic acid solution was found by weighing the watch wine glass and the merchandise. Then when the experiment was in the watch wine glass was weighed clear and subtraction was done in order to get the mass of the purified benzoic acidity.

The melting point was then driven. This was done by first placing a capillary pipe, from its centre, in a Bunsen fire so that two melting point pipes were produced as the capillary pipe melted into 50 %. Then one pipe was used to tap 2-4 mm of natural benzoic acid in to the tube. This is then inverted and tapped contrary to the bench so that the sample used was allowed to move to underneath of the pipe. The pipe was then located in a melting point equipment and the melting point temperature range was found.

Then the percentage recovery was exercised.

Part c) Recovering 4-nitrotoluene and testing its purity

The ether solution was evaporated to dryness over the steam bath (flameless oven) in the fume cupboard.

It was observed that whenever no further loss of the solution, by evaporation, was present the conical flask was removed and was permitted to cool to room temps. When cooled it was put in ice-cold water until the formation of crystals occurred.

The crystals produced were accumulated and recrystallised from ethanol.

The mass of the clean 4-nitrobenzene was found using an electric balance. The melting point was driven and the percentage recovery was worked out.


Separation of two immiscible liquids

(the lighter liquid being the ether level and

the denser liquid being the aqueous layer, in cases like this)


It was made certain that the equipment was cleaned with distilled water so as to prevent contaminants.

It was made certain that the touch of the separating funnel was securely closed from underneath before the mix was used in it, normally this will run out and hence there would be loss of sample mixture prepared!

It was guaranteed that the separating funnel was shaken slowly but surely and carefully and the stopper was pressed during the process in order to prevent it from detachment anticipated to pressure.

It was guaranteed that the touch of the separating funnel was frequently opened after the funnel was shaken and inverted. This is important so that surplus pressure was relieved stopping the funnel from breaking or collapsing.

It was guaranteed that the aqueous part was go out very slowly after the interphase between the ether and the aqueous level approached. This is important so as to have the ability to control the tap and close it quickly in time to be able to prevent drops of ether from jogging out of the funnel with the aqueous part.

It was ensured that the Buchner flask was pressed downwards with the hands during the vacuum purification process. This was done so as to ensure that full suction was present and so vacuum was made, so that purification was done completely.

It was guaranteed that the plastic tubing was disconnected first and then your water aspirator turned off, to be able to prevent sucking again and so contamination of the stable product.

It was guaranteed that both the stemless funnel and the conical flask were warmed just a little before hot gravity filtration was completed, by positioning them within an oven for a short while. This is important so as to prevent premature crystallisation.

It was made certain that attention was used when the capillary tube was placed in to the Bunsen flame in order to melt it into 1 / 2, otherwise one could have hurt the hands or fingertips even though gloves were worn.

3. Results and Computations:

3. 1 Results

mass of benzoic acidity / 4-nitrotoluene concoction weighed = 2. 001 g

For purified benozic acid solution:

mass obtained = 0. 333 g

melting point temp range obtained = 120 - 122 C

percentage yield computed = 33. 3 %

For purified 4-nitrotoluene:

mass obtained = 0. 268 g

melting point temp range obtained = 51 - 52 C

percentage yield calculated = 26. 8 %

3. 2 Calculations

mass of purified benzoic acid & watch wine glass = 25. 142 g -

mass of watch wine glass only = 24. 809 g

mass of purified benzoic acidity = 0. 333 g

Percentage Recovery for purified benzoic acid:

% yield = genuine mass X 100 %

theoretical mass

= 0. 333 g X 100 %

1 g

% yield = 33. 3 %

mass of purified 4-nitrobenzene & watch glass = 28. 702 g -

mass of watch goblet only = 28. 434 g

mass of purified 4-nitrotoluene = 0. 2680 g

Percentage Recovery for purified 4-nitrobenzene:

% produce = real mass X 100 %

theoretical mass

= 0. 268 g X 100 %

1 g

% yield = 26. 8 %

Sources of error

Parallax errors were avoided whenever you can by looking normally to the range of the thermometre when taking the melting point temperatures range. Also when measuring volumes of reagents using calculating cylinders.

During the vacuum filtration for the recrystaiisation process, a few of the product i. e. benzoic acid solution and in another suction, 4-nitrotoluene just went throught the filter paper and into the Buchner flask. Hence the purified product obtained on hte Buchner funnel had not been the total product obtained by parting. Unfortunately, credited to insufficient time, the process cannot be repeated again. Hence the results obtained mixed and percentage produce calculated was lower.

The purified products obtained weren't allowed to dry completely before their mass was used. Hence this might slightly influenced the results obtained because the mass could may have been just a little higher due to some solvent still present.

During the parting of the 4-nitrotoluene / benzoic acidity mixture through extraction using the separating funnel, it was quite difficult to stop the run at the interphase between your ether and the aqueous covering. Hence a drop of the ether layer was run out in to the conical flask by mistake and hence blended with the aquoeous level. Which means that there is no complete parting of the two.

4. Dialogue:

The objective of an extraction is to recover valuable soluble components from raw materials by first dissolving them in the liquid solvent, so that the components can be later separated and retrieved from the water.

Is is available that removal is applied to a variety of food products, for example the extraction of sugars from sugar-cane or sugar-beets, the extraction of oil from oil seeds, the removal of coffee extract from coffees, the extraction of various other components such as proteins, natural vitamins, pigments, essential natural oils, flavoured chemical substances, amonsgts others. Hence, the extraction of these products allows their parting from numerous materials.

Extraction process can be calssified predicated on combination of stages (stable, liquid, gas and supercritical substance). The solid - liquid is a type of extraction that pays to for the isolation and purification of obviously occuring sources. Alternatively the water - liquid is a far more common method depending on solubility propertiesof components.

Regarding solvents, it can be said that there surely is a number of solvents you can use. Solvents found in separation of a mixture by removal may be organic solvents that are denser than water; for example dichloromethane, chloroform and carbon tetrachloride. On the other hand they could also be organic and natural solvents which can be less dense than drinking water; for example diethyl ether, toluene, hexane. In this experiment ether was used and this is very commonly used because ether is very immiscible with water, they have very powerful solvent properties for non-polar solvents, it includes very low boiling point (35 C) hence it can be evaporated easily following the extraction. However special health care must be taken when controlling this solvent since it is extremely volatile and flammable. In particular, all naked flames in the immediate vicinity should be extinguished.

A solvent is vital in the extraction process. A solvent is truly a liquid, solid, or gas that dissolves another stable, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature.

In this experiment liquid-liquid extraction was carried out. This is also called solvent removal and partitioning and this method was found in order to split up compounds predicated on their comparative solubilities in two different immiscible liquids, which are drinking water and an organic solvent. It really is an extraction of an substance from one liquid stage into another liquid period. Liquid-liquid extraction is a simple technique in substance laboratories, where it is performed utilizing a separatory funnel.

In other words, liquid-liquid extraction is the parting of a substance from a mixture by dissolving that compound in the right solvent. By this process a soluble ingredient is usually segregated from an insoluble ingredient.

One should say that solvent extraction can be used in nuclear reprocessing, ore control, the production of fine organic compounds, the handling of perfumes, and other establishments.

While solvent extraction is often done on a tiny range by laboratory chemists using a separatory funnel, it is normally done on the commercial level using machines that bring both liquid phases into contact with each other. Simply for the sake of mentioning them such machines include centrifugal contactors, slim layer extractors, aerosol columns, pulsed columns, and mixer-settlers.

This brings us to the value of using a separating funnel by which an extraction parting process can be carried out. A separating funnel is a pear-shaped lab apparatus which is employed to separate two immiscible fluids that are usually very hard to split up, for case ether and drinking water. It is very useful because the layers of the two liquids could be observed very easily, with the naked eyeball, separated from the side of the funnel. The separating funnel usually has a short stem which is installed with a earth goblet interchangeable stopper. The size of the separating funnel must always be about twice the volume to be extracted. It is usually very helpful and convenient to have the separating funnel installed in a engagement ring over a stand with a company base.

Discussing the results obtained it was observed that the percentage yield determined was quite low. Hence a lot of the merchandise was lost and a mention of this was brought up as one of the sources of mistake, where some product had not been considered since it handed through the filter paper into the Buchner flask and the recystallisation process had not been repeated. This may occurred because of the filter paper used, not being of the correct size.

In order to conclude you can discuss an adjustment which could be done to these process for the parting of a mixture of benzoic acid solution and 4-nitrophenol. As stated in the benefits and further on with it in the task, the steps carried in the laboratory during the experiment were different from the ones below.

Initially acid anhydride is added and the 4-nitrophenol becomes 4-nitrophenyl ethanoate which can be an ester that is soluble in ether. Then sodium bicarbonate is added which is not alkaline enough to be able to convert the ester into alcohol but is alkaline enough to be able to convert the benzoic acid into benzoate, which is soluble in normal water. Then extraction is performed and NaOH is put into the ester and 4-nitophenol is obtained again. Concentrated hydrochloric acidity is then put into the benzoate until crystallisation of benzoic acidity occurs. Hence the individual compenents are obtained and in a clean form after the recrystallisation process is carried out.

5. Summary:

It as concluded that the benzoic acidity / 4-nitrotoluene blend was separated through extraction. Hence the individual the different parts of the combination were obtained separately and in a purified form by recrystallisation functions. The melting point of the purified crystals was also found, confirming the purity of the substances.

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