BACHELOR OF SCIENCE (HONS) CHEMISTRY

UDEC 1224 CHEMISTRY LABORATORY II

NAME: HARVINDAEN A/L MUNIANDY

STUDENT ID: 1606466
PATNER NAME&ID: CHAI JIAN WEI (1504143)
LIM FOOK CHIN (1606748)
EXPERIMENT NUMBER: 13
EXPERIMENT TITTLE: EXTRACTION : EXTRACTION
WITH ACID AND ALKALINE
DATE OF EXPERIMENT: 03/06/2017
PRACTICAL GROUP: 1
DATE OF SUBMISSION: 17/07/2017
LECTURER NAME: DR MOHAMMOD AMINUZZAMAN
Tittle: Extraction with acid and alkaline

Objective:

1) To recover benzoic acid and p-dichlorobenzene from its mixture using acid-alkaline

extraction method

2) To determine the percentage recovery of benzoic acid and p-dichlorobenzene

3) To determine the melting point of recovered benzoic acid and p-dichlorobenzene

Introduction:

Solvent extraction is a method to separate compounds based on their relative solubility in two

different immiscible solutions. Solvent extraction is also known as liquid-liquid extraction or

partitioning. Solvent extraction is a method that usually used to recover a compound from

solid or liquid. The sample is contacted with a solvent that will dissolve solutes of interest.

Solvent extraction is a major method and most efficient method of separation of interested

product from a complex feedstock. The solvent can be a vapour, supercritical fluid, or liquid

whereas the sample can be a gas, liquid or solid.

Frequently the cleanest separations of organic compounds can be effected by use of acid or

alkaline solutions which convert the compound to be extracted to a water-soluble, ether

insoluble salt. A 5 or 10 per cent solution of sodium hydroxide, for example, can convert

carboxylic acid to its carboxylate sodium salt, RCO2-Na+. Phenolic compounds undergo

similar salt formation with sodium hydroxide solution. Hence, a sodium hydroxide solution

can be used to extract a carboxylic acid or phenolic compound from its solution in an organic

solvent, or conversely, an organic solvent can be used to remove organic impurities from a

carboxylic acid or phenol dissolved in aqueous sodium hydroxide.

Aqueous solutions of sodium bicarbonate likewise convert carboxylic acids to their sodium

salts, but are not sufficiently alkaline to form salts of phenolic compounds. This provides an

elegant method for the separation of a carboxylic acid and a phenolic compound. First the
acid may be removed from solution in an organic solvent by means of extraction with sodium

bicarbonate solution, and then the phenol, with sodium hydroxide solution. Inorganic acids

are regularly removed from organic solvents by extraction with sodium hydroxide, sodium

carbonate, or sodium carbonate solutions. Dilute hydrochloric acid is often used in the

extraction of basic substances from mixtures or in the removal of basic impurities. The dilute

acid converts the base such as ammonia or an organic amine (R3N) into the water-soluble

chloride salt (R3 NH+, Cl-). Conversely, organic impurities may be removed from amines by

extraction from a dilute acid solution with organic solvents.

Sodium salts of carboxylic acids and phenolic compounds are readily reconverted to the

parent compounds by treatment with sulphuric or phosphoric acid. The chlorides of amines

revert to the original amine upon addition of sodium hydroxide solution.

Apparatus and materials:

Separating funnel (250 mL)

Buchner funnel

benzoic acid

p-dichlorobenzene

dichloromethane

10% NaOH

concentrated HCl

litmus paper

distilled water

anhydrous CaCl2.
Experimental procedures:

1) 40 ml of dichloromethane was poured into a dry 100 ml conical flask which contained 1 g

of benzoic acid and 1 g of p-dichlorobenzene mixture.

2) A glass rod was used to mix and dissolve the solid mixture.

3) The dichloromethane was transferred into a separating funnel.

4) 20 ml of freshly prepared 10% NaOH solution was added into the separating funnel.

5) The separating funnel was stoppered, shaked well, occasionally inverted and surplus

pressure was released through the stopcock.

6) The separating funnel was allowed to stand in a ring clamp.

7) The stopper was removed and the lower organic (dichloromethane) layer was ran into a

beaker.

8) The aqueous layer was removed into a 250 ml beaker and kept aside.

9) The dichloromethane layer (in the beaker point number 7) was transferred back to the

separating funnel and another portion of 20 ml 10% NaOH was added.

10) The separating funnel was stoppered, shaked well, occasionally inverted and surplus

pressure was released through the stopcock.

11) The separating funnel was allowed to stand in a ring clamp.

12) The stopper was removed and the lower organic (dichloromethane) layer was ran into a

beaker.

13) A spatula of anhydrous CaCl2 was added to the dichloromethane layer and the mixture

was shaked occasionally with no turbidity remains.

14) Then the dichloromethane was filtered through a small piece of cotton wool on a dry

glass funnel.

15) The dry dichloromethane solution was collected in a dry pre-weighed 100 ml beaker.

16) One to two boiling chips was added and the beaker was placed on a hot plate inside the
fume hood.

17) As soon as all the dichloromethane has evaporated the beaker was weighed again to

obtain the mass of recovered p-dichlorobenzene.

18) The melting point and percentage recovery of p-dichlorobenzene was determined.

19) To the solution of the aqueous layer in 250 ml beaker dropwise of concentrated HCl was

added until the mixture became acidic until no further precipitation occurs.

20) The precipitate benzoic acid was filtered using a Buchner funnel and a filter flask.

21) The benzoic acid in the Buchner flask was washed with 5-10 ml of cold distilled water.

22) The filtered benzoic acid was transferred on a filter paper and the benzoic acid was

pressed using another filter paper to ensure the crystals are completely dried.

23) The mass recovery, percentage recovery, and the melting point of the benzoic acid was

determined.

Results:

Mass of benzoic acid: 1.0060 g

mass of p-dichlorobenzene: 1.0024 g

Benzoic acid:

mass of empty watch glass= 32.4486 g

mass of watch glass + benzoic acid= 33.2679 g

mass of benzoic acid= 0.8193 g

melting point of benzoic acid = 116C

percentage recovery=

weight of compound recovered / weight of compound started with x 100%

0.8193g / 1.0060g x 100% = 81.44%

p-dichlorobenzene:
mass of empty beaker= 54.0228 g

mass of beaker + p-dichlorobenzene= 54.7703 g

mass of p-dichlorobenzene recovered= 0.7415 g

melting point of p-dichlorobenzene= 57C

percentage recovery=

weight of compound recovered / weight of compound started with x 100%

0.7415g / 1.0024g x 100% = 73.97%

Discussion:
Two layers of solution are formed in the separating funnel which upper layer is organic layer
(benzoic acid) while the lower layer is aqueous layer (p-dichlorobenzene). The sodium salt of
benzoic acid dissolve in the aqueous layer which runs off into a conical flask. The second
time of addition of 20 ml 10% NaOH into the solvent is used to make sure that all the benzoic
acid is reacted completely with sodium hydroxide. This reaction caused the similar two layers
are formed and the aqueous layer is transferred into the same conical flask by using the same
method. The reaction between benzoic acid and sodium hydroxide produces a lot of vapour
after few times of shaking.

The organic layer collected was added with HCl dropwise. White precipitate was formed.
Then the precipitate was filtered and the product filtered was washed with cold water. The
purpose of using cold water is to minimize the solubility of benzoic acid where benzoic acid
is less soluble to cold water. The weight of recovered benzoic acid was about 0.8193 g, the
melting point is 116C. The percentage recovery of the product was 81.44%. The product
might lose during conducting the experiment. This may due to the some of the product
dissolve during the filtration where the filtration must be done carefully to avoid such lose.

Calcium chloride is added to the benzoic acid. The purpose of add is to absorb water in the
organic solvent. The calcium chloride is known as drying agent which doesnt dissolve in the
solvent which will form hydrates when react with water as shown in equation below:
CaCl2(s) + H2O(l) CaCl2. H2O(s)
The p-dichlorobenzene collected was evaporated on a hot plate in the fume hood with some
boiling chips added to the solution. The boiling chips are small, insoluble, and porous stones
made of calcium carbonate or silicon carbide. There are a lot of pores inside the boiling chips
which provide cavities both to trap air and to provide spaces to allow bubbles of solvent can
be form. When boiling chips are heated, it will release tiny bubbles which can minimise
boiling over. White p-dichlorobenzene is formed in the crystal form after all the solution in
the beaker evaporates. The weight of recovered p-dichlorobenzene was about 0.7415 g, the
melting point is 57C. The percentage recovery of the product was 73.97%. Some of the
product was lost during conducting the experiment where we believe that boiling over has
occurred although boiling chips was added. This may due volume of the solution evaporated
and the amount of boiling chips added is not tally because the volume of the solution is more
and the boiling chips added is not enough to minimise the boiling over. We should add more
boiling chips to obtain more precise results.

Precautions:
1) Students are advised to wear lab coat, goggles and gloves throughout carrying out the
experiment.
2) The adding of HCl to the organic layer must be done in the fume hood as the HCl used is
concentrated.
3) The evaporation on the hot plate must be done in the fume hood
4) The separating funnel must be handled carefully and follow the instruction given by
instructor to release the pressure to avoid breakage of the apparatus.
5) Add correct amount of boiling chips as adding more boiling chips may results in severe
boiling and damage the apparatus.

Conclusion:
The weight of recovered benzoic acid was about 0.8193 g, the melting point is 116C. The
percentage recovery of the product was 81.44%. Meanwhile, the weight of recovered p-
dichlorobenzene was about 0.7415 g, the melting point is 57C. The percentage recovery of
the product was 73.97%.
The results obtained was not so precise due to some errors that occurred during conducting
the experiment.
References:

Anon., 2013. Extraction: Separation of Acidic Substances. [Online]

Available at:
http://www.xula.edu/chemistry/documents/orgleclab/Acidic%20Extraction%20procedure_v2.pdf
[Accessed 15 July 2017].

Anon., n.d. Boiling Chips - Organic Chemistry at CU Boulder. [Online]

Available at: http://orgchemboulder.com/Technique/Procedures/Distillation/Boilingchips.shtml
[Accessed 15 July 2017].

Anon., n.d. Extraction. [Online]

Available at:
http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/Techniques/E
xtraction/extraction_n.html
[Accessed 15 July 2017].

Anon., n.d. Melting Point of an Organic Compound. (Theory). [Online]

Available at: http://amrita.olabs.edu.in/?sub=73&brch=7&sim=33&cnt=1
[Accessed 15 July 2017].

central, R., 2012. Properties of Calcium Chloride and mixing with water. [Online]
Available at: http://www.reefcentral.com/forums/showthread.php?t=2203504
[Accessed 15 July 2017].