ORGANIC

CHEMISTRY LABORATORY I
BSK1402

LAB REPORT

EXPERIMENT 2: liquid-liquid extraction

_________________________________________

NAME Fathul Aiman Bin Fahmi

MATRIX NO. Sa18094
SECTION 02
DATE 18/2/2019
 ABSTRACT

The objective of this experiment is to separate the benzoic acid from two organic compound mixture

(naphthalene and benzoic acid) where the mixture of 0.5g of benzoic acid and 0.5 g of naphthalene has

been mixed in 25 mL of dichloromethane. Then, the 25 mL of 10% aqueous NaOH has been added

after the solution was placed into a separation funnel and the result shows that 2 layers was formed

which is aqueous phase are in the top while the organic phase on a bottom and were extracted it

thoroughly and the two phases are allowed separate completely. Then, the aqueous phase has been

washed with 10mL of dichloromethane. After that the aqueous layer was poured into a small beaker

and cooled it at 15°c. While the solution was stirred, the HCl has been added (drop by drop) were the

pH are obtained at 1. Then, the product has been filtered and the precipitate has been rinsed from the

beaker into the funnel. Finally, the dried product was weighted and the percent recovery has been

calculated. The resulting show that the weight of dry product is 0.2602 g.In conclusion, the result show

that the benzoic acid can be separate from two organic compound by using this method and achieve the

objective of the experiment.

Keyword: Benzoic acid, NaOH , Separation funnel, HCl , Naphthalene

 INTRODUCTION

The objective of this report is to show how to separate the compounds based on their relative
solubility’s in two different immiscible liquids, usually water and an organic solvent by using
liquid-liquid extraction method. Liquid-liquid extraction is a basic technique in chemical
laboratories, where it is performed using a separator funnel. Liquid-liquid (or solvent)
extraction is a counter current separation process for isolating the constituents of a liquid
mixture. In its simplest form, this involves the extraction of a solute from a binary solution by
bringing it into contact with a second immiscible solvent in which the solute is soluble. In
practical terms, however, many solutes may be present in the initial solution and die extracting
‘solvent’ may be a mixture of solvents designed to be selective for one or more solutes,
depending upon their chemical type. Solvent extraction is an old, established process and
together with distillation constitute the two most important industrial separation procedures.
The first commercially-successful liquid-liquid extraction operation was developed for the
petroleum industry in 1909 when Edelman’s process was employed for the removal of aromatic
hydrocarbons from kerosene, using liquid sulphur dioxide as solvent. Since then many other
processes have been developed by the petroleum, chemical, metallurgical, nuclear,
pharmaceutical and food processing industries.
METHODOLOGY

A mixture of 0.5 g of benzoic acid

and 0.5g of naphthalene has been
dissolved in 25 mL of
dichloromethane

The solution has been placed into a

separatory funnel.

25 mL of 10% of aqueous NaOH

was added into the mixture solution.

The aqueous phase and organic phase

was exctracted throughly and the two
phases are allow seperated
completely.

The aqueous phase has been washed

with 10 mL of dichlromethane.

The aqueous layer has been poured

into a small beaker and cooed it at
15°c.

While stirred the aqueous layer,Ice -

cold concentrated HCl has been
added (drop by drop) untill the pH is
obtained at 1.

The precipitate has been rinsed from

the beaker into the funnel by using
filtrate .

The dried product has been weighted

and the percent recovery has been
calculated.

All the related data has been

recorded.
 RESULT

Filter Paper + Petri dish (A) 53.5181 g

Wet Filter Paper + Petri Dish ( B) 55.3027 g
Dry Filter Paper + Petri Dish (C) 53.2579 g
Mass of Benzoic Acid 0.2602 g
Recovery Percent 52.04 %

CALCULATION

Percent recovery = (𝑎𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑠𝑢𝑏𝑠𝑡𝑎𝑛𝑐𝑒 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑 𝑜𝑛 𝑒𝑥𝑡𝑟𝑎𝑐𝑡𝑖𝑜𝑛 /

𝑎𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑠𝑢𝑏𝑠𝑡𝑎𝑛𝑐𝑒 𝑜𝑟𝑖𝑔𝑖𝑛𝑎𝑙𝑙𝑦 𝑡𝑎𝑘𝑒𝑛) × 100

0.2602g/0.5000g × 100 = 52.04 % percent of recovery for benzoic acid

26
 DISCUSSION

Figure 1.1 : The chemical reaction during extraction process

Figure 1.1 illustrated the reaction during extraction process and it found that the benzoic acid
is obtained in crystal form as the last product.Based on the result, the weight of benzoic acid
crystals after drying process is 0.2602 g. It found that there was a 52.04% recovery for benzoic
acid from the initial amount. However, it may slightly vary from the amount of the initial. This
may be due to the loss of product on the filter during drying process and the percent recovery
less than 100% also indicate either an incomplete reaction and the reactants are not completely
converted to product. The second reasons, all some of the product may not crystallize or
precipitate out in the purification of benzoic acid process. It can also be a source of error if the
excess is due to incomplete removal of water or other impurities from the sample. (1) The
reasons why dichloromethane were used as a solvent because it is volatile, colourless liquid,
not unpleasant odour. It’s immiscible with water but can dissolve a wide range of organic
compounds and these properties make it the perfect solvent for use in the lab specially to
separate and extract organic products.
 C₇H₆O₂ (s) + NaOH (aq) →C₇H₅NaO₂ (aq) + H₂O (l)

C₇H₅NaO₂ (aq) + HCl (aq) →C₇H₆O₂ (s) + NaCl (aq)

(2) The reasons why NaOH were added because to remove the benzoic acid from the mixture
compound. Well the acid is soluble in aqueous base because it reacts with the base and form a
highly polar salt, sodium benzoate. In general, NaOH act as aqueous base to remove the benzoic
acid from the mixture of the two dissolved in dichloromethane. While, the HCl were added
because to make the aqueous sodium benzoate into solution acidic. The figure 1.1 illustrates
how the reaction become when NaoH and HCl was added. (3) To test the organic and aqueous
in the mixture are by perform the water drop test. If the top layer is aqueous, the water droplets
should mix with the top layer, and they will look as if they disappear. If the bottom layer is
aqueous, the water droplets will fall through the top layer to mix with the bottom layer. (4) The
application of liquid extraction in were applied in industrial chemistry in separation of
pollutants for the minimization of waste water streams purpose.
 CONCLUSION

The resulting show that, the benzoic acid can be separate benzoic acid from the mixture of the
two dissolved in dichloromethane by using extraction liquid-liquid technique where NaOH act
as aqueous was reacted with the mixture solution and formed 2 layers which is organic phase
and aqueous phase. Then the HCL are added into aqueous phase and benzoic acid crystal was
formed and going to drying process to get the dry product. The mass of product after drying
process is 0.2602 g and it was 52.04% percent of recovery for benzoic acid based on the amount
of the initial mixture. This low recovery may have resulted from some sodium benzoate
remaining in the aqueous layer because it is does not fully react with the HCl The
recommendation to improve the experiment is carefully keep temperature of reaction and liquid
reagents at the correct level during addition and reaction. Second, make sure to perform the
water drops test if necessary when to decide the aqueous and organic phase layers during
experiment. In conclusion, the benzoic was separated completely and the achieved the
objective of the experiment.
 APPENDIX

Figure 1: The product after drying process

REFERENCE