TITLE : 1) EXPERIMENT 1 (RECRYSTALLIZATION OF VANILLIN)

: 2) EXPERIMENT 2 (MELTING POINT DETERMINATION)

NAME : ATHIRAH BT. ABDUL KAMIL (2007116909)

LAB PARTNER : NURADHAM FARHANA BT. ZALI (2007116741)
GROUP : ASD4Bn
COURSE : DIPLOMA IN SCIENCE
DATE OF THE EXPERIMENT : 13RD JULY 2009 & 3RD AUGUST 2009
DATE OF REPORT SUBMISSION : 10TH AUGUST 2009
OBJECTIVES :

1. To purify the vanillin by recrystallization procedure and to determine the recovery

percentage. The purified vanillin samples will be evaluated through melting point on
the next experiment.
2. To take melting point using the capillary tube.

PROCEDURE :

1. 2 g of vanillin was weighed into a 120 ml Erlenmeyer flask.

2. About 50 ml of water was added to the flask and was stirred vigorously.
3. By using Bunsen burner, the solution was heated just to the boiling point and stirred
until all the vanillin dissolved.
4. The flask was placed in an ice bath for about 5 minutes and was stirred occasionally.
5. A fitted piece of filter paper was placed properly in Buchner funnel by making sure
that all the holes were covered. The paper was being wet by deionised water from
wash and the vanillin crystals were vacuum-filtered.
5 ml of ice-cooled water was used to rinse the Erlenmeyer flask twice and the same
water was used again to wash the crystals in the funnel.
6. The crystal was emptied onto a weighed piece of filter paper and was placed in the
desk for drying purpose for about three weeks and being sure that it cannot spill.
7. The automatic melting point determination machine called Mel-Temp apparatus was
used to measure the recrystallized vanillin and crude vanillin melting point.
8. The capillary tube was filled by crude vanillin sample which was pressed at the open
end until there was about 0.5-1cm length of sample in the tube.
9. The capillary tube was dropped; the end sealed went down through a 1m piece of
6mm glass tubing that was being held on a hard surface.
10. The impact of capillary with the hard surface seldom resulted on breaking and caused
the sample to drop to the bottom of the tube.
11. The dropping procedure was repeated until the sample was packed in the bottom of
the tube.
12. The capillary tube was attached with the Mel-Temp apparatus holes. The start button
was pushed when the plateau light was on along with the ramping light.
13. Procedure 7 until 11 was repeated for the recrystallized vanillin sample. The sample
was grounded in a mortar before it was pressed at the open end of the capillary tube.
14. The temperature for both samples was recorded in the table.
 DATA & OBSERVATION :

PROCEDURE OBSERVATION
1. 2 g of vanillin weighed into 250 ml A crystal of vanillin was weighed on a weighing
Erlenmeyer flask. machine. We obtained 2.0021 g of vanillin and 0.3755 g
of filter paper.
2. Stir 50 ml of water in the flask. The crystal of vanillin was dissolved incompletely.
3. The solution heated with Bunsen The crystal of vanillin was heated and the colour
burner until boiling point and stir change from white to colourless. The vanillin dissolved
until all vanillin dissolved. completely.
4. Stir the solution in flask that placed in After stirring the solution for 5 minutes the precipitate
ice bath for 5 minutes. present.
5. A piece of wet filter paper fitted to The filter paper must stick to the Buchner surface. At
the Buchner funnel. The vanillin was this stage, the tap water must be opened all the time to
vacuum filtered. The Erlenmeyer flask let the water flow. We make sure that the crystal dry in
was rinse twice with ice-cooled water Buchner flask.
along with the crystals.
6. The crystals emptied onto a weighed The dried crystals + filter paper in a petry dish for 3
filter paper and placed in the desk to weeks
dry.
7. The automatic melting point The apparatus was set up as in the manual.
determination machine called Mel-
Temp apparatus was used.
8. The capillary tube filled with The recrystallized vanillin was grind in a mortar to make
recrystallized vanillin at the open end powder so that it is easier to be pressed to the open
until there is about 0.5 – 1 cm sample end of the tube.
length.
9. The capillary tube was dropped The powder in the capillary tube was dropped until it
through 1 m piece of 6 mm of glass reached the bottom of the tube.
tubing held on hard surface.
10. The impact caused the sample to The powder length in the tube after the impact was 1
drop to bottom of the tube mm. Then we put the capillary tube in the hole of Mel-
Temp apparatus.
11. Then we put the capillary tube in the When the plateau light is on, we pushed the start
hole of Mel-Temp apparatus. button. After that the ramping light is on too. When the
temperature reached 80℃ the powder start to melt.
Then when it reached 83℃ it liquefies completely. This
is because it contains impurities as there is presence of
foreign matter in it. Finally we let the sample cool to
room temperature.
12. Fill the capillary tube with crude The procedure for recrystallized vanillin is the same for
vanillin. crude vanillin. When the temperature reached 81℃ the
crude vanillin start to melt. Then when it reached 83℃
it liquefies completely. Finally we let the sample cool to
room temperature.
RESULTS :
RECRYSTALLIZED VANILLIN RESULT :

DATA READING
Mass of crude vanillin 2.0021 g
Mass of empty filter paper 0.3755 g
Mass of recrystallize of vanillin + filter paper 2.1774 g
Mass of recrystallize of vanillin 1.8019 g

MELTING POINT DETERMINATION RESULT :

DATA READING
Melting point of crude vanillin 81℃ - 83℃
Melting point recrystallized vanillin 80℃ - 83℃

PERCENT RECOVERY :

Mass of recrystallized vanillin x 100 = 1.8019 g x 100

Crude vanillin 2.0021 g

= 90% pure vanillin

= 10% loss

1℃ 1% - 10% impurities

90% of the recrystallized vanillin is pure vanillin while 10% of the recrystallized
vanillin is the impurities. This shows that although we vacuum filter the solution but
the impurities still able to escape.

QUESTIONS AND ANSWERS :

1. What is the percent recovery?

The percent recovery is 90% pure vanillin, so the loss is 10%.
2. Why is the vanillin solution cooled in an ice bath before vacuum filtration?
The vanillin solution was cooled in an ice bath before it underwent vacuum filtration
because the solution is usually cooled with an ice bath to further decrease the
solubility of solid in the solvent thus; resulted to the crystallization.
3. How does the recrystallization procedure remove solvent soluble impurities?
The solvent soluble impurities was removed in the recrystallization procedure by
underwent filtration. As the solubility decreased, the temperature dropped and the
solid crystallizes back out upon cooling. These impurities pass through the final cold
filtration.
4. What additional step should be added to this procedure to remove impurities
insoluble in solvent?
The additional step that should be added to this procedure is by including gravity
filtration of the hot solution to remove the insoluble impurities.
5. Gravity and vacuum filtration separate insoluble solids from a liquid phase. The
choice depends on conditions. Suggest criteria you would apply to choose between
them.
Gravity filtration is the most commonly used filtration technique. The use of filter
paper in this type of filtration allows gravity to draw liquid through the paper. A small
piece of filter paper will absorb a significant volume of liquid. This technique is useful
when the volume of mixture to be filtered is greater than 10 ml. On the other hand,
vacuum filtration is much faster than the gravity filtration and is most often used to
assemble solid products resulting from precipitation or crystallization. This technique
is used primarily when the volume of liquid is being filtered more than 1-2ml. As a
conclusion, I would choose the vacuum filtration. This is because it will filter
impurities greater than the gravity filtration and it saves time as it operates much
faster than the gravity filtration.
6. Suggest any ways you can think of improve any parts of this experiment?
In my opinion, there is a part of this experiment that can be improved like we can
remove insoluble impurities that are present by hot filtration. Besides that, we
should watch the dissolution process carefully to avoid using too much solvent and
risking poor recovery of the purified solute. On the other hand, to keep liquid from
flowing over the top of the funnel, we make sure the top of the paper should not
extend above the funnel by more than 1 – 2 mm.
7. Compare your answer with literature melting point of 81℃ - 83℃ of vanillin,
comment on the purity of the crude and recrystallized vanillin and also the success
of your recrystallization.
The melting point for the crude vanillin is within 81℃ - 83℃ while the melting point
for the recrystallized vanillin powder is 80℃-83℃. At 80℃, the recrystallized vanillin
powder started to melt while at 83℃ the powder is liquefying completely. It means
that the sample is impurities because there is a foreign matter present. So our
recrystallization is quite successful.

DISCUSSION OF RESULTS :

1. The first experiment is recrystallization of vanillin. Its purpose is to purify the

vanillin by recrystallization procedure and to determine the percentage. The purified
vanillin samples will be evaluated through melting point on the next experiment.
Vanillin, methyl vanillin, or 4-hydroxy-3-methoxybenzaldehyde, is an organic
compound with the molecular formula C 8H8O3. Its functional groups include
aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla
bean. It is also found in roasted coffee [Wikipedia Online Encyclopaedia].
]

The technique used in the experiment are the selection of the appropriate
solvent, dissolution of the solid to be purified in the solvent near or at its boiling
point, formation of crystalline solid from the solution as it cools, the filtration of the
purified solid that will be isolated and drying the crystals [Gilbert & Martin, 2002].

In this experiment, we need to weigh the vanillin crystal which is put on the
weighing paper in the weighing machine to get the mass of the vanillin crystal. The
mass of vanillin crystal is 2.0021 g. Then we heated the vanillin crystal in 250 ml
Erlenmeyer flask which added with distilled water that act as a solvent. We use
Erlenmeyer flask instead of a beaker because beaker is not a suitable vessel for
recrystallization because it has a relatively large surface area to which recrystallized
product may stick thus; lowering the efficiency of recovery. We need to heat the
vanillin crystal because as the solvent temperature increased, the solubility of solids
in liquids will increase significantly too. Furthermore, almost all solids are more
soluble in a hot than in a cold solvent [Gilbert & Martin, 2002].

After stirring the solution for 5 minutes the precipitate present. The extent to
which the solid precipitates depends on the difference in its solubility in the
particular solvent at temperatures between the extreme used. When we vacuum
filter the vanillin, the tap water must be opened all the time to let the water flow. We
make sure that the crystal dry in Buchner flask so that it will not drip. We let the
crystal in the desk to dry for three weeks before we further to the second
experiment.

The second experiment is melting point determination. Its purpose is to take

melting point using the capillary tube. The melting point of a substance means the
temperature at which the liquid and solid phases exist in equilibrium with one
another without change of temperature. However, if impurities present in a
substance the melting points will be compromised. The presence of impurities will
decrease the melting point of a pure solid [Gilbert & Martin, 2002].

In this experiment, we managed to obtain the melting point for the crude
vanillin which is 81℃ - 83℃. However, the melting point for recrystallized vanillin is
80℃ - 83℃. The percent recovery for recrystallized vanillin is 90% pure vanillin while
the other 10% is its’ loss. This happened because the sample is impurity as there is
some foreign matter present in the sample. The purity of compound or the pure
compound is a homogenous sample consisting only of molecules having the same
structure. So, it could be that the recrystallized vanillin is impure due to the presence
of contaminants like paper fibre from filter paper [Gilbert & Martin, 2002]. The
 difference of the melting point between crude vanillin and the recrystallized vanillin
is 1℃ equivalent to 1% - 10% loss.

While conducting these experiments, some errors occurred like in the first
experiment we did not plaster the Buchner funnel to the Erlenmeyer flask properly.
This has caused the loss of water pressure inside the flask. So, to overcome this
problem, we redo the plastering by plastering it tighter than before. Besides that, in
the second experiment we did not stay near Mel-Temp apparatus when the
temperature of recrystallized vanillin exceed to 80℃ thus; we get quite a large range
of temperature reading compared to the crude vanillin temperature range. So, we
redo it by using new capillary tube filled with recrystallized vanillin and stay near the
Mel-Temp apparatus until we managed to get the temperature correctly.

CONCLUSION :

From the experiment, I can conclude that the purpose of this experiment is to purify
the vanillin by recrystallization procedure, to determine the recovery percentage and
to determine the melting point by using capillary tube. The melting point for
recrystallized vanillin is 80℃ - 83℃ while the temperature for crude vanillin is 81℃ -
83℃. The percent recovery is 90% pure vanillin while the other 10% is its loss.

REFERENCES:

1. Gilbert C. J, Martin F. S, Experimental Organic Chemistry A Miniscale and Microscale

Approach, Third Edition, Thomson, 2002.
2. http://www.wikipedia.com