Extraction of Nicotine from Tobacco Leaves

Ma. Rio Lauren M. Imbao, Jasmine Mary A. Jamorabon, Kurt Raven T. Lai, Beatrice Andrea
G. Lim, Danvel C. Liwag
Group 5 2C Biochemistry Organic Analysis Laboratory

ABSTRACT
Nicotine is an alkaloid which is commonly found in tobacco plants. It was isolated from 8.4048
g dried tobacco leaves by multiple extraction using a 250-mL separatory funnel and 25 mL
dichloromethane as the extracting solvent. The solution was then left to evaporate overnight in an
evaporating dish covered with a perforated bond paper. A yellow brown solid crude nicotine was
observed, yielding a 0.1904% crude nicotine from the tobacco leaves. Using 10 mL saturated ethanolic
picric acid, crude nicotine was precipitated into its less toxic derivative, Nicotine Dipicrate, which is
observed as a fluffy yellow precipitate and left to dry in an evaporating dish covered with a perforated
bond paper. The residue, observed as yellow crystals, was added and dissolvedin20 mL of 50% (v/v)
ethanol-water. The solution was then cooled and transferred into a test tube, where it was covered
with a bond paper and left to recrystallize. The now formed pure nicotine dipicrate took on the form of
brownish-yellow precipitates. The experiment aimed to isolate nicotine from tobacco leaves and
compute its percent yield, to convert crude nicotine to its dipicrate salt derivative, to recrystallize
crude nicotine dipicrate into its pure form, and to characterize and test for solubility the nicotine and
nicotine dipicrate.

INTRODUCTION
Nicotine is a poisonous volatile
nitrogen-containing alkaloid
predominantly found in tobacco leaves. It
has a chemical formula of C10H14N2 and is
assigned an IUPAC name of [1-methyl-2-
(3-pyridyl) pyrrolidine] based from its
nitrogen-containing base and two
heterocycles, pyridine and pyrrole [1]. It is
soluble in water and ethanol.
Fig 1. Structure of Nicotine
As a nitrogenous base, nicotine
forms salts with acids that are usually
solid and water soluble. In the experiment
crude nicotine is converted into its
derivative nicotine dipicrate because it is
less toxic. This was achieved by adding
ethanolic picric acid to the crude nicotine
to precipitate out impure nicotine
dipicrate.
Fig 2. Reaction of Nicotine to Nicotine
Dipicrate
The general objectives of the
experiment were to isolate nicotine from
dried to tobacco leaves using 5% aqueous
sodium hydroxide and further extract
nicotine from the alkaline extract using
dichloromethane, and determine the %
w/w yield of nicotine from the tobacco
leaves. The experiment also aimed to
precipitate nicotine by adding saturated
ethanolic picric acid subjecting it into
recrystallization. And lastly, to describe
observable physical properties of the
recrystallized products.
EXPERIMENTAL
A Compounds tested (or Samples
used)

In the experiment, 8.4048 grams of

dried tobacco leaves from Marlboro (red)
cigarette sticks were used.
 The crude nicotine that was isolated
from the tobacco leaves was then
converted to Nicotine Dipicrate, which
wasfurther used in recrystallization.
B Procedure
A clean and empty evaporating dish
was first weighed and tared. 8.0-8.5
grams of tobacco leaves was then weighed
and transferred into a 400 mL-beaker. 100
mL of 5% aqueous sodium hydroxide was
then added and the solution was stirred
for 15 minutes. After, the solution was
filtered with a cheesecloth, it was then
washed with 20 mL distilled water and
leached. The residue leaves were
discarded.
Next, the brown filtrate was
transferred to a 250-mLseparatory funnel
and extracted with 25 mL
dichloromethane. The contents of the
funnel was swirled and the bottom layer
was collected in a clean and empty
evaporating dish. Another 25 mL
dichloromethane was added to the funnel
and filtered again. The process was
repeated a third time. The evaporating
dish was then covered with a perforated
bond paper and set aside for the solution
to evaporate until the next laboratory
period.
The residue inside the evaporating was
identified as the crude nicotine and was
weighed to attain the %w/w yield of
nicotine from the dried tobacco leaves.
Afterwards, the crude nicotine was tested
for solubility in water by adding 1.00 mL
distilled water.
A 4.00 mL ethanol was added to the
dissolved crude nicotine and was filtered
into a 50 mL beaker using an ordinary
funnel with a small piece of cotton in the
apex. The funnel was then rinsed with an
additional 5 mL ethanol. 10 mL saturated
ethanolic picric acid was then added to
precipitate out Nicotine Dipicrate, the
solution was then transferred into a clean
evaporating dish and covered with
perforated bond paper then left to dry for
the next laboratory period.
Using a spatula the crystallized
residues formed, which was crude nicotine
dipicrate, were scraped from the sides of
the evaporating dish and 20 mL of 50%
(v/v) ethanol-water was added, for
recrystallization, to the evaporating dish
and heated, to dissolve the residues. The
solution was then cooled under running
water and transferred into a hard glass
tube, it was then covered by perforated
bond paper and set aside for the next
laboratory period.
The solution was allowed to decant
and then filtered by using an ordinary
funnel and a tared filter paper. The filter
paper containing the pure nicotine
dipicrate crystals was then dried in the
fume hood and then weighed.
RESULTS AND DISCUSSION
The experiment ended after
attaining all the necessary information and
data from the performed experiment. The
following data were obtained from the
isolation of crude nicotine from tobacco
leaves
Table 1. Weight of Tobacco and Nicotine
Weight (grams)
Weight of tobacco 8.4048 g
leaves used
Weight of 108.6033 g
evaporating dish
Weight of 108.6193 g
evaporating dish &
nicotine
Weight of nicotine 0.016 g
The extracted crude nicotine was a
yellow solid residue and soluble in water
and ethanol. Isolated crude nicotine was
achieved by means of multiple extraction.
The 5 % NaOH was added to the tobacco
leaves to create an alkaline extract
solution, it is used as a means to make
the sample into a liquid for easier
manipulation. In the experiment,
dichloromethane (DCM) was used as the
extracting solvent, although nicotine is
soluble in both, DCM was used rather than
chloroform because it is less toxic.
Separation was achieved by use of a
separatory funnel. Because 5% sodium
hydroxide and dichloromethane are
immiscible, the solutions will readily form placed on a hot plate. By cooling the
a partition in between the two solvents solution, the solution produce yellow-
when the two liquids are mixed in the brown prismatic crystals, identified as the
separatory funnel. Dichloromethane is less pure nicotine dipicrate.
dense than 5% NaOH, therefore it forms
the lower layer. Nicotine is soluble in the
dichloromethane therefore the lower layer
is collected. For better extraction yield
dichloromethane is added multiple times
hence the term multiple extraction
Percentage yield was attained by
dividing the weight of the tared
evaporating dish containing nicotine by
the weight of the dried tobacco leaves
used in the experiment multiplied by 100.
The percent yield computed was
Fig 5&6. Decanted pure Nicotine Dipicrate
0.1904%.
(left) and dried pure Nicotine Dipicrate on
Nicotine is liquid and the amount
filter paper
isolated is small and would be difficult to
manipulate and characterize, therefore the
nicotine will be isolated as its crystalline CONCLUSION
dipicrate salt, which is also less toxic. The formation of yellow-brown
Because nicotine has a nitrogenous base crystals or pure nicotine dipicrate indicates
when added an acid it becomes a salt. The the end of the experiment as the finally
crude nicotine was converted to its produce. The group was able to isolate
derivative, nicotine dipicrate, by means of nicotine from the dried tobacco leaves,
precipitation using ethanolic picric acid. perform multiple extraction, and compute
The precipitated crude nicotine dipicrate for the percent yield (w/w). They were
was observed to be a fluffy yellow further able to convert nicotine into its salt
amorphous precipitate, after being left to derivative by adding saturated ethanolic
dry it formed into yellow brown crystals. acid, and purifying it by means of
recrystallization. In conclusion, the group
was able to characterize and observe
physical properties of the products and
test solubility in ethanol and water.

REFERENCES

[1] No Author mentioned. Structure and

properties of Nicotine. Retrieved from
http://www.chm.bris.ac.uk/motm/nicotine/E-
propriete.html 05/01/17
Fig 3&4. Crude Nicotine Dipicrate
Precipitate (left) and Crude Nicotine [2] Retrieved from
Dipicrate dried and crystalized (right) [3] Retrieved from
[4] Retrieved from
Lastly, the crude nicotine dipicrate was
subjected to recrystallization with 50%
(v/v) ethanol-water as the recrystallizing
agent, it was found that this nicotine
derivative was only found to be soluble in
ethanol and water at high temperatures,
which is why while adding the
recrystallizing agent the solution was