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Exer 2 Postlab Discussion

IV. Data (revised)


Table 2.1. Observations on the isolation of crude piperine.
Reagent/Action
Observations
black peppercorn
black coarse solid with a pungent
odor
addition of 95% ethanol
dark green mixture with black solids
at the bottom
after reflux
formation of two layers (brown-black
solution at the top and black solids at
the bottom)
after filtration A
filtrate A
brown-black solution with a pungent
odor
residue A
black coarse solid with a pungent
odor
after distillation
distillate
clear solution with a pungent odor
residue
dark brown solution
after cooling to room temperature
addition of 10 % ethanolic KOH
solution
after mixing thoroughly for 5 minutes
after filtration B
filtrate B
dark brown solution
residue B
fine black powdery solid with a
pungent smell
addition of 100 mL of NaCl solution
coffee-like mixture and formation of
and 100 mL distilled H2O
precipitates
after standing for 10 minutes
formation of two layers (light brown
solution at the top and brown
precipitates at the bottom)
after filtration C
filtrate C
light brown solution
residue C
light brown powdery solid
Table 2.2. Observations on the purification of crude piperine.
Reagent/Action
Observations
crude piperine
light brown solid
after dissolution with acetone
yellowish-brown mixture with few
precipitate at the bottom

after heating
after filtration
filtrate
residue
after cooling

yellow-brown solution
yellow solution
light brown solid
yellow-brown solid

Table 2.3. Solubility of aspirin in different solvents at varying temperatures.


Aspirin +
Reagent/Action
Aspirin + H2O
Aspirin + CH2Cl2
Methanol
At room
clear mixture
light yellow
clear
temperature
Mixture
with presence of
homogenous
homogenous
description
white precipitate
solution
solution
at the bottom
+
+
Solution (+/-)
With hot solvent
Mixture
white turbid
------description
mixture
Solution (+/-)
+
Resulting crystal
Size
medium-sized
fine
fine
Color
white
white
light yellow
Crystal form
irregular-shaped
flake-like
irregular-shaped
* Benzoic acid was used instead of aspirin and ethanol was used to replace
methanol.
Table 2.4. Observations on the recrystallization process of aspirin.
Reagent/Action
Observations
crude aspirin
white tablet
after dissolution with hot solvent
white turbid mixture
(H2O)
after reheating
white mixture with few white
precipitates at the bottom
filtration A
filtrate A
dull white mixture
residue A
white powder
after cooling to room temperature
dull white mixture
after crystallizing
dull white mixture with white
precipitate at the bottom
filtration B
filtrate B
dull white solution

residue B
white powder
*Aspirin tablet was used instead of crude aspirin.
Table 2.5. Melting point determination of piperine using oil-bath method and
Fisher-Johns melting point apparatus.
Parameter
Melting Point Observed
oil-bath method
temperature when melting starts
(C)
temperature when melting
completes (C)
melting point range (C)
observations while heating
Fisher-Johns melting point apparatus
temperature when melting starts (C)
106 C
temperature when melting
110 C
4 C
completes (C)
melting point range (C)
observations while heating
Table 2.6. Reaction of crude piperine to concentrated acids.
Sample
Observations
crude piperine + HCl
yellowish solution
crude piperine + HNO3
yellowish solution
crude piperine + H2SO4
reddish black solution
Table 2.7.
Mass (g)
black peppercorns
container + sample
empty container
sample
crude piperine
container + sample
empty container
sample
purified piperine
container + sample
empty container
sample
crude aspirin
container + sample
empty container
sample
purified aspirin

% yield

19.102
4.103
14.999
3.56%
0.258
2.12%

50.199
49.998
0.201

container + sample
empty container
sample

1.493
1.380 g
0.113 g

VI. Discussion
Piperine, piperanine, and piperettine are common alkaloids that make
up 5-9% of ground black pepper. These alkaloids, which are naturally
occurring chemical compounds, can be extracted from black pepper in the
presence of ethanol and KOH (Epstein, 1993). Black pepper is composed of
moisture, protein, sugar, amylose, and ash. It is one of the many peppers
that aid in digestion, help balance a diet, and act as natural painkillers.
Peppers also activate taste receptors associated with appetite. Piperine is an
alcohol-soluble alkaloid responsible for monoclinic needles and the pungency
of black pepper. It is composed of lignans, alkaloids, and oils. It has a variety
of important biological properties, such as anti-antigenic and anti-cancerous
properties, which prevent the formation of blood vessels that can potentially
feed oxygen to cancerous tissue. Piperine also has anti-depression like
activity, and exhibits cognitive enhancement in some cases. Lastly, piperine
is been shown to stimulate anti-inflammatory responses, as well as skin
pigmentation (Raman, 2002).

Naturally extracted drugs are often used in both pharmaceuticals and


medicine. Extracted products that contain healing agents tend to be found in
natural sources such as microbes and plants. Scientists have found abundant
evidence that nature is a potential source for extraction of a large range of
therapeutic agents. Using techniques such a chromatographic fractionation,
the active therapeutic component in natural extractions can be identified
(Hong-Fang, 2009). One common natural extraction is isolation of piperine
from black pepper. During this isolation, ground black pepper was refluxed

with 50 mL of ethanol in the presence of heat. After vacuum filtration, the


liquid filtrate was evaporated with a nitrogen stream and the oil residue was
dissolved in 12.5 mL of 10 % KOH in ethanol. 100 mL of water was slowly
added to the warm solution until a yellow precipitate began to form. After
vacuum filtration isolated the yellow crystals, recrystallization yielded pure
piperine product (Raman, 2002).
Isolation of Crude Piperine
The isolation of crude piperine by solid-liquid extraction was carried out
in a reflux setup consisting of a round bottom flask connected to a
condenser; 14.999 grams of freshly ground peppercorns were transferred
into a round-bottom flask. Freshly ground peppercorns were used to yield
consistent and accurate results for the final product of piperine. Boiling chips
was also added beforehand to promote bubbling and keep the liquid from
superheating and flying out of the flask (bumping) (Zubrick, 2011). Then, 150
mL of 10% of 95% ethanol was used as the extracting solvent for the
extraction of piperine when undergoing a reflux. 95% of ethanol, a good
extracting solvent for piperine, was used because piperine is as polar as
ethanol, and it is soluble in ethanol at its boiling point. Also, ethanol does not
react with piperine and it boils at 78.7C which is high enough to cause the
desired reaction of the ethnol and peppercorns (piperine). This reflux served
to pull the piperine from the pepper grounds into solution. Many other
components of black pepper, such as the lignans and flavonoids are less
polar then piperine and do not move into the ethanol solution. Following
reflux, these less polar compounds were removed by distillation. Reflux
allows the solution to be boiled and the vapors to condense that enable the
return of the condensate to the reaction flask. Upon increase of temperature,
the organic compound of piperine was dissolved in the organic solvent
ethanol. During reflux, the loss of solvent containing those organic
compounds was minimized. One can see the upper limit traveled by the
vapors as sort of a "mirage," called the reflux ring, and caused by a
difference in the index of refraction for air versus the ethanols vapor (Straus,

2002). The flask was not more than half-filled to allow for enough room
during expansion and/or boiling (Straus, 2012). During the reflux, the stopper
was not put at the tip of the reflux condenser and the water inside it was
maintained to cool temperature. The inlet of the water was on the lower end
of the condenser, the outlet at the upper end independent if the condenser
was used for reflux or distillation. In this way, a low flow rate of the water will
be sufficient for the cooling because the outer jacket of the condenser will fill
up with water first before it reaches the outlet (Straus, 2012). After the reflux
for two hours, there were two layers formed inside the round-bottom flask, a
brown-black solution at the top and black solids at the bottom. The mixture
was cooled to room temperature and filtered through suction filtration to
remove the unnecessary peppercorns which will not be used in further
distillation.
peppercorns + ethanol
The filtrate from the reaction mixture from reflux undergone distillation
for further purification. Unlike reflux, in distillation, a liquid is heated until it is
boiling. The vapor which is produced is condensed and collected in a
separate flask. In reflux, the liquid is boiled, but the vapor is allowed to
condense and flow back into the original flask. Collecting the condensed
vapor in a second flask allows separating out the individual components of
the mixture by distillation (Zubrick, 2011). Allowing the condensed vapor to
flow back into the original reaction flask, allow dissolving hard the
undissolved compounds by reflux. This continual recycling of the solvent
helps drive the reaction to completion. Distillation was done to separate the
concentrated mixture of piperine, chavicine, and other components to the
solvent, ethanol (Gaikar, 2010). Also, the precipitation of piperine in the
further process will be fastened.
product -> piperine + chavicine + other components
Raoults law applies to the concept of simple distillation. This law
states in an ideal solution, the partial vapor pressure of a component in a
mixture is equal to the vapor pressure of the pure component at that
temperature multiplied by its mole fraction in the mixture (Clark, 2014).

Therefore, for two liquids at the same temperature; the one with the higher
vapor pressure, 95% ethanol, is the one with the lower boiling point. Simple
distillation will be used to separate 95% ethanol (boiling below 150C at 78.3
C at 1 atm) from the remaining nonvolatile impurities of piperine and the
other 5% water that boils at least 25C higher than ethanol (at 100 C)
(Zubrick, 2011).
PT = PA + PB
= XAPoA + XBPoB
A reflux setup includes a round bottom flask connected directly to a
condenser, whereas in a distillation, the round bottom flask is connected to a
y-adapter. The round bottom flask should be 50-75% full to prevent losing
the product when it is 33% full and throwing up of undistilled material into
the condenser if it is more than 75% full (Zubrick, 2011). Boiling chips was
added. The side arm of the y-adapter connects to the condenser. The
condenser connects to a receiving flask through a vacuum adapter. The
receiving flask will be placed under an ice water bath. Vapor passing through
the plastic tubing will condense immediately when it comes into contact with
the cooler air of the receiving flask (Gaikar, 2010). Lastly, the thermometer
bulb is placed below the side arm of the three-way adapter (about 5 mm) to
obtain the correct vapor temperature while distilling. If not, then there will a
chance that the determined vapor temperature is higher (lower than 5 mm)
or lower (higher than 5 mm). About 1 to 2 drops of distillate per second was
maintained to sustain the separation process (Epstein, 1993).The distillation
was stopped when the volume of the mixture is reduced to about 5 to 10 mL.
The distillate was then transferred into a bottle labeled as recovered
ethanol.
st
The crude extract obtained by heating black pepper in ethanol also
contains some acidic, resinous materials that must not be allowed to
precipitate with and therefore contaminate the piperine. In order to prevent
co-precipitation of piperine and the resin acids, dilute ethanolic potassium
hydroxide is added to the concentrated extract to keep acidic materials in

solution as their potassium salts (Clark, 2014). This treatment would yield
piperic acid and piperidine. The mixture was stirred and filtered the warm
mixture to remove any insoluble materials. 250 mL of water and 100 mL of
NaCl solution was added into the filtrate to precipitate out crude piperine
from the solution (Epstein, 1993). This will displace the ethanolic KOH
solution from being a solvent because ethanolic KOH is more soluble in water
while piperine is not. This will yield a metallic yellow precipitate identified as
crude piperine. The mixture was stand for 10 minutes, was filtered, and was
dried under the fumehood to acquire to crude piperine which will be used for
recrystallization.

Recrystallization of Piperine
Recrystallization is used in solids for purification to ensure that the
product is free from contaminants. The crude piperine is dissolved in
minimum amounts of acetone for recrystallization. Piperic acid would react
with acetone, yielding purified piperine as the final product. The final product
was flaky yellow crystals which is consistent with the literature for this
experiment. It could also be concluded that piperidine may have been
removed by the addition of acetone because of the lesser peppery odor of
the purified piperine (Gaikar, 2010).
Black peppercorns contain piperine (3-9%), volatile oil (1-2.5%),
pungent resin (6%), piperidine and starch (30%). The percentage yield of
crude piperine is 4.56%. On the other hand, the purified piperine has a
percentage yield of 3.12%. Crude piperine has a higher percentage yield
than purified piperine due to the contaminants (excess products or solvents)
present in it unlike the purified piperine which undergone the purification
process.

Aspirin is most widely sold over-the-counter drug. It has the ability to


reduce fever (an antipyretic), to reduce pain (an analgesic), and to reduce
swelling, soreness, and redness (an anti-inflammatory agent) (Los Angeles
City College, 2005). Aspirin, known chemically as acetylsalicylic acid, is a
white solid derived from salicylic acid which occurs naturally in the bark of
willow trees. Salicylic acid contains two acidic functional groups, a carboxylic
acid and an a phenol group.

Recrystallization of Aspirin
Selection of a solvent for recrystallization
The choice of solvent is perhaps the most critical step in the process of
recrystallization since the correct solvent must be selected to form a product
of high purity and in good recovery or yield. The recrystallization of aspirin
has begun with the selection of an appropriate solvent for recrystallization.
First, a clear homogenous solution was formed upon mixing 0.5 mL methanol
to a spatula tip of aspirin. Next, aspirin and dichloromethane yielded a light

yellow homogenous solution. Aspirin is an organic acid; therefore, it is


soluble in an organic solvent (dichloromethane), but will react with a basic
reagent such as methanol to produce the conjugate base of the acid. The
conjugate base is a salt and is water soluble; therefore, it is removed from
the organic solvent layer. Re-acidification of this basic aqueous layer will
regenerate the organic acid, which will precipitate from the aqueous solution
due to the acid's limited solubility in water.
aspirin + meoh
aspirin + CH2CL2
A clear mixture with presence of white precipitate at the bottom was
formed upon addition of 0.5 mL water to a spatula-tip of aspirin. Aspirin is
only slightly soluble in water because it contains polar functional groups
which can form hydrogen bonds with polar water molecules. When aspirin
ages, it gradually reacts with absorbed moisture from the air and partially
reverts back to salicylic acid and acetic acid. In general, it's the above
reaction run backwards (NST, 2011). It is the acetic acid that smells like
vinegar. However, after the aspirin and water was boiled to test its solubility,
aspirin did completely dissolve in water, forming white crystals when all the
water molecules evaporate. For some time, some hydrolysis will occur more
rapidly and it will partly decompose to salicylic acid and acetic (ethanol) acid
again. That is why most modern-day aspirin tablets are coated with a
substance that keeps moisture away from the active ingredient (NST, 2011).
As a result, they last a long time. The synthesis reaction of aspirin is shown
below:
aspirin
(acetylsalicylic acid)

+ water

+ H2O(l)

salicylic acid

acetic acid
(ethanoic acid)

CH3COOH(aq

Therefore, water is considered as a good recrystallizing solvent


because it dissolves the aspirin at elevated temperature and only sparingly
soluble in the solvent at room temperature. This difference in solubility at hot
versus cold temperatures is essential for the recrystallization process. If the
compound is very soluble in the solvent at room temperature, then getting
the compound to crystallize in pure form from solution is difficult. Second,
the unwanted impurities should be either very soluble in the solvent like
water at room temperature or insoluble in the hot solvent. This way, after the
impure solid is dissolved in the hot solvent, any undissolved impurities can
be removed by filtration. After the solution cools and the desired compound
crystallizes out, any remaining soluble impurities will remain dissolved in the
solvent. The boiling point of water is less than the melting point of aspirin. If
it is not, oil would be obtained rather than crystals. Next, water does not
react with the aspirin being purified. Aspirin may be lost during
recrystallization if the water reacts with the compound. Lastly, water was
volatile enough to be easily removed after aspirin has crystallized. This
allows for easy and rapid drying of the solid aspirin compound after it has
been isolated from the solution
(https://www.erowid.org/archive/rhodium/chemistry/equipment/recrystallizati
on.html).
Recrystallization Process
Commercial aspirin (substitute to crude aspirin) was dissolved in
minimum amount of hot water, the selected solvent for recrystallization. As
water is cooled, the impurities must stay soluble while the compound of
interest precipitates. It is important that minimum amount of hot solvent will
be used that will just dissolve the compound of interest to prevent its lower
recovery and degree of unsaturation (Sneling, 2004). A small amount of
decolorizing carbon was added if the resulting solution is highly colored.
Decolorizing carbon, also called activated charcoal, is finely divided carbon
often used to decolorize a solution. The small particles of decolorizing
carbon provide a large surface area to which large colored molecules may

become adsorbed (Los Angeles City College, 2005). Adsorption is the


binding of molecules or particles to a surface which must be distinguished
from absorption, the filling of pores in a solid (Los Angeles City College,
2005). However, the amount of decolorizing carbon is maintained. If not,
excessive loss of the desired product will happen.
Gravity filtration is normally used to remove unwanted solids from a
desired solution. In contrast, to collect a solid product, the usual choice is
suction filtration (http://www.chemistry.sjsu.edu/straus/FILTRATION
%20htms/GravFilt.htm). In both processes the solution passing through the
filter is called the "filtrate." A fluted piece of filter paper was placed inside a
stemless funnel. A short-stemmed or stemless glass funnel should be used to
minimize crystallization in the funnel, and using fluted filter paper will
minimize crystallization on the filter (Yoder, 2015). The set up hot must be
kept hot to prevent crystals from forming prematurely. At these cooler
temperatures, crystals are likely to form. If the funnel was properly heated
before filtration, all of the solution will have passed through and no crystals
will have formed on the paper or in the funnel. If crystals have formed,
pouring a small amount of boiling solvent through the funnel will dissolve
these (Yoder, 2015). Afterwards, the filtrate was cooled to room temperature
to enable the recrystallization of aspirin. Gradual cooling is conducive to the
formation of large, well-defined crystals. After a while, crystals should appear
in the flask. However, no crystals have formed so a stirring rod was used to
scratch the bottom of the flask. This will produce sites of nucleation. To
maximize the yield, the flask was placed in an ice bath to finish the
crystallization process. The crystals were finally collected using suction
filtration. They were put in a watchglass and were allowed to air dry in the
fumehood. After removing all the crystals from the filter paper, the filter
paper was removed and was scraped to acquire any remaining crystals from
the funnel. Spreading the crystals out in a beaker or a crystallizing dish will
provide for the most efficient drying as the crystals will have a maximum of
exposed surface area. After drying, percentage yield was obtained.

st
Crystals will not form if there is a large excess of solvent. If no crystals
form with the methods already discussed, a portion of the solvent may need
to be removed. This can be accomplished by heating the solution for a period
of time in order to evaporate some solvent. The new, concentrated solution
should be cooled, and the previously mentioned methods to stimulate
crystallization should again be attempted.
Another potential problem in recrystallization is that the solute
sometimes comes out of solution in the form of impure oil instead of forming
purified crystals. This usually happens when the boiling point of the solvent
is higher than the melting point of the compound, but this is not the only
scenario in which this problem presents itself. If this begins to happen,
cooling the solution will not stimulate crystallization, it will make the problem
worse. If oil begins to form, heat the solution until the oil portion dissolves
and let the whole solution cool. As the oil begins to form again, stir the
solution vigorously to break up the oil. The tiny beads of oil that result from
this shaking may act as the nuclei for new crystal formation.
Characterization of Piperine
Melting Point Determination
A melting point is the temperature at which the first crystal just starts
to melt until the temperature at which the last crystal just disappears
(Zubrick, 2011). In this point, the solid and liquid phases coexist are in
equilibrium at 1 atm. Thus the melting point (abbreviated mp) is actually a
melting range. Even after a solid has been recrystallized, it may still not be
pure. Thus, it is important to determine the purity of the sample, and one of
the easiest methods to do this is by determining the melting point of the
solid. Melting point determination defines the purity (less than 1C), and
serves as identification and characterization of the sample. When a sample is
pure, the temperature remains constant during the whole process of
solidification and it requires certain amount of heat to break its

intermolecular forces of attraction (Gaikar, 2010). The characterization of


piperine involves the use of melting point determination.
In oil bath method, few crystals of the compound are placed in a thinwalled capillary tube 10-15 cm long, about 3-5 mm inside diameter, and
closed at one end. The capillary, which contains the sample, and a
thermometer are then suspended so they can be heated slowly and evenly.
The temperature range over which the sample is observed to melt is taken
as the melting point. The thermometer and the sample must be at the same
temperature while the sample melts, and so is the heating as the melting
point is approached should be slow. If the approximate temperature at which
the sample will melt is not known, a preliminary melting point determination
is determined by allowing the temperature of the sample to rise quickly
(Gaikar, 2010).
Fisher-Johns melting point apparatus is a quick and easy method to
determine the melting point of a solid wherein a small amount of crystal of
the sample was heated between a pair of microscope cover glasses on an
electrically heated metal block while observing the crystals with the aid of a
magnifying glass. It is more convenient because this method requires as little
as a single crystal.
The recovered sample in the Fisher-Johns method has a melting point
range of 4C. Although there should be a single temperature at which a pure
solid and a liquid are in equilibrium, most samples appear to melt over a
small temperature range. This happens because, with block melting points,
the temperature of the block rises a little during the time it takes the sample
to melt. The presence of impurities in the sample also caused the sample to
melt over a range of temperatures. Lastly, the usage of filter paper prior the
melting point determination caused contamination of the purified sample
since it contains cellulose that may end up in the tube along with the sample
and affects the melting point range of the piperine (Raman, 2002). Thus, a
sharp melting point (actually, a melting range of less than about 1C) is often
taken as evidence that the sample is fairly pure, and a wide melting range is
evidence that it is not pure.

Reaction with Concentrated Acids


Crude piperine is a very weak base, and its salts are decomposed by
water. Crude piperine reacts with concentrated hydrochloric acid forming a
yellowish solution. The color of the formed solution is also the same with the
addition of concentrated nitric acid in crude piperine. However, a reddish
black solution is formed by the addition of concentrated sulfuric acid to crude
piperine. Since piperine is known as a weak base, it reacts with concentrated
strong acids like HCl and HNO3 to form water and salt. This shows that the
acquired substance is piperine because it has reacted to these strong acids.
C17H19NO3 + H+ -> H20 +
C17H19NO3 + H+ -> H20 +
VII. Summary and Conclusions
Extraction from natural products is an important practice in chemistry
because it is the source of many medicinal and pharmaceutical compounds.
Black pepper itself has many important biological properties including
analgesic effects and anti-cancer effects. To gain a better understanding of
these effects, it is necessary to study the components which make up black
pepper. Piperine can be obtained from two different sources, synthetic and
natural. Isolating piperine from black pepper was done by reflux with
95%ethanol and precipitation with 10% ethanolic KOH. Reflux and distillation
are two chemistry lab techniques which involve boiling and condensing of a
solution. Reflux helps complete a reaction and distillation separates
components of a mixture. In distillation, a liquid is heated until it is boiling.
The vapor which is produced is condensed and collected in a separate flask.
In reflux, the liquid is boiled, but the vapor is allowed to condense and flow
back into the original flask. Raoult's law applies the conpect of simple
distillation. This states that the vapor pressure of a solvent above a solution
is equal to the vapor pressure of the pure solvent at the same temperature
scaled by the mole fraction of the solvent present. Crude piperine has a
higher percentage yield than purified piperine due to the contaminants

(excess products or solvents) present in it unlike the purified piperine which


undergone the purification process.
Piperine was purified by recrystallization using acetone.
Recrystallization, also known as fractional crystallization, is a procedure for
purifying an impure compound in a solvent. The method of purification is
based on the principle that the solubility of most solids increases with
increased temperature. The identity of the product is determined using
melting point determination through oil-bath method and Fisher-Johns
melting point apparatus. Melting point determination defines the purity (less
than 1C), and serves as identification and characterization of piperine. The
melting point range of the purified piperine was compared to the literature
value and it showed that the purified sample is logically far (4C) to the
literature value because of its wide range.
Purified piperine was also reacted with concentrated acids such as HCl,
H2SO4, and HNO3. Concentrated hydrochloric acid and nitric acid both
yielded yellow solution. On the other hand, sulfuric acid with piperine formed
a reddish black solution. This shows that the acquired substance is piperine
because it has reacted to these strong acids.
As an additional procedure aspirin was also recrystallized.
Acetylsalicylic acid, also known as aspirin, is one of the most widely used
medications to reduce fever and is also used as a pain killer. It is an acetyl
derivative of salicylic acid. It is a white, crystalline, weakly acidic substance
which melts at 140C. First, water dichloromethane, and methanol were
tested with crude aspirin to determine which the appropriate solvent for the
recrystallization process. Water is the appropriate solvent for aspirin
because its boiling point is lower than the melting point of aspirin, it has
dissolved aspirin at an elevated temperature, it is volatile, and it did not
reacted with aspirin. Recrystallization was done by hot gravity filtration.
Gravity filtration is used to remove the unwanted solids from a desired
solution. On the other hand, suction filtration is used to collect a solid
product.

In conclusion, piperine was unsuccessfully isolated with high purity.


There were no crystals formed after cooling the crude piperine so the oil bath
method was not executed. This may be due to the pressure buildup during
distillation (with more than 2-3 drops of distillate per second) since this will
poorly separate the residue and distillate. Also, during the recrystallization of
crude piperine, some of the purified piperine may be lost due to inadequate
washing of the residue. The sources of error in the recrystallization of aspirin
were the large excess of solvent which will result to no formation of crystals
or erroneous hot gravity filtration where the crystals may be left on the filter
paper.

VIII. References
Archive, C. (w.p.). Proper purification of crystalline solids. Retrieved on
September 12, 2015, from Recrystallization technique:
https://www.erowid.org/archive/rhodium/chemistry/equipment/recrystal
lization.html
Clark, J. (2014). Ideal mixtures. Retrieved on September 12, 2015, from
Raoult's law and ideal mixture of liquids:
http://www.chemguide.co.uk/physical/phaseeqia/idealpd.html
Epstein, W. (1993). Isolation of piperine from black pepper. American
chemical society, 598-599.
Gaikar, V. (2010). Separation science and technology. Extraction of Piperine,
3097-3099.
Hong-Fang, J. (February 20, 2009). Natural products and drug discovery.
Retrieved on September 12, 2015, from NCBI:
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2658564/
Los Angeles city college, 2. (2005). Synthesis and analysis of aspirin.
Retrieved on September 12, 2015, from Chemistry 51: Experiment 11:
http://www.csun.edu/~alchemy/Chem51-LACC/Labs/C51F07L12.pdf

NST. (2011). Aspirin. Retrieved on September 12, 2015, from Material


measurement laboratory: http://webbook.nst.gov/cgi/cbook.cgi?
ID=C50782&Type=THZ-IR-SPEC&Index=0
Raman, G. (April 17, 2002). Microwave-assisted extraction of piperine from
Piper nigrum. Retrieved on 12 September, 2015, from Industrial &
engineering chemistry research:
http://pubs.acs.org/doi/abs/10.1021/ie010359b?journalCode=iecred
Sneling, C. (June 6, 2004). Recrystallization. Retrieved on September 12,
2015, from
http://www2.volstate.edu/chem/2010/labs/recrystallization.html
Straus, D. (2002). Reflux. Retrieved on September 12, 2015, from
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IX. Remarks
A possible improvement could be made to the experiment to improve the
percentage recovery of the piperine is by increasing the time the black
pepper is refluxed to more precisely distill the mixture. Also, each substance
must be carefully quantitatively transferred to another container to prevent
the loss of important components in the mixture. Lastly, concentrated H3PO4
may be used to characterize piperine because allows direct determination of
piperine from pepper (Sneling, 2004).