Xennon Gubaton Locker no.

: 93
Joshua Guerra Section: CHEM 154L YB
Rogemar Jaraula Date Performed: November 21, 2018
Attendance:

Experiment 1: Isolation of Caffeine in Tea

V. DATA

PART A: Solid-Liquid Extraction

Description

Overall weight is 8.025 g. The appearance

Tea leaves ( Sir Thomas J. Lipton Black tea) is black fine tea. The smell is like a dried
leaves and coffee.

Sample mixture (water +anhydrous Na2CO3 The tea components slowly diffuse to the
and tea leaves) before boiling solution creating a brownish to black
mixture. There is a noticeable smell of
coffee and tea but not too strong.

Sample mixture after boiling Components of tea diffused to the solution,

creating a dark mixture with the strong
smell of a coffee and tea combined.

Residue There were black solid residues from the

tea bag. These residues are like dusts and
leave a coffee smell that is not too strong
and not too weak.

Filtrate The filtrate is so dark. The strong smell of

a coffee is very noticeable and not too
strong soothing smell of a tea.

Filtrate after boiling The filtrate is black in appearance and has

a very strong smell of coffee and tea.
Part B: Liquid-liquid extraction

Description

Building up of pressure causes a sound

Aqueous extract (filtrate) shaken with after opening the shaken mixture. The
extracting solvent (12 ml Methylene chloride) dark color of the mixture slowly becomes
lighter. After mixing and shaking, Clear
globules are forming.

Mixture upon standing a. It is brown in regions in between the

aqueous and organic phase. It is black
a. Aqueous phase in the upper part of the surface.

b. It appears to lose its color, producing a

clear solution.
b. Organic phase

Combined organic phase plus drying agent The bits of tea leaves residue in the
organic phase included in the organic with
some of the liquid solution were clumping
into a more compact solid, forming
bits/chunks of crystals. The solution
became clearer than it was extracted from
the separatory funnel. After a while, the
solution became cold.

Residue The residue was solid, accumulated from

the compound and transparent.

Filtrate (dried CH2CL2 extracts) White fine dusts with greenish specks
were observed in some regions of the
container. Odourless.

Yield of Crude Caffeine from Tea Leaves

Mass (g)
Tea Leaves Crude Caffeine
Material + Container 101. 9 41.70
Empty container 93.92 42.16

Material 8.025 0.4600

% Recovery of Crude caffeine=

= 5.73 %

Part C: Sublimation from a Crude Caffeine

Description

Original crude caffeine White fine dusts with greenish speck were
observed in some regions of the container.
Odourless.

Sublimate on collection surface (pure caffeine) White small crystals are observed on the
After (11:38) minutes surface.

Residue There are roasted-like residues found in

the container that has a coffee like smell.

Recovered Pure Caffeine from Crude Caffeine

Mass (g)
Crude Caffeine Purified Caffeine
Material + Container 48.70 N/A
Empty container 42.16 N/A
Material 6.540 N/A

Percent Purity: N/A

Post Lab Questions

1. What components of tea leaves were separated during solid-liquid extraction?

- Solid-liquid extraction isolates the natural products from its biological source,
which for this experiment is the tea leaves. Caffeine is the main substance
extracted during the solid-liquid extraction. Alongside with it are the tannins,
gallic acids, flavonoid pigments and other substances.

2. How would you prove that the CH2CL2 layer is below the water layer during liquid-
liquid extraction?

- The liquids involved have to be immiscible in order to form two layers upon
contact. Since most of the extractions are performed using aqueous solutions,
the miscibility of the solvent with water is a crucial point as well as the
compatibility of the reagent with the compounds and the solvent of the
solution to be extracted. The solution with the lower density will rest on top,
and the denser solution will rest on the bottom. Methylene Chloride (CH2CL2)
has greater density which 1.33 g/ ml compared to water which is only 0.998 g/
ml. Thus, we could say that the one above is water while the one under is the
CH2CL2.

3. Indicate at least three properties which a compound must possess in order for it
to function well as an extraction solvent?

- Polarity of solvent.
- Unreactive with solute molecules.
- Less boiling point compared to solute i.e. easy to be separated out.
- Solubility
- Volatility of the solvent

4. Using the distribution coefficient, show by calculation why several extractions

with small amount of extracting solvent is more efficient than one with an equal
amount of solvent.
- The distribution between both solvents is dictated by the partition
coefficient, K of A between the two solvents. The partition coefficient is the
equilibrium constant for the distribution of a solute between two immiscible
layers.

By equation:

Thus, we can say that if we increase the amount of the solvent with a
constant amount of solute, the amount of extraction will be less. If we
decrease the amount of solvent on the other hand, the extraction will be more
efficient because the extraction is more.
 5. What limitations are commonly encountered in the application of sublimation as a
general method of purification?

- Sublimation as a general method of purification, it is not as selective as

crystallization, it typically requires a vacuum and usually requires that the
compound you are trying to separate is volatile, while everything else is not
volatile in order to separate the impurities.
-
6. Compare the material remaining in the evaporating dish that which was sublimed
and the original crude caffeine.

- The sublimed crude caffeine where formed into crystals from gas while the
crude caffeine already evaporated and only bits of fine white-greenish dusts
are available in the crucible.

ANALYSIS

Extraction is the process of selectively separating organic compounds from a certain

matrix. It involves two distinct procedures: Solid-liquid extraction and Liquid-liquid extraction. In
the solid-liquid extraction, containing the solute, is dispersed in the solvent and mixed. The
solute is extracted from the solid phase to the solvent, and the solid phase is then removed by
filtration. In the liquid-liquid extraction, a solute is separated between two liquid phases, typically
an aqueous and an organic phase. In the simplest case, three components are involved: the
solute, the carrier liquid, and the solvent. The denser part settles at the bottom of the separatory
funnel while the one with lower density settles on the top of the solution.

Tea leaves is great source of caffeine as the Caffeine can be steeped from the Tea
Leaves with very few other interfering compounds. The caffeine is so isolated that it can be
separated from tannins that is also one of the major components in tea forming organic
compounds.

The solid-liquid extraction process made use of Sodium Carbonate. It places

caffeine in a more basic environment so that it has a higher affinity for Methylene
Chloride and to cause the tannins to form phenolic salts in the aqueous solution. It also
converts tannins and gallic acid to sodium salts which are soluble in water so that
later on, lesser impurities will be encountered.

The addition of Methylene Chloride in the liquid-liquid extraction permitted the

formation of two immiscible layer: an organic and aqueous layer. Caffeine is in a polar
substance, but its polarity was decreased significantly when it was exposed to a basic
solution. Therefore, it became a soluble in Methylene Chloride and suspends in the
organic layer. As an alkyl halide, Methylene Chloride is denser compared to water, thus
it settles at the bottom of the separatory funnel.
 The drying agent which is the anhydrous sodium sulfate was added to the
organic phase. This is because Methylene Chloride did not only dissolved the caffeine
but also the water. It was added to remove excess water so that by the time of
purification, pure caffeine will be obtained at room temperature.

The sublimation part, which is the last part of the experiment, was necessary to
get the pure caffeine in the experiment. Sublimation is a process used to isolate a -
natural product from other undesired compounds, and then purify it by a direct phase
change of that product from a solid to a vapor.

From the experiment, the percent crude caffeine collected is 5.73 %. The
greenish specks appearanceof crude caffeine is due to the presence of chlorophyll. The
calculation for the percent purity was not attained due to the small amount of crystals
collected during the sublimation part. The presence of the caffeine crystals collected in
the sublimation part were too little that could be negligible at a larger scale.
Nonetheless, the experiment confirmed that there really is a presence of caffeine from
the sample tea.

The negligible amount of caffeine collected might be due to the significant loss of
the product throughout the procedure. A loss of product could have been because of the
formation of emulsions while shaking the solution in during the liquid-liquid extraction.
Another would be the non-thoroughly washing with dichloromethane to extract as much
caffeine as possible. Too much of transfer of the mixture would indicate also many
opportunities of the loss of the products. Lastly, the concentration of caffeine might not
have had been high enough because of the addition of too much water.

Conclusion

The collected crude caffeine was 0.4600 g of which is 5.73 % of the initial weight
of the tea leaves. The total percent purity was not obtained due to the negligible amount
yield in the sublimation process. The efficiency of the extraction cannot be transcribed
due to the lacking percent purity.
References:

Amrita University. Extraction of Caffeine from Tea. 2013.retrieved from http://amrita.vla

b.co.in/? sub=3&brch=64&sim =169&cnt=1

Postu, A. and Wilson, S. (2013). Isolation of Caffeine from Tea Leaves via Acid-Base
Liquid-Liquid Extraction. https://edspace.american.edu/ap7794a/wp-
content/uploads/sites/159/2015/03/Isolation-of-Caffeine-from-Tea-Leaves-
via-Acid-Base-Liquid-Liquid-Extraction.pdf

UCSC (2012) . Experiment 3 – Isolation and Sublimation of Caffeine from Tea Leaves
https://cpb-us-e1.wpmucdn.com/sites.ucsc.edu/dist/9/291/files/2015/11/Exp-
3-Isolation-and-Sublimation-of-Caffeine-from-Tea-Leaves.pdf

UCDAVIS ChemLibretext.org (2016). Liquid-liquid extractions. https://chem.libretexts.o

rg/LibreTexts/Northeastern/07%3A_Collecting_and_Preparing_Samples/7.7
%3A_Liquid%E2%80%93Liquid_Extractions

Williamson, K and Katherine Masters (2011) . Macroscale and Microscale Organic

Experiments, 6th ed.; Brooks/Cole,.
References:

Distillation of Liquids: Separation of 2-Propanol from Water by Fractional Distillation

(n.d). retrieved from http://jabjorklund.faculty.noctrl.edu/chm114/lab/1_
distillation.pdf

Chem 123 Experiment 2 Distillation (2009). Retrieved from http://chemistry.bd.psu.

edu/halmi/chem 213distillf09.pdf

Experiment 7- Distillation (2013). Retrieved from http://learning.hccs.edu/faculty

/paul.clemens/copy4_of_chem2423-1/laboratory-manual-provided-as-
handouts/experiment-7-distillation-2013-separation-of-a-mixture