Chemistry

Internal Assessment

Topic: ‘’Investigating the relationship between the charge density of salt ions
and the partition ratio for caffeine through the method of extraction’’
Table of contents:

- Introduction………………………………………………………………………….3

- Research Question……………………...…………………………………………3

- Background Knowledge……………………………………………………………4

- Experimental method and Procedure…………………………………………….6

- Results………………………………………………………………………………11

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Introduction:

As an IB student, I encountered difficulties when it comes to our final exams period.

Going through all the assignments and school activities connected to my IB exams

during this world pandemic, was honestly one of my biggest challenges that I had to

face this year. Instead of spending quality time on discussing school problems with

my teachers, I was limited by the pandemic and as a result I was obliged to solve

problems on my own. Since we have online school, I faced difficulties with organising

my time, therefore I spent countless nights sleepless and tired in order to complete

all of my assessments. Due to my stress and pressure to complete all of the tasks,

instead of sleeping, I was drinking coffee and studying. Because of the increased

amount of coffee I was drinking, I was triggered to explore and investigate the

amount of caffeine I was consuming. Through this assessment, through the process

of extraction of the caffeine, I would like to discover the perfect amount of caffeine in

order to be productive and concentrated, but at the same time to consume healthy

amounts of caffeine that wouldn’t harm my health.

Research question:

What effect does charge density of the salt ions has on the partition ratio for caffeine

extraction in water with different solvents?

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Background knowledge:

Caffeine (C8H10N4O2) 1is a bitter, white, crystalline methyl xanthine and a member of

a group of compounds known as alkaloids. Alkaloids are organic compounds

containing nitrogen and they have pharmacological effects on both humans and

animals. It is very soluble in water at its boiling temperature (0.66 g/mL) while it is

relatively less soluble at room temperature which indicates pure caffeine crystals can

be made by precipitation of the caffeine crystals at lower temperatures. It was

isolated for the first time by a German chemist, Friedlieb Ferdinand Runge, in 1819.

The chemical name of caffeine is 1,3,7-trimethylxanthine. Below, in picture 1, we can

see the chemical structure of the caffeine.

Picture 1

Caffeine is an alkaloid widely known worldwide due to its occurrence in extensively

consumed beverages, drinks and food. Natural sources of caffeine include different

varieties of coffee beans, tea leaves, guaraná seeds, maté leaves, kola nut seeds

and cocoa beans. Despite the fact that tea is globally consumed more widely than

coffee, coffee is the main source of caffeine in daily consumption given its generally

higher caffeine content. But tea and coffee are not the only sources which are

contribute to daily overall caffeine consumption, for example, caffeine could be found
1
https://pubchem.ncbi.nlm.nih.gov/compound/Caffeine

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in certain soft and energy drinks, chocolate, candies and sweets, as well as that

contained in some medications, such as stimulants, diet aids, painkillers and cold

remedies. Numerous studies have reported the effects of caffeine consumption in

humans, such as the well-known stimulant effect of low doses of caffeine on the

nervous system, which enhances concentration capacity and counteracts tiredness.

However, some more sensitive individuals or individuals consuming bigger doses of

caffeine, could experience episodes of insomnia, anxiety, nervousness, irritability,

hostility and mood swings. Other reported physiological effects are stimulation of the

gastric and urinary systems and also increased heart rate and blood pressure.

Following these negative effects, the consumption of decaffeinated coffee was

becoming more popular, enabling the chance to develop various processes that

remove caffeine from coffee beans. Among these processes, organic solvents with

high toxicity such as methylene chloride and ethyl acetate, Swiss water

decaffeination, which results in a less flavourful brew than other methods and the

employment of carbon dioxide in supercritical conditions are commonly used. CO 2 is

a non-flammable and non-toxic solvent that can be easily removed from the final

product. These advantages have driven the subsequent investigation of supercritical

extraction of caffeine from other natural sources, such as tea leaves, stalks and fibre

wastes from industrial tea processing, guaraná seeds, maté leaves, cocoa beans

and coffee oil. On the other hand, the low solubility of xanthines in supercritical CO 2,

due to its apolar character, makes the addition of polar cosolvents such as water or

ethanol an interesting practice to the compressed gasses. Cosolvent effects are

happening due to specific chemical interactions such as hydrogen bonds and acid–

base interactions or physical interactions such as dipole–dipole or dipole-induced

dipole, between the cosolvent and solute, and also to a possible interaction between

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the solvent and the cosolvent, affecting solvent-solute interactions. These effects

result in making the extraction easier and much faster. Regarding the operational

conditions, the solvent power of supercritical CO 2 is highly dependent on pressure

and temperature, variables that can be independently modified. Therefore, different

authors have reported higher yields when working at high pressures, due to the

enhanced CO2 solvent power, and when working at higher temperatures.

Hypothesis: Caffeine can be extracted through methods using chloroform

Experimental method and Procedure

In order to complete this experiment, we need to use solvent extraction. Solvent

extraction is a technique for separating materials one from another. This method is

based on the difference of the solubilities of compounds in solvents in which the

liquids are not completely miscible. This method involves the movement one

compound, known as solute, from a liquid into another liquid. For example, the

movement of caffeine, the solute, from water to an organic solvent. The solute

enriched solvent is called the extract and the water depleted of caffeine is called the

raffinate. Picture 2 shows a schematic presentation of a solvent extraction process.

Usually extraction is communicated by Extraction Yield %.

Extraction Yield % can be calculated by this formula:

Extraction Yield % = Brewed Coffee (g) x TDS (%) / Dose (g)

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 2

Picture 2

Caffeine is soluble on both water and alcohols; however, it is more soluble in

alcohols than in water. Therefore, alcohols can be used to extract caffeine from

coffee solution in water. Then, in order to extract crude caffeine from coffee solution,

we can base on the property that caffeine is more soluble in organic solvent (here I

use chloroform (CHCl3)) than that in water at room temperature. Also, chloroform is

much denser than water and insoluble in water, the caffeine in coffee solution is

transferred to the chloroform and separated out.

Water (25 °C ) Chloroform (25 °C) Water (100 °C )

Caffeine solubility 3 3 3
2.17 g/100 cm 15.8 g/100 cm 67.0 g/100 cm

Here I present a chart where the coffee brewing/extracting ratio is shown:

2
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book
%3A_Organic_Chemistry_Lab_Techniques_(Nichols)/04%3A_Extraction/4.02%3A_Overview_of_Extraction

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 3

Chemicals used for his experiment:

- Caffeine (C8H12N402, with a chemical pure grade, min. 98.5%)

- Chloroform (CHCl3)

Apparatus:

-Separating funnel

-Burette

-Pipette

-Volumetric flask

-Analytical balance

Extraction of caffeine from raw coffee powder

-Preparation of raw coffee solution

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https://coffeeperception.wordpress.com/2017/05/14/understanding-the-coffee-control-brewing-chart/

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1. 4.58g of fine grinded raw coffee powder is weighted, adding 100 cm of

distilled water and 3.0g of sodium carbonate to increase solubility of Caffeine

(alkaloid) and boil it and brew it by following the instruction on the Coffee

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package (one tablespoon of coffee powder in 100 cm of hot water, about

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4.58g /100 cm ).

2. Cool down the raw coffee solution to room temperature

Solvent Extraction

1. Rinse all apparatus with chloroform.

2. Transfer the raw coffee solution to separating funnel (shown in picture 3).

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3. Add 10 cm of chloroform and swirl vigorously (shown in picture 4). Allow the

mixture to stand and separate out the bottom chloroform layer to a beaker.

Repeat this step for 5 times.

4. Add calcium sulphate to the separated chloroform to remove water. Shake

well and stop until fluffy, cloudy effect.

5. Weight the beaker which is going to hold the filtrate.

6. Filter out the excess calcium sulphate. (shown in picture 5)

7. Put the beaker with filtrate into hot water bath to evaporate chloroform (Boiling

o
Point: 61.2 C) (shown in picture 6)

8. Weigh the powder and calculate the amount of powder extracted.

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On the next photo, is shown the whole process of extraction of caffeine from coffee,

alongside the variables that may affect during the process:

-Extraction time

-Water temperature

-Pressure

-Coffee: water ratio

-Particle size

-Water quality

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https://www.sciencedirect.com/science/article/abs/pii/S0924224419305692

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Results from the experiment

For this solvent extraction, firstly I used the 3 in 1 instant coffee and lots of emulsion

formed and I failed. Then I used fine grinded raw coffee powder in the later analysis.

During extraction, the chloroform become pale brown.

Figure 1 The pale brown colour

After the Solvent Extraction, I obtained powder of pale yellow with irritating, choking,

distinct, strong smell like soot of cigarette and coffee.

Comparing with pure caffeine and by observation, it’s obvious that the extraction

does contain impurities, considering that pure caffeine is white.

Mass of extract obtained from raw coffee solution

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-Volume of raw coffee solution used in each extraction = 100 cm

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-Concentration of raw coffee powder in raw coffee solution = 4.58 mg/ 100 cm

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http://www.solidbackgrounds.com/1920x1080-pale-brown-solid-color-background.html

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 Extraction 1 Extraction 2 Extraction 3

Mass of Beaker (g) 48.5210 48.5176 48.8572

Mass of Beaker 48.5822 48.5773 48.9097

with extracted
Crude Caffeine (g)

Mass of Extract 61.2 59.7 52.5

(mg)

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Average mass of extract in 100 cm of raw coffee solution: = (61.2+59.7+52.5)/3

= 57.8 mg

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I extracted average of 57.8 mg of solid from 100 cm of raw coffee solution (with

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4.58 mg dry coffee powder dissolved in 100 cm hot water which is the normal

concentration in brewing drinkable coffee).

Bibliography:

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 - Gillespie, Claire. "How to Extract Pure Caffeine From Coffee" sciencing.com,

https://sciencing.com/extract-pure-caffeine-coffee-7660535.html. 8 April 2021.

- International Journal of Engineering Research and Technology. ISSN 0974-3154 Volume 10,
Number 1 (2017) © International Research Publication House http://www.irphouse.com
- https://sciencing.com/extract-pure-caffeine-coffee-7660535.html

- https://chem.libretexts.org/Bookshelves/

Physical_and_Theoretical_Chemistry_Textbook_Maps/

Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/

Physical_Properties_of_Matter/States_of_Matter/Supercritical_Fluids/

Case_Study%3A_Removing_caffeine_from_Coffee

- Pradnya Ingle, et.al, “Extraction of Caffeine”, International Journal of Advanced Research in Chemical
Science, vol. 6, no. 9, p. 11-19, 2019. DOI: http://dx.doi.org/10.20431/2349-0403.0609002

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