CU20629 Oil- and Biorefinery

EXP003A: Synthesis of Banana Oil

1. Introduction
Cavendish Distilling Company sells the liqueur Banana Elixir, which is flavored with a natural
banana extract from fruit grown on Caribbean banana plantations. Due to a hurricane all
banana trees blew down and the stock of banana extract is running low and there is no
alternative source. The company has decided to add synthetic banana flavorings. This
synthetic ester banana oil can be synthesized by a process called the Fischer esterification,
a reaction between an acid such as acetic acid and an alcohol such as 3-methylbutan-1-ol
(iso-amyl alcohol). One problem: this reaction doesn’t go to completion, leaving considerable
amounts of starting material in the product. Specifications of the banana oil: a maximum of
10 % 3-methylbutan-1-ol and less than 2% acetic acid (Lehman, 2009).

Assignment
Prepare synthetic banana oil and see if it falls within the tolerances of the company.

2. Chemicals, solutions and samples

● 3-methylbutan-1-ol.
● Glacial acetic acid1.
● Sulfuric acid, concentrated.
● Anhydrous sodium sulphate or magnesium sulphate.
● Sodium hydrogen carbonate solution, 5% (m/V).

3. Materials and Equipment

● Round-bottom flask, 100 ml.
● Allihn condenser (see appendix 1 for an overview of different kinds of condensers).
● Separation funnel, 100 - 250 ml.
● Filter paper
● Electric heating mantle, 100 ml.
● Boiling stones.
● Sample jar for storing the banana oil.

4. Procedure
Reaction
● Accurately weigh 150 mmol of 3-methylbutan-1-ol into a round-bottom flask of 100 ml
and add boiling stones.
● In the fume cupboard, add ± 300 mmol of glacial acetic acid, and then add dropwise
with a glass dropper 1 ml of concentrated sulfuric acid while swirling.

1
Glacial acetic acid is a pure grade of acetic acid that freezes at about 17 °C.

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Take care! Avoid contact with glacial acetic acid and concentrated sulfuric acid; do
not breathe their vapors.
● Connect a Allihn condenser to the flask. Let the teacher check the set-up!
● Turn on the cooling water and heat the reaction mixture (be careful, do not turn the
heat to max straight away or the reactants will burn). Reflux for one hour after boiling
begins. Look for and record any evidence of a chemical reaction.

Introduction refractometer
See SOP021 Determining the Refractive Index (RI) for an instruction. The teacher will give
a demonstration.

After this demonstration you calibrate the refractometer with water and you measure the
refractive index of pure 3-methylbutan-1-ol (starting compound) and 3-methyl-1-butyl
ethanoate (banana oil). Measure also the temperature of the environment. Write down all
the observations in your laboratory journal and include the theoretical RI of the pure
compounds.

Separation
● When the reaction time is up, allow the reaction mixture to cool to room temperature.
● Turn off the cooling water and remove the reflux condenser.
● Transfer the reaction mixture to a separatory funnel, leaving the boiling stones
behind. Wash the flask twice with 25 ml of water and add this to the separatory
funnel as well.
● Shake vigorously to mix the content and vent frequently (ask your teacher for a
demonstration).
● Allow the layers to separate. (Question. What is the density of 3-methyl-1-butyl
ethanoate? Which layer should be on top, the aqueous layer or the organic layer?)
● Drain the aqueous layer and leave the organic layer in the separatory funnel (make
sure to not waste the organic layer, since this contains the product!).
● Carefully wash the organic layer with two successive portions of 5% aqueous sodium
bicarbonate, draining the aqueous layer after each washing. During the first washing,
mix the layers until gas evolution subsides before you stopper the separatory funnel,
and vent it frequently thereafter. Take care! Pressure may build up in the stoppered
separatory funnel.
● Drain the product into a 100 ml Erlenmeyer flask and add enough anhydrous sodium
sulphate.
● Filtrate the product directly into a collection bottle and calculate the mass and percent
yield of the crude product.

5. Reporting
● Insert the observations in the Observations sheet on Learn before you leave the
laboratory.
● Make sure your lab journal is complete. So include a short discussion & conclusion.
Does your product meet the product specifications of the company?
● Write a report that covers both day 1 and 2 of EXP003 “Synthesis of Banana oil” and

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submit on learn.hz. See Assessment form REPORT Year 1 (Chemistry Department,

sd) for the assessment criteria.

You are allowed to use generative AI for this assignment. You can use it for
generating ideas, brainstorming and improve writing. The final product should be your
original work and not contain any content that has been generated with any form of
AI. In case there is a suspicion of using AI generated content in your final product
this is considered fraud and will be handled as such.

6. Literature
Lehman, J.W. (2009). Operational organic chemistry. A problem-solving approach to the
laboratory course. New Jersey: Pearson education.

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Appendix 1 Overview of condensers

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