Preparation of Fruit Flavors

Tabia Carmela, Villanueva Michael*, Viloria Jasper, Yoon Subin

Department of Biology, University of Santo Tomas, Manila, Philippines

Abstract

This experiment was conducted to exhibit the synthesis of banana flavoring in the laboratory
through the esterification of isoamyl alcohol and acetic anhydride with the use of the Fischer-Speier
reaction. The set-up used was the reflux modified with a water bath at the constant temperature between
75-80 degrees Celsius. The actual yield that was attained was 4.3798 g/mol and the theoretical yield, on
the other hand, was computed to be 5.97 g/mol. The percent yield was determined to be 73.36%.

Introduction

Food Chemistry plays a very important role in culinary enterprises nowadays. It manages the
natural and non-organic parts of sustenance and its synthetic procedures. As business increase in the
nourishment business, there is a need to create more and less expensive methods in combining flavoring
in snacks or beverages without decreasing the quality of the food. Utilizing artificial flavors may bring
many advantages, for example, drawing out the time span and prolonging the shelf life or simply
enhancing the taste of the food.

Esters are a body of a naturally occurring compound that generally carry a distinctive odor. Most
organic fragrances and fruit flavors belong to this class of compounds. Any compound that has the

functional group ester would include the structure:

In our research center it may be artificially made by means of the Fischer reaction. This would
then enable the compound to have a specific fragrance or flavor that could then be added to the food
after it has been well or appropriately filtered. The Fischer reaction is a type of esterification technique
that requires a carboxylic acid and an alcohol with the guide of catalysts. In the reaction the carboxylic
corrosive and the alcohol reactants are in equilibrium with the ester product. The Fischer reaction is
additionally considered for instance of a nucleophilic acyl substitution when based on its degree of being
electrophile of the carbonyl carbons and the range of being nucleophile of the alcohol reagents within the
chemical equation and the experiment.
 In spite of its simplicity, the Fischer response additionally holds a few drawbacks in esterification.
One case of its burden is in the thermodynamic stream in the view point that it is reversible. Another
disadvantage would be its moderate reaction rates. This could be an issue particularly when the reactants
that are being used are compounds that is delicate to strong acids.

Coupling the Fischer reaction would be including the utilization of the reflux set-up. The reflux
set-up will take into account the heat required for the reactions to take insignificant loss of reactants that
have high volatility such as alcohol. The reflux set-up has a few insignificant segments that enables it to
be efficient. The distilling flask is the container where the reactants of the Fischer reaction will be placed.
It is attached to the condenser that has a constant flow of cooling water flowing through it. This cools the
inside of the tube of the condenser, by condensing and hindering the alcohol or highly volatile liquids from
escaping. The condenser has an incurrent passage and an excurrent passage to expel the water.

Another viewpoint the experiment has aimed to handle is to show a particular filtration method
called Extraction. This method is only efficient for liquid-liquid isolation. It is typically done with the help
of a separation funnel. The funnel is shaped like a water bead with the topside globular and the bottom
of the side funnel shaped. The top part has a small opening for the entry of reagents or liquids with
different densities while the opposite end has a valve to allow and segregate the liquids.

Results and Discussion

The chemical formula in preparing a banana essence ester is: Isoamyl Alcohol + Acetic Anhydride
=> Isoacetate + Acetic acid

Being that this reaction is a synthesis of esters, the reagents are in equilibrium with the products.
The chemical formula therefore, depicts 1:1 ratios among the reagents and the products. Given that there
is an availability of 2.5 isoamyl alcohol and 2.6 ml of acetic anhydride, it is possible to determine the
limiting reagent and the theoretical yield. Once the theoretical yield is known and the experiment has
been conducted with the weighed product, the percent yield can then be computed for.

Weight of vial 12.2470

Weight of vial + Isoamyl acetate 12. 2470 + 4.3798 = 16.6268g

Isoamyl alcohol is:

0.8902 g/ml 88.2 g/mol

Acetic anhydride:

2.8132 g/ml 102.1 g/mol

With the densities given, the mass of the reactants can now be calculated as follows:

5 ml isoamyl alcohol x 0.8092 g/ml = 4.046 g

5.2 ml acetic anhydride x 1.0820 g/ml = 5.6264 g

These values are the grams of isoamyl alcohol and acetic anhydride given for the experiment.
With these, we can now find out the limiting reagent.

4.046 g AA (1 mol AA) (1 mol Ialc) (130.2 g Ialc) = 5.972 g Ialc

88.2 g/mol 1 mol AA 1 mol Ialc

Because only 4.046 grams of isoamyl alcohol is given when the equation requires 5.972 g, isoamyl
alcohol is therefore the limiting reagent as 5.972g (theoretical computation) > 4.046 g (amount given).

5.6264 g Ialc (1 mol AA) (1 mol Ialc) ( 130.2 g Ialc) = 7.17 g AA

102.1 g Ialc 1 mol AA 1 mol AA

This means that the Acetic anhydride is the excess reagent.

To find the theoretical yield, one must use the mass of the limiting reagent because the amount
of product produced is directly proportional to the limiting reagent available. As a result, no matter how
many uncooked chicken a restaurant has, if it only has a single stove then limited food can be produced.

% yield = 4.3798 g x (100) = 73.36%

5.97 g/mol

Normally, the percent yield was registered to decide scientifically how proficient the set-up
functioned or how much defect was available in leading the experiment.

As for the rationalization of the chemicals used in the experiment and techniques used will be
more elaborated in this section of discussion.

In view of the systems, five drops of acid were added to the anhydride. This may prompt the
inquiry as to why the acid was not dropped into the alcohol. The reason is for this is for safety precautions.
It would avoid the possibility of an exothermic reaction if the acid was added to the anhydride because
the anhydride is a type of acid too. It is basic that the test tubes be submerged in ice water in light of the
fact that the response is profoundly exothermic and will probably have speedier moving atoms in this way
is likewise prone to splatter and consume causing damage. Ice even when melting and the water puddle
it makes around it will still main a constant temperature of 100 degrees Celsius until the ice is completely
dissolved, which is why the reason ice water is favored over lumps of ice with air in the middle. It would
be more troublesome for the ice to cool the air in the middle of the lumps of ice as the particles are more
distant from each other as compared to water.

The set-up was additionally submerged in a water bath, to uniformly disseminate the warmth and
it is a standard operating procedure for safety to apply water baths to combustible, reactive, and highly
volatile liquids such as the alcohol used in the experiment. The HCO3 was then added to the mixture, This
aides by making an aqueous layer and organic layer contributing in purifying the mixture. The air pockets
and fizz are the byproduct of the HCO3 which is CO2. After the bubble has been dissipated, the funnel
must be swirled carefully to avoid the formation of emulsion of the organic layer. Arrangement of these
fine scatterings of droplets, may cause errors when segregating the fluids. At that point half a spatula of
Na2So4 was utilized to dry the natural item. The chemistry term drying refers to the absorption of excess
or unnecessary water.

Experimental

Preparation of banana essence. The test tubes were labeled A and B . The test tube labeled A
was filled with the reactant isoamyl alcohol (5 ml) while the test tube B was filled with the reactant acetic
anhydride (5.6 ml). Both test tubes were both placed in an ice-water bath. Concentrated H2SO4 was slowly
added mixed in test tube B. After, the contents of test tube B were cautiously mixed drop-by-drop using
a dropper with the isoamyl alcohol in test tube A while it was being swirled constantly. A reflux set-up was
collected with and modified with the distillation flask partially submerged in a water bath. The mixture in
test tube A was then poured in a reflux set-up at 80 with a few boiling chips for thirty minutes. Then the
mixture was cooled for one minute and poured in a beaker with a crushed ice cube. Next, the concoction
was then transferred to a separatory funnel where 15 ml of saturated NaHCO3 was added. Bubbles from
the solution were allowed to escape and cease forming before the funnel was secured with a cap. The
separatory funnel was gently swirled and allowed to separate before the top, less dense organic layer was
isolated. The denser aqueous layer was discarded. The process was repeated with another 15 ml of HCO3
then extracted with 15 ml of saturated NaCl solution, discarding the aqueous layer. The organic layer was
then added with one half spatula of and decanted to be placed in a pre-weighed vial.

Separating Funnel Set-up

Reflex set-up

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