Unit Processes Lab (Final Report)

“Unit Processes Lab”

Final Lab Report
Submitted by:
2022-CH-01 Muhammad Dilshad
2022-CH-03 K.M Arslan Khan Khilji
2022-CH-27 Saad Baig
2022-CH-35 Muhammad Rayan

Submitted to:
Sir Qazi Muhammad Omer

Title: “Preparation of Flavor Bond (ethyl acetate).”

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 Unit Processes Lab (Final Report)

Objective

To synthesize ethyl acetate through the esterification reaction between ethanol and
acetic acid in the presence of concentrated sulfuric acid as a catalyst. The aim is to
demonstrate the practical application of esterification while emphasizing
techniques such as reflux, separation, and purification to obtain the ester.

Apparatus

 Round-bottom flask (250 mL)

 Reflux condenser
 Heating mantle or water bath
 Separating funnel
 Measuring cylinder (50 mL)
 Thermometer
 Beaker (100 mL)
 Distillation setup
 Glass rod
 Retort stand with clamps
 Dropper
 Ice bath

Chemicals

 Ethanol: 45 mL (used as the alcohol reactant)

 Acetic acid: 30 mL (used as the carboxylic acid reactant)
 Concentrated sulfuric acid: 5 drops (as the catalyst to enhance reaction
rate)
 Distilled water: ~50 mL (used for washing the ester and removing
impurities)
 Sodium bicarbonate solution: ~10 mL (for neutralizing residual acid)

Special Note on Chemical Quantities

The quantities of ethanol and acetic acid are chosen in a molar ratio
close to 1:1.5 to ensure that acetic acid is slightly in excess, which
helps drive the reaction forward and maximize the yield of ethyl
acetate. The amounts of sulfuric acid and sodium bicarbonate are
minimal, as they are only required for catalysis and neutralization,
respectively.

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 Unit Processes Lab (Final Report)

Theory:
Historical Background of Ethyl Acetate:

Ethyl acetate, a simple yet versatile ester, was first synthesized in 1759 by Count Michael
Benediktus Valenta von Valentano, an Austrian chemist, as part of his pioneering work on
organic compounds. The compound's pleasant fruity aroma quickly gained attention, making it
one of the first esters to be extensively studied for its properties and applications.

Today, ethyl acetate is produced globally through the Esterification of ethanol and acetic acid,
catalyzed by sulfuric acid. Its eco-friendly, biodegradable nature and diverse applications in
pharmaceuticals, food, and fragrances continue to make it a cornerstone in both industrial and
laboratory settings.

Description of Ethyl Acetate:

Ethyl acetate is an organic compound with the chemical formula C₄H₈O₂. It is a member of the
ester family, characterized by the presence of a carbonyl group adjacent to an ether linkage.
Structurally, ethyl acetate consists of an ethyl group (CH₃CH₂) attached to an acetate group
(CH₃COO), giving it a simple and compact molecular structure.

Properties of Ethyl Acetate:

 Chemical Formula: C₄H₈O₂

 Molecular Weight: 88.11 g/mol
 Appearance: Colorless liquid
 Odor: Fruity, sweet odor (similar to pear or pineapple)
 Boiling Point: 77°C (171°F)
 Melting Point: −83°C (−117.4°F)
 Density: 0.902 g/cm³ at 20°C
 Solubility in Water: Slightly soluble (approximately 8.3 g per 100 mL at 20°C)

 Refractive Index: 1.371

Ethyl acetate is known for its volatility and relatively low surface tension, which are critical
factors in its behavior in various chemical processes. These physical properties make it easily
identifiable in a laboratory setting and contribute to its widespread utility in chemical reactions
and separations.

Molecular Structure:

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 Unit Processes Lab (Final Report)

Red Colored structure: Oxygen atoms.

Light Grey structure: Hydrogen atoms.

Dark Grey structure: Carbon atoms.

Chemical Structure:

Applications and Uses of Ethyl Acetate

Ethyl acetate is a highly versatile compound with a wide range of applications across various
industries. Its unique properties, such as moderate polarity, volatility, and pleasant fruity odor,
make it indispensable in many fields.

 Paints and Coatings

Ethyl acetate is widely used as a solvent in paints, varnishes, and lacquers due to its quick
evaporation and ability to dissolve various resins.
 Adhesives
It serves as a solvent in the production of glues, especially for packaging materials,
laminates, and tapes.
 Printing Inks
Ethyl acetate is a key component in printing inks because of its fast-drying properties.

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 Unit Processes Lab (Final Report)

 Perfumes and Cosmetics

In the fragrance industry, it acts as a carrier for scents in perfumes and cosmetics, thanks
to its pleasant smell and low residue upon evaporation.
 Food Flavoring
Approved as a food additive in small amounts, ethyl acetate imparts fruity flavors in
candies, beverages, and baked goods.
 Pharmaceutical Applications: Used to prepare active pharmaceutical ingredients (APIs)
by extracting or purifying compounds. Acts as a solvent in the coating formulations for
tablets and capsules.
 Chromatography and Research Use
Commonly employed in thin-layer and liquid chromatography due to its moderate
polarity and compatibility with various solvents.
 Cleaning Applications
Effective for degreasing and cleaning electronic components, machinery, and laboratory
equipment.
 Textile and Leather Industries: Used in fabric finishing processes. A solvent in leather
production and treatment.
 Automotive and Agricultural Use: Found in car paint formulations and cleaning
products in the automotive sector. It also acts as a solvent in certain agricultural pesticide
formulations.

Safety Note!!!

While ethyl acetate is generally

safe for use, it is flammable and
can cause irritation to the skin,
eyes, or respiratory system.
Proper safety measures, such as
ventilation and protective
equipment, should be observed
when handling it.

Methods of Preparation of Ethyl Acetate

1. Esterification of Ethanol and Acetic Acid

 Ethanol reacts with acetic acid in the presence of an acid catalyst (e.g., sulfuric acid).
 Reaction:

CH3CH2OH+CH3COOH→CH3COOCH2CH3+H2O

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 Water is removed to push the equilibrium toward the ester.

 Simple setup with high yield and ease of scalability.

2. Tishchenko Reaction

 Two acetaldehyde molecules react with an aluminum alkoxide catalyst to form ethyl
acetate.
 Requires stringent conditions and is less common.

3. Ethanol Dehydrogenation

 Ethanol is passed over a copper catalyst at high temperatures.

 Reaction:
2CH3CH2OH→CH3COOCH2CH3+H2
 Produces hydrogen gas as a byproduct.

4. Acetaldehyde Oxidation

 Acetaldehyde reacts with oxygen to form ethyl acetate and water.

 Less commonly used due to safety concerns.

Why the Selected Procedure is Best

The esterification of ethanol and acetic acid is preferred because:

 Raw materials are inexpensive and readily available.

 Safer and more manageable than other methods.
 Conducted under mild conditions with high yields.
 Produces water as the sole byproduct, making it environmentally friendly.
 Suitable for both small-scale and large-scale production.

Industrial Flow sheet:

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 Unit Processes Lab (Final Report)

Experimental Procedure:
1. Prepare the reaction setup by assembling a reflux apparatus, including a round-bottom
flask, condenser, and heating mantle.
2. Add 15 g of acetic acid and 10 ml of ethanol to the round-bottom flask.
3. Introduce a few drops of concentrated sulfuric acid as a catalyst to the mixture in the
flask.
4. Attach the condenser securely to prevent loss of volatile components and start the water
flow through the condenser.
5. Heat the mixture gently to maintain a steady reflux for about 60 minutes.
6. Allow the reaction to proceed, ensuring that the ethanol and acetic acid react completely.
7. After refluxing, allow the mixture to cool to room temperature.
8. Transfer the cooled reaction mixture to a separatory funnel and add an equal volume of
distilled water to separate the ester.
9. Shake the funnel gently and allow the layers to separate. Collect the organic layer
containing ethyl acetate.

Sources of Errors:
 Impurities in reagents: Impurities in ethanol, acetic acid, or the catalyst can interfere
with the reaction, leading to lower yield and reduced product purity.
 Incorrect temperature control: Fluctuations in temperature can cause incomplete
reactions or side reactions, affecting the yield and quality of the product.
 Inaccurate measurements: Errors in measuring reactants (ethanol and acetic acid)
can result in improper stoichiometry, leading to an incomplete reaction.
 Loss of reactants during distillation: Volatile reactants or products can evaporate
during distillation, resulting in material loss and reduced yield.
 Side reactions: Unwanted side reactions, such as hydrolysis of the ester, can reduce
the yield and purity of the desired ethyl acetate.

Safety Precautions:
 Always wear safety goggles, lab coat, and gloves to protect against chemical splashes and
fumes.
 Ethanol, acetic acid, and other chemicals may release harmful vapors, so ensure proper
ventilation to avoid inhalation of fumes.
 Sulfuric acid is a strong corrosive material. Always add acid to water (not the other way
around) to prevent exothermic reactions and possible splashing.
 If using a Bunsen burner or heating mantle, ensure the heating is controlled to prevent
overheating, which could lead to boiling over or dangerous reactions.
 Dispose of chemical waste, including solvents and acids, in designated waste containers
to prevent contamination and environmental hazards.
 Ethanol and acetic acid are flammable. Keep open flames and heat sources away from the
reaction setup to minimize fire risk.

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 Unit Processes Lab (Final Report)

Results and Discussions:

In the experiment for the manufacturing of ethyl acetate, the reaction between ethanol and acetic
acid, catalyzed by sulfuric acid, proceeded smoothly under controlled conditions. The
esterification reaction was characterized by the formation of a clear liquid, indicating successful
product formation. Distillation was used to separate ethyl acetate from the reaction mixture, and
the product was collected based on its boiling point range. The distillation process effectively
separated the ethyl acetate, though slight impurities such as residual acetic acid and water were
observed. This could be attributed to incomplete removal of water during the reaction or minor
contamination during the distillation. The boiling point of the collected product was close to the
theoretical value, suggesting a high level of purity, though slight deviations may indicate the
presence of impurities. The effectiveness of the sulfuric acid catalyst was evident, as it helped
drive the esterification reaction to completion. However, some loss of material may have
occurred due to evaporation during the distillation process. In terms of reaction efficiency, side
reactions were minimal, and the overall process demonstrated the expected results. Challenges
such as temperature control and proper distillation were well managed, though optimizing these
parameters could further improve the purity of the final product.

Conclusion:

In conclusion, the experiment for manufacturing ethyl acetate successfully demonstrated the
esterification of ethanol and acetic acid using sulfuric acid as a catalyst. The reaction proceeded
efficiently, and the product was separated through distillation with a high degree of purity.
Although minor impurities were present, the yield was satisfactory. To further improve the
process, optimizing reaction conditions and minimizing material loss during distillation could
enhance both yield and purity in future experiments.

References:

1. House, D. M., & Reisch, M. S. (2010). Introduction to organic laboratory techniques:

A small-scale approach (5th ed.). Brooks/Cole.
2. McMurry, J. (2012). Organic chemistry (8th ed.). Brooks/Cole.
3. Bender, D. A. (2014). Introduction to food chemistry (2nd ed.). Elsevier.

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