SYNTHESIS OF ESTER- ISOAMYL ACETATE (BANANA FLAVOR)BY FISCHER REACTION

Mendoza, Edsel Daniel 2P4

Peñafiel, Mark Rean

Rañada, Mary Pauline

Sy, Patryk Renzo

Tubig, Nicholas

INTRODUCTION

Esters- any class of mostly fragrant compounds that are formed by the reaction between an acid and alcohol with elimination of water, it can be synthetically produced by the use of Fischer Reaction.

INTRODUCTION

Fischer esterification- first described by Emil Fischer (1895) is the treatment of carboxylic acid with an alcohol with an acid catalyst to form esters (Franklin and Hippeläinen, 2012).

OTHER ESTERS OF DIFFERENT FLAVORS

Alcohol Carboxylic acid Ester(product) Fragrance

Isoamyl alcohol Acetic anhydride

Isoamyl acetate Banana

Octanol Acetic acid Octyl Acetate Orange

Methanol Salicylic acid Methyl Salicytate

Wintergreen

Propanol Acetic acid Propyl acetate Pear

Benzyl alcohol Acetic acid Benzyl acetate Peach

Butanol Butyric acid Butyl butyrate Pineapple

Ethanol Butyric acid Ethyl butyrate strawberry

OBJECTIVES

At the end of the experiment, we should be able to: Synthesize the Isoamyl acetate

Calculate for the percent yield

BACKGROUND INFORMATION

Chemicals used: Isoamyl Alcohol (CH3)2CHCH2CH2OH

Acetic Anhydride C4H6O3

Sulfuric Acid H2SO4 Sodium bicarbonate NaHCO3 Sodium Sulfate Na2SO4

Isoamyl Acetate C7H14O2

BACKGROUND INFORMATIONChemical Description Application

Isoamyl Alcohol clear, colorless alcohol Used as an antifoaming agent in the Chloroform: Isoamyl Alcohol reagentmain ingredient in the production of banana oil

Acetic Anhydride flexible molecule with a nonplanar structure versatile reagent for acetylation

Commonly used as an acetylating agent

BACKGROUND INFORMATIONChemical Description Application

Sulfuric Acid Highly corrosive strong mineral acid; Pungent-ethereal, colorless to slightly yellow viscous liquid Soluble in water at all concentrations

Used in large quantities by iron and steelmaking industry to remove rust

As an acid catalyst

Sodium bicarbonate White solid that is crystalline but often appears as a fine powderPrepared by the reaction of sodium chloride, ammonia, and carbon dioxide in water

Can be used to extinguish small grease or electricalWash to remove any acidic impurities Removing paint and corrosion

BACKGROUND INFORMATIONChemical Description Application

Anhydrous Sodium Sulfate

Sodium salt of sulfuric acid. When anhydrous, it is a white crystalline solidContains no water

Manufacture of detergents and in the Kraft process of paper pulping

Drying agent to remove water from a solution

Isoamyl Acetate Organic compoundEster formed from isoamyl alcohol and acetic acidColorless liquid; Slightly soluble in water; Very soluble in most organic solvents; Strong odor and low toxicity.

Used to confer banana flavor in foodsUsed to attract large groups of honeybees to a small area (Boch, 1962)Used to test the effectiveness of respirators or gas masks

PROCEDURES USED

Reflux Set Up Liquid-Liquid Extraction(through Separatory Funnel)

REFLUX SET UP

Distillation technique involving the condensation of vapors and the return of this condensate to the system from which it originated (Henry, 1992).

Reflux Setup

LIQUID-LIQUID EXTRACTION(THROUGH SEPARATORY FUNNEL) extraction of a substance from one liquid into

another liquid phase method to separate compounds based on their

relative solubilities in two different immiscible liquids, usually water and an organic solvent.

A separatory funnel, is used in liquid-liquid extractions to separate the components of a mixture into two immiscible solvent phases of different densities

Separatory Funnel

METHODOLOGY

Isoamyl Alcohol (A)(5.0ml)

Acetic Anhydride (B)(5.2ml)

Reflux Set-up

Separatory funnel

-Added 5 drops of H2SO4-Placed in ice bath

-Added 2 pcs. Of boiling chips-Boiled in H20 bath at 75-80c for 30 mins.-Poured in a 50 ml beaker which contained crush ice-removed boiling chips

-Placed in ice bath

Separatory funnel

Lower layer Upper layer

Lower layer Upper layer

-Added 15 ml saturated (NaHCO3)-Swirled

-Added 15 ml saturated (NaHCO3)-Swirled

-Drained

-Drained

Upper layer

Lower layer Upper layer

Residue

Isoamyl Acetate

-Added 15 ml saturated NaCl-Swirled

-Drained in 50 ml beaker-Added ½ spatula of anhydrous Na2SO4-Swirled-Decanted

-Drained

-Discarded

-in a pre weighed vial-weighed again-Calculated %yield

RESULTS *Theoretical yield:

0.0459 x 1 x 130.2 = 5.9762

*Number of moles C4H6O3

(Acetic Anhydride):

5.2mL x 1.0820g/1mL x 1mol/102.09g = 0.05511 mol

*Number of moles of C5H12O (Isoamyl Alcohol):

5mL x 0.8092g/1mL x 1mol/88.146g = 0.459 mol

2C5H12O + C4H6O3 2C7H14O2 + H2O

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 19.2539 g

Weight of product 4.7524 g

Percent Yield 79.52%

Description of product Colorless liquid-like, strong vanilla-like scent

Group 1

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.75/5.98 x 100 =79.52%

Group 1

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 10.62 g

Weight of product 5.65 g

Percent Yield 94.48%

Description of product Colorless product, banana scent, smells good

Group 2

Percent Yield = actual yield/theoretical yield x 100

% yield = 5.65/5.98 x 100 = 94.48%

Group 2

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 11.4153 g

Weight of product 4.1187 g

Percent Yield 68.93%

Description of product colorless

Group 3

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.1187/5.9762 x 100 = 68.93%

Group 3

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 15.1304 g

Weight of product 4.0292 g

Percent Yield 67.42%

Description of product Colorless thick oily liquid, smells concentrated

Group 4

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.0292/5.9762 x 100 =67.42%

Group 4

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 14.3097 g

Weight of product 4.0397 g

Percent Yield 67.55%

Description of product Colorless, banana-like smell

Group 5

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.04/5.98x 100 =67.55%

Group 5

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 11.2334 g

Weight of product 4.0460 g

Percent Yield 67.70%

Description of product Colorless liquid, banana-like smell

Group 6

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.0460/5.9762 x 100 = 67.70%

Group 6

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 21.38 g

Weight of product 4.33 g

Percent Yield 72.46%

Description of product Colorless liquid like water, strong smell of banana

Group 7

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.33/5.9762 x 100 =72.46%

Group 7

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 12.3712 g

Weight of product 3.28 g

Percent Yield 54.88%

Description of product Colorless liquid, banana-like strong smell

Group 8

Percent Yield = actual yield/theoretical yield x 100

% yield = 3.28/5.9762 x 100 = 54.88%

Group 8

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/ml

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 mol

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 16.1025 g

Weight of product 3.1407 g

Percent Yield 52.55%

Description of product Colorless candy-like scent, banana candy scent

Group 9

Percent Yield = actual yield/theoretical yield x 100

% yield = 3.1407/5.9762 x 100 = 52.55%

Group 9

Table of Data and Results

Volume of Isoamyl Alcohol 5.0 ml

Density of Isoamyl Alcohol 0.8092 g/mL

Molecular weight of Isoamyl Alcohol 88.146 g/mol

Number of moles of Isoamyl Alcohol 0.04590 moles

Volume of Acetic Anhydride 5.2 mL

Density of Acetic Anhydride 1.0820 g/mL

Molecular weight of Acetic Anhydride 102.09 g/mL

Number of moles of Acetic Anhydride 0.0551 moles

Molecular weight of Isoamyl Acetate 130.2 g/mol

Theoretical Yield 5.9762 g

Weight of empty vial 12. 17 g

Weight of product 4.3464 g

Percent Yield 72.7285%

Description of product Colorless liquid, concentrated banana flavor

Group 10

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.3464/5.9762 x 100 = 72.7385%

Group 10

COMPARISONS OF % YIELD OF GROUPS 1-10

% yield

Group Percent yield

1 79.52%

2 94.98%

3 68.93%

4 67.42%

5 67.55%

6 67.70%

7 72.46%

8 54.88%

9 52.55%

10 72.74%

1 2 3 4 5 6 7 8 9 100

10

20

30

40

50

60

70

80

90

100

Groups

Percent Yield = actual yield/theoretical yield x 100

% yield = 4.3464/5.9762 x 100 = 72.7385%

Group 10

Group Weight of product

1 4.75 g

2 5.75 g

3 4.12 g

4 4.03 g

5 4.04 g

6 4.05 g

7 4.33 g

8 3.28 g

9 3.14 g

10 4.35 g

WEIGHT OF PRODUCT

Isoamyl Alcohol (A)(5.0ml)

Acetic Anhydride (B)(5.2ml)

Reflux Set-up

Separatory funnel EXTRACTION

ESTERIFICATION

SOLUBILITY

Separatory funnel

Lower layer Upper layer

Lower layer Upper layer

EXTRACTION

EXTRACTION

Saturated NaHCO3

Saturated NaHCO3

Upper layer

Lower layer Upper layer

Residue

Isoamyl Acetate

Extraction

Extraction

DRYING

Saturated NaCl

Anhydrous Na2SO4

PRINCIPLES BEHIND THE EXPERIMENT

SOLUBILITY Neutralization Drying

SOLUBILITY

Acetic acid and Sulfuric acid are washed away by H2O because the two are water soluble

Water cools down the reaction

NEUTRALIZATION

Saturated NaHCO3 (amphoteric) removes excess acetic acid and acid catalyst (H2SO4)

DRYING

DRYING AGENTS:

1. Saturated NaCl

Salts have stronger attraction to water than organic solvents

2. Anhydrous Na2SO4

inorganic salt which takes up water to become hydrated

POSSIBLE SOURCES OF ERROR

Results and data may have been affected by the following deviations: Improper use or using different materials for the

experiment Incorrect following of procedures Improper extraction and draining

Timing

Inexact amount of added compound Contaminated materials and containers

CONCLUSION

Every group was able to prepare and execute Fischer esterification and liquid-liquid extraction .

Every group was able to calculate the percent yield of their product

Average percent yield : 76.67%

REFERENCES

Ester.2015. Encyclopædia Britannica retrieved from

http://www.britannica.com/EBchecked/topic/193393/ester

Franklin and Hippeläinen. (2012). FISCHER–SPEIER ESTERIFICATION ORGANIC SYNTHESIS & THE HISTORICAL METHOD. Retrieved from

http://ouluma.fi/wp-content/uploads/2012/04/ficher-speier_esterification.pdf

REFERENCES

Zumbo, P. "Phenol-chloroform Extraction". WEILL CORNELL MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E. MASON, PH.D. Retrieved 19 June2014.

Boch R; Shearer DA; Stone BC (September 8, 1962). "Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee.". Nature (England: Nature Publishing Group) 195 (4845): 1018–20

 "Arm & Hammer Baking Soda – Basics – The Magic Of Arm & Hammer Baking Soda“ Retrieved from ArmHammer.com

Kister, Henry Z. (1992). Distillation Design (1st Edition ed.). McGraw-Hill.