banana synthesis of ester
DESCRIPTION
Synthesis of Ester- Isoamyl ACETATE (BANANA FLAVOR)By fischer ReactionTRANSCRIPT
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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
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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.
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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).
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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
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OBJECTIVES
At the end of the experiment, we should be able to: Synthesize the Isoamyl acetate
Calculate for the percent yield
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BACKGROUND INFORMATION
Chemicals used: Isoamyl Alcohol (CH3)2CHCH2CH2OH
Acetic Anhydride C4H6O3
Sulfuric Acid H2SO4 Sodium bicarbonate NaHCO3 Sodium Sulfate Na2SO4
Isoamyl Acetate C7H14O2
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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
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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
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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
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PROCEDURES USED
Reflux Set Up Liquid-Liquid Extraction(through Separatory Funnel)
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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).
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Reflux Setup
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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
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Separatory Funnel
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METHODOLOGY
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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
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Separatory funnel
Lower layer Upper layer
Lower layer Upper layer
-Added 15 ml saturated (NaHCO3)-Swirled
-Added 15 ml saturated (NaHCO3)-Swirled
-Drained
-Drained
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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
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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
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.75/5.98 x 100 =79.52%
Group 1
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 5.65/5.98 x 100 = 94.48%
Group 2
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.1187/5.9762 x 100 = 68.93%
Group 3
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.0292/5.9762 x 100 =67.42%
Group 4
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.04/5.98x 100 =67.55%
Group 5
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.0460/5.9762 x 100 = 67.70%
Group 6
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.33/5.9762 x 100 =72.46%
Group 7
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 3.28/5.9762 x 100 = 54.88%
Group 8
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 3.1407/5.9762 x 100 = 52.55%
Group 9
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.3464/5.9762 x 100 = 72.7385%
Group 10
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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
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Percent Yield = actual yield/theoretical yield x 100
% yield = 4.3464/5.9762 x 100 = 72.7385%
Group 10
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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
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Isoamyl Alcohol (A)(5.0ml)
Acetic Anhydride (B)(5.2ml)
Reflux Set-up
Separatory funnel EXTRACTION
ESTERIFICATION
SOLUBILITY
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Separatory funnel
Lower layer Upper layer
Lower layer Upper layer
EXTRACTION
EXTRACTION
Saturated NaHCO3
Saturated NaHCO3
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Upper layer
Lower layer Upper layer
Residue
Isoamyl Acetate
Extraction
Extraction
DRYING
Saturated NaCl
Anhydrous Na2SO4
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PRINCIPLES BEHIND THE EXPERIMENT
SOLUBILITY Neutralization Drying
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SOLUBILITY
Acetic acid and Sulfuric acid are washed away by H2O because the two are water soluble
Water cools down the reaction
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NEUTRALIZATION
Saturated NaHCO3 (amphoteric) removes excess acetic acid and acid catalyst (H2SO4)
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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
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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
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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%
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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
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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.