Report : Esther

Basic Chemical Practicum Report
Esther

I. TITLE: Esther
II. DAY / DATE: Wednesday, April 27, 2017
III. AIM
1. Synthesize at least 3 kinds of esters.
2. Determine the effect of alcohol concentration on equilibrium reaction on ester manufacture.
3. Knowing the effect of carboxylic acid concentration on the reaction.
4. balance the preparation of esters.
5. Know the typical smell of several kinds of esters.
6. Using ester as a material for making soap.
7. Knowing the principle of saponification.
8. Make various soaps for washing and cosmetics.
9. Testing the working power of soap in a container water.

IV. Benefits
1. understand more about how to make ester
2. more know the influence of alcohol concentration on equilibrium reaction.
3. more know the typical smell of the element.
4. better understand the principle of saponification.
5. more know how to synthesize 3 kinds of ester.
6. better understand how to use ester as a material of soap making.
7. better know how to test the work of soap in a container water.

V. Theoretical basis
Ester is an organic compound formed by replacing one (or more) hydrogen atoms in a hydroxyl group with an organic group (usually denoted by R ')
Ester compounds
Many esters have a smell like the smell of fruits, so many of its compounds are made into artificial flavor and aroma.

Name of ester	smell
Alyl hexanoate	pineapple
Benzyl acetate	Pears, strawberries, jasmine
Bornil acetate	Pine
Ethyl acetate	Nail polish remover, paint on toys, glue
Ethyl cinnamate	Sweet skin
Ethyl format	Lemon, rum, strawberry
Ethyl isovalerate	Apple
Butyl butirat	pineapple
Ethyl butyrate	Bananas, pineapple, strawberries
Ethyl heptanoate	Apricots, cherries, grapes, raspberries

(Tobing, Rangke, 1978: 289-290).

Esters are prepared from carboxylic acids and l-ester by esterification reaction with the aid of concentrated H 2 SO 4 catalyst. The esterification reaction is actually an equilibrium reaction.
The esterification reaction is reversible. In order to obtain a high yield of the ester, the equilibrium should be slid towards the ester side. A technique for achieving this is to use one of the cheaper superfluous reagents. Another technique is to remove one product from within the reaction mixture (eg by azeotrophic distillation of water) (Hiskia, ahmad, 2001: 76).
The reactions to the ester are as follows:
1. Alkoholisis, namely terbentukya ester the other (Transesterification)

          O O
R C + R'OH acid R C + R'OH
          OR basa OR'
2. Hydrolysis to Carboxylic Acid
          O H +
R C + H2O RCOOH + R'OH
          OR RCOOH- + R'OH
OH-

3. Reactions with Grignard compounds form tertiary alcohols
          O R ''
R C + OR '+ 2R' 'MgX R C R'
OH
4. Reaction to alcohol
A. Hydrogenation of catalyst
          O
R C + 2H2 Cu.CuCrO4 RCH2OH + R'OH
          OR'

B. Chemical reduction
          O
R C OR' + Na RCH2OH + R'OH
(Respati, 1986: 168-169).
Keisomeran on ester
The isomers of the ester begin with an ester composed of four carbon atoms, an ester with a molecular formula C4H8O2. This is a structural isomer.
Functional isomers are two compounds with the same molecular formula but different functional groups.
The properties of the ester
Polar in general, thus causing ester compounds with carbon atoms slightly soluble in water (Sutresna, 2007: 225).
Properties of Esther

A) Physical Properties
1) Esters have a boiling point and a freezing point lower than the point
Boiling and freezing of the carboxylic acid of origin.
2) Low tribal esters are liquids that smell good (flavorful
fruits).

B) Chemical Properties
1) Esther is neutral and does not react with sodium metal
Or PCl3.
2) Esters may experience hydrolysis to carboxylic acids and
alcohol.


3) Hydrolysis of high ester ethers with NaOH or KOH yields
Soap and glycerol (sapling reaction).

4) Esters can be reduced to alcohol at low temperatures.

Uses of Esther

Short chain ester compounds (esters derived from low-tension carboxylic acids with low ethnic alcohols) are present in fruits that arise from the fruit, which is called fruit ester.
This ester compound is widely used as a condiment or essence.

Banana scent on food or drink can be obtained by adding amyl acetate ester. Benzilacetate gives aromastrawberry to food or drink.
In addition it is also used as a solvent in the manufacture of paints, nail polish, and adhesive.
2) Esters derived from glycerol with low or high-carboxylic acid (oils and fats).
Used as raw material for making soap and butter (margarine).
3) Esters of high ethnic alcohols and high ethyl carboxylic acids. This ester is called wax (wax), this candle is different from hydrocarbon wax (paraffin wax). Its usefulness is to polish car and floor.
(4) Esters can be reduced to alcohol at low temperatures.
(Fessenden, 1986: 281).

Uses of Esther

1) Eesters derived from low tribal carboxylic acids with low ethnic alcohols are found in fruits that give rise to the aroma of the fruit, so called fruit ester. This ester compound is widely used as flavoring or essence.

2) As a solvent on the manufacture of paint, nail polish, and adhesive.

3) Esters derived from glycerol with low or high-carboxylic acid (oils and fats).
Used as raw material for making soap and butter (margarine).
4) Esters of high ethnic alcohols and high ethyl carboxylic acids. This ester is called a candle (wax), this candle is different from hydrocarbon wax (paraffin wax). Its usefulness is for car polish and floor.
(Halim, 2013: 220).

VI. Tools and materials
• Tools
1. Reaction Tubes
2. Pipette Drops
3. Glass Watch
4. Watershed
5. Lakmus
6. 500mm Cup Cups
7. Thermometer
8. Mixer Stem

• Material
1. 1ml glacial acetic acid
2. 1ml Isoamel alcohol
3. H2SO4 6M
Mitanol 3ml
5. Benzanoic acid 250ml
6. 1ml butifat acid
7. NaOH 10%
8. Coconut Oil
9. HCL 10%
10. NaCL solution
11. CaCL2 1M
12. MgSO41M
13. Lead Nitrate 1M

VII. Work procedures
A. Synthesis and identification of esters

Tube teaction

Incorporated 1 ml glacial acetic acid and 1 ml isoamic alcohol
Add 10 drops of H2SO4
Stirred
Added to the water bath for about 10 minutes
Observed
Moved and taken a few drops onto the watch glass

 

Results

 

B. Esterification with excess alcohol

3 test tubes

Washed and dried
Incorporated 3 ml of acid
Added alcohol with volume of 1.5 ml each tube
Added each tube 10 drops H2SO4
Heated for 10 minutes
Observed layers formed
Compared to the smells that are formed and recorded

 

Results

C. Synthesis of several esters

3 test tubes

Added benzoate acid 250 m, methanol 3 ml, 15 drops H2SO4 6 M at first tube
Added asama 1 ml acetic acid, with n-butanol 1m ml, 10 drops H2SO4 on second tube
Added 1 ml butyric acid, with 1 ml of n-butanol, 10 drops of H2SO4 on the third tube

Results

D. Esterification with excess acid

Tube teaction

Dryed and put on each tube of 2 ml, 4 ml, 6 ml, acid
Added to each 3 ml of alcohol
Filled with 15 drops of H2SO4
Whipped well and heated on top of a water bath
Compared to the smell

Results

E. Saponification of esters

Tube teaction

Incorporated 1 ml 10% NaOH
Added 3 ml in a water bath until the ester smell disappears
Performed for approximately 25 minutes
Cooled on cold water
Added 1 ml of HCl 10%
Stirred
Examined its acidity using litmus
Added 10% HCl 10-20 drops until the solution is acidic

Results

F. Making soap

Glass cup 500 ml

Incorporated 5 ml coconut oil
Added 3 M NaOH and 20 ml of ethanol
Stirred and set the temperature around 90 ºC for 20 minutes
Cooled to solids
Drawn solids with a stir bar
Put into the test tube
Dissolve with hot water, then shake until visible free fatty acids
Added 25ml hot saturated NaCl solution
Cooled and lifted solids
Tested soap work power and put 3 ml of soap solution in water on 4 tubes

Tube 1

Added 1 ml of calcium chloride 1 M

Tubes 2

Added 1 ml of magnesium sulfate 1 M

Tube 3

                        Added 1 ml of 1 m lead nitrate

Tubes 4

Not added anything

Results

VIII. Observation data
SYNTHESIS AND IDENTIFICATION OF ESTER
1. Write down the equation of the esterification reaction
Answer: OH O
││ H ^ + ││
CH3COH + CH3CH¬2OH → CH3COCH2CH3 + H2O

2. Does the reaction proceed as written
Answer: No, because at the time of our experiments no changes were made
3. Evidence of the reaction
Answer
• The aroma that arises from the reaction is the scent of jackfruit
• The reaction tube feels hot when held
• There are 2 layers, the top layer of transparent white colored, and pink colored undercoat
4. The resulting esters smell like: jackfruit

B. ESTERIFICATION WITH ALCOHOL EXCESS
Tube Volume of Alcohol Acid (ml) Thickness of Odor ester layer
1 1.5 1 0.25 Stinging enough
2 1.5 1.5 0.50 Bananas
3 1.5 1 1 Very stinging

C. REACTION OF SEVERAL ESTER
Reaction Equations React / not react The physical characteristics of the product
Acetic acid + methanol + H2SO4
Reacting Odor sting
Acetic acid + n-butanol + H2SO4
Reacting Odor sting

D. ESTERIFICATION WITH EXCLUSIVE ACID
Tube Volume of Alcohol Acid (ml) Thickness of Odor ester layer
1 2 1.5 Very many Children Balloon
(Very stinging)
2 4 1.5 Many Children Balloon
(Sting)
3 6 1.5 Little Balloon Kids
(A bit stinging)

IX. Results and Discussion
A. SYNTHESIS AND IDENTIFICATION OF ESTER
In this experiment, what we did was insert 1 ml of acetic acid and 1 ml isoamic alcohol into the tube then add H2SO4 6M and heat it on the water bath. Then the solution is transferred a few drops to the watch glass to be identified.
Based on the observations, it is found that the solution produces a compound of ester so that the reaction is called an esterification reaction.
This reaction involves the carboxylic acid which in this experiment is in the form of acetic acid and alcohol in the form of ethanol with the aid of H2SO4 catalyst obtained ester compound of ethyl ethanoate and water
The reaction of acetic acid and ethanol to form ethyl acetate by reaction:
OH O
││ H ^ + ││
CH3COH + CH3CH¬2OH → CH3COCH2CH3 + H2O

The resulting ester compound has a characteristic: aromatic fragrant similar to the jackfruit scent, then the reaction tube feels hot to hold it indicates an exothermic reaction has occurred to the reaction, and 2 layers form at the end of the reaction, the top layer of transparent white and the colored bottom layer Pink.

B. ESTERIFICATION WITH ALCOHOL EXCESS
In this experiment all we did was to insert each 1.5 ml of acid into 3 tubes and add alcohol with different volumes. In tube I was added 1 ml of alcohol, on tube 2 added 1.5 ml alcohol, and in tube 3 added 1 ml alcohol. Then in each tube was added H2SO4 as catalyst.
From the observation found that the thick layer of ester in tube I is 0.25 cm which smells quite sting. In tube 2 thick layer of ester is 0.5 cm which smells of banana and sting. In tube 3 thick layer of ester is 1 cm which smells very sting.
This method of esterification with excess alcohol is one effort to enlarge the result (product). If we enlarge the product then the equilibrium will move to the reactant. Therefore, the more excess reactants the resulting product will be greater ..

C. REACTION OF SEVERAL ESTER
In our reaction reacting to 2 different tubes, the acetic acid 1 tube reacted with methanol + H2SO4 with the reaction result is an ester compound which has a very strong odorous physical properties. Our tube 2 reacts acetic acid + n-butanol + H2SO4 to obtain the reaction result of ester compound which has characteristic of odor of phisical which is very stinging and colored clear and hot which means experiencing exothermic reaction.
This suggests that if acetic acid and methanol are reacted and aided with H2SO4 catalyst there is an ester compound produced. The resulting ester compound is different and has a distinctive feature each corresponding to the amount of C atoms reacted

D. ESTERIFICATION WITH EXCESS ASAML
In this experiment all we did was insert each 1.5 ml of alcohol into 3 tubes and add different carboxylic acids. In tube I added 2 ml of acid, on tube 2 added 4 ml of acid, and on tube 3 added 6 ml of acid. Then in each tube was added H2SO4 as catalyst.
From the observation it was found that the thickness of the ester layer in tube I was 2 ml with very much layers and the smell of balloon children. In the 2-thick tube the ester layer is 4 ml with the smell of the balloon. In tube 3 thick layer of ester 6 ml with the smell of the smell of balloon slightly sting.
This method of esterification with excess alcohol is one effort to enlarge the result (product). If we enlarge the product then the equilibrium will move to the reactant. Because of the more excessive reactants the resulting product will be greater.

X. Discussion
A. ESTER SAPONIFICATION
In this experiment we did not do it because the material we used was not available. So we took data from soni apriansyah 2015, which is doing is to insert 1 ml 10% NaOH into the reaction tube then add it with 3 ml salicylic acid. Then heated over a water bath for 25 minutes. After that cool the tube. Then add 1 ml of HCL 10%, then measure the acidity level by using litmus.
Based on observations
The reaction of salicylic acid and sodium hydroxide with the help of H2SO4 catalyst will result in esters and water. The product of the ester is then reacted with hydrochloric acid (acidic atmosphere) thereby producing.
With the result of measuring its acidity level is equal to 1.

B. MAKING SOAP
In this experiment we did not do it because the material we used was not available. So we took data from soni apriansyah 2015, by reacting 5 ml of coconut oil, 15 ml of 3M NaOH, 20 ml of ethanol by heating up to reach suh 90 degree C
White-colored NaOH solution is slightly yellowish, white-colored coconut oil, while white-colored ethanol. After mixed in a glass of goblets and stirred, bubbles appear and mixed yellow colored. After heated 90 degrees C and cooled, the mixture turns solid. Then after that, the mixture was mixed with hot water and then shake it. It aims to know the reaction of sapling has been perfect or not. When the sapling reaction is complete then when mixed with hot water and dikocoklarutan it remains clear and bubbly without any drops of oil on the surface. This is called the perfection of saponification.
Then after the solution was tested and cooled the solution was added with 25 ml of saturated NaCl hot solution. The goal is that soap solids will be separated from glycerol. Then the solution is cooled down again. After that the solution is reacted with CaCl2, MgSO4, and PbNO3.
Based on the observation, on tube 1 sabn reacted with CaCl2 the result is a milky white colored solution, not foaming, dissolves. In tabt 2 the soap is reacted with MgSO4 the result is a white, turbid, non-foaming, and soluble white solution. In tube 3 the soap reacted with PbNO3 resulted in a yellowish-white colored solution, not foaming, insoluble, and deposited.
In all three tubes, soap water is not foaming / bubbly, this is because the 3 reacted solution is water sadah. The soap can not foam in the water because the stearic ion reacts with Ca, Mg, and Pb so that it becomes hard to form a scum component that is not soluble in Ca ,. Mg, and Pb stearate.

XI. Post-practice questions
1. After the observation of soap, then obtained sediment fatty acids. Is the fatty acid pure or mixed?
Answer: The fatty acid obtained is a fatty acid derived from a pure carboxylic acid.
2. Why does not soap work well in the water?
Answer: because in contained water contains ions C42 + and Mg2 + which, when reacted with the HCO2-anion, SO4- will make the soap difficult to dissolve.
3. Is the water in your laboratory quite classified?
Answer: but water is soft water with low mineral content, to prove it with soap. In soft water the soap produces a lot of foam.
4. If coconut oil is available in 1 ton of soap, what is the minimum of sodium hydroxide required?
Answer: 1 mole of coconut oil requires 3mol NaOH, so if 1 ton of coconut oil then 2 ton / 300 kg NaOH.

XII. conclusion
1. 3 kinds of esters that have been synthesized in this experiment include: benzoate acid, acetic acid, butyric acid.
2. The greater the concentration of alcohol the faster the equilibrium reaction on the preparation of the ester, otherwise The smaller the alcohol concentration the slower the equilibrium reaction on the preparation of the ester.
3. The greater the carboxylic acid concentration the faster the equilibrium reaction on the ester manufacture, the smaller the carboxylic acid concentration the slower the equilibrium reaction on the ester manufacture.
4. Typical smell of several kinds of esters, among others: jackfruit and balloon children.
5. Esters can be used as a soap-making material
6. Saponification is the reaction of saponification of fatty acid with a base which produces soap and glycerol. Fatty acids are produced from the hydrolysis of fats or heated oils
7. With this experiment we can create various macamsabun for washing and for cosmetics
8. The working power of soap in the water of the soap is not frothy (helpless) because the stearic ion reacts with Ca, Mg, and Pb so that it becomes hard to form a scum component that is not soluble in Ca ,. Mg, and Pb stearate.

XIII. Bibliography
Rangke, Tobing. 1978. Basic Chemistry Volume II.Jakarta: Erland
Ahmad, Hiskia. 2001. Chemical Kinetics. Bandung: ITB
Respati. 1976. Basic Chemistry. Jakarta: Erland
Sutresna.2007. Basic Chemistry Principles and Modern Applied. Jakarta: Erland
Fessenden. 1986. Chemical Elements. Jakarta: Erland
Halim.2013.Kimia Dasar.Bandung: Yrama Widya