Extraction of a neutral compound from acid and base impurities

        

NATURAL COMPOUND EXTRACTION USING ACID AND BASE IMPURITIES

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APPARATUS                            

         ·            -Analytical balance

         ·            -Dry Pasteur pipette

         ·            -Microscale kit

         ·            -Evaporator

         ·            -Stopwatch

         ·            -Erlenmeyer flask

         ·            -Screwcap centrifuge

         ·            -Litmus papers

         ·            -Droppers

         ·            -Micro spatula

         ·            -Hirsch funnel

         ·            -Filter papers

         ·            -Test tubes

         ·            -Ice bath                       

REAGENTS    

         ·            - Benzoic acid and ethyl 4-aminobenzoate  mixture

         ·            - HCl solution3M

         ·            -Diethyl ether

         ·            - NaOH solution 3M

         ·            -Distilled water

         ·            -Anhydrous sodium sulfate

         ·            -Aqueous NaOH

         ·            -Aq.HCl

         ·            -6M NaOH

         ·            -6M HCl

EXPERIMENT PURPOSE

Biological ingredients exist as complex mixtures and different elements of the mixture must be separated from each other. When natural products are separated from the plant and marine sources, most of the time one step in the process involves using an acid-base separation process. It is a great way to separate and mix organic compounds that contain similar functional groups. The main test was to separate the neutral element from the mixture containing the potential impurities. The liquid-liquid extract was performed to isolate 9-fluorenone in a mixture containing Benzoic acid and ethyl 4-aminobenzoate.

INTRODUCTION

  Acid-base organic complements are used to separate them from each other when they are synthesized. Organic acids are called carboxylic acids and contain an active COOH group. Bars contain at least one nitrogen atom known as amine. When the acid-base mixture is treated with aqueous NaOH, it will only react with carboxylic acid in that mixture, forming a dissolved salt that can be separated later. Organic compounds have no structures or acid bases.

To treat the mixture rather than aqueous HCl, it combines with the amine to form a liquid salt, which is subsequently dissolved. We, therefore, enable the reaction of each part of the reaction with NaOH or HCl to allow separation.

PROCEDURE

To the 0.15g solute, the mixture was measured in a screw -cap centrifuge tube, and 4.0ml of diethyl ether was added. The tube was glued together and turned to mix the contents until completely dissolved. After that 2ml mix, HCl was added to the tube and turned 6 times as the layers were allowed to separate. The aqueous layer was removed and placed in a 25ml Erlenmeyer column containing label A

Another 2ml of dilute HCl is added to the medium with an ether solution and the previous process is repeated while the resulting solution is completed for later use.

As a result, 2ml of dilute NaOH the same process used in HCl was repeated, and the layer placed in the Erlenmeyer flask and the B. Another 2.0ml NaOH label was added to the centrifuge tube and placed inside to mix the contents. The layers were allowed to separate and then the aqueous layer was removed and placed in a flask containing the NaOH Extract label and stored for later use.

2.0 ml of distilled water was added to the ether solution in a centrifuge tube, turned over and over again to mix the layers and allowed to separate. The dehydration was removed when the ether was later transferred to an Erlenmeyer flask using a Pasteur dry pipette and the ether solution dried over anhydrous sodium sulfate that was allowed to stand for 15 minutes. The fluid is transferred to a clean sterilized vial and soaked in steam under the hood for 20 minutes. The solids were separated by extracting with aqueous HCl and aqueous NaOH while the water delivery process continued.

Separate the extract from the acid solution of 6M NaOH drops is placed in an HCl label container while stirring with a small spatula until the mixture is absorbed. This is confirmed by the commander. The solution was tested using litmus paper to determine when to achieve an alkaline state.

The flask was then placed in an ice oven for 15 minutes and then solid was collected by vacuum filtration using a Hirsch funnel. The filter cake was transferred to a large filter paper and wrapped tightly around the solid for air suspension for use in the preparation of the next lab. To separate the extract from the 6.0 HCl alkaline medium water solution added to each drop was added to the NaOH label while stirring with a small spatula until the mixture was acidic. The previous procedure was repeated for the above solution.

The weight is recovered when the solvent is diluted in the ether is determined and recorded. As a result, the weight and melting point, carboxylic acid, ketone, and amine are determined and laid down.

OBSERVATIONS & EXPERIMENTAL DATA ANALYSIS

Solute dissolves in diethyl ether and later forms two distinct layers on the separating centrifuge

Source; LLE pt7:https://youtu.be/C6q1aq3-uCo

By adding HCl the aqueous layer penetrates the organic layer that ends up reaching the bottom.         

The benzoic acid is added to sodium sulfate and the benzoate ion is formed as it’s the aqueous layer.

Source; https://youtu.be/jMtzoZOkSR8

Then after centrifugation, the benzoic acid salt remained in the water

Red litmus paper was turned blur by the resultant solution evidencing that it was basic.

The filtration carried lead to the deposit of a precipitate

Source; LLE pt7:https://youtu.be/C6q1aq3-uCo

On reacting Hcl with benzoate ion, the Ph changed to 2.0 and the blue litmus paper turned to red confirming benzoic acid solid had been formed.

Source; LLE pt7:https://youtu.be/C6q1aq3-uCo

Carrying out vacuum filtration leads to drying out of the final compound, which is a neutral ketone

The experimental three solids extracted were;

 9-fluorenone, Benzoic acid, and ethyl 4-amino benzoate and

Melting point ranges for the extracts and the resultant masses

Extract	M.P ranges	Weight (g)
HCl	88.9-89.7	0.0268
NaOH	120.9-122.0	0.0196
Neutral	82.9-83.9	0.0460

DISCUSSION

The solubility of one compact in another is governed by the energy between the hands and the entropy. The solubility of organic compounds in organic solvents can be reported with a good mixing enthalpy.

Because acid-base reactions usually involve proton transfer between ionic species, pH affects the flexibility of organic acids in water. In the above solution, Solid benzoic acid is removed to produce water-soluble benzoate salt. As shown in the equation below;

Acidification of the benzoate anion with HCl to Ph 1.0 forms solid benzoic acid, which is soluble in water and precipitates a solid in a solution as shown below;

 Benzoic acid is isolated from the basic aqueous solution by reducing the pH and filtering the precipitate as shown below;

Source; https://youtu.be/HH93V7rYAYg

The process of filtration removes solid impurities from the solution to separates the solid product from the mixture and separates the products from the drying agent after an aqueous extraction.

In liquid-liquid extraction, the solute is distributed between two solvents that are immiscible in each other. For this purpose, water and diethyl ether, which is less polar organic solvents, are used. Since immiscible liquids do not mix and form two layers one can extract a compound from water into benzoic acid because benzoic acid is miscible with water.

See the diagram below;

The difference in the solubility of the solute in the soluble solubility and the compound transportation from one liquid phase to the other had made it possible to do the above separation. Structural factors as well as dipole forces between molecules are the major determinants of the solubility of the organic compounds.

The process of removing the ingredients involves the movement itself spreading between the aqueous layer and the organic layer depending on the tendency of its reaction. While Inorganic salt prefers the water phase, most organisms dissolve in the organic phase.

FLOWCHARTS

 Source; https://youtu.be/Xl6kT2pAUqU

General flow chart; https://youtu.be/Xl6kT2pAUqU

CONCLUSION

The purpose of the experiment was achieved since the neutral compound (9-fluorenone) was isolated from the mixture of ethyl 4-aminobenzoate and benzoic acid. The melting points were determined and their recovery masses recorded from the experimental data analysis.

REFERENCES

Chemistry laboratory Student Notebool,2^nd Edition (ISBN 0-7167-3900-3) PP.114

Laboratory Techniques in Organic Chemistry, 2nd edition Jerry.Mohrig et.al (2001) Germany

Vassar College pp. 52-156

LLE pt1:

https://youtu.be/LHkIQAVVYGs

LLE pt2:

https://youtu.be/MXJB-rkvU-I

LLE pt3a:

https://youtu.be/9WvQZSw3PH0

LLE pt3b:

https://youtu.be/HH93V7rYAYg

LLE pt4:

https://youtu.be/4p1AaUJOt10

LLE pt5:

https://youtu.be/2Y797zfW8S8

LLE pt6:

https://youtu.be/oNpz7uSS9Y8

LLE pt7:

https://youtu.be/C6q1aq3-uCo

LLE pt8:

https://youtu.be/dFLGN9MS3zQ

LLE pt9a:

https://youtu.be/IM0edOnBN20

LLE pt9b:

https://youtu.be/Xl6kT2pAUqU

LLE pt10:

https://youtu.be/WXrtA0saY20

LLE pt11: