Separation Of 4-Cloroaniline And Naphthalene

Introduction/Background

Acid- Base Extraction is a method used to separate organic compounds from mixtures. The theory of Acid-Base Extraction states most organic compounds are more soluble in organic solvents than in water. However, if the organic compound is rendered ionic, it becomes more soluble in water than in the organic solvent (Schaller). Because the two solvents are immiscible, they will form two layers which allows for separation of the lower layer using a separatory funnel. The name “Acid-Base Extraction” is given to this technique because by adding an acid or base to a mixture, we can extract a Base or an Acid. In this experiment, a mixture of benzoic acid, 4-chloroaniline and naphthalene will be separated using the extraction

method. Using the theory of Acid-Base Extraction,
Experimental Section

Table of Chemicals

Benzoic Acid 4-Chloroaniline Naphthalene
Table 1
Chemicals Physical Properties Chemical Properties
Benzoic Acid(C7 H6 O2 ) Molar mass:122.1g/mol
Boiling Point: 249°C
Melting point:122
Combustible at high temperature
4-Chloroaniline (C6H8ClN) Molar mass:127.6g/mol
Boiling Point:232.2°C
Melting point:69-72.5°C
Gives off toxic fumes and gasses
Naphthalene(C10H8) Molar mass:128.17g/mol
Boiling Point:217.9°C
Melting point:80.2°C

Diethyl Ether (C4H10O) Molar mass:74.12g/mol
Boiling Point:34.6°C
Melting point:-116.3°C
Burning sweet taste
Hydrochloric Acid(HCl) Molar mass:36.46g/mol
Boiling Point:85.05°C
Melting point:114°C
Colorless
Sodium Hydroxide (NaOH) Molar mass:39.99g/mol
Boiling Point:1388°C
Melting point:312°C
Odorless
Anhydrous Sodium Sulfate (Na2SO4) Molar mass:142.04
Boiling Point:1429°C
Melting point:884°C
White crystalline

Results
Table 2
Chemicals Mass Recoveries Actual Melting Point Theoretical Melting Point
Benzoic Acid .46g 120°C 122°C
4-Chloroaniline 1g 68.5°C 68-71°C
Naphthalene 1.1g 83°C 80 °C

Percent Recoveries
Benzoic Acid
%Yield = Actual / Thereotical * 100
= .46g/1.001g *100 = 45.95%
4-Chloroaniline
%Yield = Actual / Thereotical * 100
= 1g/1.001g*100 = 99.9%
Naphthalene
%Yield = Actual / Thereotical * 100
= 1.1/1.001g *100 = 109.9%
Total Percent Recovery
%Yield = Actual / Thereotical * 100
= 2.56g/3.004g *100 = 85.22%

Discussion
The results from the experiment showed that actual melting point was very accurate to that of the theoretical melting points of Benzoic Acid, 4-Cloroaniline, and Naphthalene.

This shows that our experiment yielded the correct form of each compound. The percent recovery was accurate for 4-Cloroaniline and Naphthalene yielding 99.9 and 109.9 % respectively while Benzoic Acid only yielded 45.95%. Possible reasons for Benzoic Acid yielding such a low percentage might be because of not capping the separator funnel while working to precipitate 4-chloraniline, also not removing all of the Benzoic Acid from the separatory funnel adds to a recovery less than

100%
Conclusion
In this experiment, Acid- Base Extraction was used in separating an organic mixture containing Benzoic Acid, 4-Cloroaniline, and Naphthalene.

Confirming the Acid- Base extraction theory the acid, base and organic compound making up the organic mixture were separated using a separatory funnel. Techniques performed in this lab can be applied to real life situations such as the extraction or purification of petroleum.. This Acid-Base technique performed remarkable well and separated the organic compounds from the mixture as it set out to do.

References

"Acid-Base Reactions." Science of Everyday Things. 2002, and Melvin D. Joesten. "Acid-Base Reactions." Encyclopedia.com. HighBeam Research, 01 Jan. 2002. Web. 17 Sept. 2015.

Centers for Disease Control and Prevention. Centers for Disease Control and Prevention, 01

July 2014. Web. 17 Sept. 2015.

"Naphthalene." Naphthalene. N.p., n.d. Web. 17 Sept. 2015.

Schaller, Chris P. "Acid-Base Extraction." - Chemwiki. N.p., 02 Oct. 2013. Web. 17 Sept. 2015.

Weldegirma, Solomon. "Simple and Fractional Distillation." Experimental Organic Chemistry. N.p.: 2015, n.d. 1-9.

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