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Extraction: Determination of Its Efficiency; Calculation of the Distribution Coefficient Margarita N.S. Caparas and Martha Ana G. Tacandong Bachelor of Science degree in Chemistry De La Salle University Date Performed: June 17, 2011 Date Submitted: July 8. 2011 _____________________________________________________________________________ _ Abstract Liquid liquid type of extraction was the separation technique employed in the experiment. This involves the separatory funnel being used to extract a solute from one solvent by means of a second solvent immiscible with the first. In this method, compounds are distributed in two solvents according to their relative solubilities. Thru the calculation of the distribution coefficient, one can find out the concentration or amount of solute remaining in aqueous solution after n extractions, thus, knowing which method provided more efficient results. In this experiment, toluene, the solvent, was used to extract glacial acetic acid from the acetic acid solution. The experimental procedure was carried out in two parts--single extraction and double portion extraction. The distribution coefficients for the first and second method were 0.0145 and -0.132 accordingly. This proved that a series of extractions with a small quantity of toluene is much more effective and efficient than one with a large amount of toluene because of the increasing purity of desired product with multiple extractions. Possible sources of error would be first, the presence of emulsions after the bottom layer was transferred into the flask; and mixing in the separatory funnel wasnt done efficiently. It is recommended to conduct another trial to verify obtained data and results. _____________________________________________________________________________ _

I. Introduction Extraction or liquid-liquid extraction is a technique that is essentially performed in organic teaching laboratories. This technique uses a separatory funnel as its instrument. The "liquid-liquid" phrase means that two liquids are mixed in the extraction procedure. The liquids must be

immiscible: this means that they will form two layers when mixed together. Some compounds are more soluble in the organic layer and some compounds are more soluble in the aqueous layer.[1] In the experiment done, there was partitioning of liquids done in the separatory funnel, one settled on top and the other at the bottom. This happened

because of the differences on the densities of the liquids. Extraction is efficient for separation of liquids and also for purification. Liquidliquid extraction is an energy efficient process for purifying one liquid by exploiting a solute's preferential solubility in another immiscible solvent.[2] Extraction can be done in several ways. In the experiment, two ways were done. First was by one twenty mL portion of toluene and the second way was by ten mL portion of toluene. Two ways were done to compare and contrast which is more efficient by getting their respective distribution coefficient. [3] Kd=([Ctoluene]/[Cwater]) . Results will be discussed on the results and discussion part. The solvents used in this experiment were glacial acetic acid, toluene and water. Toluene was used instead of ether. This was because ether was not available. Glacial acetic acid was used instead of TCA for the same reason. Glacial acetic acid is a liquid that has a density of 1.049 while toluene is a clear, colorless liquid that has a density of 0.86 and water having density as 1. The objectives of this extraction experiment are to execute properly the extraction of solvents, to determine how to calculate the distribution coefficient and to determine the most efficient way of extracting between the two ways mentioned above. II. Experimental In the first part, 18 M glacial acetic acid was used instead of TCA since it was

the one available. The titration setup was put up. The initial burette reading was 0 mL. Then titration started. Fifty mL of 0.1995 was already used but the substance did not turn pink yet. Since it took a long time to turn in to pink, 18 M glacial acetic acid was converted to 0.1 M. Calculations will be shown in the appendix part. From the mixture of 0.5 mL glacial acetic acid and 100 mL water, 20 mL were obtained. Titration started again. Initial burette reading was 0 mL. When the solution turned pink, 8.52 mL was obtained as the final burette reading. In the second part, extraction by one 20 mL portion of toluene was done. It was supposed to be ether but since toluene was readily available, it was the one used instead of ether. In a separatory funnel, 20 mL toluene and 20 mL of water were poured. Then the funnel was shook slightly up and down, opening it slightly to release pressure inside it. The liquids already settled in the separatory funnel and water took the bottom layer because it is denser than toluene. The bottom layer was the one collected in the Erlenmeyer flask. Few brown spots appeared in the Erlenmeyer flask, meaning a few toluene was collected with water. Titration was done again. The initial burette reading was 0 mL and 0.55 mL as the final burette reading. The solution turned pink very fast maybe because it was not pure water, some toluene came with the water substance. In the third and last part, extraction by two 20 mL portion of toluene was executed. The first substances were 10 mL toluene and 20 mL diluted glacial acetic acid and were mixed in the separatory funnel afterwards. The same procedure was done in letting the pressure out in the funnel. Glacial acetic acid took the bottom layer and was collected. Then afterwards, the collected

glacial acetic acid was placed in the separatory funnel again. Afterwards, 10 mL of toluene was added to the separatory funnel. This was done to achieve the extraction by two 20 mL portion of toluene. The bottom layer with glacial acetic acid was collected again for titration. Again, the glacial acetic acid was titrated with 0.1995
PreExtractio n 20 8.52 0.0512 Single Step Extraction 20 0.55 0.00330 0.00275 0.0399 Double Extraction 20 9.51 0.0589 0.0490 -0.00641

isolating and drying the isolate material easier. The distribution coefficient (K) is essentially the ratio of the concentrations of the solute in the two different solvents once the system reaches equilibrium. 4 At equilibrium the molecules naturally distribute themselves in the solvent where they are more soluble. Inorganic and water soluble materials will stay in the water layer and more organic molecules will remain in the organic layer. By using the correct solvent system, a molecule can be specifically selected and extracted from another solvent. Since the distribution coefficient is a ratio, unless K is very large, not all of a solute will reside in the organic layer in a single extraction. Usually two, three, or more extractions of the aqueous layer with an organic solvent are carried out in sequence in order to remove as much of the desired product from the aqueous layer as possible. As summarized on the table presented above, it is more efficient to use the method of double extraction since it yielded a lower distribution coefficient; since having a lot of extractions result to a more pure desired product.
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volume (mL) of the sample volume (mL) if titrant used number of grams (g) of acetic acid Concentration (M) of acetic acid in water concentration (M) of acetic acid in toluene number of grams (g) of acetic acid extracted Distribution Coefficient

0.0479

-0.0077

0.0145

-0.132

NaOH as the base. Initial burette reading was 0 mL and 9.81 mL was the recorded final burette reading. III. Results and Discussion One important aspect when choosing a solvent system for extraction is to pick two immiscible solvents; that is, in this experiment, toluene and water. 4Most extractions involve water because it is highly polar and immiscible with most organic solvents. In addition, the compound that one is attempting to extract must be soluble in the organic solvent, but insoluble in the water layer. Toxicity and flammability, volatility and solvents with low boiling points are factors considered in

Hypothetically, if 90% of a solid is dissolved each time, two extraction cycles should extract 99% of the material. One large extraction would have only obtained the initial 90%. Many smaller extractions are more efficient in order to remove as much of the desired product from the aqueous layer as possible. IV. Conclusion The main objective of this experiment, that is, to illustrate and execute the concept of extraction and its applications, was met. Calculation of the distribution coefficient, a quantitative measure of the how an organic

compound will distribute between aqueous and organic phases, gave rise in determining which amongst the single or multiple extraction were effective in purification and isolation of desired component. As stated in the results and discussion, double extraction method is chosen since it yielded a lower distribution coefficient and having multiple extraction for removal of desired would result to a more pure product. It is recommended to conduct another trial to verify results obtained. Also, when getting the bottom layer from the separatory funnel, try not to leave minimal amount of emulsions or droplets of the other layer with the desired component. V. Appendix A. Sample Calculations 1. conversion of 18 M glacial acetic acid M1V1 = M2V2 (18M) V1 = (0.1 M)(100 mL) V1 = 0.5 mL glacial acetic acid 2. number of grams of glacial acetic acid (before extraction) grams of glacial acetic acid = (L titrant)(molarity of titrant) = (0.00852 L)(0.1 M) = Answer * 60.05 g/mol = 0.0512 grams glacial acetic acid 3. number of grams of glacial acetic acid (first method one 20 mL portion of toluene) grams of glacial acetic acid = (L titrant)(molarity of titrant) =(0.00055 L)(0.1 M)

= Answer * 60.05 g/mol = 0.00330 grams glacial acetic acid 4. number of grams glacial acetic acid (second method two 20 mL portion of toluene) grams of glacial acetic acid = (L titrant)(molarity of titrant) = (0.00981 L)(0.1 M) = Answer * 60.05 g/mol = 0.0589 grams glacial acetic acid 5. concentration of acetic acid in water (first method) C = ((grams AcOH * 1000) / MM AcOH)) / mL water = ((0.00330 g *1000) / (60.05 g/mol)) / 20 mL water C = 0.00275 M acetic acid in water 6.concentration of acetic acid in water (second method) C = ((grams AcOH * 1000) / MM AcOH)) / mL water = ((0.0589 * 1000) / 60.05 g/mol)) / 20 mL = 0.0490 M glacial acetic acid 7. number of grams extracted (first method) gAcOH = g before extraction g of first method 0.0512 g 0.00330 g = 0.0479 g extracted on first method 8. number of grams extracted (second method)

gAcOH = g before extraction g of second method 0.0512 g 0.0589 g = -0.0077 g extracted on second method 9.concentration of acetic acid in toluene (first method) C = ((grams AcOH * 1000) / MM AcOH)) / mL toluene = ((0.0479 g *1000) / 60.05 g/mol)) / 20 mL toluene = 0.0399 M glacial acetic acid in ether 10. concentration of acetic acid in toluene (second method) C = ((grams AcOH * 1000) / MM AcOH)) / mL toluene = (( -0.0077 g * 1000) / 60.05 g/mol)) / 20 mL toluene = -0.00641 M glacial acetic in ether 11. Distribution coefficient of first method Kd = (Ctoluene / Cwater) = (0.0399 M / 0.00275 M) Kd = 0.0145 12. Distribution coefficient of second method Kd = (Ctoluene / Cwater) = (-0.00641 M / 0.0490 M) Kd = -0.132

B. Instruments Used

Separatory Funnel used for Extraction

Product for Titration

References:
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_______________________ Margarita N.S. Caparas

Organic Chemistry Library Colorado.Extraction. http://orgchem.colorado.edu/hndbksupport/e xt/ext.html (accessed July 2, 2011).

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Copper Union for the Advancement of Science and Arts.Extraction for Purification.http://www.cooper.edu/classes/e ng/ChE162/Expts/Extraction/extraction.html (accessed July 2, 2011).
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LBYCH37 Experiments (July 2, 2011)

Chem213 Introductory Organic Chemistry.Chapter 6. Liquid-Liquid Extraction. http://courses.chem.psu.edu/chem36/Experi ments/PDF's_for_techniques/Liquid_Liquid. pdf (accessed July 3, 2011)
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The University of Lethbridge. Chemistry 3840 Laboratory Manual. Paul G. Hayes, Ren Boer & Michael Gerken Department of Chemistry and Biochemistry. http://classes.uleth.ca/201101/chem3840a/C hem%203840%20Lab%20Manual %202011.pdf(accessed July 2, 2011)

I hereby certify that I have given a substantial contribution to this report and I did not copy and/or quote from any resource material unless being cited as reference. I am make known that failure to accomplish the second clause would be grounds for plagiarism and a failing grade for my final laboratory report. _______________________ Martha Ana G. Tacandong