Title: Extraction with acid and alkaline

Objective: 1. 2. To recover the benzoic acid and p-dichlorobenzene by acid-alkaline extraction. To determine the weight of recovered benzoic acid and p-dichlorobenzene by extraction with acid and alkaline. 3. To determine the melting point of recovered benzoic acid and p-dichlorobenzene.

Introduction: The separation of organic compound from a mixture can be done through the extraction by using acid and alkaline which known as acid-alkaline extraction. This is because acid and alkaline are soluble in aqueous solution of different pH. The extraction is result from the unequal distribution of a solute between two immiscible solvents. The distribution can be expressed quantitatively in terms of the distribution coefficient K. The equation of the distribution between an organic solvent and water are shown as below:

There are several types of extraction which involves solid-liquid extraction and liquidliquid extraction. The liquid-liquid extraction is used in this experiment. Liquid-liquid extraction is based on the transfer of a solute substance from one liquid phase into another liquid phase according to the solubility. The acid-alkaline extraction enables to change an organic soluble compound to become liquid soluble compound. For instance, when a basic solution is added to the funnel, the acidic compound is deprotonated and becomes an ionic salt which is soluble in water and insoluble in ether. The de-protonated organic salt is resides in the aqueous layer.

The carboxylic acid is strong organics acid than can be ionized in both strong inorganic base such as Sodium Hydroxide, NaOH and weak inorganic base such as Sodium bicarbonate, NaHCO. Hence, it can convert to its ionic salts in both of the base solution. In other hand, the phenols are weak organic acids only will deprotonated and form to its ionic salts when treated with strong inorganic base, NaOH, it will not deprotonated with Sodium bicarbonate (NaHCO) aqueous because NaHCO is not strong enough to deprotonate the phenol. A similar "solubility switch" also can apply to the basic organic compounds. A water insoluble organic base can be protonated to their salts by reaction with an acidic solution such as hydrochloric acid, HCl which move from the ether layer into the aqueous layer. The acidic and basic organic compounds that exist in ionic form can be recovered from the aqueous solution using the same solubility switch principles. When acid is added to an aqueous solution that contains the salt of a deprotonated organic acid, the organic acid is re-protonated. This will cause the compounds become water soluble and the recovered organic acid in solid form can be collected by suction filtration. In other hand, the salt of a protonated base(amine) can be deprotonated by addition of base solution. Hence, it will formed precipitate from the aqueous solution and can be collected in its solid form by suction filtration.

Apparatus and material: Separatory funnel (250ml), Buchner funnel, filter paper, benzoic acid, p-dichlorobenzene, ether, 10% NaOH, concentrated HCl, distilled water, anhydrous CaCl electronic balance.

Procedures: 1. 40ml of supplied ether solution which contains the benzoic acid or 2g of 2. p-dichlorobenzene mixture was poured into a small separatory funnel. 3. 20ml of NaOH solution was added into the same funnel. 4. The funnel was stopper and was shakes well and the surplus pressure was release through the tap. Next, the funnel was allowed to stand. 5. The stopper was removed and the lower aqueous layer was run into a conical flask. 6. The residue in the funnel was shake with another 10ml of 10%NaOH. 7. The lower water layer was run off into the same conical flask. 8. The concentrated HCl was added dropwise to the solution in the conical flask until litmus paper turn and no futher precipitation occurs. 9. The ether solution was washed with 30ml of water. 10. The lower layer was run off and discarded. 11. 3-4 granules of anhydrous CaCl were added into the ether solution. 12. The mixture was shaked occasionally until no turbidity remains. 13. The ether solution was decanted into a clean and dry small conical flask. 14. 1-2 boiling chip into the conical flask and was heated on the hot plate until 1520ml of ether remains. 15. The ether solution was decanted into a tarred watch glass and evaporated in fume hood. 16. The precipitated benzoic acid was filtered using a Buchner funnel and a flask. 17. The precipitate was washed with 5ml of cold distilled water. 18. The product was drawn through a current air for 5 minutes. 19. The crystal was pressed in a folded filter paper. 20. The weight and the melting point of the recovered benzoic acid was determined.

Results: Weight of benzoic acid started with Weight of p-dichlorobenzene started with Weight of benzoic acid recovered Weight of p-dichlorobenzene recovered Theoretical melting point of benzoic acid Theoretical melting point of 1.0027g 1.0019g 0.4558g 1.2127g 174C p- 53C

dichlorobenzene Melting point of benzoic acid obtained Melting obtained point of 124C

p-dichlorobenzene 54C

Calculation: % = = 45.46% %

= 54.54%

= = 121.04%

= 21.04%

= 101.89%

= 1.89%

= 101.64%
( )

= 1.64%

Discussion: References:
Acid-base extraction. (n.d.). Retrieved January 29, 2013, from http://web.centre.edu/muzyka/organic/lab/24_extraction.htm Benzoic acid. (n.d.). Retrieved January 29, 2013, from Chemicalland: http://www.chemicalland21.com/industrialchem/organic/benzoic%20acid.htm Experiment 3: Extraction: Separation of an Acidic, a Basic and a Neutral. (n.d.). Retrieved January 29, 2013, from bcs.whfreeman.com/mohrig3e Kelly, W. (n.d.). Extraction theory:separation/isolation. Leila, H. (n.d.). Selected experiment in organic chemistry. Retrieved January 27, 2013, from iugaza: http://site.iugaza.edu.ps/rmorjan/files/2010/02/practical-organic-book.pdf Phase separation and purification. (n.d.). Retrieved January 28, 2013, from http://firstyear.chem.usyd.edu.au/LabManual/E17.pdf