EXPT.

1: Purification of Benzoic Acid by Recrystallization EUGENIO & ERLANO PURIFICATION the physical separation of contaminants from a sample to produce a desired pure compound. There are different methods of purification which are dependent upon the type of compound being dealt with distillation (for liquids) and recrystallization (for solids) Purification of benzoic acid was achieved through recrystallization. RECRYSTALLIZATION a laboratory technique used to purify solids based on their different solubilities The dissolution of the solid with an appropriate solvent at a high temperature and its recrystallization at a low temperature SOLUBILITY the property of a substance called solute to dissolve in a liquid solvent to form a homogeneous solution PERCENT RECOVERY

7-STEP PROCESS OF CRYSTALLIZATION Selecting appropriate solvent (wasnt done since given na ang solvent sa procedure - water) Properties of an ideal solvent (Guide Question #1): unreactive to the compound being purified should dissolve a relatively large amount of the desired substance at a high temperature, usually the boiling point of the solvent, and a relatively small amount of it at a low temperature should be reasonably volatile, so that excess solvent can be removed from the crystals after filtration. (water was the solvent used in the experiment) Advantages of water as crystallization solvent (Guide Question #3): High heat capacity: can dissolve more and different substances at wider range of temperature Polar and readily available: since most organic subs. are polar (ie benzoic acid) Not that volatile compared to other liquids Liquid: easy to rid after filtration by drying Compared to others, it is safer (nontoxic and nonflammable) Dissolving the solute (benzoic acid + boiling chip + water + heat) Addition of boiling chip: to make boiling as smooth as possible Prevent bumping of solution or boiling over. The solution will not spill out, since the boiling chip induces boiling of the mixture. Constant Swirling: Speeds up the dissolution of benzoic acid in water. Decolorizing the solution (if necessary) Addition of activated or decolorizing carbon : to rid of colored impurities (

Provides a high surface area to adsorb colored impurities that are quite large to pass through the filter paper The solution was cooled before adding the activated carbon: to prevent it to boil over and lose products. The solution was boiled down to 1 ml: minimum amount of solvent is used to effect dissolution; using excessive amounts of solvent decreases the recovery of the solute kasi magiging dilute ang solute masyado.

Filtering suspended solids (hot mixture into a filter syringe) Hot filtration: solution filtered at high temperature. (it is assumed that the impurity is insoluble at high temperature) Rapid filtration: The solution cools as you go about filtration and hence crystallizes. The crystallized benzoic acid crystals might be filtered out and decrease the yield or recovery. add an additional 2-5% of solvent to prevent premature crystallization during this operation Crystallizing the solute (cooling in ice bath) Slow cooling is preferred over rapid cooling (Guide Question #2): slow cooling makes the crystals arrange finely, thus ensuring correct molecular arrangements/geometry. this helps the crystals form in an undistorted manner and exclude the impurities in crystal formation since it has found compounds of suitable characteristics to take in, in place of the impurities. Collecting and washing the crystals Drying the product (folded filter paper was wrapped on tissue and squeezed to remove excess water; then nilagay sa hood) Must be completely dried to prevent inaccuracy in results Guide Questions: 4. The solubility of benzoic acid in water is 0.21 g per 100 mL of water at 10oC, 0.27 g per 100 mL at 18o C, 2.75 g per 100 mL at 80oC and 6.80 g per 100 mL at 95oC Two students crystallize 10g samples of benzoic acid form water, the first dissolving benzoic acid at 80oC and filtering at 10oC, the second dissolving the acid at 95oCand filtering at 18o C. Calculate the quantity of water each student was required to use and the maximum recovery of benzoic acid possible in each case. Student 1: Dissolution @ 80OC Filtration @ 10oC

Student 2 Dissolution @ 95OC Filtration @ 18oC

5. A solid (X) is soluble in water to the extent of 1g per 100g of water at room temperature and 10g per 100g of water at the boiling point a.) How would you purify X form a mixture of 10g of X with 0.1g of impurity Y, which is completely insoluble in water, and 1g of impurity Z, having the same solubility characteristics in water as X? i. Dissolve first the mixture in 100g water and heat until boiling. Then filter to separate the impurity Y from the mixture. ii. Add water to the filtrate up to 100 mL and heat the mixture again to boiling until all crystals dissolve. Slowly cool the mixture to room temperature and filter the mixture. iii. The formation or impurity Z is insignificant (since it is minimal in quantity (1g) and has a different lattice structure from the solid X structure thus excluding Z formation ) b.) How much pure X could be obtained after one recrystallization from water? 9g of pure X would be undissolved and would recrystallize or 90% recovery Solubilities of solute are independent of one another. 1 g of Z and 10g of X would dissolve at BP with 100g water. At room temp 1g of Z will remain dissolved and only 1g of X would (since solubility of both is now 1g/100g water). c.) How much pure X could be obtained after one recrystallization from a mixture of 10g X and 9g Z? 1g of pure X could be obtained or 10% recovery. Assume 900g of water was used to dissolve mixture: so no Z would recrystallize back at room temp. since solubility is 1g/100g water Only X would recrystallize back Upon cooling, all Z are still dissolved while only 9g of X are dissolved leaving 1g of X undissolved at room temp. d.) Based on the result obtained, what is suggested about the use of crystallization as a purification technique? The crystallization technique is vey inaccurate because it heavily relies on the differences in solubility. Therefore, it is difficult to separate substances with the same solubilities especially when present in the same mixture with significant amounts.

***POSSIBLE ERRORS Possible error source

Resulting yield

Incomplete dissolution of impure sample / Boiling Over Excessive activated charcoal Excessive amount of solvent Slow filtration of first filtrate Reduced forcing of liquid from the syringe Spilling of filtrate Rapid cooling Incompletely dried filter paper ***why benzoic acid is cheap and readily available

Less yield Less yield Less yield Less yield Less yield Less yield Greater yield Greater yield

can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water other recrystallization solvents : acetic acid, benzene, petroleum ether, and a mixture of ethanol and water.