Experiment #1

Purification of Benzoic Acid by Recrystallization

John Edward O.Tanchuco & Carolyn Marie D. Legaspi Section AB2 April 29, 2009

Experiment Objectives
‡ To purify and separate benzoic acid crystals from an impure sample using crystallization. ‡ To perform the proper laboratory techniques in recrystallization. ‡ To understand the concepts and computations involving purification and recrystallization.

‡ Purification 
involves the physical separation of contaminants from a sample to produce the desired pure compound.  aims to remove by-products and impurities from an impure sample.  for liquids, we usually employ distillation but for solids, we use recrystallization.

‡ Recrystallization 
a common purification method for organic compounds esp. solids  the dissolution of the solid with an appropriate solvent at a high temperature & its recrystallization at a low temperature.  two types of impurities: (1) more soluble than main component (2) less soluble than main component

Recrystallization Process
‡ An impure solid compound is dissolved in a solvent and crystallizes as the solution cools. ‡ Compounds, which are less soluble, will crystallize first. ‡ As crystals form, it selects the correct molecules, that fit in the crystal lattice & ignore the wrong molecules, resulting in a pure solid.

Recrystallization Process ‡ The crystallization process heavily depends on the differences in the solubilities of the desired solutes and the impurities dissolved in the solvent. .

Recrystallization Process ‡ Limitations  the process cannot separate pure substances and impurities with the same solubilities in a given solvent. .  the process is limited to solid solutes. it cannot assure a perfectly pure solute.  the process is not perfect. but it does increase its purity.

and the compound would be completely insoluble in the solvent at room temperature or at 0oC. usually the boiling point of the solvent.  and vice versa for the impurity .Recrystallization Solvent ‡ In the ideal setting«  the solvent would completely dissolve the compound to be purified at high temperature.

Recrystallization Solvent ‡ In the real world« In the real world. the purity of the solid can be verified by taking the melting point. . this will never happen and recrystallization is a technique that has to be practiced and perfected. Regardless of crystallization method.

Recrystallization Solvent Common Recrystallization Solvents solvent formula polarity boiling point (0C) 100 78 65 40 35 water ethanol H2O CH3CH2OH very polar polar methanol CH3OH polar dichlorometh CH2Cl2 slightly polar ane diethyl ether (CH3CH2)2O slightly polar * Note: Properties of a good recrystallization solvent will be elaborated later. .

Precipitation Recrystallization Rate slow Precipitation fast random amorphous solid significant Formation of selective crystals Shape of crystals Amount of impurities pure regular crystals negligible .Recrystallization vs.

Dissolve and heat while constantly swirling. & 2 ml distilled water.Experimental Step 1: Mix boiling chip. 100 mg impure benzoic acid. Erlenmeyer flask benzoic acid solution hot plate .

 at 10 C. 2.  but at 95 C.  this implies that at different temperatures.Discussion ‡ Water is an ideal solvent for benzoic acid. 68g benzoic acid is soluble per 1000 ml of water. . benzoic acid has an huge solubility difference in water.1 g of benzoic acid dissolves in 1000 ml of water.

thus increasing the interaction between benzoic acid and water molecules.  swirling speeds up the dissolution of benzoic acid in water  agitation increases the entropy of the system. .  the complete dissolution of benzoic acid results to a clear solution.Discussion ‡ Constant swirling at a high temperature.

. since the boiling chip induces boiling of the mixture.Discussion ‡ Adding the boiling chip while at room temperature.  adding the boiling chip at room temperature prevents boiling over. this means that the solution will not spill out.

. Add activated charcoal.Experimental Step 2: Cool the solution. Heat again until observable change is seen. Add a few drops of water.

 these can adsorb impurities (stick to the surface of the substance) from the solution but are quite large to pass through the filter paper.  activated charcoal are carbon atoms that are finely separated.  WARNING: too much activated carbon could cause the loss of the pure substance.  this results to minimization of impurities. . and increased purity.Discussion ‡ Decolorizing the solution with activated charcoal.

Experimental Step 3: Pour the hot solution in the filter syringe and force the liquid through the syringe. benzoic acid Buchner funnel vacuum(suction) filtrate .

as well as other impurities.Discussion ‡ First filtration of the solution  activated charcoal used. would be separated from the solution and left in the cotton plug.  this lessens the impurities in the crystallization process. and increases the purity of the yielded substance. .

 a lesser yield would result if the solution was not poured rapidly.  the decrease in temperature causes a decrease in the solubility of the benzoic acid crystals.  some of the pure crystals would be separated from the filtrate and would be left as residue.Discussion ‡ Filtering the solution rapidly.  as filtration is taking place so is the crystallization process. .

Experimental Step 4: Let the mixture cool in the ice bath. .

Discussion ‡ Slow cooling in ice bath.  this helps the crystals form in an undistorted manner and exclude the impurities in crystal formation. thus ensuring correct molecular arrangements/geometry. .  slow cooling makes the crystals arrange finely.

Use a seed crystal if necessary.Experimental Step 5: Collect the crystals on a filter paper. Rinse vial with ice ²cold water to collect the remaining crystals in it. .

 the seed crystal serves as a ´source codeµ where the desired solid in the solution begins crystallization.  in cases.  the seed crystal has the same structure as the pure crystal to be recovered. . that crystallization while cooling does not take place.Discussion ‡ Using a seed crystal. a seed crystal is employed.

Discussion ‡ Using a seed crystal.  impurities would remain dissolved in solution since its structure differs from the seed crystal and cannot fit in the lattice. . the other dissolved crystals would crystallize out as well.  since the lattice is a perfect fit.

Dry it completely & weigh the filter paper. .Experimental Step 6: Squeeze excess water from the filter paper.

Discussion ‡ The filter paper and crystals must be completely dried.  the added mass of water while weighing produces an inaccuracy in the desired data (% recovery) due to the solvent molecules. .

Results ‡ % recovery of benzoic acid crystals Weight of impure sample = 100 mg Weight of filter paper = 400 mg Weight of filter paper and benzoic acid = 450 mg Weight of pure crystals = 50mg % recovery: 50mg/100mg x 100% = 50% .

. the quantity of impurities and crystals recovered in each group varied.Discussion ‡ Not all groups had the same yield even if everyone used 100 mg of the same impure benzoic acid sample. ‡ Even if the same bottle was the source of the benzoic acid. the amount of impurities from each group may have varied. ‡ In conclusion.

Discussion Possible error source Incomplete dissolution of impure sample Excessive activated chracoal Slow filtration of first filtrate Reduced forcing of liquid from the syringe Rapid cooling Spilling of filtrate Incompletely dried filter paper Weighing filter paper while hot Resulting yield Less yield Less yield Less yield Less yield Greater yield Less yield Greater yield Less yield .

Comparative Group Results Group Percent Recovery # 1 2 3 4 5 6 7 8 9 80% Minimal spilling 38% Spilling 50% Error Source Spilling .

It is not a perfect process and does not produce an accurate yield.Conclusion ‡ Recrystallization is a laboratory technique used in purification of solids. ‡ A large amount of impurities with the same solubility as the pure substance is also present. . making effective separation difficult.

.Guide Questions Question#1: ‡ List the properties that an ideal solvent should have to perform the purification of organic compound by recrystallization technique.

and the compound would be completely insoluble in the solvent at room temperature or at 0oC.  and vice versa for the impurity . usually the boiling point of the solvent.Answer ‡ In the ideal setting«  the solvent would completely dissolve the compound to be purified at high temperature.

Soluble at the boiling point of the solvent and slightly soluble at room temperature. The impurities should either dissolve at room temperature or insoluble in the hot solvent so that impurities can be removed by filtration. hard to separate pure crystals because the molecules interact) 2. (if soluble.Answer ‡ A suitable solvent should be: 1. .

.Answer ‡ A suitable solvent should be: 3. The solvent should not react since their interaction would result to a lesser yield of pure crystals. The solvent should be volatile enough to be easily removed from the solute/s. This allows rapid drying of the solid compound after it has isolated from the solution. 4.

Guide Questions ‡ Question#2: What advantages does water have as a crystallization solvent? .

polar substances  high heat capacity and can dissolve different substances  safe and non-toxic compared to other organic solvents .Answer  exists as a liquid and can be used for a wide temperature range (1ÜC -100ÜC)  non-flammable and non-volatile  polar which can easily dissolve molecules esp.

.Guide Questions ‡ Question#3: Two students crystallized 10g samples of benzoic acid from water. the first dissolving benzoic acid at 80ÜC and filtering at 10ÜC . the second dissolving at 95ÜC and filtering at 18ÜC . Calculate the quantity of water each student was required to use and the maximum recovery of benzoic acid possible in each case.

27g 363.7636 g 10 g ² 0.75 g X1 ml 100 ml X1 = 363.24 g 147.21g Y2 g = 0.7636 g = 9.3971 g 10 g ² 0.0588 ml @ 18ÜC Y1 g = 0.06 ml 100ml Y2 = 0.60 g .63 ml 100ml Y1 = 0.80 g X2 ml 100 ml X2 = 147.6364 ml @ 10ÜC 2nd Student: @ 95ÜC 10 g = 6.Answer 1st Student: @ 80ÜC 10 g = 2.3971 g = 9.

Guide Questions Question # 4: A Solid (X) is soluble in water to the extent of 1 g per 100 g of water at room temperature and 10 g per 100 g of water at the boiling point. .

Guide Questions a) How would you purify X from a mixture of 10 g of X with 0. which is completely insoluble in water and 1 g impurity Z having the same solubility characteristics in water as X? .1 g impurity Y.

Cool the mixture to room temperature. Add water to the filtrate up to 100ml. Filter the mixture. Then filter to separate impurity Y from the mixture.Answer Dissolve the mixture in 100 g water and heat until boiling (100 C). . Heat the mixture again until boiling until all crystals dissolve. Slowly cool the mixture to room temperature.

Answer The residue left on the filter paper is the purified X crystals. . The formation of 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 in crystal formation.

. at room temperature. 9 g of pure X solute will crystallize.Guide Question b) How much pure X could be obtained after one recrystallization from water? ANSWER: 10g ² 1g x 100% = 90% 10 g Since the solubilities of different solutes are independent of each other. it would be assumed that 1 g of solutes X and Z would dissolve. So.

Guide Question c) How much pure X could be obtained after one recrystallization from a mixture of 10g of X with 9 g of Z? .

all X and Z must be dissolved. 10g = 1g X = 1000 g water X g 100g .Answer To retrieve pure solid X crystals from the mixture. solid X is used as basis for it is present in a larger amount. The solubilities of X and Z are independent of each other and to dissolve all crystals.

Answer To ensure that Z doesn·t crystallize back. 9g = 1g Y= 900 g water Y g 100g . This can be done by heating the solution until 900 g water is left. the final amount of water must ensure that solute Z crystals remain dissolved in water under room temperature.

Answer The solution is slowly cooled until crystals are formed. Z= 9 g solid X Z g = 1g 900g 100g In 900 g water. . 9 g of solutes X and Z are dissolved which means only 1 g of pure solid X can crystallize from the solution.

. what is suggested about the use of crystallization as a purification technique? ANSWER: The crystallization technique is very 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.d) Based on the results obtained.

THANK YOU!!! Group 1 Section AB2 .

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