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Sidney Ty Locker Number 37 B

Ch 22.2 G Experiment 1: Purification of Benzoic Acid Post-Lab February 19, 2019

Data and Results


Table 1. Data and Results from the Experiment
Appearance of crude benzoic acid sample Bluish white crystalline solid with
colored impurities
Mass of crude benzoic acid sample (g) 2.01
Volume of water added (mL) 75.00
Mass of decolorizing charcoal added (g) 0.10
Mass of sample jar with recovered benzoic acid 14.77
crystals (g)
Mass of sample jar (g) 12.87
Mass of recovered benzoic crystals (g) 1.90
Melting point of recovered benzoic crystals (°C) 120.6
Appearance of recovered benzoic acid crystals White crystalline solid

Table 2. Percent Recovery of Benzoic Acid


Data Actual
Percent Recovery 94.5 %

Discussion

This experiment involves the process of crystallization in the purification of crude


benzoic acid. Since there was a slow formation of the benzoic acid crystals in this
experiment, the obtained sample was in the form of crystals and not precipitates. The main
difference between crystallization and precipitation is the rate of cooling of a solution. In
crystallization, the solution is allowed to cool down slowly and gradually to remove
impurities. On the other hand, in precipitation, the solution cools quickly, possibly leaving in
some impurities and the formation of a cloudy mixture. (AtQ1)

The percent recovery of benzoic acid in this experiment was calculated to be 94.5%.
This value may have been affected by the amount of decolorizing charcoal used to purify the
crude benzoic acid in this experiment. By adding more decolorizing charcoal, more
impurities are adsorbed and removed from the rest of the solution during filtration, leaving us
with a smaller value for percent recovery. Decolorizing charcoal may also adsorb benzoic
acid. Therefore, it is important not to put too much decolorizing charcoal to maximize
percent recovery of benzoic acid. (AtQ2) However, too little decolorizing charcoal added
may result in a less pure recovered substance. Aside from the amount of charcoal, the
temperature of the water used to wash the crystals during suction filtration may affect percent
recovery as well. The reason why cold solvent is used to wash the crystals is to prevent
further dissolution of the crystals, which may pass through the suction filtration set-up. Cold
solvent being used to wash off the crystals therefore minimizes the sample lost because the
compound becomes insoluble to the cold liquid. (AtQ3)

As mentioned earlier, putting too little decolorizing charcoal in the solution will
produce a less pure product. The purity of the product affects its melting point since a
substance containing soluble impurities has a lower melting point compared to a pure
substance. In addition, a wide or broad melting point range means that the purity of the
product could still be improved. (AtQ4) In this experiment, the melting point of the purified
benzoic acid crystals is 120.6 °C as compared to the melting point of pure benzoic acid at
122.4 °C. This shows that the obtained benzoic acid crystals in this experiment may still
contain some impurities since its melting point is lower than that of the pure compound. The
percent error calculated between the two melting point values is 1.47%.

The maximum theoretical percent recovery from the recrystallization of 2.0 g benzoic
acid in 60 mL water is calculated to be 94.9%. (AtQ5)

Sample Calculations

Percent Recovery:
𝑚
Actual Percent Recovery = 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑠 × 100
𝑚𝑐𝑟𝑢𝑑𝑒 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑
1.90 𝑔
= × 100
2.01𝑔
= 94.5 %

Percent Error of Melting Point of Benzoic Acid:


𝐸𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑉𝑎𝑙𝑢𝑒−𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑉𝑎𝑙𝑢𝑒
Percent Error = | | × 100
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑉𝑎𝑙𝑢𝑒
120.6 °C−122.4°C
=| | × 100
122.4°C
= 1.47 %

Maximum Theoretical Percent Recovery

Temperature Solubility of Benzoic Acid (in 100 mL of


water)
0 °C 0.17 g
100 °C 6.8 g

To obtain the maximum theoretical percent recovery from recrystallization of 2.0g of benzoic
acid in 60 mL water, convert 0.17g/100 mL solubility in terms of x g/60 mL.

0.17 𝑔 𝑥𝑔
=
100 𝑚𝐿 60 𝑚𝐿

x = 0.102 g
Therefore, x = 0.102 g/60 mL at 0 °C.

Since 0.102 g dissolved in the cold solvent,


mrecovered = 2.00 g – 0.102 g = 1.898 g
𝑚𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑠
Theoretical Percent Recovery = × 100
𝑚𝑐𝑟𝑢𝑑𝑒 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑
1.898 𝑔
=
2.00 𝑔
= 94.9 %
References

Department of Chemistry and Biochemistry, University of Colorado at Boulder; 2014 May


14 [cited 2014 June 19]. Available from: http://orgchem.colorado.edu/Technique/
Procedures/Crystallization/Crystallization.html.

Department of Chemistry, Stony Brook University; 2001 February 1 [cited 2005 May 22].
Available from: http://www.sinc.sunysb.edu/Class/orgolab/hotfiltration.PDF.

Fessenden RJ, Fessenden JS. Techniques and Experiments for Organic Chemistry. USA:
Merck & Co.; 1983.

Most CF. Experimental Organic Chemistry. USA: Wiley & Sons; 1988.

Why do impure solids melt at lower temperatures: Melting points explained. (2018, August
07). Retrieved from https://kirsoplabs.co.uk/lab-aids/impure-solids-melt-lower-temperatures/

National Center for Biotechnology Information. PubChem Compound Database; CID=243,


https://pubchem.ncbi.nlm.nih.gov/compound/243 (accessed Feb. 17, 2019).