SUBLIMATION AND MELTING POINT DETERMINATION OF IMPURE BENZOIC ACID Clarisse Anne S. Caganda, Jan Vincent M.

Calalang, Joanna Marie A. Carranceja, Hubert Constantin Chua, Stevenz A. Cirujales Group 2 2A Pharmacy Organic Chemistry Laboratory ABSTRACT
The experiment was conducted to determine the purity of benzoic acid through sublimation and melting point determination of its crude form, impure benzoic acid. In the process of sublimation, formations of crystals were observed in the inverted watch glass. The crystals collected (sublimate) and the pure benzoic acid are then individually packed in capillary tubes which are then used in determining the said substances melting point through the use of an oil bath. The melting point value of impure benzoic acid is compared to the standard value of pure benzoic acid, 122C. From the collected data, the students were able to identify the purity of the compound and compute the percentage recovery in the experiment.

INTRODUCTION
Sublimation is the term used in describing the phase change of solid to gas. This process does not pass through a liquid phase between the two phases mentioned. The vapor from the gaseous phase can solidify, making sublimation a purification process. By this, it is then defined as a technique used to purify solid mixtures. However, this definition is only limited for those having impurities which are non-volatile or that having lower vapor pressure than the pure compound. On the other hand, sublimation is not only limited to its purification properties. It is also used to describe the reverse process of the gas changing to its solid state again upon cooling. Sublimation also occurs when air saturated with water vapor is suddenly cooled below the freezing point of water. Often associated with sublimation is melting point determination which aims to test the purity of the compound. Melting point is defined as the temperature at which its solid and liquid phases coexist in equilibrium. The normal melting point of a substance is its melting point at one atmosphere pressure. Changes in pressure have very small effects on melting points, but they have large effects on boiling points. An oil bath was used during the process; it was preferred from a water bath mainly because the melting point of benzoic acid is higher than the boiling point of water. Benzoic Acid is the compound used for the experiment. It is considered as the simplest aromatic carboxylic acid containing carboxyl group bonded directly to a benzene ring. It is a white and crystalline organic compound that has a melting point of 122 C and a boiling point at 247 C. It occurs naturally in many plants and resins. It is also used as a microbial agent in toothpastes, mouthwashes, cosmetics and deodorants. Benzoic acid in its Fig 1. Structure of Benzoic Acid crude form is called impure benzoic acid. The formation of benzoic acid takes place because of the oxidation of toluene. The process of oxidation needs to be carried out in the liquid phase of the compound and is only possible in the presence of a catalyst. The impurities present in the newly formed

benzene in this process are because of phenyl and benzyl compounds that seriously affect the product. These impurities also have amino compounds that are present in a larger extent inside impure benzene. The objectives of the experiment were to purify benzoic acid by sublimation, determine and compare the melting point of the product with a standard and calculate the percentage recovery. EXPERIMENTAL PROCEDURE During the process of sublimation, 5g of impure benzoic acid was weighed in an evaporating dish and was covered with a perforated filter paper. An inverted watch glass, which was pre-weighed, was fastened to the setup using a masking tape to serve as a cover. A moistened tissue paper was put on top of the watch glass. For 15 minutes, it was heated in a hot plate and after, allowed to cool to room temperature. Fig 2. Sublimation Set-up After letting it stand, the sublimate found in the inverted watch glass and perforated filter paper were collected and weighed in the same weighing scale used for pre-weighing of the watch glass used in the setup. From the data collected, the percentage recovery was calculated. For melting point determination, the sublimate was grinded into a fine powder using a mortar and a pestle. After which, it was packed into a capillary tube. To ensure that the powder is tightly packed together, the closed end of the capillary tube was dropped several times in a glass tubing until it was well-packed with 3-5mm of the sublimate. To serve as a standard of reference, pure benzoic acid was weighed and was also made well-packed in capillary tubes. An oil bath setup was then assembled. The capillary tubes were attached to a thermometer using a rubber band, its closed end attached to the mercury bulb of the

thermometer. With the capillary tubes immersed in the oil bath, it was then heated. The students recorded the temperature at which both compounds started to melt and the temperature at which both has completely melted.

Impure benzoic acid is the crude form of benzoic acid. Meaning to say, impure benzoic acid contains impurities such as phenyl and benzyl. Also, it contains amino compounds. The essence of computing for the percentage recovery is to find out how impure the initial sample is. Based from the data collected before and after the sublimation process, the percentage recovery was computed. It is computed using the values of the weight of the sublimate over the weight of the initial sample, impure benzoic acid. It is then multiplied to 100 to indicate its percentage. Based on Table 1, the data here shows that there was .4 g of the sublimate and 5 g of the impure benzoic acid. Using the formula for percentage recovery, it indicates that only 8% was recovered. Meaning to say, 92% of the initial sample was made up of impurities.

RESULTS AND DISCUSSIONS Sublimation Sublimation occurs to solids that can pass into the vapor phase without having to pass through the liquid phase. It occurs when the vapor pressure of a substance is greater than the atmospheric pressure at the melting point. Given the fact that the vapor can solidify, sublimation may be an effective purification process. It can be therefore defined as a technique used to purify solid mixtures. It is only limited, however, to those with nonvolatile impurities or those that have lower vapor pressure than the pure compound. Table 1 includes the data needed for the computation of the Percentage Recovery of benzoic acid after the sublimation process.

Melting Point Determination Melting point is the specific range of temperature where a substance starts to melt until it has completely melted. It is also defined as the temperature at which its solid and liquid phases coexist in equilibrium. For this, an oil bath setup was used. In contrast to a water bath, an oil bath was preferred because the melting point of benzoic acid is higher than the boiling point of water. After packing the sublimate and the pure benzoic acid in individual capillary tubes, it was attached in a thermometer and immersed in the oil bath. The temperature at which the two started to melt and at which the two substances completely melted was noted. Table 2 notes the differences of the sublimate and the pure benzoic acid to the temperature at which they have started and completed melting. Temperature 1st Reading Pure Benzoic Acid Sublimate 113C 2nd Reading 124C Average 118.5C

Weight of the Impure Benzoic Acid Weight of the Watch Glass + Sublimate Weight of the Watch Glass (empty) Weight of the Sublimate

5.0 g 122.9 g 122.5 g .4 g

Table 1. Data Collected from the Sublimation Process Initially, 5 g of impure benzoic acid was weighed and had undergone the sublimation process. A watch glass was preweighed and was found to be weighing 122.5 g. This watch glass served as the cover for the setup. Also, this is where the sublimate is contained after the sublimation process. After the said process, the watch glass was again weighed and was found to be weighing 122.9 g. This means that the sublimate weighs only .4 g. From the data collected, the Percentage Recovery may be computed:

115C

127C

121C

The 1st Reading indicates the temperature at which the two compounds started to melt. Pure benzoic acid started to melt at 113C, while the collected sublimate started to melt at 115C. The 2 nd Reading indicates the temperature at which the two has completely melted, pure benzoic acid melted completely at 124C, and the sublimate completely melted at 127C. The average value shows the melting

point of the substances 118C for pure benzoic acid and 121C for the sublimate. Pure benzoic acid is known to have a melting point of 122C. There is a 3.5 difference between the standard melting point and the average melting point of the compound in the experiment. Certain deviations on melting point have occurred maybe because of mishandlings and contaminations.

REFERENCES: Internet Sites: http://www.chemicalland21.com/industrialchem/organic/b enzoic%20acid.htm http://www.ehow.com/about_6629946_impure-benzoicacid_.html http://physics.about.com/od/glossary/g/sublimation.htm http://www.infoplease.com/ce6/sci/A0847062.html

Books:
Bayquen A. (2009). Laboratory Manual in Organic Chemistry. Quezon City. C&E Publishing, Inc. Whitten, Davis, Peck, Stanley (2010). Chemistry. 9 th Edition. USA: Brooks/Cole