SUBLIMATION AND MELTING POINT DETERMINATION OF BENZOIC ACID Christine E. Reyno, Jericho E. Rivera, Theresa P. Rivera, Marjorie A.

Roo, Chelsea G. Rubio, and Khristine A. Salamat Group 7 2C-Medical Technology Organic Chemistry Laboratory ABSTRACT
An impure benzoic acid was compassed through sublimation. The objectives of this experiment were to purify the benzoic acid by sublimation, determine and compare the melting point of the sublimate with the standard and calculate the percentage recovery of the sublimate. Five grams of impure benzoic acid was prepared for sublimation. After the sublimation set-up was assembled, the sample was heated for 10-15 minutes and was allowed to cool down. Subsequently, the sublimate was collected and weighed. The percentage recovery of the sublimate was calculated. For the melting point determination, the sublimate and standard were ground and packed in separate capillary tubes. Both tubes were attached to a thermometer and were immersed in an oil bath until both substances melt. The temperature of initial and final melting point of the substances was tracked and recorded. Based on the results, the percentage recovery of the sublimate is 32% and the sublimate produced was still impure for the range of its melting point is greater than 2oC.

INTRODUCTION
Sublimation is the process whereby a solid evaporates from a warm surface and condenses on a cold surface, again as a solid. This technique is particularly useful for the small-scale purification of solids because there is so little loss of material in transfer. [1] This process occurs if the vapor pressure of a substance is greater than the atmospheric pressure at the melting point. Since the vapor can solidify, the vaporization-solidification cycle can be used as a purification process. Sublimation, therefore, is a technique used to purify solid mixtures. The purification, however, can only be done if the impurities are non-volatile or have significantly lower vapor pressure than the pure compound. [2] The melting point (freezing point) of a substance is the temperature at which its solid and liquid phases coexist in equilibrium. It is the temperature at which the rate of melting of a solid is the same as the rate of freezing of its liquid under a given applied pressure. [3] There are different ways to determine the melting point of a certain substance. But, most melting point determination requires capillary tubes. Furthermore, melting points can also be a criterion of purity. The objectives of this experiment were to purify the impure benzoic acid through sublimation, to determine if the purification was successful by comparing the melting point of the sublimate and the standard and observe the effect of the purity of a substance on its melting behavior, to compute for the percent recovery of the sublimate.

B. Procedure 1. Sublimation
First, the sublimation set-up was assembled. The set-up consisted of the following: a) 5g of impure benzoic acid, b) evaporating dish, c) perforated filter paper, d) pre-weighed watch glass, and e) hot plate. Five grams of impure benzoic acid was placed on an evaporating dish. Then it was covered with a perforated filter paper and an inverted watch glass. It was fastened together to make sure that no vapor would escape during sublimation. A moistened tissue paper was put on top of the glass in order to prevent excessive heat. The set-up was placed in the hot plate and was heated for 10-15 minutes.

Figure 1. Sublimation Set-up After heating, the set-up was cooled to room temperature and the entire sublimate produced was collected and weighed. Then, the percentage recovery was calculated.

EXPERIMENTAL A. Compounds tested (or Samples used)

Impure Benzoic Acid (Sample), Pure Benzoic Acid (Standard)

2. Melting Point Determination

Following the collection of the sublimate, the pure and impure benzoic acid was prepared for melting point determination. Both substances were ground and placed into separate capillary tubes. The closed ends of both capillary tubes

were dropped down through a glass tubing several times to ensure that the substances were well packed. Afterwards, the melting point set-up was prepared.

Empty watch glass Sublimate

101.50 g 1.60 g

Formulae and Computations: Weight of Sublimate = = 103.10 g -101.50 g = 1.60 g To compute for the weight of the sublimate, the weight of the watch glass, 101.50 g, was subtracted to the weight of watch glass with the sublimate, 103.10 g that yields 1.60g. Thus, the weight of the sublimate is 1. 60 g. Table 2. Percentage Recovery of Sublimate
Result Percentage recovery 32%

Thermometer Iron clamp

Copper wire Beaker Capillary tubes w/ substances Oil Wire Gauze Iron ring Bunsen Burner

Percentage recovery=

Iron stand

Figure 2. Melting Point Set-up The set-up includes the following materials: a) iron stand and clamp, b) iron ring, c) thermometer, d) wire gauze, e) rubber band, f) unused cooking oil, g) samples packed in capillary tubes, h) copper wire, i) beaker, and j) Bunsen burner. The closed ends of both capillary tubes, aligned with the mercury bulb of the thermometer, were attached to the thermometer using the rubber band and were immersed in the oil bath. The oil bath was stirred constantly using the copper wire. Both the temperature and capillary tubes were monitored for melting point indications. Temperatures were obtained from the point where the substances started to melt until both have completely melted.

Percentage recovery is the percentage of pure substance extracted from the impure substance. The percentage recovery of the sublimate was computed by dividing 1.60g, the weight of sublimate over 5.00, weight of the impure benzoic acid. The quotient was then multiplied to 100 to get the percentage. The percentage recovery of the sublimate was 32% which meant that 32% of the benzoic acid was recovered from the 5 g impure benzoic acid. Having a high percentage recovery meant that the substance was close to being pure, if not completely pure. 2. Melting point determination Table 3. Data and Results for Melting Point Determination
Substances Sublimate Pure Benzoic Acid Initial Temperature (oC) 120 121 Final Temperature (oC) 130 129

RESULTS AND DISCUSSION

1. Sublimation Table 1. Data and Results for Sublimation
Variables Measured Impure Benzoic acid Watch glass and sublimate Weight 5.00 g 103.10 g

At 120oC, the sublimate started to melt and it completely melted at 130oC. On the other hand, the pure benzoic acid started to melt at 121oC and it completely melted at 129oC. Oil bath was preferred in this experiment because its melting point is greater than that of water. Thus, it provides a higher temperature and boiling point for the setup. From the data, the melting range of the impure benzoic acid was quite far to each other (10oC). The sublimate produced is still impure for the

difference in its initial and final melting point is greater than 2oC. Thus, this proved that melting point determination would help in determining if the purification was successful. Pure samples usually have sharp melting points (a melting range of less than about 1C); impure samples of the same compounds melt at lower temperatures and over a wider range. [4] iiiiVarious sources of error couldve affected the purification of the impure benzoic acid. First, was that not all of the crystals of sublimate had been recovered. Second, was the substances in the capillary tubes were too coarse, they did not pack well, causing air pockets to slow heat transfer. [5] Another one could be not all of the impure benzoic acid had gone into the process of sublimation.

CONCLUSION
iiiIn conclusion, sublimation is one way of purifying benzoic acid. The percentage recovery of the sublimate may determine if the substance produced was pure or not. The percentage recovery produced in this experiment was 32%. Moreover, melting points can also be a criterion of purity. Substances with melting range between 1-2C are pure substances while substances with a melting range greater than 2C are considered impure. Thus, the sublimate produced was still impure for its melting range is 10C.

REFERENCES
[1] Masters, K.M., Minard, R.D. & Williamson, K.L. (2007). Macroscale and Microscale Organic Experiments. 5th ed. Houghton Mifflin Company. [2] Bayquen A., et. al. (2009). Laboratory Manual in Organic Chemistry. Quezon City: C & E Publishing , Inc. [3] Davis, R., Peck, L., Stanley, G., Whitten, K. (2010). Chemistry. 9th ed. Canada: Brooks/ Cole. [4] Organic Laboratory Techniques 4. http://www.chem.ucalgary.ca/courses/351/l aboratory/meltingpoint.pdf 08/29/13 [5] Determination of Melting and Boiling Points . http://www.chemistry.sc.chula.ac.th/bsac/Or g%20Chem%20Lab_2012/Exp.1%5B1%5D. pdf 8/30/13