Esterification of Salicylic Acid via Acetic Anhydride for the Pro- duction of Acetylsalicylic Anhydride (Aspirin)

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1 Esterification of Salicylic Acid via Acetic Anhydride for the Pro- duction of Acetylsalicylic Anhydride (Aspirin) Dana M. Feuerhammer Department of Chemistry, American University, Washington, D.C Date of Publication: February 25, 2014 ABSTRACT: This experiment utilized esterification and Le Chatelier s principle to create acetylsalicylic anhydride from salicylic acid, acetic anhydride, and the catalyst phosphoric acid g crude aspirin was obtained, with 4.908g recrystallized product and a 97.7% yield and 2.3% error. The TLC resulted in rf values of.83 for salicylic acid,.83 and.67 for crude product, and.67 for recrystallized product. These results formed the conclusion that pure aspirin was made. INTRODUCTION Acetylsalicylic acid, or aspirin, has been utilized as a pain reliever for centuries, first seen in ancient Rome and Greece. Salicin, an extract acquired from the bark of willow and poplar trees, was the first to be used as a pain reliever (analgesic). It was later found in the 19 th century that salicin is a glycoside formed from a molecule of salicylic acid and a sugar molecule and could therefore be utilized as a pain reliever. Unfortunately, salicylic acid attacks mucus molecules causing gastric pain, ulcers, and vomiting, but was improved with the addition of an acetyl group. Today, each tablet include 325mg of acetylsalicylic acid (1). Aspirin is a selective COX1 inhibitor that acts by acetylating a residue in the active site, irreversibly inactivating COX1, which in turn inhibits the production of Prostaglandins. Prostaglandins are fatty acid derivatives with inflammation, pain, and immune response effects, catalyzed by the enzyme cyclooxygenase (COX) from aracodonic acid. COX1 catalyzes thromboxane, a powerful platelet activator and blood vessel constrictor. With aspirin inhibiting COX1, this effect is reduced (2). Through this mechanism, aspirin can act as an anti-inflammatory, an analgesic, heart attack/stroke preventer, and an antipyretic. With a lack of platelet activation, aspirin acts as a blood thinner and therefore decreases the risk of clotting and its associated medical emergencies. Because prostaglandins are needed for pain response, aspirin s inhibition of COX creates pain relief. Prostaglandins are also responsible for signaling the hypothalamus to increase body temperature, and therefore aspirin acts as a fever reducer (3). Negative effects of aspirin include Reye s syndrome, blood thinning, and gastric disturbance. Reye s syndrome is a brain disorder that strikes children and persons under 18 who take aspirin after having the flu or chickenpox. In newborn babies and their mothers, the lack of clotting can cause uncontrolled bleeding. (1). For people with arthritis, the amount of aspirin needed daily for pain relief and to control inflammation creates gastric disturbance, but can be buffered out (3). To test for the purity of aspirin synthesized in lab, thin layer chromatography (TLC) is used. This is a capillary action technique where a polar silica-coated plate is dotted with the sample substances a half inch from the bottom of the paper and placed in a glass container with a saturating paper and solvent and covered. The samples will then rise through capillary action with the mobile front (polar, strong solvent), with the more polar substances interacting with the silica

2 more strongly and moving less far than a less polar substance (4). In this experiment, aspirin is synthesized using salicylic acid and acetic anhydride and then analyzed through TLC using a silica plate and an ethyl acetate-methylene chloride solvent. MATERIALS AND METHODS 2.0g of salicylic acid, 5.0 ml of acetic anhydride, and 5 drops of 85% phosphoric acid solution were added and swirled together under a fume hood in an Erlenmeyer flask. The flask was then placed in a 70C hot-water bath on a hot plate for about 15 minutes. The mixture was stirred occasionally and 2mL of distilled water was added after 10 minutes. When the vapors ceased indicating the completion of the reaction, the mixture was removed from the hot both and 20ml of distilled water was added and cooled to room temperature. Vacuum filtration was then used to dry the solution, occasionally rinsing the crystals with distilled water. The dried crystals were then massed and a small sample was set aside for later TLC analysis. 1g of remaining crude aspirin was used in re-crystallization, adding to 20mL of hot ethanol/water solvent over a warm water bath until the crystals dissolved, without boiling. The solution was then removed, covered, and allowed to slowly cool to room temperature when it was then placed in an ice bath. The pure crystals were then dried with a vacuum filter and rinsed with 3mL of ice-cold deionized water and 2mL of icecold ethanol. A TLC apparatus was then set up with a beaker and watch glass as a developing chamber, a silica gel coated plate as the stationary phase, and 10mL of 9:1 ethyl acetate methylene chloride mixture as the mobile phase. The silica paper was dotted with three substances: salicylic acid, crude product, and recrystallized product all dissolved in ~5 drops of solvent. The plate was placed in the developing chamber with a saturated paper, covered with a watch glass, and run until the mobile front reach ~1/2 inch from the top of the silica paper. The paper was then removed and analyzed under a black light. RESULTS Mass of salicylic acid used (g) Volume of acetic anhydride used (ml) Mass of acetic anhydride (g) Mass of aspirin & filter paper (g) Mass of filter paper (g).325 Mass of aspirin synthesized (g) Mass of recrystallized aspirin (g) Table 1: Raw Data Theoretical yield= moles of limiting reagent Eq. 1 Moles salicylic acid = 2.001g /138.12g mol = !limiting reagent Moles acetic anhydride= 5.4g /102.09gmol= Theoretical Yield= mols x gmol = 2.612g % Yield= (actual yield/theoretical yield) x100 Eq. 2 (2.551g/2.61g) x100= 97.7% % Error= ([theoretical-experimental)/theoretical] x100 Eq. 3 % Error= [(2.612g-2.551g)/2.612] x100 = 2.3% Theoretical Yield 2.162g % Yield 97.7 % % Error 2.3% Table 2: Calculated Data

3 Table 1 shows the raw data collected from this experiment. Equation 1 used this information to find the theoretical yield of aspirin, which is 2.162g. Equation 2 used Table 1 to find the percent yield, which is 97.7%. Equation 3 used Table 1 to find percent error, which is 2.3%. Table 2 displays the calculated data. Esterification is the acid catalyzed reaction of a carboxyl group and the OH group of an alcohol or phenol to form a carboxylate ester. This is an equilibrium reaction because as the reactants are used up and the products increase, the products react with one another to produce the original reactants (5). Control over this equilibrium derives from Le Chatelier s principle, which states that a system at equilibrium will adjust in order to minimize any stress placed on the system. In the case of aspirin, Le Chatlier s principle can be utilized to favor the products by adding water to the reactant side to debilitate the reactant acetic anhydride. In contrast, water can be added to the product side to favor the reactants (6). The formation of acetylsalicylic acid is an esterification. The acetyl group comes from acetic anhydride and the OH group is attached to the ring of salicylic acid (which also possesses a carboxyl group) (5). This esterification replaces the OH group with the acetyl group, making the product aspirin less acidic and therefore less problematic for the consumers gastric system. Figure 1: TLC RF= solute distance/solvent front distance SA= 1.25/1.5=.83 Crude= 1.25/1.5=.83 =1/1.5=.67 Recrystallized= 1/1.5=.67 Eq. 4 Figure 1 shows the TLC of salicylic acid (rf.83), crude product (rf.83 and.67), and recrystallized product (rf.67). The rf values were obtained using Equation 4. DISCUSSION

4 In the first step, the oxygen of the carbonyl of the acetic anhydride is protonated by the catalyst phosphoric acid. It is a strong acid (pka ~2.1) so there are many protons available. This protonation increases the electrophilicity of the carbon of that carbonyl. The oxygen of the phenol in salicylic acid acts as a nucleophile and attacks the carbon of the carbonyl acting as the electrophile within acetic anhydride, simultaneously breaking the pi bond to oxygen, and forming a tetrahedral intermediate. A proton transfer then occurs releasing that hydrogen from the previously protonated oxygen. The other free oxygen on the original acetic anhydride atom is then protonated, which causes a lone pair of electrons to form a pi bond with the carbon holding the OH group. This transfer allows the acetic anhydride to leave. A final proton transfer to eliminate the positive charge on the double bonded C-O forms the final aspirin product. Phosphoric acid is used as a catalyst in this reaction. It is needed to protonate acetic anhydride in order to withdraw the positive charge from the central carbon and make it a good electrophile for the salicylic acid to attack. The reaction is heated to 70-80C to increase the rate of reaction between salicylic and acetic anhydride. Without heating, the molecules would not excite or react and little to no reaction would occur. After minutes of heating, water was added to not only re-crystalize the product, but also to destroy any remaining acetic anhydride and turn it into acetic acid. The H20 adds across the anhydride bridge, cleaving it to release two acetic acid molecules, which are much less reactive than acetic anhydride (5). The crude aspirin was dissolved in hot water/ethanol mixture because salicylic acid and aspirin are only slightly soluble at room temperature, but very soluble when heated. The crude aspirin was not clean from re-crystallization earlier because the salicylic acid also recrystallized. The addition of heat therefore separates these two substances further. According to the TLC plate obtained, aspirin was made. In the salicylic acid, the rf value was recorded to be.83, representing the least polar alcohol functional group. This rf value is still shown in the crude product, but there is also another peak with an rf value of.67 representing the equilibrium reaction keeping reactants around as well as the product of aspirin with its new acetyl group. The final recrystallized product only displays an rf value of.67, which indicates that all OH groups were replaced by a more polar, less-traveling acetyl group. One reason why this experiment did not have given a 100% yield is that the solution was not left in the ice water bath, therefore not letting the full amount of crystals to form. Another reason is that this is an equilibrium reaction, so without the proper amount of water added to the reactants to favor the products, the products could have reacted and reduced the % yield (5). CONCLUSION This experiment gave a 97.7% yield with a 2.3% error and a TLC plate displaying pure aspirin with no trace of salicylic acid. This indicates that the salicylic acid was successfully esterificated by acetic anhydride catalyzed by phosphoric acid, eliminating the acidic OH group and leaving a less harmful product for consumers. In future replications of this experiment, it would be recommended that the final product be left to dry overnight in order to get a more accurate final weight of the product and avoid miscalculations of percent yield. REFERENCES 1. Williamson, K.; Masters, K. Macroscale and Microscale Organic Experiments 6e Farragher, K.; Stanford, J.; Murphy, P.; Keenan, P Aspirin Foundation

5 3. Wiley, J. Interactive Concepts in Biochemistry 2006 Section X 4. Rosen, J., Gothard, Q. Science Online: Facts on File 2011 Chromatography 5. Snelling, C.R. Synthesis of Aspirin 2013 Volstate Education 6. Klein, David Organic Chemistry ACKNOWLEDGMENTS Acknowledgement is due to Dr. Dehghan and American University for providing the guidance and supplies to make this experiment successful. This assignment is my own work and I have cited all material used in its preparation. This assignment has not previously been submitted at any other time or any other course. I have not copied in part or whole the work of other students or person. SIGNATURE DATE

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