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Name: Eghan Kojo Experiment N 0 : O 2.2.

2 Graduate Assistant: Emmanuel Kwakye Boakye Date: 26 th February, 2013 TITLE: THE PREPARATION OF A COMMERCIALLY IMPORTANT ESTER AIMS 1. To synthesize and purify acetyl salicylic acid 2. To calculate the percentage yield of the product. INTRODUCTION Esters are an important class of organic chemical compounds. Two common esters, acetylsalicylic acid and methyl salicylate, are very important over-the-counter drugs. Since ancient times, it has been known that the barks of certain trees, when chewed or brewed as a tea, had analgesic (pain-killing) and antipyretic (Feverreducing) properties. The active ingredient in such barks was determined to be salicylic acid. When pure salicylic acid was isolated by chemists, however, it probed to be much too harsh to the linings of the mouth, esophagus, and stomach for direct use as a drug in the pure state. Salicylic acid contains the phenolic (-OH) functional group in addition to the carboxyl (acid) group, and it is the combination of these two groups that leads to the harshness of salicylic acid on the digestive tract. Esters were traditionally named by combining the name of the alcohol with the root name of the acid and adding “ate” as a suffix. Traditional names are still widely used by most chemists, particularly for the simple esters. The IUPAC naming system uses the systematic names for the alcohol and root name of the acid, followed by “oate.” Salicylic acid is the active ingredient in willow bark, which Hippocrates (5th century BCE) knew to reduce aches and pains and fever. This remedy was also mentioned in texts from ancient Sumer, Lebanon, and Assyria. The medicinal character of methyl salicylate arises from its ready hydrolysis to salicylic acid in the gut. The medicinal properties of aspirin, acetyl salicylic acid, are also due to its ready hydrolysis to salicylic acid. Methyl salicylate can be taken internally or absorbed through the skin. This ester also has a pleasant odor, and it is used to a small extent as a flavoring principle. Because salicylic acid contains both the organic acid group (-COOH) as well as the phenolic group (OH), salicylic acid is capable of undergoing two separate esterification reactions, depending on whether it is behaving as an acid (through the –COOH) or as an alcohol analog (through the –OH). Research was conducted in an attempt to modify the salicylic acid molecule in such a manner that its desirable analgesic and antipyretic properties would be preserved, but its harshness to the digestive system would be decreased. The Bayer Company of Germany, in the late 1800s, patented an ester of salicylic said that had been produced by reaction of salicylic acid with acetic acid. The ester, commonly called acetylsalicylic acid, or by its original trace name (aspirin), no longer has the phenolic functional group. The salicylic acid has acted as an alcohol when reacted with acetic acid. Acetylsalicylic acid is much less harsh to the digestive system. When acetylsalicylic acid reaches the intestinal tract, however, the basic environment of the small intestine causes hydrolysis of the ester (the reverse of the

4. The minty odor of many common liniments sold for sore muscles and joints is due to this ester. the scent and taste of strawberries is due to the presence of methyl cinnamate. Acetylsalicylic acid is converted back into salicylic acid in the small intestine and is then absorbed into the bloodstream in that form. Since the other component in the production of acetylsalicylic acid is acetic acid. When salicylic acid is heated with methyl alcohol. 3. 5. Acetic acid anhydride Concentrated sulphric acid Salicylic acid Distilled water Iced water APPARATUS 1. and causes a sensation of warmth to the area of the skin where it is applied.esterification reaction) to occur. Aspirin tablets sold commercially generally contain binders (such as starch) that help keep the tablets dry and prevent the acetylsalicylic acid in the tablets from decomposing into salicylic acid. and benzyl acetate CHEMICALS 1. This is usually considered to be a desirable property of the ester. Methyl salicylate is a skin irritant. For example. 2. Esters typically have strong. however. often pleasant. 3. the carboxyl group of salicylic acid is esterified. 2. one indication that aspirin tablets have decomposed is and odor of vinegar from the acetic acid released by the hydrolysis. ethyl butyrate. C7H6O3 + C4H6O3 → C9H8O4 + C2H4O2 The second common ester of salicylic acid that is used as a drug is methyl salicylate. Methyl salicylate is also used as a flavoring/aroma agent in various products and is referred to commercially as oil of wintergreen. either individually or in combination. so many esters are used as flavorings and perfume agents. isobutyl acetate. Methyl salicylate is absorbed through the skin when applied topically and may permit the pain-killing properties of salicylic acid to be localized on the irritated area. ethyl caproate. 4. scents and tastes. Water bath 50ml measuring cylinder 25ml measuring cylinder Stirring rod . producing a strong-smelling liquid ester (methyl salicylate).

1 gm/mole Molar mass of acetic anhydride = 102 gm/mole. A clear solution was obtained with evolution of a gas with a sharp smell. Spatula 6. The solution was heated for about 20 minutes 25ml of cold water was added to the solution slowly and a further 50ml was added.065g Mass of only crystals Actual yield is 4.065g. The sample dissolved.0 ml acetic anhydride x 1.0g.985g .1 = 0. CALCULATIONS Mass of filter paper = 1. = 6. 1. Mass of crystals obtained = 6.656 gm/102 = 0.082 gm/ml = 8.085 moles Therefore the limiting reactant is salicylic acid and acetic anhydride is in excess.08g OBSERVATION The electronic balance recorded a weight of 1.00gm/138. The electronic balance recorded a weight of 4. Sulphric acid was added to the salicylic acid in the flask.08g. 8ml of acetic acid anhydride and 7 drops of conc. White chalky precipitate was formed which thickened gradually.08g is 4.029 moles salicylic acid 8.082gm/ml density Molar mass of aspirin = 180.065g . Electronic balance PROCEDURE STEP A dry filter paper was weighed on an electronic balance A distillation flask was weighed and the electronic balance tared. An amount of salicylic acid was put in it and the weight recorded.2 gm/mole 4.0g and that of the filter paper and the sample 6.1. The precipitate was filtered using a vacuum pump and dried and the weight taken.0g Salicylic acid + acetic → anhydride aspirin + acetic acid The mole ratios are 1:1:1 so one mole salicylic acid reacts with one mole acetic anhydride to produce one mole of aspirin. The weight of dry filter paper was 1.5. Molar mass of salicylic acid = 138.

085 moles. Sufficient heat was applied for the reaction to proceed more effectively.16% DISCUSSION It is possible to prepare esters using either the acid or the anhydride of the acid together with the Alcohol. All acid additions were done in the fume hood. Energy had to be applied to the mixture of salicylic acid and acetic anhydride so that the reacting molecules will collide with enough force to disintegrate their bonds to form newer bonds for the formation of the product.2gm/mole x 0. ERROR ANALYSIS 1. the sample was dried using a vacuum pump before the experiment continued. PRECAUTIONS 1.292 gms Theoretical yield = 15.085 moles = 15. since they were exothermic reactions 2. The other part of the acetic anhydride reacts to produce the byproduct acetic acid. After the additions of cold water. The synthesis process used in the commercial preparation of Acetylsalicylic acid was carried out. The sample was changed from the aqueous form to a solid from with the use of the vacuum pump to extract all moisture content making it readily available for weighing. it was only used as a catalyst. Impurities might have gotten into contact with the sample and had reacted and may have reduced its weight. this helps in obtaining a powered form of the product. CONCLUSION . Acid anhydrides are much more reactive than the free acid. The heating of the sample was done in the water bath to prevent too much heat from attacking the sample since if too much heat is applied the formation of the product will be impossible. Hence the test for purity was not done. An esterification reaction occurs where the hydroxyl group functional group reacts with part of the acetic anhydride to form an ester in the acetylsalicylic acid product. 2. There were no capillary tubes and thermometers provided to measure the melting point of the sample. Cold water was added to the sample to break up any lumps present.292 %Yield = %Yield = %Yield = 26. It didn’t take part in the reaction.The most aspirin that can be made under these conditions is 0. Sulfuric acid was added to the beaker after the addition of salicylic acid and acetic anhydride to allow the reaction to proceed to completion with ease. 3. 180.

Pflügers Archiv: European Journal of Physiology Pages 527–546 . "Aspirin and clopidogrel resistance: an emerging clinical entity. often used as an analgesic to relieve minor aches and pains. Wang. Michael B. Smith. Mechanisms. DL.16%.” European heart journal 27 Pages 647–654 5. Palleros. (1901). Experimental Organic Chemistry.). TH. Lide.. R.292g.0g and the theoretical yield was calculated to be 15. giving rise to a percentage yield of 26.. EJ (March 2006). (2000). Topol. March. Advanced Organic Chemistry: Reactions. Jerry (2007).). Singer. REFERENCES 1. "Ueber Aspirin". Boca Raton (FL): CRC Press. H. CRC Handbook of Chemistry and Physics (86th Ed. D. Page 494 3. as an antipyretic to reduce fever. Daniel R.Acetylsalicylic acid know commercially as aspirin. ed. New York: John Wiley & Sons. (2005). and Structure (6th ed. The Actual yield is 4. and as an anti-inflammatory medication was produced. Bhatt. 4. New York: Wiley-Interscience 2.