synthesis of aspirin project

Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. Patented by Bayer in 1893! When the aspirin was prepared, it was isolated and filtered. Citric acid and pineapple juice were used as possible green catalysts but only citric acid worked when used in a high concentration. 8. Also, your melting point range may be greater than 2 degrees. Introduction: Charles Frederic Gerhardt, a French chemist was the first to prepare aspirin in 1853. In this case, one molecule (salicylic acid) provides both the "alcohol" and the carboxylic acid. Reactions: Procedure and Results: Aspirin Synthesis Tap water was heated on a steam bath in a 250 mL beaker. 3. James Chickos, David Garin, and Valerian D'Souza. In this experiment aspirin was synthesized from salicylic acid and acetic anhydride. Synthesis of Aspirin: A General Chemistry Experiment Olmsted, John A., III An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. Synthesis of Aspirin 1618 Words | 7 Pages. Right click a data point and select add trend line. Antipyretic (fever reducer)! In lower doses, aspirin … German chemist Felix Hoffman was the first to experiment in the synthesizing of aspirin and was credited with the success of the revolutionary drug. Record the weight of the crude solid which probably contains water. What is the theoretical yield of aspirin (in two significant figures). ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). Activity 1: Synthesis of Aspirin. Highlight the data and select insert, and scatter (w/ only markers). An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. After synthesis and analysis, it will be deter-mined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both (3). 11. In this experiment, phosphoric acid will be used as the catalyst. Normally, you measure reactants to at least two significant figures. Polyesters are often made from dicarboxylic acids and diols. Furthermore, the other objectives were to enable students to conduct the synthesis of aspirin, reinforce skills or recrystallisation and the technique of melting point determination. Aspirin Aspirin is synthesized by the acetylation of salicylic acid using acetic anhydride or acetyl chloride. A “purified product” can be obtained through recrystallization of the crude product in hot ethanol. Over history, many compounds obtained from nature have been used to cure ills or to produce an effect in humans. The theoretical (maximum) yield is 3.9 grams. But still a very large part of the world’s population has inadequate or no access to such essential and life-saving medicines like acetyl-salicylic acid. Filter the solution through a Buchner funnel to remove any insoluble impurities or polymers that may have been formed. Overall findings The two methods were duplicated giving the following results; The Merck Index, which is an encyclopedia of chemicals, drugs and biologicals, lists the following information under aspirin: acetylsalicylic acid; monoclinic tablets or needle-like crystals; mp 135 °C (rapid heating); is odorless, but in moist air it is gradually hydrolyzed into salicylic and acetic acids; one gram dissolves in 300 mL of water at 25 °C, in 100 mL of water at 37 °C, in 5 mL alcohol, in 17 mL chloroform. These natural products have been obtained from plants, minerals, and animals. Aspirin Synthesis Materials . Carefully pour the filtrate with stirring, a small amount at a time, into an ice cold HCl solution (, Filter the solid by suction and wash the crystals 3X with 5 mL of. Major Chemical Concept. 4. If crystals do not appear, you can scratch the walls of the flask with a stirring rod to induce crystallization. If impurities are present in your crude sample, the melting point range for your product will be lower than the range of pure aspirin. Be sure to wear gloves and safety goggles when using these chemicals. Clearly state if the samples are below the maximum allowable limit for percent salicylic acid (0.15 %). 9. This video shows how to synthesize aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. This reaction is the reverse of the synthesis reaction. A “purified product” can be obtained through recrystallization of the crude product in hot ethanol. The melting point range of pure aspirin is 138-140 C and the melting point range of the salicylic acid starting material is 158-161 C. Legal. NSF CCLI Project Page 1 EXPERIMENT Aspirin: Synthesis and NMR Analysis Introduction: When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is produced according to the following equation. Adopted a LibreTexts for your class? To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. Synthesis of Aspirin. 2-hydroxybenzoic acid, which is the main metabolite of aspirin, shows it is also molecularly lighter (in that it is moved further up the paper when soluble) than crude aspirin or pure aspirin. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. Louis; Chemistry). University of Missouri–St. The purity of the product is confirmed by measuring its melting point range. The maximum allowable amount of free salicylic acid in an aspirin sample is 0.15% salicylic acid. Rinse the crystals several times with small portions (5 mL) of cold water and air dry the crystals on a Buchner funnel by suction until the crystals appear to be free of solvent. The synthesis reaction of aspirin is shown below: Since acetic acid is very soluble in water, it is easily separated from the aspirin product. The purity of the product as a pharmaceutical is crucial, and Determination Of The Contents Of Cold Drinks. Still in the hood, heat the mixture for about 10 min. If you spill a lot of either of these, notify your instructor. During this semester, you will have an opportunity to isolate some pharmacologically active natural products and to synthesize other active compounds from suitable starting materials. One popular drug that does both is aspirin. CONTINUED… 1) Substitution on carboxyl groups may affect the potency and toxicity. The product will appear as a solid mass when crystallization is completed. Measure the melting point range with the Meltemp Apparatus (your instructor will demonstrate) and compare to the value for pure aspirin of 138-140 oC. You can use some of the filtrate to rinse the Erlenmeyer flask if necessary. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. Collect the product by vacuum filtration and rinse out of the flask with a few milliliters of cold petroleum ether. 2) Reducing the acidity of the –COOH, retains the analgesic action of salicylic acid , but it is devoid of the anti- inflammatory properties. A polymeric material, which is a polyester, is formed in this reaction. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. 3.0 g salicylic acid; 6 mL acetic anhydride* 5-8 drops of 85% phosphoric acid or concentrated sulfuric acid* Distilled water (about 50 mL) 10 … Allow the air to be drawn through the solid and filter paper for 15 minutes. In the 5th century B.C., Hippocrates ground the bark into a powder, and later, the Natives Americans chewed on the bark to alleviate fever and pain1. 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