synthesis of aspirin project

The synthesis of aspirin is how You make it in a chemical lab or a chemical plant. 2) Reducing the acidity of the –COOH, retains the analgesic action of salicylic acid , but it is devoid of the anti- inflammatory properties. Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. Salicylic acid, through acetylation, gives acetylsalicylic acid, known as Aspirin… For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. The liquid is mostly water and can be washed down the sink. What is the theoretical yield of aspirin (in two significant figures). The synthesis reaction of aspirin is shown below: Since acetic acid is very soluble in water, it is easily separated from the aspirin product. 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). The product will be analyzed by three different methods: melting point, titration, and spectroscopic assay. Use them in the hood. Aspirin is used in the treatment of migraine • Aspirin is an important part of treatment of those who have had a myocardial infraction (heart attack). Aspirin Synthesis Materials . Put the dry aspirin and the filter paper into a pre-weighed plastic bag and weigh again. The experimental melting point range of aspirin was determined to be 122 -132°C. Patented by Bayer in 1893! A useful synthesis of acetylsalicylic acid was developed in 1893, patented in 1899, marketed under the trade name of “aspirin” by the Bayer Company in Germany. The impure (crude) aspirin was powered and fluffy with small clumps and was slightly yellow in colour whereas the pure aspirin has … A small amount of a strong acid is used as a catalyst which speeds up the reaction. Major Chemical Concept. 8. Cool the solution to room temperature and then in a ice-bath. 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. In addition, various transformations of these and other compounds have led to even more medically useful compounds. What percent of this did you get? Figure 1: Synthesis of aspirin (Clayden, et al., 558). This experiment uses salicylic acid, acetic anhydride and phosphoric acid. This will convert the acetic anhydride to vinegar and dilute the phosphoric acid. Reactions: Procedure and Results: Aspirin Synthesis Tap water was heated on a steam bath in a 250 mL beaker. 7. Carefully add 5 to 10 drops of 85% phosphoric acid, a catalyst, to the flask and swirl to mix everything thoroughly. 1. If impurities are present in your crude sample, the melting point range for your product will be lower than the range of pure aspirin. Determination Of The Contents Of Cold Drinks. 5. [ "article:topic", "Aspirin", "showtoc:no" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FAncillary_Materials%2FLaboratory_Experiments%2FWet_Lab_Experiments%2FOrganic_Chemistry_Labs%2FExperiments%2F1%253A__Synthesis_of_Aspirin_(Experiment), 2: Synthesis of Acetaminophen (Experiment), SYNTHESIS OF ASPIRIN (acetylsalicylic acid), information contact us at info@libretexts.org, status page at https://status.libretexts.org. These natural products have been obtained from plants, minerals, and animals. A “purified product” can be obtained through recrystallization of the crude product in hot ethanol. Calculate the weight of your product by subtracting the weight of the paper and bag from the total. Medicine Analysis – Synthesising Aspirin results After recrystallisation differences between the crude and purified aspirin were noted. Wash the crystals with 2-3 ml of chilled water. Determine the moles of aspirin from the titration and calculate the percent purity of the crude aspirin product from the titration analysis. 9. Next add 20 ml of distilled water and cool in an ice bath. The purity of the product as a pharmaceutical is crucial, and 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. Level. Submit the crystalline sample in a small vial with proper labeling to your instructor. Still in the hood, heat the mixture for about 10 min. In lower doses, aspirin … H. Heat the flask gently on the steam bath for at least 10 minutes. This is a popular concept among students for the chemistry project for class 12. Overall findings The two methods were duplicated giving the following results; The synthesis involved the reaction of salicylic acid and acetic anhydride in the presence of a catalyst, phosphoric acid, H3PO4. Why is it not necessary to measure the volume of acetic anhydride to two significant figures? In this experiment, the crude product will be the desired product. According to the data in the Merck Index, if 1.0 g of aspirin is dissolved in 100 mL of water at 37 °C , how much aspirin will precipitate out of solution when it is cooled to 25. objective was to convert a specific amount of salicylic acid into the same amount of aspirin that was high in purity. in a beaker of warm water (70-80 oC). Introduction: Charles Frederic Gerhardt, a French chemist was the first to prepare aspirin in 1853. In this experiment aspirin was synthesized from salicylic acid and acetic anhydride. CONTINUED… 1) Substitution on carboxyl groups may affect the potency and toxicity. 2. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. 8. 4. 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. Nowadays, salicylic acid is administered in the form of aspirin which is less irritating to the stomach than salicylic acid. One of the choicest Chemistry projects for class 12 studnets is the making of Aspirin which a common name for a compound named acetylsalicylic acid, majorly used as a pain killer in our day to day use. 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. Your aspirin product as well as a commercial aspirin tablet will be compared to a standard 0.15% ferricsalicylate solution. 11. Don't let the acetic anhydride contact your skin and don't get the vapors in your eyes. The purity of the product is confirmed by measuring its melting point range. The % concentration for samples A and B can be determined by plugging in the absorbance readings for those samples into the linear equation and solving for x. Measure out 6.0 ml of acetic anhydride and add this to your flask. When the product is completely dry, weigh its weight, determine its melting point (lit mp 135 °C) and calculate the percentage yield of this recrystallized product. A round bottom flask was charged with 1 g (0.0072 mol) of salicylic acid, 3 ml (0.03 mol) of acetic anhydride and 4 drops of 85% phosphoric acid as catalyst. A polymeric material, which is a polyester, is formed in this reaction. Antipyretic (fever reducer)! Do not add the water until crystal formation is complete. Test this crude product for the presence of unreacted salicylic acid using the ferric chloride test. Add 10 drops of aqueous 1% ferric chloride solution to a test tube containing a few crystals of the compound to be tested dissolved in 5 mL water and note the color. This is your percent yield. The synthesis of aspirin may be achieved in one simple step, O-acetylation of salicylic acid (Figure 1), which is incorporated into many undergraduate synthetic chemistry laboratory courses. Record it in your notebook and turn in your product to the Stockroom. Record the weight of the crude solid which probably contains water. Highlight the data and select insert, and scatter (w/ only markers). Aspirin Aspirin is synthesized by the acetylation of salicylic acid using acetic anhydride or acetyl chloride. An excess of these can be disposed of in the sink or if packaged, in the trash. Analgesic (painkiller)! Analgesics are compounds used to reduce pain, antipyretics are compounds used to reduce fever. Be sure to record the filter paper weight in your notebook. The experiment conducted in this report will synthesize, purify and determine the percentage yield of aspirin. Add 50 mL of water and cool the mixture in an ice bath. Do this test with 1.phenol, 2. salicylic acid, and 3. your crude product. Have questions or comments? Filter the solution through a Buchner funnel to remove any insoluble impurities or polymers that may have been formed. Louis; Chemistry). If you have difficulty, look at the banana oil experiment. Allow the flask to cool to room temperature. Calculate the % recovery of recrystallized material from crude material. In this experiment, phosphoric acid will be used as the catalyst. 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 refers to a process of salicylic acid reacting with glacial acetic acid. IUPAC NAME: 2-acetoxybenzoic acid This laboratory project involves the synthesis, characterization, and study of some reactions of acetylsalicylic acid, and the comparison of acetylsalicylic acid with the major components of various commercial brands of aspirin tablets. In this experiment, the researchers combined the salicylic acid, glacial acetic acid and phosphoric acid … Aspirin: some background! Synthesis of Aspirin By: Jon Torre Purpose: To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid (1) to form acetylsalicylic acid (2). Filter the solid aspirin through a piece of pre-weighed filter paper using a Buchner funnel and the aspirator. Aim The aim of this project was to synthesise aspirin using two methods of heating and to compare the percentage yield and melting points of the product synthesised by the two methods. An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. 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. Clearly state if the samples are below the maximum allowable limit for percent salicylic acid (0.15 %). When the product is completely dry, weigh the product, determine its melting point (lit mp 135-136 °C) and calculate the percentage yield. Also, your melting point range may be greater than 2 degrees. One of the oldest drugs! The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer. H 2 SO 4 (use a dropper, H2SO4 is highly corrosive) and swirl the flask gently until the salicylic acid dissolves. The name aspirin was invented by the chemist, Felix Hofmann, who originally synthesized acetylsalicylic acid for … It is the two-step synthesis of aspirin starting from oil of wintergreen. If acetylsalicylic acid does not begin to crystallize out, scratch the walls of the flask with a glass rod. Collect the product by vacuum filtration and rinse out of the flask with a few milliliters of cold petroleum ether. Citric acid and pineapple juice were used as possible green catalysts but only citric acid worked when used in a high concentration. Synthesis of Aspirin … If crystals do not appear, you can scratch the walls of the flask with a stirring rod to induce crystallization. Acetyl-salicylic acid is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system. Download CBSE XII Chemistry Project : PREPARATION OF ASPIRIN AND ACETAMINOPHEN. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. This video shows how to synthesize aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. Polyesters are often made from dicarboxylic acids and diols. Academia.edu is a platform for academics to share research papers. Wash the beaker and the funnel with 5 to 10 mL of water. When the aspirin was prepared, it was isolated and filtered. Click here to let us know! German chemist Felix Hoffman was the first to experiment in the synthesizing of aspirin and was credited with the success of the revolutionary drug. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. • For a subset of the people, aspirin may help prevent heart attacks and strokes. 1. http://www.teachersfirst.com/lessons/forensics/ink-lab.html, 2. www.reachoutmichigan.org/funexperiments/quick/csustan/mrsketch.htm, Invisible Ink : Modeling A Molecular Switch. It was equipped with a reflux condenser, heated to 100 F and stirred vigorously. until dry. Compare the melting point of you aspirin product to the theoretical melting point (138-140 C). Formation of an iron-phenol complex with Fe(lll) gives a definite color ranging from red to violet, depending upon the particular phenol present. 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. If you spill some, wipe it up with a wet paper towel and throw the towel in the trash. The aspirin isolated in this step is the “crude product”. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. The product will appear as a solid mass when crystallization is completed. 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. Cool the mixture slightly in an ice bath until crystallization is completed. Legal. To determine the amount of aspirin in the whole of the given solution. After heating, cautiously add 20 drops of distilled water. Description:This project is about synthesizing green aspirin by replacing sulfuric acid with a natural acid in the synthesis of aspirin. Aspirin is also known as acetylsalicylic acid. Right click a data point and select add trend line. ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). Excess chemicals must be disposed of in the plastic tub of water. Synthesis of Aspirin. Write a structure for the ester formed from acetic acid and ethanol. The purity of the product formed will then be determined by a series of tests. SYNTHESIS OF ASPIRIN (acetylsalicylic acid) Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. The maximum allowable amount of free salicylic acid in an aspirin sample is 0.15% salicylic acid. James Chickos, David Garin, and Valerian D'Souza. Over history, many compounds obtained from nature have been used to cure ills or to produce an effect in humans. You can use some of the filtrate to rinse the Erlenmeyer flask if necessary. A spectrometer (Spectronic 20), salicylic acid, iron (III) nitrate, iron (III) chloride, phosphoric acid, sulfuric acid, acetic anhydride, anhydrous sodium acetate, methyline chloride, hydrochloric acid, and samples of old, expired aspirin in order to synthesize aspirin in four … The percent yield of the crude product will be determined for this reaction. 10. 3. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. Abstract and Figures This aim of this experiment focuses on the synthesis of pure aspirin (acetylsalicylic acid) from ethanoic anhydride and salicylic acid … Normally, you measure reactants to at least two significant figures. Now set the y-intercept to 0 and check the display equation box. The product then is purified by repeated process called crystallization. Only the salicylate ion complexes to iron(III). It is the acetyl derivative of salicylic acid and is an example of a salicylate drug. The salicylic acid and aspirin may cause irritation to your skin or eyes, but are basically not hazardous. Synthesis of Aspirin 1618 Words | 7 Pages. University of Missouri–St. Be sure to wear gloves and safety goggles when using these chemicals. Place the filter paper with the product in a watch glass and put it in the oven at 100 oC for about 30 min. Dissolve the final product in a minimum amount (no more than 2-3 mL) of. One of the most consumed drugs (Production in the US is 10 million Kg/year) Aspirin: Biological activity! See Fig 1. Determination Of Caffeine In Tea Samples. From the titration of your sample, the moles of acetylsalicylic acid present can be determined assuming that there is not a large percentage of an acid impurity present in your crude sample. 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 … If you spill a lot of either of these, notify your instructor. Allow the air to be drawn through the solid and filter paper for 15 minutes. 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. In this case, one molecule (salicylic acid) provides both the "alcohol" and the carboxylic acid. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. Aspirin became commercially available in 1899 and today it is estimated that over a trillion aspirin tablets have been consumed by those in need of its curative effects. This reaction is the reverse of the synthesis reaction. 6. 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. Synthesis of Aspirin Synthesis Purification Characterization. Report the theoretical yield and the percent yield of the aspirin product. In the presence of moisture, aspirin may decompose (hydrolysis) into salicylic acid and acetic acid. Plot a Beer’s Law graph of the standard 0.15% salicylic acid solution (C) on excel with Absorbance (yaxis) vs % salicylic acid (x-axis). First, gather the chemicals and equipment used to synthesize the aspirin. The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap water. Vacuum filter the product using a Buchner funnel. The spectroscopic analysis of aspirin will involve the complexing of iron(III) to the deprotonated form of salicylic acid (salicylate ion) to give a purple solution. 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. The acetic anhydride and phosphoric acid can cause bad burns. The aspirin isolated in this step is the “crude product”. 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. Is the crude product above of below this mark?Explain why this is the case. To make a Beer’s Law plot, enter % Salicylic Acid into one column on the excel spread sheet (0 and 0.15) and absorbance into the next column (0 and the absorbance 5 reading). To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. The purity of the product will also be analyzed. Weigh out 3.0 g of salicylic acid and place in a 250 ml Erlenmeyer flask. Salicylic acid, whose name comes from Salix, the willow family of plants, was derived from willow bark extracts. Activity 1: Synthesis of Aspirin. In folk medicine, willow bark teas were used as headache remedies and other tonics. One popular drug that does both is aspirin. 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