From the time of ancient greeks to the present, acetylsalicylic acid or its parent. Pdf preparing a pure aspirin acetylsalicylic acid researchgate. Aspirin is an ester of salicylic acid which passes through the stomach unchanged before being hydrolysed by the basic medium of the intestine to form the active compound. If you will be calculating actual and theoretical yield, be sure to record how much salicylic acid you actually measured. The paper deals with an alternative route for the synthesis of nacetylpaminophenol paracetamol, par and acetylsalicylic acid aspirin, asa using principles of green chemistry, namely solvent. It is one of the oldest and widely used drugs in medicine. Pdf alternative synthesis of paracetamol and aspirin.
Synthesis of acetylsalicylic acid free essay example. The mechanism for this synthesis provides examples of three major classes of chemical reactions. Aspirin is also used longterm to help prevent further heart attacks, ischaemic strokes. Aspirin hc9h7o4 or c9h8o4 cid 2244 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities.
Acetylsalicylic acid definition of acetylsalicylic acid by. Unlimited viewing of the articlechapter pdf and any associated supplements and figures. The products of the reaction between salicylic acid and acetic anhydride are acetylsalicylic acid and acetic acid3. Salicylic acid, whose name comes from salix, the willow family of plants, was derived from willow bark extracts. This document contains side effect information about aspirin. Results for acetylsalicylic acid in 1% acetic acid chloroform solution standard conc mgl emission 1 0. After synthesis and analysis, it will be determined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both 3. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. Pharmacokinetics and pharmacodynamics of acetylsalicylic. Aspirin is effective in reducing fever, inflammation, and swelling and thus has been used for treatment of rheumatoid arthritis, rheumatic fever, and mild. Acetylsalicylic acid by pharmetics inc acetylsalicylic acid asa belongs to the group of medications called analgesics pain relievers, antipyretics fever reducers, antiinflammatories inflammation reducers, and platelet aggregation inhibitors anticlotting agents.
Williamson, macroscale and microscale organic experiments, 2nd ed. The synthesis of aspirin from oil of wintergreen is an example of one of. Your aspirin product as well as a commercial aspirin tablet will be compared to a standard 0. An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid. Inhibition of cox2dependent prostaglandins occurs at much higher oral asa doses than those used in cardiovascular prophylaxis. It can therefore undergo two different types of esterification reactions, creating an ester either with the hydroxyl or with the acid. The ferric chloride test and melting point were used to test the purity of the results. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever. Acetylsalicylic acid is slightly soluble in water, with a limit of solubility reported as approximately 3 mgml at 25 deg c. Some of the dosage forms listed on this page may not apply to the brand name acetylsalicylic acid. An ester group is an important functional group that can be synthesized via a number of different way 1. Aspirin, also known as acetylsalicylic acid, dates back to 1897, when it was isolated by felix hoffmann, a chemist with a german company bayer. In this experiment, you will measure the melting point of your synthesized.
E29 esterification preparation of aspirin acetylsalicylic. Dec 11, 2011 synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid. Aspirin has been used as a medicine by the ancient greeks and the pharaohs of egypt. View the article pdf and any associated supplements and figures for a period of 48 hours. Aspirin and acetic acid are formed when the hydrogen in the phenolic alcohol group of salicylic acid is replaced by an acetyl h3ccoo group. Oacetylsalicylic acid 2acetoxybenzoic acid aspirin formula. To understand the chemistry, the student must be able to recognize the common molecular framework shared by oil of wintergreen, salicylic acid, and aspirin and to identify the oh and co2 sites where chemical changes occur. Results for acetylsalicylic acid in 1% acetic acidchloroform solution standard conc mgl emission 1 0. Salicylic acid and its esters are used as food preservatives, in skincare products and other cosmetics, and in topical medicines. In folk medicine, willow bark teas were used as headache remedies and other tonics. Aqueous solutions of acetylsalicylic acid are most stable at ph 2. Experiment 11 synthesis and analysis of aspirin csun. It is effective in reducing pain it is an analgesic, reducing inflammation antiinflammatory, reducing fever antipyretic, and thinning blood anticoagulant. E29 esterification preparation of aspirin acetylsalicylic acid and thinlayer chromatography of analesic drugs salicin, a glycoside of salicylic acid present in the leaves and bark of willow trees, has been used for centuries in a variety of herbal remedies.
Synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid. Synthesis and purification of acetylsalicylic acid asa or. The chemical name for aspirin is acetylsalicylic acid. The clinical and research facilities of the central islip state hospital, central islip, n. This product includes sodium hydroxide, hydrochloric acid, methyl salicylate, disposable and graduated pipettes, a teachers manual, and a student study guide with copymasters. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. The first step in this esterification is to create a suspension of salicylic acid a solid at room temperature in an excess of acetic anhydride a liquid at room temperature. Jan 21, 2016 in this video the synthesis of acetylsalicylic acid is shown. Microscale synthesis of acetylsalicylic acid aspirin acetyl salicylic acid mw180. It is also soluble in ethanol at 50 mgml and will dissolve in solutions of alkali hydroxides and carbonates with decomposition. Pdf alternative synthesis of paracetamol and aspirin under.
Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. The name aspirin is derived from acetylated spiraeic acid the old name for salicylic acid. Synthesis of aspirin experiment chemistry libretexts. Acetylsalicylic acid definition of acetylsalicylic acid. Preparation of acetylsalicylic acid aspirin background one of the most widely used nonprescription drugs is aspirin. Acetylsalicylic acid preparations specifically intended for use as antithrombotic agents are classified in this group. Aqueous solutions of acetylsalicylic acid are most stable at ph 2 3, but to assure full.
Aspirin originally was derived by boiling the bark of the white willow tree. Download as ppt, pdf, txt or read online from scribd. O acetylsalicylic acid is the prototypical analgesic used in the treatment of mild to moderate pain. Asa product, salicylic acid, a crushed aspirin tablet, and pure asa from. Acetylsalicylic acid aspirin, a prodrug to salicylic acid, is made by an entirely different process. It is used quite often as an introduction to preparative organic chemistry. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid after intravenous and oral administration to healthy volunteers j nagelschmitz,1 m blunck,1 j kraetzschmar,1 m ludwig,1 g wensing,1 t hohlfeld2 1bayer healthcare ag, clinical pharmacology, wuppertal, germany.
Jul 27, 2017 acetylsalicylic acid get uptodate information on acetylsalicylic acid side effects, uses, dosage, overdose, pregnancy, alcohol and more. In the united states, more than 15,000 pounds are sold each year. Aspirin acetylsalicylic acid is a painrelieving compound familiar to virtually all students. The reaction of carboxylic acid and alcohol with the presence of a catalyst such as. Furthermore, the acetylsalicylic acid will be in a free state and travel further because the ester and acetyl functional groups no longer have hydrogen bonds that bond to the polar silica plate. It is the twostep synthesis of aspirin starting from oil of wintergreen.
Synthesis of salicylic acid from oil of wintergreen. Pdf this aim of this experiment focuses on the synthesis of pure aspirin acetylsalicylic acid from ethanoic anhydride and salicylic acid while. In part i of this experiment, you will prepare aspirin by reaction of salicylic acid with acetic anhydride, using concentrated sulfuric acid as a catalyst. It works by interfering with the production of compounds in the body that cause pain, fever, inflammation, and blood clots. Curiously, salicylic acid is also a metabolite of aspirin. Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst. Low doses of orally administered acetylsalicylic acid asa irreversibly inhibit platelet cyclooxygenase cox1, thereby preventing the enzymatic formation of thromboxane a 2, a potent activator of both platelet aggregation and vasoconstriction. In this video the synthesis of acetylsalicylic acid is shown. Add 6 ml of acetic anhydride and 58 drops of 85% phosphoric acid to the flask. The earliest known uses of the drug can be traced back to the greek physician hippocrates in the fifth century b. In the us, acetylsalicylic acid is a member of the following drug classes. Balaguer 1department of physical sciences, college of science, polytechnic university of the philippines, sta.
Macroscale synthesis of acetylsalicylic acid 1alleyromae o. Instead of using acetic acid, acetic anhydride was used as solvent since the anhydride reacting with water to form acetic acid tends to drive the reaction to the right. Salicylic is a weak acid with an alcohol functional group attached to it. In this lab, we synthesized aspirin using both acid catalysis and base catalysis.
To determine when the reaction is complete, students will use a small amount of the indicator. The merck index, which is an encyclopedia of chemicals, drugs and biologicals, lists the following information under aspirin. Aspirin, also called acetylsalicylic acid, derivative of salicylic acid that is a mild nonnarcotic analgesic pain reliever useful in the relief of headache and muscle and joint aches. For this reason, it is industrially synthesized on a massive scale, producing up to 1800 kg 10,000 moles per batch.
Determination of acetylsalicylic acid in aspirin using total. Synthesis of acetylsalicylic acid aspirin using acid. Determination of acetylsalicylic acid in aspirin using. Aspirin is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an antiinflammatory medication 1. Introduction the aim of the experiment is to synthesize acetylsalic acid aspirin, from salicylic acid and acetic anhydride, and to compare is characteristics to commercially available aspirin. Aspirin is a trade name for acetylsalicylic acid, a common analgesic. In this exercise, the goal was to produce acetylsalicylic acid through the organic synthesis from the reaction of salicylic acid to acetic anhydride, the starting materials. This exception from the basic principle of only one code for each route of administration is made because of the extensive use of acetylsalicylic acid both as. The reaction apparatus consists of a 100 ml twoneck flask with magnetic stir bar, temperature sensor and intensive cooler. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. He used powder extracted from the bark of willows to treat pain and reduce fever. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Aspirin given shortly after a heart attack decreases the risk of death.
For this reason, it is industrially synthesized on a massive scale, producing up. Acetylsalicylic acid asa the synthesis of asa from salicylic acid results in the formation of an ester functional group and, therefore, is called an esterification. Since the stoichiometric molar ratio of salicylic acid to acetic anhydride is 1. Synthesis of acetylsalicylic acid dan jones, josh schmidt abstract acetylsalicylic acid, commonly known as aspirin, is considered to be the most successful pharmaceutical product in the world. Eikelboom jw1, odonnell m, yusuf s, diaz r, flaker g, hart r, hohnloser s, joyner c, lawrence j, pais p, pogue j, synhorst d, connolly sj. Expt 80 synthesis of acetylsalicylic acid aspirin fromk. Acetylsalicylic acid definition is a white crystalline derivative c9h8o4 of salicylic acid used for relief of pain and fever. Synthesis of acetylsalicylic acid aspirin acetic anhydride and salicylic acid react to produce acetylsalicylic acid and acetic acid. This is not surprising when one considers the medicinal applications for aspirin. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever, or inflammation. Jan 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis. E29 preparation of aspirin acetylsalicylic acid and thin. They may then use a quick confirmatory test to examine for the presence of salicylic acid, which can be used to synthesize acetylsalicylic acid. The phenol group on the salicylic acid forms an ester with the.
In some countries, this medicine may only be approved for veterinary use. This experiment was carried out to see how the hydroxyl group on the benzene ring in salicylic acid reacts with acetic anhydride to form an ester, and to make aspirin. O acetylsalicylic acid 2acetoxybenzoic acid aspirin formula. The excess acetic anhydride is then decomposed with water to form acetic acid. Acetylsalicylic acid, or aspirin, which is derived from salicylic acid, is the most widely used mild analgesic. In vivo, it is converted into salicylic acid which acts to reduce. A greener synthesis of acetylsalicylic acid wards science. The average tablet contains about 325 milligrams of the active ingredient acetylsalicylic acid combined with an inert binding material such as starch. A small amount of a strong acid is used as a catalyst which speeds up the reaction. Aspirin is used to relieve pain, reduce inflammation, and lower fever. One electron pair is represented by a single black dot. Thus, salicylic acid is limiting and a maximum of 0. It is considered the prototype aspirin is sometimes used in the prevention of certain diseases, though its role as a preventive agent is controversial because of the risk of adverse effects. Acetylsalicylic acid is an acetic acid ester derivative of salicylic acid.
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