Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst. Acetylsalicylic acid asa is better known to most people by its common name, aspirin. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. In the us, acetylsalicylic acid is a member of the following drug classes. In this lab, we synthesized aspirin using both acid catalysis and base catalysis. The objective is to isolate pure acetylsalicylic acid. Another ester of salicylic acid, the methyl salicylate, commonly known as oil of wintergreen, is absorbed through the skin. Pdf alternative synthesis of paracetamol and aspirin under. The synthesis of cool smelling molecules purpose to expand the use of the concept of nucleophilicity and electrophilicity, to introduce the reactivity of carbonyls, and to demonstrate a class of reactions that is vital to life as we know it by performing an esterification to make a cool molecule.
Meredith ward aspirin synthesis alternate nonmicrowave procedure abstract. The objective of organic synthesis is to design the simplest synthetic routes to a molecule. The balanced chemical reaction of the formation of aspirin. Synthesis of aspirin acetylsalicylic acid from salicylic. In this reaction oacetylation, the oh group of the salicylic acid reacts with an excess of acetic anhydride in the presence of a catalyst sulphuric acid to produce the acetylsalicylic acid. Come browse our large digital warehouse of free sample essays. Bayers pharmacist, heinrich dreser, took care of this, and after tests on animals. The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap. Pure synthesis products, experimental study and the introduction in the industrial reality. Determination of acetylsalicylic acid in aspirin using total fluorescence spectroscopy application note author melissa quinn agilent technologies, inc. It results from the elimination of a molecule of water from two molecules of acetic acid see fig. This experiment teaches the concept of ester formation using a very reactive acid derivative acetic anhydride with an appropriate alcohol.
Acetylsalicylic acid does not have the bad taste and stomach problems of salicylic acid. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever, or inflammation. Aspirin, also known as acetylsalicylic acid is as salicylate drug often used as analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an antiinflammatory medication. Thus, salicylic acid is limiting and a maximum of 0. Company replaced the phenol group with an ester group. 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. Download as ppt, pdf, txt or read online from scribd. Some impurities, such as that of water and carbon dioxide, were detected. Acetylsalicylic acid is not very soluble in cold water 0. Evidencebased studies had proved that asa could reduce the incidence rate of 25% of heart and brain and peripheral thromboembolic disease 3, 4. In this lab, students will analyze aspirin acetylsalicylic acid tablets for the acetylsalicylic acid content, using a volumetric analysis technique called titration. Salicylic acid, whose name comes from salix, the willow family of plants, was derived from willow bark extracts. Jul 27, 2017 acetylsalicylic acid get uptodate information on acetylsalicylic acid side effects, uses, dosage, overdose, pregnancy, alcohol and more. 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.
You will mix iron iii nitrate with salicylic acid in your aspirin sample to complex the salicylic acid, which is a bluishpurple colour. The next step was the pharmaceutical trial of this remedy. Aspirin synthesis tap water was heated on a steam bath in a 250 ml beaker. A meta description is an html tag in the html code of your website, which allows you to customize a section of text that describes the page itself. 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.
Synthesis of acetylsalicylic acid essay free essays, term. Since salicylic acid contains phenolic and carboxylic acid groups, it was irritating to the mouth, throat, and stomach. Some impurities, such as that of water and carbon dioxide, were. Aspirin acetylsalicylic acid is an analgesic, antipyretic, antiinflammatory drug. Acetylsalicylic acid, mainly as its sodium salt is used in veterinary medicine orally in water and feed in pigs, calves and chickens at doses of 5 to 300 mgkg bwday. After considerable work, the derivative acetylsalicylic acid was found to have similar pain.
We will prepare aspirin by reacting salicylic acid 1 with an excess of acetic anhydride 2 to produce aspirin 3 and acetic acid. Check with your doctor immediately if any of the following side effects occur while taking aspirin. The excess acetic anhydride is then decomposed with water to form acetic acid. Not all of the mass of an aspirin tablet is acetylsalicylic acid, as there are starch binders added to hold the tablet together.
Abstract despite of its long history as a drug, aspirin acetylsalicylic acid, asa still fascinates investigators across the fields of chemistry. Salicigen, an extract of willow and poplar bark, has been used as a pain reliever. The phenol group on the salicylic acid forms an ester with the carboxyl group on the acetic acid. Acetylsalicylic acid is an acetic acid ester derivative of salicylic acid. Sigma a5376 page1 of 8 sigmaaldrich safety data sheet version 4. Pharmacology acetylsalicylic acid schror wiley online. The generic form of this drug is commonly called acetylsalicylic acid asa.
The metabolism of acetylsalicylic acid aspirin is summarized in figure 1. Salicylic acid has the formula c6h4ohcooh, where the oh group is ortho to the carboxyl group. To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid 1 to form acetylsalicylic acid 2. Over the years the company has allowed the term aspirin to fall into the. Determination of acetylsalicylic acid in aspirin using total. For this reason, it is industrially synthesized on a massive scale, producing up. An ester is a compound that is formed when an acid containing the cooh group reacts with an alcohol a compound containing an oh group. 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. Pure synthesis products, experimental study and the. Jun 10, 2016 the pharmacology of aspirin is unique in both, pharmacokinetic and pharmacodynamics aspects. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co gr. Acetylsalicylic acid asa had significant antiplatelet aggregation function and it had been used for the prevention and treatment of ami and thrombosis diseases from 1970s. Postu department of chemistry, american university, washington, d.
O acetylsalicylic acid 2acetoxybenzoic acid aspirin formula. Aspirin hc9h7o4 or c9h8o4 cid 2244 structure, chemical names. Aspirin is a trade name for acetylsalicylic acid, a common analgesic. Synthesis of aspirin synthesis purification characterization. In the presence of moisture, aspirin may decompose hydrolysis into salicylic acid and acetic acid.
Introduction fluorescence is the emission of light by a molecule in an excited electronic state. Chemistry 51 experiment 11 synthesis and analysis of aspirin. You will analyse several samples to determine the amount of salicylic acid impurity in your synthesized aspirin. The search for a milder form of this pain reliever led to the successful synthesis of acetylsalicylic acid by the german chemist felix hoffmann in 1893.
Note in equation 293 that the byproduct of the reaction is now acetic acid rather than water. Preparation of acetylsalicylic acid aspirin background one of the most widely used nonprescription drugs is aspirin. Hypersensitivity to acetylsalicylic acid or to any of the excipients listed. Acetylsalicylic acid in aspirin tablets lab the purpose of this lab was for us to find the amount of acetylsalicylic acid in aspirin tablets and compare this experimental value with the true value. In this reaction, a hydroxyl group is converted to an ester, with acetic acid as a byproduct. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever.
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. This agent exhibits analgesic, antipyretic, and anticoagulant properties. Acetylsalicylic acid asa is effective in preventing strokes, heart attacks and vascularrelated events associated with cardiovascular disease cvd. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. A balanced equation for the synthesis of aspirin from salicylic acid and acetic anhydride is the following. 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. Overthecounter aspirin acetylsalicylic acid in cdcl3 o 4. Co administration of oral anticoagulants with acetyl salicylic acid used. Jan 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis chm 2211c. This study was conducted on the industrial production of acetylsalicylic acid as neither the reactants nor products are toxic or.
In some countries, this medicine may only be approved for veterinary use. Effect of aspirin on disability free survival in the healthy elderly pdf. Aspirin or acetylsalicylic acid acetosal is a drug in the family of salicylates, often used as an analgesic against minor pains and aches, antipyretic against fever, and antiinflammatory. 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. Taking into account the prac assessment report on the psurs for acetylsalicylic acid the scientific conclusions are as follows. Synthesis of aspirin experiment chemistry libretexts. It plays a role in how your page is seen by search engine crawlers, and how it appears in serps. Along with its needed effects, aspirin the active ingredient contained in acetylsalicylic acid may cause some unwanted effects. Hofmann was able to produce acetylsalicylic acid by reacting salicylic acid with acetic anhydride in an acidic solution. Synthesis of aspirin lab report 2989 words bartleby synthesis of aspirin. Synthesis of aspirin salicylic acid derivatives, or salicin, are found in the bark of the willow tree.
Synthesis of acetyl salicylic acid aspirin essay example. The earliest known uses of the drug can be traced back to the greek physician hippocrates in the fifth century b. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. E29 preparation of aspirin acetylsalicylic acid and thinlayer chromatography of analgesic drugs the task to prepare a pharmaceutical compound and test its purity. About the thermal behavior of acetylsalicylic acid and aspirin. Although various chem ists were able to produce salicin and salicylic acid in the. Get the knowledge you need in order to pass your classes and more. Bayer coined the name aspirin for their new product to reflect its acetyl nature and its natural occurrence in the spiraea plant.
Doc synthesis of acetylsalicylic acid aspirin anna. E29 preparation of aspirin acetylsalicylic acid and thin. Biological basis and clinical implications of acetylsalicylic acid. 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. The phenomenon of fluorescence in most cases represents the.
The ferric chloride test and melting point were used to test the purity of the results. A hypothesized recovery rater of above 50% was expected. Acetylsalicylic acid has both antiinflammatory and antipyretic effects. Experiment 22 synthesis of aspirin and oil of wintergreen. Acetylsalicylic acid side effects, uses, dosage, overdose. The name aspirin was invented by the chemist, felix hofmann, who originally synthesized acetylsalicylic acid for bayer. Once acetylsalicylic acid is absorbed from the intestine, it is converted back to salicylic acid. He used powder extracted from the bark of willows to treat pain and reduce fever.
Preparation and characterization of acetylsalicylic acid. The two step synthesis encompasses aqueous base hydrolysis of wintergreen oil methyl salicylate, ms to salicylic acid sa followed by acetylation to acetylsalicylic acid aspirin, asa. First, the aspirin was synthesized using acetic anhydride, salicylic acid, and an acid catalyst. Synthesizing aspirin and oil of wintergreen purpose in this experiment, you will synthesize acetylsalicylic acid, commonly known as aspirin, and methyl salicylate, oil of wintergreen, from salicylic acid. Your two primary objectives in this experiment will be to. What we first did was make the 100 ml aspirin solution up by using a mortar and pestle to grind up the tablet and then we dissolved the aspirin. This is not surprising when one considers the medicinal applications for aspirin. Read this essay on synthesis of acetylsalicylic acid.
Acetylsalicylic acid is expected to have a lower rf value than salicylic acid. The skills by the end of the experiment you should be able to. Synthesis of acetylsalicylic acid aspirin acetic anhydride and salicylic acid react to produce acetylsalicylic acid and acetic acid. Acetylsalicylic acid an overview sciencedirect topics. 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.
Aspirin acetylsalicylic acid is one of the oldest and most versatile drugs known to medicine. Toxicologic mechanism the acute toxicity mostly is due to a high level of salicylic acid, which uncouples mitochondrial oxidative phosphorylation and also inhibits krebs cycle dehydrogenases 5. After the reaction takes place, water is added to destroy the excess. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid. Also known as aspirin, acetylsalicylic acid asa is a commonly used drug. Synthesis of acetylsalicylic acid aspirin from salicylic acid and acetic anhydride soriano, sosa, sualibios and tan department of chemistry, college of science, university of santo tomas, manila abstract this experiment was done in order to synthesize aspirin from the fischer esterification reaction of salicylic acid and acetic anhydride. You will be able to see how two very different organic compounds can be made from the same common starting material. Salicylic acid is extremely bitter tasting, and frequent use can cause severe stomach irritation.
The strong electrophilic nature of the lewis acid acetic anhydride is increased when protonated by phosphoric acid, enabling formation of a tetrahedral intermediate through attack of the nucleophilic aqueous salicylic acid, the hydroxyl group of which is. Synthesis of aspirin lab report and analysis odinity. Aspirin is only found in individuals who have consumed this drug. Effect of aspirin on disabilityfree survival in the healthy elderly pdf. Aspirin is an orally administered nonsteroidal antiinflammatory agent. This chapter describes the pharmacokinetics of aspirin and salicylate, focusing on the bioavailability of the active drugs, their plasma and tissue distribution, metabolism, and clearance from blood and other body fluids.
In the synthesis of aspirin, you will treat salicylic acid. The preparation consists of an esterification reaction catalyzed by acid h 2 so 4 or h 3 po 4, where salicylic acid treated with acetic anhydride gives acetylsalicylic acid aspirin. View the article pdf and any associated supplements and figures for a period of 48 hours. The ph levels could further confirm the substances since the salicylic acid is more acidic than acetylsalicylic acid. How many moles of acetic anhydride are there in 3 ml of acetic anhydride. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever. Aspirin is effective in reducing fever, inflammation, and swelling and thus has been used for treatment of rheumatoid arthritis, rheumatic fever, and mild. Aspirin given shortly after a heart attack decreases the risk of death. In folk medicine, willow bark teas were used as headache remedies and other tonics.
John lucci chm 255 112616 organic chemistry i lab ta. For this reason, it is industrially synthesized on a massive scale, producing up to 1800 kg 10,000 moles per batch. Synthesis of acetylsalicylic acid topics, sample papers. Acetylsalicylic acid binds to and acetylates serine residues in cyclooxygenases, resulting in decreased synthesis of prostaglandin, platelet aggregation, and inflammation. By the melting point, ftir, and ftnmr analysis, it was determined that the aspirin was relatively pure. However, this reaction is slow and has a relatively low yield. Your synthesis converted most, but not all, of the salicylic acid into acetylsalicylic acid. Although not all of these side effects may occur, if they do occur they may need medical attention.
Synthesis of acetylsalicylic acid aspirin using acid. The first known use of an aspirinlike preparation can be traced to ancient greece and rome. A hot water ethanol mixture about 20 ml hot solvent of waterethanol per gram crude aspirin is used to further purify aspirin by removing acetic acid3. 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.
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. Preparation, purification and analysis of aspirin acetylsalicylic acid synthesis. This aim of this experiment focuses on the synthesis of pure aspirin acetylsalicylic acid from ethanoic anhydride and salicylic acid while using concentrated sulfuric acid as a catalyst for the. Organic chemistry ii january 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis. Therefore we are able to calculate the number of moles of salicylic acid using the equation. Jan 21, 2016 in this video the synthesis of acetylsalicylic acid is shown. H 2 so 4 use a dropper, h 2 so 4 is highly corrosive and swirl the flask gently until the salicylic acid dissolves. The merck index, which is an encyclopedia of chemicals, drugs and biologicals, lists the following information under aspirin.
Safety data sheet northwest missouri state university. Your aspirin product as well as a commercial aspirin tablet will be compared to a standard 0. 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. It is used quite often as an introduction to preparative organic chemistry. It enters the bloodstream where it interferes with the synthesis of prostaglandins and irreversibly binds to an enzyme called cyclooxygenase 2. It is also known as 2hydroxybenzenecarboxylic acid. 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. The method described before is that followed by most manufacturers to make this chemical. If there is a possibility of contaminating the results of the ph testing and iron chloride testing could be inconclusive.
730 899 793 593 778 483 1004 196 766 1148 1437 394 949 880 1170 1075 1051 1170 1447 765 1362 342 1598 1089 1280 1256 1549 838 1145 1182 172 862 130 464 514 432 1299 278 1010 909 1137 92 70 576