It works by prevents the synthesis of prostaglandins by inhibiting both the cyclooxygenase1 cox1. Acetylsalicylic acid side effects, uses, dosage, overdose. E29 preparation of aspirin acetylsalicylic acid and thinlayer chromatography of analgesic drugs the task to prepare a pharmaceutical compound and test its purity. Pdf alternative synthesis of paracetamol and aspirin under. Salicigen, an extract of willow and poplar bark, has been used as a pain reliever. The chemical name for aspirin is acetylsalicylic acid. Titrate potentiometrically the acetylsalicylic acid with a strong base and. Acetylsalicylic acid combined with pseudoephedrine in common cold. Full reports combine the introduction, methods, results and discussion. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. It enters the bloodstream where it interferes with the synthesis of prostaglandins and irreversibly binds to an enzyme called cyclooxygenase 2. E29 esterification preparation of aspirin acetylsalicylic. Aspirin, also known as acetylsalicylic acid asa, is a medication used to treat pain, fever, or inflammation. Aspirin hc9h7o4 or c9h8o4 cid 2244 structure, chemical names.
This study was conducted on the industrial production of acetylsalicylic acid as neither the reactants nor products are toxic or. Synthetic procedure for the manufacture of aspirin. 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. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. Lab 1 synthesis of acetylsalicylic acid using acid.
Expt 80 synthesis of acetylsalicylic acid aspirin fromk. In this lab, we synthesized aspirin using both acid catalysis and base catalysis. Organic chemistry ii january 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis. The aim of the experiment was to form acetylsalicylic acid aspirin from salicylic acid and acetic anhydride and to compare our products properties. Aspirin is only found in individuals who have consumed this drug.
Specifies the medication aspirin acetylsalicylic acid, aspirin, arthritis foundation safety coated aspirin, bayer aspirin, bayer childrens aspirin, ecotrin, and many others, a drug used for the treatment of arthritis, pain, inflammation, and fever. In this experiment, you will prepare aspirin from salicylic acid and acetic anhydride using sulfuric acid as a. Aspirin is the most widely used overthecounter drug in the world. He used powder extracted from the bark of willows to treat pain and reduce fever.
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. 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. Mar 11, 2015 synthesis of aspirin acetylsalicylic acid txeell s. 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. Jan 21, 2016 in this video the synthesis of acetylsalicylic acid is shown. We will prepare aspirin by reacting salicylic acid 1 with an excess of acetic anhydride 2 to produce aspirin 3 and acetic acid 4. For this reason, it is industrially synthesized on a massive scale, producing up.
Synthesis of acetylsalicylic acid aspirin using acid. Aspirin is used medically to reduce fever and pain. Aspirin is a trade name for acetylsalicylic acid, a common analgesic. The phenol group on the salicylic acid forms an ester with the carboxyl group on the acetic acid. Synthesis of aspirin in the first part of the experiment, aspirin was synthesized. Acetylsalicylic acid does not have the bad taste and stomach problems of salicylic acid. It works by prevents the synthesis of prostaglandins by inhibiting both the cyclooxygenase1 cox1 and cyclooxygenase2 cox2 isoenzymes. E29 preparation of aspirin acetylsalicylic acid and thin. Synthesis of aspirin acetylsalicylic acid using acid and base catalysis chm 2211c. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer.
Acceptable secondary sources are the lab manual and course textbook. Aspirin given shortly after a heart attack decreases the risk of death. Full report guide general chemistry lab reports full reports. Synthesis and transdermal properties of acetylsalicylic acid. The use of aspirin had its origin in the 18 th century, when it was found that an. Synthesis of acetylsalicylic acid essay free essays, term. View lab report post lab 5 synthesis of aspirin from chm 2211l at university of south florida. Pdf the primary aim of this study was to determine the transdermal penetration of acetylsalicylic acid and some of its derivatives, to establish. Experiment 6 experiment 6 acetylsalicylic acidaspirin. Use the diagram and instructions on filtration in the techniques section of the manual to. Pure synthesis products, experimental study and the introduction in the industrial reality. Introduction aspirin is among the most fascinating and versatile drugs known. 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.
The isochorismate ic pathway route 1, green is the primary route for sa production in arabidopsis thaliana. Two ester derivatives of this acid, synthesized as shown, are currently in common medicinal use. Acetylsalicylic acid get uptodate information on acetylsalicylic acid side effects, uses, dosage, overdose, pregnancy, alcohol and more. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co gr.
All structured data from the file and property namespaces is available under the creative commons cc0 license. Jul 27, 2017 acetylsalicylic acid get uptodate information on acetylsalicylic acid side effects, uses, dosage, overdose, pregnancy, alcohol and more. 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. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever. Thus, salicylic acid is limiting and a maximum of 0. The production of aspirin is a n example of an esterification process which is a reversible reaction that produces the ester. Stir the mixture until the salicylic acid dissolves. A filter crucible and mortar and pestle were obtained from the instructor. It can therefore undergo two different types of esterification reactions, creating an ester either with the hydroxyl or with the acid. Material safety data sheet acetylsalicylic acid product observe all federal, state, and local environmental regulations. However, this reaction is slow and has a relatively low yield.
Acetylsalicylic acid is an acetic acid ester derivative of salicylic acid. If you will be calculating actual and theoretical yield, be sure to record how much salicylic acid you actually measured add 6 ml of acetic anhydride and 58 drops of 85% phosphoric acid to the flask. Salicylic acid, whose name comes from salix, the willow family of plants, was derived from willow bark extracts. Synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid. The skills by the end of the experiment you should be able to. 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. Postu department of chemistry, american university, washington, d. Synthesis and transdermal properties of acetylsalicylic acid derivates minja gerber minja gerber thesis m.
The earliest known uses of the drug can be traced back to the greek physician hippocrates in the fifth century b. Aspirin is an effective analgesic pain reliever, antipyretic fever reducer and antiinflammatory agent and is one of the most widely used nonprescription drugs. It is a derivative of salicylic acid which is also an. Aspirin acetylsalicylic acid is an analgesic, antipyretic, antiinflammatory drug. It was eventually discovered that salicylic acid is the portion of these molecules responsible for the therapeutic effect. The products formed are acetylsalicylic acid and ethanoic acid. Synthesis and quant itation of acetylsalicylic acid aspirin. 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.
The present invention provides a method for the synthesis of acetyl salicylic acid comprising mixing acetic anhydride and salicylic acid in approximately or exactly stoichiometric proportions and calcium oxide or zinc oxide, obtaining a yield of a mixture of acetyl salicylic acid and calcium acetate or zinc acetate with 2% maximum of free salicylic acid content. This agent exhibits analgesic, antipyretic, and anticoagulant properties. Synthesis of acetylsalicylic acid topics, sample papers. Once acetylsalicylic acid is absorbed from the intestine, it is converted back to salicylic acid. The average tablet contains about 325 milligrams of the active ingredient acetylsalicylic acid combined with an inert binding material such as starch. Synthesis of aspirin experiment chemistry libretexts.
The phenylalanine ammonialyase pal pathway from transcinnamic acid route 2, tan has been implicated in sa synthesis in a number of species and plays a minor role, either directly or indirectly, in sa. Dec 20, 2011 salicylic acid sa has been shown to regulate various aspects of growth and development. It is used quite often as an introduction to preparative organic chemistry. Synthesis of aspirin synthesis purification characterization. For this reason, it is industrially synthesized on a massive scale, producing up to 1800 kg 10,000 moles per batch. Download as ppt, pdf, txt or read online from scribd.
Preparing esters from an alcohol and a carboxylic acid using an acid as catalyst is one of the most useful reactions in an organic chemists toolbox. Compounds or agents that combine with cyclooxygenase prostaglandinendoperoxide. Acetylsalicylic acid binds to and acetylates serine residues in cyclooxygenases, resulting in decreased synthesis of prostaglandin, platelet aggregation, and inflammation. Get the knowledge you need in order to pass your classes and more. Combine 15 drops of acetic acid, 25 drops of 1pentanol namyl alcohol in a small test tube. Some employ catalysts, particular solvents or even no solvents at all. H 2 so 4 use a dropper, h 2 so 4 is highly corrosive and swirl the flask gently until the salicylic acid dissolves heat the flask gently on the steam bath for at least 10 minutes. Pharmacokinetics and pharmacodynamics of acetylsalicylic. In vivo, it is converted into salicylic acid which acts to reduce. Listing a study does not mean it has been evaluated by the u. In folk medicine, willow bark teas were used as headache remedies and other tonics. Aspirin is an orally administered nonsteroidal antiinflammatory agent. This statement, however, has never been challenged.
For procedure reference, refer to lab manual ch110 lab manual, fall 20 pages 9294. Jan 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis chm 2211c. Matthew szapacs, mary jo bo jan and joseph keiser, 71604 hoffman sought to improve this drug. Preparation, purification and analysis of aspirin acetylsalicylic acid synthesis.
Synthesis and transdermal properties of acetylsalicylic. A small amount of a strong acid is used as a catalyst which speeds up the reaction. Come browse our large digital warehouse of free sample essays. Pdf synthesis and transdermal properties of acetylsalicylic acid.
Nov 05, 2015 as said, many other processes are used in manufacturing acetylsalicylic acid. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid. Synthesis and purification of acetylsalicylic acid asa or. Potential pathways for the biosynthesis of salicylic acid in plants. Write detailed mechanisms showing how pyridine and phosphoric acid catalyze the formation of acetylsalicylic acid. Files are available under licenses specified on their description page. 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. Aspirin is an analgesic, a substance that provides relief for inflammation and. The safety and scientific validity of this study is the responsibility of the study sponsor and investigators. Pdf alternative synthesis of paracetamol and aspirin.
The first known use of an aspirinlike preparation can be traced to ancient greece and rome. It has a few side effects for some people, yet it is safe enough to be sold without a prescription. Aspirin alternatives huntington college of health sciences. Experiments synthesis, purification, and characterization of acetylsalicylic acid aspirin can be prepared by combining acetic acid and salicylic acid sa which. Synthesis of soap involves the reverse of ester synthesis. The purpose of the experiment was to determine the synthesis of aspirin and with melting point and absorbance of aspirin the purity was determined.
Dec 11, 2011 synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid. In 1838, pure salicylic acid was synthesized by an. It is widely used as an analgesic pain reliever and fever depressant. Williamson, macroscale and microscale organic experiments, 2nd ed. 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. What has been demonstrated in this study is that this solvent will not only aid the synthesis phase but also act as a means of separation in the purification phase which is extremely convenient. 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. Acetylsalicylic acid is a wonder drug par excellence. Contact a licensed professional waste disposal service to dispose of this material. Pure synthesis products, experimental study and the. Acetylsalicylic acid asa blocks prostaglandin synthesis. Place the conical vial in an aluminum block on a stirring hotplate, and, while stirring, slowly, and in small portions, add 0. Preparation of aspirin experiment 5 introduction in this experiment you will prepare a sample of aspirin, recrystallize the raw product, and determine the percentage yield of the aspirin based on the limiting reactant.
Acetylsalicylic acid combined with pseudoephedrine in. Read this essay on synthesis of acetylsalicylic acid. Learn vocabulary, terms, and more with flashcards, games, and other study tools. In this video the synthesis of acetylsalicylic acid is shown. 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. Post lab 5 synthesis of aspirin 1 synthesis of acetylsalicylic acidaspirin 2 introduction aspirin is a drug known primarily for its pain relieving. 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.