Synthesis of aspirin california state university, northridge figure 1 contains a general diagram of both of these groups. One of the most widely used analgesics painrelieving drugs in the market today is acetylsalicylic acid, popularly known as aspirin. It will react with salicylic acid which is used to synthesize aspirin. Overtime, aspirins main ingredient acetylsalicylic acid will decompose into salicylic and acetic acid which do test positive for phenol groups. Ppt acetylsalicylic acid powerpoint presentation free. 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. Synthesis of aspirin acetylsalicylic acid organic chemistry ii may, 2003 jamie yeadon shannon land leah monroe acetylsalicylic acid carboxylic acid aspirin. Our new crystalgraphics chart and diagram slides for powerpoint is a collection of over impressively designed datadriven chart and editable diagram s guaranteed to impress any audience.
Salicylic acid, whose name comes from salix, the willow family of. Ppt synthesis of aspirin acetylsalicylic acid powerpoint. Aspirin acetylsalicylic acid is a painrelieving compound familiar to virtually. The chemical reaction involved in the synthesis of aspirin is shows below. Equipment and reagents first period salicylic acid buret clamp burner. 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. Jan 08, 2012 any other reaction ingredients that are soluble this includes acetic acid, phosphoric acid, and water will pass through the filter paper. Aspirin synthesis introduction aspirin acetylsalicylic acid is a. Synthesis of acetyl salicylic acid aspirin example. Salicylic acid reacts with acetic anhydrite to form asa. Sa followed by acetylation to acetylsalicylic acid aspirin, asa.
A german chemist named felix hoffman was working for the bayer chemical company. Gorodetsky, in encyclopedia of toxicology third edition, 2014. Phenolate ion reaction with co2 under pressure to form ohydroxy benzoic acid salicylic acid. The reaction of carboxylic acid and alcohol with the presence of a catalyst such as. There are many different reactions that can be conducted in order to synthesize aspirin. Pdf preparing a pure aspirin acetylsalicylic acid researchgate. Us6278014b1 synthetic procedure for the manufacture of. The synthesis of acetylsalicylic acid was accomplished through the esterification of salicylic acid with acetic anhydride under acidic conditions. Organic chemistry ii january 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis. The demonstration that aspirin inhibited prostacyclin synthesis paved the way for the future development of nonsteroidal anti. A purple colour indicate the unreacted salicylic acid, so a purple colour should not exhibit any color change. An ester group is an important functional group that can be synthesized via a number of different way 1. The sample was analyzed for impurities by fouriertransform infrared spectroscopy ftir and observing the melting point.
Pdf,epub,kindle download acetylsalicylic acid eboook for. The maximum allowable amount of free salicylic acid in an aspirin sample is 0. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever. The glycosylated acetylsalicylic acid was prepared with bromo. Pdf the synthesis of salicylic acid from wintergreen oil. Acetylsalicylic acid or aspirin is a medicine that has antipyretic and anticoagulant properties and acts by inhibiting activity of the enzyme cyclooxygenase which is responsible for the production of prostaglandins, substances responsible for inflammation and pain. Test a small amount of the product for the presence of unreacted salicylic acid using.
In the presence of moisture, aspirin may decompose hydrolysis into salicylic acid and acetic acid. Preparation of acetylsalicylic acid aspirin lab report squarespace. Jun 10, 2016 this second, completely revised edition contains the latest results of clinical and pharmacological research on acetylsalicylic acid, addressing the multiple pharmacological properties of this famous drug with a balanced view on their translation into clinical practice, including prevention from cardiovascular diseases and colorectal cancer. The present invention relates to a new process for the obtaining of dimethylaminoethyl acetylsalicylate and its salts. It is characterized by the fact that the synthesis of the acid chloride is effected in an aliphatic hydrocarbon in the presence of pyridine as catalyst. Methyl salicylate is found in wintergreen oil and is therefore commonly used in breath mints. The reaction was conducted using concentrated phosphoric acid as a catalyst. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Gorodetsky, in encyclopedia of toxicology third edition, 2014 chronic toxicity animal. Thus, salicylic acid is limiting and a maximum of 0. Preparation and activity of glycosylated acetylsalicylic acid.
October 27,2008 abstract the studys main objective was to find the purity aspirin throughout six different experiments. Acetylsalicylic acid aspirin health risk, uses, structure, formula. Dry an erlenmeyer flask and add 3 grams of salicylic acid to it. Acetylsalicylic acid flow diagram free pdf file sharing. After this the acetylation of the hydroxy group on ohydroxybenzoic acid will produce acetylsalicylic acid also known as aspirin. This book consists of eight freestanding activities that can be used singly or as a coherent package in. One of the compounds used in the synthesis of aspirin is salicylic acid, which is itself a pain reliever that was known to many ancient cultures, including the native americans who extracted it from willow tree bark. Pdf this aim of this experiment focuses on the synthesis of pure aspirin acetylsalicylic acid from ethanoic. Ppt acetylsalicylic acid powerpoint presentation free to. Daily doses of acetylsalicylic acid in cats produced toxic hepatitis, vomiting, weight loss, and poor appetite in the lowdose group 3363 mg kg. Synthesis of aspirin in the first part of the experiment, aspirin was synthesized. Chart and diagram slides for powerpoint beautifully designed chart and diagram s for powerpoint with visually stunning graphics and animation effects.
One of its resulting components, salicylic acid, is a strong analgesic. Introduction the goal of this experiment is to perform a fischer esterification reaction with salicylic acid and acetic anhydride to synthesize acetylsalicylic acid. In standardization of a pipette, the determine to calculate values that are not measurable with the equipment provided. O acetylsalicylic acid 2acetoxybenzoic acid aspirin formula. Acetylsalicylic acid binds to and acetylates serine residues in cyclooxygenases, resulting in decreased synthesis of prostaglandin, platelet aggregation, and inflammation. It can therefore undergo two different types of esterification reactions, creating an ester either with the hydroxyl or with the acid. Dipartimento di scienze del farmaco, universita degli studi di catania, viale andrea doria 6, 95125 catania, italy. Equipment and reagents first period salicylic acid. 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. Salicylic acid contains a phenol group, but acetylsalicylic acid does not.
Acetylsalicylic acid was then extracted through crystallization. Air dry the crystals and transfer them to a watch glass to dry. 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. Any other reaction ingredients that are soluble this includes acetic acid, phosphoric acid, and water will pass through the filter paper. Pdf biological activities and industrial production of. Aspirin acetylsalicylic acid is a painrelieving compound familiar to virtually all students. Transfer the rest of the crude aspirin to a 50ml erlenmeyer flask. In 1853, gerhardt neutralized salicylic acid by buffering it with sodium sodium salicylate and acetyl chloride, creating acetylsalicylic acid. Theyll give your presentations a professional, memorable appearance the kind of sophisticated look that todays audiences expect. In this lab, we synthesized aspirin using both acid catalysis and base catalysis. The solubility of acetylsalicylic acid in 25 c water is 1. Synthesis of acetylsalicylic acid aspirin anna shahrour. The ratio of cytotoxicity between the prodrug and the free drug was 111.
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. This reaction is the reverse of the synthesis reaction. Aspirin synthesis alternate nonmicrowave procedure. Aspirin rsc education the royal society of chemistry. Synthesis of acetyl salicylic acid over wo3zro2 solid. The acetylsalicylic acid will recrystallize, and the. The collected aspirin will be tested for its purity using fecl 3 aq. Calculate the required minimum volume of hot water to dissolve 60 mg of acetylsalicylic acid.
Synthesis of crosslinked lipase aggregates and their use. Salicylic acid, the main metabolite of aspirin, is an integral part of human and animal metabolism. A balanced equation for the synthesis of aspirin from salicylic acid and acetic anhydride is the following. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. The product of this reaction was compared to the same batch of salicylic acid from which the reactant came, contrasted by retention factor as a measurement of. Pdf crystallization and morphological characteristics of.
Your two primary objectives in this experiment will be to synthesize and analyze aspirin. In this light, adding an aqueous ferric chloride solution into a sample of aspirin is a better way to see if there any unreacted salicylic acid which is not react. The synthesis of salicylic acid from wintergreen oil instructor guide. In 1853 charles gerhardt published the first synthesis of acetylsalicylic acid. Salicylic acid is extremely bitter tasting, and frequent use can cause severe stomach irritation. To this, three drops of concentrated sulfuric acid were added while swirling. 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. Acetic anhydride, sulfuric acid acetylsalicylic acid 2. Therefore we are able to calculate the number of moles of salicylic acid using the equation. Hydrolysis of methyl salicylate and aspirin synthesis. The most known method of aspirin synthesis is acetylation of salicylic acid with acetic anhydride in acidic medium, phosphoric or.
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. One of the most famous salicylate drug today is acetylsalicylic acid, a pharmaceutically active compound known as aspirin. Preparation of galactosylated acetylsalicylic acid prodrug 5. Approach and resultsmice were given oral acetylsalicylic acid at varying doses, oral clopidogrel 5 mgkg body weight, or both. Salicylic acid is extremely bitter tasting, and frequent use can cause severe stomach. Daily doses of acetylsalicylic acid in cats produced toxic hepatitis, vomiting, weight loss, and poor appetite in. Effect of aspirin on disability free survival in the healthy elderly pdf.
Effect of different doses of acetylsalicylic acid on the. Acetylsalicylic acid was synthesized through an esterification reaction of salicylic acid with acetic anhydride. Your two primary objectives in this experiment will be to. Introduction in the first part of this lab we hydrolyzed methyl salicylate to salicylic acid. This paper describes the first of our organic synthesis experiments, the synthesis, purification, and qualitative spectroscopic characterization of aspirin. This agent exhibits analgesic, antipyretic, and anticoagulant properties. Synthesis of aspirin experiment chemistry libretexts. The name aspirin was invented by the chemist, felix hofmann, who originally synthesized acetylsalicylic acid for bayer. Design, synthesis and antiinflammatory activity of novel. Salicylic acid cooh o c o ch3 acetylsalicylic acid aspirin fig. Researchers hypothesize that due to the blocking of the cox pathway, the arachidonic acids are shuttled into the lipoxygenase pathway. Pdf synthesis of acetylsalicylic acid in choline chloride. Synthesis of acetylsalicylic acid in choline chloride based. Iron iii ion reacts with phenols to form a purple complex.
Sequence using boronic acids and nitrosoarenes under transitionmetal free conditions. Introductionaspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a painkiller. Expired lifetime application number us426573a inventor kamlet jonas. In a smallscale laboratory, paracetamol is prepared by a threereaction sequence. Esters are produced through reactions involving acid anhydrides and alcohols muldoon, 1957. Add 25 ml of water to a clean 100ml beaker labeled 3 n hcl using the bottle top dispenser. A filter crucible and mortar and pestle were obtained from the instructor. One way being the fischer esterification, which is a reaction between an alcohol and a carboxylic acid within the presence of a catalyst, synthesizing an ester weldegirma, 2014. Jan 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis chm 2211c.
Aspirin was first isolated by felix hoffmann, a chemist with the german company bayer in 1897. 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. This analgesic can also be extracted from willow bark which. Synthesis of paracetamol from phenol acetaminophen 9. Download free acetylsalicylic acid ebook for kindle tablet ipad android download link download acetylsalicylic acid bookebook pdf epub kindle online for free 20161103. Acetylsalicylic acid an overview sciencedirect topics. Synthesis of acetylsalicylic acid aspirin using acid. Oct 15, 2011 the effects of wo 3 concentration, reaction time, reaction temperature, molar ratio of reactants, as well as dosage of catalysts on synthesis of acetyl salicylic acid were investigated, and the reaction conditions were therefore optimized. His research led to the synthesis of acetylsalicylic acid asa or aspirin. The solubility of acetylsalicylic acid in 37 c water is 1. The method was carried out as described in npu2103 organic synthesis practical manual 2017. Jan 21, 2014 acetylsalicylic acid also known as aspirin is a salicylate drug, often used as an analgesic, antipyretic and antiinflammatory medication. Aspirin is a common analgesic which can be used to treat pain, fever, or inflammation. Doc synthesis of acetylsalicylic acid aspirin anna.
Salicylic acid the first person to do so was a french chemist named charles frederic gerhardt. Worlds best powerpoint templates crystalgraphics offers more powerpoint templates than anyone else in the world, with over 4 million to choose from. Hydrolysis is the process of breaking down a compound into its components. Download fulltext pdf download fulltext pdf read fulltext. The synthesis of aspirin is classified as an esterification reaction. Acetylsalicylic acid is actually an ester derivative of salicylic acid. Acetylsalicylic acid is the chemical name for aspirin, the ubiquitous pain reliever. The aspirin story from willow to wonder drug desborough 2017. 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. Acetylsalicylic acid or aspirin is an acetyl derivative of salicylic acid that is a white, crystalline, weakly acidic substance, with melting point 7c. Dec 11, 2011 synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid.
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