Premium Essay

Synthesis of Acetylsalicylic Acid

In: Science

Submitted By AlleyIndong
Words 1822
Pages 8
MACROSCALE SYNTHESIS OF ACETYLSALICYLIC ACID
1Alleyromae O. Indong, 2Aldrin M. Pragacha, 3Vince Neil B. Balaguer
1Department of Physical Sciences, College of Science, Polytechnic University of the Philippines, Sta. Mesa, Manila, Philippines
Date Performed: December 3, 6, 2014
Date Submitted: December 17, 2014

Abstract

Acetylsalicylic acid or Aspirin is an analgesic, anti-inflammatory and antipyretic agent. It was synthesized to alter the corrosive nature of Salicylic acid that causes gastric pain in the mouth and esophagus. Aspirin can be synthesized by the reaction of Salicylic acid with acetic anhydride and 85% Phosphoric acid as the catalyst when heated in a water bath at 90°C. The formation of white crystals after scratching the solution and after cooling in an ice bath indicates the presence of the product formed after the reaction. Solubility test with water and toluene, melting point determination by oil bath and thin layer chromatography by different kinds of solvents such as 10%EA in DCM, 30%EA in DCM, 10% hexane in EA and 10% DCM in Acetone are confirmatory tests for the presence of Acetylsalicylic acid. Thin layer chromatography is an analytical technique to determine the identity of the substances and to determine the effectiveness of purification.
Keywords: Acetylsalicylic acid, solubility test, melting point, thin layer chromatography Introduction

Acetylsalicylic acid, commonly called “aspirin” is an analgesic, an antipyretic and an anti-inflammatory agent. Aspirin was synthesized by Charles Gerdhadt but was patented to the Bayer Company by Felix Hoffman. It was synthesized to alter the corrosive nature of salicylic acid that causes gastric pain in the mouth and esophagus attacking the mucous membrane, which was intended to cure not to worsen the pain. It contains not less than 99.5 percent of 2-(acetyloxy)benzoic acid. Aspirin is a

Similar Documents

Premium Essay

Orgo Chm Lab

...Alkouk CHM 203-003 23 October 2014 I. Title Acetylsalicylic Acid (Aspirin) Synthesis II. Introduction The purpose of this experiment is to synthesize aspirin (acetylsalicylic acid) by the esterification method using salicylic acid and acetic anhydride. This experiment was unsuccessful due to error and impurities. Chemical Reaction of Experiment In this reaction, the hydroxyl group (-OH) on the benzene ring of the salicylic acid reacted with acetic anhydride to form an ester, with the help of the catalyst, phosphoric acid. III. Experimental A hot water bath with 100 ml of water at 50 degrees Celsius was prepared using a 250 ml beaker and a hot place. From there, 0.251 grams of salicylic acid were weighed (MW=183.1g/mol) and placed in a dry 5 ml conical vial. Also, 0.480 mL of acetic anhydride (MW=10.9 g/mol) was added with one drop of concentrated phosphoric acid from a Pasteur pipet was added. The phosphoric acid acted as a catalyst to aid in the synthesis. Also, added a magnetic spin vane and attached an air condenser to the vial, stirred the mixture with the spin vane until the salicylic acid and phosphoric acid had dissolved, and heated mixture for 8 to 10 minutes after the solid had dissolved to complete the reaction, which made the acetylsalicylic acid and the acetic acid from the mixture of salicylic acid and acetic anhydride. For the crystallization of the acetylsalicylic acid, the vial was removed from the water bath to cool...

Words: 1172 - Pages: 5

Free Essay

Asdfadsf

...Laboratory Report I. Title: We will use titration to determine the purity of synthesized aspirin. In doing so, we will measure the volume of the aspirin accurately. Then, we will use NaOH to titrate the aspirin solution. The analysis of this titration data will allow use to calculate the percentage of acid in the original solution. We will then compare these values to those expected is the sample was made from pure acetylsalicylic acid. The difference from this will come from impurities. II. Authors: Katie Warren, Annie Haman & Jacob Brotherton III. Abstract: The mass of acetylsalicylic acid was determined using a analytical balance. Sodium hydroxide (NaOH) was added to the “white powder” to titrate to produce a persistent, pale pin endpoint. The percentage purity of aspirin was found to be 74.88%. IV. Pre-lab assignment: OMIT V. Procedure: Refer to the lab handout for procedure VI. Chemical Reactions: Aspirin Synthesis: NaOH (aq) + KHC8H4O4 (aq) NaKC8H4O4 (aq) + H2O (I) Aspirin Titration: HA (aq) + NaOH (aq) H2O (I) + NaA (aq) VII. Experimental/Calculated Data: Table 1: Mass of Aspirin | Trial 1 | Mass Watch Glass + White Powder (g) | 38.2625 | Mass of Empty Watch Glass (g) | 37.72 | Mass of White Powder | .5425 | VIII. Calculations: IX. Results and Discussion: X. Conclusions: We have experimentally determined and achieved the percent purity of the aspirin we had previously made. The volume of the solvent that dissolved...

Words: 288 - Pages: 2

Premium Essay

Willow Bark

...Organic Chemistry Research Assignment (Pg. 77 #53) The Structure of Aspirin and its Relation to Willow Bark Question: Acetylsalicylic acid (ASA), better known as Aspirin, is a common pain reliver. Research the following topics: - Explore the chemical reactions associated with the synthesis of ASA, Determine the type of reaction that occurs, and the class of organic compounds involved. - Research the historical connection between willow bark and ASA. What advantages does ASA have over the compound extracted from willow bark? How were these advantages achieved? Introduction: Aspirin, otherwise known as acetylsalicylic acid is a common over the counter medication which is used to reduce fever and relieve moderate pains. In lower doses it may also...

Words: 1315 - Pages: 6

Premium Essay

Chemistry

...org General Chemistry ACETIC ACID & ACETIC ANHYDRIDE Acetic acid is the chemical compound responsible for the characteristic odor and sour taste of vinegar. Typically, vinegar is about 4 to 8% acetic acid. As the defining ingredient of vinegar, acetic acid has been produced and used by humans since before the dawn of recorded history. In fact, its name comes from the Latin for vinegar, acetum. Vinegar is formed from dilute solutions of alcohol, such as wine, by the action of certain bacteria in the presence of oxygen. These bacteria require oxygen, and the overall chemical change is the reaction of ethanol with oxygen to form acetic acid and water. O CH3CH2OH + O2 CH3COH + H2O The name, vinegar, comes from the French, vin aigre, which means “sour wine.” Nevertheless, vinegar may also be obtained from other fermented beverages such as malt or cider. Because vinegar is acidic, it has a variety of properties useful around the house. Mineral deposits left when hard water evaporates, such as those formed on plumbing fixtures and in tea kettles, dissolve in acids, so vinegar can be used to remove them. Because it is acidic, vinegar also inhibits the growth of bacteria, so vinegar is used as a preservative in foods, such as pickled vegetables, and as a mild disinfectant in cleaning. Of course, its sour taste, which is also a result of its acidity, makes it popular as a flavoring in cooking and in salad dressings. Pure acetic acid was first isolated about 1700 by...

Words: 1040 - Pages: 5

Premium Essay

Pain Management Case Study

...compounds with analgesic, anti-inflammatory and antipyretic properties. For thousands of years, aspirin’s precursor and willow bark’s active ingredient, salicin, have been widely used in folk medicine. From Egyptians to Hippocrates, salicin applications varied between topical and oral routs for its antipyretic and analgesic properties. The big turning point from folk remedy #salicin$ to blockbuster drug #now known as Aspirin$ began in 1763 with early trials of extraction and modifications. It was not before the year 1828 until salicin was successfully extracted from and modified to produce what is known today as aspirin(Wick, 2012). Despite its efficacy, gastrointestinal toxicity #particularly dyspepsia$ associated with the use of acetylsalicylic acid #ASA$ led to the development of phenylbutazone in the early 1950s. It was the first non-salicylate NSAID developed for use in patients with inflammatory conditions. Again, toxic effects on bone marrow raised high concerns and finally led to Phenylbutazone’s withdrawal from markets(Lees and Toutain, 2013). As a substitute for...

Words: 863 - Pages: 4

Free Essay

Recrystallization of Acetanilide

...Department of Medical Technology Faculty of Pharmacy University of Santo Tomas, España, Manila Organic Chemistry Laboratory Recrystallization of Acetanilide Experiment 4 Author: Janina Erika G. Sese Group 8 – 2C Medical Technology (A.Y. 2015-2016) Members: Kathleen Danielle Marie A. Robles, Amiel C. Sabangan, Hanz Jefry A. Saliendra, Andrea Betina M. Vega, Anna Denise Z. Yang ------------------------------------------------- Date Submitted: October 28, 2015 ------------------------------------------------- ABSTRACT Recrystallization is the simplest and most widely used operation for purifying organic solids that differ in their solubility at different temperatures. In this experiment, three test tubes with water, hexane and, ethanol, respectively, were used to dissolve pure acetanilide. These test tubes were placed in a water bath for one to five minutes, then, were cooled through running water for the selection of the best solvent to use in recrystallization. Crude acetanilide was obtained by mixing two milliliters aniline and 20 milliliters distilled water with three milliliters acetic anhydride, which was cooled with running water. It was then filtered and dried for the procurement of crude acetanilide. This was mixed with 20 milliliters of the chosen solvent and heated through water bath until the solid was dissolved. Next, it was immediately filtered while hot. The filtrate was collected and was cooled with running water leading to...

Words: 2243 - Pages: 9

Free Essay

Drug Chart

...gru NURSES RESPOSIBILITY | Instruct patient to take acamprosate exactlyas prescribed, even if a relapse occurs,and to seek help for a relapse.•Warn patient that acamprosate won’treduce symptoms of alcohol withdrawal ifrelapse occurs followed by cessation.• Urge caregivers to monitor patient for evidenceof depression (lack of appetite orinterest in life, fatigue, excessive sleeping,difficulty concentrating) or suicidal tendenciesbecause a small number ofpatients taking acamprosate have attemptedsuicide.• Advise patient to use caution when performinghazardous activities until adverseCNS effects of drug are known. | SIDE EFFECTS | Adverse ReactionsCNS: Abnormal thinking, amnesia, anxiety,asthenia, chills, depression, dizziness,headache, insomnia, paresthesia, somnolence,suicidal ideation, syncope, tremorCV: Chest pain, hypertension, palpitations,peripheral edema, vasodilationEENT: Abnormal vision, dry mouth,pharyngitis, rhinitis, taste perversionGI: Abdominal pain, anorexia, constipation,diarrhea, flatulence, increased appetite,indigestion, nausea, vomitingGU: Acute renal failure, decreased libido,impotenceHEME: Leukopenia, lymphocytosis, thrombocytopeniaMS: Arthralgia, back pain, myalgiaRESP: Bronchitis, cough, dyspneaSKIN: Diaphoresis, pruritus, rash | INDICATION | To maintain abstinence from alcohol foralcohol-dependent patients who areabstinent at the start of treatment CONTRAINDICATIONHypersensitivity to acamprosate or its com- ponents, severe hepatic (Child-Pugh...

Words: 3878 - Pages: 16

Free Essay

Pestel Analysis of Pharmaceutical Industry

...ANNUAL REVIEWS Further Quick links to online content Ann. Rev. PharmacoL ToxicoL Copyright © 1983 1983. 23:87-101 by Annual Reviews Inc. All rights reserved THE TREATMENT OF ACETAMINOPHEN Annu. Rev. Pharmacol. Toxicol. 1983.23:87-101. Downloaded from www.annualreviews.org by Queen Mary & Westfield on 03/14/11. For personal use only. POISONING L. F. Prescott and J. A. J. H Critchley Regional Poisoning Treatment Centre, and University Department of Therapeutics and Clinical Pharmacology, The Royal Infirmary, Edinburgh, EH3 9YW, Scotland INTRODUCTION Acetaminophen (paracetamol, N-acetyl-p-aminophenol, 4-hydroxyacetani­ lide) is a non-prescription antipyretic analgesic that was first introduced into clinical medicine towards the end of the last century (1). It attracted little interest until it was found to be the major metabolite of both acetani­ lide and phenacetin (2, 3) and in recent years it has become an increasingly popular substitute for aspirin. Acetaminophen seemed to be remarkably safe when taken in recommended doses and formal toxicity studies were never carried out. In 1964 Eder (4) first reported liver damage in cats given 25-50 mglKg of acetaminophen daily for 26 weeks, and two years later Boyd & Bereczky described extensive hepatic necrosis in acute toxicity studies in rats (5). At the same time liver damage was first reported in man following acetaminophen overdosage (6, 7). The use of acetaminophen for self-poisoning has since...

Words: 7818 - Pages: 32

Free Essay

Tawa-Tawa

...Euphorbia Hirta or "tawa-tawa" Tawa Tawa or  Gatas Gatas  (Euphorbia Hirt)        The Mindoro Post, within its article entitled "Dengue Fever Cure using Tawa tawa" (released The month of January 2010, utilized July 2010), creates, "many individuals understand and also have attested in order to the truth that these people and many more happen to be healed associated with dengue using a simple grass. This particular grass is known as Gatas Gatas within the land associated with Leyte. However in Butuan  and Cagayan de Oro  these people call this “Tawa Tawa” ·               At the same time, a wesite  upon Filipino therapeutic grass offers the organic category associated with Tawa Tawa grass  as well as explains which, "its blossoms tend to be several, each about 5  to 8 cm across. Sepals as well as petals tend to be obovate-oblong, yellowish-green, as well as protected along with big, reddish-brown smears” The effectiveness of Tawa Tawa Plant    ·              One of the studies proving Tawa Tawa's efficacy is an investigatory project entitled "The Effectivity of Euphorbia hirta L. (Tawa-tawa), Prepared in Teabag Form, on Increasing Platelet Levels in Mus musculus (White Mice)." The said science project won the Student Research Presentation sponsored by the College of Agriculture atXavier University - Ateneo de Cagayan in thePhilippines. ·            The said project, as the title suggests, probes on increasing blood platelet levels using Tawa Tawa plant. For the...

Words: 8092 - Pages: 33

Free Essay

Fundamental Nursing

...Chapter 1 Nursing Images throughout History 1) The angle of mercy 2) The handmaiden 3) The battle-ax 4) The naughty nurse 5) The military image A. Nurses on the battlefield * Hospitalers – specialized soldiers who at the end of battle returned to the outposts to care for the sick and injured * Army nursing service – organize nurses and hospitals and coordinate supplies for the soldiers during the Civil War * Clara Barton a. Provided care in tents set up close to the fighting b. Did not discriminate c. Establishment of the American Red Cross * Harriet Tubman – helped slaves escape to freedom on the underground railroad * Walt Whitman – a poet * Louisa May Alcott – an author * Dorothea Dix – union’s superintendent of female nurses during the Civil War B. Nurses fighting diseases * Florence Nightingale d. Epidemiology – the study of the distribution and origins of disease e. Air, light, nutrition, and adequate ventilation and space assist the patient to recuperate * Lillian Wald & Mary Brewster f. Founded the Henry Street Settlement in NY to improve the health and social conditions of poor immigrants g. Improve health and prevent illness by promoting safe drinking water, adequate sewage facilities, and proper sanitation Florence Nightingale (1820-1910) ...

Words: 12825 - Pages: 52

Free Essay

The Physiologic Effects of the Crude Concoction from Euphorbia Hirta (Tawa-Tawa) Using Staphylococcus Aureus for Anti-Bacterial Tests and Animal Inoculation Assay for Toxicity 1

...Chapter 1 INTRODUCTION Background Euphorbia hirta, belongs to the family of Euphorbiaceae which is a large family of dicotyledons, with about 300 genera and over 5,000 species. Here in the Philippines, the Euphorbia hirta, is commonly referred to as Tawa-tawa or Gatas-gatas in some provinces. It is also known as Asthma weed or Snake weed in the United States. The plants of 3 different species share Phoretic variations, these plants are: (1) Mutha (Cyperus rotundus), (2) Gatas-gatas (Euphorbia hirta) and (3) Botoncillo (Gomphena globosa). Tawa-tawa is usually very abundant in tropical regions such as the Philippines. A simple weed scattered in sunny lawns, waste places and open grasslands. It is pantropic in distribution. The plant is an annual, hairy herb, usually branched from the base, spreading up to 40 cm long. The stem is slender and often reddish and purplish in color, covered with yellowish bristly hairs especially in younger parts. The leaves are oppositely arranged, elliptical-oblong to oblong-lanceolate, 1 to 2.5 cm long, toothed at the edge, and blotched with purple in the middle. In the axils appear numerous involucres, purplish or greenish, dense, axillary, short stalk clusters or crowded cymes, about 1 mm long. The capsules are broadly ovoid, hairy, three-angled, about 1.5 cm. The small green flowers constitute the inflourescence characteristics of the euphorbias. The stem and the leaves produce white or milky juice when cut (Lind and Tallantire...

Words: 8195 - Pages: 33

Free Essay

Documents

...Clinical guidelines Diagnosis and treatment manual for curative programmes in hospitals and dispensaries guidance for prescribing 2010 EDITION © Médecins Sans Frontières – January 2010 All rights reserved for all countries. No reproduction, translation and adaptation may be done without the prior permission of the Copyright owner. ISBN 2-906498-81-5 Clinical guidelines Diagnosis and treatment manual Editorial Committee: I. Broek (MD), N. Harris (MD), M. Henkens (MD), H. Mekaoui (MD), P.P. Palma (MD), E. Szumilin (MD) and V. Grouzard (N, general editor) Contributors: P. Albajar (MD), S. Balkan (MD), P. Barel (MD), E. Baron (MD), M. Biot (MD), F. Boillot (S), L. Bonte (L), M.C. Bottineau (MD), M.E. Burny (N), M. Cereceda (MD), F. Charles (MD), M.J de Chazelles (MD), D. Chédorge (N), A.S. Coutin (MD), C. Danet (MD), B. Dehaye (S), K. Dilworth (MD), F. Fermon (N), B. Graz (MD), B. Guyard-Boileau (MD), G. Hanquet (MD), G. Harczi (N), M. van Herp (MD), C. Hook (MD), K. de Jong (P), S. Lagrange (MD), X. Lassalle (AA), D. Laureillard (MD), M. Lekkerkerker (MD), J. Maritoux (Ph), J. Menschik (MD), D. Mesia (MD), A. Minetti (MD), R. Murphy (MD), J. Pinel (Ph), J. Rigal (MD), M. de Smet (MD), S. Seyfert (MD), F. Varaine (MD), B. Vasset (MD) (S) Surgeon, (L) Laboratory technician, (MD) Medical Doctor, (N) Nurse, (AA) Anaesthetist-assistant, (Ph) Pharmacist, (P) Psychologist We would like to thank the following doctors for their invaluable help:...

Words: 86687 - Pages: 347

Free Essay

Body Systeem

...otherwise, except for the inclusion of brief quotations in a review, without prior permission in writing from the publisher. Library of Congress Cataloging-in-Publication Data McDowell, Julie. Encyclopedia of human body systems / Julie McDowell. p. cm. Includes bibliographical references and index. ISBN 978–0–313–39175–0 (hard copy : alk. paper) 1. Human physiology—Encyclopedias. I. Title. QP11.M33 2011 612.003—dc22 2010021682 ISBN: 978–0–313–39175–0 EISBN: 978–0–313–39176–7 14 13 12 11 10 1 2 3 4 5 This book is also available on the World Wide Web as an eBook. Visit www.abc-clio.com for details. Greenwood An Imprint of ABC-CLIO, LLC ABC-CLIO, LLC 130 Cremona Drive, P.O. Box 1911 Santa Barbara, California 93116-1911 This book is printed on acid-free paper Manufactured in the United States of America Contents VOLUME ONE About the Editor and Contributors, vii Introduction, ix CHAPTER 1 The Building Blocks of the Human Body, 1 Julie McDowell CHAPTER 2 The Circulatory System, 23 Leslie Mertz CHAPTER 3 The Digestive System, 85...

Words: 218741 - Pages: 875

Free Essay

Analytical Chem

...Analytical Chemistry David Harvey DePauw University Boston Burr Ridge, IL Dubuque, IA Madison, WI New York San Francisco St. Louis Bangkok Bogotá Caracas Lisbon London Madrid Mexico City Milan New Delhi Seoul Singapore Sydney Taipei Toronto McGraw-Hill Higher Education A Division of The McGraw-Hill Companies MODERN ANALYTICAL CHEMISTRY Copyright © 2000 by The McGraw-Hill Companies, Inc. All rights reserved. Printed in the United States of America. Except as permitted under the United States Copyright Act of 1976, no part of this publication may be reproduced or distributed in any form or by any means, or stored in a data base or retrieval system, without the prior written permission of the publisher. This book is printed on acid-free paper. 1 2 3 4 5 6 7 8 9 0 KGP/KGP 0 9 8 7 6 5 4 3 2 1 0 ISBN 0–07–237547–7 Vice president and editorial director: Kevin T. Kane Publisher: James M. Smith Sponsoring editor: Kent A. Peterson Editorial assistant: Jennifer L. Bensink Developmental editor: Shirley R. Oberbroeckling Senior marketing manager: Martin J. Lange Senior project manager: Jayne Klein Production supervisor: Laura Fuller Coordinator of freelance design: Michelle D. Whitaker Senior photo research coordinator: Lori Hancock Senior supplement coordinator: Audrey A. Reiter Compositor: Shepherd, Inc. Typeface: 10/12 Minion Printer: Quebecor Printing Book Group/Kingsport Freelance cover/interior designer: Elise Lansdon Cover image: © George Diebold/The Stock Market Photo...

Words: 88362 - Pages: 354