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Hernandez, Franklin Joseph D.

3FPH Reaction of Acetic Anhydride with Salicylic Acid Procedure: 1) Weigh 2g of Salicylic Acid and place it in a hard glass test tube.
2) Add 5ml of Acetic Anhydride and 5gtts of Sulfuric Acid in the hard glass

test tube with Salicylic Acid. 3) Stir until the Salicylic Acid dissolves. 4) Prepare a beaker filled with three fourths water for the hot water bath. Boil on the hot plate.
5) Turn off the hot plate when it boils. Place the hard glass tube on the

hot water bath with continuous stirring for one minute. Leave the mixture for 20 to 30 minutes. Maintain a temperature of 70-80 degree Celsius as you leave the mixture on the hot water bath. 6) Remove the hard glass tube from the hot water bath. Add 5mL of distilled water on the mixture. 7) Add few drops of distilled water until the mixture becomes turbid or cloudy. 8) Place the hard glass tube on the cold water bath. 9) Add 20mL of cold water on the hard glass tube. Allow the aspirin (ASA) to crystallize for 10 minutes. 10) Filter the mixture using a filter paper and let it dry. Weigh the aspirin (ASA) after drying and compute for the percentage yield. Post-Laboratory: 1) What is the chemical formula of aspirin and salicylic acid? Salicylic acid = C7H6O3 Aspirin = C9H8O4

2) What are the chemical reactions of salicylic acid? Salicylic acid is a carboxylic acid. Carboxylic acids:

Donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt.

Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0.

Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.

In aqueous solution and liquid or molten, carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers.

React with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides geneate flammable and/or toxic gases and heat.

In aqueous solution, can also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.

Reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible.

May initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

3) What is hydrolysis of aspirin? Aspirin (C9H8O4) is hydrolyzed in NaOH solution to form salicylic acid (C7H6O3).
4) What are the uses of aspirin?

Over-the-counter pain relief, especially for headaches Reduction of swelling and inflammation in arthritis and injuries Anti-coagulant given to sufferers of heart attack, mini-stroke and unstable angina Can reduce severity of heart attack if taken at first symptoms Recovery after cardiovascular surgery (eg bypass operation) Treatment of rheumatoid arthritis, osteoarthritis and other rheumatoid diseases Migraine treatment Improving circulation in the gums Fighting ovarian, breast and colon cancer Prevention of cataracts Controlling pre-eclampsia Improving brain function, especially memory Reducing colorectal cancer repeating

Prevention of adult leukaemia Prevention of HIV replicating Reduce prostrate cancer risk Increasing success rates of IVF programs

5) What are the mechanisms of actions of aspirin? Aspirin and other non-steroid anti-inflammatory drugs (NSAIDs): Inhibit the activity of the enzyme now called cyclooxygenase (COX) which leads to the formation of prostaglandins (PGs) that cause inflammation, swelling, pain and fever COX-1, supports the beneficial homeostatic functions COX-2, becomes upregulated by inflammatory mediators and its products cause many of the symptoms of inflammatory diseases such as rheumatoid and osteoarthritis 6) What is your percent yield? Show the solution. SA = 2.025 filter paper = 1.4583 ASA = 3.2412 - 1.4583= 1.783 wt of ASA / wt of SA x 100 = percentage yield 1.783/2.025 x 100 = 88.05% References:
1. Vane, J. R. (2003). The mechanism of action of aspirin. The William

Harvey Research Institute, St. Bartholomews and the Royal London School of Medicine, Charterhouse Square, London EC1M 6BQ, UK.
2. (2007). SALICYLIC ACID: Reactivity Profile. Retrieved (June 21, 2011) from (http://cameochemicals.noaa.gov/chemical/9041). 3. The Synthesis and Characterization of Aspirin. Retrieved (June 21, 2011) from (http://wwwchem.csustan.edu/chem1102h/aspirin/asp_part2.htm).

4. (2003). The use of aspirin. Retrieved (June 21, 2011) from (http://www.wordconstructions.com/articles/health/aspirin.html).