Synthesis of Aspirin

Group: 3- strawberries

Aspirin: some background

Patented by Bayer in 1893 One of the oldest drugs One of the most consumed drugs (Production in the US is 10 million Kg/year)

Aspirin is a member of a family of chemicals called salicylates.

Reverend Edmund Stone wrote about the success of the bark and the willow in the cure of the "agues," or fevers with aches.

Scientists found out that the part of willow bark that was (1) bitter and (2) good for fever and pain is a chemical known as salicin. Felix Hoffmann put the compound through a couple of chemical reactions that covered up one of the acidic parts with an acetyl group, converting it to acetylsalicylic acid (ASA).

Aspirin: Biological activity

Analgesic (painkiller) Antipyretic (fever reducer) Anti-inflammatory (inhibition of the synthesis of prostaglandins)

Side effects: gastric irritation, bleeding Apparition of new analgesics (Tylenol)

Importance and application:

Fungal infections on soil is one problem some gardeners face. Do you know that aspirin helps to keep cut flowers to be fresh for a longer period of time? Having dandruff problems? If you are a smoker, certainly you will have nicotine stains on your fingers. Pimples? Don't worry. Aspirin can be used to remove sweat stains from T-shirts. When making compost for your garden or greenhouse mixing, it with aspirin will prevent fungus forming around the roots of new plants. If your hair had become yellowish or faded from the chlorine content in a swimming pool, it can be corrected very quickly. Mosquito bites and bee stings can be eased by wetting the skin and rubbing an aspirin over the spot.

Aspirin: The Molecule

O

OH

acetyl salicylic acid (aspirin)

The Esterification Process

*Aspirin can be made by using a process called esterification. *Esterification occurs when a carboxylic acid and an alcohol combine in a reaction to produce an ester. This reaction can be used to synthesize aspirin from salicylic acid. *In the lab, the carboxylic acid alcohol mixture is heated in the presence of H2SO4, sulfuric acid, which acts as a catalyst. *During the reaction process, a molecule of water splits off and the remaining carboxylic acid and alcohol fragments become attached producing an ester.

Purification by Recrystallization
WHAT IS RECRYSTALLIZATION?

METHOD

Rapid and convenient way of purifying a solid organic compound The material to be purified is dissolved in the hot appropriate solvent As the solvent cools, the solution become saturated with respect to the substance, which then crystallize Impurities stay in solution

Choose the solvent Dissolve the solute (Filter suspended solids) Crystallize the solute Collect and wash the crystals Dry the crystals

Assessment of purity: Looking for properties

Physical properties

Chemical properties

Physical appearance Solubility Melting point Physical state (solid? liquid? ..) Color

Percent yield Potentiometric titration Phenol test

Testing For Impurities

LEFT - pure (no phenol present), RIGHT - impure (phenol present)
Purple color when FeCl3 added - impure product, salicylic acid present. Unreacted salicylic acid is present.

We use iron III chloride to determine the purity of our aspirin. Iron III chloride combines with the phenol group to form a purple complex. If salicylic acid is present (impurity) the product will turn purple when FeCl3 is added, because salicylic acid is a phenol.

Result:
Compound Theoretical Yield (g) Actual Yield (g) Percent Yield

Acetylsalicylic acid

1.06g

0.76g

72%

Table 1. The theoretical yield of acetylsalicylic acid based on the amount of salicylic acid used for the reaction. Compound Acetylsalicylic acid Observed m.p. ( C) 120-121 Literature m.p. (C) 138

Table 2. The observed melting point of acetylsalicylic acid compared to its literature melting point.

Calculation of mass of crude product before recrystallization of aspirin: Mass of 125mL Erlenmeyer flask = 91.73g Mass of flask w/ crude product = 93.85g (Mass of flask w/ crude product) (Mass of flask) = Mass of crude product 93.85g 91.73g = 2.12g crude produc

Conclusion:

The experiment did not go completely as expected. The reaction yielded only 72% of itsexpected product. The purity of the aspirin was not very high, which is evident by the low melting point when compared to the literature value. we are therefore conclude that aspirin has many useful uses not only in medical field but also for regular disease like the stated in the importance and use. also we were able to learn and recall how to compute molar mass.

Reference:

1. Rowland, A.T.; Allen K. Clark; Carl T. Wigal; Charles E. Bell, Jr.; Douglass F. Taber; Frederick A. Bettelheim; Jan William Simek; Jerry Manion; Joe Jeffers; Joseph M. Landesberg; Joseph W. LeFevre; L.G. Wade, Jr.; Louis J. Liotta; Moses Lee; Ronald J. Wikholm; and William M. Loffredo. Organic Chemistry Laboratory Manual: Susquehanna University. Thomson Learning: Ohio, 2003. 2. Benzaia, Diana. 2003. Hospital for Special Surgery. http://www.hss.edu/Conditions/Arthritis/Aspirin---Caution-Required. Accessed 15, Sept. 2004. 3. Dr. Carman. 2002. University of Nevada. http://tooldoc.wncc.nevada.edu/aspirin.htm. Accessed 18, Sept. 2004. 4. Henry, Dr. Geneive. 2004. Susquehanna University. Synthesis of