Loading presentation...

Present Remotely

Send the link below via email or IM

Copy

Present to your audience

Start remote presentation

  • Invited audience members will follow you as you navigate and present
  • People invited to a presentation do not need a Prezi account
  • This link expires 10 minutes after you close the presentation
  • A maximum of 30 users can follow your presentation
  • Learn more about this feature in our knowledge base article

Do you really want to delete this prezi?

Neither you, nor the coeditors you shared it with will be able to recover it again.

DeleteCancel

Make your likes visible on Facebook?

Connect your Facebook account to Prezi and let your likes appear on your timeline.
You can change this under Settings & Account at any time.

No, thanks

Experiment 7: Synthesis of Ester Methyl Salicylate

No description
by

Angelo Lazo

on 9 March 2014

Comments (0)

Please log in to add your comment.

Report abuse

Transcript of Experiment 7: Synthesis of Ester Methyl Salicylate

Methyl Salicylate
Toxicity of Methyl Salicylate
To synthesize ester methyl salicylate
Objectives of the Experiment
Reagents
Background
Salicylic Acid
Hexane
Methanol
Sodium carbonate solution
6M HCl
Anhydrous magnesium sulfate
Red Litmus paper
In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate, which is equivalent to more than twenty-three 300 mg aspirin tablets.
used for providing fragrance to various products and as an odor-masking agent for some organophosphate pesticides
naturally found in the bark of sweet birch tree (
Betula lenta
)
Esters are chemical compounds consisting of a carbonyl adjacent to an ether linkage. They are derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol.
Experiment 7: Synthesis of Ester Methyl Salicylate
Esters, whether artificial or natural, are wide used flavorings and perfumes.
used, in high concentrations, as a rubefacient and analgesic in deep heating liniments (such as Bengay) to treat joint and muscular pain
used, in low concentrations (0.04% and under), as a flavoring agent in chewing gum and mints
used as a simulant or surrogate for the research of chemical warfare agent sulfur mustard, due to its similar chemical and physical properties
used as an antiseptic in Listerine mouthwash produced by the Johnson & Johnson company.
Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children.
To become familiar with the method and principle involved in reflux
Materials
Boiling chips
Pipette
Rubber aspirator
Graduated cylinder
Spatula
Stirring rod
Evaporating dish
250-mL beaker
500-ml beaker
Iron ring
Round bottom flask
Condenser
2 rubber tubings
Separatory funnel
Vials
Bunsen burner
Tripod
Water bath
Clamps
Iron stand
Synthesis
Procedure
Place 60 mL methanol, few boiling chips, and 27.6 g salicylic acid in a round bottom flask. Carefully add 7.0 mL conc. sulfuric acid. Mix well then reflux for 2 hours.
Place contents of reaction flask in 400-mL beaker and cool in ice bath until below room temperature.
Slowly add small portions of 20% sodium carbonate solution with constant stirring until solution tests basic with red litmus paper.
Place solution in 250-mL separatory funnel. Extract with 50 ml hexane. Allow two layers to form. Drain off aqueous layer and save in a 400-mL beaker.
Wash hexane solution (extract) remaining in separatory funnel with 25 ml water. Drain water solution into 400 mL beaker containing sodium salt of salicyclic acid.
Dry hexane solution with anhydrous magnesium sulfate. Evaporate hexane on steam bath.
Place sample in a properly labeled and preweighed vial. Determine weight of methyl salicylate obtained and calculate percent yield.
Data and Results
Weight of methyl salicylate - 13.65 g

Theoretical Yield - 30.38 g

Percent Yield - 44.93%
Conclusion
Methyl salicylate is an organic ester naturally produced by many species of plants, specifically wintergreens. It is artificially synthesized to produce perfumes and fragrances, foods and beverages, and liniments.
The process of refluxing involves distillation with condensation of vapors and returning these vapors to the original system. This process is widely used in industrial and laboratory distillations.

Mass of methyl salicylate collected was 14 g. Percent yield was 45%.
Full transcript