Synthesis of salicylic acid from methyl salicylate. Synthesis of Salicylic Acid from Wintergreen Oil 2019-01-09
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Chemistry 211 Experiment 3
The contents of the round bottom flask then underwent vacuum filtration through a Hirsch Funnel fit with filter paper and connected with an integral adapter to a 25mL filter flask. Measuring the melting point gives direct information. Why is it that dilute sulfuric acid does not allow the reaction to proceed while concentrated sulfuric acid does? Please see for additional information about using Turnitin via Canvas. What is the percent yield? The purpose of this lab is to determine the difference between salicylic acid made from methyl salicylate and salicylic acid made from benzene comparing the melting points of the two samples. Sodium salicylate, a predecessor to aspirin, was developed along with salicylic acid in 1875 as a pain reliever. A single teaspoon 5 ml of methyl salicylate contains approximately 6 g of salicylate, which is equivalent to almost twenty 300 mg tablets 5 mL × 1.
That will not be the case with all solvents. The sample became a cloudy white color. To make sure we get the most product out of the reaction excess ensures product formation in high yield e. Always read all digits off the balance. Let the vacuum continue to be drawn through the Buchner funnel for about 15 minutes to thoroughly evaporate the solvent. Mizukami Abstract Acetylsalicylic acid, or also known as aspirin is known to be a drug that relives people of pain and is commonly used even today.
Essay on Synthesis of Salicylic Acid from Wintergreen Oil
Filter the solution through one or two coffee filters, squeezing the filters into the filtrate afterward to recover some of the liquid. From which a molecule of alcohol and a molecule of carboxylic acid are obtained. Somehow need molecules to collide to get over activation barriers to form product heating is required. Do not follow the instructions in the Presenting Spectral Data in Lab Reports handout. The reaction mixture is subsequently acidifed using sulfuric acid, which converts this anion into the fully protonated acid, salicylic acid.
This process is widely used in industrial and laboratory distillations. If you're nervous about it escaping or getting attacked, use a KimWipe secured with a rubber band on the top of the beaker. Methyl salicylate produces a minty odor after it was placed in a water bath for 15 mi nutes. Next, using grease on the glass joint, a water jacketed condenser was added to the round bottom flask. There are only three types of compounds which have an oxygen located between two carbons. At this point, remove from heat, and feel the edges of the container. After cooling, collect the crystals by vacuum filtration.
Mass of methyl salicylate used: 0. The C that is lost was bonded to 2 Oxygen molecules making it down stream whihc is congruent with the chemical equaiton. Boil the water until you are sure that all of the salicylic acid has dissolved, then slowly cool the beaker, and finally chill it in a refrigerator or ice bath. Esters are also used commercially as solvents, plasticizers, starting materials for polymers, as well was pharmaceuticals. It wasn't until the 1970's, when British pharmacologist John Vane, Ph.
Synthesis of Salicylic Acid from Wintergreen Oil Essay
This information can be found by comparing the difference in melting points of the two samples of Salicylic Acid. Salicylic acid is a white crystalline compound that can be isolated from the bark of birch trees. Store them in a glass or plastic container prior to use. Salicylic acid, the product is not soluble in water H2O during room temperature. The advantage of using acetic anhydride is that you do not produce water which can be used for hydrolysis of the newly formed ester. The first involves the hydrolysis of methyl salicylate in order to produce salicylic acid Day 1. If your recrystallization goes awry and you end up with no purified product, at least you have a crude weight to use to calculate your percent yield and some sample for a melting point.
The melting point range was slightly wider, though did encompass the accepted melting point values. Methyl salicylate was first isolated in pure form in 1843 by extraction from wintergreen plant Gaultheria. Loss of product occurred due to loss at each transfer step including, crystals stuck to the vacuum filter, crystals sticking to the glass stir rod for pH testing as well as the metal spatula used for recrystallization. The salicylic acid produced in this part of the experiment will be used to prepare acetylsalicylic acid aspirin Day 2. This soon became the pain killer of choice for physicians around the globe.
Candles can also be made from beeswax, soy, other plant waxes, and tallow a by-product of beef-fat rendering. Assuming you haven't lost too much of your salicylic acid, add about 10 mL of water to the beaker still containing the crystals for every gram of salicylic acid you expect to obtain, as we are going to recrystallize it. The use of a preheated melting point device heated to about 110 oC will help to minimize this decomposition. Mass of methyl salicylate collected was 14 g. It is used as a penetrating oil to loosen rusted parts. Methyl salicylate can be produced through esterification of salicylic acid with methanol in the presence of an acid catalyst, particularly sulfuric acid, providing a large amount of Hydrogen ions and speeding up the rate of reaction.
Add the powdered acetylsalicylic acid obtained from steps 1-5 or otherwise to a clean beaker, and add enough 10% hydrochloric acid solution to cover them completely, plus another few centimeters. Methyl salicylate is probably produced as an anti- defense. The melting point range was slightly wider, though did encompass the accepted melting point values. It may be necessary for you to gravity filter this solution. Methyl salicylate, an ester derived from the combination of salicylic acid and methanol, is also known as the oil of wintergreen. Introduction: Esters are formed from the reaction of acids and alcohols: O O… caproic acid was synthesized in a multi-step process that involved the synthesis of three intermediates — diethyl n-butylmalonate, potassium n-butylmalonate, and n-butyl malonic acid respectively.
