Tracing the reaction process using thin-layer chromatography

The original language of this article is Chinese and parts of it have been translated using DeepL 

  This experiment uses thin layer chromatography to trace the progress of a chemical reaction. Specifically, you make something called an esterification reaction with acid and alcohol, and then use a special kind of paper to see how the reactants and products change.

  Esterification is an organic chemical reaction in which an acid and an alcohol interact to produce a substance called an ester, which also gives off water.

 Esters are substances that have a fragrance, for example perfumes, flavours and fragrances all contain esters. This reaction is slow, so you need to heat or add a catalyst to speed up the reaction. I use sulphuric acid as a catalyst, which facilitates the reaction between the acid and the alcohol, but does not participate in the reaction so it does not affect the final result. I use acetic acid and ethanol as reactants, they produce an ester called ethyl acetate, which has a fruity smell and is very pleasant. (Don't smell it)

 To do the experiment, I first measured 10 ml of acetic acid and 10 ml of ethanol in a measuring cylinder and then poured them into a round-bottomed flask. Next, I used a dropper to put a few drops of sulphuric acid in and then stirred well with a stirring rod. I then placed the flask on an electric hot plate and heated it to boiling while connecting the flask to another collection flask with a water condenser so that the esters and water produced by the reaction could be separated out. I let the reaction run for about half an hour, then turned off the power and let the flask cool down.

 To observe the results, I first filtered the liquid from the collection bottle using a funnel and filter paper to remove some impurities. Then I used a syringe to split the liquid into two parts, one for thin layer chromatography and the other for scenting. Thin-layer chromatography is a method of analytical chemistry that can be used to analyse the different components of a mixture. Specifically, a special paper is used as the stationary phase and then a solvent is used as the mobile phase. The solvent is allowed to move up the paper, driving the different components of the mixture over different distances, thus creating different spots. In this way it is possible to determine which components are in the mixture and their relative content based on the position and colour of the spots.

 To do the thin layer chromatography, I first cut the paper into a rectangle with a pair of scissors and then used a needle to draw a line on the underside of the paper, which was the starting line. I then used the needle to put a drop of reaction solution on the starting line, along with a drop of acetic acid and a drop of ethanol as a control. I then placed the paper in a beaker with solvent so that the solvent was just above the starting line. I then covered the beaker with a plastic bag to prevent the solvent from evaporating. I waited for about ten minutes before I saw the solvent move up the paper, driving different spots. I used a pen to draw a line where the solvent had moved to, which was the termination line. I then took the paper out and let it dry.

 The results were such that I saw two colours of spots in the reaction solution, one yellow and one purple. The yellow spot overlaps with the spot of acetic acid, which means that there is still acetic acid in the reaction solution that has not completely reacted. The purple spot does not overlap with the ethanol spot, which means that ethyl acetate has been formed in the reaction solution. I used a formula to calculate the relative amount of ethyl acetate in the reaction solution and it was about 60%. This shows that my experiment is not perfect and there is still a lot of room for improvement.

 
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Attachments

Original lab notes, in Japanese, PDF format

Original lab report, in Japanese, PDF format

 

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