Lab Report

Extracting Vanillin from Artificial Vanilla Extract:
Laboratory Report

Kaylan Clarke

Department of English, City College of New York

ENGL 21007: Writing for Engineering

Prof. Kristen M. Slentz

January 05, 2025

Abstract

Vanilla extract is a very popular flavor addition to foods, component of cosmetics, and has biomedical applications as well. Vanillin is the compound that gives vanilla its characteristic flavor and aroma. It is often synthesized from guaiacol to be put in vanilla extract. This vanillin can be successfully extracted using a DCM wash to dissolve the vanillin, then distilling and recovering the DCM. In the video by NileRed, 0.4g of vanillin crystals were extracted. Though this yield is lower than if washed with diethyl ether, DCM is easier to obtain and therefore more suitable for classroom applications, where this experiment is most useful. Extracting vanillin in this way would not be practical for mass production or industrial uses because of the excessive waste of vanilla extract and relatively low yield. However, in academic settings, it can help students learn solubility concepts, extraction methods, and how to use the various equipment apparatus.

Keywords: Artificial Vanilla Extract, Vanillin, DCM

Introduction

Vanilla is a common component of foods and scented items. Though once a luxury, the word “vanilla” has come to be synonymous with “default” or “bland” (Mishan & Melamed 2023). It is used in countless foods and drinks, but also in cosmetics including skincare, as well as perfumes. In addition, it has pharmaceutical applications as a chemical precursor for drugs (Liaqat et al., 2023). Vanillin is also a precursor molecule to capsaicin, which is the compound naturally occurring in peppers that makes them spicy (NileRed, 2015). The many common uses of vanilla extract means its demand is high, and the rate of production needs to match this intense consumer demand.

Vanilla products’ characteristic flavor and scent comes from the compound vanillin. Vanillin is what is in both natural and artificial vanilla extract. Natural vanilla extract uses vanillin harvested from vanilla beans while artificial extract uses synthetically produced vanillin. As Mishan and Melamed (2023) describe, the process for growing, harvesting and extracting vanillin from vanilla beans is extremely labor intensive. There is only a small amount of vanillin present in vanilla beans, and it is difficult to extract because of the other components in the natural bean. Additionally, the maximum yield for natural vanillin is 2% at best (Liaqat et al., 2023). These factors make natural vanillin much more expensive than its artificial counterpart. Consumer demand for more natural products is a relatively recent trend, beginning mostly in the last decade. However, the difficulty of creating natural vanilla extract makes it impossible for the supply to keep up with consumer demand.

Synthetic vanillin is the most common form for making vanilla extract. 99% of vanilla extract used is artificial. The majority comes from a byproduct of petrochemicals called guaiacol or from a byproduct of wood processing (Mishan & Melamed 2023). As opposed to natural vanilla extract, which contains many other compounds within the bean, synthetic vanilla extract is a much better candidate for vanillin extraction because it generally only contains vanillin.

The extraction of vanillin from artificial vanilla extract can be done with diethyl ether as a solvent. However, diethyl ether is highly flammable and difficult to obtain. Dichloromethane (DCM) has similar properties that make it convenient as a substitute. Like diethyl ether, dichloromethane is a solvent often used in extractions. It is used to dissolve organic compounds (CH2Cl2 – Dichloromethane, 75-09-2 – Kemicalinfo, 2023). DCM has a low boiling and evaporation point, which means it is good for recovering solute (in this case the vanillin) through distillation.

This experiment is useful for classroom applications, as it is simple enough for beginner or intermediate students to practice using laboratory apparatus, extraction methods, purity testing, and application of the scientific method. An appropriate hypothesis is that because vanillin is soluble in DCM, and because artificial vanilla is mostly synthetic vanillin, it is possible to extract pure vanillin from artificial vanilla extract using DCM as a solvent.

Materials

  • 500 ml artificial vanilla extract (brand unspecified)
  • Approximately 300 ml of DCM
  • Sodium Chloride (NaCl) solution
  • Calcium Chloride (CaCl2)
  • 1 L separatory funnel, stand, and clamp
  • 500 ml round bottle flask
  • Erlenmeyer flasks
  • Beakers
  • Distillation apparatus
  • Vacuum filter apparatus
  • Water

Methods

  1. Attach the separatory funnel to the stand using the clamp.
  2. Set up a vacuum filtration apparatus with a 500mL round bottle flask attached.
  3. Set up a distillation apparatus.
  4. To the funnel, add 500ml of artificial vanilla extract
  5. Pour in 60 ml of DCM and detach the funnel from the stand to shake the mixture gently but thoroughly to avoid emulsion.
  6. Place the funnel back onto the stand and allow the layers to separate. Drain the clear, lower DCM layer into an Erlenmeyer flask.
  7. Repeat this washing process three more times for a total of four washes.
  8. Discard the leftover vanilla extract from the funnel and clean the funnel. Place it back onto the stand.
  9. Pour the DCM solution from the flask into the clean funnel and wash the flask with a small amount of DCM to ensure most of the solution makes it into the flask. The layer will be a bit cloudy.
  10. To dry the organic layer, add 60 mL of saturated NaCl solution. Remove and shake the funnel, then allow the layers to settle by placing the funnel back onto the stand.

11. The lower DCM layer should now be clear. Drain it into a clean Erlenmeyer flask.

12. Add (unspecified amount) of calcium chloride into the DCM solution to dry it.

13. Pour the calcium chloride and DCM solution into the vacuum filter to collect the filtrate in a 500 mL round bottle flask. To ensure all the calcium chloride is filtered, wash the flask with a small amount of DCM and pour into the filter, also collecting into the round bottle flask.

    14. Remove and recover the DCM by distilling it. A small amount of yellow oil of vanillin will be left over. Transfer this oil to a small beaker.

      15. Allow the vanillin oil to sit at room temperature and crystallize.

        16. Use water to recrystallize the vanillin. Ensure the water is below vanillin’s melting point (80℃) so that it doesn’t revert to oil.

        17. Filter and dry the crystals.

          Results

          Pure vanillin crystals were successfully extracted from artificial vanilla extract using DCM as solvent. The experiment yielded about 0.4 g of vanillin. Given that the average range of vanillin per bottle of artificial vanilla extract is 1 to 4 grams, the actual yield was 10% to 40% of the theoretical yield. The crystals were white in color, a characteristic indicative of both their identity as vanillin and a relatively high purity.

          Actual Yield (g)Theoretical Yield (g)Percent Yield
          0.41 to 410% to 40%

          More evidence of purity is provided by an NMR test. NMR tests show how the different atoms in a molecule interact with each other, making it possible to determine the chemical structure of the molecule. Comparing this result to the expected chemical structure shows how pure a substance is. The NMR spectrum is further evidence that the resultant crystals are relatively pure, though this does not represent an overall, quantitative number for purity.

          Discussion

          The experiment proved the hypothesis correct, demonstrating that it is possible to extract vanillin from artificial vanilla extract. As NileRed said in his video, the amount of vanillin in the extract depends on the brand used. The average range is 1 to 4 grams per 500 mL, so this yield is low. This may have been due to the brand of vanilla extract used, as different brands contain different levels of vanillin. Diethyl ether would have extracted more vanillin than DCM. NileRed theorizes that because DCM tends to form emulsions, it had to be shaken gently with the vanilla extract. An emulsion needed to be avoided because it would prevent the layers from separating. If diethyl ether had been used, the mixture could’ve been shaken more vigorously because it wouldn’t form an emulsion.

          The purity test NileRed used was an NMR. The peaks on the spectrum correspond to expected molecular structure. Any peaks that do not align with the expected molecular spectrum would represent impurities. The spectrum provided in the video done with the resultant vanillin crystals shows the relatively high purity of the product. Alternative methods for testing purity in this case include analysis under a microscope and melting point analysis. Chemist myst32YT conducted a similar experiment, and observed his crystals had a long and thin shape indicating they are pure. He also used a melting-point apparatus to check if the melting point of his vanillin matched that of the documented melting point, 80℃. A closer match indicates a purer product (myst32YT, 2010).

          Conclusion

          This extraction process was successful despite the low yield of vanillin. The experiment demonstrated that it is possible to extract relatively pure vanillin from synthetic vanilla using DCM as an organic solute. It could help students learn to use common laboratory materials. This experiment is a good opportunity to teach about the properties of common organic solvents like DCM and diethyl ether. Instructors may also find this particularly useful for demonstrating the concepts of solubility, as the vanillin’s ability to dissolve in DCM is what makes this experiment possible. In addition, instructors can teach proper methods for getting the highest yield possible from extraction, and distillation and filtering practices. The product would also allow students to practice NMR testing.

          For industrial applications, this would be a roundabout and impractical way to source vanillin from vanilla extract. Though simpler than natural extract, synthetic vanilla extract has many other components that go into making it, and by weight very little of a bottle of extract it is pure vanillin. Using this method to extract vanillin would produce more waste than product. Even in the unlikely case where this is a cheaper method than buying from a supplier in bulk, the labor, waste management costs, and increased emissions from extra processing would likely outweigh any savings. Overall, buying vanilla extract solely to produce a small amount of pure vanillin while dealing with the resulting waste and byproducts is highly wasteful and likely would come at a cost deficit.

          References

          CH2Cl2 – Dichloromethane, 75-09-2 – Kemicalinfo. (2023, March 2). Kemicalinfo. https://kemicalinfo.com/chemicals/ch2cl2-dichloromethane/

          Liaqat, F., Xu, L., Khazi, M. I., Ali, S., Rahman, M. U., & Zhu, D. (2023). Extraction, purification, and applications of vanillin: A review of recent advances and challenges. Industrial Crops and Products, 204, 117372. https://doi.org/10.1016/j.indcrop.2023.117372

          Mishan, L., & Melamed, M. (2023, September 8). How Did Vanilla Become a Byword for Blandness? The New York Times. https://www.nytimes.com/2023/09/08/t-magazine/vanilla-spice-blandness.html

          myst32YT. (2010, December 4). Use Diethyl ether to Extract Vanillin from Artificial Vanilla. YouTube. https://www.youtube.com/watch?v=k7ZDSFEsrGg

          NileRed. (2015, January 13). How to isolate Vanillin from Artificial Vanilla Extract. Youtube. https://www.youtube.com/watch?v=skS8SKJrZYc

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