220px-FountainSpringsWintergreen.pngHeadaches' Green Relief

Using Wintergreen Oil to Manufacture Aspirin using Green Chemistry Principles

By Jackie Tims Organic Chemisty Fall 2010
Email: jmh262@unh.edu


Introduction
Aspirin is one of the most easily recognizable pharmaceuticals available today and is the world’s most widely used drug: over 25 million kgs are manufactured every year. This makes it an ideal candidate for ‘greening’’.
History and Current Process
My project will involve the investigation of the current manufacturing process and the quantities of raw materials used. I will be researching using contacts within an aspirin producing company (probably Bayer) to identify the waste procedures and any current recycling procedures. I will also be looking into the process in the 1950’s and 1960’s to identify any differences since its first manufacture on a large scale to the current day.
The Greener Process
The older cousins of aspirin, salicigen and salicylic acid have been used as therapeutic drugs since Ancient Greece. Often taken from plant sources such as willow bark, these compounds are inherently ‘greener’. Aspirin can be produced from a common plant extract called wintergreen oil. Wintergreen oil’s common chemical name is methylsalicilate and through a simple experiment can produce aspirin and a fairly benign by product called acetic acid (vinegar).
Green Chemistry Principles

The Experiment
My project will also include the design and execution of this experiment to create aspirin from wintergreen oil. The process will be compared to the commercial process theoretically as the use of benzene in a laboratory is restricted. My project will not be reinventing this experiment as it exists in the GEM database for academic use. I will however like to video the experiment and identify at each stage the benefits or not of the greener process.

The Results

Conclusions
Scaling up the greener process may have its own problems and my projects conclusion will cover the options available, the costs and environmental benefits of each route. With the diminishing of the petroleum supply over the next 50 years, I am sure it will be one big headache if the production of aspirin has not shifted to a more renewable source.


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References

Biesterfeld, R. C., Shaw, D. H., & Taintor, J. F. (1978). Aspirin: An update. Journal of Endodontics, 4(7), 198-202. doi:DOI: 10.1016/S0099-2399(78)80182-4
Butters, M., Catterick, D., Craig, A., Curzons, A., Dale, D., Gillmore, A., Green, S. P., Marziano, I., Sherlock, J., & White, W. (2006). Critical assessment of pharmaceutical processes--A rationale for changing the synthetic route. Chemical Reviews, 106(7), 3002-3027. Retrieved from http://search.ebscohost.com.libproxy.unh.edu/login.aspx?direct=true&db=cmedm&AN=16836307&site=ehost-live
Mehta, A. (2005). Aspirin. Chemical & Engineering News, 83(25), 46-47. Retrieved from http://search.ebscohost.com.libproxy.unh.edu/login.aspx?direct=true&db=aph&AN=17420553&site=ehost-live
Rothwell, P. M., Fowkes, F. G. R., Belch, J. F., Ogawa, H., Warlow, C. P., & Meade, T. W.Effect of daily aspirin on long-term risk of death due to cancer: Analysis of individual patient data from randomised trials. The Lancet, In Press, Corrected Proof doi:DOI: 10.1016/S0140-6736(10)62110-1

Tyagi, B., Mishra, M. K., & Jasra, R. V. (2010). Solvent free synthesis of acetyl salicylic acid over nano-crystalline sulfated zirconia solid acid catalyst. Journal of Molecular Catalysis A: Chemical, 317(1-2), 41-45. doi:DOI: 10.1016/j.molcata.2009.10.019