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Aspirin Research Project

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Transfer-Encoding: chunked ´╗┐Should the management of Aspirin be altered as a result of the adverse effects it presents? Introduction Aspirin is a common drug which is utilised for medicinal purposes around the globe. Furthermore, the drug itself is a synthetic organic compound derived from the salicylic compound group (International Aspirin Foundation, 2016). Although, aspirin may possess medicinal benefits it also poses detrimental effects to society and the environment. Hence, an issue regarding its usage is should the management of aspirin be altered as a result of the adverse effects it presents? This issue is relevant on a social level as its usage is common within societies throughout the world. Likewise, the implications of its harmful effect raise immediate concerns for the public as their safety is of importance. http://upload.wikimedia.org/wikipedia/commons/b/b0/Aspirin-skeletal.png Chemical Background Aspirin is known as acetylsalicylic acid and possesses a chemical formula of C9H8O4 (International Aspirin Foundation, 2016). Furthermore, it is a synthetic compound from the group of salicylates. Additionally, it is an aromatic compound which consists of an ester and carboxylic acid functional group (International Aspirin Foundation, 2016). Figure 1 reflects the chemical structure of aspirin (acetylsalicylic acid). Aspirin is produced through the reaction of salicylic acid and acetic anhydride with the utilisation of an acidic catalyst (Pillai, 2015). However, the salicylic acid necessary for this production is prepared through a variety of different reactions. Initially, phenol (hydroxybenzene) is reacted with sodium hydroxide to produce sodium phenoxide (Pillai, 2015). http://3.bp.blogspot.com/-wAAwqltqXWM/Ta3XpoI5a1I/AAAAAAAAABg/bpSsNi6VfQ8/s1600/OH.gif http://www.sigmaaldrich.com/content/dam/sigma-aldrich/structure2/051/mfcd00013134.eps/_jcr_content/renditions/mfcd00013134-medium.png + NaOH ? + H2O C6H5OH + NaOH ? C6H5ONa + H2O Phenol + Sodium Hydroxide ? Sodium Phenoxide + water (Pillai, 2015) In effect, the sodium phenoxide produced is reacted further with carbon dioxide to produce sodium salicylate (Royal Society of Chemistry, 2003). http://www.sigmaaldrich.com/content/dam/sigma-aldrich/structure2/051/mfcd00013134.eps/_jcr_content/renditions/mfcd00013134-medium.png https://www.emdmillipore.com/waroot/medium/567630%5b567630-ALL%5d.jpg + CO2 ? C6H5ONa + CO2 ? C6H4OHCOONa Sodium Phenoxide + Carbon Dioxide ? Sodium salicylate (Royal Society of Chemistry, 2003) Thus, the sodium salicylate is treated with an acid to produce salicylic acid and a sodium compound which is dependent on the acid utilised (Brown, 2016). ...read more.


G. (2015, May 3). Introduction to Preparation of Salicylic Acid. Retrieved April 10, 2015, from Slide Share: http://www.slideshare.net/yagnesh96/introduction-and-preparation-of-salicylic-acid Statista. (2016). Bayer AG's top pharmaceutical products from 2010 to 2015, based on revenue (in million euros). Retrieved April 13, 2016, from Statista: http://www.statista.com/statistics/263787/revenues-of-bayers-top-pharmaceutical-products/ unknown. (2012, June 11). Aspirin Should it be the Ideal Medicine. Retrieved April 13, 2016, from Aspirin Positive Negative Effects: http://aspirinpositivenegativeeffects.weebly.com/blog.html Weiner, D. L. (2015, April 2). Reye Syndrome. Retrieved April 15, 2016, from Medscape: http://emedicine.medscape.com/article/803683-overview Article Murdoch, K. (2015, May). Pharmaceutical Pollution in the Environment:Issues for Australia, New Zealand and. National Toxics Network, pp. 5-9. Images for equations Galtra Inc, (2014), Phenol Chemical Structure [ONLINE]. Available at:http://www.galtra.net/v2/index.php/intermediates/86-phenol [Accessed 9 April 2016]. Lukáš Mižoch, (2006), Acetic Anhydride Chemical Structure [ONLINE]. Available at:https://commons.wikimedia.org/wiki/File:Acetic_anhydride.svg [Accessed 11 April 2016]. Merck Millipore, (2016), Sodium Salicylate Chemical Structure [ONLINE]. Available at:http://www.merckmillipore.com/GT/en/product/Sodium-Salicylate---CAS-54-21-7---Calbiochem,EMD_BIO-567630 [Accessed 10 April 2016]. Sigma Aldrich, (2016), Acetylsalicylic acid Chemical Structure [ONLINE]. Available at:http://www.sigmaaldrich.com/catalog/product/sigma/a5376?lang=en®ion=AU [Accessed 11 April 2016]. Sigma Aldrich, (2016), Sodium Phenoxide Chemical Structure [ONLINE]. Available at:http://www.sigmaaldrich.com/catalog/product/aldrich/cds001581?lang=en®ion=AU [Accessed 11 April 2016]. Yikrazuul, (2009), Salicylic Acid Chemical Structure [ONLINE]. Available at:https://commons.wikimedia.org/wiki/File:Salicylic_Acid.svg [Accessed 10 April 2016]. Images Charles E Ophardt, (2003), Aspirin effect on COX Enzyme Necessary for Prostaglandin Production[ONLINE]. Available at: http://chemistry.elmhurst.edu/vchembook/555prostagland.htmlaspirin [Accessed 12 April 2016]. Jim Clark, (2013), Energy Profile Diagram reflecting effect of Catalyst [ONLINE]. Available at:http://www.chemguide.co.uk/physical/basicrates/catalyst.html [Accessed 10 April 2016] Kristie Murdoch, (2015), Pathway of Pharmaceuticals into the environment [ONLINE]. Available at:http://www.ntn.org.au/wp/wp-content/uploads/2015/05/NTN-Pharmaceutical-Pollution-in-the-Environment-2015-05.pdf [Accessed 29 April 2016]. Wikipedia, (2014), Chemical Structure of Aspirin [ONLINE]. Available at:https://en.wikibooks.org/wiki/Structural_Biochemistry/Aspirin [Accessed 9 April 2016]. Student response Research skills Information source (correctly formatted reference) Flower, R, 2003. What are all the things that aspirin does?. The BMJ, [Online]. 327, 572-573. Available at: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC194070/ [Accessed 14 April 2016]. Relevant information highlighted in materials submitted Communication Description of information The information provided is an extract from an esteemed online medical journal known as ‘the BMJ.’ Analysis Relevance (the degree to which the source addresses the topic) ...read more.


and acetic acid (ethanoic acid). Sulfuric acid or phosphoric acid are often used to catalyse the reaction. salicylic acid + acetic anhydride (ethanoic anhydride) [H2SO4] ? aspirin (acetylsalicylic acid) + acetic acid (ethanoic acid) http://www.ausetute.com.au/images/saliacid.gif + http://www.ausetute.com.au/images/ethanhyd.gif [H2SO4] ? http://www.ausetute.com.au/images/aspirin.gif + CH3COOH C7H6O3(s) + C4H6O3(l) [H2SO4] ? C9H8O4(s) + C2H4O2(aq) Salicylic acid can react with acetic (ethanoic) acid in an esterification reaction, but the reaction is very slow, taking days to reach equilibrium, and the yield is low: salicylic acid + acetic acid (ethanoic acid) [H2SO4] ? aspirin (acetylsalicylic acid) + water http://www.ausetute.com.au/images/saliacid.gif + CH3COOH [H2SO4] ? http://www.ausetute.com.au/images/aspirin.gif + H2O C7H6O3 + C2H4O2 [H2SO4] ? C9H8O4(s) + H2O For this reason, the commercial preparation of aspirin relies on the faster reaction between salicylic acid and the more reactive acetic anhydride which produces a greater yield of aspirin. Reactions of Aspirin (acetylsalicylic acid) 1. Neutralization: acid + base ? salt + water aspirin (acetylsalicylic acid) + sodium hydroxide ? a salt (sodium acetylsalicylate) + water http://www.ausetute.com.au/images/aspirin.gif + NaOH(aq) ? http://www.ausetute.com.au/images/aspirinna.gif + H2O(l) C9H8O4(s) + NaOH(aq) ? C9H7O4(s)-Na+ + H2O(l) 1. The neutralization reaction can be used to determine the amount of aspirin (acetylsalicylic acid) present in commercially available aspirin tablets using a back (indirect) titration method. 2. Reaction with carbonate: acid + carbonate ? salt + carbon dioxide + water aspirin (acetylsalicylic acid) + sodium hydrogen carbonate ? a salt (sodium acetylsalicylate) + carbon dioxide gas + water http://www.ausetute.com.au/images/aspirin.gif + NaHCO3(aq) ? http://www.ausetute.com.au/images/aspirinna.gif + CO2(g) + H2O(l) C9H8O4(s) + NaHCO3(aq) ? C9H7O4(s)-Na+ + CO2(g) + H2O(l) 1. The reaction with bicarbonate (hydrogen carbonate ion) is commonly used to prepare the salt of aspirin which is more soluble in water than the molecular form of aspirin. 2. Hydrolysis: cleavage of a covalent bond in a molecule by reaction with water aspirin (acetylsalicylic acid) + water ? salicylic acid + acetic acid (ethanoic acid) http://www.ausetute.com.au/images/aspirin.gif + H2O(l) ? http://www.ausetute.com.au/images/saliacid.gif + CH3COOH(aq) C9H8O4(s) + H2O(l) ? C7H6O3(s) + C2H4O2(aq) 1. Old aspirin tablets may have a smell like vinegar as a result of the hydrolysis reaction producing acetic acid (ethanoic acid). Page | ...read more.

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