Ibuprofen: Original Versus Green Synthesis
Keywords:
Ibuprofen, green synthesis, atom economy, environmentally friendly
Abstract
This paper makes a parallel between the original route versus the green route of Ibuprofen (non-steroidal anti-inflammatory drugs most commonly recommended) synthesis. The original route contained six steps with stoichiometric reagents (some reagents are very toxic: hydrochloric acid, ammonia), a lot of intermediate products, relatively low atom efficiency equal to 40.04% and substantial inorganic salt formation (aluminium trichloride hydrate). The green route of Ibuprofen synthesis developed only three steps, a lower amount of waste and by-products (only acetic acid that can be used for another applications) and an atom efficiency of 77.44%. The green route for Ibuprofen synthesis is an exquisite example of a simple and elegant chemical/pharmaceutical manufacturing process and the nearly complete atom utilization of this streamlined process truly makes it a wasteminimizing, environmentally friendly technology.
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[4]. Oliveira T. C. D., Lima J. F. D., Colaço M. V., Jesus L. T., Freire R. O., Marques L. F., Synthesis, characterization and spectroscopic studies of binuclear lanthanide complexes containing the anti-inflammatory drug Ibuprofen and CH3-disubstituted bipyridine ligands: Influence of methyl group position in the photoluminescence, Journal of Luminescence, vol. 194, p. 747-759, 2018.
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[7]. Rainsford K. D., Ibuprofen: pharmacology, efficacy and safety, Inflammopharmacology, vol. 17, p. 275-342, 2009.
[8]. ***, https://pubchem.ncbi.nlm.nih.gov.
[9]. Lancaster M., Green Chemistry. An Introductory Text, Publisher the Royal Society of Chemistry Cambridge, U. K., ISBN 0-85404-620-8, 2002.
[10]. Thomas K. et al., Growing the Green Economy Through Green Chemistry and Design for the Environment A Resource Guide for States and Higher Education, A joint report by The Green Chemistry and Commerce Council Lowell Centre for Sustainable Production at the University of Massachusetts Lowell and The National Pollution Prevention Roundtable, Issued Publication Number 09-04-010, 2009.
[11]. Clark J., Macquarrie D., Handbook of Green Chemistry and Technology, Publisher Blackwell Science Ltd., ISBN 978-0-632-05715-3, 2002.
[12]. Dunn P. J., Wells A. S., Williams M. T., Green Chemistry in the Pharmaceutical Industry, Publisher Wiley‐VCH Verlag GmbH & Co., Print ISBN:9783527324187, 2010.
[13]. Manahan S. E., Green Chemistry and the Ten Commandments of Sustainability, 3rd edition, Publisher: Chem Char Research Inc., 2010.
[14]. Doble M., Rollins K., Kumar A., Green Chemistry and Engineering, 1 st edition, Imprint Academic Press, eBook ISBN: 9780080524771, 2007.
[15]. Dicks A., Hent A., Green Chemistry Metrics: A Guide to Determining and Evaluating Process Greenness, Publisher: Springer, Springer Briefs in Green Chemistry for Sustainability, ISBN 3319105019, 2015.
[16]. Wardencki W., Curlo J., Namieoenik J., Green ChemistryCurrent and Future Issues, Polish Journal of Environmental Studies, vol. 14, p. 389-395, 2005.
[17]. Evelo C. T., Spooren A. A., Bisschops R. A., Baars L. G., Neis J. M., Two mechanisms for toxic effects of hydroxylamines in human erythrocytes: involvement of free radicals and risk of potentiation, Blood Cells, Molecules and Diseases, vol. 3, p. 280-295, 1998.
[18]. Riemann H., On the Toxicity of Hydroxylamine, Acta pharmacologia, vol. 6, p. 285-292, 1950.
[19]. Hecnar S. O., Acute and chronic toxicity of ammonium nitrate fertilizer to amphibians from southern Ontario, Environmental Toxicology and Chemistry, vol. 14, p. 2131-2137, 1995.
[20]. Cann M. C., Connelly M. E., The BHC Company Synthesis of Ibuprofen, a Greener Synthesis of Ibuprofen Which Creates Less Waste and Fewer Byproducts, chapter from “Real World Cases in Green Chemistry”, p. 19-24, Publisher American Chemical Society, Washington DC, 2000.
[21]. Bond G. C., Webb G., Malonowski S., Marczewski M., Catalysis, Chapter 4: Catalysis by solid acids and bases, vol. 8, p. 107-156, Publisher Royal Society of Chemistry, Cambridge, UK, ISBN 978-0-85186-594-2, 1989.
[22]. Nishimura S., Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, 1st ed., Publisher New York: Wiley-Interscience, ISBN 978-0-471-39698-7, 2001.
[23]. Drahl C., Palladium's Hidden Talent, Chemical and Engineering News, vol. 86, p. 53-56, 2008.
Published
2018-09-15
How to Cite
1.
MUREŞAN AC. Ibuprofen: Original Versus Green Synthesis. The Annals of “Dunarea de Jos” University of Galati. Fascicle IX, Metallurgy and Materials Science [Internet]. 15Sep.2018 [cited 30Jun.2024];41(3):30-4. Available from: https://gup.ugal.ro/ugaljournals/index.php/mms/article/view/1757
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