Green chemistry ibuprofen

Devise a synthesis of 5-Ibuprofen that, in terms of the principles of green chemistry, compares favourably with the commercial route outlined in Chapter 2. 

Lastly, Cann featured Colin Baird s Environmental Chemistry as an example of a text that has green chemistry integrated throughout every chapter. In addition, the preface is an introduction to green chemistry, atom economy, and the synthesis of ibuprofen. 

In 1992 BHC (Boots Hoechst-Celanese) Company commercialized a new synthetic process to manufacture ibuprofen in BHC s 3500 metric-ton-per-year facility in Bishop/TX, USA, which was cited as an industry model of environmental excellence in chemical processing technology. For its innovation, BHC was the recipient of the 1997 Alternative Synthetic Pathways Award of the Presidential Green Chemistry Challenge. 

In 1992, BASF opened a 35 000 tons per year ibuprofen production plant in Bishop, Texas. This plant was the result of the elegant green chemistry route developed by the BHC consortium. The clean synthesis of ibuprofen is an excellent example of how combining catalysis and green chemistry can yield both commercial success and environmental benefits. Ibuprofen is a nonsteroidal, anti-inflammatory painkiller. It is a popular over-the-counter drug against headache, toothache, and muscular pains. You may know it better as Advil , Motrin , or Nurofen. 

Green chemistry reduces toxicity, minimizes waste, saves energy, and cuts down on the depletion of natural resources. It allows for advances in chemistry to occur in a much more environmentally benign way. In the future, when green chemistry is practiced by all chemists and all chemical-related companies, the term green chemistry will ideally disappear as all chemistry becomes green, see also Ibuprofen Industrial Chemistry, Organic Solution Chemistry. 

The most frequently discussed green chemistry topic was catalysts, followed by the synthesis of ibuprofen, ionic liquids, supercritical solvents, atom economy, pesticides, polymers, renewable feedstocks, and the principles of green chemistry. Other green chemistry topics that were found included... 

In 1997, the Presidential Green Chemistry Challenge Greener Synthetic PathwaysAward was given to BHC Company (now BASF) for a novel method of ibuprofen synthesis.The new process consists of three catalytic steps, with the only byproduct being acetic acid, and has overall atom efficiency of about 80%. Since the acetic acid byproduct does not end up in the waste but is recovered, the process can be considered virtually 99% atom efficient. The older process, replaced by the award-winning one, consisted of six stoichiometric steps with an overall atom efficiency of less than 40%. 

The industrial synthesis of ibuprofen is a well-known case study for green chemistry . [190] The original Boots route, starting from benzene, comprised seven steps, p-lsobutylacetophenone is accessible by alkylation of benzene with isobutene, followed by a Friedel-Crafts acylation with acetic chloride. Homologation to the corresponding aryl-propionaldehyde is achieved by a Darzens reaction. Transformations via the oxime and nitrile, and hydrolysis of the latter, finally give ibuprofen. 

RSC Ibuprofen - A Case Study in Green Chemistry in http //www.rsc.org/ Education/Teachers/Resources/green/ibuprofen/ibuprofen.pdf. 

On page 299, A Word About... Green Chemistry and Ibuprofen A Case Study showed how efficiently ibuprofen can be prepared on a large scale. Another nonsteroidal, anti-inflammatory drug (NSAID) is acetaminophen. Suggest a short synthesis of acetaminophen from p-hydroxyaniline. 

Although relevant applications of organic chemistry are stressed throughout the text, short sections under the general rubric A Word About... emphasize applications to other branches of science and to human life. These sections, which have been a popular feature, appear at appropriate places within the text rather than as isolated essays. They stand out from the text so that instructors can easily refer to these sections, as desired. There are forty-one of these essays on topics ranging from polycyclic aromatic hydrocarbons and cancer to ether and anesthesia, water treatment and the chemistry of enols and enolates, green chemistry and ibuprofen, sweetness and sweeteners, and DNA and crime. 

To illustrate the benefits of atom economy, consider the synthesis of ibuprofen, mentioned earlier, which won the Presidential Green Chemistry Challenge Award in 1997. In the former process, developed in the 1960s, only 40% of the reactant atoms were incorporated into the desired ibuprofen product the remaining 60% of the reactant atoms found their way into unwanted by-products or wastes that required disposal. The new method requires fewer reaction steps and recovers 77% of the reactant atoms in the desired product. This "green" process eliminates millions of pounds of waste chemical by-products every year, and it reduces by millions of pounds the amount of reactants needed to prepare this widely used analgesic. 

The new synthetic route to ibuprofen is an important example of how ideas of green chemistry can influence for the better the industrial synthetic methods used, not only from the point of view of economic efficiency, but also by introducing more effective methods of science and technology. Improved methods of synthesis for hexan-l,6-dioic acid (adipic aid) and cis-butenediol acid (maleic anhydride) - important for the industrial synthesis of nylon and polyesters respectively - are two other examples of the impact of a greener synthetic approach to industrial chemistry. 

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