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Green Chemistry and Associated Metrics

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Green Chemistry Metrics

Part of the book series: SpringerBriefs in Molecular Science ((GREENCHEMIST))

Abstract

This chapter provides an overview of green metrics and their historical role in promoting the development of green chemistry. Starting with the history of the field, the Twelve Principles of Green Chemistry are introduced and discussed in conjunction with a “green-by-design” approach recently applied to the synthesis of Lipitor®. Various perspectives on synthetic efficiency are briefly outlined with reference to atom economy and E factor. These ideas are further explored in the context of three industrial processes which have received Presidential Green Chemistry Challenge Awards. The synthesis of ibuprofen is examined from the point of view of intrinsic efficiency. Using the BHC process as an example, several benefits associated with the use of catalysis are discussed, with an emphasis placed on designing atom-efficient reactions. A global perspective centered around the production of chemical waste is also outlined with reference to Merck’s commercial synthesis of Januvia®, a medication for the treatment of type II diabetes. Finally, Pfizer’s new sertraline process is used to describe ways of improving both quantitative as well as qualitative aspects of an industrial synthesis. The chapter concludes with a brief outline of the future directions of green metrics.

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References

  1. Office of pollution prevention and toxics, EPA (2002) Green chemistry program fact sheet. http://nepis.epa.gov/Exe/ZyPDF.cgi/P1004H5E.PDF?Dockey=P1004H5E.PDF. Accessed 28 Apr 2014

  2. Trost BM (1991) The atom economy—a search for synthetic efficiency. Science 254:1471–1477. doi:10.1126/science.1962206

    Article  CAS  Google Scholar 

  3. Sheldon RA (1992) Organic synthesis—past, present and future. Chem Ind 903–906

    Google Scholar 

  4. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford 29

    Google Scholar 

  5. Lancaster M (2010) Green chemistry: an introductory text, 2nd edn. RSC Paperbacks, Cambridge

    Google Scholar 

  6. Sheldon RA, Arends IWCE, Hanefeld U (2007) Green chemistry and catalysis. Wiley-VCH Verlag, Weinheim

    Book  Google Scholar 

  7. Anastas P (2010–2012) Handbook of green chemistry vol 1–9. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Google Scholar 

  8. Dicks AP (2012) Green organic chemistry in lecture and laboratory. CRC Press, Taylor and Francis Group, Boca Raton

    Google Scholar 

  9. Andraos J (2012) The algebra of organic synthesis: green metrics. CRC Press, Taylor and Francis Group, Boca Raton

    Google Scholar 

  10. Dicks AP, Batey RA (2013) ConfChem conference on educating the next generation: green and sustainable chemistry—greening the organic curriculum: development of an undergraduate catalytic chemistry course. J Chem Educ 90:519–520. doi:10.1021/ed2004998

    Article  CAS  Google Scholar 

  11. Anastas PT, Warner JC (2000) Green chemistry: theory and practice. Oxford University Press, Oxford, pp 29–55

    Google Scholar 

  12. Ma SK, Gruber J, Davis C, Newman L, Gray D, Wang A, Grate J, Huisman GW, Sheldon RA (2010) A green-by-design biocatalytic process for atorvastatin intermediate. Green Chem 12:81–86. doi:10.1039/B919115C

    Article  CAS  Google Scholar 

  13. Quarterly U.S. sales data for Lipitor. http://www.drugs.com/stats/lipitor. Accessed 1 May 2014

  14. Winterton N (2001) Twelve more green chemistry principles. Green Chem 3:G73–G75. doi:10.1039/B110187K

    Article  Google Scholar 

  15. Anastas PT, Zimmerman JB (2003) Design through the 12 principles of green engineering. Environ Sci Technol 37:94A–101A. doi:10.1021/es032373g

    Article  Google Scholar 

  16. Tang SLY, Smith RL, Poliakoff M (2005) Principles of green chemistry: PRODUCTIVELY. Green Chem 7:761–762. doi:10.1039/B513020B

    Article  Google Scholar 

  17. Tang S, Bourne R, Smith R, Poliakoff M (2008) The 24 principles of green engineering and green chemistry: “IMPROVEMENTS PRODUCTIVELY”. Green Chem 10:268–269. doi:10.1039/B719469M

    Article  CAS  Google Scholar 

  18. Anastas PT, Kirchoff MM (2002) Origins, current status, and future challenges of green chemistry. Acc Chem Res 35:686–694. doi:10.1021/ar010065m

    Article  CAS  Google Scholar 

  19. Beach ES, Cui Z, Anastas PT (2009) Green chemistry: a design framework for sustainability. Energy Environ Sci 2:1038–1049. doi:10.1039/b904997p

    Article  CAS  Google Scholar 

  20. Anastas P, Eghbali N (2010) Green chemistry: principles and practice. Chem Soc Rev 39:301–312. doi:10.1039/b918763b

    Article  CAS  Google Scholar 

  21. Mulvihill MJ, Beach ES, Zimmerman JB, Anastas PT (2011) Green chemistry and green engineering: a framework for sustainable technology development. Annu Rev Environ 36:271–293. doi:10.1146/annurev-environ-032009-095500

    Article  Google Scholar 

  22. Bourne RA, Poliakoff M (2011) Green chemistry: what is the way forward? Mendeleev Commun 21:235–238. doi:10.1016/j.mencom.2011.09.001

    Article  CAS  Google Scholar 

  23. Horvath IT, Anastas PT (2007) Innovations and green chemistry. Chem Rev 107:2169–2173. doi:10.1021/cr078380v

    Article  CAS  Google Scholar 

  24. Dichiarante V, Ravelli D, Albini A (2010) Green chemistry: state of the art through an analysis of the literature. Green Chem Lett Rev 3:105–113. doi:10.1080/17518250903583698

    Article  CAS  Google Scholar 

  25. Sheldon RA (2008) E factors, green chemistry and catalysis: an odyssey. Chem Commun 29:3352–3365. doi:10.1039/b803584a

    Article  Google Scholar 

  26. Constable DJC, Curzons AD, Cunningham VL (2002) Metrics to “green” chemistry—which are the best? Green Chem 4:521–527. doi:10.1039/b206169b

    Article  CAS  Google Scholar 

  27. Constable DJC, Jimenez-Gonzalez C, Henderson RK (2007) Perspective on solvent use in the pharmaceutical industry. Org Process Res Dev 11:133–137. doi:10.1021/op060170h

    Article  CAS  Google Scholar 

  28. Andraos J (2005) Unification of reaction metrics for green chemistry: applications to reaction analysis. Org Process Res Dev 9:149–163. doi:10.1021/op049803n

    Article  CAS  Google Scholar 

  29. Information about the Presidential Green Chemistry Challenge. http://www2.epa.gov/green-chemistry/information-about-presidential-green-chemistry-challenge. Accessed 2 May 2014

  30. Cann MC (1999) Bringing state-of-the-art, applied, novel, green chemistry to the classroom by employing the Presidential Green Chemistry Challenge Awards. J Chem Educ 76:1639–1641. doi:10.1021/ed076p1639

    Article  CAS  Google Scholar 

  31. 2006 greener reaction conditions award. http://www2.epa.gov/green-chemistry/2006-greener-reaction-conditions-award. Accessed 1 May 2014

  32. Elango V, Murphy MA, Smith BL, Davenport KG, Mott GN, Zey EG, Moss GL (1991) U.S. Patent 4981995; Lindley DD, Curtis TA, Ryan TR, de la Garza EM, Hilton CB, Kenesson TM (1991) U.S. Patent 5068448

    Google Scholar 

  33. Stuart NJ, Sanders AS (1968) U.S. Patent 3385886

    Google Scholar 

  34. Rainsford KD (2012) Ibuprofen: pharmacology, therapeutics and side effects. Springer, Basel

    Google Scholar 

  35. Drug record: ibuprofen. http://livertox.nlm.nih.gov/Ibuprofen.htm. Accessed 2 May 2014

  36. Cann MC, Connelly ME (2000) Real world cases in green chemistry. ACS, Washington, DC 19–24

    Google Scholar 

  37. Green chemistry—the atom economy, student manual. Royal Society of Chemistry http://www.rsc.org/images/PDF1_tcm18-40521.pdf. Accessed 2 Feb 2014

  38. Wang Z (2009) Comprehensive organic name reactions and reagents. Wiley, Hoboken, pp 841–845

    Google Scholar 

  39. Cann MC, Dickneider TA (2004) Infusing the chemistry curriculum with green chemistry using real-world examples, web modules, and atom economy in organic chemistry courses. J Chem Educ 81:977–980. doi:10.1021/ed081p977

    Article  CAS  Google Scholar 

  40. Doble M, Kruthiventi AK (2007) Green chemistry and engineering. Academic Press, Elsevier Science and Technology Books

    Google Scholar 

  41. Desai AA (2011) Sitagliptin manufacture: a compelling tale of green chemistry, process intensification, and industrial asymmetric catalysis. Angew Chem Int Ed 50:1974–1976. doi:10.1002/anie.201007051

    Article  CAS  Google Scholar 

  42. Kim D, Wang L, Beconi M, Eiermann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio F, McCann ME, Patel RA, Petrov A, Scapin G, Patel SB, Roy RS, Wu JK, Wyvratt MJ, Zhang BB, Zhu L, Thornberry NA, Weber AE (2005) (2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1, 2, 4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem 48:141–151. doi:10.1021/jm0493156

    Article  CAS  Google Scholar 

  43. Hansen KB, Balsells J, Dreher S, Hsiao Y, Kubryk M, Palucki M, Rivera N, Steinhuebel D, Armstrong JD III, Askin D, Grabowski EJJ (2005) First generation process for the preparation of the DPP-IV inhibitor sitagliptin. Org Process Res Dev 9:634–639. doi:10.1021/op0500786

    Article  CAS  Google Scholar 

  44. Hansen KB, Hsiao Y, Xu F, Rivera N, Clausen A, Kubryk M, Krska S, Rosner T, Simmons B, Balsells J, Ikemoto N, Sun Y, Spindler F, Malan C, Grabowski EJJ, Armstrong JD III (2009) Highly efficient asymmetric synthesis of sitagliptin. J Am Chem Soc 131:8798–8804. doi:10.1021/ja902462q

    Article  CAS  Google Scholar 

  45. Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ (2010) Biocatalytic asymmetric synthesis of chiral amines from ketones. Science 329:305–309. doi:10.1126/science.1188934

    Article  CAS  Google Scholar 

  46. Balsells J, Hsiao Y, Hansen KB, Xu F, Ikemoto N, Clasuen A, Armstrong JD III (2010) Synthesis of sitagliptin, the active ingredient in Januvia® and Janumet®. In: Dunn PJ, Wells AS, Williams MT (eds) Green chemistry in the pharmaceutical industry. Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim

    Google Scholar 

  47. Dunn PJ (2012) The importance of green chemistry in process research and development. Chem Soc Rev 41:1452–1461. doi:10.1039/c1cs15041c

    Article  CAS  Google Scholar 

  48. 2006 greener synthetic pathways award. http://www2.epa.gov/green-chemistry/2006-greener-synthetic-pathways-award. Accessed 3 May 2014

  49. 2010 greener reaction conditions award. http://www2.epa.gov/green-chemistry/2010-greener-reaction-conditions-award. Accessed 3 May 2014

  50. Prat D, Pardigon O, Flemming H-W, Letestu S, Ducandas V, Isnard P, Guntrum E, Senac T, Ruisseau S, Cruciani P, Hosek P (2013) Sanofi’s solvent selection guide: a step toward more sustainable processes. Org Process Res Dev 17:1517–1525. doi:10.1021/op4002565

    Article  CAS  Google Scholar 

  51. Boethling R, Voutchkova A (2012) Handbook of green chemistry volume 9: designing safer chemicals, 1st edn. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Google Scholar 

  52. Van Aken K, Strekowski L, Patiny L (2006) EcoScale, a semi-quantitative tool to select an organic preparation based on economical and ecological parameters. Beilstein J Org Chem 2. doi:10.1186/1860-5397-2-3

  53. Taber GP, Pfisterer DM, Colberg JC (2004) A new and simplified process for preparing N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine and a telescoped process for the synthesis of (1S-cis)-4-(3,4-dichlorophenol)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate: key intermediates in the synthesis of sertraline hydrochloride. Org Process Res Dev 8:385–388. doi:10.1021/op0341465

    Article  CAS  Google Scholar 

  54. Sarges R, Tretter JR, Tenen SS, Weissman A (1973) 5,8-disubstituted 1-aminotetralins. A class of compounds with a novel profile of central nervous system activity. J Med Chem 16:1003–1011. doi:10.1021/jm00267a010

    Article  CAS  Google Scholar 

  55. Welch WM (1995) Discovery and preclinical development of the serotonin reuptake inhibitor sertraline. Adv Med Chem 3:113–148. doi:10.1016/S1067-5698(06)80005-2

    Article  CAS  Google Scholar 

  56. Welch WM, Kraska AR, Sarges R, Koe BK (1984) Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. J Med Chem 27:1508–1515. doi:10.1021/jm00377a021

    Article  CAS  Google Scholar 

  57. Cann MC, Umile TP (2008) Real world cases in green chemistry, vol II. ACS, Washington, DC, pp 39–45

    Google Scholar 

  58. 2002 greener synthetic pathways award. http://www2.epa.gov/green-chemistry/2002-greener-synthetic-pathways-award. Accessed 3 May 2014

  59. Alfonsi K, Colberg J, Dunn PJ, Fevig T, Jennings S, Johnson TA, Kleine HP, Knight C, Nagy MA, Perry DA, Stefaniak M (2008) Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation. Green Chem 10:31–36. doi:10.1039/b711717e

    Article  CAS  Google Scholar 

  60. Henderson RK, Jimenez-Gonzalez C, Constable DJC, Alston SR, Inglis GGA, Fisher G, Sherwood J, Binks SP, Curzons AD (2011) Expanding GSK’s solvent selection guide—embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem 13:854–862. doi:10.1039/c0gc00918k

    Article  CAS  Google Scholar 

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Dicks, A.P., Hent, A. (2015). Green Chemistry and Associated Metrics. In: Green Chemistry Metrics. SpringerBriefs in Molecular Science(). Springer, Cham. https://doi.org/10.1007/978-3-319-10500-0_1

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