Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation

Green Chemistry

Volumn 10, Issue 1, 2008, Pages 31-36

  Alfonsi, Kim ^a   Colberg, Juan ^b   Dunn, Peter J ^c   Fevig, Thomas ^b   Jennings, Sandra ^a   Johnson, Timothy A ^b   Kleine, H Peter ^b   Knight, Craig ^c   Nagy, Mark A ^b   Perry, David A ^b   Stefaniak, Mark ^c  

^a PFIZER INC   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37849039002     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b711717e     Document Type: Article

References (57)

1. P. Harremoës, The Precautionary Principle in the 20th Century: late lessons from early warnings, James & James/Earthscan, London, 2002, pp. 35–48.
2. J. H. Duffus and H. G. J. Worth, Fundamental Toxicology for Chemists, The Royal Society of Chemistry, London1996, p. vi.
3. Precaution, Environmental Science, and Preventive Public Policy, ed. J. Tickner, Island Press, Washington DC, 2002, p. 297.
4. Beyond the Molecular Frontier: Challenges for Chemistry and Chemical Engineering, National Academy Press, Washington DC, 2003, p. 181.
5. B. Trost Science 1991 254 1471-1477.
6. R. A. Sheldon Chem. and Ind. 1992 903-906.
7. Green Chemistry Theory and Practice, ed P. T. Anastas and J. C. Warner, Oxford University Press, Oxford, 1998.
8. A. D. Curzons D. C. Constable V. L. Cunningham Clean Prod. Process. 1999 1 82-90.
9. C. Jimenez-Gonzalez A. D. Curzons D. J. C. Constable V. L. Cunningham Clean Technol. Environ. Pol. 2005 7 42-50.
10. C. Capello U. Fischer K. Hungerbuhler Green Chem. 2007 9 917-934.
11. 50 figures) has the potential for acute and direct impact on the health and safety of our workforce.
12. Environmental and regulatory considerations were considered next. Regulatory considerations vary globally so this work incorporated both major EU and US classifications such as the EU risk phrases and the US hazardous air pollutant and toxic chemical lists. Solvents with ecotoxic properties such as those designated by the EU R50, R51 and R53 risk phrases, are difficult to treat in wastewater facilities or very expensive to dispose of. There is increased public attention to potential environmental impact of facility operations which is supported by publicly available polluter registers in some countries such as the Toxic Release Inventory in the United States. Some solvents with ozone depleting and photoreactive potential are getting more public and government attention as they are regularly discussed at profession forums and regulated under various country permitting or use restriction regulations. Solvents classified as very toxic and/or classified with CMR properties or as potentially environmentally difficult materials (e.g. with the potential for persistence and bioaccumulation) are subject to increasing regulatory attention. This may include, restricted or prohibited use and/or increased requirements increased requirements to control and report use. Certain regulated compounds such as US HAPs and chemicals subject to EU Integrated Pollution Prevention and Control (IPPC) can trigger expensive and technically challenging control requirements. In summary, the use and handling of such substances is monitored very tightly by the Environmental Protection Agencies worldwide.
13. The detailed information on these 39 solvents and a further 45 solvents are held in a more detailed Pfizer solvent selection tool, called the bundle book (solvents are classified into bundles). This more detailed tool is available to all Pfizer scientists through various internal websites.
14. D. J. C. Constable P. J. Dunn J. D. Hayler G. R. Humphrey J. Leazer, Jr. R. J. Linderman K. Lorenz J. Manley B. A. Pearlman A. Wells A. Zaks T. Y. Zhang Green Chem. 2007 9 411-420.
15. For a review covering the green and sustainable aspects of oxidation reactions see D. Lenoir Angew. Chem., Int. Ed. 2006 45 3206-3210.
16. For a review covering large-scale oxidations in the Pharmaceutical Industry see S. Caron R. W. Dugger S. Gut Ruggeri J. A. Ragan D. H. B. Ripin Chem. Rev. 2006 106 2943-2989.
17. D. B. Dess J. C. Martin J. Org. Chem. 1983 48 4155-4156.
18. S. V. Ley J. Norman W. P. Griffith S. P. Marsden Synthesis 1994 639-666.
19. A. J. Mancuso S.-L. Huang D. Swern J. Org. Chem. 1978 12 2480-2482.
20. A. J. Mancuso D. Swern Synthesis 1981 165-185.
21. M. R. Leanna T. J. Sowin H. E. Morton Tetrahedron Lett. 1992 33 5029-5032.
22. A. E. J. de Nooy A. C. Besemer H. van Bekkum Synthesis 1996 1153-1174.
23. A. Dijksman I. W. C. E. Arends R. A. Sheldon Chem. Commun. 2000 271-272.
24. A. Dijksman I. W. C. E. Arends R. A. Sheldon Synlett 2001 102-104.
25. R. A. Sheldon I. W. C. E. Arends G.-J. ten Brink A. Dijksman Acc. Chem. Res. 2002 35 774-781.
26. S. Grimaldi Speciality Chem. 2006 32-33.
27. For aerobic oxidations catalysed by copper reagents see I. E. Marko A. Gautier R. Dumeunier K. Doda F. Philippart S. M. Brown C. J. Urch Angew. Chem., Int. Ed. 2004 43 1588 and references therein. For aerobic oxidations by palladium reagents see.
28. G.-J. ten Brink I. W. C. E. Arends R. A. Sheldon Science, 2000 287 1636-1639.
29. S. S. Stahl Angew. Chem., Int. Ed. 2004 43 3400 and references therein. For aerobic oxidations catalysed by ruthenium reagents see.
30. B.-Z. Zhan M. A. White T.-K. Sham J. A. Pincock R. J. Doucet K. V. Ramano Rao K. N. Robertson T. S. Cameron J. Am. Chem. Soc. 2003 124 2195-2199 and references therein.
31. P. Gamez I. W. C. E. Arends J. Reedijk R. A. Sheldon Chem. Commun. 2003 2414-2415.
32. R. Liu C. Dong X. Liang X. Wang X. Hu J. Org. Chem. 2005 70 729-731. Note this reference also gives a very logical breakdown of the recent literature involving air oxidations of alcohols.
33. J. De Luca G. Giacomelli A. Porcheddu Org. Lett. 2001 3 3041-3043.
34. J. R. Parikh W. v. E. Doering J. Am. Chem. Soc. 1967 89 5505-5507.
35. F. Albericio M. Cases J. Alsina S. A. Triolo L. A. Carpino S. A. Yates Tetrahedron Lett. 1997 38 4853-4856.
36. R. Knorr A. Trzeciak W. Bannwarth D. Gillessen Tetrahedron Lett. 1989 30 1927-1930.
37. V. Dourtoglou J.-C. Ziegler B. Gross Tetrahedron Lett. 1978 15 1269-1272.
38. D. J. Dale, unpublished results.
39. B. Castro J. R. Dormoy G. Evin C. Selve Tetrahedron Lett. 1975 16 1219-1222.
40. W. Weng J. S. McMurray Tetrahedron Lett. 1999 40 2501-2504.
41. C. E. Garrett X. Jiang K. Prasad O. Repic Tetrahedron Lett 2002 43 4161-4165.
42. C. J. Barnett T. M. Wilson M. E. Kobierski Org. Process Res. Dev. 1999 3 184-188.
43. B. Belleau G. Malek J. Am. Chem. Soc. 1968 90 1651-1652.
44. N. Izumiya M. Muraoka J. Am. Chem. Soc. 1969 91 2391-2392.
45. For an example of the large scale use of PPACA see P. J. Dunn M. L. Hughes P. M. Searle A. S. Wood Org. Process Res. Dev. 2003 7 244-253.
46. For an example of the large scale use of EDCI see ref. 33 J. S. Carey D. Laffan C. Thomson M. T. Williams Org. Biomol. Chem. 2006 4 2337-2347.
47. P. J. Dunn S. Galvin K. Hettenbach Green Chem. 2004 6 43-48.
48. R. Vaidyanathan V. G. Kalthod N. P. Ngo J. M. Manley S. P. Lapekas J. Org. Chem. 2004 69 2565-2568.
49. K. Ishihara S. Ohara H. Yamamoto J. Org. Chem. 1996 61 4196-4197.
50. J. E. Anderson R. Davies R. N. Fitzgerald J. M. Haberman Synth. Commun. 2006 36 2129-2133.
51. P. Tang Org. Synth. 2005 81 262.
52. K. Arnold B. Davies R. L. Giles C. Grosjean G. E. Smith A. Whiting Adv. Synth. Catal. 2006 348 813-820.
53. V. Schellenberger H.-D. Jakubke Angew. Chem., Int. Ed. 1991 30 1437-1449.
54. For an example of the large scale use of iBuOCOCl see M. Prashad D. Har B. Hu H.-Y. Kim M. J. Girgis A. Chaudhary O. Repic T. J. Blacklock W. Marterer Org. Process Res. Dev. 2004 8 330-340.
55. For an example of the large scale use of thionyl chloride see S. Cai M. Dimitroff T. McKennon M. Reider L. Robarge D. Ryckman X. Shang J. Therrien Org. Process Res. Dev. 2004 8 353-359.
56. M. Allegretti R. Anacardio M. C. Cesta R. Curti M. Mantovanini G. Nano Org. Process Res. Dev. 2003 7 209-213.
57. For an example of the large scale use of oxalyl chloride see I. H. Smith A. Alorati G. Frampton S. Jones J. O’Rourke M. W. Woods Org. Process Res. Dev. 2003 7 1034-1039.