A database tool for process chemists and chemical engineers to gauge the material and synthetic efficiencies of synthesis plans to industrially important targets

Pure and Applied Chemistry

Volumn 83, Issue 7, 2011, Pages 1361-1378

  Andraos, John ^a  

^a CareerChem   (Canada)

Author keywords

Agrichemicals; Atom economy; Dyestuffs; E factor; Flavorings; Fragrances; Green metrics; Optimization; Pharmaceuticals; Sweeteners; Synthesis strategy

Indexed keywords

AGRICHEMICALS; ATOM ECONOMY; DYESTUFFS; E-FACTOR; FLAVORINGS; GREEN METRICS; SWEETENERS; SYNTHESIS STRATEGY;

AGRICULTURAL CHEMICALS; CHEMICAL INDUSTRY; CHEMISTRY; DATABASE SYSTEMS; DECISION MAKING; FOOD ADDITIVES; INDICATORS (CHEMICAL); INDUSTRIAL CHEMICALS; ODORS; OPTIMIZATION;

SYNTHESIS (CHEMICAL);

EID: 79959744030     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-10-10-07     Document Type: Article

References (40)

1. B. M. Trost. Science 254, 1471 (1991).
2. R. A. Sheldon. Chem. Tech. 24, 38 (1994).
3. A. Lavoisier. Mèmoires de l'Académie Royale des Sciences, p. 520 (1775).
4. For references to unified green metrics, see:, J. Andraos. Org. Process Res. Dev. 9, 149 (2005)
5. J. Andraos. Org. Process Res. Dev. 9, 404 (2005)
6. J. Andraos, J. Izhakova. Chim. Oggi Chem. Today 24, Suppl., 31 (2006)
7. J. Andraos. Canadian Chem. News 59, 14 (2007).
8. For reviews of green metrics, see:, F. G. Calvo-Flores. ChemSusChem 2, 905 (2009)
9. J. Andraos. In Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes, A. Lapkin, D. C. Constable (Eds.), pp. 69-199, Blackwell Scientific, Oxford (2008).
10. J. Andraos, M. Sayed. J. Chem. Educ. 84, 1004 (2007).
11. J. Andraos. Org. Process Res. Dev. 10, 212 (2006).
12. J. Andraos. Org. Process Res. Dev. 13, 161 (2009).
13. J. Andraos. The Algebra of Organic Synthesis: Green Metrics, Design Strategy, Route Selection, and Optimization, CRC Press, Boca Raton (2011).
14. D. J. Rogers, T. T. Tanimoto. Science 132, 1115 (1960).
15. C. Graebe, C. Liebermann. Chem. Ber. 2, 332 (1869).
16. O. Illa, M. Arshad, A. Ros, E. M. McGarrigle, V. K. Aggarwal. J. Am. Chem. Soc. 132, 1828 (2010).
17. L. T. Sandborn. Org. Synth. Coll. Vol. 1, 340 (1941).
18. S. V. Ley, A. Abad-Somovilla, J. C. Anderson, C. Ayats, R. Bänteli, E. Beckmann, A. Boyer, M. G. Brasca, A. Brice, H. B. Broughton, B. J. Burke, E. Cleator, D. Craig, A. A. Denholm, R. M. Denton, T. Durand-Reville, L. B. Gobbi, M. Göbel, B. L. Gray, R. B. Grossmann, C. E. Gutteridge, N. Hahn, S. L. Harding, D. C. Jennens, L. Jennens, P. J. Lovell, H. J. Lovell, M. L. de la Puente, H. C. Kolb, W. J. Koot, S. L. Maslen, C. F. McCusker, A. Mattes, A. R. Pape, A. Pinto, D. Santafianos, J. S. Scott, S. C. Smith, A. Q. Somers, C. D. Spilling, F. Stelzer, P. L. Toogood, R. M. Turner, G. E. Veitch, A. Wood, C. Zumbrunn. Chem.-Eur. J. 14, 10683 (2008).
19. G. E. Veitch, A. Boyer, S. V. Ley. Angew. Chem., Int. Ed. 47, 9402 (2008).
20. A. Muheim, B. Müller, T. Münch, M. Wetli. EP885968, Filed 12 June 1998, Issued 23 December 1998.
21. A. Muheim, K. Lerch. Appl. Microbiol. Biotechnol. 51, 456 (1999).
22. R. Willstätter. Chem. Ber. 34, 129 (1901).
23. R. Willstätter. Chem. Ber. 34, 3163 (1901).
24. N. Gommermann, P. Knochel. Org. Synth. 84, 1 (2007).
25. For synthesis plans to (-)-menthol by Takasago, see:, H. Takaya, S. Akutagawa, R. Noyori. Org. Synth. 67, 20 (1989)
26. K. Tani, T. Yamagata, S. Otsuka, H. Kumobayashi, S. Akutagawa. Org. Synth. 67, 33 (1989)
27. S. Akutagawa. Top. Catal. 4, 271 (1997)
28. K. Takabe, T. Katagiri, J. Tanaka, T. Fujita, S. Watanabe, K. Suga. Org. Synth. 67, 44 (1989)
29. Y. Nakatani, K. Kawashima. Synlett 147 (1978)
30. N. Ravasio, N. Poli, R. Psaro, M. Saba, F. Zaccheria. Top. Catal. 13, 195 (2000).
31. G. P. Taber, D. M. Pfisterer, J. C. Colberg. Org. Process Res. Dev. 8, 385 (2004).
32. The Presidential Green Chemistry Challenge Award Recipients 1996-2009, June 2009, 744K09002, U.S. Environmental Protection Agency, p. 78 (http://www.epa.gov).
33. For other synthesis plans to (+)-sertraline hydrochloride, see:, W. M. Welch, A. R. Kraska, R. Sarges, B. K. Koe. J. Med. Chem. 27, 1508 (1984)
34. G. J. Quallich, M. T. Williams, R. C. Friedmann. J. Org. Chem. 55, 4971 (1999)
35. K. Vukics, T. Fodor, J. Fischer, L. Fellegvári, S. Lévai. Org. Process Res. Dev. 6, 82 (2002)
36. G. Wang, C. Zheng, G. Zhao. Tetrahedron: Asymmetry 17, 2074 (2006)
37. M. Lautens, T. Rovis. Tetrahedron 55, 8967 (1999)
38. C. Dockendorff, S. Sahli, M. Olsen, L. Milhau, M. Lautens. J. Am. Chem. Soc. 127, 15028 (2005)
39. J. Yun, S. L. Buchwald. J. Org. Chem. 65, 767 (2000)
40. P. Krumlinde, K. Bogar, J. E. Bäckvall. Chem.-Eur. J. 16, 4031 (2010).