Experimental Limiting Oxygen Concentrations for Nine Organic Solvents at Temperatures and Pressures Relevant to Aerobic Oxidations in the Pharmaceutical Industry

Organic Process Research and Development

Volumn 19, Issue 11, 2015, Pages 1537-1543

  Osterberg, Paul M ^a   Niemeier, Jeffry K ^b   Welch, Christopher J ^c   Hawkins, Joel M ^d   Martinelli, Joseph R ^b   Johnson, Thomas E ^a   Root, Thatcher W ^e   Stahl, Shannon S ^f  

^a Fauske and Associates LLC   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

^d PFIZER INC   (United States)

^e Wisconsin Electric Machines and Power Electronics Consortium   (United States)

^f UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFOXIDE; MIXTURES; OXYGEN; SOLVENTS;

2-METHYLTETRAHYDROFURAN; ELEVATED TEMPERATURE; FLAMMABLE ATMOSPHERE; LIMITING OXYGEN CONCENTRATIONS; PARTIAL PRESSURE OF OXYGEN; PHARMACEUTICAL INDUSTRY; PHARMACEUTICAL MANUFACTURING; SAFE OPERATING CONDITIONS;

ORGANIC SOLVENTS;

EID: 84947930098     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op500328f     Document Type: Article

References (37)

1. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411-420
2. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347
3. Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Chem. Rev. 2006, 106, 2943-2989
4. Cavani, F.; Teles, J. H. ChemSusChem 2009, 2, 508-534
5. LaPorte, T. L.; Hamedi, M.; DePue, J. S.; Shen, L. F.; Watson, D.; Hsieh, D. Org. Process Res. Dev. 2008, 12, 956-966
6. Witt, A.; Teodorovic, P.; Linderberg, M.; Johansson, P.; Minidis, A. Org. Process Res. Dev. 2013, 17, 672-678
7. Bowman, R. K.; Brown, A. D.; Cobb, J. H.; Eaddy, J. F.; Hatcher, M. A.; Leivers, M. R.; Miller, J. F.; Mitchell, M. B.; Patterson, D. E.; Toczko, M. A.; Xie, S. J. Org. Chem. 2013, 78, 11680-11690
8. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
9. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2363
10. Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854-3867
11. Shi, Z. Z.; Zhang, C.; Tang, C. H.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381-3430
12. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851-863
13. The University of Wisconsin-Madison Oxidation Consortium (MadOx) was formed in April 2012 with member companies Eli Lilly and Co., Pfizer, and Merck.
14. Lauber, M. B.; Stahl, S. S. ACS Catal. 2013, 3, 2612-2616
15. Greene, J. F.; Hoover, J. M.; Mannel, D. S.; Root, T. W.; Stahl, S. S. Org. Process Res. Dev. 2013, 17, 1247-1251
16. Steves, J. E.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 15742-15745
17. Kim, J.; Stahl, S. S. ACS Catal. 2013, 3, 1652-1656
18. Also see: Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901-16910
19. Early collaborative efforts focused on the development of continuous-flow methods suitable for scalable application of aerobic oxidation. See: Ye, X.; Johnson, M. D.; Diao, T.; Yates, M. H.; Stahl, S. S. Green Chem. 2010, 12, 1180-1186
20. Kubota, H.; Umekawa, A.; Tanaka, Y.; Makita, T. Anzen Kogaku 1979, 18, 264-270
21. Lewis, B.; von Elbe, G. Combustion, Flames and Explosions of Gases, 3 rd ed.; Academic Press: New York, 1987; p 339.
22. Brooks, M. R.; Crowl, D. A. J. Loss Prev. Process Ind. 2007, 20, 144-150
23. Zabetakis, M. G. Flammability Characteristics of Combustible Gases and Vapors; Bulletin 627, Bureau of Mines, NTIS AD701576; U.S. Department of the Interior: Washington, DC, 1965.
24. For an assessment of flammability hazards and safety considerations for biocatalytic aerobic oxidations that employ mixed organic/aqueous solvents, see: Schmid, A.; Kollmer, A.; Sonnleitner, B.; Witholt, B. Bioprocess Eng. 1999, 20, 91-100
25. ASTM E2079 Standard Test Methods for Limiting Oxygen (Oxidant) Concentration in Gases and Vapors; American Society for Testing and Materials: Philadelphia, PA, 2013.
26. Mashuga, C. V. Determination of the Combustion Behavior for Pure Components and Mixtures Using a 20-Liter Sphere. Ph.D. Thesis, Michigan Technological University, Houghton, MI, April 1999.
27. Zlochower, I. A.; Green, G. M. J. Loss Prev. Process Ind. 2009, 22, 499-505
28. Britton, L. G. Process Saf. Prog. 2002, 21, 31-54
29. Rowley, R. L.; Wilding, W. V.; Knotts, T. A., IV; Giles, N. DIPPR Data Compilation of Pure Chemical Properties; Design Institute for Physical Properties/AIChE: New York, 2013.
30. Babrauskas, V. Ignition Handbook; Fire Science Publishers, Society of Fire Protection Engineers: Issaquah, WA, 2003.
31. Mashuga, C. V.; Crowl, D. A. Process Saf. Prog. 1999, 18, 127-134
32. Gordon, S.; McBride, B. J. Computer Program for Calculation of Complex Chemical Equilibrium Compositions and Applications; NASA Reference Publication 1311, 1996.
33. Razus, D.; Molnarne, M.; Fuß, O. Chem. Eng. Process. 2004, 43, 775-784
34. Bane, S. Spark Ignition: Experimental and Numerical Investigation with Application to Aviation Safety. Ph.D. Thesis, California Institute of Technology, Pasadena, CA, May 2010.
35. Eckhoff, R. K.; Ngo, M.; Olsen, W. J. Hazard. Mater. 2010, 175, 293-297
36. NFPA 69: Standard on Explosion Prevention Systems; National Fire Protection Association: Quincy, MA, 2014.
37. Kelly, R. J. Chem. Health Saf. 1996, (Sept/Oct), 26-36.