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

Osterberg, Paul M.; Niemeier, Jeffry K.; Welch, Christopher J.; Hawkins, Joel M.; Martinelli, Joseph R.; Johnson, Thomas E.; Root, Thatcher W.; Stahl, Shannon S.

doi:10.1021/op500328f

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

Journal Article · Tue Dec 23 00:00:00 EST 2014 · Organic Process Research & Development

DOI:https://doi.org/10.1021/op500328f· OSTI ID:1179621

Osterberg, Paul M. ^[1]; Niemeier, Jeffry K. ^[2]; Welch, Christopher J. ^[3]; Hawkins, Joel M. ^[4]; Martinelli, Joseph R. ^[2]; Johnson, Thomas E. ^[1]; Root, Thatcher W. ^[5]; Stahl, Shannon S. ^[6]

Fauske & Associates, Burr Ridge, Illinois 60527, United States
Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, United States
Merck Research Laboratories, Rahway, New Jersey 07065, United States
Pfizer Worldwide Research and Development, Groton, Connecticut 06340, United States
Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States

Applications of aerobic oxidation methods in pharmaceutical manufacturing are limited in part because mixtures of oxygen gas and organic solvents often create the potential for a flammable atmosphere. To address this issue, limiting oxygen concentration (LOC) values, which define the minimum partial pressure of oxygen that supports a combustible mixture, have been measured for nine commonly used organic solvents at elevated temperatures and pressures. The solvents include acetic acid, N-methylpyrrolidone, dimethyl sulfoxide, tert-amyl alcohol, ethyl acetate, 2-methyltetrahydrofuran, methanol, acetonitrile, and toluene. Furthermore, the data obtained from these studies help define safe operating conditions for the use of oxygen with organic solvents.

View Journal Article

Cite

Export

Save

Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-05ER15690

OSTI ID:: 1179621

Alternate ID(s):: OSTI ID: 1346922

Journal Information:: Organic Process Research & Development, Journal Name: Organic Process Research & Development Vol. 19 Journal Issue: 11; ISSN 1083-6160

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 144 works

Citation information provided by
Web of Science

References (26)

Overcoming the “Oxidant Problem”: Strategies to Use O ₂ as the Oxidant in Organometallic C–H Oxidation Reactions Catalyzed by Pd (and Cu) Campbell, Alison N.; Stahl, Shannon S. Accounts of Chemical Research, Vol. 45, Issue 6 https://doi.org/10.1021/ar2002045	journal	January 2012
Efficient Aerobic Oxidation of Secondary Alcohols at Ambient Temperature with an ABNO/NO _x Catalyst System Lauber, Markus B.; Stahl, Shannon S. ACS Catalysis, Vol. 3, Issue 11 https://doi.org/10.1021/cs400746m	journal	October 2013
Cu/Nitroxyl-Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature Kim, Jinho; Stahl, Shannon S. ACS Catalysis, Vol. 3, Issue 7 https://doi.org/10.1021/cs400360e	journal	June 2013
Limiting oxygen concentration evaluation in flammable gaseous mixtures by means of calculated adiabatic flame temperatures Razus, Domnina; Molnarne, Maria; Fuß, Oliver Chemical Engineering and Processing: Process Intensification, Vol. 43, Issue 6 https://doi.org/10.1016/S0255-2701(03)00078-3	journal	June 2004
Development of equipment and procedures for the safe operation of aerobic bacterial bioprocesses in the presence of bulk amounts of flammable organic solvents Schmid, A.; Kollmer, A.; Sonnleitner, B. Bioprocess Engineering, Vol. 20, Issue 2 https://doi.org/10.1007/s004490050565	journal	January 1999
Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen-Coupled Turnover Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 43, Issue 26 https://doi.org/10.1002/anie.200300630	journal	June 2004
Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant Gligorich, Keith M.; Sigman, Matthew S. Chemical Communications, Issue 26 https://doi.org/10.1039/b902868d	journal	January 2009
Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols Hoover, Jessica M.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 133, Issue 42 https://doi.org/10.1021/ja206230h	journal	October 2011
Analysis of the reactions used for the preparation of drug candidate molecules Carey, John S.; Laffan, David; Thomson, Colin Organic & Biomolecular Chemistry, Vol. 4, Issue 12 https://doi.org/10.1039/b602413k	journal	January 2006
The limiting oxygen concentration and flammability limits of gases and gas mixtures Zlochower, Isaac A.; Green, Gregory M. Journal of Loss Prevention in the Process Industries, Vol. 22, Issue 4 https://doi.org/10.1016/j.jlp.2009.03.006	journal	July 2009
Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems Steves, Janelle E.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 42 https://doi.org/10.1021/ja409241h	journal	October 2013
A Novel Scalable Process to the GSK3β Inhibitor AZD8926 Based on a Heterocyclic Ziegler Coupling Witt, Anette; Teodorovic, Peter; Linderberg, Mats Organic Process Research & Development, Vol. 17, Issue 4 https://doi.org/10.1021/op300365e	journal	March 2013
Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst Greene, Jodie F.; Hoover, Jessica M.; Mannel, David S. Organic Process Research & Development, Vol. 17, Issue 10 https://doi.org/10.1021/op400207f	journal	July 2013
Sustainability in Catalytic Oxidation: An Alternative Approach or a Structural Evolution? Cavani, Fabrizio; Teles, Joaquim Henrique ChemSusChem, Vol. 2, Issue 6 https://doi.org/10.1002/cssc.200900020	journal	June 2009
Using heats of oxidation to evaluate flammability hazards Britton, Laurence G. Process Safety Progress, Vol. 21, Issue 1 https://doi.org/10.1002/prs.680210108	journal	March 2002
Key green chemistry research areas—a perspective from pharmaceutical manufacturers Constable, David J. C.; Dunn, Peter J.; Hayler, John D. Green Chem., Vol. 9, Issue 5 https://doi.org/10.1039/B703488C	journal	January 2007
Synthesis of HCV Replicase Inhibitors: Base-Catalyzed Synthesis of Protected α-Hydrazino Esters and Selective Aerobic Oxidation with Catalytic Pt/Bi/C for Synthesis of Imidazole-4,5-dicarbaldehyde Bowman, Roy K.; Brown, Andrew D.; Cobb, Jannine H. The Journal of Organic Chemistry, Vol. 78, Issue 23 https://doi.org/10.1021/jo4014595	journal	November 2013
Theoretical Foundations Lewis, Bernard; von Elbe, Guenther Combustion, Flames and Explosions of Gases https://doi.org/10.1016/B978-0-12-446751-4.50007-X	book	January 1987
Development of safe and scalable continuous-flow methods for palladium-catalyzed aerobic oxidation reactions Ye, Xuan; Johnson, Martin D.; Diao, Tianning Green Chemistry, Vol. 12, Issue 7 https://doi.org/10.1039/c0gc00106f	journal	January 2010
Flammability envelopes for methanol, ethanol, acetonitrile and toluene Brooks, Mark R.; Crowl, Daniel A. Journal of Loss Prevention in the Process Industries, Vol. 20, Issue 2 https://doi.org/10.1016/j.jlp.2007.01.001	journal	March 2007
On the minimum ignition energy (MIE) for propane/air Eckhoff, R. K.; Ngo, M.; Olsen, W. Journal of Hazardous Materials, Vol. 175, Issue 1-3 https://doi.org/10.1016/j.jhazmat.2009.09.162	journal	March 2010
Development and Scale-Up of Three Consecutive Continuous Reactions for Production of 6-Hydroxybuspirone LaPorte, Thomas L.; Hamedi, Mourad; DePue, Jeffrey S. Organic Process Research & Development, Vol. 12, Issue 5 https://doi.org/10.1021/op800079u	journal	August 2008
Recent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular Oxygen Punniyamurthy, T.; Velusamy, Subbarayan; Iqbal, Javed Chemical Reviews, Vol. 105, Issue 6 https://doi.org/10.1021/cr050523v	journal	June 2005
Flammability zone prediction using calculated adiabatic flame temperatures Mashuga, Chad V.; Crowl, Daniel A. Process Safety Progress, Vol. 18, Issue 3 https://doi.org/10.1002/prs.680180303	journal	October 1999
Large-Scale Oxidations in the Pharmaceutical Industry ^† Caron, Stéphane; Dugger, Robert W.; Ruggeri, Sally Gut Chemical Reviews, Vol. 106, Issue 7 https://doi.org/10.1021/cr040679f	journal	July 2006
Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant Shi, Zhuangzhi; Zhang, Chun; Tang, Conghui Chemical Society Reviews, Vol. 41, Issue 8 https://doi.org/10.1039/c2cs15224j	journal	January 2012

Similar Records

Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules

Journal Article · Fri Oct 07 00:00:00 EDT 2016 · Chemical Science · OSTI ID:1179621

Hruszkewycz, Damian P.; Miles, Kelsey C.; Thiel, Oliver R.; +1 more

Assessing the structural integrity of a lyophilized protein in organic solvents

Journal Article · Wed Apr 12 00:00:00 EDT 1995 · Journal of the American Chemical Society · OSTI ID:1179621

Desai, U R; Klibanov, A M

Investigation of Complex Intermediates in Solvent-Mediated Synthesis of Thiophosphate Solid-State Electrolytes

Journal Article · Wed Dec 02 00:00:00 EST 2020 · Journal of Physical Chemistry. C · OSTI ID:1179621

Delnick, Frank M.; Yang, Guang; Self, Ethan C.; +2 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES

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

Citation Formats

References (26)

Similar Records

Related Subjects