Potential Explosion Hazards Associated with the Autocatalytic Thermal Decomposition of Dimethyl Sulfoxide and Its Mixtures

Dimethyl sulfoxide (DMSO) is widely used as a solvent for chemical reactions, as a cosolvent for crop protection formulations, and in medicines for topical administration of drugs. The potential ex...

[1]  Nicholas R. Babij,et al.  Potential Safety Hazards Associated with Pd-Catalyzed Cross-Coupling Reactions , 2019, Organic Process Research & Development.

[2]  E. Corey,et al.  A New Synthesis of Ketones , 1964 .

[3]  R. Pummerer Über Phenylsulfoxy-essigsäure. (II.) , 1910 .

[4]  E. Corey,et al.  Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene , 2002 .

[5]  B. Brandes,et al.  Calorimetric study of the exothermic decomposition of dimethyl sulfoxide , 2016 .

[6]  W. M. Weaver,et al.  A NEW AND SELECTIVE METHOD OF OXIDATION , 1957 .

[7]  M. Bollyn DMSO Can Be More than a Solvent: Thermal Analysis of Its Chemical Interactions with Certain Chemicals at Different Process Stages , 2006 .

[8]  D. Hands,et al.  Development of a Scaleable Synthesis of a 3-Aminopyrazinone Acetamide Thrombin Inhibitor , 2004 .

[9]  Francis Stoessel,et al.  Thermal Safety of Chemical Processes , 2020 .

[10]  D. V. Banthorpe,et al.  Potential Toxicity of Solutions of Dimethyl Sulphoxide , 1967, Nature.

[11]  Charles D. Gagliardi,et al.  Process Development of an Inherently Safer Oxidation: Synthesis of 2-Chloro-6-methylbenzoic Acid in the R411 Manufacturing Process , 2005 .

[12]  Ö. Farkas,et al.  Mechanism for the Oxidation of Sulfides and Sulfoxides with Periodates: Reactivity of the Oxidizing Species , 2009 .

[13]  E. Buncel,et al.  Proton-transfer and electron-transfer processes in reaction of p-nitrotoluene with bases. A spectrophotometric study , 1980 .

[14]  J. Tsuji,et al.  Organic syntheses by means of noble metal compounds. XXXVI. Reactions of carbanions with cyclooctadienepalladium and platinum halide complexes and tetraphenylcyclobutadienepalladium chloride complex , 1968 .

[15]  Christer L. Øpstad,et al.  Formation of DMSO and DMF radicals with minute amounts of base , 2009 .

[16]  L. Whiting,et al.  A cradle-glass ampoule sample container for differential scanning calorimetric analysis , 1980 .

[17]  P. Gardner,et al.  Nucleophilic additions to substituted cyclopropenes , 1967 .

[18]  Craig A. Tucker,et al.  Practical Use of Differential Scanning Calorimetry for Thermal Stability Hazard Evaluation , 2019, Organic Process Research & Development.

[19]  E. Corey,et al.  Some New Reactions of Methylsulfinyl and Methylsulfonyl Carbanion1 , 1963 .

[20]  J. A. Marshall,et al.  Studies relating to the synthesis of (+)-valeranone , 1968 .

[21]  K. Jung,et al.  Phosphorus pentoxide/dimethyl sulfoxide/triethylamine (PDT): a convenient procedure for oxidation of alcohols to ketones and aldehydes , 1987 .

[22]  E. Janzen,et al.  Electron-Transfer Processes. I. The Scope of the Reaction between Carbanions or Nitranions and Unsaturated Electron Acceptors , 1964 .

[23]  T. Vickery,et al.  Thermal hazards and safe scale-up of reactions containing dimethyl sulfoxide , 2006 .

[24]  A. Schriesheim,et al.  Methylation of Simple Unsaturated Hydrocarbons by Dimethyl Sulfoxide , 1965 .

[25]  L. E. Small,et al.  Weak acids in strong bases. I. Thermochemical method for comparing acidities , 1973 .

[26]  S. Danishefsky,et al.  The Methylation of 1,2-Diarylethylenes by Dimethylsulfinyl Carbanion , 1966 .

[27]  Rebecca T. Ruck,et al.  Merck’s Reaction Review Policy: An Exercise in Process Safety , 2013 .

[28]  W. Reynolds,et al.  Dimethyl Sulfoxide in Inorganic Chemistry , 2007 .

[29]  S. Weiner,et al.  Methylation of Aromatic Hydrocarbons by Dimethyl Sulfoxide in the Presence of Base1 , 1966 .

[30]  Lars Ole Lyngsø,et al.  Route Scouting and Process Development of Lu AA26778 , 2008 .

[31]  F. W. Sweat,et al.  Dimethyl Sulfoxide Oxidations , 1967 .

[32]  E. Smith,et al.  THE SINGLE–AND REPEATED–DOSE TOXICITY OF DIMETHYL SULFOXIDE , 1967, Annals of the New York Academy of Sciences.

[33]  David J. Frurip,et al.  Effective use of differential scanning calorimetry in reactive chemicals hazard evaluation , 2007 .

[34]  A. Mancuso,et al.  Structure of the dimethyl sulfoxide-oxalyl chloride reaction product. Oxidation of heteroaromatic and diverse alcohols to carbonyl compounds , 1979 .

[35]  Willhite Cc,et al.  Toxicology updates. Dimethyl sulfoxide. , 1984 .

[36]  E. Corey,et al.  Dimethylsulfonium Methylide, a Reagent for Selective Oxirane Synthesis from Aldehydes and Ketones , 1962 .

[37]  Ivan Marziano,et al.  Critical assessment of pharmaceutical processes--A rationale for changing the synthetic route. , 2006, Chemical reviews.

[38]  R. Dessy,et al.  Assisted Acetolysis of Tributyltin Hydride , 1964 .

[39]  E. Janzen,et al.  Autoxidation and Condensation Reactions of Carbanions in Dimethyl Sulfoxide Solution , 1962 .

[40]  Influence of organic acid on the thermal behavior of dimethyl sulfoxide , 2015, Journal of Thermal Analysis and Calorimetry.

[41]  D. I. Townsend,et al.  Thermal hazard evaluation by an accelerating rate calorimeter , 1980 .

[42]  F. Saadati,et al.  Development of a Metal-Free Oxidation of Alcohols with Dimethyl Sulfoxide (DMSO) Activated by Tosyl Chloride , 2014 .

[43]  G. Giacomelli,et al.  A mild and efficient alternative to the classical Swern oxidation. , 2001, The Journal of organic chemistry.

[44]  K. Christe,et al.  Cesium Fluoroxysulfate (Cesium Fluorine Sulfate) , 2007 .

[45]  D. Swern,et al.  Oxidation of alcohols by “activated” dimethyl sulfoxide. a preparative, steric and mechanistic study , 1978 .

[46]  V. Filimonov,et al.  The reaction of alkynes with dimethyl sulfoxide, halogenated hydrocarbons and sulfur trioxide , 2008 .

[47]  Steven M. Richter,et al.  Safe Scale-Up of Pharmaceutical Manufacturing Processes with Dimethyl Sulfoxide as the Solvent and a Reactant or a Byproduct , 2014 .

[48]  Daniel Swern,et al.  Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis , 1981 .

[49]  W. Doering,et al.  Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide , 1967 .

[50]  M. Russ,et al.  Elementorganische Verbindungen, XI. Chlortrimethylsilan/Natriumbromid - Ein einfaches System zur in-situ-Erzeugung von Bromtrimethylsilan. Umsetzung mit Ketonen, Sulfoxiden und anderen sauerstoffhaltigen Substraten , 1981 .

[51]  J. R. McConnell,et al.  The Swern Oxidation: Development of a High-Temperature Semicontinuous Process , 2008 .

[52]  W. Hergenrother,et al.  Dehydration of Alcohols, Diols, and Related Compounds in Dimethyl Sulfoxide1 , 1964 .

[53]  C. Brown Saline hydrides and superbases in organic reactions. VII. Potassium hydride, highly active new hydride reagent. Reactivity, applications, and techniques in organic and organometallic reactions , 1974 .

[54]  Peter A. Lee,et al.  A review of dimethylsulfoxide in aquatic environments , 1999 .

[55]  J. Bunnett,et al.  Base-induced dehalogenation of aryl halides in tert-butyl alcohol-dimethyl sulfoxide and similar solvent mixtures , 1968 .

[56]  S. Richter,et al.  Safety Concerns in a Pharmaceutical Manufacturing Process Using Dimethyl Sulfoxide (DMSO) as a Solvent , 2012 .

[57]  Min Sheng,et al.  Explosion Hazards of Sodium Hydride in Dimethyl Sulfoxide, N,N-Dimethylformamide, and N,N-Dimethylacetamide , 2019, Organic Process Research & Development.

[58]  Hong‐Cai Zhou,et al.  A coordinatively linked Yb metal-organic framework demonstrates high thermal stability and uncommon gas-adsorption selectivity. , 2008, Angewandte Chemie.

[59]  L. E. Small,et al.  Ionization of group 6 and 7 protonic acids in dimethyl sulfoxide , 1977 .

[60]  K. Karan,et al.  Kinetic Studies of Reaction between Sodium Borohydride and Methanol, Water, and Their Mixtures , 2007 .

[61]  J. Rosenberg,et al.  Adverse reactions of dimethyl sulfoxide in humans: a systematic review , 2018, F1000Research.

[62]  Qiang Yang,et al.  Mizoroki–Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards , 2019, Organic Process Research & Development.

[63]  Stanley G. Smith,et al.  Sulfoxides as nucleophiles , 1958 .

[64]  C. Alemán,et al.  Novel Epoxy Coating Based on DMSO as a Green Solvent, Reducing Drastically the Volatile Organic Compound Content and Using Conducting Polymers As a Nontoxic Anticorrosive Pigment , 2013 .

[65]  S. Ahrland,et al.  Metal Halide and Pseudohalide Complexes in Dimethylsulfoxide Solution. I. Dimethyl Sulfoxide Solvates of Silver(I), Zinc(II), Cadmium(II), and Mercury(II). , 1974 .

[66]  Literature Highlights , 2020 .

[67]  J. D. Albright,et al.  Dimethyl sulfoxide-acid anhydride mixtures for the oxidation of alcohols , 1967 .

[68]  Hongyuan Wei,et al.  Effects of incompatible substances on the thermal stability of dimethyl sulfoxide , 2013 .

[69]  Qingyuan Wang,et al.  Using the Green Solvent Dimethyl Sulfoxide To Replace Traditional Solvents Partly and Fabricating PVC/PVC-g-PEGMA Blended Ultrafiltration Membranes with High Permeability and Rejection , 2019, Industrial & Engineering Chemistry Research.

[70]  P. F. Vogt,et al.  Safety Notables: Information from the Literature , 2003 .

[71]  W. Hergenrother,et al.  Dehydration of Alcohols in Dimethyl Sulfoxide1,2 , 1962 .

[72]  D. A. Davenport,et al.  An Acid-catalyzed Cleavage of Sulfoxides1 , 1961 .

[73]  J. Cha,et al.  Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane , 2010 .

[74]  Process Development for the Crop Safener Cloquintocet Acid , 2019, Organic Process Research & Development.

[75]  Qiang Yang,et al.  Safety Evaluation of the Copper-Mediated Cross-Coupling of 2-Bromopyridines with Ethyl Bromodifluoroacetate , 2018, Organic Process Research & Development.

[76]  W. Hergenrother,et al.  The Selective Oxidation of Arylcarbinols to Aldehydes , 1964 .

[77]  W. Hergenrother,et al.  Decomposition of Dimethyl Sulfoxide Aided by Ethylene Glycol, Acetamide, and Related Compounds1 , 1964 .

[78]  D. Cram,et al.  Electrophilic Substitution at Saturated Carbon. XXXII. Spectroscopic Observation of Enantiomer Interconversion of 2,2-Dimethyl-1-phenylsulfonylcyclopropyl Anions , 1967 .

[79]  Defeng Zhao,et al.  Mild and Efficient Deoxygenation of Sulfoxides to Sulfides Using HfCl4/KBH4 System , 2010 .

[80]  E. Corey,et al.  Methylsulfinyl Carbanion (CH3-SO-CH2-). Formation and Applications to Organic Synthesis , 1965 .

[81]  H. Hess,et al.  Notes - Reactions of Organic Halides with Dimethyl Sulfoxide , 1958 .

[82]  J. J. Monagle,et al.  Notes: Reactions of Sulfoxides with Organic Halides. Preparation of Aldehydes and Ketones , 1959 .

[83]  S. J. Cyvin,et al.  Crystal and Molecular Structure of Hexakis(dimethyl sulfoxide)cadmium(II) Perchlorate, [Cd((CH3)2SO)6](ClO4)2. , 1978 .

[84]  C. Carrasco,et al.  A Manganese N‐Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes , 2019, ChemCatChem.