OPRD safety issue

‘Tis the season…for Organic Process Research & Development‘s annual “Safety Of Chemical Processes” section. The issue contains literature highlights, summarized as Safety Notables, as well as original papers.

First, though, comes an editorial by editor Trevor Laird, with a caution on including needed information in documents versus being overly comprehensive:

I recently reviewed a batch record for a simple process (add reagents, heat, monitor until complete, cool, quench, filter, and dry) and was surprised at the length of the document—over 300 pages. There was no doubt that the document was extremely comprehensive, but the question I ask is, Was it likely to be read by the process operator in the amount of detail that was provided? It was extremely complex, and I felt that any safety messages would have been lost in all the detail. In fact, with a document of such complexity I suspected that the operator would be more likely to make mistakes through having misunderstood what he was supposed to do. Surely these batch records can be simplified so that the operator’s instructions are clear. I must admit that I found it difficult to read the entire document and to find the information that I wanted.


Topics in the Safety Notables:

  • Toxic tips, pointing to William Luttrell‘s organic molecule reviews in the Journal of Chemical Health & Safety
  • Expansion of a solvent selection guide
  • Workplace safety
  • Synthesis of energetic materials
  • Dust explosion hazards
  • Learning from history
  • Safer reagents and reagent handling
  • A safe and practical procedure for difluoromethylation
  • Process hazard analysis
  • Deciphering the MSDS
  • Comparison of two methods for self-accelerating decomposition temperature (SADT) determination
  • Safety issues with nanomaterials
  • Inherently safer technology
  • Safe, scalable nitric acid oxidation
  • Chemical safety alert, pointing to the C&EN safety letter from Northwestern’s Joseph Hupp and SonBinh Nguyen regarding an explosion involving aqueous hydrogen peroxide and acetic anhydride
  • Flashpoints
  • Continuous process for alkene ozonolysis
  • Investigating exothermic activity
  • Development of a safe and practical N-oxidation procedure
  • Drum pressurization
  • Trimethylsilyldiazomethane: A safe nonexplosive, cost-effective, and less toxic reagent for phenol derivatization in GC applications. I’m going to quibble with this, because after looking into two deaths in 2008 from TMSD exposure, it’s not at all clear to me that it is less toxic than diazomethane. I’ve requested the paper from the corresponding author–I’m curious to see what their evidence is for that assertion.
  • Process safety and the human factor
  • A safe and practical procedure for global deprotection of oligoribonucleotides
  • Mining the web for safety information

Full papers, communications, and technical notes:

  • Determination of Accurate Specific Heat Capacities of Liquids in a Reaction Calorimeter, by Statistical Design (from Sanofi-Aventis)
  • Design and Scale-Up of Diels–Alder Reactions for the Practical Synthesis of 5-Phenylbicyclo[2.2.2]oct-5-en-2-one (from Actelion Pharmaceuticals , in Switzerland)
  • Safe, Convenient ortho-Claisen Thermal Rearrangement Using a Flow Reactor (from Eli Lilly)
  • Pilot Plant Preparation of tert-Butyl-4-(2-hydroxyethyl)-4-(pyrrolidin-1-yl)-piperidine-1-carboxylate, An Intermediate of Novel Antiarteriosclerotics, Via a Safe, Scalable Reformatsky-Type Reaction (from Shionogi, in Japan)
  • Heat Pipe-Mediated Control of Fast and Highly Exothermal Reactions (from Johannes Gutenberg University Mainz, in Germany)
  • The Safe Use of Sodium Hydride on Scale: The Process Development of a Chloropyrimidine Displacement (from Merck)
  • Nitration Chemistry in Continuous Flow using Fuming Nitric Acid in a Commercially Available Flow Reactor (from Novartis)
  • A Safe Two-Step Process for Manufacturing Glycidyl Nitrate from Glycidol Involving Solid–Liquid Phase-Transfer Catalysis (from Universidad Alfonso X el Sabio and Tecnalia-Energy, both in Spain)
  • Application of Process Analytical Technology Tools for the Safe and Reliable Production of a Dihydro-1H-imidazole (from Roche)
  • Process Safety Evaluation of a Tungsten-Catalyzed Hydrogen Peroxide Epoxidation Resulting In a Runaway Laboratory Reaction (from GlaxoSmithKline)

Edited to correct typos

Author: Jyllian Kemsley

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