An Investigation of the Shipp Hexanitrostilbene (HNS) Process

Abstract

This report describes the separation, characterization, and anlaysis of the products which the Shipp hexanitrostilbene (HNS) process yields. In this process, trinitrotoluene (TNT), dissolved in a mixture of tetrahydrofuran (THF) and methanol (MeOH), is reacted with commercial bleach (NaOCL) to form HNS. The isolated products include: hexanitrostilbene (HNS), hexanitrobibenzyl (HNBiB), trinitrobenzene (TNB), trinitrobenzoic acid (PiCOOH), trinitrobenzaldehyde (PiCHO), trinitrobenzyl chloride (PiCH2Cl), picryl chloride (PiCl), picric acid (PiOH), trinitrobenzyl alcohol (PiCH2OH), 4,6-dinitro 2,1 benzisoxazole (ANil), and trichloronitromehtane (chloropicrin) as well as some unreacted TNT. Approximately 5-10% of the red-tar fraction of the reaction mixture remains unidentified. Solvent effects on the yield of several of the above by-products are discussed; however, no other solvent examined displayed the pronounced specificity of tetrahydrofuran (THF) for this reaction.

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Document Details

Document Type
Technical Report
Publication Date
Aug 25, 1980
Accession Number
ADA092796

Entities

People

  • Eleonore G. Kayser

Organizations

  • Naval Ordnance Laboratory

Tags

Communities of Interest

  • Weapons Technologies

DTIC Thesaurus Topics

  • Acids
  • Alcohols
  • Chemistry
  • Chromatography
  • Explosives
  • Hydroxides
  • Liquid Chromatography
  • Liquids
  • Magnetic Resonance
  • Materials
  • Methanols
  • Munitions
  • Nuclear Magnetic Resonance
  • Picric Acid
  • Sodium Hydroxide
  • Water
  • Weapons

Fields of Study

  • Chemistry

Readers

  • Analytical Chemistry
  • Aquatic Ecology
  • Organic Chemistry