Nitration and Nitrocompounds

Abstract

In the course of studying new superacid system in nitration we evaluated the nitric-tetratriflatoboric acid system HNO3-HB(O3SCF3)4 for its nitrating ability of aromatics. Tetratriflatoboric acid, HB(O3SCF3)4 was conveniently prepared in situ from triflic acid (excess) and boron trichloride and could be used without any workup. Nitration of benzene, toluene, fluorobenzene, chlorobenzene, anisole and naphthalene was studied with HNO3-HB(O3SCF3)4 in methylene chloride solution at -30 deg C and at room temperature. the new superacidic nitration of toluene gave very low (1%) meta nitration both at - 30 deg C and at room temperature. At the same time the ortholpara isomer ratio is also lower than in most studied nitronium ion nitrations, indicating ion pairing or association with bulky tetratriflatoborate anion. Similarly high regio(positional) selectivity was found in nitration of the other aromatics.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1991
Accession Number
ADA243380

Entities

Organizations

  • University of Southern California

Tags

Communities of Interest

  • Energy and Power Technologies

DTIC Thesaurus Topics

  • Acids
  • Adamantanes
  • Amines
  • Barium Oxides
  • Chlorides
  • Energetic Materials
  • High Energy
  • Hydrocarbons
  • Materials
  • Nitration
  • Nitric Acid
  • Nitriles
  • Nitrogen Compounds
  • Nitrogen Oxides
  • Nitromethane
  • Static Pressure
  • Sulfonic Acids

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry