Dipicrylamine

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Structural formula
Structure of dipicrylamine
General
Surname Dipicrylamine
other names
  • 2,2,4,4,6,6-hexanitrodiphenylamine
  • 2,4,6-trinitro- N - (2,4,6-trinitrophenyl) aniline
  • Dipicrylamine
  • Hexanitrodiphenylamine
  • Imperial yellow
  • HNDPhA
  • HNDP
  • CI 10360
Molecular formula C 12 H 5 N 7 O 12
Brief description

yellow, explosive prisms

External identifiers / databases
CAS number 131-73-7
EC number 205-037-8
ECHA InfoCard 100.004.581
PubChem 8576
ChemSpider 8258
Wikidata Q414335
properties
Molar mass 439.21 g mol −1
Physical state

firmly

density

1.64 g cm −3

Melting point

244 ° C decomposes

solubility
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
01 - Explosive 06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 201-330-310-300-373-411
P: ?
Toxicological data

> 500 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dipikrylamine (also aurantia or imperial yellow ) is a tar dye that was used in the past to dye wool and silk and especially leather. The brick-red powder turns a splendid yellow. Emil Kopp discovered the dye in 1873. Sometimes the ammonium or sodium salt of dipicrylamine is called aurantia . The substance falls within the scope of the Explosives Act and is divided into substance group A in Appendix II.

Extraction and presentation

By condensing 2,4-dinitrochlorobenzene and aniline , dinitrodiphenylamine is first obtained , which is nitrated to dipikrylamine in a mixture of concentrated sulfuric acid and nitric acid .

properties

The connection is particularly explosive when dry due to impact, friction, heat and other ignition sources and is subject to the Explosives Act .

Table with important explosion-relevant properties:
Oxygen balance −52.8%
Nitrogen content 22.33%
Normal gas volume 913 l kg −1
Explosion heat 4042 kJ kg −1 (H 2 O (l))
3975 kJ kg −1 (H 2 O (g))
Specific energy 1098 kJ kg −1 (112 mt / kg)
Lead block bulge 32.5 cm 3 g −1
Detonation velocity 7200 m · s −1
Steel sleeve test Limit diameter 5 mm
Sensitivity to impact 12 Nm
Rubbing sensitivity no reaction up to 353 N pin load

use

The compound was used in mixtures with trinitrotoluene and aluminum as an underwater explosive (→ gunwool 36 ).

Individual evidence

  1. ↑ a b c Entry on dipicrylamine. In: Römpp Online . Georg Thieme Verlag, accessed on March 24, 2014.
  2. ↑ a b c d e f g h i j k l m J. Köhler, R. Meyer, A. Homburg: Explosivstoffe. 10th, completely revised edition. Wiley-VCH, Weinheim 2008, ISBN 978-3-527-32009-7 , p. 161.
  3. ↑ a b c Entry on hexanitrodiphenylamine in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
  4. ↑ Entry for CAS no. 131-73-7 in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)
  5. ↑ Entry on Dipicrylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ section and images of Aurantia at Picture Library (English) .
  7. ^ Sprengstoffgesetz - SprengG , accessed on November 5, 2018
  8. ↑ L. Roth, U. Weller: Hazardous chemical reactions. 65th supplementary delivery, ecomed-Verlag 2011.
  9. ↑ Explosives Act, Appendix I, List of Explosive Substances ( BGBl. 1975 I p. 853 ), to which the law is to be applied in full.

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