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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.3K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.8K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Nitrosation of Enols01:19

Nitrosation of Enols

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.6K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.0K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Updated: Jul 6, 2025

Laboratory Scale Slow Cook-Off Testing of Rocket Propellants: The Combustion Rate Analysis of a Slowly Heated Propellant CRASH-P Test
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Laboratory Scale Slow Cook-Off Testing of Rocket Propellants: The Combustion Rate Analysis of a Slowly Heated Propellant CRASH-P Test

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Nitroiminotriazole (NIT) based potential solid propellants: synthesis, characterization, and applications.

Sohan Lal1, Richard J Staples2, Jean'ne M Shreeve1

  • 1Department of Chemistry, University of Idaho, Moscow, Idaho, 83844-2343, USA. jshreeve@uidaho.edu.

Dalton Transactions (Cambridge, England : 2003)
|January 3, 2024
PubMed
Summary

Researchers developed novel triazole-based nitroimino compounds and energetic salts. These new high energy density materials offer excellent stability and performance, addressing a key challenge in energetic materials science.

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Area of Science:

  • Energetic Materials Science
  • Organic Chemistry
  • Materials Science

Background:

  • Nitroimino compounds are a unique class of high energy density materials (HEDM).
  • Synthesizing insensitive nitroimino compounds presents a significant challenge in the field.
  • Developing novel energetic materials with improved safety and performance is crucial.

Purpose of the Study:

  • To synthesize and characterize novel triazole-based nitroimino compounds.
  • To explore the properties of their high-nitrogen green energetic salts.
  • To evaluate their potential as advanced energetic materials.

Main Methods:

  • Synthesis of triazole-based nitroimino compounds and their energetic salts.
  • Characterization of thermal and mechanical stability.
  • Evaluation of detonation and ballistic properties.

Main Results:

  • Excellent yields of novel triazole-based nitroimino compounds and energetic salts were achieved.
  • Materials exhibited high positive heats of formation (7.84 to 735.29 kJ mol⁻¹).
  • Good densities (1.66 to 1.98 g cm⁻³), detonation properties (P = 22.02–31.88 GPa; D = 7472–8936 m s⁻¹), and ballistic properties (Isp = 205.66–295.35 s; C* = 1065–1832 m s⁻¹) were observed.
  • High thermal stability (Td = 136–378 °C) and mechanical stability (IS = 10–40 J; FS = 120–360 N) were demonstrated.

Conclusions:

  • Novel triazole-based nitroimino compounds and their energetic salts were successfully synthesized.
  • These materials possess a promising combination of high energy, good stability, and desirable performance characteristics.
  • The developed compounds represent a significant advancement in the design of insensitive high energy density materials.