Hydrazine → N,N'-bis(4,4,4-trinitrobutyryl)hydrazine

HRID 2081347Notes

Reaction equation

HRID 2081347 reaction equation
[NH2:1][NH2:2].[N+:3]([C:6]([N+:15]([O-:17])=[O:16])([N+:12]([O-:14])=[O:13])[CH2:7][CH2:8][C:9](Cl)=[O:10])([O-:5])=[O:4]>CO>[N+:3]([C:6]([N+:15]([O-:17])=[O:16])([N+:12]([O-:14])=[O:13])[CH2:7][CH2:8][C:9]([NH:1][NH:2][C:9](=[O:10])[CH2:8][CH2:7][C:6]([N+:3]([O-:5])=[O:4])([N+:15]([O-:17])=[O:16])[N+:12]([O-:14])=[O:13])=[O:10])([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 125075564,4,4-Trinitrobutyryl chloride

Product 1

HCID 19799797N,N'-bis(4,4,4-trinitrobutyryl)hydrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Low temperatures also reduce side reactions with hydrazine as well as the reaction of the acid chloride with methanol Therefore the hydrazine solution and the 4,4,4-trinitrobutyryl chloride solution are mixed together at a temperature in the range of preferably about -40° C. to -100° C., more preferably from -60° C. to -90° C., and still more preferably from -70° C. to -85° C., with about -78° C. being most preferred. The resulting reaction solution is then put in ambient (room) temperature environment and allowed to warm up to a temperature in the range of from about -5° C. to about 25° C. The product N,N'-bis(4,4,4-trinitrobutyryl)hydrazine is then isolated using conventional techniques as illustrated in the example.

Workup

  1. customstill more preferably from -70° C. to -85° C.
  2. customwith about -78° C.
  3. customThe resulting reaction solution
  4. temperatureto warm up to a temperature in the range of from about -5° C. to about 25° C

Sources & evidence

ORD record
ord-aecdf96558bb46afa80fcb7c533d6e84
Source dataset
uspto-grants-1993_02
Patent number
US05183938

Reaction notes

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