Method for producing the pentazolate anion using a hypervalent iodine oxidant

Patent metadata

Field	Value
Publication number	US-12595174-B2
Application number	US-202218688565-A
Country	US
Kind code	B2
Filing date	Aug 30, 2022
Priority date	Sep 3, 2021
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

A method for producing the pentazolate anion, includes at least the oxidation of a phenolic arylpentazole by a particular hypervalent iodine oxidant in the presence of a base.

First claim

The invention claimed is:

1 . A method for producing the pentazolate anion, comprising:
oxidation of a phenolic arylpentazole by a hypervalent iodine oxidant in the presence of a base, said hypervalent iodine oxidant being of general formula A-B, wherein group A designates a benzene ring, and group B is a structure comprising a hypervalent iodine atom having one of the two formulas B1 or B2 below:

with *— designating, in the formulas B1 and B2, the bond of the hypervalent iodine atom to the benzene ring A,
in formula B2, R 1 and R 2 being identical or different and chosen independently of one another from: **—OCOR, **—OR, where R designates a linear or branched, alkyl chain comprising between 1 and 4 carbon atoms, or R 1 being **—OH and R 2 being **—OTs with Ts designating a tosyl group, where **— designates the bond of the oxygen atom to the hypervalent iodine, the phenolic arylpentazole having the following chemical structure:

R 3 and R 4 being identical or different and chosen independently of one another from: the, linear or branched, alkyl chains comprising between 1 and 4 carbon atoms, not substituted or substituted by a C 1 or C 2 alkoxy group or by a dialkylamine.

2 . The method according to claim 1 , wherein the oxidation is carried out in a solvent comprising hexafluoroisopropanol and at least one compound chosen from alcohols or acetonitrile.

3 . The method according to claim 1 , wherein group B is of formula B1.

4 . The method according to claim 3 , wherein group B is of formula B1 and the oxidation is carried out in a solvent comprising hexafluoroisopropanol and at least one compound chosen from alcohols or acetonitrile.

5 . The method according to claim 1 , wherein group B is of formula B2 with R 1 and R 2 identical and each designating **—OCOMe or **—OMe, where Me designates a methyl group.

6 . The method according to claim 1 , wherein the base comprises at least one compound chosen from: an alkali hydroxide, an alkaline-earth hydroxide, a metal hydroxide, ammonium hydroxide, a quaternary ammonium hydroxide, an alkali carbonate or a mixture of these compounds.

7 . The method according to claim 6 , wherein the base is sodium hydroxide.

8 . The method according to claim 1 , wherein the oxidation is carried out in a solvent and wherein the method further comprises, successively:
removal of the solvent, liquid-liquid extraction, using an extraction solvent, in order to remove the oxidant residues, removal of the extraction solvent, and selective extraction of the pentazolate anion after this removal, the pentazolate anion being selectively extracted in a liquid medium comprising at least one of ethanol, acetonitrile or acetone, or a mixture of these compounds.

9 . A method for producing an energetic composition, comprising at least the production of the pentazolate anion by a method according to claim 1 , and mixing of the pentazolate anion thus produced with a binder in order to obtain the energetic composition.

Assignees

• Arianegroup Sas
• Centre National De La Recherche Scient
• Univ Claude Bernard Lyon 1

Inventors

• Joucla Lionel
• Gasnier Gwénaël
• Comte Sébastien
• Silva Costa Raphaël

Classifications

• C06B43/00

  Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00 · CPC title

• C01B21/00 Primary

  Nitrogen; Compounds thereof · CPC title

• C07D259/00 Primary

  Heterocyclic compounds containing rings having more than four nitrogen atoms as the only ring hetero atoms · CPC title