Process for the preparation of a-methyl-[4-(nitro)-2-(trifluoromethyl)-benzyl nitrate

Patent metadata

Field	Value
Publication number	US-12410119-B2
Application number	US-202017634276-A
Country	US
Kind code	B2
Filing date	Sep 2, 2020
Priority date	Sep 12, 2019
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

The present invention relates to a process for the preparation of α-methyl-[4-(nitro)-2-(trifluoromethyl)]-benzyl nitrate and to the α-methyl-[4-(nitro)-2-(trifluoromethyl)]-benzyl nitrate.

First claim

The invention claimed is:

1. A process for preparing a compound of formula (I)

comprising:
(ii) reacting a compound of formula (II)

with nitric acid in the presence of sulfuric acid or oleum,
wherein the nitric acid is used in an amount of 2 to 20 mole
equivalents per 1 mole of the compound (II).

2. The process of claim 1 , wherein the nitric acid is used in an amount of 2 to 10 mole equivalents per 1 mole of the compound (II).

3. The process of claim 1 , wherein the nitric acid has a concentration of from 95 to 100 mol % or is a fuming nitric acid.

4. The process of claim 1 -to 4, wherein the reaction is carried out in the presence of the sulfuric acid.

5. The process of claim 1 , wherein the sulfuric acid has a concentration of from 95 to 100 mol %.

6. The process of claim 1 , wherein the reaction is carried out in the presence of oleum.

7. The process of claim 1 , wherein a molar ratio of the nitric acid to the sulfuric acid or oleum is from 1:1 to 1:20.

8. The process of claim 1 , wherein the molar ratio of the nitric acid to the sulfuric acid or oleum is from 1:2 to 1:6.

9. The process of claim 1 , wherein the reaction is carried out in a chlorinated aliphatic solvent.

10. The process of claim 1 , wherein in a step (i)
a) the compound (II) is first reacted with at least 1 mole equivalents of the nitric acid per 1 mole of the compound (II) to obtain an intermediate compound (A)

b) water, optionally together with the excess of the nitric acid and sulfuric acid or oleum, is removed from the reaction mixture and
c) the compound (A) is further reacted with 1 to 2.5 mole equivalents of the nitric acid per 1 mole of the compound (A) to obtain the compound (I).

11. The process of claim 10 , wherein in the step (i) a) 1 to 1.5 mole equivalents of the nitric acid per 1 mole of the compound (II) are used.

12. The process of claim 1 , carried out in a continuous mode of operation.

13. The process of claim 10 , further comprising
(iii) separating excess of the nitric acid and sulfuric acid or oleum from the reaction mass, optionally adjusting the concentration to reach an initial concentration, and thereafter returning it to the nitration step i).

14. The process of claim 13 , wherein excess of the nitric acid and sulfuric acid or oleum is returned to step i) a).

15. A compound of formula (I) or formula (A)

Assignees

• Basf Agro Bv

Inventors

• Frassetto Timo
• Vogt Florian
• Yerande Swapnil
• Alznauer Christiane
• Illies Sebastian
• Muelheims Philip
• Saelinger Daniel
• Thiele Robin
• Sutoris Heinz Friedrich

Classifications

• C07C205/11

  having nitro groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C203/02

  Esters of nitric acid · CPC title

• C07C201/16

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C201/08 Primary

  by substitution of hydrogen atoms by nitro groups · CPC title

• C07C201/02 Primary

  Preparation of esters of nitric acid · CPC title