Method for producing 1,1,1-trifluoro-2,2-bisarylethane, and 1,1,1-trifluoro-2,2-bisarylethane

Patent metadata

Field	Value
Publication number	US-12435185-B2
Application number	US-202017428762-A
Country	US
Kind code	B2
Filing date	Feb 3, 2020
Priority date	Feb 6, 2019
Publication date	Oct 7, 2025
Grant date	Oct 7, 2025

Abstract

The present invention has the effect of making it possible to produce 1,1,1-trifluoro-2,2-bisarylethane efficiently by a simple procedure by condensing a mixture of fluoral and hydrogen fluoride with an aryl compound under anhydrous conditions. The purity of the 1,1, 1-trifluoro-2, 2-bisarylethane obtained can be raised by a simple purification method such as crystallization or distillation. The obtained 1,1,1-trifluoro-2,2-bisarylethane can be increased in purity by a simple purification method such as crystallization operation or distillation.

First claim

The invention claimed is:

1. A production method for obtaining 1,1,1-trifluoro-2,2-bisarylethane, the method comprising subjecting an aryl compound represented by General

wherein, in General Formula [1], X 1 each independently represents a hydroxyl group, an amino group, a carboxyl group, or a halogen, m represents an integer of 0 to 3, R 1 each independently represents a monovalent organic group, and n represents an integer of 0 to (5-m),
to a condensation reaction with a mixture of fluoral and hydrogen fluoride under anhydrous conditions,
the 1,1,1-trifluoro-2,2-bisarylethane being represented by

wherein, in General Formula [2], X 1 , R 1 , m, and n each have the same definition as X 1 , R 1 , m, and n in General Formula [1].

2. The production method according to claim 1 , wherein a Lewis acid or a Bronsted acid is added as an additive to the reaction.

3. The production method according to claim 2 , wherein the Lewis acid or the Bronsted acid is at least one selected from the group consisting of an inorganic acid, an organic acid, and a metal halide.

4. The production method according to claim 3 , wherein the inorganic acid is at least one selected from the group consisting of phosphoric acid, hydrogen chloride, hydrogen bromide, concentrated nitric acid, concentrated sulfuric acid, fuming nitric acid, and fuming sulfuric acid, and the organic acid is at least one selected from the group consisting of formic acid, acetic acid, oxalic acid, benzoic acid, methanesulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid, and trifluoromethanesulfonic acid.

5. The production method according to claim 3 , wherein the metal halide is a metal halide containing at least one metal selected from the group consisting of boron (III), tin (II), tin (IV), titanium (IV), zinc (II), aluminum (III), antimony (III), and antimony (V).

6. The production method according to claim 5 , wherein the metal halide is at least one selected from the group consisting of boron (III) trifluoride, aluminum (III) trichloride, zinc (II) dichloride, titanium (IV) tetrachloride, tin (IV) tetrachloride, and antimony (V) pentachloride.

7. The production method according to claim 1 , wherein the reaction is carried out without using an organic solvent.

8. The production method according to claim 1 , wherein the reaction is carried out in a temperature range of −20° C. to +200° C. and a pressure range of 0.1 MPa to 4.0 MPa (absolute pressure).

9. 1,1,1-trifluoro-2,2-bisarylethane represented by

wherein, in Formula [5], n represents an integer of 1 to 4.

10. The 1,1,1-trifluoro-2,2-bisarylethane according to claim 9 , which is 1,1,1-trifluoro-2,2-bis (3-amino-4-hydroxyphenyl) ethane represented by

11. 1,1,1-trifluoro-2,2-bisarylethane represented by Formula [7], with the proviso that the following compounds are excluded:

wherein, in Formula [7], n represents an integer of 1 to 4.

12. The 1,1,1-trifluoro-2,2-bisarylethane according to claim 11 , which is 1,1,1-trifluoro-2,2-bis (2,5-dimethyl-4-hydroxyphenyl) ethane represented by Formula [7a]:

wherein, in Formula [7a], Me represents a methyl group.

Assignees

• Central Glass Co Ltd

Inventors

• Hosoi Kenji
• Hirotaki Kensuke
• Murakami Yosuke
• Hori Hiroto
• Eguchi Hiroshi

Classifications

• C08G73/1028

  characterised by the process itself, e.g. steps, continuous · CPC title

• C08G73/123

  the unsaturated precursors comprising halogen-containing substituents · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C07C215/80

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C07C213/08

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title