IP Library Granted Patent US 7,868,213
Granted Patent B2
US 7,868,213 · App. 12/219,796 · Granted Jan 11, 2011

1,4-bis(bromodifluoromethyl) tetrafluorobenzene and producing method thereof

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,868,213
App. No.
12/219,796
Granted
Jan 11, 2011
Kind
B2
Abstract

A method for producing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (BFTFB) is disclosed. The target compound is predicted as a very potent monomer for low dielectric constant material. This method comprises the following steps: (a) mixing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (DFMTFB), a bromination agent, and a solvent (with or without) to form a mixture; (b) heating the mixture under UV radiation; and (c) purifying the resultant to obtain 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (BFTFB) with high purity.

Claims (33)

1. A method for producing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene comprising the following steps:

(a) mixing Br 2 and 1,4-bis(difluoromethyl)tetrafluorobenzene to form a mixture;

(b) heating the mixture under UV irradiation until the temperature thereof is raised to the range of 100 to 200°;

(c) extracting the mixture by a solvent to obtain a reaction solution; and

(d) purifying the reaction solution to afford 1,4-bis(bromodifluoromethyl) tetrafluorobenzene.

2. The method as claimed in claim 1 , wherein HBr is discharged and additional Br 2 is further added into the mixture at a fixed interval of time when the reaction is performed in the step (b).

3. The method as claimed in claim 1 , wherein the step (a) further comprises a process of adding a basic reagent into the mixture.

4. The method as claimed in claim 3 , wherein in the step (a), the basic reagent is selected from the group consisting of alkali metal carbonate, alkali metal hydroxide, alkali metal oxide, alkaline-earth metal carbonate, alkaline-earth metal hydroxide, and alkaline-earth metal oxide.

5. The method as claimed in claim 1 , wherein the reaction time of the step (b) is from 24 to 96 hours.

6. The method as claimed in claim 1 , wherein the reaction pressure of the step (b) is from 1 to 10 kg/cm 2 .

7. The method as claimed in claim 1 , wherein the reaction temperature of the step (b) is from 130 to 180°.

8. The method as claimed in claim 1 , wherein the molar ratio of Br 2 to 1,4-bis(difluoromethyl)tetrafluorobenzene is more than 2:1.

9. The method as claimed in claim 1 , wherein the solvent of the step (c) is a polar solvent.

10. The method as claimed in claim 9 , wherein the solvent is ethyl acetate.

11. The method as claimed in claim 1 , wherein the step (d) comprises the following steps:

(d1) neutralizing the reaction solution;

(d2) filtrating and concentrating the reaction solution; and

(d3) purifying the reaction solution by column chromatography.

12. A method for producing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene comprising the following steps:

(a) mixing Br 2 , 1,4-bis(difluoromethyl)tetrafluorobenzene, and a solvent to form a reaction solution;

(b) heating the reaction solution under UV irradiation until the temperature thereof is raised to the range of 100 to 200°; and

(c) purifying the reaction solution to afford 1,4-bis(bromodifluoromethyl) tetra-fluorobenzene.

13. The method as claimed in claim 12 , wherein additional Br 2 is further added into the reaction solution at a fixed interval of time when the reaction is performed in the step (b).

14. The method as claimed in claim 12 , wherein the reaction time of the step (b) is from 24 to 96 hours.

15. The method as claimed in claim 12 , wherein the reaction solution of the step (b) is heated until it undergoes reflux.

16. The method as claimed in claim 12 , wherein the reaction temperature of the step (b) is from 110 to 180°.

17. The method as claimed in claim 12 , wherein the molar ratio of Br 2 to 1,4-bis(difluoromethy)tetrafluorobenzene is more than 2:1.

18. The method as claimed in claim 12 , wherein the solvent is a halogen aliphatics or a halogen aromatics.

19. The method as claimed in claim 18 , wherein the solvent is at least one selected from the group consisting of chloropentafluorobenzene (C 6 F 5 Cl), bromo -pentafluorobenzene (C 6 F 5 Br), o-dichlorobenzene (o-C 6 H 4 Cl 2 ), and bromotrichloro -methane (CBrCl 3 ).

20. The method as claimed in claim 12 , wherein the step (c) comprises the following steps:

(c11) neutralizing the reaction solution;

(c12) filtrating and concentrating the reaction solution; and

(c13) purifying the reaction solution by column chromatography.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2016
From: YUAN-SHIN MATERIALS TECHNOLOGY CORP.; NATIONAL CHUNG-SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY
To: NATIONAL CHUNG-SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY
Reel/Frame 039800/0194 →
CHANGE OF NAME Recorded Apr 17, 2015
From: CHUNG-SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY, ARMAMENTS, BUREAU, MINISTRY OF NATIONAL DEFENSE
To: NATIONAL CHUNG SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY
Reel/Frame 035453/0379 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2008
From: CHOU, CHUAN-YU; CHANG, PO-CHEN; LIN, CHUN-HSU; WANG, SHIEH-JUN
To: YUAN-SHIN MATERIALS TECHNOLOGY CORP.; CHUNG-SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY ARMAMENTS BUREAU. M.N.D.
Reel/Frame 021364/0675 →