IP Library Granted Patent US 11,192,836
Granted Patent B2
US 11,192,836 · App. 16/770,115 · Granted Dec 7, 2021

Method and apparatus for producing fluorine-containing organic compound

Inventors: Yohsuke Fukuchi (Tokyo, JP); Shinichi Yorozuya (Tokyo, JP); Nozomi Kusumoto (Tokyo, JP); Hiroshi Kobayashi (Tokyo, JP)
Assignee: SHOWA DENKO K.K.
C07C17/10B01J4/02B01J10/00B01J19/0006C07C67/287B01J2219/00186
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Quick Facts
Patent No.
US 11,192,836
App. No.
16/770,115
Granted
Dec 7, 2021
Kind
B2
Abstract

Provided is a method for producing a fluorine-containing organic compound. The method can immediately detect the occurrence of a side reaction in direct fluorination reaction using fluorine gas and can give a highly pure fluorine-containing organic compound at a high yield. A raw material liquid ( 1 ) containing a raw material organic compound having a hydrogen atom and two or more carbon atoms is reacted with fluorine gas in a reaction container ( 11 ) to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give a fluorine-containing organic compound. In the reaction, tetrafluoromethane contained in a gas phase ( 2 ) in the reaction container ( 11 ) is continuously measured, and the amount of the fluorine gas supplied to the reaction container ( 11 ) is controlled depending on the measured value of the tetrafluoromethane.

Claims (7)

1. A method for producing a fluorine-containing organic compound, the method comprising:

reacting a raw material liquid containing a raw material organic compound having a hydrogen atom and two or more carbon atoms with fluorine gas in a reaction container to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give the fluorine-containing organic compound,

wherein tetrafluoromethane contained in a gas phase in the reaction container is continuously measured, and an amount of the fluorine gas supplied to the reaction container is controlled depending on a measured value of the tetrafluoromethane,

wherein the raw material organic compound is 1,2,3,4-tetrachlorobutane, and the fluorine-containing organic compound is 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane.

2. The method for producing the fluorine-containing organic compound according to claim 1 , wherein the gas phase in the reaction container is introduced to an infrared spectrometer to measure the tetrafluoromethane.

3. The method for producing the fluorine-containing organic compound according to claim 2 , wherein the infrared spectrometer is used to measure peaks around wavelengths of 798 cm −1 , 1240 cm −1 , 1290 cm −1 , 1540 cm −1 , and 2200 cm −1 .

4. The method for producing the fluorine-containing organic compound according to claim 2 , wherein when the peak around a wavelength of 1290 cm −1 measured with the infrared spectrometer has an intensity exceeding a predetermined intensity, the amount of the fluorine gas supplied is reduced, or the supply of the fluorine gas is stopped.

Assignments (3)
CHANGE OF ADDRESS Recorded Feb 14, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066599/0037 →
CHANGE OF NAME Recorded Jun 23, 2023
From: SHOWA DENKO K.K.
To: RESONAC CORPORATION
Reel/Frame 064082/0513 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2020
From: FUKUCHI, YOHSUKE; YOROZUYA, SHINICHI; KUSUMOTO, NOZOMI; KOBAYASHI, HIROSHI
To: SHOWA DENKO K.K.
Reel/Frame 052848/0091 →