IP Library › Granted Patent US 12,540,111
Granted Patent B2
US 12,540,111 · App. 18/018,395 · Granted Feb 3, 2026

Method for preparing perfluorodialkyl ether and apparatus for preparing perfluorodialkyl ether

Inventors: Sang Goo Lee (Daejeon, KR); In Joon Park (Daejeon, KR); Won Wook So (Daejeon, KR); Shin Hong Yook (Daejeon, KR); Hong Suk Kang (Daejeon, KR); Eun Ho Sohn (Daejeon, KR); Ki Dong Song (Changwon-si, KR); Yeon Ho Oh (Changwon-si, KR); Hyun Jae Jang (Gimhae-si, KR)
Assignees: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; ELECTROTECHNOLOGY RESEARCH INSTITUTE
C07C41/18C07C41/42C07C43/12
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 12,540,111
App. No.
18/018,395
Granted
Feb 3, 2026
Kind
B2
Abstract

The present invention relates to a method for preparing a perfluorodialkyl ether, comprising the steps of: (A) preparing a perfluorodialkyl ether from a compound represented by Formula 1 in the presence of a metal fluoride; and (B) isolating the perfluorodialkyl ether, and to an apparatus for preparing perfluorodialkyl ether, comprising: a reactor for preparing a perfluorodialkyl ether from a compound represented by Formula 1 in the presence of a metal fluoride; a reactant supplier for introducing the compound represented by Formula 1 into the reactor; and a discharge unit for discharging the perfluorodialkyl ether from the upper portion of the reactor.

Claims (20)

1 . A method for preparing a perfluorodialkyl ether comprising the steps of:

(A) preparing a perfluorodialkyl ether from a compound represented by Formula 1 below in a presence of a metal fluoride as a Lewis acid; and

(B) isolating the perfluorodialkyl ether:

in Formula 1, n is an integer from 1 to 3.

2 . The method of claim 1 , wherein the step (B) is performed after the step (A) is finished.

3 . The method of claim 2 , wherein a cycle including the steps (A) and (B) is repeatedly performed a plurality of times,

the method further comprises, between the respective cycles, the step of additionally introducing a compound represented by Formula 1 below:

in Formula 1, n is an integer from 1 to 3.

4 . The method of claim 1 , wherein in the step (A), the compound represented by Formula 1 is continuously supplied from an outside,

the perfluorodialkyl ether isolated in the step (B) is continuously discharged to the outside.

5 . The method of claim 1 , wherein the step (B) is to isolate the perfluorodialkyl ether by gas-liquid isolation.

6 . The method of claim 1 , wherein the perfluorodialkyl ether is represented by Formula 2 below:

C n F 2n+1 —O—CF 2 —CF 3   [Formula 2]

in Formula 2, n is an integer from 1 to 3.

7 . The method of claim 1 , wherein the metal fluoride includes at least one selected from the group consisting of antimony pentafluoride, aluminum trifluoride, cobalt trifluoride and a combination thereof.

8 . The method of claim 2 , wherein in the step (A), the compound represented by Formula 1 and the metal fluoride are mixed in a molar ratio of 1:0.1 to 1:10.

9 . The method of claim 4 , wherein in the step (A), the compound represented by Formula 1 is continuously supplied from the outside at a flow rate of 0.5 parts by weight/min to 5 parts by weight/min based on 100 parts by weight of the metal fluoride.

10 . The method of claim 2 , wherein the step (A) is performed at −20° C. to 10° C.

11 . The method of claim 4 , wherein the step (A) is performed at −15° C. to 10° C.

12 . The method of claim 4 , wherein in the steps (A) and (B), an internal pressure is controlled to 0.2 bar or more as a gauge pressure.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2023
From: LEE, SANG GOO; PARK, IN JOON; SO, WON WOOK; YOOK, SHIN HONG; KANG, HONG SUK; SOHN, EUN HO; SONG, KI DONG; OH, YEON HO; JANG, HYUN JAE
To: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KOREA ELECTROTECHNOLOGY RESEARCH INSTITUTE
Reel/Frame 062516/0144 →
Priority Claims (2)
KR 10-2020-0094086 · Jul 28, 2020 · national
KR 10-2020-0094087 · Jul 28, 2020 · national
Continuity (1)
Related Publication 20230278944A1 · Sep 7, 2023
References Cited (17)
US 5331066A · Takanoo · 1994 [cited by examiner]
US 6225511B1 · Chambers et al. · 2001 [cited by applicant]
US 10301236B2 · Sun et al. · 2019 [cited by applicant]
US 20030135067A1 · Okazoe et al. · 2003 [cited by applicant]
US 20160185719A1 · Monzani et al. · 2016 [cited by applicant]
CN 111116347A · 2020 [cited by examiner]
KR 1020030038654A · 2003 [cited by applicant]
KR 1020080089339A · 2008 [cited by applicant]
KR 1020180000720A · 2018 [cited by applicant]
WO 2007053697A2 · 2007 [cited by applicant]
Machine translation of CN111116347A, May 8, 2020, pp. 1-5 (Year: 2020). [cited by examiner]
Hudlicky, T. et al. “Practical preparation of potentially anesthetic fluorinated ethyl methyl ethers by means of bromine trifluoride and other methods” Journal of Fluorine Chemistry (2000), 102(1-2), 363-367 (Year: 2000… [cited by examiner]
A. P. Molchanov et al., “Product Subclass 2: 1-Halo-1-(organooxy)alk-1-enes”, Science of Synthesis, pp. 129-166. [cited by applicant]
Takashi Abe et al., “The electrochemical fluorination of N-containing carboxylic acids (Part 4*). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-diallqlamino-n-butyrates”, Journal of Fluorine Chemistry,… [cited by applicant]
Ripudaman Malhotra et al., “George Andrew Olah Across Conventional Lines”, Resonance, Dec. 2017, pp. 1111-1153. [cited by applicant]
Akira Sekiya et al., “Synthesis of Perfluoroethylmethylether by Direct Fluorination”, Chemistry Letters, 1990, pp. 609-612. [cited by applicant]
International Search Report of PCT/KR2021/009664 dated Nov. 1, 2021 [PCT/ISA/210]. [cited by applicant]