IP Library Granted Patent US 11,827,599
Granted Patent B1
US 11,827,599 · App. 17/983,873 · Granted Nov 28, 2023

Method of preparing ionic fluids

Inventor: Arthur G. Mack (Conroe, TX)
Assignee: TETRA Technologies, Inc.
C07D207/04
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Quick Facts
Patent No.
US 11,827,599
App. No.
17/983,873
Granted
Nov 28, 2023
Kind
B1
Abstract

A method of preparing MEP including the steps of: (a) adding N-methylpyrrolidine to an excess amount of ethyl bromide located in a reactor, wherein the N-methylpyrrolidine will react with the ethyl bromide forming MEP, wherein the reaction will have a reaction temperature that can varies over time; (b) stopping addition of N-methylpyrrolidine when the excess of ethyl bromide to the N-methylpyrrolidine falls within a range of 3:1 to 1.5:1; (c) adding water to the reactor creating a two phase system to develop which includes: (i) a top layer containing aqueous MEP and (ii) a bottom layer containing ethyl bromide; (d) separating the top layer from the bottom layer yielding a first aqueous solution of MEP and a second solution of ethyl bromide; and (e) removing N-methylpyrrolidine and ethyl bromide from the first aqueous solution of MEP.

Claims (27)

1. A method of preparing MEP comprising the steps of:

(a) adding N-methylpyrrolidine to an excess amount of ethyl bromide located in a reactor, wherein the N-methylpyrrolidine will react with the ethyl bromide forming MEP, wherein the reaction will have a reaction temperature that can varies over time;

(b) stopping addition of N-methylpyrrolidine when the excess of ethyl bromide to the N-methylpyrrolidine falls within a range of 3:1 to 1.5:1;

(c) adding water to the reactor creating a two phase system to develop which includes: (i) a top layer containing aqueous MEP and (ii) a bottom layer containing ethyl bromide;

(d) separating the top layer from the bottom layer yielding a first aqueous solution of MEP and a second solution of ethyl bromide; and

(e) removing N-methylpyrrolidine and ethyl bromide from the first aqueous solution of MEP.

2. The method of preparing MEP of claim 1 , wherein during step “a” the reaction temperature is maintained lower than 50° C.

3. The method of preparing MEP of claim 1 , wherein step “b” occurs when the excess of ethyl bromide to the N-methylpyrrolidine falls within a range of 3:1 to 1.85:1.

4. The method of preparing MEP of claim 1 , wherein step “b” occurs when the excess of ethyl bromide to the N-methylpyrrolidine falls within a range of 2:1 to 1.85:1.

5. The method of preparing MEP of claim 1 , wherein during step “b” the excess of ethyl bromide to the N-methylpyrrolidine is of 3:1 to 2:1.

6. The method of preparing MEP of claim 1 , wherein and a slurry of MEP is formed in the excess of ethyl bromide in step “b”, and the slurry of MEP and excess ethyl bromide is allowed to cool to 25° C. between steps “b” and “c”.

7. The method of preparing MEP of claim 1 , wherein in step “c” the water is purified water.

8. The method of preparing MEP of claim 7 , wherein the purified water is selected from the group consisting of de-ionized water, reverse osmosis water, and distilled water.

9. The method of preparing MEP of claim 1 , wherein step “d” is performed using a phase cut.

10. The method of preparing MEP of claim 1 , wherein step “e” sparging with a noble gas is used for removal of N-methylpyrrolidine and ethyl bromide.

11. The method of preparing MEP of claim 10 , wherein N2 is the noble gas.

12. The method of preparing MEP of claim 1 , wherein step “e” sparging with a gas is used for removal of N-methylpyrrolidine and ethyl bromide, wherein said gas is non-reactive relative to MEP, N-methylpyrrolidine, and ethyl bromide.

13. The method of preparing MEP of claim 12 , wherein the sparging is performed at a temperature of between 30° C. and 50° C.

14. The method of preparing MEP of claim 12 , wherein at the end of step “e” the pH is between 6 and 9.

15. The method of preparing MEP of claim 12 , wherein at the end of step “e” the pH is between 6 and 9 due to ethyl bromide.

16. The method of preparing MEP of claim 1 , wherein in step “a”, the reactor is selected from the group consisting of a container, a tank, a vessel, a pressure vessel, a pipe, a conduit, and a flask.

17. The method of preparing MEP of claim 1 , wherein in step “a”, the reactor is insulated.

18. The method of preparing MEP of claim 1 , wherein in step “a”, the reactor is a jacketed vessel.

19. The method of preparing MEP of claim 1 , wherein in step “e”, N-methylpyrrolidine is removed until its concentration in the first aqueous solution of MEP is less than 2000 parts per million.

20. The method of preparing MEP of claim 19 , wherein in step “e”, N-methylpyrrolidine is removed until its concentration in the first aqueous solution of MEP is not detectable.

21. The method of preparing MEP of claim 1 , wherein in step “e”, ethyl bromide is removed until only trace amounts of ethyl bromide remain in the first aqueous solution of MEP.

22. The method of preparing MEP of claim 21 , wherein in step “e”, ethyl bromide is removed until its concentration in the first aqueous solution of MEP is not detectable.

Assignments (3)
SECURITY INTEREST Recorded May 16, 2024
From: TETRA TECHNOLOGIES, INC.
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 067435/0204 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jan 12, 2024
From: TETRA TECHNOLOGIES, INC.
To: SILVER POINT FINANCE, LLC
Reel/Frame 066295/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2022
From: MACK, ARTHUR G.
To: TETRA TECHNOLOGIES, INC.
Reel/Frame 061788/0854 →