IP Library Granted Patent US 12,600,697
Granted Patent B2
US 12,600,697 · App. 18/562,589 · Granted Apr 14, 2026

Compositions and methods for removal of n-methyl-2-pyrrolidone (NMP) degradation products and other foulants from NMP purification systems

Inventors: Jerrod Overholt (San Pedro, CA); Sean E. Sears (The Woodlands, TX)
Assignee: Refined Technologies, Inc.
C07D201/16B01D3/14C07D207/267
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Quick Facts
Patent No.
US 12,600,697
App. No.
18/562,589
Granted
Apr 14, 2026
Kind
B2
Abstract

Methods of cleaning an N-methyl-2-pyrrolidone (NMP) purification and recovery system having an NMP-containing chemical waste stream, a separation tower fluidically coupled with the chemical waste stream, a reflux drum fluidically coupled with an upper section of the separation tower, a reboiler fluidically coupled with a lower section of the separation tower, and a purified NMP stream fluidically coupled with the reboiler. The methods include injecting a cleaning solution into the reflux drum and the reboiler with an amount of the cleaning solution sufficient to at least substantially fill the reflux drum and the reboiler, the cleaning solution comprising a solvent having a primary amine and a hydroxyl group, circulating the cleaning solution through at least the separation tower, the reflux drum, the reboiler for a period of time to solubilize foulants contained within the system, and draining the cleaning solution having foulants solubilized therein from the system.

Claims (24)

1 . A method of cleaning an N-methyl-2-pyrrolidone (NMP) purification and recovery system, the system comprising:

an NMP-containing chemical waste stream;

a separation tower fluidically coupled with the chemical waste stream;

a reflux drum fluidically coupled with an upper section of the separation tower;

a reboiler fluidically coupled with a lower section of the separation tower; and

a purified NMP stream fluidically coupled with the reboiler;

the method comprising:

injecting a cleaning solution into the reflux drum and the reboiler with an amount of the cleaning solution sufficient to at least substantially fill the reflux drum and the reboiler, the cleaning solution comprising a solvent having a primary amine and a hydroxyl group;

circulating the cleaning solution through at least the separation tower, the reflux drum, and the reboiler for a period of time to solubilize foulants contained within the system; and

draining the cleaning solution having foulants solubilized therein from the system.

2 . The method of claim 1 , further comprising injecting the cleaning solution into the reflux drum and the reboiler with an amount of the cleaning solution sufficient to at least substantially fill a lower portion of the separation tower.

3 . The method of claim 1 , wherein circulating the cleaning solution is facilitated by a bottoms pump fluidically coupled with the lower section of the separation tower and the reboiler and an overhead pump fluidically coupled with the section of the separation tower and the reflux drum.

4 . The method of claim 1 , wherein a vapor return from the reboiler to the lower section of the separation tower is at ambient temperature prior to injecting the cleaning solution.

5 . The method of claim 1 , wherein a vapor return from the reboiler to the lower section of the separation tower is at an operating temperature of between about 38° C. and about 55° C. prior to injecting the cleaning solution.

6 . The method of claim 1 , wherein a vapor return from the reboiler to the lower section of the separation tower is at an operating temperature of between ambient temperature and about 55° C. prior to injecting the cleaning solution.

7 . The method of claim 1 , wherein a vapor return from the reboiler to the lower section of the separation tower is at an operating temperature of between about 38° C. and about 55° C. during circulation of the cleaning solution.

8 . The method of claim 1 , wherein the solvent is a glycolamine.

9 . The method of claim 1 , wherein the solvent is diglycolamine.

10 . The method of claim 1 , wherein the solvent is one or more of (2-aminoethoxy)ethanol, 2-[2-(2-aminoethoxy)ethoxy]ethanol, 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethanol, 2-(2-amino-1-methylethoxy)ethanol, 2-[(3-aminopropyl)(ethyl)amino]ethanol, 2-(2-aminoethylamino)ethanol, 3-[(2-aminoethyl)amino]-1-propanol, and 2-(2-amino-1,1-dimethyl-ethylamino)ethanol.

11 . The method of claim 1 , wherein the cleaning solution has a solvent-to-water volumetric ratio ranging from about 50:50 to about 100:0.

12 . The method of claim 1 , wherein the cleaning solution has a water-to-solvent volumetric ratio ranging from about 80:20 to about 50.1:49.9.

13 . The method of claim 1 , wherein the period of time ranges from about 30 minutes to about 4 hours.

14 . The method of claim 1 , wherein the period of time ranges from about 1 hour to about 3 hours.

15 . The method of claim 1 , wherein the period of time is about 2 hours.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 20, 2023
From: OVERHOLT, JERROD; SEARS, SEAN E.
To: REFINED TECHNOLOGIES, INC.
Reel/Frame 065620/0909 →
Continuity (2)
Provisional Application 63193438 · May 26, 2021
Related Publication 20240132446A1 · Apr 25, 2024
References Cited (4)
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US 20120241307A1 · Miyata et al. · 2012 [cited by applicant]
US 20130210692A1 · Gutowski et al. · 2013 [cited by applicant]
International Search Report mailed Oct. 5, 2022 and issued in PCT counterpart application No. PCT/US2022/030878. 12 pages. [cited by applicant]