IP Library Granted Patent US 11,945,764
Granted Patent B2
US 11,945,764 · App. 17/835,028 · Granted Apr 2, 2024

Efficient synthesis of diglycolamide molecules

Inventors: Santa Jansone-Popova (Knoxville, TN); Ilja Popovs (Knoxville, TN)
Assignee: UT-Battelle, LLC
C07C231/02C07D207/12C07D211/40
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 11,945,764
App. No.
17/835,028
Granted
Apr 2, 2024
Kind
B2
Abstract

A method for producing a diglycolamide molecule having the formula: wherein R 1 and R 2 are independently selected from alkyl groups (R) and acyl groups (C(O)R) in which the alkyl groups (R) contain 1-30 carbon atoms and optionally contain an ether or thioether linkage between carbon atoms, and R 5 and R 6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and one or both pairs of R 1 and R 2 are optionally interconnected to form a ring; the method comprising: combining a diglycolic acid molecule (A) and a secondary amine (B) to form a salt intermediate (C), and heating the salt intermediate (C) to a temperature of 100° C. to 300° C. to form the diglycolamide of Formula (1) in a dehydration process, wherein the method is shown schematically as follows:

Claims (10)

1. A method for producing a diglycolamide molecule having the formula:

wherein R 1 and R 2 are independently selected from alkyl groups (R) and acyl groups (C(O)R) in which the alkyl groups (R) contain 1-30 carbon atoms and optionally contain an ether or thioether linkage between carbon atoms, and R 5 and R 6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and one or both pairs of R 1 and R 2 are optionally interconnected to form a ring;

the method comprising: combining a diglycolic acid molecule (A) and a secondary amine (B) to form a salt intermediate (C), and heating the salt intermediate (C) to a temperature of 100° C. to 300° C. to form the diglycolamide of Formula (1) in a dehydration process, wherein the method is shown schematically as follows:

2. The method of claim 1 , wherein R 5 and R 6 are hydrogen atoms.

3. The method of claim 1 , wherein R 5 and R 6 are methyl groups.

4. The method of claim 1 , wherein R 1 and R 2 are the same.

5. The method of claim 1 , wherein R 1 and R 2 are different.

6. The method of claim 5 , wherein R 1 contains 1-3 carbon atoms and R 2 contains 4-30 carbon atoms.

7. The method of claim 1 , wherein (A) and (B) are combined with a solvent having a boiling point of at least 100° C.

8. The method of claim 1 , wherein (A) and (B) are ball milled in the absence of a solvent.

Assignments (2)
CONFIRMATORY LICENSE Recorded Aug 24, 2022
From: UT-BATTELLE, LLC
To: U. S. DEPARTMENT OF ENERGY
Reel/Frame 060880/0474 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2022
From: JANSONE-POPOVA, SANTA; POPOVS, ILJA
To: UT-BATTELLE, LLC
Reel/Frame 060137/0221 →
Continuity (2)
Provisional Application 63208591 · Jun 9, 2021
Related Publication 20230002311A1 · Jan 5, 2023