Efficient synthesis of diglycolamide molecules

Patent metadata

Field	Value
Publication number	US-11945764-B2
Application number	US-202217835028-A
Country	US
Kind code	B2
Filing date	Jun 8, 2022
Priority date	Jun 9, 2021
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

A method for producing a diglycolamide molecule having the formula:wherein R1 and R2 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 R5 and R6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and one or both pairs of R1 and R2 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:

First claim

What is claimed is:

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.

Assignees

• Ut Battelle Llc

Inventors

• Jansone-Popova Santa
• Popovs Ilja

Classifications

• C07C231/02 Primary

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07D207/12

  Oxygen or sulfur atoms · CPC title

• C07D211/40

  Oxygen atoms · CPC title

• C07D211/74 Primary

  Oxygen atoms · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title