Compositions and methods of preparation thereof

Patent metadata

Field	Value
Publication number	US-11827591-B2
Application number	US-202117515249-A
Country	US
Kind code	B2
Filing date	Oct 29, 2021
Priority date	Oct 30, 2020
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

Described herein are methods of preparing compounds derived from triglycerides or condensation polymers such as polyesters and/or polyamides. The methods may include subjecting triglyceride or condensation polymer containing matter to mechanical processing in the presence of a nucleophile.

First claim

What is claimed is:

1. A method for depolymerizing polyester-containing compounds into constituent oligomer and/or monomers, the method comprising:
contacting a polyester-containing compound with a nucleophile to form a first mixture, wherein the polyester-containing compound is a triglyceride, and the nucleophile is a hydroxide selected from potassium hydroxide, sodium hydroxide, barium hydroxide, cesium hydroxide, and calcium hydroxide;
mechanically processing the first mixture to decompose at least a portion of the polyester-containing compound to yield a second mixture comprising the constituent oligomer and/or monomers of the polyester-containing compound; and
isolating at least a portion of the constituent oligomer and/or monomers from the second mixture.

2. The method of claim 1 , wherein the mechanical processing comprises grinding the first mixture.

3. The method of claim 2 , wherein grinding the first mixture comprises ball milling.

4. The method of claim 2 , wherein grinding the first mixture comprises planetary ball milling, and the first mixture is milled at a spinning frequency of about 1 rpm to about 1000 rpm.

5. The method of claim 1 , wherein the mechanical processing comprises agitating the first mixture.

6. The method of claim 1 , wherein the mechanical processing reduces the particle size of at least a portion of the second mixture to a mean particle size of less than about 1000 microns.

7. The method of claim 1 , wherein isolating at least a portion of the constituent monomers from the second mixture comprises treating the second mixture with an acid.

8. The method of claim 7 , wherein the acid is an inorganic acid.

9. The method of claim 7 , wherein the acid is selected from hydrochloric acid, phosphoric acid, and sulfuric acid.

10. The method of claim 7 , wherein treating the second mixture with an acid forms a solution having a pH less than or equal to 5.

11. The method of claim 1 , wherein the constituent monomers comprise at least one compound of Formula I:

wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently —H, —OR 13 , —NR 13 R 14 , —SR 13 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 13 , —NR 13 R 14 , —SR 13 , or halogen;
R 13 and R 14 are each independently —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl,
R 12 is —OH, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 13 , —NR 13 R 14 , —SR 13 , halogen, —COOH, or —COOR 11 ;
m, n, and o are each independently an integer in the range of 0 to 30; and
the sum of m, n, and o is 0 to 30.

12. The method of claim 1 , wherein the constituent monomers comprise at least one compound of Formula II:

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently —H, —OR 11 , —NR 11 R 12 , —SR 11 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 11 , —NR 11 R 12 , —SR 11 , or halogen;
R 11 and R 12 are each independently —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;
the symbol represents an optionally single or cis or trans double bond;
R 3 is —OH and R 3′ is selected from —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, and aryl when between R 3 and R 3′ is a single bond, and R 3 and R 3′ are absent when between R 3 and R 3′ represents a double bond;
R 6 is —OH and R 6′ is selected from —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, and —C 6 -C 10 aryl when between R 6 and R 6′ is a single bond, and R 6 and R 6′ are absent when between R 6 and R 6′ represents a double bond;
n is an integer in the range of 0 to 11;
m is an integer in the range of 0 to 25; and
the sum of m and n is 0 to 25.

13. The method of claim 1 , wherein the constituent monomers comprise at least one compound of Formula III:

wherein:
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently, at each occurrence, —H, —OR 14 —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen, wherein:
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle, and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;

R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;
the symbol represents a single bond or a cis or trans double bond;
the symbol represents a cis or trans double bond;
n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;
m is 0, 1, 2, or 3;
q is 0, 1, 2, 3, 4, or 5; and
r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

Assignees

• Apeel Tech Inc

Inventors

• Bakus Ii Ronald C
• Higgins Alena
• Fisher David
• Frazier Charles
• Perez Louis
• Rodriguez Gabriel

Classifications

• C07D201/12

  by depolymerising polyamides · CPC title

• C08J11/10

  by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation (depolymerisation to the original monomer C07) · CPC title

• C07C51/353 Primary

  by isomerisation; by change of size of the carbon skeleton · CPC title

• C08J11/16

  by treatment with inorganic material (C08J11/14 takes precedence) · CPC title

• C11C1/02

  from fats or fatty oils · CPC title