IP Library › Granted Patent US 12,071,520
Granted Patent B2
US 12,071,520 · App. 17/837,801 · Granted Aug 27, 2024

Terephthalic acid esters formation

Inventors: Adel Essaddam (Terrebonne, CA); Fares Essaddam (Terrebonne, CA)
Assignee: 9449710 CANADA INC.
C08J11/22C07C31/30C07C67/03C07C69/82C08J11/24C07C29/132C08J2367/02
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Quick Facts
Patent No.
US 12,071,520
App. No.
17/837,801
Granted
Aug 27, 2024
Kind
B2
Abstract

The present disclosure relates to the formation of dimethyl terephthalate (DMT). The present invention also relates to the depolymerization of polyethylene terephthalate (PET) and the recovery of dimethyl terephthalate (DMT).

Claims (28)

1. A process for depolymerization of a polyester to form a terephthalate; the process comprising admixing the polyester, a glycoxide, and at least one solvent comprising methanol.

2. The process of claim 1 , wherein the polyester is selected from polyethylene terephthalate (PET), poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate) (PETG), polyglycolide or polyglycolic acid (PGA), polylactic acid (PLA), polycaprolactone (PCL), polyhydroxybutyrate (PHB), polyethylene adipate (PEA), polybutylene succinate (PBS), poly(3-hydroxy butyrate-co-3-hydroxyvalerate) (PHBV), polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polyethylene naphthalate (PEN), cutin, or any combinations thereof.

3. The process of claim 1 , wherein the terephthalate is obtained in at least about 90 mol % yield.

4. The process of claim 1 , wherein the at least one solvent is added to the polyester prior to the addition of the glycoxide.

5. The process of claim 4 , wherein the polyester is mixed with the at least one solvent prior to the addition of the glycoxide for about 15 mins to about 120 mins.

6. The process of claim 1 , wherein the polyester is mixed with the at least one solvent prior to the addition of the glycoxide at a temperature from about 50° C. to about 100° C.

7. The process of claim 1 , wherein the terephthalate is dimethyl terephthalate (DMT).

8. The process of claim 1 , wherein the glycoxide is sodium glycoxide.

9. The process of claim 8 , wherein the sodium glycoxide is mono sodium glycoxide.

10. The process of claim 9 , wherein the mono sodium glycoxide is provided as a suspension.

11. The process of claim 10 , wherein the mono sodium glycoxide suspension is prepared by a process comprising:

a) heating mono ethylene glycol;

b) adding sodium hydroxide thereby forming mono sodium glycoxide;

c) drying the mono sodium glycoxide;

d) suspending the dried mono sodium glycoxide into a suspending solvent; and

e) aging the suspension.

12. The process of claim 11 , wherein step (a) is performed at a temperature from about 70° C. to about 100° C.

13. The process of claim 12 , wherein a ratio of mono sodium glycoxide to the suspending solvent is from about 0.05:1 to about 0.5:1 (mol/mol).

14. The process of claim 13 , wherein the suspending solvent is methanol.

15. The process of claim 1 , wherein a ratio of the glycoxide to the polyester is from about 1:2 to about 1:20 (mol/mol).

16. The process of claim 1 , wherein a ratio of the glycoxide to the polyester is from about 1:5 to about 1:20 (mol/mol).

17. The process of claim 1 , wherein a ratio of the glycoxide to the polyester is from about 1:10 to about 1:20 (mol/mol).

18. A process for preparing a mono sodium glycoxide suspension; the process comprising:

a) heating mono ethylene glycol;

b) adding sodium hydroxide thereby forming mono sodium glycoxide;

c) drying the mono sodium glycoxide;

d) suspending the dried mono sodium glycoxide into a suspending solvent; and

e) aging the suspension.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2023
From: ESSADDAM, ADEL; ESSADDAM, FARES
To: 9449710 CANADA INC.
Reel/Frame 062672/0577 →
Continuity (4)
Continuation 17024159 · Sep 17, 2020
Continuation 16450807 · Jun 24, 2019
Provisional Application 62689597 · Jun 25, 2018
Related Publication 20230125080A1 · Apr 27, 2023