IP Library › Granted Patent US 11,401,398
Granted Patent B2
US 11,401,398 · App. 17/024,159 · Granted Aug 2, 2022

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 11,401,398
App. No.
17/024,159
Granted
Aug 2, 2022
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 (25)

1. A process for depolymerization of polyethylene terephthalate (PET) to form a terephthalate; the process comprising admixing polyethylene terephthalate (PET), sodium glycoxide, and at least one solvent comprising at least one of water, alcohol, or glycol.

2. The process of claim 1 , wherein the at least one solvent is selected from methanol, ethanol, n-propanol, isopropanol, t-butanol, ethylene glycol, glycerol, cyclohexane-1,4-dimethanol, phenol, benzyl alcohol, and any combinations thereof.

3. The process of claim 1 , wherein the alcohol is methanol, ethanol, propanol, butanol, or a combination thereof.

4. The process of claim 1 , wherein the at least one solvent is added to the polyethylene terephthalate (PET) prior to the addition of the sodium glycoxide.

5. The process of claim 4 , wherein the polyethylene terephthalate (PET) is mixed with the at least one solvent prior to the addition of the sodium glycoxide for about 15 mins to about 120 mins.

6. The process of claim 1 , wherein the polyethylene terephthalate (PET) is mixed with the at least one solvent prior to the addition of the sodium glycoxide at a temperature between 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 sodium glycoxide is mono sodium glycoxide and the mono sodium glycoxide is provided as a suspension.

9. The process of claim 8 , 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.

10. The process of claim 9 , wherein step (a) is performed at a temperature between about 70° C. to about 100° C.

11. The process of claim 9 , wherein the ratio of mono sodium glycoxide to the suspending solvent is between about 0.05:1 to about 0.5:1 (mol/mol).

12. The process of claim 9 , wherein the suspending solvent is methanol.

13. The process of claim 9 , wherein the suspension is aged for about 1-14 days.

14. The process of claim 1 , wherein the ratio of the sodium glycoxide to polyethylene terephthalate (PET) is between about 1:2 and about 1:20 (mol/mol).

15. The process of claim 1 , wherein the ratio of the sodium glycoxide to polyethylene terephthalate (PET) is between about 1:5 and about 1:20 (mol/mol).

16. The process of claim 1 , wherein the ratio of the sodium glycoxide to polyethylene terephthalate (PET) is between about 1:10 and about 1:20 (mol/mol).

17. The process of claim 1 , wherein the ratio of the sodium glycoxide to polyethylene terephthalate (PET) is between about 1:10 and about 1:15 (mol/mol).

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

19. The process of claim 1 , wherein the process further yields mono ethylene glycol.

20. The process of claim 19 , wherein the mono ethylene glycol is obtained in at least about 80 mol % yield.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2020
From: ESSADDAM, ADEL; ESSADDAM, FARES
To: 9449710 CANADA INC.
Reel/Frame 054196/0042 →
Continuity (3)
Continuation 16450807 · Jun 24, 2019
Provisional Application 62689597 · Jun 25, 2018
Related Publication 20210079192A1 · Mar 18, 2021
Cited By (1)
US 12,415,901