IP Library Granted Patent US 12,415,901
Granted Patent B2
US 12,415,901 · App. 18/461,443 · Granted Sep 16, 2025

Process for the depolymerization of polyethylene terephthalate (PET)

Inventors: Adel Essaddam (Terrebonne, CA); Fares Essaddam (Terrebonne, CA)
Assignee: 9449710 CANADA INC.
C08J11/24C08J2367/02
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Quick Facts
Patent No.
US 12,415,901
App. No.
18/461,443
Granted
Sep 16, 2025
Kind
B2
Abstract

The present disclosure relates to the formation of dimethyl terephthalate (DMT) and mono ethylene glycol (MEG). The present invention also relates to the depolymerization of polyethylene terephthalate (PET) and the recovery of dimethyl terephthalate (DMT) and mono ethylene glycol (MEG) using sodium methoxide as a catalyst.

Claims (24)

1. A process for depolymerizing a polyester to form a terephthalate, the processing comprising:

(i) providing a feedstock comprising the polyester;

ii) mixing the feedstock with a first fraction of an alcohol to form a mixture; and

(iii) subsequent to (ii), mixing a second fraction of the alcohol and a methoxide with the mixture from (ii) to maintain a methoxide concentration in the resulting mixture while forming the terephthalate, the methoxide concentration comprising a sub-stoichiometric amount of methoxide;

wherein the mixing in (ii) is performed at a temperature from about 50° C. to about 100° C., and wherein the mixing in (iii) is performed at a temperature from about 50° C. to about 100° C.

2. The process of claim 1 , wherein the mixing in (ii) is performed at a temperature from about 70° C. to about 100° C.

3. The process of claim 1 , wherein the mixing in (iii) is performed at a temperature from about 70° C. to about 100° C.

4. The process of claim 1 , wherein the mixing in (ii) is performed at a temperature of about 85° C.

5. The process of claim 1 , wherein the mixing in (iii) is performed at a temperature of about 85° C.

6. The process of claim 1 , wherein the terephthalate is obtained in at least 70 mol % yield.

7. The process of claim 6 , wherein the terephthalate is obtained in at least 80 mol % yield.

8. The process of claim 7 , wherein the terephthalate is obtained in at least 90 mol % yield.

9. The process of claim 1 , wherein the alcohol comprises methanol.

10. The process of claim 1 , wherein the alcohol comprises ethanol.

11. The process of claim 1 , wherein the methoxide comprises sodium methoxide.

12. The process of claim 1 , wherein an output mixture comprising the produced terephthalate comprises less than 10 ppm of the methoxide.

13. The process of claim 1 , wherein the polyester comprises polyethylene terephthalate.

14. The process of claim 1 , wherein the polyester comprises polybutylene terephthalate.

15. The process of claim 1 , wherein the polyester comprises polytrimethylene terephthalate.

16. The process of claim 1 , wherein the feedstock comprises a contaminant.

17. The process of claim 16 , wherein the contaminant comprises polyethylene.

18. The process of claim 16 , wherein the contaminant comprises a polyamide.

19. The process of claim 16 , wherein the contaminant comprises a colorant.

20. The process of claim 16 , wherein the contaminant comprises a cellulose.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 15, 2023
From: ESSADDAM, ADEL; ESSADDAM, FARES
To: 9449710 CANADA INC.
Reel/Frame 065572/0447 →
Continuity (4)
Continuation 17529643 · Nov 18, 2021
Continuation 16821870 · Mar 17, 2020
Provisional Application 62821270 · Mar 20, 2019
Related Publication 20240309170A1 · Sep 19, 2024
References Cited (176)
US 2884443A · Erhard et al. · 1959 [cited by applicant]
US 3219622A · Luciano et al. · 1965 [cited by applicant]
US 3321510A · Rudolf et al. · 1967 [cited by applicant]
US 3403115A · Hans et al. · 1968 [cited by applicant]
US 3501420A · Stevenson et al. · 1970 [cited by applicant]
US 3520940A · Smith, Jr. et al. · 1970 [cited by applicant]
US 3776945A · Ligorati et al. · 1973 [cited by applicant]
US 4163860A · Delattre et al. · 1979 [cited by applicant]
US 4230892A · Pruckmayr · 1980 [cited by applicant]
US 4263413A · Gardner et al. · 1981 [cited by applicant]
US 4355175A · Pusztaszeri · 1982 [cited by applicant]
US 4525307A · Pratt · 1985 [cited by applicant]
US 4584414A · Pruckmayr · 1986 [cited by applicant]
US 5045122A · Tindall et al. · 1991 [cited by applicant]
US 5051528A · Naujokas et al. · 1991 [cited by applicant]
US 5236959A · Oakley · 1993 [cited by examiner]
US 5328982A · Tindall et al. · 1994 [cited by applicant]
US 5386055A · Lee et al. · 1995 [cited by applicant]
US 5668186A · Brunelle et al. · 1997 [cited by applicant]
US 5952520A · Naujokas · 1999 [cited by applicant]
US 6528546B2 · Lee et al. · 2003 [cited by applicant]
US 6670503B2 · Broccatelli · 2003 [cited by applicant]
US 6706843B1 · Ishihara et al. · 2004 [cited by applicant]
US 6720448B2 · Broccatelli · 2004 [cited by applicant]
US 6911546B2 · Hedrick et al. · 2005 [cited by applicant]
US 6916936B2 · Hedrick et al. · 2005 [cited by applicant]
US 7053221B2 · Hedrick et al. · 2006 [cited by applicant]
US 7462649B2 · Nakao et al. · 2008 [cited by applicant]
US 7544800B2 · Hedrick et al. · 2009 [cited by applicant]
US 7750057B2 · Ogasawara · 2010 [cited by applicant]
US 7893122B2 · Fregoso-Infante et al. · 2011 [cited by applicant]
US 8309618B2 · Hedrick et al. · 2012 [cited by applicant]
US 8492504B2 · Hedrick et al. · 2013 [cited by applicant]
US 8513379B2 · Matsumura · 2013 [cited by applicant]
US 9550713B1 · Essaddam · 2017 [cited by applicant]
US 10087130B2 · Essaddam · 2018 [cited by applicant]
US 10251976B2 · Erbe et al. · 2019 [cited by applicant]
US 10252976B1 · Essaddam et al. · 2019 [cited by applicant]
US 10640442B2 · Essaddam · 2020 [cited by applicant]
US 10793508B2 · Essaddam et al. · 2020 [cited by applicant]
US 10808096B2 · Essaddam et al. · 2020 [cited by applicant]
US 11248103B2 · Essaddam · 2022 [cited by examiner]
US 11401398B2 · Essaddam et al. · 2022 [cited by applicant]
US 11554366B2 · Essaddam et al. · 2023 [cited by applicant]
US 11795291B2 · Essaddam · 2023 [cited by examiner]
US 11866404B2 · Essaddam et al. · 2024 [cited by applicant]
US 20050027023A1 · Masuda et al. · 2005 [cited by applicant]
US 20080242751A1 · Kurian et al. · 2008 [cited by applicant]
US 20090032015A1 · Myllymaki et al. · 2009 [cited by applicant]
US 20090171113A1 · Anderson et al. · 2009 [cited by applicant]
US 20090318579A1 · Ikenaga · 2009 [cited by applicant]
US 20110004014A1 · Hedrick et al. · 2011 [cited by applicant]
US 20130345453A1 · Sipos et al. · 2013 [cited by applicant]
US 20150315325A1 · Tabor et al. · 2015 [cited by applicant]
US 20160237243A1 · Woldt et al. · 2016 [cited by applicant]
US 20170008826A1 · Essaddam · 2017 [cited by applicant]
US 20170113995A1 · Mastrangelo · 2017 [cited by applicant]
US 20180370984A1 · Morvan et al. · 2018 [cited by applicant]
US 20190084916A1 · Essaddam et al. · 2019 [cited by applicant]
US 20190290035A1 · Nieraad et al. · 2019 [cited by applicant]
US 20190390035A1 · Essaddam et al. · 2019 [cited by applicant]
US 20200157307A1 · Guo · 2020 [cited by applicant]
US 20200392067A1 · Essaddam et al. · 2020 [cited by applicant]
US 20210030960A1 · Huang et al. · 2021 [cited by applicant]
US 20230125080A1 · Essaddam et al. · 2023 [cited by applicant]
US 20230374249A1 · Essaddam et al. · 2023 [cited by applicant]
CA 2069500A1 · 1991 [cited by applicant]
CN 1585798A · 2005 [cited by applicant]
CN 101628909A · 2010 [cited by applicant]
CN 102746460A · 2012 [cited by applicant]
CN 104327254A · 2015 [cited by applicant]
CN 105601507A · 2016 [cited by applicant]
CN 104327254B · 2016 [cited by applicant]
CN 108047023A · 2018 [cited by applicant]
DE 513677C · 1930 [cited by applicant]
EP 1710226A1 · 2006 [cited by applicant]
FR 1081681A · 1954 [cited by applicant]
FR 2335490A1 · 1977 [cited by applicant]
GB 729803A · 1955 [cited by applicant]
GB 784248A · 1957 [cited by applicant]
GB 787554A · 1957 [cited by applicant]
GB 901094A · 1962 [cited by applicant]
GB 1043671A · 1966 [cited by applicant]
GB 2041916A · 1980 [cited by applicant]
JP 48008745A · 1973 [cited by applicant]
JP 50029459B · 1975 [cited by applicant]
JP S61286351A · 1986 [cited by applicant]
JP H0488745A · 1992 [cited by applicant]
JP H051142A · 1993 [cited by applicant]
JP 2000072720A · 2000 [cited by applicant]
JP 2001192492A · 2001 [cited by applicant]
JP 2001261707A · 2001 [cited by applicant]
JP 2003055300A · 2003 [cited by applicant]
JP 2006045371A · 2006 [cited by applicant]
JP 2006052173A · 2006 [cited by applicant]
JP 2008063305A · 2008 [cited by applicant]
JP 4365592B2 · 2009 [cited by applicant]
JP 4575074B2 · 2010 [cited by applicant]
JP 2012116779A · 2012 [cited by applicant]
JP 2012131729A · 2012 [cited by applicant]
JP 2014070132A · 2014 [cited by applicant]
KR 20180092147A · 2018 [cited by applicant]
WO WO9527753A1 · 1995 [cited by applicant]
WO WO9724310A1 · 1997 [cited by applicant]
WO WO9746611A1 · 1997 [cited by applicant]
WO WO9803459A1 · 1998 [cited by applicant]
WO WO0047659A1 · 2000 [cited by applicant]
WO WO0158982A1 · 2001 [cited by applicant]
WO WO0218471A2 · 2002 [cited by applicant]
WO WO0238276A1 · 2002 [cited by applicant]
WO WO2005003217A1 · 2005 [cited by applicant]
WO WO2006021063A1 · 2006 [cited by applicant]
WO WO2007076384A2 · 2007 [cited by applicant]
WO WO2007096326A1 · 2007 [cited by applicant]
WO WO2007113872A1 · 2007 [cited by applicant]
WO WO2007148353A1 · 2007 [cited by applicant]
WO WO2008007384A1 · 2008 [cited by applicant]
WO WO2017007965A1 · 2017 [cited by applicant]
WO WO2019051597A1 · 2019 [cited by applicant]
WO WO2020002999A2 · 2020 [cited by applicant]
WO WO2020188359A1 · 2020 [cited by applicant]
EA202490294 Eurasian Search Report dated Aug. 20, 2024. [cited by applicant]
Karayannidis, G. P. et al. Poly(ethylene terephthalate) Recycling and Recovery of Pure Terephthalic Acid by Alkaline Hydrolysis. Advances in Polymer Technology 21(4):250-259 (2002). [cited by applicant]
Shen, Guo-liang et al. Study on synthesis technology of ethylene glycol sodium by sodium hydroxide method. Chemical Engineer 9:5-6 (2010). (English abstract). [cited by applicant]
ACS. Common Organic Solvents: Table of Properties. downloaded from https://www.organicdivision.org/orig/organic_solvents.html on Apr. 4, 2018, p. 1-2). [cited by applicant]
Adeakin et al. Polymer—Solvent Relation: Swelling and Fibre Morphology. IOSR-JPTE 4(2):27-28 (2017). [cited by applicant]
Al-Sabagh et al. Greener routes for recycling of polyethylene terephthalate. Egyptian Journal of Petroleum 25(1):53-64 (2016). [cited by applicant]
Bae et al., The Characteristics of PET Micro Fiber Fabrics Decomposed dy Sodium Ethylene glycol Solution. Journal of the Korean Home Economics Association 36(8):95-104 (1998) (English Abstract). [cited by applicant]
Balcerzyk. Behavior of swollen poly(ethylene terephthalate) on the action of alkali solutions. Kolloid-Z.u.Z. Polymere 251:776-778 (1973). [cited by applicant]
Cho et al. Hydrophilic treatment of PET [poly(ethylene terephthalate)] fabric with monosodium ethylene glycolate. Journal of the Korean Fiber Society 23(2):80-87 (1986) (English Abstract). [cited by applicant]
Cho et al. Study on Decomposition Reactions of Poly(ethylene terephthalate) Films Treated with Mono-sodium Ethylene Glycolate. Journal of the Korean Society of Dyers and Finishers 2(3):26-35 (1990) (English Abstract). [cited by applicant]
Co-pending U.S. Appl. No. 18/538,336, inventors Essaddam; Adel et al., filed Dec. 13, 2023. [cited by applicant]
Falbe. Alcohols, Aliphatic—Ullmann's Encyclopedia of Industrial Chemistry. Downloaded from https://doi.org/10.1002/14356007.a01_279.pub2, first published Jan. 15, 2013, p. 1-26. [cited by applicant]
Feghali et al. Room Temperature Organocatalyzed Reductive Depolymerization of Waste Polyethers Polyesters and Polycarbonates. ChemSusChem. 8(6):980-984 (2015). [cited by applicant]
Haga. Anomalous Swelling of Poly(ethylene terephthalate) fiber in organic solvents. Journal of Polymer Science, Polymer Letters Edition 20:629-634 (1982). [cited by applicant]
Haga. Case II swelling of poly(ethylene terephthalate) in organic solvents. Journal of Applied Polymer Science 26(8):2649-2655 (1981). [cited by applicant]
Ishalina, O.V., Lakeev, S.N., Minnigulov, R.Z., & Majdanova, I.O. (2015). Analysis of polyethylene terephthalate waste recycling methods. Production and use of elastomers, (3), 39-48 (in Russian). https://cyberleninka.r… [cited by applicant]
Kouzu et al. Heterogeneous catalysis of calcium oxide used for transesterification of soybean oil with refluxing methanol. Applied Catalysis A: General 355:94-99 (2009). [cited by applicant]
Kurokawa et al. Methanolysis of polyethylene terephthalate (PET) in the presence of aluminium tiisopropoxide catalyst to form dimethyl terephthalate and ethylene glycol. Polymer Degradation and Stability 79(3):529-533 (… [cited by applicant]
Liu et al. Calcium methoxide as a solid base catalyst for the transesterification of soybean oil to biodiesel with methanol. Fuel 87:1076-1082 (2008). [cited by applicant]
Mishra et al. Kinetic and thermodynamic study of methanolysis of poly(ethylene terephthalate) waste powder. Polym Int 52:337-342 (2003). [cited by applicant]
Mohsin et al. Sodium Methoxide Catalyzed Depolymerization of Waste Polyethylene Terephthalate Under Microwave Irradiation. Catalysis in Industry 10:41-48 (2018). [cited by applicant]
Mohsin et al. Sodium Methoxide Catalyzed Depolymerization of Waste Polyethylene Terephthalate under Microwave Irradiation. Kataliz V Promyshlennosti 17(4):278-286 (2017). [cited by applicant]
Namboori et al. Steric effects in the basic hydrolysis of poly(ethylene terephthalate). Journal of Applied Polymer Science 12:1999-2005 (1968). [cited by applicant]
PCT/CA2018/051135 International Search Report and Written Opinion dated Dec. 4, 2018. [cited by applicant]
PCT/IB2019/000816 International Search Report and Written Opinion dated Jan. 3, 2020. [cited by applicant]
PCT/IB2020/000216 International Search Report and Written Opinion dated Jun. 25, 2020. [cited by applicant]
PCT/US2016/041392 International Search Report and Written Opinion dated Nov. 10, 2016. [cited by applicant]
Ramsden et al. Factors Influencing the Kinetics of the Alkaline Depolymerisation of Poly(ethylene terephthalate) I: The Effect of Solvent. J Chem Tech Biotechnol 67:131-136 (1996). [cited by applicant]
Sheehan. Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid. Ullmann's Encyclopedia of Industrial Chemistry 36:17-28 (2011). [cited by applicant]
Shukla et al. Glycolysis of polyethylene terephthalate waste fibers. Journal of Applied Polymer Science 98:513-517 (2005). [cited by applicant]
Sullivan et al. Mixed plastics waste valorization through tandem chemical oxidation and biological funneling. Science 378(6616):207-211 (2022). [cited by applicant]
U.S. Appl. No. 14/795,116 Office Action dated Jun. 2, 2016. [cited by applicant]
U.S. Appl. No. 15/377,460 Office Action dated Jan. 29, 2018. [cited by applicant]
U.S. Appl. No. 15/706,484 Office Action dated Apr. 13, 2018. [cited by applicant]
U.S. Appl. No. 15/706,484 Office Action dated Oct. 15, 2018. [cited by applicant]
U.S. Appl. No. 16/117,672 Office Action dated May 15, 2019. [cited by applicant]
U.S. Appl. No. 16/259,980 Office Action dated Feb. 4, 2020. [cited by applicant]
U.S. Appl. No. 16/450,807 Office Action dated Feb. 20, 2020. [cited by applicant]
U.S. Appl. No. 17/024,159 Office Action dated Dec. 1, 2021. [cited by applicant]
U.S. Appl. No. 17/024,159 Office Action dated Jul. 7, 2021. [cited by applicant]
U.S. Appl. No. 17/350,979 Office Action dated Aug. 10, 2022. [cited by applicant]
U.S. Appl. No. 17/350,979 Office Action dated Jan. 25, 2022. [cited by applicant]
U.S. Appl. No. 17/350,979 Office Action dated May 10, 2023. [cited by applicant]
U.S. Appl. No. 17/350,979 Office Action dated Nov. 22, 2022. [cited by applicant]
U.S. Appl. No. 17/350,979 Office Action dated Oct. 21, 2021. [cited by applicant]
U.S. Appl. No. 17/837,801 Notice of Allowance dated Apr. 10, 2024. [cited by applicant]
U.S. Appl. No. 17/837,801 Office Action dated Dec. 21, 2023. [cited by applicant]
U.S. Appl. No. 17/837,801 Office Action dated Jun. 23, 2023. [cited by applicant]
U.S. Appl. No. 18/228,531 Notice of Allowance dated Apr. 18, 2024. [cited by applicant]
U.S. Appl. No. 18/228,531 Office Action dated Jan. 4, 2024. [cited by applicant]
U.S. Appl. No. 18/228,531 Office Action dated Sep. 20, 2023. [cited by applicant]
U.S. Appl. No. 16/821,870 Office Action dated Jul. 26, 2021. [cited by applicant]
U.S. Appl. No. 17/529,643 Office Action dated Nov. 23, 2022. [cited by applicant]
Venkatachalam et al. Materials Science “Polyester”—Chapter 4: Degradation and Recyclability of Poly(Ehtylene Terephthalate). Intech 24 pgs. (2012). [cited by applicant]
Yan. Recycling plastic using a hybrid process. Science 378(6616):132-133 (2022). [cited by applicant]