US2020392067A1PendingUtilityA1

Terephthalic acid esters formation

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Assignee: 9449710 CANADA INCPriority: Sep 15, 2017Filed: Aug 27, 2020Published: Dec 17, 2020
Est. expirySep 15, 2037(~11.1 yrs left)· nominal 20-yr term from priority
Inventors:Adel EssaddamFares Essaddam
Y02W30/62C08J 2367/03C08J 11/24C07C 31/202C07C 29/1285C07C 67/08C08F 8/50C08J 7/02C08L 67/03C07C 51/09C08K 5/05C08J 11/26C08L 101/00C07C 67/03C07C 29/095C07C 69/82C08J 11/22C08J 2367/02
68
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Claims

Abstract

The present disclosure relates to the formation of terephthalate esters. The present invention also relates to the depolymerization of polyethylene terephthalate (PET) or poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate) and the recovery of terephthalate esters

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A process for the transformation of a polyester selected from polyethylene terephthalate and poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate) into a terephthalate of Formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  hydroxyalkyl, optionally substituted C 3 -C 8  cycloalkyl, optionally substituted (C 1 -C 6  alkyl)(C 3 -C 8  cycloalkyl), optionally substituted aryl, and optionally substituted (C 1 -C 6  alkyl)(aryl); provided that one of R 1  or R 2  is not hydrogen; 
         the process comprising admixing the polyester with a mixture comprising:
 (a) a solvent for swelling the polyester; 
 (b) an alcoholic solvent; and 
 (c) a sub-stoichiometric amount of an alkoxide. 
 
       
     
     
         2 . The process of  claim 1 , wherein R 1  or R 2  is methyl. 
     
     
         3 . The process of  claim 1  or  2 , wherein the alcoholic solvent is selected from methanol, ethanol, n-propanol, isopropanol, t-butanol, ethylene glycol, glycerol, cyclohexane-1,4-diyldimethanol, phenol, benzyl alcohol, and any combinations thereof. 
     
     
         4 . The process of  claim 3 , wherein the alcoholic solvent is methanol. 
     
     
         5 . The process of any one of  claims 1 - 4 , wherein the solvent for swelling the polyester is selected from a non polar solvent, a polar aprotic solvent, a polar protic solvent, and any combinations thereof. 
     
     
         6 . The process of any one of  claims 1 - 5 , wherein the solvent for swelling the polyester is selected from DMSO, DMF, acetone, a halogenated solvent, n-hexane, nitrobenzene, methanol, benzyl alcohol, benzaldehyde, and any combinations thereof. 
     
     
         7 . The process of any one of  claims 1 - 6 , wherein the solvent for swelling the polyester is a halogenated solvent. 
     
     
         8 . The process of any one of  claims 1 - 7 , wherein the ratio of solvent for swelling the polyester to alcoholic solvent is between about 0.1:1 and about 2:1 (w:w). 
     
     
         9 . The process of any one of  claims 1 - 8 , wherein the ratio of solvent for swelling the polyester to alcoholic solvent is between about 0.5:1 and about 1:1 (w:w). 
     
     
         10 . The process of any one of  claims 1 - 9 , wherein the alkoxide is selected from an alkali metal alkoxide, an alkaline earth metal alkoxide, a metal alkoxide, an ammonium alkoxide and any combinations thereof. 
     
     
         11 . The process of any one of  claims 1 - 10 , wherein the alkoxide is generated in-situ by addition of an alkali metal, an alkaline earth metal, or a metal to the alcoholic solvent. 
     
     
         12 . The process of any one of  claims 1 - 11 , wherein the ratio of polyester to alkoxide is between about 15:1 and about 125:1 (w:w). 
     
     
         13 . The process of any one of  claims 1 - 12 , wherein the ratio of polyester to alkoxide is between about 20:1 and about 25:1 (w:w). 
     
     
         14 . The process of any one of  claims 1 - 13 , wherein the admixing of the polyester with the solvent for swelling the polyester, the alkoxide, and the alcoholic solvent is performed until an about 80% yield of the terephthalate of Formula (I) is achieved. 
     
     
         15 . The process of any one of  claims 1 - 14 , wherein the admixing of the polyester with the solvent for swelling the polyester, the alkoxide, and the alcoholic solvent is performed without external heat. 
     
     
         16 . The process of any one of  claims 1 - 15 , wherein the admixing of the polyester with the solvent for swelling the polyester, the alkoxide, and the alcoholic solvent is performed at atmospheric pressure. 
     
     
         17 . A process for the transformation of polyethylene terephthalate into dimethyl terephthalate, comprising admixing the polyethylene terephthalate with a mixture comprising:
 (a) a solvent for swelling the polyethylene terephthalate;   (b) methanol; and   (c) a sub-stoichiometric amount of an alkoxide.   
     
     
         18 . The process of  claim 17 , wherein the solvent for swelling the polyethylene terephthalate is selected from a halogenated solvent, DMSO, benzyl alcohol, methanol, and any combinations thereof. 
     
     
         19 . The process of  claim 17  or  18 , wherein the ratio of polyethylene terephthalate to alkoxide is between about 20:1 and about 25:1 (w:w). 
     
     
         20 . The process of any one of  claims 17 - 19 , wherein the alkoxide is selected from sodium methoxide, potassium ethoxide, aluminium tri-n-propoxide, and tetrabutylammonium methoxide. 
     
     
         21 . The process of any one of  claims 17 - 20 , wherein the ratio of solvent for swelling the polyester to methanol is between about 0.5:1 and about 1:1 (w:w). 
     
     
         22 . The process of any one of  claims 17 - 21 , wherein the admixing of the polyethylene terephthalate with the solvent for swelling the polyethylene terephthalate, the alkoxide, and the methanol is performed until an about 80% yield of dimethyl terephthalate is achieved. 
     
     
         23 . A reaction mixture comprising:
 (a) a polyester selected from polyethylene terephthalate and poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate);   (b) a solvent for swelling the polyester;   (c) an alcoholic solvent; and   (d) a sub-stoichiometric amount of an alkoxide.   
     
     
         24 . The reaction mixture of  claim 23 , wherein the alcoholic solvent is selected from methanol, ethanol, n-propanol, isopropanol, t-butanol, ethylene glycol, glycerol, cyclohexane-1,4-diyldimethanol, phenol, benzyl alcohol, and any combinations thereof. 
     
     
         25 . The reaction mixture of  claim 23  or  24 , wherein the solvent for swelling the polyester is selected from a non polar solvent, a polar aprotic solvent, a polar protic solvent, and any combinations thereof. 
     
     
         26 . The reaction mixture of any one of  claims 23 - 25 , wherein the solvent for swelling the polyester is a halogenated solvent and the alcoholic solvent is methanol. 
     
     
         27 . The reaction mixture of any one of  claims 23 - 26 , wherein the ratio of solvent for swelling the polyester to alcoholic solvent is between about 0.5:1 and about 1:1 (w:w). 
     
     
         28 . The reaction mixture of any one of  claims 23 - 27 , wherein the ratio of polyester to alkoxide is between about 15:1 and about 30:1 (w:w). 
     
     
         29 . The reaction mixture of any one of  claims 23 - 28 , wherein the alkoxide is selected from sodium methoxide, potassium ethoxide, aluminium tri-n-propoxide, and tetrabutylammonium methoxide. 
     
     
         30 . The reaction mixture of any one of  claims 23 - 29 , wherein the alkoxide is sodium methoxide.

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