Process for the Production of Polyester Product from Alkylene Oxide and Carboxylic Acid

Abstract

A process to produce polyester product from alkylene oxide and carboxylic acid. More specifically this process relates to a process to produce polyethylene terephthalate where terephthalic acid and ethylene oxide are reacted to form a partially esterified terephthalic acid product and then the partially esterified product is further reacted with ethylene glycol to produce polyethylene terephthalate.

1 . A process to produce a partially esterified terephthalic acid product said process comprising contacting in a reactor zone terephthalic acid with ethylene oxide in the presence of at least one solvent and at least one basic catalyst to produce said partially esterified terephthalic acid product; 
 wherein said ethylene oxide is present in a molar ratio of about 0.8:1 to 1.2:1 ethylene oxide to terephthalic acid.    
     
     
         2 . The process according to  claim 1 , wherein said reactor zone comprises at least one reactor operated at a pressure such that a substantial portion of the ethylene oxide is in liquid phase.  
     
     
         3 . The process according to  claim 2 , wherein said reactor is operated at a temperature of about 120° C. to about 280° C.  
     
     
         4 . The process according to  claim 2 , wherein said reactor is operated at a temperature of about 180° C. to about 280° C.  
     
     
         5 . The process according to  claim 1 , further comprising reacting said partially esterified terephthalic acid product with a diol to produce polyethylene terephthalate.  
     
     
         6 . The process according to  1 , wherein said basic catalyst is selected from the group consisting of benzyltrialkyl ammonium hydroxide, tributylamine, triethylamine, trimethylamine, tripropyl amine, tetraalkyl ammonium hydroxide and mixtures thereof.  
     
     
         7 . The process according to  claim 1 , wherein said solvent is at least one selected from the group consisting of toluene and xylene.  
     
     
         8 . The process according to  claim 1 , wherein said solvent comprises at least one oligomeric polyester.  
     
     
         9 . A process for the production of a polyester product, said process comprising: 
 (a) contacting in a reaction zone a dicarboxylic acid with an alkylene oxide to produce a partially esterified dicarboxylic acid product, wherein said alkylene oxide and said dicarboxylic acid are present in a molar ratio in the range of from about 0.8:1 to about 1.2:1 alkylene oxide-to-dicarboxylic acid; and    (b) subsequently employing at least a portion of said partially esterified dicarboxylic acid product to produce said polyester product.    
     
     
         10 . The process of  claim 9 , wherein at least a portion of said polyester product is produced in a pipe reactor.  
     
     
         11 . The process of  claim 9 , wherein step (b) further comprises reacting at least a portion of said partially esterified carboxylic acid with a diol to thereby produce said polyester product.  
     
     
         12 . The process of  claim 11 , wherein said diol is an aliphatic diol having in the range of from 2 to 20 carbon atoms.  
     
     
         13 . The process of  claim 12 , wherein said diol comprises ethylene glycol.  
     
     
         14 . The process of  claim 9 , wherein said contacting of step (a) is performed in the presence of at least one solvent and at least one basic catalyst.  
     
     
         15 . The process of  claim 14 , wherein said solvent comprises toluene, xylene, and/or one or more oligomeric polyesters.  
     
     
         16 . The process of  claim 14 , wherein said basic catalyst comprises benzyltrialkyl ammonium hydroxide, tributylamine, triethylemine, trimethylamin, tripropyl amine, and/or tetraalkyl ammonium hydroxide.  
     
     
         17 . The process of  claim 14 , wherein said basic catalyst comprises triethylamine.  
     
     
         18 . The process of  claim 9 , wherein said dicarboxylic acid comprises terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, cyclohexanedicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4′-dicarboxylic acid, diphenyl-3,4′-dicarboxylic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, and/or sebacic acid.  
     
     
         19 . The process of  claim 9 , wherein said dicarboxylic acid comprises terephthalic acid.  
     
     
         20 . The method of  claim 9 , wherein said polyester product comprises homopolymers or copolymers of polyethylene terephthalate, polyethylene naphthalate, polyethylene isophthalate, polyethylene succinate, and/or polyethylene adipate.  
     
     
         21 . The method of  claim 9 , wherein said polyester product comprises polyethylene terephthalate.  
     
     
         22 . The method of  claim 9 , wherein said alkylene oxide comprises ethylene oxide, propylene oxide, and/or butylene oxide.  
     
     
         22 . The process of  claim 9 , wherein said alkylene oxide comprises ethylene oxide.  
     
     
         23 . The process of  claim 9 , wherein said reaction zone comprises at least one reactor operated at a pressure such that at least 90 weight percent of said alkylene oxide remains in a liquid phase.  
     
     
         24 . The process of  claim 23 , wherein said reactor is operated at a temperature in the range of from about 18° C. to about 280° C.  
     
     
         25 . The process of  claim 23 , wherein said reactor is operated at a pressure in the range of from about 500 to about 1200 psi.