Metal Salts of a Dialkyl Ester of 5-Sulfoisophthalic Acid

Abstract

The claimed invention meets these and other objects by providing a method of preparing a metal salt of a dialkyl ester of 5-sulfoisophthalic acid. Broadly speaking, the method provides for the contacting of a dialkyl ester of 5-sulfoisophthalic acid with a metal cation in a buffered reaction mixture to form the metal salt of the dialkyl ester. The reaction mixture is buffered, at least in part, by the acetate of the metal cation. The method according to invention also encompasses various methods of preparing the dialkyl ester of 5-sulfoisophthalic acid.

1 . A composition of matter comprising a metal salt formed by a method comprising the steps of (i) contacting a dialkyl ester of 5-sulfoisophthalic acid with a metal cation in an aqueous buffered reaction mixture to form the metal salt of the metal cation and the dialkyl ester, wherein the aqueous buffered reaction mixture is buffered by the acetate of the metal cation, and (ii) recovering the metal salt from the aqueous buffered reaction mixture. 
     
     
         2 . The composition of matter according to  claim 1 , wherein the metal cation is selected from the group consisting of cesium, iron (II), cobalt, copper (II), and cadmium. 
     
     
         3 . A composition of matter comprising the reaction product of a metal cation and a dialkyl ester of 5-sulfoisophthalic acid, wherein the reaction occurs in an aqueous reaction mixture buffered by an acetate of the metal cation. 
     
     
         4 . The composition of matter according to  claim 3 , wherein the reaction comprises the steps of (i) contacting the dialkyl ester of 5-sulfosiophthalic acid with the metal cation to form the aqueous reaction mixture comprising the metal salt of the metal cation and the dialkyl ester, (ii) cooling the aqueous reaction mixture to a temperature sufficient to induce crystallization of the metal salt, and (iii) recovering the metal salt from the aqueous reaction mixture. 
     
     
         5 . The composition of matter according to  claim 4 , wherein the reaction comprises the prior step of reacting 5-sulfoisophthalic acid with an alcohol under conditions sufficient to form a solution containing a dialkyl ester of 5-sulfoisophthalic acid, and wherein the step of contacting the dialkyl ester of 5-sulfosiophthalic acid with the metal cation comprises drowning the solution containing the dialkyl ester into a solution buffered by the acetate of the metal cation. 
     
     
         6 . The composition of matter according to  claim 4 , wherein the metal cation is selected from the group consisting of sodium, potassium, lithium, rubidium, cesium, magnesium, calcium, strontium, barium, manganese, iron (II), cobalt, nickel, copper (II), zinc, silver (I), and cadmium. 
     
     
         7 . The composition of matter according to  claim 4 , wherein the metal cation is selected from the group consisting of cesium, iron (II), cobalt, copper (II), and cadmium. 
     
     
         8 . The composition of matter according to  claim 4 , wherein the metal cation is present in a solution formed of bulk metal acetate and water. 
     
     
         9 . The composition of matter according to  claim 4 , wherein the metal cation is present in a solution as the product of combining acetic acid with the aqueous hydroxide of the metal cation. 
     
     
         10 . The composition of matter according to  claim 3 , wherein the diakyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         11 . A polymer containing the composition of matter according to  claim 3 . 
     
     
         12 . A cesium salt of a dialkyl ester of 5-sulfoisophthalic acid. 
     
     
         13 . The cesium salt according to  claim 12 , wherein the dialkyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         14 . A polymer containing the cesium salt of  claim 12 . 
     
     
         15 . An iron (II) salt of a dialkyl ester of 5-sulfoisophthalic acid. 
     
     
         16 . The iron (II) salt according to  claim 15 , wherein the dialkyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         17 . A polymer containing the iron (II) salt of  claim 15 . 
     
     
         18 . A cobalt salt of a dialkyl ester of 5-sulfoisophthalic acid. 
     
     
         19 . The cobalt salt according to  claim 18 , wherein the dialkyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         20 . A polymer containing the cobalt salt of  claim 18 . 
     
     
         21 . A copper (II) salt of a dialkyl ester of 5-sulfoisophthalic acid. 
     
     
         22 . The copper salt according to  claim 21 , wherein the dialkyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         23 . A polymer containing the copper salt of  claim 21 . 
     
     
         24 . A cadmium salt of a dialkyl ester of 5-sulfoisophthalic acid. 
     
     
         25 . The cadmium salt according to  claim 24 , wherein the dialkyl ester is the dimethyl ester of 5-sulfoisophthalic acid. 
     
     
         26 . A polymer containing the cadmium salt of  claim 24 .