Mixture of alicyclic polycarboxylic esters having high cis content

Abstract

The present invention relates to mixtures of alicyclic polycarboxylic esters with high cis content, to a process for their preparation by ring-hydrogenation of the corresponding aromatic polycarboxylic esters, and also to the use of the mixtures.

1 - 15 . (canceled) 
   
   
       16 . An alicyclic polycarboxylic acid ester mixture, comprising:
 at least two isomers of an alicyclic polycarboxylic acid ester whose structures are determined by the positions of the ester groups on the ring system of the ester compound, with the exception of dimethyl 1,2-cyclohexanedicarboxylates, wherein the proportion of the cis isomers in the isomer mixture is above 93 mol %, and wherein the alicyclic polycarboxylic acid ester mixture is prepared by hydrogenating the corresponding aromatic polycarboxylic acid esters over a catalyst which comprises a precious metal of the 8 th  transition metal Group of the Periodic Table and at least one metal of the 2 nd  transition Group of the Periodic Table.   
   
   
       17 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the ring system is a compound of one or more C 6  rings. 
   
   
       18 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the polycarboxylic esters have 2, 3 or 4 ester groups. 
   
   
       19 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alcohol components of the alicyclic polycarboxylic esters are alkoxyalkyl, cycloalkyl, and/or alkyl groups having from 1 to 25 carbon atoms, are branched or unbranched, and are in each instance identical or different. 
   
   
       20 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester mixture comprises the isomers of the cyclohexane-1,2-dicarboxylic acid esters, 1,3-dicarboxylic acid esters, or 1,4-dicarboxylic acid esters, or the isomers of the cyclohexane-1,2,3-tricarboxylic acid esters, 1,2,4-tricarboxylic acid esters, or 1,3,5-tricarboxylic acid esters. 
   
   
       21 . A method of plasticizing a plastic material, comprising: blending the alicyclic polycarboxylic acid ester mixture of  claim 16  into a plastic material. 
   
   
       22 . A plasticized material prepared by the method of  claim 21 . 
   
   
       23 . The plasticized material of  claim 22 , wherein the amount of alicyclic polycarboxylic acid ester in the plasticized material is at least 5% by weight. 
   
   
       24 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester mixture comprises at least two isomers selected from the group consisting of cyclohexane-1,2-dicarboxylic acid esters, cyclohexane-1,3-dicarboxylic acid esters, cyclohexane-1,4-dicarboxylic acid esters, cyclohexane-1,2,3-tricarboxylic acid esters, cyclohexane-1,2,4-tricarboxylic acid esters, cyclohexane-1,3,5-tricarboxylic acid esters, and mixtures thereof. 
   
   
       25 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester mixture comprises at least two isomers selected from the group consisting of cyclohexane-1,2,3-tricarboxylic acid esters, cyclohexane-1,2,4-tricarboxylic acid esters, cyclohexane-1,3,5-tricarboxylic acid esters, and mixtures thereof. 
   
   
       26 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester mixture comprises at least two isomers selected from the group consisting of cyclohexane-1,2-dicarboxylic acid esters, cyclohexane-1,3-dicarboxylic acid esters, cyclohexane-1,4-dicarboxylic acid esters, and mixtures thereof. 
   
   
       27 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester isomer mixture is prepared by hydrogenating the corresponding naphthalene-polycarboxylic acid ester isomers selected from the group consisting of naphthalene-1,2-dicarboxylic acid esters, naphthalene-1,3-dicarboxylic acid esters, naphthalene-1,4-dicarboxylic acid esters, naphthalene-1,5-dicarboxylic acid esters, naphthalene-1,6-dicarboxylic acid esters, naphthalene-1,7-dicarboxylic acid esters, naphthalene-1,8-dicarboxylic acid esters, and mixtures thereof. 
   
   
       28 . The alicyclic polycarboxylic acid ester mixture of  claim 16 , wherein the alicyclic polycarboxylic ester isomer mixture is prepared by hydrogenating the corresponding aromatic polycarboxylic acid ester isomers selected from the group consisting of phthalic acid (benzene-1,2-dicarboxylic acid ester), isophthalic acid (benzene-1,3-dicarboxylic acid ester), terephthalic acid (benzene-1,4-dicarboxylic acid ester), benzene-1,2,3,4-tetracarboxylic acid, and mixtures thereof.