Method for Producing Cyclododecanone

Abstract

A process for preparing cyclododecanone by reacting cyclododecene with dinitrogen monoxide, comprising in particular steps (I) and (II): (I) preparing cyclododecene by partially hydrogenating cyclododecatriene; (II) reacting cyclododecene obtained in (I) with dinitrogen monoxide to obtain cyclododecanone.

1 . A process for preparing cyclododecanone by reacting cyclododecene with dinitrogen monoxide. 
     
     
         2 . A process as claimed in  claim 1 , wherein the dinitrogen monoxide source is at least one dinitrogen monoxide-containing offgas of at least one industrial process. 
     
     
         3 . A process as claimed in  claim 2 , wherein the dinitrogen monoxide source is the offgas of an adipic acid plant and/or of a dodecanedioic acid plant and/or of a hydroxylamine plant and/or of a nitric acid plant operated with the offgas of an adipic acid plant and/or of a dodecanedioic acid plant and/or of a hydroxylamine plant. 
     
     
         4 . A process as claimed in any of  claims 1  to  3 , wherein cyclododecene is reacted with a gas mixture containing from 20 to 99.9% by weight of dinitrogen monoxide, based on the total weight of the gas mixture. 
     
     
         5 . A process as claimed in any of  claims 1  to  4 , wherein dinitrogen monoxide or the gas mixture containing dinitrogen monoxide is used in liquid form. 
     
     
         6 . A process as claimed in any of  claims 1  to  5 , wherein the reaction is carried out continuously in at least one tubular reactor at a temperature in the range from 140 to 350° C. 
     
     
         7 . A process as claimed in any of  claims 1  to  6 , wherein a mixture comprising cis-cyclododecene and trans-cyclododecene is reacted with dinitrogen monoxide in two stages. 
     
     
         8 . A process as claimed in  claim 7 , wherein the reaction in the first stage is carried out at a temperature in the range from 140 to 300° C. and the reaction in the second stage at a temperature in the range from 165 to 325° C., the temperature in the first stage being lower than the temperature in the second stage. 
     
     
         9 . A process as claimed in any of  claims 1  to  8 , wherein the cyclododecene is obtained from the catalytic hydrogenation of at least one cyclododecatriene. 
     
     
         10 . A process as claimed in  claim 9 , wherein cyclododecatriene is hydrogenated to cyclododecene and cyclododecene is converted to cyclododecanone using dinitrogen monoxide in the presence of the same catalyst. 
     
     
         11 . A process as claimed in  claim 10 , wherein the reactant used for the reaction with dinitrogen monoxide is a mixture which results from the hydrogenation of cyclododecatriene to cyclododecene in the presence of a homogeneous catalyst and comprises cyclododecene and homogeneous catalysts. 
     
     
         12 . A process for preparing cyclododecanone, which comprises steps (I) and (II):
 (I) preparing cyclododecene by partially hydrogenating cyclododecatriene;   (II) reacting cyclododecene obtained in (I) with dinitrogen monoxide to obtain cyclododecanone.   
     
     
         13 . A process as claimed in  claim 12 , wherein the source used for the dinitrogen monoxide used in (II) is at least one offgas comprising dinitrogen monoxide from at least one industrial process. 
     
     
         14 . A process as claimed in  claim 13 , wherein the dinitrogen monoxide source is the offgas of an adipic acid plant and/or of a dodecanedioic acid plant and/or of a hydroxylamine plant and/or of a nitric acid plant operated with the offgas of an adipic acid plant and/or of a dodecanedioic acid plant and/or of a hydroxylamine plant. 
     
     
         15 . A process as claimed in any of  claims 12  to  14 , wherein cyclododecene is reacted in (II) with a gas mixture containing from 20 to 99.9% by weight of dinitrogen monoxide, based on the total weight of the gas mixture. 
     
     
         16 . A process as claimed in any of  claims 12  to  15 , wherein the dinitrogen monoxide or the gas mixture containing dinitrogen monoxide is used in liquid form. 
     
     
         17 . A process as claimed in any of  claims 12  to  16 , wherein the reaction is carried out in (II) continuously in at least one tubular reactor at a temperature in the range from 140 to 350° C. 
     
     
         18 . A process as claimed in any of  claims 12  to  17 , wherein a mixture comprising cis-cyclododecene and trans-cyclododecene is reacted in (II) with dinitrogen monoxide in two stages. 
     
     
         19 . A process as claimed in  claim 18 , wherein the reaction in the first stage is carried out at a temperature in the range from 140 to 300° C. and the reaction in the second stage at a temperature in the range from 165 to 325° C., the temperature in the first stage being lower than the temperature in the second stage. 
     
     
         20 . A process as claimed in any of  claims 12  to  19 , wherein cyclododecatriene is partially hydrogenated to cyclododecene in (I) and cyclododecene is converted to cyclododecanone using dinitrogen monoxide in (II) in the presence of the same catalyst. 
     
     
         21 . A process as claimed in  claim 20 , wherein the reactant used for the reaction with dinitrogen monoxide in (II) is a mixture which results from the partial hydrogenation of cyclododecatriene to cyclododecene in the presence of a homogeneous catalyst in (I) and comprises cyclododecene and homogeneous catalyst.