Process for preparing an alkylcyclohexanol alkyleneoxide adduct

Abstract

The invention is a preparation process of alkylcyclohexanol alkylene oxide adduct which contains almost no alkylphenol alkylene oxide adduct 1) in the absence of a solvent, 2) in the presence of a saturated hydrocarbon solvent, or 3) in the presence of water. The invention can prepare alkylcyclohexanol alkylene oxide having a 200 ppm or less content of alkylphenol and alkylphenol alkylene oxide adduct. The alkylcyclohexanol alkylene oxide adduct obtained in the process of the invention has less ultraviolet absorption and fluorescence due to alkylphenol alkylene oxide adduct and is thus useful for spectrometric analysis of protein and further has excellent properties in the field of detergent and other common uses of surface active agents.

What is claimed is:  
     
         1 . An alkylcyclohexanol alkylene oxide adduct which has a 200 ppm or less content of alkylphenol and alkylphenol alkylene oxide adduct and is represented by the formula (1):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 6 to 20 carbon atoms, R 2  is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more:  
     
     
         2 . The alkylcyclohexanol alkylene oxide adduct according to  claim 1 , wherein the content of alkylphenol and alkylphenol alkylene oxide adduct is 10 ppm by weight or less.  
     
     
         3 . A process for preparing an alkylcyclohexanol alkylene oxide adduct represented by the formula (1):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 6 to 20 carbon atoms, R 2  is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more, comprising reacting alkylphenol alkylene oxide adduct represented by the formula (2):  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2  and n are the same as above, with hydrogen in the presence of a supported catalyst of ruthenium or rhodium in the absence of a solvent under hydrogen pressure exceeding gauge pressure 2.0 MPa, at temperature of 80 to 150° C.  
     
     
         4 . A process for preparing an alkylcyclohexanol alkylene oxide adduct represented by the formula (1):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 6 to 20 carbon atoms, R 2  is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more, comprising reacting alkylphenol alkylene oxide adduct represented by the formula (2):  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2  and n are the same as above, with hydrogen in the presence of water by using a supported catalyst of ruthenium, rhodium, palladium or platinum.  
     
     
         5 . A process for preparing an alkylcyclohexanol alkylene oxide adduct represented by the formula (1):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 6 to 20 carbon atoms, R 2  is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more, comprising reacting alkylphenol alkylene oxide adduct represented by the formula (2):  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2  and n are the same as above, with hydrogen in a saturated hydrocarbon solvent in the presence of a supported catalyst of ruthenium, rhodium, palladium or platinum.  
     
     
         6 . A process for preparing a high purity alkylcyclohexanol alkylene oxide adduct which has a narrow addition distribution of alkylene oxide and is represented by the formula (1):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 6 to 20 carbon atoms, R 2  is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more, comprising the step consisting of: 
   1 ) the first alkylene oxide addition step for reacting one mole of alkylphenol represented by the formula (4):  
                     wherein R 1  is an alkyl group having 6 to 20 carbon atoms, with 0.9 to 1.2 moles of alkylene oxide in the presence of a basic catalyst to obtain a formed product primarily consisting of one molar alkylene oxide adduct of alkylphenol,    2) a hydrogenation step for reacting the formed product obtained in the first alkylene oxide addition step with hydrogen in the presence of a hydrogenation catalyst to obtain a resulting product primarily consisting of one molar alkylene oxide adduct of alkylcyclohexanol,    3) a distillation step for distillating the resulting product obtained in the hydrogenation step to obtain a fraction primarily consisting of alkylcyclohexanol alkylene oxide adduct and having a content of 10 ppm by weight or less in the sum of alkylphenol and alkylphenol alkylene oxide adduct, and    4) the second alkylene oxide addition step for reacting the fraction obtained in the distillation step and primarily consisting of one molar alkylene oxide adduct of cyclohexanol with alkylene oxide having 2 to 4 carbon atoms in the presence of a basic catalyst.    
 
     
     
         7 . A process for preparing a high purity alkylcyclohexanol alkylene oxide adduct which has a narrow addition distribution of alkylene-oxide and is represented by the formula (1):