Bisphenol compound and process for preparation thereof

Abstract

The present invention provides a novel bisphenol compound of formula (I). wherein R 1 and R 2 are the same or different and are independently either hydrogen or methyl at each occurrence. The present invention also provides a process for preparation of these bisphenol compounds starting from Cashew Nut Shell Liquid (CNSL);—a renewable resource material. The bisphenols prepared in the present invention can be utilized as difunctional monomers for the preparation of various polymers such as epoxy resins, polyesters, polyethersulfones, polyetherketones, polyetherimides, polyarylates, polycarbonates, etc.

1 . (canceled) 
   
   
       2 . (canceled) 
   
   
       3 . A process for the preparation of a bisphenol compound of formula (I), 
     
       
         
         
             
             
         
       
     
     wherein R 1  and R 2  are the same or different and are independently either hydrogen or methyl at each occurrence, the process comprising the steps of:
 (a) dehydroxylating 3-pentadecyl phenol of formula (II) 
 
     
       
         
         
             
             
         
       
        by reacting the 3-pentadecyl phenol with 1-phenyl-5-chlorotetrazole of formula (III) 
     
     
       
         
         
             
             
         
       
        in presence of a weak base in acetone, refluxing the reaction mixture, removing solvent and pouring the resulting concentrate in water to obtain a precipitate, followed by recrystallization in alcohol to obtain 3-pentadecyl-1-(1-phenyl-tetrazolyloxy)phenyl of formula (IV), 
     
     
       
         
         
             
             
         
       
       (b) hydrogenolysing 3-pentadecyl-1-(1-phenyl-tetrazolyloxy)phenyl of formula (IV), in the presence of about 5% palladium-on-charcoal, in an aromatic hydrocarbon solvent, filtering the reaction mixture and washing insoluble residue with hot alcohol, combining the filtrates, concentrating the combined filtrate by removing the solvent to obtain a sticky residue, extracting residue with toluene and washing it with an aqueous metal hydroxide and then again by water, followed by removal of solvent to obtain pentadecyl benzene of formula (V), 
     
     
       
         
         
             
             
         
       
       (c) acetylating the pentadecyl benzene of formula (V) with an acetylating agent, in the presence of a Lewis acid catalyst, in an organic solvent, warming the reaction mixture, pouring the reaction mixture in ice, extracting the resultant compound with a halocarbon solvent, washing extracts so obtained with dilute HCl and then again by water, followed by removal of solvent to obtain 4-acetyl pentadecyl benzene of formula (VI), 
     
     
       
         
         
             
             
         
       
       (d) reacting 4-acetyl pentadecyl benzene of formula (VI) with substituted or unsubstituted phenol, in the presence of an acidic catalyst, dissolving the reaction mixture in ethyl acetate and subsequently washing with an aqueous solution of a weak base and water, respectively, removing the solvent and purifying the resultant product to obtain the desired bisphenol compound of formula (I). 
     
   
   
       4 . A process as claimed in  claim 3 , wherein the weak base used in step (a) is selected from potassium carbonate or sodium carbonate. 
   
   
       5 . A process as claimed in  claim 3 , wherein the alcohol used in step (a) is selected from methanol or ethanol. 
   
   
       6 . A process as claimed in  claim 3 , wherein the refluxing in step (a) is carried out for a period of at least 16 hours. 
   
   
       7 . A process as claimed in  claim 3 , wherein the aromatic hydrocarbon solvent used in hydrogenolysis in step (b) is selected from toluene or benzene. 
   
   
       8 . A process as claimed in  claim 3 , wherein the hydrogenolysing in step (b) is carried out in a Parr reactor. 
   
   
       9 . A process as claimed in  claim 3 , wherein step (b) is carried out at a pressure of about 40 psi and at a temperature in the range of 35-40° C. for at least 8 hours. 
   
   
       10 . A process as claimed in  claim 3 , wherein the acetylating agent used in step (c) is selected from the group consisting of acetic acid, acetic anhydride and acetyl chloride. 
   
   
       11 . A process as claimed in  claim 3 , wherein the metal hydroxide used in step (b) is an alkali metal hydroxide selected from sodium hydroxide or potassium hydroxide. 
   
   
       12 . A process as claimed in  claim 3 , wherein the Lewis acid catalyst used in step (c) is selected from AlCl 3  or BF 3 . 
   
   
       13 . A process as claimed in  claim 3 , wherein the organic solvent used for acetylation in step (c) is selected from a halogenated hydrocarbon or a nitrogen compound. 
   
   
       14 . A process as claimed in  claim 13 , wherein the halogenated hydrocarbon is selected from dichloromethane or chloroform. 
   
   
       15 . A process as claimed in  claim 13 , wherein the nitrogen compound is selected from nitromethane or nitrobenzene. 
   
   
       16 . A process as claimed in  claim 3 , wherein in step (c) acetylation is carried out at a temperature below 5° C., for a period of at least about 2 hours, followed by warming the reaction mixture to a temperature of 30-40° C., for at least 5-6 hours. 
   
   
       17 . A process as claimed in  claim 3 , wherein the acid catalyst used in phenol condensation in step (d) is selected from the group consisting of acidic clays, sulfated zirconia, 3-mercaptopropionic acid, glacial acetic acid, hydrogen chloride and any mixture thereof. 
   
   
       18 . A process as claimed in  claim 3 , wherein in step (d) reaction of 4-acetyl pentadecyl benzene of formula (VI) with substituted or unsubstituted phenol is effected at a temperature in the range of 30-50° C., for a period of about 4 days.