Separation of propylene oxide from a mixture comprising propylene oxide and methanol

Abstract

A method of separating propylene oxide from a mixture (M) comprising propylene oxide and methanol, said method comprising (i) introducing said mixture (M) into an extractive distillation column; (ii) additionally introducing an extracting solvent into said extractive distillation column; (iii) distilling propylene oxide overhead from said extractive distillation column as top stream; (iv) withdrawing a bottoms stream from said extractive distillation column; (v) compressing the top stream obtained overhead in (iii) by means of at least one compressor to give a compressed vapor.

1 . A method of separating propylene oxide from a mixture (M) comprising propylene oxide and methanol, said method comprising 
 (i) introducing said mixture (M) into an extractive distillation column;    (ii) additionally introducing an extracting solvent into said extractive distillation column;    (iii) distilling propylene oxide overhead from said extractive distillation column as top stream;    (iv) withdrawing a bottoms stream from said extractive distillation column;    (v) compressing the top stream obtained overhead in (iii) by means of at least one compressor to give a compressed vapor.    
     
     
         2 . The method as claimed in  claim 1 , wherein, in (iii), the distillation is carried out at a pressure of 1.5 bar or less, and, in (v), the top stream is compressed to a pressure of more than 1.5 bar.  
     
     
         3 . The method as claimed in  claim 2 , wherein, in (iii), the distillation is carried out at a pressure of from 300 to 750 mbar and a bottoms temperature of from 40 to 70° C., and, in (v), the top stream is compressed to a pressure of from 2 to 4 bar.  
     
     
         4 . The method as claimed in  claim 3 , wherein, in (v), the top stream is compressed to a pressure of from 2.5 to 3.5 bar.  
     
     
         5 . The method as claimed in  claim 1 , additionally comprising 
 (vi) condensing the compressed vapor obtained in (v) and returning at least part of the heat of condensation to at least one reboiler employed in the extractive distillation column.    
     
     
         6 . The method as claimed in  claim 5 , additionally comprising 
 (vii) cooling at least part of the condensate obtained in (vi) to a temperature in the range from 10 to 30° C. in at least one heat exchanger and returning this part of the cooled condensate as reflux to the extractive distillation column used in (iii).    
     
     
         7 . The method as claimed in  claim 6 , additionally comprising 
 (viii) depressurizing a compressed propene stream into the at least one heat exchanger in (vii), vaporizing the propane stream in the at least one heat exchanger and subsequently using the propene as reactant in a reaction comprising reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst.    
     
     
         8 . The method as claimed in  claim 1 , wherein the energy stored in the bottom stream obtained in (iv) is at least partly used for heating or preheating the mixture (M) before said mixture is introduced into the extractive distillation column in (i).  
     
     
         9 . The method as claimed in  claim 1 , wherein the mixture (M) is formed in a reaction comprising reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst.  
     
     
         10 . The method as claimed in  claim 1 , wherein water is used as extracting solvent.  
     
     
         11 . The method as claimed in  claim 10 , wherein the water is introduced as vapor at a pressure of not more than 2 bar.  
     
     
         12 . The method as claimed in  claim 1 , wherein said mixture (M) comprises 5 to 50 percent by weight propylene oxide and 50 to 85 percent by weight methanol.  
     
     
         13 . The method as claimed in  claim 12 , said mixture (M) comprising 5 to 15 percent by weight propylene oxide and additionally comprising 10 to 25 percent by weight water.  
     
     
         14 . The method as claimed in  claim 1 , wherein the extracting solvent is introduced in an amount of 2 percent by weight, based on the total weight of the mixture (M), or less.  
     
     
         15 . The method as claimed in  claim 14 , wherein the extracting solvent is introduced in an amount of from 0.45 to 1 percent by weight of the mixture (M), based on the total weight of the mixture (M).  
     
     
         16 . The method as claimed in  claim 1 , wherein the extractive distillation column has up to 80 theoretical plates.  
     
     
         17 . The method as claimed in  claim 6 , wherein the mass ratio of reflux to distillate, obtained as top stream in (iii), is 4.9 or less.  
     
     
         18 . The method as claimed in  claim 1 , wherein the top stream distilled overhead comprises 100 ppm methanol or less and the bottoms stream withdrawn from the extractive distillation column has a propylene oxide content of 100 ppm or less.  
     
     
         19 . A method of separating propylene oxide from a mixture (M) comprising 5 to 15 percent by weight propylene oxide, 50 to 85 percent by weight methanol, and 10 to 25 percent by weight water, said method comprising 
 (i) introducing said mixture (M) into an extractive distillation column;    (ii) additionally introducing a polar extracting solvent into said extractive distillation column;    (iii) distilling propylene oxide overhead from said extractive distillation column as top stream, the top stream comprising 100 ppm methanol or less;    (v) compressing the top stream obtained overhead in (iii) by means of at least one compressor to give a compressed vapor;    (vi) condensing the compressed vapor obtained in (v) and returning at least part of the heat of condensation to at least one reboiler employed in the extractive distillation column.    
     
     
         20 . The method as claimed in  claim 19 , wherein, in (iii), the distillation is carried out at a pressure of from 300 to 750 mbar and a bottoms temperature of from 40 to 70° C., and, in (v), the top stream is compressed to a pressure of from 2 to 4 bar.  
     
     
         21 . The method as claimed in  claim 19 , additionally comprising 
 (vii) cooling at least part of the condensate obtained in (vi) to a temperature in the range from 10 to 30° C. in at least one heat exchanger and returning this part of the cooled condensate as reflux to the extractive distillation column used in (iii).    
     
     
         22 . The method as claimed in  claim 21 , additionally comprising 
 (viii) depressurizing a compressed propene stream into the at least one heat exchanger in (vii), vaporizing the propene stream in the at least one heat exchanger and subsequently using the propene as reactant in a reaction comprising reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst.    
     
     
         23 . The method as claimed in  claim 19 , wherein water is used as polar extracting solvent and introduced in an amount of 2 percent by weight of the mixture (M), based on the total weight of the mixture (M), or less.  
     
     
         24 . The method as claimed in  claim 19 , wherein the mass ratio of reflux to distillate is 4.9 or less.  
     
     
         25 . A method of separating propylene oxide from a mixture (M) comprising 5 to 15 percent by weight propylene oxide, 50 to 85 percent by weight methanol, and 10 to 25 percent by weight water, said method comprising 
 (i) introduction said mixture (M) into an extractive distillation column;    (ii) additionally introducing water into said extractive distillation column in an amount of 2 percent by weight of the mixture (M) or less;    (iii) distilling propylene oxide overhead from said extractive distillation column as top stream at a pressure of from 300 to 750 mbar and a bottoms temperature of from 40 to 70° C., the top stream comprising 100 ppm methanol or less;    (iv) withdrawing a bottoms stream from said extractive distillation column comprising 100 ppm propylene oxide or less;    (v) compressing the top stream obtained overhead in (iii) to a pressure of from 2 to 4 bar by means of at least one compressor to give a compressed vapor;    (vi) condensing the compressed vapor obtained in (v) and returning at least part of the heat of condensation to at least one vaporizer employed in the extractive distillation column.    
     
     
         26 . The method as claimed in  claim 25 , additionally comprising 
 (vii) cooling at least part of the condensate obtained in (vi) to a temperature in the range from 10 to 30° C. in at least one heat exchanger and returning this part of the cooled condensate as reflux to the distillation column used in (iii) in an amount so that the mass ratio of reflux to distillate is 4 or less.    
     
     
         27 . The method as claimed in  claim 26 , additionally comprising 
 (viii) depressurizing a compressed propene stream into the at least one heat exchanger in (vii), vaporizing the propene stream in the at least one heat exchanger and subsequently using the propene as reactant in a reaction comprising reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst, said reaction resulting in mixture (M) or a mixture being worked up to give mixture (M).    
     
     
         28 . The method as claimed in  claim 25 , wherein the energy stored in the bottom stream obtained in (iv) is at least partly used for heating or preheating the mixture (M) before said mixture is introduced into the extractive distillation column in (i).  
     
     
         29 . A method of separating propylene oxide from a mixture (M) comprising 5 to 15 percent by weight propylene oxide, 50 to 85 percent by weight methanol, and 10 to 25 percent by weight water, said method comprising 
 (i) introducing said mixture (M) into an extractive distillation column;    (ii) additionally introducing water into said extractive distillation column in an amount of from 0.45 to 1 percent by weight of the mixture (M);    (iii) distilling propylene oxide overhead from said extractive distillation column at a bottoms temperature of from 50 to 60° C. and a pressure of from 450 to 500 mbar, the propylene oxide traction comprising 50 ppm methanol or less;    (iv) withdrawing a bottoms stream from said extractive distillation column, said bottoms stream comprising 100 ppm propylene oxide or less;    (v) compressing the top stream obtained in (iii) to a pressure in the range from 2 to 4 bar by means of at least one compressor to give a compressed vapor;    (vi) condensing the compressed vapor obtained in (v) and returning at least part of the heat of condensation to at least one vaporizer used in the extractive distillation column,    (vii) cooling at least part of the condensate obtained in (vi) to a temperature in the range of from 10 to 30° C. in at least one heat exchanger and returning this part of the cooled condensate as reflux to the extractive distillation column employed in (ill) so that the mass ratio of reflux to distillate is 4 or less;    wherein the mixture (M) is formed by reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst.    
     
     
         30 . A method of preparing propylene oxide, said reaction comprising reacting propene with hydrogen peroxide in methanol as solvent and in the presence of a titanium zeolite fixed-bed catalyst, said reaction resulting in mixture (M) comprising 5 to 15 percent by weight propylene oxide, 50 to 85 percent by weight methanol, and 10 to 25 percent by weight water, or a mixture being worked up to give mixture (M), said method further comprising 
 (i) introducing said mixture (M) into an extractive distillation column;    (ii) additionally introducing water into said extractive distillation column in an amount of 0.45 to 1 percent by weight of the mixture (M) or less;    (iii) distilling propylene oxide overhead from said extractive distillation column as top stream at a pressure of from 450 to 500 mbar and a bottoms temperature of from 50 to 60° C., the top stream comprising 100 ppm methanol or less;    (iv) withdrawing a bottoms stream from said extractive distillation column and using the energy stored in the bottom stream at least partly for heating the mixture (M) before said mixture is introduced into the extractive distillation column in (i);    (v) compressing the top stream obtained overhead in (iii)-to a pressure of from 2.5 to 3.5 bar by means of at least one compressor to give a compressed vapor,    (vi) condensing the compressed vapor obtained in (v) and returning at least part of the heat of condensation to at least one vaporizer employed in the extractive distillation column,    (vii) cooling at least part of the condensate obtained in (vi) to a temperature in the range from 10 to 30° C. in at least one heat exchanger and returning this part of the cooled condensate as reflux to the extractive distillation column used in (iii) in an amount so that the mass ratio of reflux to distillate is 4 or less;    (viii) depressurizing a compressed propene stream into the at least one heat exchanger in (vii), vaporizing the propene stream in the at least one heat exchanger and subsequently using the propene as reactant in said reaction.