Compositions and methods related to the production of acrylonitrile

Abstract

Disclosed herein are a catalyst and method useful in the process of converting sugars to acrylonitrile.

1 . A catalyst composition for converting propylene glycol and glycerol to acrolein comprising a catalyst having the formula:
   M1M2 x M3 y O z      wherein M1 is a metal promoting dehydrogenation and C—O cleavage,   wherein M2 is a metal with acid sites promoting dehydration,   wherein M3 is an amphoteric catalyst support, with acid and base sites, promoting both dehydration and dehydrogenation in conjunction with M1,   wherein x is a molar ratio from about 0.25 to about 4,   wherein y is a molar ratio from about 0.25 to about 4,   wherein z is the total amount of oxygen bound to M1, M2, and M3, and corresponds to the sum of the oxidation states of M1, M2, and M3.   
     
     
         2 - 10 . (canceled) 
     
     
         11 . A method comprising the step of:
 a. contacting a first product comprising ethylene glycol, propylene glycol, and glycerol with the catalyst composition of  claim 1 , thereby producing a second product comprising acrolein and acetaldehyde.   
     
     
         12 . The method of  claim 11 , wherein the method further comprises the steps of:
 b) separating at least a portion of the acetaldehyde from the second product; and   c) following step b) converting at least a portion of the acrolein in the second product to acrylonitrile.   
     
     
         13 - 14 . (canceled) 
     
     
         15 . The method of  claim 11 , wherein from about 50 wt % to about 90 wt % of the propylene glycol and glycerol in the first product are converted to acrolein. 
     
     
         16 . The method of  claim 11 , wherein the second product comprises from about 20 wt % to about 75 wt % of acrolein. 
     
     
         17 - 18 . (canceled) 
     
     
         19 . The method of  claim 11 , wherein step a) is performed at atmospheric pressure. 
     
     
         20 . A method comprising the step of:
 a. in a single step, converting C5 and/or C6 sugars to a first product comprising ethylene glycol, propylene glycol, and glycerol in the presence of a multifunctional catalyst.   
     
     
         21 . The method of  claim 20 , wherein the multifunctional catalyst comprises one or more metals selected from the group consisting of Cu, Zn, Sn, Ni, Pt, Pd, Ru, and Re, and a support. 
     
     
         22 . The method of  claim 21 , wherein the support is selected from the group consisting of Al 2 O 3 , SiO 2 , Carbon, TiO 2 , and MgO. 
     
     
         23 . The method of  claim 20 , wherein the method further comprises the step of separating water from the first product. 
     
     
         24 . The method of  claim 20 , wherein the method further comprises the step of contacting the first product comprising ethylene glycol, propylene glycol, and glycerol with the catalyst composition of  claim 1 , thereby producing a second product comprising acrolein and acetaldehyde. 
     
     
         25 . The method of  claim 24 , wherein method further comprises the steps of separating at least a portion of the acetaldehyde from the second product; and converting at least a portion of the acrolein in the second product to acrylonitrile. 
     
     
         26 - 28 . (canceled) 
     
     
         29 . A method comprising the step of:
 a. contacting propylene glycol with a catalyst composition, thereby producing acrolein.   
     
     
         30 . The method of  claim 29 , wherein the catalyst composition is the catalyst composition of  claim 1 . 
     
     
         31 . The method of  claim 30 , wherein M1 is selected from the group consisting of Cu, Zn, and Sn, wherein M2 is selected from the group consisting of W, Fe, P, and a zeolite, wherein M3 is selected from the group consisting of Zr, Al, Si, Mg, Ti, La, and Ce. 
     
     
         32 . The method of  claim 30 , wherein the catalyst has the formula CuOWO 3 ZrO 2  or CuOWO 3 TiO 2  or CuO/WO 3 /SiO 2 . 
     
     
         33 . The method of  claim 29 , wherein step a) is performed at atmospheric pressure. 
     
     
         34 . The method of  claim 29 , wherein from about 10 wt % to about 90 wt % of the propylene glycol is converted to acrolein. 
     
     
         35 . The method of  claim 11 , wherein M1 is selected from the group consisting of Cu, Zn, and Sn, wherein M2 is selected from the group consisting of W, Fe, P, and a zeolite, and wherein M3 is selected from the group consisting of Zr, Al, Si, Mg, Ti, La, and Ce. 
     
     
         36 . The method of  claim 11 , wherein the catalyst has the formula CuOWO 3 ZrO 2  or CuOWO 3 TiO 2  or CuOWO 3 SiO 2