Catalyst for producing conjugated diene, production method for said catalyst, and production method for conjugated diene

Abstract

Provided is a technique of producing isoprene from 3-methyl-1,3-butanediol or 1,3-butadiene from 1,3-butanediol by using a single catalyst. A catalyst produces a conjugated diene containing zirconium oxide and calcium oxide in order to produce isoprene by removing two water molecules from one 3-methyl-1,3-butanediol molecule or produce 1,3-butadiene by removing two water molecules from one 1,3-butanediol molecule. Furthermore, a method for producing a conjugated diene includes a step of obtaining a fluid containing a conjugated diene that is isoprene or 1,3-butadiene by bringing a fluid containing 3-methyl-1,3-butanediol or a fluid containing 1,3-butanediol into contact with the catalyst for producing a conjugated diene as a single catalyst so as to cause a dehydration reaction to proceed.

1 . A catalyst for producing a conjugated diene, causing a reaction of removing two water molecules from one 3-methyl-1,3-butanediol molecule to produce isoprene to proceed, the catalyst comprising zirconium oxide and calcium oxide. 
     
     
         2 . The catalyst for producing a conjugated diene according to  claim 1 , wherein the catalyst for producing a conjugated diene is used under a condition that a mass flow rate (WHSV: Weight Hourly Space Velocity) of the 3-methyl-1,3-butanediol per unit time with respect to a weight of the catalyst for producing a conjugated diene is 1.5 h −1  or less. 
     
     
         3 . A catalyst for producing a conjugated diene, causing a reaction of removing two water molecules from one 1,3-butanediol molecule to produce 1,3-butadiene to proceed, the catalyst comprising zirconium oxide and calcium oxide. 
     
     
         4 . The catalyst for producing a conjugated diene according to  claim 3 , wherein the catalyst for producing a conjugated diene is used under a condition that a mass flow rate (WHSV) of the 1,3-butanediol per unit time with respect to a weight of the catalyst for producing a conjugated diene is 1.5 −1  or less. 
     
     
         5 . The catalyst for producing a conjugated diene according to  claim 1 , wherein a content of calcium atom of the calcium oxide with respect to 1 mol of zirconium atom of the zirconium oxide is within a range of 0.01 mol or more and 0.3 mol or less. 
     
     
         6 . The catalyst for producing a conjugated diene according to  claim 1 , wherein the calcium oxide is supported on the zirconium oxide. 
     
     
         7 . The catalyst for producing a conjugated diene according to  claim 1 , wherein the zirconium oxide has a tetragonal form or a cubic form. 
     
     
         8 . The catalyst for producing a conjugated diene according to  claim 1 , wherein the zirconium oxide is yttria-stabilized zirconia (YSZ). 
     
     
         9 . A method for producing the catalyst for producing a conjugated diene according to  claim 1 , the method comprising a step of calcining the zirconium oxide or a precursor containing zirconium at a temperature within a range of 700° C. or higher and 1200° C. or lower. 
     
     
         10 . A method for producing a conjugated diene, the method comprising a step of obtaining a fluid containing a conjugated diene that is isoprene by bringing a fluid containing 3-methyl-1,3-butanediol into contact with the catalyst for producing a conjugated diene according to  claim 1  to remove two water molecules from one 3-methyl-1,3-butanediol molecule. 
     
     
         11 . The method for producing a conjugated diene according to  claim 10 , wherein in the step of obtaining a fluid containing a conjugated diene, a mass flow rate (WHSV) of the 3-methyl-1,3-butanediol per unit time with respect to a weight of the catalyst for producing a conjugated diene is 1.5 h −1  or less. 
     
     
         12 . A method for producing a conjugated diene, the method comprising a step of obtaining a fluid containing a conjugated diene that is 1,3-butadiene by bringing a fluid containing 1,3-butanediol into contact with the catalyst for producing a conjugated diene according to  claim 3  to remove two water molecules from one 1,3-butanediol molecule. 
     
     
         13 . The method for producing a conjugated diene according to  claim 12 , wherein in the step of obtaining a fluid containing a conjugated diene, a mass flow rate (WHSV) of the 1,3-butanediol per unit time with respect to a weight of the catalyst for producing a conjugated diene is 1.5 h −1  or less. 
     
     
         14 . The method for producing a conjugated diene according to  claim 10 , wherein the step of obtaining a fluid containing a conjugated diene is performed at a reaction temperature within a range of 250C° C. or higher and 400° C. or lower. 
     
     
         15 . The method for producing a conjugated diene according to  claim 10 , comprising a step of calcining the catalyst for producing a conjugated diene at a temperature within a range of 700° C. or higher and 1200° C. or lower before performing the step of obtaining a fluid containing a conjugated diene. 
     
     
         16 . The catalyst for producing a conjugated diene according to  claim 3 , wherein a content of calcium atom of the calcium oxide with respect to 1 mol of zirconium atom of the zirconium oxide is within a range of 0.01 mol or more and 0.3 mol or less. 
     
     
         17 . The catalyst for producing a conjugated diene according to  claim 3 , herein the calcium oxide is supported on the zirconium oxide. 
     
     
         18 . The catalyst for producing a conjugated diene according to  claim 3 , wherein the zirconium oxide has a tetragonal form or a cubic form. 
     
     
         19 . The catalyst for producing a conjugated diene according to  claim 3 , wherein the zirconium oxide is yttria-stabilized zirconia (YSZ). 
     
     
         20 . A method for producing the catalyst for producing a conjugated diene according to  claim 3 , the method comprising a step of calcining the zirconium oxide or a precursor containing zirconium at a temperature within a range of 700° C. or higher and 1200° C. or lower. 
     
     
         21 . The method for producing a conjugated diene according to  claim 12 , herein the step of obtaining a fluid containing a conjugated diene is performed at a reaction temperature within a range of 250C° C. or higher and 400° C. or lower. 
     
     
         22 . The method for producing a conjugated diene according to  claim 12 , comprising a step of calcining the catalyst for producing a conjugated diene at a temperature within a range of 700° C. or higher and 1200° C. or lower before performing the step of obtaining a fluid containing a conjugated diene.