Lewis and bronsted-lowry acid-catalyzed production 5-hydroxymethylfurfural (HMF) from glucose
Described is a process to make hydroxymethylfurfural (HMF) from glucose. The process includes the steps of reacting a feedstock solution comprising glucose, in the presence of a homogeneous Brønsted acid catalyst and a homogeneous Lewis acid catalyst, in a reaction vessel containing a biphasic reaction medium. The reaction medium includes an aqueous reaction solution and a substantially immiscible organic extraction solution. HMF is produced in the aqueous reaction solution and extracted into the organic extraction solution.
1. A process to make hydroxymethylfurfural (HMF) from glucose, glucose-containing oligomers, glucose-containing polymers, or combinations thereof, the process comprising:
reacting a feedstock solution comprising glucose, glucose-containing oligomers, glucose-containing polymers, or combinations thereof, in the presence of a homogeneous Brønsted acid catalyst and a homogeneous Lewis acid catalyst, in an aqueous reaction solution, to yield a product solution comprising HMF; and
extracting the HMF into a substantially immiscible organic extraction solution, wherein the substantially immiscible organic extraction solution comprises at least one alkylphenol.
2. The process of claim 1 , wherein the at least one alkylphenol is selected from the group consisting of:
wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 24 linear, branched, or cyclic alkyl or alkene, provided that at least one of R 1 -R 5 is an alkyl group.
3. The process of claim 2 , wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 12 linear, branched, or cyclic alkyl, provided that at least one and no more than two of R 1 -R 5 is an alkyl group.
4. The process of claim 2 , wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 6 linear, branched, or cyclic alkyl, provided that at least one and no more than two of R 1 -R 5 is an alkyl group.
5. The process of claim 1 , wherein the Lewis acid catalyst is selected from the group consisting of Lewis acids comprising a lanthanoid metal, a metal from any of Groups 4, 5, 13, 14 and 15 of the periodic table of the elements, and combinations thereof; and the Brønsted acid catalyst is selected from the group consisting of mineral acids, organic acids, and heteropolyacids, and combinations thereof.
6. The process of claim 1 , wherein the aqueous reaction solution further comprises NaCl dissolved therein.
7. The process of claim 6 , wherein the aqueous reaction solution is saturated with NaCl.
8. A process to make hydroxymethylfurfural (HMF) from glucose, glucose-containing oligomers, glucose-containing polymers, or combinations thereof, the process comprising:
reacting a feedstock solution comprising glucose, glucose-containing oligomers, glucose-containing polymers, or combinations thereof, in the presence of a homogeneous Brønsted acid catalyst and a homogeneous Lewis acid catalyst, in a reaction vessel containing a biphasic reaction medium comprising an aqueous reaction solution and a substantially immiscible organic extraction solution comprising at least one alkylphenol, to yield an amount of HMF in the aqueous reaction solution, and wherein at least a portion of the HMF formed in the aqueous reaction solution is extracted into the organic extraction solution.
9. The process of claim 8 , wherein the at least one alkylphenol is selected from the group consisting of:
wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 24 linear, branched, or cyclic alkyl or alkene, provided that at least one of R 1 -R 5 is an alkyl group.
10. The process of claim 9 , wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 12 linear, branched, or cyclic alkyl, provided that at least one and no more than two of R 1 -R 5 is an alkyl group.
11. The process of claim 9 , wherein R 1 -R 5 are independently selected from the group consisting of hydrogen, hydroxyl, esters, ethers, carboxylic acids, and C 1 -C 6 linear, branched, or cyclic alkyl, provided that at least one and no more than two of R 1 -R 5 is an alkyl group.
12. The process of claim 8 , wherein the Lewis acid catalyst is selected from the group consisting of Lewis acids comprising a lanthanoid metal, a metal from any of Groups 4, 5, 13, 14 and 15 of the periodic table of the elements, and combinations thereof; and the Brønsted acid catalyst is selected from the group consisting of mineral acids, organic acids, heteropolyacids, and combinations thereof.
13. The process of claim 8 , wherein the aqueous reaction solution further comprises NaCl dissolved therein.
14. The process of claim 8 , wherein the aqueous reaction solution is saturated with NaCl.