Conversion of oligomeric starch, cellulose, hydrolysates or sugars to hydrocarbons
Embodiments of the present invention are directed to the conversion of a source material (e.g., a depolymerized oligosaccharide mixture, a monomeric sugar, a hydrolysate, or a mixture of monomeric sugars) to intermediate molecules containing 7 to 26 contiguous carbon atoms. These intermediates may also be converted to saturated hydrocarbons. Such saturated hydrocarbons are useful as, for example, fuels.
1. A process of preparing a saturated hydrocarbon comprising:
combining a source material with a dicarbonyl under conditions suitable to form an intermediate mixture, the source material comprising a depolymerized oligosaccharide mixture, a monomeric sugar, a hydrolysate, or a mixture of monomeric sugars; and
adding hydrogen and a hydrogenation catalyst to the intermediate mixture under conditions suitable to form the saturated hydrocarbon.
2. The process of claim 1 , wherein the dicarbonyl is methyl acetoacetate, ethyl acetoacetate, i-propyl acetoacetate, 2,4-pentanedione, n-propyl acetoacetate, malonate esters, cyanoacetates, or a mixture thereof.
3. The process of claim 2 , wherein the dicarbonyl is 2,4-pentanedione.
4. The process of claim 1 , wherein the saturated hydrocarbon is 3-ethylnonane.
5. The process of claim 1 , wherein the hydrogenation catalyst is palladium/carbon or nickel.
6. The process of claim 1 , wherein the source material comprises a depolymerized oligosaccharide mixture, and the depolymerized oligosaccharide mixture is prepared by heating an oligosaccharide for a time sufficient to form the depolymerized oligosaccharide mixture.
7. The process of claim 6 , wherein the heating is achieved using microwave radiation.
8. The process of claim 6 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is under acidic conditions.
9. The process of claim 8 , wherein the acidic conditions are achieved using hydrochloric acid, triflic acid, acetic acid, trifluoroacetic acid, or a combination thereof.
10. The process of claim 6 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is conducted in the presence of a Lewis acid catalyst or a Bronsted acid catalyst.
11. The process of claim 10 , wherein the Lewis acid catalyst or the Bronsted acid catalyst is cerium chloride, iron chloride, lanthanum triflate, iron triflate, or a mixture thereof.
12. The process of claim 1 , wherein the combining of the source material with the dicarbonyl is conducted in the presence of a Lewis acid catalyst or a Bronsted acid catalyst.
13. The process of claim 12 , wherein the Lewis acid catalyst or the Bronsted acid catalyst is cerium chloride, iron chloride, lanthanum triflate, iron triflate, or a mixture thereof.
14. The process of claim 1 , wherein the source material comprises a hydrolysate, the hydrolysate comprising a mixture of two or more sugars.
15. The process of claim 14 , wherein the mixture of two or more sugars comprises a mixture of two or more of glucose, xylose, arabinose, cellobiose, galactose and/or fructose.
16. The process of claim 14 , wherein the hydrolysate further comprises one or more acids.
17. The process of claim 16 , wherein the one or more acids comprises one or more of lactic acid, glycerol, ethanol, acetic acid, ethanol, furfural and/or hydroxymethylfurfural (HMF).
18. The process of claim 1 , wherein the monomeric sugar comprises glucose or xylose.
19. The process of claim 1 , wherein the mixture of monomeric sugars comprises at least glucose and xylose.