Production of liquid alkanes in the jet fuel range (C8-C15) from biomass-derived carbohydrates

A method for making alkanes comprising:

• (a) converting a carbohydrate reactant to yield at least one carbonyl compound having an alpha-position hydrogen, in the presence of an acid catalyst, in a reaction vessel containing a biphasic reaction medium comprising an aqueous reaction solution and a substantially immiscible organic extraction solution, wherein the aqueous reaction solution, the organic extraction solution, or both the aqueous reaction solution and the organic extraction solution contain at least one modifier to improve selectivity of the process to yield the carbonyl compound having an alpha-position hydrogen;
• then
• (b) subjecting the carbonyl compound of step (a) to at least one self-aldol condensation reaction or a crossed-aldol condensation reaction in an aqueous monophasic or an aqueous/organic biphasic reaction medium with another carbonyl compound to yield a beta-hydroxy carbonyl compound and/or an alpha-beta unsaturated carbonyl compound;
• then
• (c) hydrogenating the beta-hydroxy carbonyl and/or the alpha-beta unsaturated carbonyl compounds of step (b) to yield a saturated or partially saturated compound;
• and then
• (d) hydrodeoxygenating the saturated or partially saturated compound of step (c) to yield an alkane.

A method for making alkanes comprising:

• (a) dehydrating a C6 sugar to yield hydroxymethylfurfural, in the presence of an acid catalyst, in a reaction vessel containing a biphasic reaction medium comprising an aqueous reaction solution and a substantially immiscible organic extraction solution, wherein the aqueous reaction solution, the organic extraction solution, or both the aqueous reaction solution and the organic extraction solution contain at least one modifier to improve selectivity of the dehydration to yield hydroxymethylfurfural;
• then
• (b) subjecting the hydroxymethylfurfural to at least one crossed-aldol condensation reaction in an aqueous monophasic or an aqueous/organic biphasic reaction medium with an aldehyde or a ketone to yield a beta-hydroxy carbonyl and/or an alpha-beta unsaturated carbonyl having at least seven (7) carbon atoms;
• then
• (c) hydrogenating the beta-hydroxy carbonyl and/or alpha-beta unsaturated carbonyl to yield a saturated or partially saturated compound;
• and then
• (d) hydrodeoxygenating the saturated or partially saturated compound to yield an alkane having at least seven (7) carbon atoms.

A method for making a liquid transportation fuel, the method comprising:

• (a) dehydrating a feedstock solution comprising a carbohydrate, in the presence of an acid catalyst, to yield at least one carbonyl compound, in a reaction vessel containing a biphasic reaction medium comprising an aqueous reaction solution and a substantially immiscible organic extraction solution, wherein the aqueous reaction solution, the organic extraction solution, or both the aqueous reaction solution and the organic extraction solution contain at least one modifier to improve selectivity of the dehydration to yield the carbonyl compound;
• then
• (b) subjecting a carbonyl compound of step (a) to at least one self-aldol condensation reaction or a crossed-aldol condensation reaction in an aqueous monophasic or an aqueous/organic biphasic reaction medium with another carbonyl compound to yield a beta-hydroxy carbonyl compound and/or an alpha-beta unsaturated carbonyl compound;
• then
• (c) hydrogenating the beta-hydroxy carbonyl and/or alpha-beta unsaturated compounds of step (b) to yield a saturated or partially saturated compound;
• and then
• (d) hydrodeoxygenating the saturated or partially saturated compound to yield a composition of matter comprising alkanes, wherein the composition of matter is dimensioned and configured for use as a liquid transportation fuel.