Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons

A method of making a C4+ compound comprising:

• providing water and a water soluble oxygenated hydrocarbon comprising a C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase,
• catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2,
• catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon in a reaction stream, and
• catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound,
• wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.

A method of making a C4+ compound comprising:

• providing an aqueous solution comprising water and a member selected from the group consisting of a sugar, furfural, carboxylic acid, ketone, furan, and a combination thereof;
• catalytically reacting in a liquid and/or vapor phase the sugar, furfural, carboxylic acid, ketone, furan, or combination thereof, with H2 in the presence of a hydrogenation catalyst at a hydrogenation temperature and hydrogenation pressure to produce an oxygenated hydrocarbon comprising a C1+O1-3 hydrocarbon,
• catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2,
• catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon, and
• catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound,
• wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.

A method of making a C4+ compound comprising:

• providing an aqueous solution comprising water and a member selected from the group consisting of a polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, sugar, sugar alcohol, and a combination thereof;
• catalytically reacting in a liquid and/or vapor phase the sugar, sugar alcohol, polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, or combination, with H2 in the presence of a hydrogenolysis catalyst at a hydrogenolysis temperature and hydrogenolysis pressure to produce an oxygenated hydrocarbon comprising a C1+O1+ hydrocarbon,
• catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2,
• catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon, and
• catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound,
• wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.