Composition and process of making bio-based upcycled oils in flow reactors

A method of making compounds having the following structures:

• wherein R is methyl, npropyl, nhexyl, nbutyl, n-pentyl, or nundecyl and R1 is independently selected from H or an alkyl chain of carbon number 1-7
• wherein the method comprises of the steps of:
• (a) an acid catalyzed condensation reaction of a first component comprising one of more of a 2-alkylfuran wherein the alkyl group is independently selected from carbon number of 1 to 7, with a second component comprising an aldehyde having the formula of O═CH—R wherein R is methyl, npropyl, nhexyl, nbutyl, n-pentyl, or nundecyl, to produce a condensation compound,
• (b) optionally selective hydrogenation of the condensation compound in the presence of a hydrogenation catalyst to obtain a hydrogenated saturated or ring-opened hydroxyl compound,
• (c) selective hydrodeoxygenation of the condensation compound or the hydrogenated saturated or ring-opened hydroxyl compound, in the presence of a hydrodeoxygenation catalyst to obtain a branched alkane compound.

A method of making compounds having the structure:

• wherein R1 is independently selected from alkyl groups of carbon number 2 to 14, R is independently selected from H or —(CH2)4 group,
• wherein the method comprises of the steps of:
• (a) a base catalyzed condensation reaction of a third component comprising one of more of a ketone of molecular formulae (R1)(R1) C═O wherein R1 is independently selected from alkyl groups of carbon number from 2 to 14, with furfural to produce compounds of structure (i):
• wherein R is H or a furan ring,
• (b) optionally selective hydrogenation of the condensation compound in the presence of a hydrogenation catalyst to obtain furan rings saturated intermediate or ring-opened hydroxyl product to produce compounds of structure (ii):
• wherein and R2 is H or —(CH2)3CH2OH group
• (c) selective hydrodeoxygenation of the condensation compound of structure (i) or the hydrogenated saturated or ring-opened hydroxyl intermediate of structure (ii) in the presence of a hydrodeoxygenation catalyst to obtain a branched alkane compound of structure (iii).