Coupling high yield biochemical intermediates for fuel production
A chemical upgrading of two high-yield fermentation products to produce a novel biofuel with properties desirable for use in internal combustion engines produces a C 7 to C 22 alkoxyalkanoate corresponding to formula (I): wherein R 2 and R 1 are alkyl groups independently selected to have 2 to 18 carbon atoms; wherein the R 3 group is a C 1 to C 5 group divalent alkyl group. The alkoxyalkanoate can be used as a neat fuel or blend with biodiesel, diesel, gasoline, ethanol or other fuels. The alkoxyalkanoates have improved cloud point properties over diesel fuels. A method for making the alkoxyalkanoate from a biomass source is also disclosed.
1. A fuel for an internal combustion engine comprising:
a C 7 to C 22 alkoxyalkanoate corresponding to formula (I):
(I)
wherein R 2 and R 1 are alkyl groups independently selected to have 2 to 18 carbon atoms; and
wherein the R 3 group is a C 1 to C 5 group divalent alkyl group; and
R 1 and R 2 have a different number of carbon atoms; or
R 1 and R 2 are independently selected to have 8 to 18 carbon atoms; or
R 1 and R 2 have 1 to 3 branching methyl or ethyl or propyl groups;
wherein either or both R 1 and R 2 have a cyclic group with 3 to 6 members or 1 to 5 units of unsaturation.
2. The fuel of claim 1 , wherein R 1 and R 2 have a different number of carbon atoms.
3. The fuel of claim 1 , wherein R 1 and R 2 have 1 to 3 branching methyl or ethyl or propyl groups.
4. The fuel of claim 1 , wherein both R 1 and R 2 have a cyclic group with 3 to 6 members or 1 to 5 units of unsaturation.
5. The fuel of claim 1 , wherein one of R 1 and R 2 is a C 1 or C 2 alkyl group, and the other is a C 4 to C 8 group.
6. The fuel of claim 5 , wherein R 3 is —CH(CH 3 )—.
7. The fuel of claim 1 , wherein R 3 is —CH(CH 3 )—.
8. The fuel of claim 1 , wherein the alkoxyalkanoate is derived from a renewable biomass source.
9. The fuel of claim 1 , wherein the alkoxyalkanoate has an LHV of 25 to 40 MJ/kg.
10. The fuel of claim 1 , wherein the alkoxyalkanoate has a cloud point of −5° C. to −100° C.
11. A blended fuel for an internal combustion engine comprising:
a fuel selected from the group consisting of: gasoline, diesel, alcohol fuel, biofuel, Fischer-Tropsch fuel, or combinations thereof; and
a C 7 to C 22 alkoxyalkanoate corresponding to formula (I):
wherein R 2 and R 1 are alkyl groups independently selected to have 2 to 18 carbon atoms; and
wherein the R 3 group is a C 1 to C 5 group divalent alkyl group; and
R 1 and R 2 have a different number of carbon atoms; or
R 1 and R 2 are independently selected to have 8 to 18 carbon atoms; or
R 1 and R 2 have 1 to 3 branching methyl or ethyl or propyl groups;
wherein an effective of amount of the alkoxyalkanoate is present to lower a cloud point of the blended fuel 5 to 50° C. lower than the fuel alone.
12. The blended fuel of claim 11 , wherein the alkoxyalkanoate is present in a ratio of 99.9:0.1 to 51:49 by volume to the fuel.
13. The blended fuel of claim 12 , wherein the fuel is selected from the group consisting of diesel, biofuel, alcohol, or a combination of these.
14. The blended fuel of claim 11 , wherein the fuel is present in a ratio of 99.9:0.1 to 51:49 by volume to the alkoxyalkanoate.
15. The blended fuel of claim 14 , wherein the fuel is selected from the group consisting of diesel, biofuel, alcohol, or a combination of these.
16. The blended fuel of claim 11 , wherein the fuel is selected from the group consisting of diesel, biofuel, alcohol, or a combination of these.
17. A method for making a fuel product for an internal combustion engine at least partially from a biomass source, the method comprising:
reacting a fusel alcohol and hydroxyalkanoate in a solvent to form a hydroxyalkanoate; and
reacting the hydroxyalkanoate with an alkyl halide to form an alkoxyalkanoate;
wherein the alkoxyalkanoate is an asymmetric C 7 to C 22 alkoxyalkanoate; or a C 12 to C 22 alkoxyalkanoate; or the alkoxyalkanoate includes 1 to 3 branching methyl or ethyl or propyl groups on an ether-bound end and 1 to 3 branching methyl or ethyl or propyl groups on an ester-bound end;
further comprising the step of blending the alkoxyalkanoate with a fuel selected from the group consisting of: gasoline, diesel, alcohol fuel, biofuel, Fischer-Tropsch fuel, or combinations thereof;
wherein an effective amount of alkoxyalkanoate is blended in the blending step to lower a cloud point of the fuel product 5 to 50° C. lower than the fuel alone.
18. The method of claim 17 , further comprising adding an acid catalyst in the step of reacting a fusel alcohol and hydroxyalkanoate in a solvent to form a hydroxyalkanoate.
19. The method of claim 17 , wherein the alkoxyalkanoate corresponds to formula (I):
wherein R 2 and R 1 are alkyl groups independently selected to have 2 to 18 carbon atoms; and
wherein the R 3 group is a C 1 to C 5 group divalent alkyl group.
20. The method of claim 17 further comprising producing the hydroxyalkanoate and fusel alcohol from the biomass source through acidogenic or solvetogenic biochemical pathways in homo- or heterofermentative processes.