Lignin to liquid fuels and polyols using biomass-derived solvents

Patent metadata

Field	Value
Publication number	US-11268034-B2
Application number	US-201816631116-A
Country	US
Kind code	B2
Filing date	Jul 13, 2018
Priority date	Jul 14, 2017
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

A process of producing a distillate fuel from lignin includes: preparing a biomass-derived lignin solvent; dissolving the lignin in the biomass-derived solvent; and separating undissolved lignin and mineral matter to produce a syncrude. In certain embodiments, the process further includes subjecting the syncrude to a hydrotreatment/hydrogenation process to produce a distillate fuel. A process to improve direct lignin liquefaction includes: using a non-hydrogenated lipid in a direct lignin liquefaction process to facilitate lignin depolymerization. A process for using a biomass-derived feedstock as a hydrogen donor includes: providing a biomass-derived feedstock; modifying the feedstock to improve its usefulness as a hydrogen donor; and conducting a transfer hydrogenation process using the modified feedstock as a hydrogen donor.

First claim

The invention claimed is:

1. A process of producing syncrude from lignin comprising:
preparing a biomass-derived lignin solvent comprising a hydrogen-donor solvent capable of dehydrogenating during lignin liquefaction and transferring a hydrogen atom to a lignin fragment;
mixing the lignin with the biomass-derived lignin solvent to form a slurry;
heating the slurry to dissolve the lignin by depolymerizing the lignin forming a lignin fragment, dehydrogenating the hydrogen-donor solvent and transferring the hydrogen atom to the lignin fragment in a transfer hydrogenation process to prevent re-polymerization of the lignin fragment and form a lignin-derived syncrude; and
separating undissolved lignin and mineral matter from the lignin-derived syncrude;
and wherein preparing the biomass-derived lignin solvent comprises preparing the hydrogen-donor solvent comprising at least one of:
preparing the hydrogen-donor solvent by conjugating double bonds in linoleic acid, linoleic ester, or linoleic amide and cyclizing the conjugated double bonds to form the linoleic acid, linoleic ester, or linoleic amide with an appended cyclohexene ring;
preparing the hydrogen-donor solvent by cyclizing an oleic acid, oleic ester, or oleic amide in a triglyceride to form the oleic acid, oleic ester, or oleic amide with an appended cyclohexene ring;
preparing the hydrogen-donor solvent by reacting a double bond of two fatty acids, fatty esters, or fatty amides of a triglyceride to form a cyclohexene ring between the two fatty acids, fatty esters, or fatty amides;
preparing the hydrogen-donor solvent by cyclizing fatty acids in soybean oil, a lipid from plants, or a fatty acid ester to form a modified soybean oil, lipid from plants, or fatty acid ester having a cyclohexene ring;
processing pine trees to obtain phytosterols and rosin acids;
preparing a modified hydrothermolysis oil by rapid hydrothermolysis of an oil to form a hydrothemolysis oil and modifying the hydrothermolysis oil to alter quantity and type of cyclics and aromatics; and
preparing hydrogen-donor solvent having a tetrahydrofuran diol or ester by contacting an oil having an epoxidized fatty acid or epoxidized fatty acid ester with alumina or acid to form a modified oil having the tetrahydrofuran diol or ester.

2. The process of claim 1 which further comprises subjecting the lignin-derived syncrude to at least one of a hydrotreatment process and a hydrogenation process to produce a distillate fuel.

3. The process of claim 1 wherein the lignin is dissolved without using molecular hydrogen and an added hydroliquefaction catalyst.

4. The process of claim 1 wherein an H/C atomic ratio of the syncrude is at least 5% more than that of the lignin.

5. The process of claim 1 wherein an H/C atomic ratio of the syncrude is at least 20% more than that of the lignin.

6. The process of claim 1 wherein the biomass-derived solvent additionally comprises a second solvent that helps to slurry the lignin and/or depolymerize the lignin and/or solvate the lignin.

7. The process of claim 6 wherein the second solvent is a polyunsaturated bio-based oil.

8. The process of any claim 1 further comprising:
mixing a coal-derived solvent with the biomass-derived lignin solvent to form a solvent mixture; and
wherein dissolving the lignin in the biomass-derived lignin solvent comprises dissolving the lignin and coal in the solvent mixture.

9. The process of claim 8 wherein the coal-derived solvent comprises a coal tar distillate or a portion of the syncrude produced in the process.

10. The process of claim 8 wherein the coal-derived solvent includes a portion of partially hydrotreated coal-derived syncrude.

11. The process of claim 1 wherein the hydrogen-donor solvent has a cyclic ring with one or more double bonds on the ring without being fully aromatized.

12. The process of claim 1 further comprising:
providing a biomass-derived coal solvent;
dissolving coal with the lignin in the biomass-derived lignin solvent and the biomass-derived coal solvent.

13. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises conjugating double bonds in linoleic acid, linoleic ester, or linoleic amide and cyclizing the conjugated bonds to form the linoleic acid, linoleic ester, or linoleic amide with the appended cyclohexene ring.

14. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises cyclizing the oleic acid, oleic ester, or oleic amide to form the hydrogen-donor solvent having the oleic acid, oleic ester, or oleic amide with the appended cyclohexene ring.

15. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises reacting the double bond of two fatty acids, fatty esters, or fatty amides of the triglyceride to form the cyclohexene ring between the two fatty acids, fatty esters, or fatty amides.

16. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises cyclizing fatty acids in soybean oil, the lipid from plants, or the fatty acid ester to form the modified soybean oil, lipid from plants, or fatty acid ester having a cyclohexene ring.

17. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises processing pine trees to obtain phytosterols and rosin acids.

18. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises preparing the modified hydrothermolysis oil by rapid hydrothermolysis of the oil to form the hydrothemolysis oil and modifying the hydrothermolysis oil to alter quantity and type of cyclics and aromatics.

19. The process of claim 1 wherein preparing the hydrogen-donor solvent comprises preparing the hydrogen-donor solvent having a tetrahydrofuran diol or ester by contacting the oil having an epoxidized fatty acid or epoxidized fatty acid ester with alumina or acid to form the modified oil having the tetrahydrofuran diol or ester.

20. A process of producing syncrude from lignin comprising:
preparing a biomass-derived lignin solvent comprising a hydrogen-donor solvent;
dissolving the lignin in the biomass-derived lignin solvent to form lignin-derived syncrude; and
separating undissolved lignin and mineral matter from the lignin-derived syncrude;
wherein the hydrogen-donor solvent is prepared by appending cyclohexene groups in linoleic acids to produce a modified oil.

21. A process of producing syncrude from lignin comprising:
preparing a biomass-derived lignin solvent comprising a hydrogen-donor solvent;
dissolving the lignin in the biomass-derived lignin solvent to form lignin-derived syncrude; and
separating undissolved lignin and mineral matter from the lignin-derived syncrude;
wherein the hydrogen-donor solvent is prepared by appending cyclohexene groups in oleic acids to produce a modified oil.

Assignees

• Battelle Memorial Institute

Inventors

• Chauhan Satya P
• Garbark Daniel B

Classifications

• C10G1/042

  by the use of hydrogen-donor solvents · CPC title

• C10G2300/1011

  Biomass · CPC title

• C10G2300/42

  Hydrogen of special source or of special composition · CPC title

• C10G45/32

  Selective hydrogenation of the diolefin or acetylene compounds · CPC title

• C10G1/002 Primary

  in combination with oil conversion- or refining processes · CPC title