# US 2018/0022877 A1 · Methods of producing stable lignin phenolic oil > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2018/0022877 A1 - Document ID: US20180022877A1 - Status: Published application - Kind: A1 - Application number: 15/657,678 - Filed: 2017-07-24 - Published: 2018-01-25 - Earliest claimed: 2016-07-22 - Applicants: Iowa State University Research Foundation, Inc. - Inventors: Robert C. BROWN; Marjorie R. ROVER; Patrick H. HALL; Ryan G. SMITH - Web page: https://patentgrep.com/patent/US20180022877A1 ## CPC - C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids} - C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10) ## Abstract The present invention relates to a method of producing a stable lignin phenolic oil, where the method comprises providing a lignin; pre-treating the lignin with a base solution, where the base solution has a pH of 8 or above; and hydrogenating the pre-treated lignin to produce a stabilized lignin phenolic oil. The present invention further relates to a method of producing a stable lignin phenolic oil, the method comprising: providing a non-recalcitrant lignin; solubilizing the lignin in a solvent; and hydrogenating the solubilized lignin to produce a stabilized lignin phenolic oil. ## Claims ### Claim 1 A method of producing a stable lignin phenolic oil, said method comprising: providing a lignin; pre-treating the lignin with a base solution, wherein the base solution has a pH of 8 or above; and hydrogenating the pre-treated lignin to produce a stabilized lignin phenolic oil. ### Claim 2 (depends on 1) The method of claim 1, wherein the base solution has a pH of between 8 and 11. ### Claim 3 (depends on 1) The method of claim 1, wherein the lignin is selected from the group consisting of organosolv lignin, Kraft lignin, supercritical hydrolysis lignin, steam explosion lignin, enzymatic hydrolysis lignin, acetosolv lignin, milled wood lignin, and black liquor lignin. ### Claim 4 (depends on 1) The method of claim 1, wherein said pre-treating the lignin with a base solution is carried out at a temperature of between 15° C. to 200° C. and for a time of no less than 15 minutes. ### Claim 5 (depends on 4) The method of claim 4, wherein said pre-treating is carried out at a temperature of between 100° C. to 150° C. and for a time of between 2 hours and 6 hours. ### Claim 6 (depends on 1) The method of claim 1, wherein the base solution is a hydroxide solution. ### Claim 7 (depends on 6) The method of claim 6, wherein the hydroxide is selected from the group consisting of sodium hydroxide, ammonium hydroxide, calcium hydroxide, triethylamine hydroxide, potassium hydroxide, lithium hydroxide, and magnesium hydroxide. ### Claim 8 (depends on 1) The method of claim 1, wherein the base solution has a base concentration of between 1% to 25%. ### Claim 9 (depends on 8) The method of claim 8, wherein the base solution has a base concentration of about 5% or about 10%. ### Claim 10 (depends on 1) The method of claim 1 further comprising: treating the lignin or lignin phenolic oil with an agent selected from the group consisting of triethylamine, sodium carbonate, sodium bicarbonate, alcohols, and boric acid. ### Claim 11 (depends on 1) The method of claim 1, wherein said hydrogenating is carried out at a temperature of less than 150° C. and at a pressure of less than 100 bar (absolute). ### Claim 12 (depends on 11) The method of claim 11, wherein said hydrogenating is carried out at a temperature of 10° C. to 100° C. ### Claim 13 (depends on 11) The method of claim 11, wherein said hydrogenating is carried out at a pressure of 0.05 bar (absolute) to 50 bar (absolute). ### Claim 14 (depends on 11) The method of claim 11, wherein said hydrogenating is carried out at a temperature of 15° C. to 50° C. and a pressure of 0.5 bar (absolute) to 10 bar (absolute). ### Claim 15 (depends on 11) The method of claim 11, wherein said hydrogenating is carried out at a temperature of 20° C. to 25° C. and a pressure of about 1 bar (absolute). ### Claim 16 (depends on 1) The method of claim 1, wherein said hydrogenating is carried out in the presence of a catalyst selected from the group consisting of Pd, Ru, Ru+Pd, Pt, Raney Ni, Ni, CoMo, and NiMo. ### Claim 17 (depends on 16) The method of claim 16, wherein the catalyst is Pd. ### Claim 18 (depends on 16) The method of claim 16, wherein the catalyst is Pd on activated carbon (Pd/C). ### Claim 19 (depends on 1) The method of claim 1, wherein the stabilized lignin phenolic oil contains a reduced number of polymeric ether bonds compared to the lignin prior to said pre-treating the lignin. ### Claim 20 (depends on 1) The method of claim 1, wherein the stabilized lignin phenolic oil includes methyl and methylene groups, methylene groups and aliphatic alcohols, methyl- and benzyl-substituted aromatics and alpha carbonyls, and aliphatic protons adjacent to oxygen. ### Claim 21 A method of producing a stable lignin phenolic oil, said method comprising: providing a non-recalcitrant lignin; solubilizing the lignin in a solvent; and hydrogenating the solubilized lignin to produce a stabilized lignin phenolic oil. ### Claim 22 (depends on 21) The method of claim 21, wherein the solvent is selected from group consisting of a C1 to C6 alcohol and a C2 to C6 ether. ### Claim 23 (depends on 22) The method of claim 22, wherein the solvent is selected from the group consisting of methanol and 1,4-dioxane. ### Claim 24 (depends on 21) The method of claim 21, wherein said hydrogenating is carried out at a temperature of less than 150° C. and at a pressure of less than 100 bar (absolute). ### Claim 25 (depends on 24) The method of claim 24, wherein said hydrogenating is carried out at a temperature of 10° C. to 100° C. ### Claim 26 (depends on 24) The method of claim 24, wherein said hydrogenating is carried out at a pressure of 0.05 bar (absolute) to 50 bar (absolute). ### Claim 27 (depends on 24) The method of claim 24, wherein said hydrogenating is carried out at a temperature of 15° C. to 50° C. and a pressure of 0.5 bar (absolute) to 10 bar (absolute). ### Claim 28 (depends on 24) The method of claim 24, wherein said hydrogenating is carried out at a temperature of 20° C. to 25° C. and a pressure of about 1 bar (absolute). ### Claim 29 (depends on 21) The method of claim 21, wherein said hydrogenating is carried out in the presence of a catalyst selected from the group consisting of Pd, Ru, Ru+Pd, Pt, Raney Ni, Ni, CoMo, and NiMo. ### Claim 30 (depends on 29) The method of claim 29, wherein the catalyst is Pd. ### Claim 31 (depends on 29) The method of claim 29, wherein the catalyst is Pd on activated carbon (Pd/C). ### Claim 32 (depends on 21) The method of claim 21, wherein the stabilized lignin phenolic oil contains a reduced number of polymeric ether bonds compared to the lignin prior to said solubilizing the lignin. ### Claim 33 (depends on 21) The method of claim 21, wherein the stabilized lignin phenolic oil contains methyl and methylene groups, methylene groups and aliphatic alcohols, methyl- and benzyl-substituted aromatics and alpha carbonyls, and aliphatic protons adjacent to oxygen.