# US 11,028,249 B2 · Methods of synthesizing ionic liquids from primary alcohol-containing lignin compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,028,249 B2 - Document ID: US11028249B2 - Status: Granted - Kind: B2 - Application number: 16/119,866 - Filed: 2018-08-31 - Published: 2019-02-28 - Granted: 2021-06-08 - Earliest claimed: 2017-08-31 - Assignees: National Technology & Engineering Solutions of Sandia, LLC - Applicants: National Technology & Engineering Solutions of Sandia, LLC - Inventors: Tanmoy Dutta; Blake Simmons; Seema Singh - Web page: https://patentgrep.com/patent/US11028249B2 ## CPC - C08J 11/28: by treatment with organic compounds containing nitrogen, sulfur or phosphorus - C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms - C07C 209/00: Preparation of compounds containing amino groups bound to a carbon skeleton - C07C 209/08: with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings - C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids} - C08J 11/16: by treatment with inorganic material (C08J11/14 takes precedence) - C08L 97/005: {Lignin} - C08L 97/02: Lignocellulosic material, e.g. wood, straw or bagasse {(manufacture of articles made from lignocellulosic material by dry processes B27N)} - C08J 11/10: by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation (depolymerisation to the original monomer C07) - C08J 2397/02: Lignocellulosic material, e.g. wood, straw or bagasse - Y02W 30/62: Plastics recycling; Rubber recycling - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT ## Abstract Methods and compositions are provided for synthesizing ionic liquids from lignin. Methods and compositions are also provided for treating lignin with ionic liquids. ## Claims ### Claim 1 A method for preparing an ionic liquid comprising: (i) contacting a lignin-derived aromatic starting material with a halogenating agent in a non-polar solvent, an aprotic solvent, or a combination thereof under conditions sufficient to form a lignin-derived aromatic halide; (ii) contacting the lignin-derived aromatic halide with an amine under conditions sufficient to form a lignin-derived aromatic amine; and (iii) contacting the lignin-derived aromatic amine with an acid under conditions sufficient to form a lignin-derived aromatic ammonium salt, thereby preparing the ionic liquid. ### Claim 2 (depends on 1) The method of claim 1, wherein the lignin-derived aromatic starting material comprises a primary alcohol. ### Claim 3 (depends on 1) The method of claim 1, wherein the lignin-derived aromatic starting material comprises one or more components selected from the group consisting of depolymerized lignin monomers, oligomeric lignin, polymeric lignin, and lignocellulose. ### Claim 4 (depends on 3) The method of claim 3, further comprising depolymerizing lignin to obtain the depolymerized lignin monomers, the oligomeric lignin, or a combination thereof. ### Claim 5 (depends on 3) The method of claim 3, wherein the depolymerized lignin monomers comprise one or more components selected from the group consisting of modified phenols, modified anisoles, modified guaiacols, modified veratroles, modified catechols, and modified syringols. ### Claim 6 (depends on 5) The method of claim 5, wherein the modified anisole is (4-methoxyphenyl)methanol. ### Claim 7 (depends on 1) The method of claim 1, wherein the lignin-derived aromatic starting material comprises one or more components selected from the group consisting of sinapyl alcohol, coniferyl alcohol, and p-coumaryl alcohol. ### Claim 8 (depends on 1) The method of claim 1, wherein the halogenating agent is selected from the group consisting of hydrogen chloride, thionyl chloride, phosphorus trichloride, phosphorus pentachloride, hydrogen bromide, thionyl bromide, phosphorus tribromide, phosphorus pentabromide, and phosphorus triiodide. ### Claim 9 (depends on 1) The method of claim 1, wherein the lignin-derived aromatic halide is contacted with from about 1 to about 6 molar equivalents of the amine. ### Claim 10 (depends on 1) The method of claim 1, wherein the amine is a secondary amine or a tertiary amine. ### Claim 11 (depends on 10) The method of claim 10, wherein the secondary amine is a dialkyl amine. ### Claim 12 (depends on 10) The method of claim 10, wherein the tertiary amine is a trialkyl amine. ### Claim 13 (depends on 1) The method of claim 1, wherein step (i) and step (ii) is conducted at a temperature independently ranging from about 0° C. to about 25° C. ### Claim 14 (depends on 1) The method of claim 1, wherein step (iii) is conducted at a temperature ranging from about 0° C. to about 25° C. ### Claim 15 (depends on 1) The method of claim 1, wherein at least one of step (i), step (ii), and step (iii) is conducted for at least 6 hours. ### Claim 16 (depends on 1) The method of claim 1, wherein the lignin-derived aromatic amine is contacted with from about 1 to about 2 molar equivalents of the acid. ### Claim 17 (depends on 1) The method of claim 1, wherein the acid is selected from the group consisting of acetic acid, sulfuric acid, and phosphoric acid. ### Claim 18 (depends on 1) The method of claim 1, wherein the contacting steps are performed in a single reaction vessel. ### Claim 19 (depends on 1) An ionic liquid prepared by the method of claim 1. ### Claim 20 (depends on 1) The method of claim 1, wherein the non-polar solvent is selected from the group consisting of diethyl ether, dioxane, and chloroform, and wherein the aprotic solvent is selected from the group consisting of dichloromethane, tetrahydrofuran, and acetonitrile.