Fischer Esterification of Lignin-Derived Material

    公开(公告)号:US20250042834A1

    公开(公告)日:2025-02-06

    申请号:US18793609

    申请日:2024-08-02

    Applicant: SixRing Inc.

    Abstract: A method for converting a lignin-derived material into at least one esterified lignin derivative, said method comprising the steps of: providing said lignin-derived material selected from the group consisting of: lignin monomers; lignin depolymerization products; and combinations thereof; providing an acidic composition having a pH of less than 1, said acidic composition comprising: an acid selected from the group consisting of: sulfuric acid; an alkylsulfonic acid; and an arylsulfonic acid; and an alcohol selected from the group consisting of C1-C8 linear alcohol and C3-C8 branched alcohol and mixtures thereof; combining said lignin-derived material with said acidic composition into a reaction mixture; heating up said mixture to a temperature ranging from 25° C. to 120° C.; and allowing sufficient time of reaction to convert at least a portion of said lignin-derived material into said at least one esterified lignin derivative.

    COMBINATION APPROACH TO DELIGNIFICATION OF BIOMASS UNDER AMBIENT CONDITIONS

    公开(公告)号:US20220186434A1

    公开(公告)日:2022-06-16

    申请号:US17404199

    申请日:2021-08-17

    Applicant: SixRing Inc.

    Abstract: Method of delignification of plant material, said method comprising: providing said plant material comprising cellulose fibres and lignin; exposing said plant material requiring to a composition comprising: an acid; a modifying agent selected from the group consisting of: sulfamic acid; imidazole; N-alkylimidazole derivative; taurine; a taurine derivative; a taurine-related compound; alkylsulfonic acid; arylsulfonic acid; triethanolamine; and combinations thereof; a metal oxide; and a peroxide; adding an organic solvent to the resulting mixture; allowing a delignification reaction to occur for a period of time sufficient to remove at least 80% of the lignin present on said plant material.

    IMPROVEMENTS IN BIOMASS DELIGNIFICATION
    5.
    发明公开

    公开(公告)号:US20240209159A1

    公开(公告)日:2024-06-27

    申请号:US18392952

    申请日:2023-12-21

    Applicant: SixRing Inc.

    CPC classification number: C08H8/00 C08H6/00

    Abstract: A method for removing the constituents of a biomass into separate streams, where said method comprises the following steps:



    Step 1: providing a biomass feedstock comprising: cellulose; hemicellulose; and lignin;
    Step 2: exposing said biomass to a first acidic composition comprising an acid selected from the group consisting of: mineral acids; organic acids; modified acids; synthetic acids; and combinations thereof; for a first period of time sufficient to dissolve at least 50% of the hemicellulose present in said biomass;
    Step 3: separating and recovering into a first liquid stream, the dissolved hemicellulose from the remaining biomass;
    Step 4: exposing the remaining biomass mixture to a modified Caro's acid selected from the group consisting of:

    composition A; composition B and Composition C;
    wherein said composition A comprises:

    sulfuric acid in an amount ranging from 20 to 70 wt % of the total weight of the composition;
    a compound comprising an amine moiety and a sulfonic acid moiety selected from the group consisting of: taurine; taurine derivatives; and taurine-related compounds; and
    a peroxide;


    wherein said composition B comprises:

    an alkylsulfonic acid; and
    a peroxide; wherein the acid is present in an amount ranging from 40 to 80 wt % of the total weight of the composition and where the peroxide is present in an amount ranging from 10 to 40 wt % of the total weight of the composition;


    wherein said composition C comprises:

    sulfuric acid;
    a compound comprising an amine moiety;
    a compound comprising a sulfonic acid moiety; and
    a peroxide;


    for a first period of time sufficient to dissolve enough of the lignin present in said remaining biomass mixture to obtain a kappa number for the cellulose of less than 5;
    for a first period of time sufficient to dissolve enough of the lignin present in said remaining biomass mixture to obtain a kappa number for the cellulose of less than 5;


    Step 5: recovering into a second liquid stream the dissolved lignin from the resulting reaction mixture, wherein said solid portion comprises cellulose fibers with, at most, 7.5 wt % hemicellulose.

    NOVEL APPROACH TO BIOMASS DELIGNIFICATION

    公开(公告)号:US20220195665A1

    公开(公告)日:2022-06-23

    申请号:US17405029

    申请日:2021-08-18

    Applicant: SixRing Inc.

    Abstract: Method of delignification of plant material, said method comprising: providing said plant material comprising cellulose fibres and lignin; exposing said plant material requiring to a composition comprising: an acid; a modifying agent selected from the group consisting of: sulfamic acid; imidazole; taurine; a taurine derivative; a taurine-related compound; alkylsulfonic acid; aryl sulfonic acid; triethanolamine; and combinations thereof; a metal salt; and a peroxide; for a period of time sufficient to remove substantially all (at least 80%) of the lignin present on said plant material.

    USE OF A MODIFIED ACID IN DUAL PURPOSE BIOMASS DELIGNIFICATION

    公开(公告)号:US20250043507A1

    公开(公告)日:2025-02-06

    申请号:US18793649

    申请日:2024-08-02

    Applicant: SixRing Inc.

    Abstract: Method for controlled delignification of lignocellulosic feedstock and conversion of lignin depolymerization products into at least one ester compound, said method comprising the steps of: providing an acidic composition having a pH of less than 1, said acidic composition comprising: an acid selected from the group consisting of: sulfuric acid; an alkylsulfonic acid; and an arylsulfonic acid; a source of peroxide; an alcohol selected from the group consisting of C1-C6 linear alcohol and C3-C6 branched alcohol and mixtures thereof; exposing said lignocellulosic feedstock to said acidic composition for a period of time sufficient for the acidic composition to react with the lignocellulosic feedstock to obtain a liquid phase containing lignin depolymerization products and diester compounds and a solid phase comprising cellulose fibers; optionally, separating the liquid phase from the solid phase recovering a mixture of diesters, lignin monomers and cellulose fibers; and optionally, separating said lignin depolymerization products from said diester compounds.

    APPROACH TO BIOMASS DELIGNIFICATION

    公开(公告)号:US20220195664A1

    公开(公告)日:2022-06-23

    申请号:US17405028

    申请日:2021-08-18

    Applicant: SixRing Inc.

    Abstract: A process to separate lignin from a lignocellulosic feedstock, said process comprising the steps of: providing said lignocellulosic feedstock; providing a composition comprising; an acid; a modifying agent selected from the group consisting of: sulfamic acid; imidazole; imidazole derivatives; taurine; a taurine derivative; a taurine-related compound; alkylsulfonic acid; arylsulfonic acid; triethanolamine; and combinations thereof; a peroxide salt; and a peroxide; exposing said lignocellulosic feedstock to said composition for a period of time sufficient to depolymerize substantially all of the lignin present in said lignocellulosic feedstock into lignin oligomers and lignin monomers; wherein said process is carried out at atmospheric pressure.

    NOVEL APPROACH TO BIOMASS DELIGNIFICATION

    公开(公告)号:US20220186436A1

    公开(公告)日:2022-06-16

    申请号:US17405031

    申请日:2021-08-18

    Applicant: SixRing Inc.

    Abstract: Method of delignification of plant material, said method comprising: providing said plant material comprising cellulose fibres and lignin; exposing said plant material requiring to a composition comprising: an acid; a modifiying agent selected from the group consisting of: sulfamic acid; imidazole; N-alkylimidazole; taurine; a taurine derivative; a taurine-related compound; alkylsulfonic acid; arylsulfonic acid; triethanolamine; and combinations thereof; a metal oxide; and a peroxide; for a period of time sufficient to remove substantially all (at least 80%) of the lignin present on said plant material.

    USE OF A 2 LIQUID PHASE SYSTEM IN BIOMASS DELIGNIFICATION

    公开(公告)号:US20220186435A1

    公开(公告)日:2022-06-16

    申请号:US17405027

    申请日:2021-08-18

    Applicant: SixRing Inc.

    Abstract: Method for controlled delignification of lignocellulosic feedstock, said method comprising the steps of: providing a reactive phase of pH less than 1, said reactive phase comprising: water; sulfuric acid; a source of peroxide; a modifying agent, said modifying agent adapted to control the reactivity of the sulfuric acid; providing a holding phase, said holding phase comprising an organic solvent which does not react with the aqueous acidic composition; combining said reactive phase and holding phase to form a reaction mixture; exposing a lignocellulosic material to said reaction mixture for a period of time sufficient to allow delignification of the lignocellulosic material.

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