SixRing Inc.

One-pot processes to separate lignin from a lignocellulosic feedstock include providing a vessel; providing a lignocellulosic feedstock; providing a composition comprising an acid, a modifying agent comprising an alkanesulfonic acid, and a peroxide; and exposing the lignocellulosic feedstock to the composition in the vessel for a period of time sufficient to remove at least 80% of the lignin present in the lignocellulosic feedstock. In some instances, such one-pot process can further include removing a liquid phase comprising dissolved lignin fragments from a solid phase comprising cellulose fibres.

One-pot processes to separate lignin from a lignocellulosic feedstock include providing a vessel; providing a lignocellulosic feedstock; providing an aqueous composition comprising an acid, a modifying agent comprising a substituted aromatic compound, and a peroxide; and exposing the lignocellulosic feedstock to the composition in the vessel for a period of time sufficient to remove at least 80% of the lignin present in the lignocellulosic feedstock.

Method to produce biofuel using a lignin-rich feedstock, said method comprise; —providing a lignin-rich feedstock, wherein said lignin-rich feedstock comprises more than 60 wt % of lignin-based compounds obtained from delignification of biomass, where said lignin-based compounds are selected from the group consisting of: lignin-derived monomers, lignin-derived dimers, lignin-derived oligomers and combinations thereof; —performing a hydrodeoxygenation reaction on said lignin-rich feedstock, wherein the hydrodeoxygenation reaction is carried out in a hydrogen-rich source at a temperature ranging from 300° C. to 400° C. under a H2 pressure ranging from 15 to 75 bar, more preferably 35 bar, in the presence of a catalyst adapted for HDO reactions, for a period of time sufficient to result in an upgraded oil having a total acid number (TAN) of about 10-35 mg KOH/g and viscosity of 4-30 cP.

A method for obtaining alpha-cellulose in a purity of above 85%, where said method comprises the following steps: Step 1: providing a biomass feedstock comprising: cellulose; hemicellulose; and lignin; Step 2: exposing the biomass feedstock to a delignification step performed using a modified Caro's acid creating a reaction mixture, wherein said delignification is carried out at a temperature ranging 20-40° C. for a period of time sufficient to allow the modified Caro's acid to delignify said lignocellulosic biomass and yield: a remaining solids portion having a kappa number of less than 10; and a liquid stream; Step 4: removing said liquid stream comprising depolymerized lignin and depolymerized hemicellulose from the resulting reaction mixture; Step 5: recovering said remaining solids portion comprising high purity cellulosic portion.

A method for substantially removing constituents of a lignocellulosic biomass into separate streams, where said method comprises the following steps: Step 1: providing said lignocellulosic biomass comprising: cellulose; hemicellulose; and lignin; Step 2: exposing the lignocellulosic biomass to a delignification step performed at a temperature below 55° C. using a modified Caro's acid and generating a reaction mixture, said delignification step is carried out for a first period of time sufficient to dissolve enough of the lignin present in said lignocellulosic biomass to obtain a kappa number for the remaining solids of less than 10; Step 4: recovering, from the reaction mixture, a liquid stream comprising depolymerized lignin constituents and said remaining solids comprising cellulose and hemicellulose and having a lignin content of less than 1.5% lignin; Step 5: exposing said remaining solids to a caustic composition at a low temperature, (preferably below 60° C.), to generate a caustic mixture comprising said caustic composition, hemicellulose and cellulose; Step 6: allowing sufficient time for at least 85% of the remaining hemicellulose present to be dissolved by said caustic composition, and wherein exposure to said caustic composition yields a final solids portion; Step 6: optionally, separating said dissolved hemicellulose from said final solids portion; and Step 7: optionally, recovering said final solid portion; and Step 8: recovering said hemicellulose from said dissolved hemicellulose, wherein said hemicellulose recovered constitutes over 85% of the hemicellulose present in said remaining solids portion and is mainly in a polysaccharide form.

A process to manufacture nanocrystalline cellulose from a cellulose having a low hemicellulose content, said process comprising the steps of: exposing said cellulose to a solution comprising a microemulsion for a first pre-determined period of time, thereby creating a cellulose suspension comprising said microemulsion and a swollen cellulose; optionally, separating said microemulsion from said swollen cellulose; exposing said swollen cellulose to a source of peroxide (such as H 2 O 2 ) and a metal salt selected from the group consisting of: FeSO 4 ; CuSO 4 ; and combinations thereof, under acidic conditions, for a second pre-determined period causing hydrolysis of the cellulose; and recovering a resulting nanocrystalline cellulose, wherein the cellulose has a particle size ranging from 100 to 1000 μm.

A modified aqueous acid composition comprising: sulfuric acid; a compound comprising an amine moiety and a sulfonic acid moiety; and a peroxide; wherein sulfuric acid, said compound comprising an amine moiety and a sulfonic acid moiety and said peroxide are present in a molar ratio of no less than 1:1:1. Also disclosed are methods of using such compositions.

Method of delignification of plant material, said method comprising: providing said plant material comprising cellulose fibers and lignin; exposing said plant material requiring to a composition comprising: alkanesulfonic acid; and a peroxide, wherein said alkylsulfonic acid and peroxide are present in a molar ratio ranging 1:1 to 15:1 and the time of exposure is sufficient to remove substantially all of the lignin present on said plant material. Compositions capable of achieving delignification are also disclosed.

A one-pot process to separate lignin from a lignocellulosic feedstock includes providing a vessel; providing a lignocellulosic feedstock; providing a composition comprising an acid, a modifying agent comprising a carbonyl-containing nitrogenous base compound, and a peroxide; exposing the lignocellulosic feedstock to the composition in the vessel for a period of time sufficient to remove at least 80% of the lignin present in the lignocellulosic feedstock; and optionally, removing a liquid phase comprising dissolved lignin fragments from a solid phase comprising cellulose fibres.

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 capping agent; and a peroxide; for a period of time sufficient to remove substantially all (at least 80%) of the lignin present on said plant material. Also disclosed are compositions to accomplish such delignification and processes using such.