Shell Oil Comapny

Shell Internationale Research Maatschappij, B.v.

Glenn Charles Komplin

Joseph Broun Powell

Paul Richard Weider

Kimberly Ann Johnson

John Anthony Smegal

Edward James Denton

Zaida Diaz

John F Knifton

Brendan Dermot Murray

Juben Nemchand Chheda

Robert Lawrence Blackbourn

Wayne Errol Evans

Talmadge Gail James

Duraisamy Muthusamy

Gregory John Ward

Thomas Lamar Flowers

Edward Lewis Nielsen

Stephen Edward Brewer

Douglas Lee Husen

Heejae Huh

Digestion of cellulosic biomass solids may be complicated by release of lignin therefrom. Methods for digesting cellulosic biomass solids may comprise: heating cellulosic biomass solids and a digestion solvent in the presence of molecular hydrogen and a slurry catalyst capable of activating molecular hydrogen, thereby forming a phenolics liquid phase comprising lignin, an aqueous phase comprising an alcoholic component derived from the cellulosic biomass solids, and an optional light organics phase, the slurry catalyst being distributed in the cellulosic biomass solids and at least a portion of the slurry catalyst accumulating in the phenolics liquid phase as it forms; conveying at least a portion of the phenolics liquid phase and the slurry catalyst to a location above at least a portion of the cellulosic biomass solids; and after conveying the phenolics liquid phase and the slurry catalyst, releasing them such that they come in contact with the cellulosic biomass solids.

Methods and systems for distributing a slurry catalyst in cellulosic biomass solids

Digestion of cellulosic biomass solids may be complicated by lignin release therefrom, which can produce a highly viscous phenolics liquid phase comprising lignin polymer. Methods for digesting cellulosic biomass solids may comprise: providing cellulosic biomass solids in the presence of a digestion solvent, molecular hydrogen, and a slurry catalyst capable of activating molecular hydrogen; at least partially converting the cellulosic biomass solids into a phenolics liquid phase comprising lignin, an aqueous phase comprising an alcoholic component derived from the cellulosic biomass solids, and an optional light organics phase; wherein at least a portion of the slurry catalyst accumulates in the phenolics liquid phase as it forms; and reducing the viscosity of the phenolics liquid phase.

Methods and systems for processing lignin during hydrothermal digestion of cellulosic biomass solids

Digestion of cellulosic biomass solids may be complicated by release of lignin therefrom. Methods for digesting cellulosic biomass solids may comprise: providing cellulosic biomass solids in a digestion solvent; at least partially converting the cellulosic biomass solids into a phenolics liquid phase comprising lignin, an aqueous phase comprising an alcoholic component derived from the cellulosic biomass solids, and an optional light organics phase; and separating the phenolics liquid phase from the aqueous phase.

Digesting cellulosic biomass solids in the presence of a well-distributed slurry catalyst capable of activating molecular hydrogen may limit the amount of degradation products that form during digestion. Methods for digesting cellulosic biomass solids can comprise: providing cellulosic biomass solids and a slurry catalyst in a hydrothermal digestion unit, the slurry catalyst being capable of activating molecular hydrogen; distributing the slurry catalyst within the cellulosic biomass solids using upwardly directed fluid flow in the hydrothermal digestion unit; heating the cellulosic biomass solids in the hydrothermal digestion unit in the presence of the slurry catalyst, a digestion solvent, and molecular hydrogen, thereby forming a liquor phase comprising soluble carbohydrates; and performing a first catalytic reduction reaction on the soluble carbohydrates within the hydrothermal digestion unit, thereby at least partially forming a reaction product comprising a triol, a diol, a monohydric alcohol, or any combination thereof in the hydrothermal digestion unit.

Methods for hydrothermal digestion of cellulosic biomass solids in the presence of a distributed slurry catalyst

A method of hydrothermal hydrocatalytic treating biomass is provided. Lignocellulosic biomass solids is provided to a hydrothermal digestion unit in the presence of a digestive solvent, and a supported hydrogenolysis catalyst containing (a) sulfur, (b) Mo or W, and (c) Co, Ni or mixture thereof, incorporated into an alumina support, which support is predominantly alpha alumina; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen, and supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons, said alumina support having a specific surface area of up to about 30 m/g and said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test or a crush strength of at least 0.25 kg after being subjected to an aqueous phase stability test.

Hydrothermal hydrocatalytic treatment of biomass using water tolerant catalysts

Digestion of cellulosic biomass solids can be enhanced in the presence of a phenolic solvent. Methods for digesting cellulosic biomass solids can comprise providing cellulosic biomass solids containing up to about 50% water by mass in a digestion medium comprising about 50% or more of an organic solvent by volume; heating the cellulosic biomass solids and the digestion medium in a digestion unit in the presence of molecular hydrogen and a slurry catalyst capable of activating molecular hydrogen, thereby forming an alcoholic component derived from the cellulosic biomass solids and liberating lignin therefrom; wherein the digestion medium and the water form a biphasic mixture in which the alcoholic component, slurry catalyst, and lignin are contained; removing at least a portion of the biphasic mixture from the digestion unit; converting at least a portion of the lignin into a phenolic solvent; and returning the phenolic solvent to the digestion unit.

Methods for digestion of cellulosic biomass solids in the presence of a phenolic solvent generated in situ from lignin

Digestion of cellulosic biomass solids may be complicated by release of lignin therefrom. Methods for digesting cellulosic biomass solids may comprise: providing cellulosic biomass solids in a digestion solvent; at least partially converting the cellulosic biomass solids into a phenolics liquid phase comprising lignin, an aqueous phase comprising an alcoholic component derived from the cellulosic biomass solids, and an optional light organics phase; combining at least the phenolics liquid phase and the aqueous phase with one another, thereby forming a combined phase; and separating at least a portion of the alcoholic component from at least a portion of the combined phase.

Digestion units for processing cellulosic biomass can comprise a chamber having a height that is greater than its width, the chamber having an opening suitable for solids introduction located within the upper 20% of its height; one or more first fluid conduits connected to the chamber within the lower 20% of its height, at least one of the first fluid conduits extending into the chamber and being elevated above the bottom of the chamber; one or more second fluid conduits connected to the chamber within the upper 20% of its height, at least one of the first fluid conduits being fluidly coupled to at least one of the second fluid conduits; a porous medium located in the chamber within the lower 20% of its height; and a movable pressure isolation device covering the opening; wherein the digestion unit is operable to maintain a pressure of at least about 30 bar.

Digestion units configured for high yield biomass processing

Digesting cellulosic biomass in the presence of a slurry catalyst may reduce degradation product formation, but catalyst distribution and retention can be problematic. Digestion methods can comprise: providing cellulosic biomass solids and a slurry catalyst capable of activating molecular hydrogen in a digestion unit; providing a digestible filter aid in the digestion unit; distributing the slurry catalyst within the cellulosic biomass solids using fluid flow; retaining at least a portion of the slurry catalyst in a fixed location using the digestible filter aid; heating the cellulosic biomass solids in the presence of the slurry catalyst, a digestion solvent, and molecular hydrogen, thereby forming a liquor phase comprising soluble carbohydrates; and performing a catalytic reduction reaction on the soluble carbohydrates within the digestion unit, thereby at least partially forming a reaction product comprising a triol, a diol, a monohydric alcohol, or any combination thereof in the digestion unit.

Methods for hydrothermal digestion of cellulosic biomass solids in the presence of a slurry catalyst and a digestible filter aid

A method of hydrothermal hydrocatalytic treating biomass is provided. Lignocellulosic biomass solids is provided to a hydrothermal digestion unit in the presence of a digestive solvent, and a supported hydrogenolysis catalyst containing (a) sulfur, (b) Mo or W, and (c) Co, Ni or mixture thereof, incorporated into a group 4 metal oxide support; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen, and the supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons, said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test or a crush strength of at least 0.25 kg after being subjected to an aqueous phase stability test.

The present invention provides an integrated process for producing aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons from low molecular weight alkanes, which includes contacting the low molecular weight alkanes with a halogen and coupling the monohaloalkanes to form aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons.

Integrated process to produce C4+ hydrocarbons with removal of brominated organic impurities

The invention provides a process for preparing 1,3-alkanediols, such as 1,3-propanediol (PDO), from 3-hydroxyaldehydes, such as 3-hydroxypropanal (HPA), comprising providing a mixture of 3-hydroxyaldehydes in an organic solvent; extracting into an aqueous liquid a major portion of the 3-hydroxyaldehydes to provide an aqueous phase comprising 3-hydroxyaldehydes in greater concentration than the concentration of 3-hydroxyaldehydes in the 3-hydroxyaldehyde mixture, and an organic phase; separating the aqueous phase from the organic phase; contacting the aqueous phase with hydrogen in the presence of a hydrogenation catalyst to provide a hydrogenation product mixture comprising 1,3-alkanediols and water; separating water from the 1,3-alkanediols using a multi-effect evaporation scheme; recycling water containing about 50 wt % or less 1,3-propanediol based upon the total amount of 1,3-propanediol and water to the extraction stage; and recovering 1,3-alkanediols.

Process for preparing 1,3-propanediol

A method of treating an aldehyde mixture comprising a carboxylic acid and a metal cation, which method comprises: contacting the aldehyde mixture with a basic separating medium, and subsequently or simultaneously contacting with an acidic separating medium; use of the treated aldehyde mixture to prepare an alcohol; and the alcohol.

Method of treating an aldehyde mixture, use of the treated aldehyde, and an alcohol

The present invention relates to a process for hydrogenating an aldehyde. An aldehyde is contacted with a catalyst comprising a support containing at least 95% &#x3b1;-alumina and non-support metals dispersed on the surface of the support. The non-support metals comprise nickel and/or one or more compounds thereof and molybdenum and/or one or more compounds thereof. The nickel and/or one or more compounds thereof comprise from 3 wt. % to 9 wt. % of the catalyst, by metallic weight, and the molybdenum and/or one or more compounds thereof comprise from 1 wt. % to 4 wt. % of the catalyst, by metallic weight.

Process for hydrogenating an aldehyde

The present invention provides a hydrogenation catalyst effective for hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol. The hydrogenation catalyst comprises an &#x3b1;-alumina support, nickel, ruthenium, and a promoter. The nickel is deposited on the &#x3b1;-alumina support, and the ruthenium and the promoter are deposited on the nickel and the &#x3b1;-alumina support. The &#x3b1;-alumina support comprises at least 92 wt. % of the catalyst, and the nickel comprises from 1 wt. % to 6 wt. % of the catalyst. The present invention also provides a process of hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol with the catalyst.

Growing community of inventors

Katy, TX, United States of America

Glenn Charles Komplin