Texaco Inc.

Chevron U.s.a. Inc.

Texaco Inc. & Texaco Development Corporation

Douglas G Naae

Lawrence E Whittington

Francis E Debons

Dan Edward Kieke

Alexander E Kuperman

William L Schinski

Jinyi Han

Will A Ledoux

Centha A Davis

Varadarajan Dwarakanath

Taimur Malik

Gregory Arthur Winslow

James F Stevens

Mukund Karanjikar

Kerry Kennedy Spilker

Michael G DaGue

Gayani Pinnawala Arachchilage

Jerry Max Rovner

Peter Charles Ricci

Thomas M Vu

Nancy G Dunn

Dennis P Essl

Zoran Mirkovic

Stephen J Decanio

Jason C Hicks

Provided herein are novel surfactant compositions and methods having application in a variety of fields including enhanced oil recovery, the cleaning industry as well as groundwater remediation. The surfactant compositions are based on lignin bio-oil with a phenol hydroxyl group as the main functional group. The compositions include carboxylic surfactant s and mixed hydrophilic and hydrophobic surfactant structures, which can be used for the recovery of crude oil compositions from challenging reservoirs.

Surfactant compositions

The instant invention pertains to new processes which produce an energy source effectively, efficiently, and in a more environmentally friendly manner. The process comprises hydrolyzing a lignocellulosic feedstock to form lignocellulosic hydrolyzate and a hydrolyzate residue. The lignocellulosic hydrolyzate is treated to produce hydrogen. The hydrolyzate residue may be reacted with hydrogen in the presence of a catalyst to yield the energy source.

Integrated biofuel process

The present invention discloses processes for generating a hydrocarbon feedstock for biofuels synthesis from lignin via hydroprocessing. Embodiments of the present invention can occur in a refinery setting or in a paper mill setting. Embodiments of the present invention can utilize the separated lignin or the entire black liquor solution.

Process for generating a hydrocarbon feedstock lignin

Process for generating a hydrocarbon feedstock from lignin

A method of making surfactants from lignin is disclosed by reducing lignin in the presence of a metal oxide or iron based catalyst in an organic hydrogen donor solvent to produce lignin phenol and subjecting the lignin phenol to one or a combination of several reactions such as alkoxylation, alkylation, sulfonation, sulfation, alkoxysulfation, and sulfomethylation. The lignin surfactants so produced can be employed in a surfactant system to recover oil from underground formations.

Catalytic method for the preparation of lignin phenol surfactants in organic solvents

Catalytic method for the preparation of lignin phenol surfactants in

A method of producing oil soluble surfactants from lignin is disclosed, along with a method for recovering oil from underground formations by means of a surfactant flooding system containing these lignin surfactants. Lignin is reduced in the presence of a carbon monoxide or hydrogen reducing agent at high temperature and pressure, alkoxylated with an .alpha.-olefin epoxide and then changed into oil soluble lignin surfactants by a reaction selected from the group consisting of sulfonation, sulfation and alkoxysulfation.

Hydrocarbon recovery comprising injecting a slug comprising oil soluble

The invention is a method for forming a high viscosity gel by mixing about 0.9% to about 3.0% by weight of hydroxy propyl cellulose having an average molecular weight greater than about 1,000,000 about 0.4% to about 3.0% by weight of an alkali metal dodecyl sulfate in the ratio of about 3:1 to about 1:1.5 of cellulose to sulfate, and a brine having a salinity greater than about 20,000 ppm TDS.

Method for forming a high viscosity gel

The invention is an aqueous shear-thickening composition comprising in one embodiment about 0.2% to about 1% by weight of hydroxypropyl cellulose having an average molecular weight between about 1,000,000 and about 1,300,000, about 0.1% to about 0.7% by weight of an alkali metal dodecyl sulfate in a ratio of about 2.5:1 to about 1.5:1 hydroxypropyl cellulose to alkali metal dodecyl sulfate, and water containing less than about 2000 ppm TDS.

Shear-thickening solutions with hydroxypropyl cellulose

The invention is a method of producing oil soluble surfactants from lignin which comprises reacting an alkylphenol having an alkyl chain of about 5 to about 20 carbon atoms with formaldehyde at elevated temperature to produce an intermediate product and reacting the intermediate product at an elevated temperature with a lignin phenol sulfonate to produce an oil soluble lignin surfactant, said lignin phenol sulfonate produced by placing lignin in contact with water, converting the lignin into low molecular weight lignin phenol by reducing the lignin in the presence of a reducing agent of carbon monoxide or hydrogen which creates a reduction reaction mixture comprising oil soluble lignin phenol, said reduction occurring at a temperature greater than about 200.degree. C. and a pressure greater than about 100 psi, recovering the oil soluble lignin phenol from the reduction mixture and sulfonating the lignin phenol to produce lignin phenol sulfonate.

Enhance oil recovery using oil soluble sulfonate surfactants from lignin

The invention is a method of producing oil soluble surfactants from lignin which comprises reacting benzyl alcohol with lignin phenol at elevated temperature in the presence of a non-nucleophilic basic catalyst to produce a lignin phenol reaction product, and sulfonating the lignin phenol reaction product to produce an oil soluble lignin surfactant, said lignin phenol produced by placing lignin in contact with water, converting the lignin into low molecular weight lignin phenol by reducing the lignin in the presence of a reducing agent of carbon monoxide or hydrogen which creates a reduction reaction mixture comprising oil soluble lignin phenol, said reduction occurring at a temperature greater than about 200.degree. C. and a pressure greater than about 100 psi, and recovering the oil soluble lignin phenol from the reduction mixture.

Enhanced oil recovery using oil soluble sulfonates from lignin and

The invention is a method for decreasing formation permeability in an underground formation around a wellbore by injecting an aqueous fresh water solution comprising about 0.9% to about 3.0% by weight of hydroxy propyl cellulose having an average molecular weight greater than about 1,000,000 and about 0.4% to about 3.0% by weight of an alkali metal dodecyl sulfate in the ratio of about 3:1 to about 1:1.5 of cellulose to sulfate, said formation must contain a connate brine having a salinity greater than about 20,000 ppm TDS, or an injected brine having a salinity greater than about 20,000 ppm TDS to mix and react with the aqueous solution to form a gel. The invention is also a method for forming a high viscosity gel by mixing hydroxy propyl cellulose, alkali metal dodecyl sulfate and sufficient salinity.

Gel method for decreasing permeability around a wellbore

The invention is a method of recovering hydrocarbons from an underground hydrocarbon formation penetrated by at least one injection well and at least one production well, which comprises injecting into an underground formation through an injection well about 0.05 to about 1.0 pore volumes of an aqueous surfactant slug comprising about 0.1% to about 10% by weight of a surfactant system, injecting a drive fluid into the formation through the injection well to push the surfactant slug towards the production well, and recovering hydrocarbons at the production well, said surfactant system comprised of a lignin phenol surfactant, a lignin, a primary amine having about 8 to about 20 carbon atoms, and a solubilizer.

Lignin phenol/lignin/amine surfactant system

The invention is a foam method for improving conformance during a steam flood or carbon dioxide flood in an underground hydrocarbon formation penetrated by at least one injection well and at least one production well, which comprises injecting into an injection well about 0.05% to about 2% by weight aqueous surfactant solution, and then injecting into the injection well a flooding medium of steam or carbon dioxide, said surfactant solution comprising a surfactant having the formula

Foaming agents for carbon dioxide and steam floods

A method of producing surfactants from lignin is disclosed by reducing lignin in the presence of a carbon monoxide or hydrogen reducing agent at high temperature and pressure to produce low molecular weight lignin phenols and subjecting the lignin phenols to one or a combination of several reactions such as alkoxylation, alkylation, sulfonation, sulfation, alkoxysulfation, and sulfomethylation. The lignin surfactants so produced can be employed in a surfactant system to recover oil from underground formations.

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Houston, TX, United States of America

Douglas G Naae