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

A method of recovering hydrocarbons from an underground hydrocarbon formation penetrated by at least one injection well and at least one production well, the method comprising:

• injecting into the formation through an injection well a surfactant slug comprising about 0.1% to about 10% by weight of surfactants, said surfactants produced by placing lignin in contact with a hydrogen donor organic solvent, wherein the hydrogen donor solvent is selected from the group consisting of tetralin, lignin phenol or biomass;
• converting the lignin into low molecular weight-lignin phenol by
• reducing the lignin in the presence of a reducing agent and a catalyst at a temperature of at least about 200° C. and a pressure of at least 100 psig and
• recovering the lignin phenols from the reduction mixture, and
• converting the lignin phenol into lignin surfactants,
• wherein said catalyst contains from about 1.0% to about 15% by weight molybdenum oxide and a second component selected from the group consisting of nickel oxide or cobalt oxide, wherein the weight ratio of molybdenum oxide to said second component ranges from about 3:1 to about 5:1, and wherein the molybdenum oxide and second component are supported on a support selected from the group consisting of neutral alumina, basic alumina and acidic alumina;
• injecting into the formation through the injection well a drive fluid to push the surfactant slug towards a production well;
• and
• recovering hydrocarbons at the production well.

A method of recovering hydrocarbons from an underground hydrocarbon formation penetrated by at least one injection well and at least one production well, the method comprising:

• injecting into the formation through an injection well a surfactant slug comprising about 0.1% to about 10% by weight of surfactants produced from lignin, said surfactants produced by placing lignin in contact with a hydrogen donor organic solvent;
• converting the lignin into low molecular weight-lignin phenol by
• reducing the lignin in the presence of a reducing agent and a catalyst at a temperature of at least about 200° C. and a pressure of at least about 100 psig yielding a reaction mixture containing the lignin phenol;
• recovering the lignin phenol from the reaction mixture;
• and
• converting the lignin phenol into lignin surfactants,
• recovering the lignin phenols from the reduction mixture, and
• converting the lignin phenol into lignin surfactants,
• wherein the hydrogen donor organic solvent is tetralin, lignin phenol or biomass oil, and
• wherein the catalyst contains from about 1% to about 15% by weight molybdenum oxide and a second component selected from the group consisting of nickel oxide or cobalt oxide on a support selected from the group consisting of neutral alumina, basic alumina, and acidic alumina;
• injecting into the formation through the injection well a drive fluid to push the surfactant slug towards a production well;
• and
• recovering hydrocarbons at the production well.

A method of recovering hydrocarbons from an underground hydrocarbon formation penetrated by at least one injection well and at least one production well, the method comprising;

• injecting into the formation through an injection well a surfactant slug comprising about 0.1% to about 10% by weight of surfactants, said surfactants produced by
• placing lignin in contact with a hydrogen donor organic solvent,
• converting the lignin into low molecular weight-lignin phenol by reducing the lignin in the presence of a reducing agent and a catalyst at a temperature of at least about 200° C. and a pressure of at least 100 psig yielding a reaction mixture containing the lignin phenol,
• recovering the lignin phenol from the reaction mixture, and converting the lignin phenol into lignin surfactants,
• wherein the catalyst is an iron based catalyst comprising a) an iron sulfide and b) at least one other sulfide of a metal selected from the group consisting of copper, silver, tin, chromium, cobalt, nickel, zinc and molybdenum,
• recovering the lignin phenols from the reduction mixture, and
• converting the lignin phenol into lignin surfactants;
• injecting into the formation through the injection well a drive fluid to push the surfactant slug towards a production well;
• and
• recovering hydrocarbons at the production well.