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NZ796668B2 - Branched amino acid surfactants for oil and gas production - Google Patents
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NZ796668B2 - Branched amino acid surfactants for oil and gas production - Google Patents

Branched amino acid surfactants for oil and gas production

Info

Publication number
NZ796668B2
NZ796668B2 NZ796668A NZ79666821A NZ796668B2 NZ 796668 B2 NZ796668 B2 NZ 796668B2 NZ 796668 A NZ796668 A NZ 796668A NZ 79666821 A NZ79666821 A NZ 79666821A NZ 796668 B2 NZ796668 B2 NZ 796668B2
Authority
NZ
New Zealand
Prior art keywords
following formula
butyloctyl
oxy
chloride
alkyl
Prior art date
Application number
NZ796668A
Other versions
NZ796668A (en
Inventor
Edward Asirvatham
Original Assignee
Advansix Resins & Chemicals Llc
Filing date
Publication date
Application filed by Advansix Resins & Chemicals Llc filed Critical Advansix Resins & Chemicals Llc
Priority claimed from PCT/US2021/041337 external-priority patent/WO2022015673A1/en
Publication of NZ796668A publication Critical patent/NZ796668A/en
Publication of NZ796668B2 publication Critical patent/NZ796668B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/594—Compositions used in combination with injected gas, e.g. CO2 orcarbonated gas
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/62—Compositions for forming crevices or fractures
    • C09K8/66—Compositions based on water or polar solvents
    • C09K8/68—Compositions based on water or polar solvents containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/62—Compositions for forming crevices or fractures
    • C09K8/70—Compositions for forming crevices or fractures characterised by their form or by the form of their components, e.g. foams
    • C09K8/703—Foams
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/92—Compositions for stimulating production by acting on the underground formation characterised by their form or by the form of their components, e.g. encapsulated material
    • C09K8/94—Foams
    • E—FIXED CONSTRUCTIONS
    • E21—EARTH OR ROCK DRILLING; MINING
    • E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
    • E21B43/00—Methods or apparatus for obtaining oil, gas, water, soluble or meltable materials or a slurry of minerals from wells
    • E21B43/16—Enhanced recovery methods for obtaining hydrocarbons

Abstract

Surfactants of Formula (I) where R1 and R2 are hydrogen, oxygen, C1-6 alkyl optionally substituted with carboxylate, hydroxyl, sulfonyl, or sulfonates, n is 2-5, R3 is C5-C12 alkyl, R4 is C3-10 alkyl, wherein the terminal nitrogen is optionally substituted with R5, wherein R5 is as per R1, and an optional counterion of Cl, Br, I, or 4-methylbenzenesulfonate. The surfactants may be used in oil and gas production for hydrocarbon recovery, such as in foamed and non-foamed formulations and when mixed with a bio oil, or gas. They may also be used in demulsification of other oils such as corn oil.

Claims (20)

1. Use for the recovery of hydrocarbons of a formulation comprising: at least one surfactant of the following formula: wherein R and R are independently chosen from hydrogen, an oxygen atom, and C -C alkyl that is optionally substituted with a group selected from carboxylate, hydroxyl, sulfonyl and sulfonate; n is an integer from 2 to 5; R is C5-C12 alkyl; R is C -C alkyl; the terminal nitrogen is optionally further substituted with R , wherein R is chosen from hydrogen, an oxygen atom, and C1-C6 alkyl that is optionally substituted with a group selected from carboxylate, hydroxyl, sulfonyl and sulfonate; an optional counterion associated with the surfactant and, if present, the counterion is selected from chloride, bromide, iodide, and 4- methylbenzenesulfonate; and an aqueous phase.
2. The use of claim 1, wherein the formulation further comprises at least one additional surfactant selected from: an anionic surfactant having a hydrophobic chain of 12 to 24 carbon atoms selected from sulfonate surfactants, sulfate surfactants, cationic surfactants, nonionic surfactants, and zwitterionic surfactants.
3. The use of claim 1 or claim 2, wherein the aqueous phase comprises at least one inorganic salt, selected from: sodium chloride, sodium sulfate, potassium chloride, magnesium sulfate and magnesium chloride.
4. The use of any one of claims 1 to 3, wherein the formulation further comprises at least one polymer selected from: a quaternary ammonium compound and/or an anionic surfactant.
5. The use of claim 4, wherein the quaternary ammonium compound is a cationic polymer comprising a quaternary diallyl dialkyl ammonium monomer.
6. The use of claim 4, wherein the anionic surfactant is an anionic polymer comprising an anionic monomer selected from acrylic acid, methacrylic acid, and combinations thereof, wherein the anionic polymer has an average molecular weight ranging from about 50,000 to about 10,000,000.
7. The use of any one of claims 1 to 6, wherein the formulation further comprises lecithin or modified lecithin.
8. The use of any one of claims 1 to 7, wherein the formulation further comprises at least one water immiscible solvent.
9. The use of any one of claims 1 to 8, wherein the formulation further comprises at least one water miscible solvent.
10. The use of any one of claims 1 to 9, wherein the formulation further comprises at least one gas selected from: air, nitrogen, carbon dioxide, and natural
11. The use of any one of claims 1 to 10, wherein the formulation further comprises at least one additive selected from: hydrogen chloride, an ammonium salt, ammonium bicarbonate, ammonium carbonate, or ammonium hydroxide, alcohol, crosslinking agent, breaker delay agents, particles, proppants, gas component, breaker aids, oxygen scavengers, alcohols, scale inhibitors, corrosion inhibitors, fluid-loss additives, biocides/bactericides, friction reducers, and latex.
12. The use of any one of claims 1 to 11, wherein the surfactant comprises at least one of: 6-((2-butyloctyl)oxy)-N,N,N-trimethyloxohexanaminium iodide, having the following formula: 6-((2-butyloctyl)oxy)-N,N-dimethyloxohexanaminium 4- methylbenzenesulfonate, having the following formula: 6-((2-butyloctyl)oxy)-N,N-dimethyloxohexanaminium chloride, having the following formula: 4-((6-((2-butyloctyl)oxy)oxohexyl)dimethylammonio)butane sulfonate, having the following formula: H C CH O S O 2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula: 6-((2-butyloctyl)oxy)oxohexanaminium chloride, having the following formula: ; and 6-((2-butyloctyl)oxy)oxohexanaminium 4- methylbenzenesulfonate, having the following formula:
13. A method of recovering a hydrocarbon, comprising the steps of: providing at least one of the formulations defined in any one of claims 1 to 12; injecting the at least one formulation into a well; and recovering material from the well after the step of injecting the formulation into the well.
14. A method of recovering a hydrocarbon, comprising the steps of: providing at least one of the formulations defined in any one of claims 1 to 12; mixing the at least one formulation with a material that includes a bio oil; and recovering the bio oil from the mixture.
15. The method of claim 14, wherein the material that includes the bio oil is stillage.
16. A method of recovering a hydrocarbon comprising the steps of: introducing a foamed fluid composition within an oil or gas well and performing an operation with the foamed fluid composition wherein the foamed composition comprises: a base fluid comprising: an oil-based or a water-based fluid; a gas, at least one surfactant of the following formula: wherein R and R are independently chosen from hydrogen, an oxygen atom, and C -C alkyl that is optionally substituted with a group selected from carboxylate, hydroxyl, sulfonyl, and sulfonate; n is an integer from 2 to 5; R is C -C alkyl; R is C -C alkyl; the terminal nitrogen is optionally further substituted with R , wherein R is chosen from hydrogen, an oxygen atom, and C1-C6 alkyl that is optionally substituted with a group selected from carboxylate, hydroxyl, sulfonyl and sulfonate; an optional counterion is associated with the surfactant and, if present, the counterion is selected from chloride, bromide, iodide, and 4- methylbenzenesulfonate.
17. The method of claim 16, wherein the operation is selected from: a gas lift operation, a drilling operation, a completion operation, a stimulation operation, a fracturing operation, an injection operation, an enhanced oil recovery operation, and combinations thereof.
18. The method of claim 16 or 17, wherein the surfactant comprises at least one of: 6-((2-butyloctyl)oxy)-N,N,N-trimethyloxohexanaminium iodide, having the following formula: 6-((2-butyloctyl)oxy)-N,N-dimethyloxohexanaminium 4- methylbenzenesulfonate, having the following formula: 6-((2-butyloctyl)oxy)-N,N-dimethyloxohexanaminium chloride, having the following formula: 44-((6-((2-butyloctyl)oxy)oxohexyl)dimethylammonio)butane sulfonate, having the following formula: H C CH O S O 2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula: 6-((2-butyloctyl)oxy)oxohexanaminium chloride, having the following formula: ; and 6-((2-butyloctyl)oxy)oxohexanaminium 4- methylbenzenesulfonate, having the following formula:
19. The use of any one of claims 1 to 12, wherein n=5.
20. The method of any one of claims 13 to 18, wherein n=5.
NZ796668A 2021-07-12 Branched amino acid surfactants for oil and gas production NZ796668B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202063051192P 2020-07-13 2020-07-13
PCT/US2021/041337 WO2022015673A1 (en) 2020-07-13 2021-07-12 Branched amino acid surfactants for oil and gas production

Publications (2)

Publication Number Publication Date
NZ796668A NZ796668A (en) 2025-06-27
NZ796668B2 true NZ796668B2 (en) 2025-09-30

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