WO2011106287A1 - Compositions de tensio-actifs anioniques tolérantes aux sels, pour des applications en récupération assistée ou améliorée du pétrole (eor ou ior) - Google Patents

Compositions de tensio-actifs anioniques tolérantes aux sels, pour des applications en récupération assistée ou améliorée du pétrole (eor ou ior) Download PDF

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WO2011106287A1
WO2011106287A1 PCT/US2011/025618 US2011025618W WO2011106287A1 WO 2011106287 A1 WO2011106287 A1 WO 2011106287A1 US 2011025618 W US2011025618 W US 2011025618W WO 2011106287 A1 WO2011106287 A1 WO 2011106287A1
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ppm
reservoir
composition
anionic surfactant
groups
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PCT/US2011/025618
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Mukul M. Sharma
Bo Gao
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Board Of Regents, The University Of Texas System
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    • 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

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  • the present invention relates in general to the field of oil recovery, and more particularly, to a novel family of anionic surfactants for Enhanced Oil Recovery (EOR) or Improved Oil Recovery (IOR) applications having a higher salt-tolerance, a higher surface activity, and greater viscosity than conventional anionic surfactants used in EOR.
  • EOR Enhanced Oil Recovery
  • IOR Improved Oil Recovery
  • R 3 O R 5 wherein R, Ri, R 2 , and R3 are selected from the group consisting of straight or branched chain Ci to C 22 alkyl, aryl or hydrogen, and each R moiety can be the same or different; R4 and R 5 are selected from the group comprising a straight or branched chain Ci to C6 alkyl with the further proviso that when either is a C(, it may exist as a cyclohexyl ring; R 6 and R 7 are selected from the group consisting of straight or branched chain C 2 to C6 alkyl or aryl with the further proviso that R 6 and R 7 may be the same or different and wherein X is selected from the group comprising -S-, -S-S-, ⁇ Di -Rg— D- or— R 8 — Di — Rg — wherein Rg is a straight or branched chain Ci to C 10 alkyl or aryl and Di is selected from the group consisting of—0-,— S—
  • United States Patent Application No. 20080261835 (Berger et al., 2008) describes a process for recovering heavy oil with the steps of: a) injecting into one or more injection wells an aqueous injection fluid containing one or more surfactants designed to form a pseudo-emulsion between the injection fluid and the heavy oil, and, b) recovering the oil from one or more producing wells.
  • the process does not require the addition of outside mechanical or thermal energy or solvents to recover the heavy oil and does not form emulsions between the injection fluid and the heavy oil that may be difficult to break when brought to the surface or may cause increased viscosity and injectivity problems within the reservoir.
  • the present invention relates to a new family of anionic surfactants for use in enhanced or improved recovery of crude oil from oil reservoirs.
  • the anionic surfactants described herein can be applied in chemical EOR operations in petroleum reservoirs with very high salinity and/or hardness.
  • the molecules of the present invention are very surface active and have been shown to yield ultra-low interfacial tensions at very low concentrations (10 to 100 times lower concentrations compared to traditional EOR surfactants). In addition they exhibit high viscosity under certain conditions and, therefore, they can be used without any polymer (with the surfactant providing the necessary viscosity). This is in particularly advantageous because polymers become less effective i.e. have a lower viscosity as the salinity increases.
  • compositions for enhanced or improved oil recovery are disclosed in one embodiment of the instant invention.
  • the anionic surfactant composition for treating a hydrocarbon- bearing formation or a reservoir, wherein the surfactant is sufficiently soluble in water, hard water, hard brine or in solutions of high salinity to be injected into a hydrocarbon-bearing formation comprises a molecule described by formula (I)
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof.
  • the composition is used alone, in conjunction with a polymer or as part of an alkaline surfactant polymer (ASP) composition for treating the hydrocarbon-bearing formation.
  • ASP alkaline surfactant polymer
  • the composition of the present invention can be used for environmental ground water cleanup and other surfactant based applications.
  • the composition is used to treat the reservoir with reservoir brine salinities of up to about 350,000 ppm, including salinities of 200 ppm, 500 ppm, 1000 ppm, 5000 ppm, 10,000 ppm, 50,000 ppm, 100,000 ppm, 150,000 ppm, 200,000 ppm, 250,000 ppm, 300,000 ppm, and 350,000 ppm.
  • the composition is used to treat the reservoir with a hardness ion concentration of up to about 250,000 ppm.
  • the composition is used to treat the reservoir with a hardness ion concentration of 200 ppm, 500 ppm, 1000 ppm, 5000 ppm, 10,000 ppm, 50,000 ppm, 100,000 ppm, 150,000 ppm, 200,000 ppm, and 250,000 ppm.
  • the composition of the present invention is thermally stable at temperatures of up to about 300°C.
  • the composition is thermally stable at temperatures of 25°C, 50°C, 75°C, 100°C, 150°C, 200°C, 250°C, and 300°C.
  • the anionic surfactant composition comprises at least one of (n-Ci 6 H 32 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 (n-C 14 H 2 8) 2 (OCH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 or (n-C 14 H 2 8) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 .
  • the present invention provides a method of making an anionic surfactant of formula (I) for treating a hydrocarbon-bearing formation or a reservoir
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0-15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof, wherein the surfactant is sufficiently soluble in water, hard water, hard brine or in solutions of high salinity to be injected into a hydrocarbon-bearing formation comprising the steps of: reacting an 1 ,2-alkylepoxide [R-(CHCH 2 0)] and a diol [OH-R'-OH] in a reaction chamber
  • the present invention discloses a specific method of making an anionic surfactant composition having a formula chain length of 12 or more carbon atoms comprising the steps of: reacting 1,2-epoxytetradecane and ethylene glycol in a reaction chamber in the presence of a basic catalyst to form an intermediate diol, wherein the basic catalyst comprises KOH dissolved in methanol, NaOH, NaH, KH, LiH, or any combinations thereof and reacting the intermediate diol with ethylene sulfate in the presence of a base comprising KOH in methanol, NaOH, NaH, KH, LiH to give the anionic surfactant composition having the formula chain length of 12 or more carbon atoms.
  • the anionic surfactant comprises at least one of (n-C 16 H 32 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 (n-C 14 H 28 ) 2 (OCH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 or (n-C 14 H 28 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 .
  • the anionic surfactant composition is used to treat a hydrocarbon bearing formation for enhanced or improved oil recovery, environmental ground water cleanup, and other surfactant based applications.
  • the anionic surfactant is sufficiently soluble in water, hard water, and hard brine or in solutions of high salinity to be injected into a hydrocarbon-bearing formation or a reservoir.
  • the anionic surfactant composition is used alone, in conjunction with a polymer or as part of an alkaline surfactant polymer (ASP) composition for treating the hydrocarbon-bearing formation or reservoir.
  • ASP alkaline surfactant polymer
  • the instant invention in one embodiment describes a method of enhanced or improved oil recovery from a hydrocarbon bearing formation or a reservoir comprising the steps of: injecting an anionic surfactant composition of formula (I) having a general formula
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof, wherein the anionic surfactant composition is in water, hard water, in solutions of high salinity or hard brine and recovering the oil following the injection of the anionic surfactant composition.
  • the anionic surfactant composition comprises at lease one of (n-Ci 6 H32) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 (n-C 14 H 28 ) 2 (OCH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 or (n-C 14 H 28 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2.
  • the reservoir brine salinities are up to about 350,000 ppm.
  • the reservoir can have brine salinities of 200 ppm, 500 ppm, 1000 ppm, 5000 ppm, 10,000 ppm, 50,000 ppm, 100,000 ppm, 150,000 ppm, 200,000 ppm, 250,000 ppm, 300,000 ppm, and 350,000 ppm.
  • the reservoir has a hardness ion concentration of up to about 250,000 ppm including reservoirs hardness ion concentration of 200 ppm, 500 ppm, 1000 ppm, 5000 ppm, 10,000 ppm, 50,000 ppm, 100,000 ppm, 150,000 ppm, 200,000 ppm, and 250,000 ppm.
  • the anionic surfactant composition as described in the method of the present invention is thermally stable at reservoir temperatures of up to about 300°C, that includes temperatures of 25°C, 50°C, 75°C, 100°C, 150°C, 200°C, 250°C, and 300°C.
  • Another embodiment of the present invention discloses a method of enhanced or improved oil recovery from a hydrocarbon bearing formation or a reservoir comprising the steps of: injecting an anionic surfactant composition of formula (I) having a general formula
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof, alone, in conjunction with a polymer or as an alkaline-surfactant-polymer formulation (ASP) into the hydrocarbon bearing formation at temperatures of up to about 300° C, wherein the anionic surfactant composition is in water, hard water, in solutions of high salinity or hard brine and injecting a polymer "push" solution to recover the oil.
  • the reservoir brine salinities are up to about 350,000 ppm and a hardness ion concentration of up to about 250,000 ppm.
  • the anionic surfactant composition comprises at least one of (n-Ci 6 H32) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 (n-C 14 H 28 ) 2 (OCH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 or (n-C 14 H 28 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 .
  • Yet another embodiment of the present invention provides for a method of enhanced or improved oil recovery from a hydrocarbon bearing formation or a reservoir comprising the steps of: injecting an anionic surfactant composition having a formula (n-Ci 6 H 32 ) 2 (OCH 2 CH 2 CH 2 CH 2 0)(OC 2 H S0 4 Na) 2 into the hydrocarbon bearing formation or reservoir, wherein the anionic surfactant composition is in water, hard water, in solutions of high salinity or hard brine and recovering the oil following the injection of the anionic surfactant composition.
  • the reservoir brine salinities are up to about 350,000 ppm and hardness ion concentration are up to about 250,000 ppm.
  • the anionic surfactant composition is thermally stable at reservoir temperatures of up to about 300°C.
  • compositions for treating a hydrocarbon bearing formation or a reservoir comprising: an anionic surfactant composition of formula (I)
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof and one or more additional surfactants selected from the group consisting of an anionic, a cationic or a non-ionic surfactant, a branched alkyl benzene sulfonate, a linear alkyl benzene sulfonate, an alkyl toluene sulfonate, and an al
  • composition as disclosed hereinabove composition is used to treat the reservoir with reservoir brine salinities of up to about 350,000 ppm and a hardness ion concentration of up to about 250,000 ppm.
  • the composition of the present invention is thermally stable at temperatures of up to about 300°C.
  • the composition is used for enhanced or improved oil recovery, environmental ground water cleanup, and other surfactant based applications
  • the present invention is a method of enhanced or improved oil recovery from a hydrocarbon bearing formation or a reservoir comprising the steps of: injecting a surfactant composition comprising an anionic surfactant composition of formula (I)
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof and one or more additional surfactants selected from the group consisting of an anionic, a cationic or a non-ionic surfactant, a branched alkyl benzene sulfonate, a linear alkyl benzene sulfonate, an alkyl toluene sulfonate, and an al
  • the reservoir brine salinities are up to about 350,000 ppm.
  • the reservoir has a hardness ion concentration of up to about 250,000 ppm.
  • the anionic surfactant composition is thermally stable at reservoir temperatures of up to about 300°C.
  • an anionic surfactant for optimal oil recovery from a hydrocarbon bearing formation or a reservoir comprising the steps of: (i) identifying a temperature, a salinity and a hardness ion concentration of the hydrocarbon bearing formation or the reservoir, (ii) providing an anionic surfactant composition having a formula (I)
  • Ri and R 2 are identical or different and are selected from the group consisting of straight or branched chain d to C30 or more alkyl, aryl, hydrogen, ethylene oxide or propylene oxide groups
  • Xi and X 2 are identical or different and are selected from the group consisting of phosphate, sulfate, carboxylate, sulphonate, other suitable anionic groups, ethylene oxide or propylene oxide groups
  • S is a spacer group comprising 0 -15 saturated or unsaturated carbons selected from one or more alkyl groups, aryl groups, stilbene, polyethers, an ether linkage or combinations thereof and modifications and substitutions thereof, and (iii) selecting an appropriate Ri, R 2 , and S that would impart a suitable hydrophilic-lipophilic balance (HLB) to the anionic surfactant for optimal oil recovery from the hydrocarbon bearing formation or a reservoir.
  • HLB hydrophilic-lipophilic balance
  • the selected anionic surfactant effectively recovers oil in reservoir brine salinities of up to about 350,000 ppm. In another aspect the selected anionic surfactant effectively recovers oil in reservoir hardness ion concentrations of up to about 250,000 ppm. In yet another aspect the selected anionic surfactant effectively recovers oil in reservoir temperatures of up to about 300°C.
  • FIG. 1 is a schematic illustration of an offshore oil platform with facilities for injecting chemical solutions into the reservoir for the purpose of flooding the reservoir to enhance the oil recovery according to some embodiments of the present invention
  • FIG. 2 is a schematic showing the anionic Gemini surfactants from diglycidyl ethers 20 ;
  • FIG. 3 shows the base synthesis route of the present invention 25 ;
  • FIG. 4A is a schematic of reaction I to get the intermediate diol compound
  • FIG. 4B is a schematic of reaction II to get the C14-C 2 -C14 molecule as described in the present invention.
  • FIG. 5 is a plot of the dynamic IFT measurement for 0.01 wt % C14-C 2 -C14 molecule in brine solution (10% NaCl + 6% CaCl 2 ) with decane;
  • FIG. 6 is a plot of the dynamic IFT measurement for 0.01 wt % C14-C4-C14 molecule in brine solution (10% NaCl + 6% CaCl 2 ) with decane;
  • FIG. 7 is a plot of the dynamic IFT measurement showing the alkane carbon number (ACN) effect for 0.02% solutions of C 14 -C 2 -C 14 and C 14 -C 4 -C 14 surfactant in brine (20% NaCl) at 55°C for 40 mins;
  • FIG. 8 is a plot of the dynamic IFT measurement showing the effect of molecular structure for 0.02% solutions of surfactant in brine (15% NaCl) at 55°C with dodecane;
  • FIG. 9 is a plot of the dynamic IFT measurement showing the salinity effect for 0.02% surfactant in brine solution (15% NaCl) at 55°C with dodecane
  • FIG. 10 is a plot of the dynamic IFT measurement showing the hardness (Ca ++ ) effect for 0.02% C14- C4-C14 in brine solution (15% NaCl) at 55°C with dodecane;
  • FIG. 1 1 is a plot of IFT measurement showing the synergistic effect between two Gemini surfactants (C 14 -C4-C 14 and C16-C4-C16) at 0.02% and Petrostep A-l (Ci 5 _ig BABS) at different concentrations in brine solution (15% NaCl) at 55°C with dodecane;
  • FIG. 12 is a plot of surfactant solution viscosity showing the concentration dependence of the apparent viscosity of aqueous solutions of Ci 6 -C 4 -Ci 6 at 50°C and shear rate of 10 s 4 ;
  • FIG. 13 is a plot of the surfactant solution viscosity showing the shear rate dependence of the viscosity of aqueous solutions of Ci 6 -C 4 -Ci 6 at different concentrations at 50°C.
  • the present invention describes a novel anionic surfactant composition for Enhanced or Improved Oil Recovery (EOR or IOR) applications.
  • the surfactants have very low interfacial tensions at very low concentrations and exhibit very high viscosities enabling their use without any polymers. This is particularly attractive because polymers become less effective (i.e. have lowered viscosities) as the salinity increases.
  • the surfactants of the instant invention can be used particularly in petroleum reservoirs with very high salinity and/or hardness.
  • the molecular structure of the novel family of surfactants of the present invention is fundamentally different from ones that are traditionally used in EOR applications.
  • the unique and versatile structure of these surfactants has endowed them with some interesting properties.
  • Their primary advantages of the surfactants over currently used EOR surfactants are: (i) they are much more salt-tolerant. They can be used in reservoirs with reservoir brine salinities of up to 350,000 ppm and hardness ion concentrations up to 250,000 ppm, (ii) they are very surface active.
  • Ultra-low interfacial tensions can be obtained with surfactant concentrations 10 to 100 times lower than traditional EOR surfactants, (iii) under certain conditions they form viscous solutions so that they can potentially be used without polymers, and (iv) they can be used in conjunction with traditional EOR surfactants at significantly lower concentrations than are currently needed.
  • the present invention also addresses the problem of oil recoveries associated in reservoirs with brines salinities in excess of 100,000 ppm, which are generally considered to be difficult targets for EOR.
  • the novel class of surfactant molecules of the present invention works well in such hostile environments and may make it possible to tackle this problem at a modest cost.
  • This present invention enables the concentration of the surfactant used in chemical EOR to be decreased by an order of magnitude. It also enables chemical EOR to be applied to difficult reservoirs with saline, hard formation brines, which are often very troublesome to design and work with for more conventional formulations.
  • the present invention can also be a viscosifier for special rheology control in either EOR or fracturing fluid applications and a co-surfactant/co-solvent in traditional chemical EOR surfactant formulations.
  • the term "treating” includes placing a chemical (e.g., a fluorochemical, cationic polymer, or corrosion inhibitor) within a hydrocarbon-bearing formation using any suitable manner known in the art (e.g., pumping, injecting, pouring, releasing, displacing, spotting, or circulating the chemical into a well, well bore, or hydrocarbon-bearing formation).
  • a chemical e.g., a fluorochemical, cationic polymer, or corrosion inhibitor
  • polymer refers to a molecule having a structure that essentially includes the multiple repetitions of units derived, actually or conceptually, from molecules of low relative molecular mass.
  • polymer includes "oligomer”.
  • bonded refers to having at least one of covalent bonding, hydrogen bonding, ionic bonding, Van Der Waals interactions, pi interactions, London forces, or electrostatic interactions.
  • productivity as applied to a well refers to the capacity of a well to produce hydrocarbons; that is, the ratio of the hydrocarbon flow rate to the pressure drop, where the pressure drop is the difference between the average reservoir pressure and the flowing bottom hole well pressure (i.e., flow per unit of driving force). The idea is to flood the entire reservoir with chemical solutions to mobilize and displace the oil to the production wells.
  • Alkyl group and the prefix “alk-” are inclusive of both straight chain and branched chain groups and of cyclic groups having up to 30 carbons (in some embodiments, up to 20, 15, 12, 10, 8, 7, 6, or 5 carbons) unless otherwise specified. Cyclic groups can be monocyclic or polycyclic and, in some embodiments, have from 3 to 10 ring carbon atoms.
  • Alkylene is the divalent form of the “alkyl” groups defined above.
  • Arylalkylene refers to an "alkylene” moiety to which an aryl group is attached.
  • aryl as used herein includes carbocyclic aromatic rings or ring systems, for example, having 1, 2, or 3 rings and optionally containing at least one heteroatom (e.g., O, S, or N) in the ring.
  • heteroatom e.g., O, S, or N
  • aryl groups include phenyl, naphthyl, biphenyl, fluorenyl as well as furyl, thienyl, pyridyl, quinolinyl, isoquinolinyl, indolyl, isoindolyl, triazolyl, pyrrolyl, tetrazolyl, imidazolyl, pyrazolyl, oxazolyl, and thiazolyl.
  • an exemplary offshore oil platform is schematically illustrated and generally designated 10.
  • Semi-submersible platform 12 is centered over submerged hydrocarbon-bearing formation 14 located below sea floor 16.
  • Subsea conduit 18 extends from deck 20 of platform 12 to wellhead installation 22 including blowout preventers 24.
  • Platform 12 is shown with hoisting apparatus 26 and derrick 28 for raising and lowering pipe strings such as work string 30.
  • Wellbore 32 extends through the various earth strata including hydrocarbon-bearing formation 14. Casing 34 is cemented within wellbore 32 by cement 36. Work string 30 may include various tools including, for example, sand control screen assembly 38 which is positioned within wellbore 32 adjacent to hydrocarbon-bearing formation 14. Also extending from platform 12 through wellbore 32 is fluid delivery tube 40 having fluid or gas discharge section 42 positioned adjacent to hydrocarbon- bearing formation 14, shown with production zone 48 between packers 44, 46.
  • the surfactants used in these EOR processes are mixtures of petroleum sulfonates or sulfates derived from crude oil, blended with caustic and other co-surfactants. These mixtures are often comprised of a surfactant homologous series. For these systems, surfactant concentrations of between 0.5 and 5% need to be used to achieve good phase behavior and ultra-low interfacial tension.
  • the present inventors have conducted extensive and productive studies [1 8] on testing a new generation of chemical systems (polymers, improved surfactant/co-surfactant/co-solvent molecules, different alkalis and new additives), and designing systematic laboratory protocols for testing these systems.
  • Gemini surfactants are made of two amphiphilic moieties (either identical or different) connected to the head groups by a spacer group (FIG. 3).
  • the spacer group comprises 0 - 15 saturated or unsaturated carbons selected from one or more straight chain alkyl groups, branched chain alkyl groups, aliphatic groups, aromatic groups, heterocyclic groups, conjugated and non- conjugated aromatic groups, aryl groups, aryl groups with single or multiple ring substituents (for e.g.
  • the hydrocarbon tails can vary in length
  • the polar group can be anionic, cationic, nonionic or zwitterionic
  • the spacer group can be polar and non-polar. It is this unique and versatile structure of Gemini surfactants that has recently attracted considerable interest from the academic and industrial communities. These molecules have been shown to be endowed with some interesting properties, which form the basis of the present invention.
  • Geminis display ultralow critical micelle concentrations (CMC) and high surface activity (e.g. in reducing air-water tension) compared to conventional surfactants.
  • CMC critical micelle concentrations
  • high surface activity e.g. in reducing air-water tension
  • the present invention explores the application of Gemini surfactants in different oil and gas related operations, especially in chemical EOR operations. More specifically the present invention describes: (i) a low-cost and high-yield synthesis routes for synthesizing Gemini surfactants, based on considerations of raw material cost, final product yield and process complexity, (ii) testing the EOR potential of Gemini surfactants using a systematic laboratory approach, including phase behavior tests, aqueous stability tests, IFT measurements and coreflooding, (iii) understanding the complex rheological behavior of Gemini aqueous solutions and to examine the feasibility of applications in mobility control and VES (viscoelastic surfactant) fracturing fluids, and (iv) studying the synergy between Gemini and conventional surfactants.
  • VES viscoelastic surfactant
  • anionic Gemini surfactants are suitable for EOR applications. Typically, these molecules tend to be too water soluble to be effective (increased water solubility leads to greater partitioning into the aqueous phase, lowering the ability of the surfactants to act at the oil/water interface). Gemini surfactants that have the proper hydrophilic-lipophilic balance (HLB) are suitable. This balance depends on the salinity and temperature in the hydrocarbon formation or the reservoir. The present invention clearly shows how a structure of an anionic Gemini surfactant can be tailored to achieve the appropriate HLB under a given set of conditions.
  • HLB hydrophilic-lipophilic balance
  • Rist and Carlsen [25] reported a two-step and more general reaction scheme (FIG. 2) for selective synthesis of Gemini surfactants. Generally, this route offers higher yield ( ⁇ 45%) and requires less laboratory operations and reaction time. The synthesis route of Rist and Carlsen was chosen as the base route in the instant invention, with modifications made to increase the final yield and screen new chemicals for reducing costs and simplifying procedures.
  • Gemini surfactants are characterized by ultralow critical micelle concentrations (CMC) that are often one or two orders of magnitude lower than monomeric surfactants of equivalent chain length [12 5] .
  • CMC critical micelle concentrations
  • Rosen [11] ascribed these effects to a stronger distortion of the water structure by the two hydrophobic groups of a Gemini molecule. Migration of surfactants to the air/water interface is thereby promoted.
  • Menger [13] further connected this with closer interfacial packing of Geminis. The smaller cross-sectional area-per-molecule configuration promotes the formation of a more coherent interfacial film.
  • Zhu et al [46 ⁇ 7] investigated the synergism between a synthetic sulfonate Gemini surfactant and petroleum sulfonate. With low surfactant concentration, the mixture gave superior performance to conventional petroleum sulfonates in terms of CMC and IFT values. Tan et al. [48] synthesized several sulfonate Gemini surfactants and studied their interfacial properties. The IFT between crude oil and aqueous surfactant solution prepared in high mineralization brine could reach ultralow values, indicating the usage of Gemini surfactants in harsh water environment is promising. However, these studies were all based on a trial and error process without a full appreciation of Gemini structure- performance relationships. If these types of surfactants are to be used for EOR applications, more verification, such as phase behavior and coreflooding tests, need to be designed and carefully implemented.
  • anionic Gemini surfactants synthesized and described in the present invention offer several significant advantages over other surfactants used in EOR and overcomes some of the problems in the prior art pertaining to surfactants used in EOR. These include: (i) the anionic Gemini's of the present invention are very effective when used in low concentrations. For e.g. a 0.02% surfactant solution in water is suitable for EOR, this is at least 10- 100 fold lower than the concentrations needed for other surfactants used in EOR, (ii) the anionic Gemini's of the present invention can work at very high reservoir brine salinities, for e.g.
  • the anionic Gemini's of the present invention have a synergistic effect when combined with other surfactants.
  • the combination leads to further lowering of the interfacial tension and the concentrations of the surfactants required for EOR
  • the anionic Gemini surfactants of the present invention are extremely thermostable (stable at temperatures of up to about 300°C), this feature is extremely important as high temperatures are often encountered in EOR operations
  • the anionic Gemini's of the present invention exhibit high viscosity under certain conditions and, therefore, they can be used without any polymer (with the surfactant providing the necessary viscosity). This is in particularly advantageous not only from cost considerations but also, because the polymers become less effective i.e. have a lower viscosity as the salinity increases.
  • Sulfate Gemini surfactant (n- Ci 4 H 28 ) 2 (OCH 2 CH 2 0)(OC 2 H 4 S0 4 Na) 2 (denoted as C 14 -C 2 -C 14 ), was chosen to be the primary target molecule. This choice is made based on: 1) hydrophilic-lipophilic balance (HLB) considerations (a relatively long 14-carbon tail) and 2) the fact that shorter spacer group tends to give closer interfacial packing and interesting rheology.
  • HLB hydrophilic-lipophilic balance
  • Phase behavior tests and IFT measurements have been performed using the synthesized C14-C 2 -C14 sulfate Gemini. The key finding was the enormous ability of this molecule to tolerate high salinity and hardness while solubilizing considerable amounts of hydrocarbon even in the Type I region. Some technical implications will be discussed herein below.
  • Phase Behavior Test Table 3 below summarizes all the conditions that have been examined in the phase behavior tests so far.
  • Salt tolerance is very important for applications in harsh reservoir conditions. Unbiased performance for different synthetic brines and oil types shows Gemini's ability to adapt to different environments and certainly broaden its usage.
  • low IFT can only be obtained in the Type III microemulsion window, in which case oil can be solubilized into a microemulsion phase, but this does not guarantee the success of a flooding process if the mobility ratio is not carefully monitored and controlled.
  • the high solubilization ratio that has been observed at under-optimum (Type I) conditions is found to also coincide with ultra-low IFT measurements and is consistent with Huh's [49] theory.
  • IFT Measurement Although high solubilization ratio has been recorded during phase behavior tests, IFT measurements are the only way to provide reliable information about the interfacial tension. A spinning drop tensiometer was used to measure the dynamic IFT behavior of Gemini systems.
  • ultralow IFT was observed only under a very limited number of conditions. A reduction of 100 times or more in IFT was measured at 55°C for 0.01 wt% surfactant concentration. The solubilization ratio was calculated to be about 200. The applicability of Huh's equation to Gemini systems and to Type I phases and the way solubilization ratio is traditionally calculated needs to be examined carefully.
  • Phase behavior and IFT measurement results show that the C 14 -C 2 -C 14 molecule is too hydrophilic and not well HLB balanced. In order to get into a reasonable salinity window and further lower IFT values, the molecule should be made more lipophilic by either using longer carbon tail groups or more hydrophobic spacer groups.
  • FIG. 6 shows a similar dynamic IFT measurement done on Gemini molecule C 14 -C 4 -C 14 .
  • An IFT reduction was once again observed with increasing temperature.
  • the IFT values measured for C 14 -C 4 -C 14 are considerably lower that those of C 14 -C 2 -C 14 .
  • FIG. 7 shows more IFT results on C 14 -C 2 -C 14 and C 14 -C 4 -C 14 at 55°C with different pure hydrocarbons as the oil phase.
  • CI 2 dodecane
  • FIG. 7 shows more IFT results on C 14 -C 2 -C 14 and C 14 -C 4 -C 14 at 55°C with different pure hydrocarbons as the oil phase.
  • FIG. 8 shows the gradual improvement on lowering IFT values with a series of Gemini surfactants, C 14 -C 2 -C 14 , C14-C4-C14 and C16-C4-C16.
  • FIG. 9 and FIG. 10 show the effect of salinity and hardness on IFT measurements.
  • Gemini surfactants are extremely salinity and hardness tolerant: no phase separation or precipitation was observed in aqueous solutions with salinity up to 250,000 ppm ( ⁇ 25% NaCl) and hardness up to 150,000 ppm ( ⁇ 5% CaCl 2 ). Under high salinity and hardness conditions, ultra-low IFT ( ⁇ 0.01 dynes/cm) values were obtained, which has very important practical implication since most conventional surfactants do not work well under such harsh environments.
  • FIG. 1 1 shows the synergy between two Gemini molecules and a hydrophobic surfactant (Petrostep A-l from Stepan, Ci 5 _ig BABS, branched alkyl benzene sulfonate).
  • a hydrophobic surfactant Petrostep A-l from Stepan, Ci 5 _ig BABS, branched alkyl benzene sulfonate.
  • This example also broadens the applicability of traditionally used EOR surfactants and hydrophobic surfactants, such as BABS (branched-), LABS (linear-), alkyl toluene sulfontes, and alkyl xylene sulfonates.
  • EOR surfactants and hydrophobic surfactants such as BABS (branched-), LABS (linear-), alkyl toluene sulfontes, and alkyl xylene sulfonates.
  • Gemini surfactants as co-solvents or co-surfactants can also be seen here.
  • FIG. 12 shows the viscosifying capability of an example Gemini molecule, C16-C4-C16.
  • C16-C4-C16 was dissolved in DI water and no salts were added.
  • a sharp increase of apparent viscosity was observed, which could potentially indicate a spherical-to-wormlike micelle transition.
  • conventional surfactant aqueous solutions usually behave as Newtonian liquids with viscosities only slightly greater than that of water.
  • FIG. 13 illustrates the effect of shear rate on the viscosity of C16-C4-C16 at different concentrations. A shear thinning effect was observed here. The ability of Gemini molecules to develop substantial viscosity was again confirmed by these results.
  • the selected anionic surfactant comprises at least one of (n-C 15 H3o) 2 (CH 2 OCH 2 CH 2 CH 2 CH 2 OCH 2 )(OC 2 H 4 S0 4 Na) 2 (n-C 13 H 26 ) 2 (CH 2 OCH 2 CH 2 OCH 2 )(OC 2 H 4 S0 4 Na) 2 or (n-C 13 H 26 ) 2 (CH 2 OCH 2 CH 2 CH 2 CH 2 OCH 2 )(OC 2 H 4 S0 4 Na) 2 .
  • the unique and versatile structure of the anionic surfactants of the present invention namely ultralow critical micelle concentrations (CMC), very high surface activities, novel rheological properties and extreme water solubility and hard-water tolerance make them very attractive candidates for EOR applications particularly in difficult reservoirs with saline, hard formation brines thus significantly broadening the application scope for conventional chemical EOR methods.
  • CMC critical micelle concentrations
  • novel rheological properties and extreme water solubility and hard-water tolerance make them very attractive candidates for EOR applications particularly in difficult reservoirs with saline, hard formation brines thus significantly broadening the application scope for conventional chemical EOR methods.
  • the single component formulation technology described hereinabove greatly simplifies the whole EOR design process in addition to providing enhanced cost benefits.
  • compositions of the invention can be used to achieve methods of the invention.
  • the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.
  • the term “or combinations thereof as used herein refers to all permutations and combinations of the listed items preceding the term.
  • A, B, C, or combinations thereof is intended to include at least one of: A, B, C, AB, AC, BC, or ABC, and if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB.
  • expressly included are combinations that contain repeats of one or more item or term, such as BB, AAA, MB, BBC, AAABCCCC, CBBAAA, CABABB, and so forth.
  • BB BB
  • AAA AAA
  • MB BBC
  • AAABCCCCCC CBBAAA
  • CABABB CABABB
  • compositions and/or methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of this invention have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations may be applied to the compositions and/or methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit and scope of the invention. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the invention as defined by the appended claims.

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Abstract

L'invention porte sur des compositions et applications d'une nouvelle famille de tensio-actifs anioniques pour utilisation dans des applications en récupération assistée ou améliorée du pétrole (EOR ou IOR). La structure unique et universelle de ces tensio-actifs leur confère quelques propriétés très intéressantes, parmi lesquelles des valeurs extrêmement faibles de la concentration critique pour la formation de micelles (CMC), des activités de surface très élevées, de nouvelles propriétés rhéologiques, une solubilité extrêmement grande dans l'eau et une tolérance à l'eau dure. Les tensio-actifs de la présente invention peuvent être appliqués à des opérations d'EOR chimiques dans des réservoirs pétroliers ayant une très grande salinité et/ou une très grande dureté, ce qui élargit significativement les applications possibles des méthodes EOR chimiques classiques. La technologie de la présente invention présente le potentiel de réduire sensiblement le coût des procédés EOR, car les concentrations des tensio-actifs qu'il faut utiliser sont réduites d'un ordre de grandeur et, dans certains cas, des polymères peuvent ne pas être nécessaires. En outre, les tensioactifs de la présente invention élargissent la gamme potentielle d'applications possibles de ces tensio-actifs à des procédés EOR ou IOR dans des réservoirs à haute salinité et haute température.
PCT/US2011/025618 2010-02-25 2011-02-21 Compositions de tensio-actifs anioniques tolérantes aux sels, pour des applications en récupération assistée ou améliorée du pétrole (eor ou ior) WO2011106287A1 (fr)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102876313A (zh) * 2012-10-26 2013-01-16 四川光亚聚合物化工有限公司 疏水缔合聚合物—复合表面活性剂二元复合驱体系及方法
CN103215018A (zh) * 2012-12-17 2013-07-24 江南大学 一类双长链非离子型无碱驱油用表面活性剂的制备和应用
WO2014055158A1 (fr) * 2012-10-04 2014-04-10 Board Of Regents, The University Of Texas System Compositions de tensioactif anionique tolérant au sel pour applications de récupération assistée du pétrole (rap)
CN104560000A (zh) * 2013-10-28 2015-04-29 中国石油化工股份有限公司 压裂液降阻剂组合物
CN104559999A (zh) * 2013-10-28 2015-04-29 中国石油化工股份有限公司 压裂液降阻剂及其应用
CN104592966A (zh) * 2014-12-23 2015-05-06 青岛大学 一种以地沟油为原料制备稠油降粘剂的方法
CN104632160A (zh) * 2015-02-09 2015-05-20 中国石油大学(华东) 一种考虑井间差异的二元复合驱后续水驱阶段的提液方法
WO2018005341A1 (fr) * 2016-06-28 2018-01-04 Ecolab USA, Inc. Composition, procédé et utilisation pour la récupération assistée du pétrole
WO2019186218A1 (fr) * 2018-03-29 2019-10-03 Mol Magyar Olaj- És Gázipari Nyilvánosan Működő Részvénytársaság Compositions de polymère-tensioactif pour un processus de récupération assistée du pétrole
US10767104B2 (en) 2015-02-27 2020-09-08 Ecolab Usa Inc. Compositions for enhanced oil recovery
US10808165B2 (en) 2016-05-13 2020-10-20 Championx Usa Inc. Corrosion inhibitor compositions and methods of using same
CN115305073A (zh) * 2022-07-14 2022-11-08 江苏海洋大学 一种用于地层卤水配制减阻水的双子表面活性剂及其制法
CN116102093A (zh) * 2022-11-23 2023-05-12 吉林大学 一种用于修复含水层中氯代烃污染的复合增溶材料及其制备和应用方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997451A (en) * 1973-08-10 1976-12-14 Marathon Oil Company Sulfonate blends useful for improved oil recovery
WO1996035663A1 (fr) * 1995-05-11 1996-11-14 Rhone-Poulenc Chimie Alkyl ether sulfates oligomeriques et leurs utilisations dans des compositions nettoyantes
US5643864A (en) * 1994-08-19 1997-07-01 Rhone-Poulenc, Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997451A (en) * 1973-08-10 1976-12-14 Marathon Oil Company Sulfonate blends useful for improved oil recovery
US5643864A (en) * 1994-08-19 1997-07-01 Rhone-Poulenc, Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups
WO1996035663A1 (fr) * 1995-05-11 1996-11-14 Rhone-Poulenc Chimie Alkyl ether sulfates oligomeriques et leurs utilisations dans des compositions nettoyantes

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
LIU, P. ET AL.: "Synthesis of Disodium 1,omega-Di-n-alkyl 1,omega-Disulfate Surfactants", JINGXI HUAGONG, vol. 25, no. 12, 2008, pages 1179 - 1182 *
RENOUF, P. ET AL.: "Synthesis and surface-active properties of a series of new anionic gemini compounds", CHEMISTRY AND PHYSICS OF LIPIDS, vol. 99, 1999, pages 21 - 32 *
RIST, O. ET AL.: "Synthesis of Novel Diammonium Gemini Surfactants", MOLECULES, vol. 6, 2001, pages 979 - 987 *
SHUKLA, D. ET AL.: "Anionic Gemini Surfactants: A Distinct Class of Surfactants", JOURNAL OF OLEO SCIENCE, vol. 55, no. 5, 2006, pages 215 - 226 *
TAN, Z.: "Study on Characteristics and Salt-endurance Activity of Gemini Surfactant", JINGXI YU ZHUANYONG HUAXUEPIN, vol. 14, 2006, pages 50 - 54 *

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WO2014055158A1 (fr) * 2012-10-04 2014-04-10 Board Of Regents, The University Of Texas System Compositions de tensioactif anionique tolérant au sel pour applications de récupération assistée du pétrole (rap)
CN102876313B (zh) * 2012-10-26 2014-07-30 四川光亚聚合物化工有限公司 疏水缔合聚合物—复合表面活性剂二元复合驱体系及方法
CN102876313A (zh) * 2012-10-26 2013-01-16 四川光亚聚合物化工有限公司 疏水缔合聚合物—复合表面活性剂二元复合驱体系及方法
CN103215018B (zh) * 2012-12-17 2016-08-03 江南大学 一类双长链非离子型无碱驱油用表面活性剂的制备和应用
CN103215018A (zh) * 2012-12-17 2013-07-24 江南大学 一类双长链非离子型无碱驱油用表面活性剂的制备和应用
CN104560000B (zh) * 2013-10-28 2017-08-11 中国石油化工股份有限公司 压裂液降阻剂组合物
CN104559999A (zh) * 2013-10-28 2015-04-29 中国石油化工股份有限公司 压裂液降阻剂及其应用
CN104560000A (zh) * 2013-10-28 2015-04-29 中国石油化工股份有限公司 压裂液降阻剂组合物
CN104559999B (zh) * 2013-10-28 2017-08-11 中国石油化工股份有限公司 压裂液降阻剂及其应用
CN104592966A (zh) * 2014-12-23 2015-05-06 青岛大学 一种以地沟油为原料制备稠油降粘剂的方法
CN104632160A (zh) * 2015-02-09 2015-05-20 中国石油大学(华东) 一种考虑井间差异的二元复合驱后续水驱阶段的提液方法
CN104632160B (zh) * 2015-02-09 2016-03-23 中国石油大学(华东) 一种考虑井间差异的二元复合驱后续水驱阶段的提液方法
US10767104B2 (en) 2015-02-27 2020-09-08 Ecolab Usa Inc. Compositions for enhanced oil recovery
US10808165B2 (en) 2016-05-13 2020-10-20 Championx Usa Inc. Corrosion inhibitor compositions and methods of using same
WO2018005341A1 (fr) * 2016-06-28 2018-01-04 Ecolab USA, Inc. Composition, procédé et utilisation pour la récupération assistée du pétrole
US11203709B2 (en) 2016-06-28 2021-12-21 Championx Usa Inc. Compositions for enhanced oil recovery
US11912925B2 (en) 2016-06-28 2024-02-27 Championx Usa Inc. Compositions for enhanced oil recovery
WO2019186218A1 (fr) * 2018-03-29 2019-10-03 Mol Magyar Olaj- És Gázipari Nyilvánosan Működő Részvénytársaság Compositions de polymère-tensioactif pour un processus de récupération assistée du pétrole
US11781059B2 (en) 2018-03-29 2023-10-10 MOL Magyar Olaj és Gázipari Nyilvánosan MüködöRészvénytársaág Polymer-surfactant compositions for enhanced oil recovery process
CN115305073A (zh) * 2022-07-14 2022-11-08 江苏海洋大学 一种用于地层卤水配制减阻水的双子表面活性剂及其制法
CN116102093A (zh) * 2022-11-23 2023-05-12 吉林大学 一种用于修复含水层中氯代烃污染的复合增溶材料及其制备和应用方法

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