WO2011071497A1 - Tensioactifs à faible tension interfaciale pour des applications pétrochimiques - Google Patents

Tensioactifs à faible tension interfaciale pour des applications pétrochimiques Download PDF

Info

Publication number
WO2011071497A1
WO2011071497A1 PCT/US2009/067498 US2009067498W WO2011071497A1 WO 2011071497 A1 WO2011071497 A1 WO 2011071497A1 US 2009067498 W US2009067498 W US 2009067498W WO 2011071497 A1 WO2011071497 A1 WO 2011071497A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
composition
compound
group
formula
Prior art date
Application number
PCT/US2009/067498
Other languages
English (en)
Inventor
Kristoffer K. Stokes
Michael C. Berg
David Soane
Kevin T. Petersen
John H. Dise
Atul C. Thakrar
Rosa Casado
Original Assignee
Soane Energy, Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Soane Energy, Llc filed Critical Soane Energy, Llc
Priority to BR112012014020A priority Critical patent/BR112012014020A2/pt
Priority to AU2009356244A priority patent/AU2009356244B2/en
Priority to CA2783809A priority patent/CA2783809C/fr
Priority to EP09852135.4A priority patent/EP2510081A4/fr
Priority to PCT/US2009/067498 priority patent/WO2011071497A1/fr
Publication of WO2011071497A1 publication Critical patent/WO2011071497A1/fr

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
    • C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
    • C09K8/524—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning organic depositions, e.g. paraffins or asphaltenes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
    • C10G31/08—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by treating with water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1033—Oil well production fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4062—Geographical aspects, e.g. different process units form a combination process at different geographical locations
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives

Definitions

  • the application relates generally to surfactants useful for petroleum applications.
  • the viscosity affects the speed at which the heavy crude oil can be pumped, decreasing the overall productivity of an oil field. Exploiting certain oil fields or other oil deposits may be economically unfeasible to develop at present because of the transportation-related costs.
  • Surfactants have been widely used in the petroleum industry to ameliorate the effects of crude oil's physical properties.
  • Surfactant molecules consist of hydrophobic and hydrophilic parts. Their amphiphilic nature allows them to be adsorbed at an oil/water interface, forming micelles that allow the interfacial tension between oil and water to be reduced. Examples of low IFT surfactants were described in U.S. Application Serial No. 12/481,072, the contents of which are expressly incorporated by reference herein.
  • Desalting refers to the process of removing salts from oil, making the oil more suitable for further refining.
  • the salts are typically dissolved in water that is associated with oil, so the removal of water has multiple benefits. The presence of water reduces the energy content of oil, and it carries salts that can harm catalyst performance or cause corrosion. Ethoxylated nonylphenols have been used for desalting of crude oil, but these compounds pose hazards to the environment.
  • demulsification can prove to be difficult, as these surfactants are designed for emulsifying purposes. Demulsification typically requires added materials and steps to break up the emulsion, which increases the effective cost of use. Furthermore, the salts present in nature can inactivate many surfactant technologies. In addition, other surfactant technologies for petroleum applications are tailored only to oils of a limited composition.
  • the invention relates to the discovery that novel surfactants and surfactant compositions have good to excellent properties in recovering or extracting oil, such as fossil fuels.
  • the invention relates to a compound havin the formula I:
  • Ar is a substituted or unsubstituted aryl, aralkyl (e.g., benzyl) or heteroaryl group; in some embodiments, Ar is a substituted or unsubstituted aryl or heteroaryl group; preferably a substituted or unsubstituted phenyl group;
  • p is 1 or 2; preferably 2;
  • n and n are independently 0, 1, 2, 3, 4, or 5; preferably 1;
  • each of Gi and G 2 are independently absent, O, S, NR 2 , C(0)0, OC(O), CO, CONR 2 , or NR 2 CO; preferably each Gi and G 2 are independently O or C(0)0; each R 2 is independently H or a lower alkyl; in some embodiments, the lower alkyl is a CI to C5 alkyl;
  • each G 3 is independently absent, (CH 2 ) q or d;
  • q 1, 2, 3, 4 or 5;
  • R is a hydrophilic group; preferably the hydrophilic group is COOH, or a hydrophilic polymer; such as a polyethylene glycol or a polypropyleneoxide;
  • Ri is a saturated or unsaturated hydrophobic aliphatic group; in some embodiments, Ri is C 5 to Ci8 alkyl, alkenyl or alkadienyl, preferably a straight chain C 5 to C 18 alkyl; wherein, when p is 1, Ar is substituted by one or more of OR 2 , SR 2 and N(R 2 ) 2 ; preferably, when p is 1 Ar is substituted by OH, SH or NH 2 .
  • Gi is C(0)0, G 2 is absent and n is 0.
  • G 2 is not absent, and is preferably O or C(0)0.
  • a particularly preferred surfactant is a compound having the formula II:
  • R 5 is a hydrophilic group
  • R4 is a saturated or unsaturated hydrophobic aliphatic group.
  • the invention further relates to a compound having formula III:
  • Gi is selected from the group consisting of S, NR 2 , C(0)0, OC(O), CO, CONR 2 , and NR 2 CO; preferably GI is C(0)0;
  • each R 2 is independently H or a lower alkyl
  • R 21 , R 22 , R 23 , R 24 , and R 25 are each independently, H, OH, halogen, C 1 -C5 alkyl, C 1 -C5 alkoxy, a C 3 -C 7 -cycloalkyl group, a phenyl group optionally substituted by hydroxyl, halogen, lower alkyl or lower alkoxy, or Fragment I having the formula shown below:
  • R l s m and Gi are as defined above;
  • R 2 i, R 22 , R 23 , R 24 , and R 25 is Fragment I or OH
  • a particularly preferred surfactant is a compound having the formula IV:
  • Preferred compounds of formula IV are compounds wherein m is 1 and Ri is a straight chain C 5 to C 18 alkyl.
  • the invention relates to a composition
  • a composition comprising an aromatic compound and a substituted succinic anhydride, wherein the aromatic compound has the Formula VIII:
  • Ar is selected from the group consisting of aryl, arylalkyl and heteroaryl, each optionally substituted;
  • each G 4 is independently selected from the group consisting of OR 2 , SR 2 , N(R 2 ) 2 , COOR 2 , OCOR2, COR 2 , CON(R 2 ) 2 and N(R 2 ) 2 CO;
  • each R 2 is independently selected from the group consisting of H and lower alkyl
  • Rg is a saturated or unsaturated hydrophobic aliphatic group
  • each R 2 is independently selected from the group consisting of H and C1-C6 alkyl.
  • each G 4 is independently selected from OR 2 or NR 2 .
  • the invention is directed to a method preparing a surfactant composition comprising mixing a compound of
  • the invention is directed to a composition
  • a composition comprising an aromatic compound and a substituted succinic anhydride, wherein the aromatic compound is resorcinol;
  • Rg is a saturated or unsaturated hydrophobic aliphatic group.
  • the resorcinol is m-resorcinol.
  • the invention is directed to a composition comprising an aromatic compound and a compound of Formula X wherein
  • Ar is selected from the group consisting of aryl, arylalkyl or heteroaryl; preferably phenyl or benzyl;
  • each G 4 is independently selected from the group consisting of OR 2 , SR 2 , N(R 2 ) 2 , COOR 2 , OCOR2, COR 2 , CON(R 2 ) 2 and N(R 2 ) 2 CO; preferably, OR 2 or N(R 2 ) 2 ; each R 2 is independently selected from the group consisting of H and lower alkyl; Rg is a saturated or unsaturated hydrophobic aliphatic group; and
  • composition comprising Formula X and an aromatic compound further comprises an alkylene oxide, such ethylene oxide or propylene oxide.
  • the invention is a compound having the mula XI):
  • Ar 2 is a substituted or unsubstituted phenyl or benzyl; p is 1 or 2;
  • n 1 or 2;
  • n 0 or 1 ;
  • each Gi is independently selected from the group consisting of OC(O), C(0)0, C(O), C(0)NR2 and NR 2 CO;
  • each G 2 is absent
  • each R 2 is independently H or a lower alkyl
  • each G 3 is independently absent, or (CH 2 ) q ;
  • q 1, 2, 3, 4 or 5;
  • R is a hydrophilic group
  • Ri is a saturated or unsaturated hydrophobic aliphatic group.
  • the invention is directed to a compound having the formula
  • t is 0 or 1 ;
  • G 5 is O or NH
  • the invention is directed to a compound having Formula (XIII):
  • the invention relates to a compound having the Formula XIV:
  • Ar is aryl, arylalkyl and heteroaryl, each optionally substituted; preferably, Ar is phenyl;
  • Each G 5 is independently O or NH
  • L is a hydrophilic polyethylene glycol glycidyl ether
  • M is a hydrophobic glycidylalkyl ether.
  • the invention further relates to a method for extracting oil from an comprising:
  • An oil mixture is a mixture comprising oil and at least one other component.
  • the oil mixture can comprise oil sands, waterborne oil slicks or oil deposits.
  • the methods of the invention can comprise the additional steps of adding water or transporting the mixture via a pipeline.
  • the compounds and compositions of the invention can be used in methods of degreasing machinery, such as those used in oil or bitumen production.
  • FIG. 1 illustrates examples of critical micelle concentration of
  • compositions (a 1 : 1 composition of m-resorcinol and alkylated succinic anhydride (Eka SA 210 brand alkylated succinic anhydride) and a 1 :2 composition of m- resorcinol and alkylated succinic anhydride of formulas shown below; labeled Rl and R2, respectively).
  • FIG. 2 shows a plot of CMC as a function of pH for two compositions, a 1 : 1 composition of m-resorcinol and alkylated succinic anhydride (Eka SA 210 brand alkylated succinic anhydride) and a 1 :2 composition of m-resorcinol and alkylated succinic anhydride (described in more detail in the Examples).
  • Eka SA 210 brand alkylated succinic anhydride a 1 :2 composition of m-resorcinol and alkylated succinic anhydride
  • FIG. 3 compares the capabilities of the surfactant compositions (1 : 1 composition of m-resorcinol and alkylated succinic anhydride (Eka SA 210 brand alkylated succinic anhydride) and a 1 :2 composition of m-resorcinol and alkylated succinic anhydride) in emulsifying and transporting heavy crude oils, measuring the viscosity of diluted bitumen.
  • FIG. 4 shows a magnified image of oil droplets.
  • FIG. 5 is a graph showing emulsion viscosity as a function of percentage (%) surfactant solution content.
  • compositions, systems and methods related to ultra- low interfacial tension (“IFT") surfactants for applications in the petroleum industry are disclosed herein.
  • IFT interfacial tension
  • the present disclosure is based on the discovery that certain ester surfactants and compositions comprising resorcinol and alkenylated succinic anhydride are highly effective surfactants for petroleum applications, and can be used as additives in petroleum processing, oil sands extraction and processing, environmental remediation, enhanced oil recovery, and the like.
  • compositions of particular use in these systems and methods can include at least one compound of the formula (V):
  • Ri is a hydrophobic group as defined above.
  • compositions of particular use in these systems and methods can include at least one compound of formula (VI):
  • R ⁇ and R 7 are each independently a hydrophobic group.
  • compositions of particular use in these systems and methods can include at least one compound of the formula (VII):
  • the surfactant compound has the Formula XI, XII or XIII as shown above.
  • the invention also encompasses compositions comprising an aromatic compound having the Formula VIII and a substituted succinic anhydride having the Formula IX.
  • the invention is directed to compositions comprising an aromatic compound having the Formula VIII and an ether compound having the Formula X.
  • the succinic anhydride of Formula IX and the compound of Formula X are substituted with a hydrophobic aliphatic group.
  • the hydrophobic aliphatic group is selected from the group consisting of alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heteroaryl.
  • the aromatic compound comprises an optionally substituted benzyl or optionally substituted phenyl core.
  • G 4 is selected from the group consisting of OR 2 or N(R 2 ) 2 .
  • the invention is a composition comprising resorcinol (for example, m-resorcinol) and a succinic anhydride having the Formula IX.
  • inventive surfactant compounds comprise an aromatic core with pendant aliphatic hydrophobic and hydrophilic portions.
  • compositions comprise an (i) aromatic compound and (ii) a substituted succinic anhydride or a substituted ether which each are substituted with hydrophobic groups.
  • hydrophobic portion of the surfactant compound or composition can comprise one or more hydrophobic groups or substituents.
  • hydrophilic portion of the inventive compounds can comprise one or more hydrophilic groups or substituents. Attached aliphatic hydrophobic portions or groups can consist of linear or branched, saturated or unsaturated, substituted or unsubstituted higher alkyls.
  • the hydrophobic group can be derived from alkanes with or without internal or terminal alkenes.
  • the higher alkyl comprises at least five carbon atoms. In other embodiments, the higher alkyl is a C 5 to C 18 alkyl, alkenyl or alkadienyl, or C5 to C20 alkyl, alkenyl or alkadienyl, or C8 to C20 alkyl, alkenyl or alkadienyl.
  • Hydrophilic portions or groups can be an ionizable groups, including, for example, amines and carboxylic acids. Hydrophilic groups also include hydrophilic polymers, including, but not limited to, polyalkylamine, poly(ethylene glycol), poly(propylene glycol) or polyethylene glycol/polypropylene glycol copolymers. Nonionic hydrophilic materials such as polyalkylamine, poly(ethylene glycol) or poly(propylene glycol) can be used to increase hydrophilicity or aid stability in salt solutions.
  • the aliphatic groups include saturated or unsaturated carbon chains, preferably between five and twenty units in length, or five and eighteen units in length, or eight and twenty units in length, or hydrogen.
  • the carbon chains can optionally be unsaturated and, when present, reside anywhere along the carbon chain.
  • the aromatic core of the inventive compounds or the compounds in the compositions can be carbocyclic or heterocyclic, monocyclic or polycyclic, substituted or unsubtstituted.
  • Preferred aryl groups can be derived from resorcinol, phenol, phenyl amine, creosol, benzyl alcohol, benzyl amine, naphthalene, anthracene, pyrene, tetrahydronaphthyl, indanyl, idenyl and the like.
  • Heteroaromatic structures such as thiophene, selenophene, silole, pyrrole, pyridine, furan, imidazole, indole, pyrazinyl, pyrimidinyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, furanyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzooxazolyl, quinoxalinyl, and the like can also be used as the aromatic core.
  • substituted refers to substitution by independent replacement of one or more of the hydrogen atoms thereon with substituents including, but not limited to, -OH, -NH 2 , -NH-Ci-Ci 2 -alkyl, -O-C 1 -C 12 - alkyl, -SH, and -S-Ci-Ci 2 -alkyl, C1-C12 alkyl, and C1-C12 alkenyl.
  • the hydrophilic portion of compounds of the invention is one or more ionizable carboxylic acid groups, which groups, in some embodiments, can make up the totality of the hydrophilic portion.
  • the carboxylic acid portions are not enough to effectively stabilize emulsions formed by the mixture of a waterborne suspension of the disclosed surfactant compounds. Addition of a small amount of base (greater than about pH 8 or between a pH of about 8 and about 9) is sufficient to ionize, leaving a more active, emulsion-forming material. The emulsion can later be destabilized by adding acid to the material, removing the charge stabilization and splitting the two incompatible phases.
  • the hydrophilic portion of compounds of the invention is one or more polymers or copolymers containing ether groups. These polymers will impart the compounds with a cloud point. The compounds will display solubility in water at temperatures below the cloud point and, as a consequence, will be able to emulsify oil. However, upon increasing the temperature over the cloud point, the compounds will become less soluble in water and will lose their emulsification properties. This behavior is reversible because no functional groups are cleaved in the process. An example of compounds exhibiting this behavior are compounds having the Formula (XIII).
  • Aromatic (primary or secondary) amines with polyetherglycidyl ethers are: ortho, meta or para phenylene diamine.
  • the polyether can be polyehtyleneglycol diglycidyl ether.
  • Another example of these compounds can be obtained by reacting an aromatic diamine with a hydrophilic polyethylene glycol glycidyl ether and a hydrophobic glycidyl alkyl ether.
  • the resulting product has comprises a rigid aromatic unit in the middle and 2 linear groups hanging from it, one of the groups being hydrophilic and the other hydrophobic.
  • the tunable behavior of the inventive surfactants and surfactant compositions has utility for petroleum-related applications. For example, if the residence time of the oil in a pipeline is known or can be estimated, the amount of base can be calculated and added with the surfactant to cause decomposition begin in the pipeline and separation to occur immediately after the emulsion reaches its destination. This has the benefit of decreasing residence time in a storage facility while the emulsion breaks.
  • surfactant compounds and compositions disclosed herein can be suitable for applications where undesired petroleum products pose an environmental problem. Oil cleanup using surfactant compounds and compositions may be required for two different types of contamination.
  • oil slick dispersant the surfactant compounds and compositions described herein can be used on waterborne slicks, acting as a dispersing agent.
  • the surfactant compounds and compositions will act to disperse the oil into the water body itself and encourage biodegradation through natural decomposition means.
  • a solution of surfactant or surfactant composition can be used to remove physiosorbed crude or refined oils from inorganic rocks, sand, or other substrates as an emulsion.
  • Oil sands comprise heavy petroleum products coating sand and clay, an assemblage that is similar to certain artificial composites that are formed during a man-made oil spill, as described above.
  • the systems and methods described herein can be useful for extracting bitumen from the other components of the tar sands material.
  • mined oil sands are extracted using hot water, a process that causes the less dense bitumen to flow off the sand and float to the surface of a settling tank. This so-called "primary froth" is contaminated with various materials derived from the mined products (solid particles, clay, and sand).
  • surfactants and surfactant compositions in accordance with these systems and methods can further be applied to other aspects of the extraction process, for example in the oil sands strip mining or in-situ operations, where the ability to emulsify the petroleum component of the oil sands ore may enhance the efficiency or economy of separating the bitumen from the insoluble byproducts.
  • Transporting petroleum precursors for further processing is a necessary, though expensive, part of obtaining usable crude oil.
  • petroleum When petroleum is obtained as a heavy crude, it needs to be transported to an upgrading facility for conversion to useful petroleum products.
  • pipeline transport is the most economical means to accomplish this.
  • oil sands When oil sands are used as precursors in the production of synthetic crude oil, they are transported for further processing after extraction and froth treatment through pipelines as a naphtha-diluted bitumen so that they can undergo further upgrading processes, including cracking and coking, amongst other standard refining operations.
  • the heavy oil or oil precursor materials may be transported through pipelines as oil-in-water mixtures or emulsions.
  • Tertiary oil recovery also known as “enhanced” or “improved” oil recovery, makes use of low IFT surfactant and surfactant compositions to produce oil from wells that have stopped producing of their own accord. Injection of a low IFT surfactant into one of these less productive wells can stimulate production from the residual oil left adhered to the surface of porous rocks.
  • the compounds and compositions described herein are useful as low IFT surfactants for EOR. Due to the temperatures and residence time underground, certain esters made in accordance with the invention may be too unstable for these applications.
  • the resident acid groups on the compound of formula (II) are highly sensitive to saline commonly found in well formations.
  • the compound of formula (II) may be particularly suitable for EOR applications:
  • R4 and R 5 are as defined above.
  • R4 can include a linear or branched carbon chain consisting of five to eighteen carbon atoms.
  • substituent R4 can be a saturated or unsaturated carbon chain consisting of five to eighteen carbon atoms.
  • R 5 can include water soluble oligomers such as poly(ethylene glycol) or poly(propylene oxide). By using a small poly(ethylene glycol) as the hydrophilic portion the substituent R 5 , and all ether connectivity, the molecule of formula (II) may desirably withstand the temperature and salinities found underground for the requisite time period.
  • the compositions comprising an aromatic compound of Formula VIII and succinic anhydride having the Formula IX (such as, resorcinol and succinic anhydride having the Formula IX) can be used in EOR applications as described herein.
  • EOR techniques in accordance with these systems and methods can improve the mobility of oil while making the rock reservoir water-wet to improve its permeability and allow for the recovery of oil at an increased rate.
  • EOR systems and methods can involve using thickening polymers that can self-assemble at the oil surface and act as an efficient emulsifier.
  • aqueous fluids can be designed that will increase sweep efficiency and percent recovery for EOR.
  • the efficiency of a displacing fluid can be defined by the mobility ratio as well as the capillary number.
  • the mobility ratio is indicated by Equation 1.
  • Equation 1 k is the permeability of the media and ⁇ is the viscosity of the fluid.
  • the mobility ratio indicates the sweeping efficiency of a displacing fluid. A mobility ratio ⁇ 1 can mobilize oil while >1 cannot.
  • the capillary number is indicated by Equation 2. Equation 2
  • Equation 2 V is the characteristic velocity, ⁇ is the viscosity of the displacing fluid and ⁇ is the IFT.
  • the capillary number is a dimensionless number that characterizes the relationship of viscosity and IFT of two immiscible fluids. Low capillary number indicates capillary forces will determine the flow through the rock reservoir. The percent oil recovery increases as a function of the capillary number of a displacing fluid. Fluids such as water that have a high mobility ratio and low capillary number will take the least tortuous path through the formation and therefore are poor displacing fluids.
  • a surfactant can give a low mobility ratio with a high capillary number as a single component system even in low concentrations. Although in theory, either a low mobility ratio or high capillary number can give 100% oil recovery, this is not true in practice.
  • these systems and methods can provide for a cost effective and efficient method for EOR that improves both the mobility ratio and capillary number of the displacing fluid.
  • an amphiphilic polymer can be used to act as a thickener in the displacing aqueous phase which can self-assemble onto the surface of oil and act as a surfactant in the oil phase.
  • EOR processes must be robust enough to survive the subterranean environments that typically see temperatures in excess of 100°C while salinity and dissolved solids can vary greatly.
  • polymers are selected that can withstand high temperatures without degrading.
  • hydrophilic groups can shield the polymer from changes in water chemistry including multivalent cations.
  • the polymer can be diluted and delivered in a brine solution which can significantly reduce cost.
  • the self-stabilizing polymeric surfactant can serve to hinder precipitation unless in the presence of a strong hydrophobe.
  • the stability of the polymer surfactant is only broken down in the presence of hydrophobic compounds such as oil.
  • a selected polymer would cease to behave as a polymer slug and would become more like a surfactant. It is understood that the presence of a hydrophobe would destabilize the selected polymer, and it could undergo a conformation change to a more stable structure that could effectively emulsify oil. A hydrophobic component of the selected polymer could penetrate the oil-water interface and effectively reduce the IFT. The polymer could also have the effect of slightly reducing the viscosity of the oil in the surrounding area.
  • these systems and methods can include stimuli-responsive surfactants templates produced in polymeric form for EOR applications.
  • a polymer could emulsify or demulsify due to a certain stimulus such as pH or temperature. Demulsification, for example, could be used to improve oil reclamation in an ex-situ process.
  • polymeric agents such as polyimide-amine salts of styrene-maleic anhydride (SMA) copolymers could be used as surfactants in accordance with this disclosure.
  • SMA copolymer having pendant tertiary amine groups containing a salt-forming tertiary nitrogen atom neutralized to the extent of at least about 75 percent with mono-carboxylic acids, having for example an aliphatic chain of at least about 8 carbon atoms, could be used.
  • the polyimide-amine salts useful for EOR can also contain mixed imides, resulting, for example from the reaction of dialkylaminoalkylamines and monoalkyl amines, or mixed imide-amides resulting from the reaction of dialkylaminoalkylamines and dialkylamines.
  • salts can be prepared by converting the anhydride rings of styrene-maleic anhydride copolymers to polyimides containing pendant tertiary amine groups. These pendant tertiary amine groups can be neutralized with monocarboxylic acids to form salts that have useful properties for EOR.
  • Mixed imide forms of these salts can be obtained by reacting primary alkylamines with a minor portion of the anhydride groups of the styrene- maleic anhydride copolymer.
  • mixed imide-amide forms of the salts can be obtained by reacting a minor portion of the copolymer anhydride groups with secondary dialkylamines.
  • useful polymers in accordance with these systems and methods could be formed from polyimide-amine acid salts of styrene-maleic anhydride copolymers containing pendant tertiary amine groups that are neutralized to the extent of at least about 75 percent with sufficient monocarboxylic acid having an aliphatic carbon-to-carbon chain of at least about 8 carbon atoms, preferably as a terminal group.
  • a styrene-maleic anhydride copolymer can be imidized to the extent of at least about 65 percent up to about 100 percent of its anhydride groups, and neutralized with a dialkylaminoalkylamine to the extent of about 75 percent to 100 percent, with the long chain monocarboxylic acid.
  • the styrene-maleic anhydride copolymer polyimide-amine acid salts can also contain imide groups or amide groups up to the extent of about 35 percent of its anhydride groups by reaction with a primary or secondary alkylamine, for instance, of about 8 to 30 carbon atoms.
  • the ratio of styrene to maleic anhydride in the styrene-maleic anhydride copolymer of this invention can be in the range of about 0.1 :1 to 5 : 1 , preferably about 0.5 : 1 to 2: 1 , and most preferably about 1 : 1.
  • the styrene-maleic anhydride copolymer molecular weight can vary from about 400 to 5,000, preferably from about 1,000 to 5,000, and often is in the range of about 1,400 to 2,000.
  • long hydrophilic chains can be attached to the copolymer backbone.
  • Polymers such as those disclosed herein can be used to formulate surfactants that have multipoint interaction with aromatic heavy oil, thus yielding utility in EOR.
  • the polymers can be modified, for example by adding hydrophilic chains (e.g., polypropylene oxide/polyethylene oxide polymeric chains) to promote pulling emulsified oil drops into water.
  • Desalting refers to the process of removing salts from oil, making the oil more suitable for further refining.
  • Salts including magnesium chloride, sodium chloride and calcium chloride can be found in crude oil. If allowed to remain in the crude oil during the refinery operation, the salts can dissociate and the chloride ion can ionize to form hydrochloric acid, which, along with various organic acids found in crude oil, contributes to corrosion in refinery equipment.
  • other metal salts e.g., potassium, nickel, vanadium, copper, iron and zinc
  • Crude oil also contains emulsified water, which contains dissolved salts.
  • Desalting crude oil takes advantage of the fact that the salts dissolve in a water phase, which is separable from the oil phase.
  • Crude oil naturally contains water in emulsion, as mentioned above.
  • additional water may be added to the oil (e.g., in an amount between 5-10% by volume of crude) so that the impurities can further dissolve in the water.
  • the water- in-oil emulsion can be broken with the assistance of emulsion-breaking chemicals and/or by exposing the emulsion to an electrical field that polarizes the water phase, so that the water phase bearing the impurities separates from the petroleum phase.
  • Ethoxylated nonylphenols are a class of nonionic surfactants that have been used for desalting crude oil according to these principles.
  • the surfactant compounds and compositions disclosed herein can facilitate the demulsification of the water-in-oil emulsion, so that the oil phase separates from the water phase, with the water phase carrying the soluble impurities (i.e., the salts).
  • compositions can include one or more ionizable carboxylic acid groups that can be ionized at a basic pH (e.g., >8) to produce an emulsion-sustaining material as described above.
  • a basic pH e.g., >8
  • acid may be added, removing the charge stabilization and allowing the two phases to segregate from each other.
  • the well outflow stream is first separated into its three components: natural gas, crude oil and produced water.
  • the produced water and crude oil can form a stable emulsion that can interfere with ready separation of these two components.
  • water can also be introduced into an oil-bearing formation to apply pressure to the oil within the formation to keep it flowing. Oil that is recovered under these circumstances also contains a water fraction, typically dispersed as a stable emulsion.
  • This stabilized layer of water in oil known as the "rag layer," actually includes multiple phases, such as solid-in-oil dispersions, water-in-oil emulsions, and oil-in- water-in-oil emulsions.
  • Asphaltenes, paraffmic waxes, resins and other high-molecular-weight components of heavy crude exist in a polydisperse balance within the emulsified heavy crude fluid.
  • a change in the temperature, pressure or chemical composition can destabilize the polydisperse crude oil.
  • the heavy and/or polar fractions can separate from the oil mixture into steric colloids, micelles, a separate liquid phase, and/or into a solid precipitate. Asphaltene precipitation causes problems all along the crude oil process.
  • crude oil e.g., asphaltenes and naphthenic acids
  • these components can precipitate out of the crude oil itself and lodge at the bottom of a storage vessel or tank to form a viscous, tarry sludge.
  • These components also become available as emulsifying agents to sustain the water-in-oil emulsions formed as part of the rag layer.
  • the rag layer has a higher density than light crude, so that it tends to sink to the bottom of storage vessels along with the heavy oil components and associated clay/mineral solids, contributing to the buildup of oil sludge, a thick waste material formed from the various deposits sedimenting out from a crude oil mixture.
  • Sludge forms when heavier components of crude oil separate from the liquid hydrocarbon fractions by gravity and sink to the bottom of an oil tank or other containment vessel. Any given storage vessel can contain a significant amount of sludge, which can diminish storage space for useful crude oil and which can otherwise reduce the efficiency of storage tank operation. Sludge may also require removal if the storage vessel is to be maintained, repaired or inspected.
  • Contaminated sediments are formed when oily materials contact sand, soil, rocks, beaches, and the like. In some cases, the spills are from long term gradual releases at industrial sites, and in other cases the spills can be from catastrophic accidental discharges. In either event, the contaminated soils will require remediation to prevent further environmental damage.
  • the contaminated soil can be in the form of oil-soaked sediments, or water/oil mixtures with solids, including emulsions. Since the contaminated soils have features in common with tank bottoms sludges, the same treatment processes may be applied to both cases.
  • the inventive surfactant solution and compositions comprising an amphiphilic surfactant can be used to emulsify heavy crude oil components that have settled as a sludge at the bottom of the oil containment vessel.
  • a surfactant or surfactant composition can be injected into the sludge, thereby forming an oil-in- water emulsion comprising the heavy crude oil components of the sludge, which emulsion can then be removed from the oil containment vessel, thereby desludging it.
  • the sludge to be treated comprises an oil-contaminated sediment that was created by accidental discharge of hydrocarbons onto the ground or a body of water.
  • the sludge to be treated comprises asphaltenes, or it comprises a water-in-oil emulsion.
  • the aqueous surfactant and/or surfactant compositions includes a switchable, "smart" surfactant, which can be injected as an aqueous solution into an oil storage vessel to emulsify the heavy oil sludge into the water phase with minimal agitation.
  • a switchable, "smart" surfactant which can be injected as an aqueous solution into an oil storage vessel to emulsify the heavy oil sludge into the water phase with minimal agitation.
  • Establishing water as the continuous phase of the emulsion for the sludge can decrease the sludge viscosity so that it can be pumped out of the storage vessel into an alternate containment system.
  • the sludge-in- water emulsion can be directed to a distinct separation vessel, where the emulsion can then be broken, yielding a phase-separate two-component system comprised of crude oil fractions suitable for further refining and recovered water suitable for reuse in similar or other projects.
  • the surfactant or surfactant composition will be injected into the heavy oil sludge (including the rag layer), so that the surfactant or surfactant composition can destabilize the heavy oil-water interface to invert the emulsion into the water phase.
  • an amphiphilic, water-soluble polymer can be used that is effective at low concentrations.
  • the resulting water emulsion can be removed from the subject vessel and relocated, for example to a separation vessel. This may take place as a separate step after the first step has been completed. In other embodiments, however, this can take place during the first step.
  • the water emulsion can be siphoned off as it is formed.
  • the water emulsion containing the stabilized oil droplets can be demulsified.
  • a change in the conditions of the water emulsion can change the conformation of the surfactant, so that it breaks into an oil-soluble component and a water-soluble component.
  • the oil-soluble component thus demulsifies the heavy oil droplets, while the water-soluble component remains in the water phase.
  • Surfactant molecules can be designed so that the water-soluble byproduct is non-toxic and environmentally safe.
  • the emulsification and/or separation processes might be carried out at temperatures above ambient, to facilitate flow and emulsification or to cause switching of the surfactant properties.
  • the systems and methods disclosed herein can be adapted for extracting hydrocarbons from the kerogen in oil shale sources.
  • theses systems and methods can mobilize kerogen to allow retorting processes to be carried out at lower temperatures than are presently required.
  • Processes for treating oil shales can include (A) acid etching, (B) kerogen decomposition, and (C) extraction with kerogen-based surfactants.
  • the oil shale sedimentary rock can be treated, or etched, with aqueous acid solutions.
  • organic or inorganic acids can be used.
  • inorganic mineral acids hydroochloric, sulfuric, phosphoric
  • waste acids are used due to lower costs.
  • exposing the oil shale rock material e.g., limestone, nahcolite, etc.
  • the acid treatment may be applied to ex-situ (i.e., mined) oil shale.
  • the acid treatment may be applied to in- situ oil shale.
  • the oil shale can be treated with a solution that induces fracturing or decomposition of the kerogen molecular structure.
  • the solution can contain radical-generating chemicals and or electron transfer generators. The radical and electron transfer generators will break carbon-carbon and ether bonds. This will fractionate the kerogen-producing fragments having lower molecular weights.
  • the acid etching and kerogen decomposition are done concurrently.
  • examples of radical/electron generators can include hydrogen peroxide, ammonium or sodium persulfate, organic peroxides such as benzoyl peroxide, organic azo compounds such as azo-bis isobutyronitrile, zero valent iron, Fenton's reagent, and the like.
  • these reagents can work by breaking bonds (carbon-carbon or ether), resulting in kerogen with lower molecular weight.
  • the goal with this step is that in the next treatment the surfactants will be able to emulsify at least part of the kerogen (the part with lower molecular weight) and the other part with higher molecular weigh will have higher mobility.
  • the mobility of the kerogen is thereby increased because the molecular weight will be lower than the original condition, and also some interactions between the rock and kerogen have been destroyed by the chemical treatment.
  • One product is an emulsion, mixture, or suspension of the lower MW kerogen fractions (degraded kerogen) in water. No retorting of this product is required.
  • the degraded kerogen is extracted with an aqueous surfactant solution and subsequently separated form the surfactant/water solution by use of switchable surfactants.
  • the recovered kerogen will enter the typical refining process.
  • the second product can be the residual rock containing the higher MW fractions of kerogen. This rock will be retorted but at lower temperatures than currently used for oil shales. The recovered kerogen will enter the typical refining process.
  • the oil shale can be treated with surfactants designed to have high affinity for kerogen.
  • the surfactants will preferably have a hydrophilic-lipophilic balance value higher than 10 in order to be able to form oil- in-water (O/W) emulsions, and the surfactants can include ionic or non-ionic types.
  • the structure of the surfactant can be aliphatic and, preferably with a cyclic aliphatic structure.
  • the surfactants can preferably be temperature or pH switchable.
  • the surfactant can be made from fractions or fragments of kerogen that have been recovered from oil shale.
  • the surfactant can be made from structures that mimic the components of kerogen. Some examples are compounds obtained by modifying lignin by reacting some of the hydroxy groups in the lignin with groups that provides more hydrophilic characteristics. Some of these groups can be carboxy terminated polyethylene oxide, succinic acids, etc.
  • Kerogen fragments or fractions can be isolated from oil shale by extraction or distillation, optionally in concert with thermal or chemical decomposition of the kerogen to improve mobility or solubility.
  • the fragments or fractions, once isolated, can be modified with functional groups to convert them to surfactants with an affinity for kerogen.
  • these modifications can include hydrophilic modifications, such as ethoxylation, propoxylation, oxidation, sulfonation, phosphorylation, and modification with other polar groups.
  • the surfactants can be suspended in an aqueous mixture, so that they can emulsify part of the fractionated kerogens, for example, those hydrocarbons having lower molecular weight.
  • the surfactants can increase the mobility inside the rock formation of the remaining kerogen fractions having higher molecular weights. This extraction or mobilization can be aided by the surfactant reducing the interfacial tension between the kerogen fragments and the water phase, or by solubilizing the kerogen fragments.
  • the extraction, chemical treatment processes can are be aided by heating the formation.
  • An object of the invention is to reduce the total energy requirements of recovering kerogen.
  • Eka SA 210 was supplied by EKA Chemicals, Inc., Marietta, GA 30062, USA.
  • ERISYS GE-7 CVC Thermoset Specialties, Moorestown, New Jersey 08057 USA.
  • Example 1 Surfactant compositions comprising an aromatic compound and alkylated succinic anhydride
  • composition was prepared as follows:
  • a 300 ml bomb is charged with resorcinol (5 g, 48 mmol) and Eka SA 210 brand alkylated succinic anhydride (100% C18 chain, 16.8 g., 48 mmol). To this, acetone (150 ml) was added, the vessel is sealed and heated to 80 C for 16 hours.
  • Example 2 Surfactant compositions comprising an aromatic compound and alkylated succinic anhydride
  • composition was prepared as follows:
  • Eka SA 210 (33.7 g, 96 mmol). To this, acetone (150 ml) was added, the vessel sealed, and heated to 80°C for 16 hours. Then, acetone was removed under vacuum.
  • Critical micelle concentration is an important metric with surfactant systems. It is defined as the minimum surfactant concentration that will form micelles. Below this amount, the molecules exist only in a non-aggregated form. Additionally, this number also represents the constant concentration of monomeric molecules in solution. Effectively, it describes a lower limit to usage and is a good first approximation to formulation content.
  • a series of aqueous surfactant dilutions were prepared in deionized water with concentrations between 20 ⁇ and 200 mM.
  • the water surface tension at 22 °C was measured on a KSV 702 tensiometer using the Du Nouy ring method.
  • CMC critical micelle concentration
  • Figure 1 illustrates examples of critical micelle concentration of a composition prepared according to Example 1, termed Rl in the figure.
  • Figure 1 also illustrates examples of critical micelle concentration of a composition prepared according to Formula (II) formula shown below, termed R2 in the figure.
  • Figure 2 shows a plot of CMC as a function of pH for two compositions prepared according to Examples 1 and 2 (Rl and R2, respectively).
  • Example 6 Emulsion stability for oil flow behavior
  • Figure 3 demonstrates that incorporation of an aqueous solution of surfactant can dramatically decrease the viscosity of diluted bitumen.
  • the addition of more than 50 vol% of a dilute aqueous solution of the composition described herein decreases the bitumen viscosity by nearly one thousand times.
  • the energy savings of such a system are significant, but the concomitant increase in flowrate enables much higher throughput and residence time in a pipeline.
  • Example 7 Reaction between alkenylsuccinic anhydride and benzyl alcohol
  • a reactor was charged with benzyl alcohol (4.821 g, 44.58 mmol) and nonenyl succinic anhydride (10 g, 44.58 mmol). The mixture was stirred for about 2.5 hours at 130°C under nitrogen. The product was then analyzed by IR
  • Germanium crystal which showed almost complete disappearance of the anhydride carbonyl peaks (1859 and 1778 cm-1) (i.e., only small traces of the peaks were visible) and the appearance of the ester and acid carbonyl bands (1735 and 1700 cm- 1 respectively).
  • the scheme below illustrates this synthesis:
  • Example 8 Reaction between alkenylsuccinic anhydride and benzyl alcohol
  • a reactor was charged with benzyl alcohol (3.063 g, 28.36 mmol) and Eka SA 210 brand alkylated succinic anhydride (10 g, 28.36 mmol). The mixture was stirred for about 4 hours at 130°C under nitrogen. The product was then analyzed by IR, which showed almost complete disappearance of the anhydride carbonyl peaks (1863 and 1778 cm-1) and the appearance of the ester and acid carbonyl bands (1735 and 1704 cm-1 respectively). The scheme below illustrates this synthesis:
  • Example 9 Reaction between a phenol and an alkenylsuccinic anhydride
  • a reactor was charged with phenol (2.098 g, 22.3 mmol), noneyl succinic anhydride (5 g, 22.3 mmol), p-toluene sulfonic acid (1.92 g, 11.15 mmol) and 35 ml of toluene.
  • the reactor was fitted with a Dean-Stark trap and the reaction mixture was stirred for about 5 hours under reflux.
  • Example 11 Reaction between an alkenylsuccinic anhydride and benzyl amine
  • a reactor was charged with benzyl amine (2.388 g, 22.3 mmol), noneyl succinic anhydride (5 g, 22.3 mmol) and 15 ml of THF. The mixture was stirred for about 1 hour at room temperature, and then the solvent was stripped off under vacuum in a rotary evaporator. The product was then analyzed by IR, which showed almost complete disappearance of the anhydride carbonyl peaks (1859 and 1778 cm- 1) and the appearance of the amide and acid carbonyl bands (1645 and 1548 for amide I and II respectively, and 1723 cm-1 for associated acid). The scheme below illustrates this synthesis:
  • Example 12 Reaction between an alkenylsuccinic anhydride and m- phenylene diamine.
  • a reactor was charged with m-phenylene diamine (1.534 g, 14.2 mmol), Eka SA 210 brand alkylated succinic anhydride (10 g, 28.4 mmol) and 20 ml of THF. The mixture was stirred for about 1.5 hours at RT. Then the solvent was stripped off under vacuum in a rotary evaporator. The product was then analyzed by IR, which showed almost complete disappearance of the anhydride carbonyl peaks (1863 and 1782 cm-1) and the appearance of the amide and acid carbonyl bands
  • Example 15 Surfactant properties
  • FIG. 4 A magnified image of the oil droplets formed in emulsion is presented in Figure 4, showing emulsion of heavy oil (API 15) at 50x magnification using the surfactant of Example 7. During observation, some coalescence of droplets was observed, however, the stability of the emulsion was evident over multiple days.
  • API 15 emulsion of heavy oil
  • Example 7 was prepared in aqueous solution and pH adjusted to 9 by the addition of 1 M sodium hydroxide, to form a surfactant solution.
  • Heavy oil API gravity index 15.0
  • FIG. 5 depicts the viscosity of the resulting emulsion for a given water ratio.
  • surfactant a large drop in viscosity of the heavy oil is observed, even for lower water ratios. An additional drop in viscosity was noted when the volume % of water exceeded 50%.
  • Example 17 Reaction between a phenylene diamine and hydrophobic and hydrophilic glycidyl ether
  • a reactor was charged with m-phenylene diamine (2 g, 18.5 mmol), ERISYS GE-7 brand monoglycidyl ether of a naturally occurring C8-C10 aliphatic alcohol (3.44g, 18.5 mmol), and 15 ml of THF. The mixture was stirred for 2 hours under reflux. Then a solution of polyethylene glycol diglycidyl ether (9.731 g, 18.5 mmol) in 10 ml of THF was added and the reflux continued for additional 4 hours. Then the solvent was stripped off under vacuum. The product was tested qualitatively to assess certain properties. First, the product was dissolved in water to show that it is water-soluble.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une classe de nouveaux tensioactifs qui ont une utilité dans la récupération et/ou l'extraction de pétrole.
PCT/US2009/067498 2009-12-10 2009-12-10 Tensioactifs à faible tension interfaciale pour des applications pétrochimiques WO2011071497A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR112012014020A BR112012014020A2 (pt) 2009-12-10 2009-12-10 composição tensoativa, método para extrair óleo de um mistura de óleos, método para remover água e sais associados de óleo e composto
AU2009356244A AU2009356244B2 (en) 2009-12-10 2009-12-10 Low interfacial tension surfactants for petroleum applications
CA2783809A CA2783809C (fr) 2009-12-10 2009-12-10 Tensioactifs a faible tension interfaciale pour des applications petrochimiques
EP09852135.4A EP2510081A4 (fr) 2009-12-10 2009-12-10 Tensioactifs à faible tension interfaciale pour des applications pétrochimiques
PCT/US2009/067498 WO2011071497A1 (fr) 2009-12-10 2009-12-10 Tensioactifs à faible tension interfaciale pour des applications pétrochimiques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2009/067498 WO2011071497A1 (fr) 2009-12-10 2009-12-10 Tensioactifs à faible tension interfaciale pour des applications pétrochimiques

Publications (1)

Publication Number Publication Date
WO2011071497A1 true WO2011071497A1 (fr) 2011-06-16

Family

ID=44145822

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/067498 WO2011071497A1 (fr) 2009-12-10 2009-12-10 Tensioactifs à faible tension interfaciale pour des applications pétrochimiques

Country Status (5)

Country Link
EP (1) EP2510081A4 (fr)
AU (1) AU2009356244B2 (fr)
BR (1) BR112012014020A2 (fr)
CA (1) CA2783809C (fr)
WO (1) WO2011071497A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11414626B2 (en) 2018-11-30 2022-08-16 Ecolab Usa Inc. Surfactant compositions and use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4300634A (en) * 1979-12-04 1981-11-17 Phillips Petroleum Company Foamable compositions and formations treatment
US5268112A (en) * 1990-12-21 1993-12-07 Union Oil Company Of California Gel-forming composition
US20030222026A1 (en) * 2001-09-04 2003-12-04 Carey Jeffrey M. Use of water soluble demulsifiers in separating hydrocarbon oils from clays
US7534829B2 (en) * 2002-02-26 2009-05-19 Kuraray Co., Ltd. Resin composition and multi-layer structures

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4240970A (en) * 1976-07-28 1980-12-23 Mobil Oil Corporation Reaction products of hydroxy aromatic or alkylphenylether compounds and alkenylsuccinic acid, anhydride, or ester
US7572757B1 (en) * 2004-07-19 2009-08-11 Bj Services Company Method of treating a well with a gel stabilizer
DE102005026716A1 (de) * 2005-06-09 2006-12-28 Basf Ag Tensidmischungen für die tertiäre Erdölförderung
US8227383B2 (en) * 2008-06-09 2012-07-24 Soane Energy, Llc Low interfacial tension surfactants for petroleum applications

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4300634A (en) * 1979-12-04 1981-11-17 Phillips Petroleum Company Foamable compositions and formations treatment
US5268112A (en) * 1990-12-21 1993-12-07 Union Oil Company Of California Gel-forming composition
US20030222026A1 (en) * 2001-09-04 2003-12-04 Carey Jeffrey M. Use of water soluble demulsifiers in separating hydrocarbon oils from clays
US7534829B2 (en) * 2002-02-26 2009-05-19 Kuraray Co., Ltd. Resin composition and multi-layer structures

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2510081A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11414626B2 (en) 2018-11-30 2022-08-16 Ecolab Usa Inc. Surfactant compositions and use thereof
US11807830B2 (en) 2018-11-30 2023-11-07 Ecolab Usa Inc. Surfactant compositions and use thereof

Also Published As

Publication number Publication date
CA2783809C (fr) 2016-11-08
EP2510081A4 (fr) 2015-09-16
CA2783809A1 (fr) 2011-06-16
AU2009356244A1 (en) 2012-07-05
EP2510081A1 (fr) 2012-10-17
AU2009356244B2 (en) 2013-09-12
BR112012014020A2 (pt) 2019-09-24

Similar Documents

Publication Publication Date Title
US9499736B2 (en) Low interfacial tension surfactants for petroleum applications
CA2783831C (fr) Tensioactifs a faible tension interfaciale pour des applications dans le petrole
CA2777755C (fr) Tensioactifs polymeres modifiables destines a mobiliser de l'huile a l'interieur de l'eau
US8227383B2 (en) Low interfacial tension surfactants for petroleum applications
WO2007061722A2 (fr) Procedes de separation et de rupture d’emulsion
EP2561035A1 (fr) Procédé pour éliminer des dépôts d'un puits de pétrole ou de gaz et/ou de structures de surface et/ou d'un équipement relié à ces structures et/ou de formations contenant des hydrocarbures
US9315718B2 (en) Low interfacial tension surfactants for petroleum applications
CA2936365A1 (fr) Desemulsionneur destine a une utilisation dans l'industrie du petrole et du gaz
CA2783809C (fr) Tensioactifs a faible tension interfaciale pour des applications petrochimiques
WO2014071038A1 (fr) Tensioactifs à faible tension interfaciale pour des applications dans le pétrole
EP1497395B1 (fr) Procede d'inversion d'emulsions eau dans l'huile en emulsions huile dans l'eau
CN117957053A (zh) 乳化剂组合物
NO162567B (no) Micellulaer tynnfilmspredende blanding.

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09852135

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2783809

Country of ref document: CA

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2009356244

Country of ref document: AU

ENP Entry into the national phase

Ref document number: 2009356244

Country of ref document: AU

Date of ref document: 20091210

Kind code of ref document: A

REEP Request for entry into the european phase

Ref document number: 2009852135

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2009852135

Country of ref document: EP

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112012014020

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112012014020

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20120611