EP3440060A1 - Chemical products for surface protection - Google Patents
Chemical products for surface protectionInfo
- Publication number
- EP3440060A1 EP3440060A1 EP16866896.0A EP16866896A EP3440060A1 EP 3440060 A1 EP3440060 A1 EP 3440060A1 EP 16866896 A EP16866896 A EP 16866896A EP 3440060 A1 EP3440060 A1 EP 3440060A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- compound
- alkyl
- weight
- independently selected
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
Classifications
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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
- C09K8/52—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
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/12—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F14/00—Inhibiting incrustation in apparatus for heating liquids for physical or chemical purposes
- C23F14/02—Inhibiting incrustation in apparatus for heating liquids for physical or chemical purposes by chemical means
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/02—Non-contaminated water, e.g. for industrial water supply
- C02F2103/023—Water in cooling circuits
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/10—Nature of the water, waste water, sewage or sludge to be treated from quarries or from mining activities
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
- C02F2103/365—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds from petrochemical industry (e.g. refineries)
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/20—Prevention of biofouling
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2305/00—Use of specific compounds during water treatment
- C02F2305/04—Surfactants, used as part of a formulation or alone
Definitions
- SAGD steam-assisted gravity drainage
- metal components are often exposed to substances that include hydrocarbons and thus cause fouling of the components.
- hot steam is introduced into the ground via a top injection well.
- the top well descends down to a deep level below the surface (for example, into oil sands) and then extends horizontally to provide steam to heat oil containing material to a temperature at which it can flow (for example, down via gravity) to a bottom production well.
- the oil and steam/water mixture is then pumped from a bottom well to the surface where the oil containing mixture may be processed for oil recovery and recycling of the process water.
- heat exchanger fouling is in the crude oil refining process.
- SAGD crude oil refining process.
- higher temperature used in refining process also results in coking, polymerization, among others.
- Ri and R 2 are each independently selected from -H, d-C ⁇ alkyl, Ci-C 2 4 aminoalkyl, Ci-C 24 alkanoalkyl, and Ci-C 36 alkylcarboxy
- R 3 , R 4 , R5, and R 6 are each independently selected from -H, C1-C4 alkyl, and C!-C 4 alkylcarboxy
- R9 and Rio are each independently selected from -H, C1-C24 alkyl, Ci-C 24 aminoalkyl, C ⁇ C ⁇ alkanoalkyl, and C -C 36 alkylcarboxy, -NHRi, -NHR 2 , -NHC(0)Ri, and -NHC(0)R 2 ;
- R9 is selected from -NHRi, -NHC(0)R 2 , -ORi, and - OC(0)R 2
- Rio is selected from -NHR 2 , -NHRi, -NHC(0)R 2 , -OR 2 ,— ORi, and - OC(0)Ri
- Ri, R 2 , R 7 and R 8 are each independently selected from -H, C1-C24 alkyl, Ci- C 24 aminoalkyl, C1-C24 alkanoalkyl, and Ci-C 36 alkylcarboxy
- R 3 , 4, R 5 , R 6 are each independently selected from -H, Ci-C 4 alkyl, and C!-C 4 alkylcarboxy; and
- Ri and R 2 are each independently selected from - H, d-C 2 4 alkyl, C1-C24 aminoalkyl, C1-C24 alkanoalkyl, and CH 2 CH 2 NHR 3
- R 3 is selected from the group of: -H, -C(0)C(R4R 5 R6), -CH 2 CH(0H)CH 2 0C(0)C(R 4 R 5 R 6 )
- R 4 , Rs and R 6 are each independently selected from C 3 -d9, -C(0)C(CH 3 )R 7 , and -C(0)R 7
- R 7 is a C 3 -Ci9 arylalkyl
- a method of treating fouling of a metallic component used in an oil recovery system comprises contacting the metallic component with the aforementioned composition and contacting the metallic component with a hydrocarbon-containing process fluid stream.
- FIG. 2 is a schematic of an experimental test set-up for testing the compositions according to one implementation of the present disclosure
- FIG. 4 is a plot of mass of deposit recorded as a function of anti-fouling concentration for a composition containing Compound No. (V-B).
- V-B Compound No.
- the number of carbon atoms in a substituent can be indicated by the prefix "CA-B" where A is the minimum and B is the maximum number of carbon atoms in the substituent.
- H denotes a single hydrogen atom and may be used interchangeably with the symbol “-H”.
- “H” may be attached, for example, to an oxygen atom to form a "hydroxy” radical (-OH), or two "H” atoms may be attached to a carbon atom to form a “methylene” (-CH 2 -) radical.
- alkyl embraces a linear or branched acyclic alkyl radical containing from 1 to about 24 carbon atoms.
- alkyl is a Ci- 24 alkyl, C 1-20 alkyl, Ci-i& alkyl C 1-10 alkyl, Ci -6 alkyl or C 1-3 alkyl radical.
- alkyl include, but are not limited ethyl, ethyl, propyl, isopropyl, butyl, isobutyl, ter/-butyl, ⁇ ec-butyl, pentan-3-yl ) and the like.
- aminoalkyl embraces an amino radical attached to a parent molecular scaffold through an alkyl radical (for example, NH 2 -alkyl-scaffold).
- alkylcarboxy embraces the COOR group, where R is alkyl or substituted alkyl.
- aryl refers to any monocyclic, bicyclic or tricyclic cyclized carbon radical, wherein at least one ring is aromatic. An aromatic radical may be fused to a non- aromatic cycloalkyl or heterocyclyl radical. Examples of aryl include phenyl and naphthyl.
- arylalkyl embraces aryl attached to a parent molecular scaffold through alkyl.
- arylalkyl include benzyl, diphenylmethyl, triphenylmethyl, phenylethyl and diphenylethyl.
- benzyl and phenylmethyl may be used interchangeably.
- 105 includes at least from 104.5 to 105.49.
- all lists are inclusive of combinations of two or more members of the list. All ranges from a parameter described as “at least,” “greater than,” “greater than or equal to” or similarly, to a parameter described as “at most,” “up to,” “less than,” “less than or equal to” or similarly are preferred ranges regardless of the relative degree of preference indicated for each parameter. Thus, a range that has an advantageous lower limit combined with a most preferred upper limit is preferred for the practice of the implementations described herein. All amounts, ratios, proportions and other measurements are by weight unless stated otherwise. All percentages refer to weight percent based on total composition according to the practice of the present disclosure unless stated otherwise.
- Some implementations of the present disclosure prevent, reduce or at least slow equipment fouling using passivation as a treatment prior to contacting metallic components with hydrocarbon containing fluid, that is, an environment where fouling occurs.
- one implementation includes a method of passivating heat exchangers, such as in a SAGD process, or systems using the compositions and compounds of the present disclosure.
- the composition may be applied to a component prior to its first inclusion in an online system or following placing the system offline for maintenance.
- the composition may be used to treat metallic equipment surface(s), for example, via contacting them with a suspension or solution of the composition described herein, prior placing the system online.
- the method may further include treatment of the process fluid, for example, via injection or batch treatment of the composition with the compositions described herein into the process fluid.
- composition of the present disclosure may be applied in a variety of ways.
- the composition described herein can be applied in batch treatments or continuously injected into the process fluid during operation.
- Another implementation described herein includes, in addition to or as an alternative to treatment prior to placing the system online, a process of continuously, periodically, or intermittently providing the composition to an ongoing process, for example, via introduction of the composition of the present disclosure into the process flow (for example, into an online S AGD process flow) such that the metallic surface(s) are exposed to the composition on a continuous, periodic or intermittent basis.
- Another implementation of the present disclosure includes adding a maintenance dose of the composition of the present disclosure to the process fluid alone or in combination with other treatment, for example, after component or equipment cleaning.
- a maintenance dose of the composition of the present disclosure provides an added benefit of preventing corrosion in other system components that have not been treated or treated after cleaning, such as piping, even if fouling is not of primary concern.
- compositions alone or in combination with additional compounds, in the cleaning product used in the cleaning liquid used in a mechanical/chemical cleaning process which could be agitation, pumping, ultrasonic baths, and other devices.
- compositions described herein serve as scale inhibitors in oil and gas production since they are able to reduce the surface energy of metals resulting in reduced deposits.
- compositions described herein serve as shale inhibitors in oil and gas production due to their strong adhesion with clay surfaces and their strong water repelling hydrophobic tails.
- compositions described herein serve as hydrate inhibitors in oil and gas production due to their strong adhesion with clathrate hydrates and their strong water repelling hydrophobic tails that block the agglomeration of the hydrates.
- FIG. 1 is a schematic of an exemplary production system 100 for steam assisted oil recovery utilizing compositions according to implementations of the present disclosure.
- the exemplary production system 100 includes a boiler feed antifouling composition injector 110, a pump 120, a steam generator 130, such as a once-through steam generator (OTSG), an injection well 140, a production well 150, and a separator 160. While illustrated in an exemplary SAGD configuration, other techniques, such as cyclic steam stimulation, solvent assisted SAGD, or steam drive, may employ the steam generated as described herein.
- the injection well 140 may extend in a horizontal direction and the production well 150 may also extend in the horizontal direction.
- the antifouling composition injector 110 therefore adds the composition of the present disclosure to the water prior to the water entering the steam generator 130.
- the invention contemplates isomers of the compound structures, such as compound structures having isomers of ortho (o), meta (m) and/or para (p) positions for one or more substituents.
- a mixture of one or more C 5 -C 2 2 neo-acids for example, a mixture of Cio-C 19 neo-acids or a mixture of C 9 -Ci 3 neo-acids, may be used for the C 5 -C 22 neo-acid described herein.
- compositions comprising at least one of the following structures of Compounds (I)-(VI), isomers thereof, and mixtures thereof is provided.
- the composition of the present disclosure comprise a generic formula and optionally salts and isomers thereof as defined by the structure of Compound (I):
- Ri is selected from -OH and -N3 ⁇ 4 and R 2 is selected from -H, C1-C18 alkyl, C1-C24 aminoalkyl, Ci-C 24 alkanoalkyl, -S0 3 " , -CH 2 C(0)0 ' , -P(OH)0 2 " and -CH 2 CH 2 C(0)OH.
- Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- Compound (I-D) 2 is selected from -H, Ci-C 18 alkyl, d-C 24 aminoalkyl, C1-C24 alkanoalkyl, -SO3-, -CH 2 C(0)0-, -P(OH)0 2 " and -CH 2 CH 2 C(0)OH.
- Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- composition of Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- composition of Compound (I) is defined by the following structure and optionally salts and isomers thereof:
- composition of the present disclosure comprise a generic formula and optionally salts and isomers thereof as defined by the structure of Compound (II):
- Ri and R 2 are each independently selected from -H, d-C 2 alkyl, C1-C24 aminoalkyl, Ci-C 24 alkanoalkyl, and Ci-C 36 alkylcarboxy.
- R 3 , R4, R 5 , and R 6 are each independently selected from -H, 0-C 4 alkyl, and C1-C4 alkylcarboxy.
- R9 and R 10 are each independently selected from -H, Ci- C24 alkyl, Ci-C 2 4 aminoalkyl, C 1 -C 2 4 alkanoalkyl, and Ci-C 36 alkylcarboxy, -NHR l5 - NHR 2 , -NHC(0)Ri, and -NHC(0)R 2 .
- Compound (II) is defined the structures of Compounds (II- A), (II-B), and (II-C) and optionally salts and isomers thereof:
- R and R 2 are each independently selected from -H, C 1 -C 2 4 alkyl, C1-C24 aminoalkyl, Ci-C 24 alkanoalkyl, and Ct-C ⁇ alkylcarboxy.
- R3, R4, Rs, and R 6 are each independently selected from -H, d-C 4 alkyl, and Ci-C 4 alkylcarboxy.
- composition of the present disclosure comprises a generic formula and optionally salts and isomers thereof as defined by the structure of Compound (III):
- R 9 is selected from -NHRi, -NHC(0)R 2 , -ORi, and - OC(0)R 2 .
- Rio is selected from -NHR 2 , -NHRi, -NHC(0)R 2 , -OR 2 , - -ORi, and -OC(0)R!.
- Ri, R 2 , R7 and R 8 are each independently selected from -H, Ci-C 24 alkyl, Ci-C 24 aminoalkyl, C 1 -C 2 4 alkanoalkyl, and d-C 3 6 alkylcarboxy.
- R 3 , R4, R5, R6 are each independently selected from -H, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy.
- R 7 , and R 8 are each independently selected from— H, Ci- C24 alkyl, Ci-C 2 4 aminoalkyl, C1-C24 alkanoalkyl, Ci-C 36 alkylcarboxy, C7-C 20 arylalkyl such as benzyl group, -P(OH)0 2 " and -SO3 " .
- R 7 , and R 8 are each independently selected from -CH 2 C(0)0 " , -CH 2 CH 2 C(0)0-, -P(OH)0 2 " and -S0 3 " .
- Compound (IV-A) is defined by the structures of Compounds (IV-A-1), (IV-A-2), (IV-A-3), (IV-A-4), (IV-A-5), (IV-A-6), (IV-A-7), (IV- A-8), (IV-A-9), (IV-A-10), (IV-A-11), and (IV-A-12) and optionally salts and isomers thereof:
- Ri and R 2 are each independently selected from -H, C 1 -C 24 alkyl, d-C ⁇ aminoalkyl, Ci-C 24 alkanoalkyl, and Ci-C 36 alkylcarboxy.
- Compound (IV) is defined by the structure of Compound (IV-B) and optionally salts and isomers thereof:
- Compound (IV-B) is defined by the structure of Compounds (IV-B-1), (IV-B-2), (IV-B-3), (IV-B-4), and (IV-B-5) and optionally salts and isomers thereof:
- Ri and R 2 are each independently selected from -H, d-C 2 o alkyl, C1-C20 aminoalkyl, and C1-C20 alkanoalkyl.
- R 3 , R 4 , R 5 , R 6 are each independently selected from -H, -OH, Ci-C4 alkyl, and C1-C4 alkylcarboxy.
- Compound (IV) is defined by the structure of Compound (IV-C) and optionally salts and isomers thereof: (IV-C)
- Compound (IV-C) is defined by the structures of Compounds (IV-C-1), (IV-C-2), (IV-C-3), (IV-C-4), (IV-C-5) and (IV-C-6) and optionally salts and isomers thereof:
- Ri, R 2 , R7, and R 8 are each independently selected from -H, C 1 -C 2 4 all yl, Ci-C ⁇ aminoalkyl, Ci-C 2 4 alkanoalkyl, Ci-C 36 alkylcarboxy, -P(OH)0 2 " , -S0 3 " and C 7 -C 2 o arylalkyl such as benzyl group.
- R 3 , R 4 , R 5 , R 6 are each independently selected from -H, -OH, Ci- C 4 allcyl, and Ci-C 4 allcylcarboxy.
- Ri, R 2 , R7, and R 8 are each independently selected from -H, C1-C24 alkyl, d-C 24 aminoalkyl, d-C 24 alkanoalkyl, -P(OH)0 2 " , SO3 and C 7 -C 20 arylalkyl such as benzyl group.
- R 3 , R 4 , R 5 , R 6 are each independently selected from — H, —OH, C1 -C4 alkyl, and C1 -C4 alkylcarboxy.
- Compound (IV-D) is defined by the structures of Compounds (IV-D-1) and (IV-D-2):
- Ri, R 2 , R 7 , and Rg are each independently selected from -H, Ci-C 2 4 alkyl, Ci-C 2 4 aminoalkyl, C 1 -C 24 alkanoalkyl, - P(OH)0 2 " , -S0 3 " and C7-C20 arylalkyl such as benzyl group
- R3, R4, R 5 , R 6 are each independently selected from -H, -OH, C1-C4 alkyl, and C1-C4 alkylcarboxy.
- Compound (IV) is defined by the structure of Compound (IV-E) and optionally salts and isomers thereof:
- Ri and R 2 are each independently selected from H, d- C 24 alkyl, C1-C24 aminoalkyl, and Ci-C 24 alkanoalkyl.
- R3, R4, Rs, R 6 are each independently selected from— H, -OH, Ci-C4 alkyl, and d-C4 alkylcarboxy.
- R7 and Rg are each independently selected from -CH 2 CH 2 NHRi,— CH 2 CH 2 NHR 2 , -CH 2 CH 2 NHC(0)R!, -CH 2 CH 2 NHC(0)R 2 , -CH 2 CH 2 OR!, - CH 2 CH 2 OR 2 , -CH 2 CH 2 OC(0)R l5 and -CH 2 CH 2 OC(0)R 2 .
- Compound (IV-E) is defined by the structure of Compounds (IV-E-1), (IV-E-2), (IV-E-3), (IV-E-4), (IV-E-5) and (IV-E-6) and optionally salts and isomers thereof:
- Ri and R 2 are each independently selected from -H, d-C 24 alkyl, Ci-C 2 4 aminoalkyl, and C1-C24 alkanoalkyl.
- R 3 , R 4 , R5, R6 are each independently selected from -H, -OH, C1-C4 alkyl, and C ⁇ -C4 alkylcarboxy.
- Compound (IV) is defined by the structure of Compound (IV-F):
- R 1 and R 2 are each independently selected from— H, Ci- C 24 alkyl, C ⁇ -Cu aminoalkyl, and Ci-C 2 4 alkanoalkyl.
- R 3 , R4, R 5 , R 6 are each independently selected from -H, -OH, Ci-C 4 alkyl, and Ci-C 4 alkylcarboxy.
- R 7 and R 8 are each independently selected from - CH2CH 2 NHCH2CH(OH)CH 2 OC(0)R 1 , -CH 2 CH2NHCH 2 CH(OH)CH 2 OC(0)R2, CH 2 CH 2 0CH2CH(0H)CH 2 0C(0)R 1 , and -CH 2 CH 2 OCH 2 CH(OH)CH 2 OC(0)R 2 .
- Compound (IV-F) is defined by the structures of Compounds (IV-F-1) and (IV-F-2):
- Ri and R 2 are each independently selected from -H, Ci-C 24 alkyl, Ci-C 2 aminoalkyl, and C1-C24 alkanoalkyl.
- R3, R4, R5, Re are each independently selected from - H, -OH, C1-C4 alkyl, and C1-C4 alkylcarboxy.
- composition of the present disclosure comprises the structure of Compound (V):
- Ri and R 2 are each independently selected from -H, C 1 -C 2 4 alkyl, C!-C 24 aminoalkyl, C1-C24 alkanoalkyl, and -CH 2 CH 2 NHR 3 .
- R3 is selected from the group of: -H, -C(0)C(R 4 R 5 R6), -CH 2 CH(OH)CH 2 OC(0)C(R 4 R 5 R6).
- R4, R5 and R 6 are each independently selected from C3-C19, - C(0)C(CH 3 )R 7 , and -C(0)R 7 .
- R 7 is a C3-C19 arylalkyl.
- Compound (V) is defined by the structures of Compounds (V-A), (V-B), (V-C) and (V-D):
- composition of the present disclosure comprises the structure of Compound (VI) (and isomers thereof):
- the composition may further comprise additional additives to, for example, facilitate handling, enhance solubility of the composition, and avoid operational problems such as foaming and the like.
- additives that may be used in the compositions of the present disclosure include, but are not limited to, at least one of: surfactants, acids, film forming agents, solvents and/or freeze point depressors, scale inhibitors, wetting agents, and alkylene oxides.
- the composition further comprises a surfactant.
- Suitable surfactants that may be used in the compositions of the present disclosure include surface active additives that may be used to formulate antifouling additives, corrosion inhibitors, anti-agglomeration agents, scale inhibitors, and other flow assurance related applications.
- Suitable surfactants also include surface-active additives that stabilize emulsion systems. The surfactants may help disperse the composition into the stream to be treated.
- Suitable surfactants include, but are not necessarily limited to, non-ionic surfactants, anionic surfactants, quaternary ammonium compounds, and cationic surfactants.
- surfactants that may be used in the compositions of the present disclosure include, but are not necessarily limited to, alkoxylated alkyl alcohols and salts thereof and alkoxylated alkyl phenols and salts thereof, alkyl and aryl sulfonates, sulfates, phosphates, carboxylates, polyoxyalkyl glycols, fatty alcohols, polyoxyethylene glycol sorbitan alkyl esters, sorbitan alkyl esters, polysorbates, glucosides, tall oil, dimer/trimer acids, the products of maleated tall oil fatty acids, diethylene glycol ester and their salts, and the like, and combinations thereof.
- surfactants include, but are not necessarily limited to, quaternary amine compounds, quaternary ammonium compounds, amine oxide surfactants, silicone based surfactants, and the like.
- surfactants can be ionic, such as cationic surfactants such as quaternary alkyl amines or salts such as tetrabutylammomium acetate, tetrabutylammonium bromide, tetrabutylammonium nitrate, etc.; anionic surfactants such as sodium lauryl sulfate, sodium lauryl ether sulfate or dodecylbenzenesulfonic acid; or non-ionic surfactants such as polymers or copolymers based on ethylene oxide and propylene oxide and alkoxylates based on substrates such as alkylphenol or alkylphenol based resins, polyamines, nonylphenol ethoxylate, other polyols, or mixtures thereof.
- Exemplary quaternary ammonium based surfactants include alkyl dimethyl benzyl ammonium chloride, dialkyl dimethyl ammonium chloride, didecyl dimethyl ammonium chloride, alkyl dimethyl ethyl benzyl ammonium chloride, or mixtures thereof.
- the surfactant families can also include members from the amphoteric class, such as amine oxides, betaines, etc.
- surfactants that may be used with the compositions of the present disclosure include TERGITOLTM NP-9 Surfactant, TERGITOLTM NP-10 Surfactant, TERGITOLTM NP-15 Suifactant, TEGOSTAB® silicone surfactants, TENAX® WS-5520, and TENAX® WS-5560.
- the at least one surfactant may be present in the composition in an amount greater than about 1% by weight; greater than about 5% by weight; greater than about 10% by weight; greater than about 20% by weight; greater than about 25% by weight; greater than about 30% by weight; greater than about 35% by weight; greater than about 40% by weight; greater than about 45% by weight; greater than about 50% by weight; greater than about 55% by weight; greater than about 60% by weight; greater than about 65% by weight; greater than about 70% by weight; greater than about 75% by weight; greater than about 80% by weight; greater than about 85% by weight relative to the total weight of the composition.
- the at least one surfactant may be present in the composition in an amount less than about 90% by weight; less than about 85% by weight; less than about 80% by weight; less than about 75% by weight; less than about 70% by weight; less than about 65% by weight; less than about 60% by weight; less than about 55% by weight; less than about 50% by weight; less than about 45% by weight; less than about 40% by weight; less than about 35% by weight; less than about 30% by weight; less than about, 25% by weight; less than about 20% by weight; less than about 15% by weight; less than about 10% by weight relative to the total weight of the composition.
- the at least one surfactant may be present in the composition in an amount between about 1% by weight and about 90% by weight; between about 30% by weight and about 70% by weight; between about 40% by weight and about 60% by weight; between about 45% by weight and about 55% by weight, based on the total weight of the composition.
- the composition further comprises an acid.
- Suitable acids include organic acids and inorganic acids that improve water solubility or oil solubility depending upon the application.
- Suitable inorganic acids include hydrochloric acid.
- Suitable organic acids include, but are not limited to, acetic acid, dimerized fatty acids (dicarboxylic acids prepared by dimerizing unsaturated fatty acids obtained from tall oil), trimerized fatty acids, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, tetrachlorophthalic acid, oxalic acid, adipic acid, azelaic acid, sebacic acid, succinic acid, malic acid, glutaric acid, malonic acid, pimelic acid, suberic acid, 2,2-dimethylsuccinic acid, 3,3-dimethylglutaric acid, 2,2- dimethylglutaric acid, maleic acid, fumaric acid
- the at least one acid may be present in an effective amount for improving solubility of the composition.
- the at least one acid may be present in the composition in an amount greater than about 0.001% by weight; greater than about 0.01% by weight; greater than about 5% by weight; greater than about 10% by weight; greater than about 15% by weight; greater than about 20% by weight; greater than about 25% by weight relative to the total weight of the composition.
- the at least one acid may be present in the composition in an amount less than about 30% by weight; less than about 25% by weight; less than about 20% by weight; less than about 15% by weight; less than about 10% by weight; less than about 5% by weight, relative to the total weight of the composition.
- the at least one acid may be present in the composition in an amount between about 5% by weight and about 30% by weight; between about 10% by weight and about 25% by weight; between about 15% by weight and about 20% by weight based on the total weight of the composition.
- the composition further comprises a solvent and/or freeze point depressors.
- Suitable solvents include solvents that will decrease the freezing point of the composition.
- Suitable solvents that may be used in the compositions of the present disclosure include, but are not necessarily limited to, formamide, propylene carbonate, tetrahydrofuran, alcohols, glycols, methanol, isopropanol, ethanol, acetone, toluene, xylene, monobutyl ether, dimethoxyethane, diglyme, naphtha, aprotic solvents such as dimethyl amine and n-methyl pyrrolidone or biodegradable or renewable solvents, and mixtures thereof alone or without water.
- Suitable glycols include ethylene glycol and propylene glycol.
- Suitable alcohols include methanol, ethanol, propanol, ethylene glycol, propylene glycol, and the like can also be used.
- Commercially available examples of solvents that may be used with the compositions of the present disclosure include SolvessoTM 150 Fluid and AugeoTM SL-191.
- the at least one solvent and/or freeze point depressor may be present in the composition in an amount greater than about 10% by weight; greater than about 20% by weight; greater than about 25% by weight; greater than about 30% by weight; greater than about 35% by weight; greater than about 40% by weight; greater than about 45% by weight; greater than about 50%> by weight; greater than about 55% by weight; greater than about 60% by weight; greater than about 65% by weight; greater than about 70% by weight; greater than about 75% by weight relative to the total weight of the composition.
- the at least one solvent may be present in the composition in an amount less than about 80% by weight; less than about 75% by weight; less than about 70% by weight; less than about 65% by weight; less than about 60% by weight; less than about 55% by weight; less than about 50% by weight; less than about 45% by weight; less than about 40% by weight; less than about 35% by weight; less than about 30% by weight; less than about 25% by weight; less than about 20% by weight; less than about 15% by weight relative to the total weight of the composition.
- the at least one solvent may be present in the composition in an amount between about 10% by weight and about 80% by weight; between about 20% by weight and about 70% by weight; between about 30% by weight and about 50% by weight, based on the total weight of the composition.
- the composition further comprises a scale inhibitor.
- Scale inhibitors are added to produced waters from oil fields and gas fields to mitigate precipitation of minerals, especially sparingly soluble salts, present in the produced water that would occur during production and downstream processing of the water.
- the compounds subject to producing scale are referenced as scale formers. Those compounds include but are not limited to hardness, metals, alkalinity (including but not limited to carbonates), sulfates, silica, and combinations thereof.
- Such precipitation (scaling) leads to fouling and plugging of piping, valves, process equipment, and the oil- bearing formation.
- Suitable scale inhibitors that may be used in the compositions of the present disclosure include, but are not necessarily limited to, organophosphates, polyacrylic acid, polymaleic acid, hydrolyzed water-soluble copolymers of maleic anhydride, polycarboxylates, phosphonates, phosphates, sulfonates, polysulfonates, polycarboxylates, polyacrylates, and polyamides, along with the use of polyaspartic acids, and their mixtures with surfactants and emulsifiers for inhibiting or delaying precipitation of scale forming compounds.
- Suitable scale inhibitors include, but are not necessarily limited to, phosphate esters, acetyl enic alcohols, fatty acids and/or alkyl- substituted carboxylic acids and anhydrides, polyacrylic acids, quaternary amines, sulfur- oxygen phosphates, and/or polyphosphate esters.
- the at least one scale inhibitor may be present in an effective amount for mitigating precipitation of minerals occurring during production.
- the at least one scale inhibitor may be present in the composition in an amount greater than about 0.1% by weight; greater than about 1% by weight; greater than about 2% by weight; greater than about 5% by weight; greater than about 10% by weight; greater than about 15% by weight, relative to the total weight of the composition.
- the at least one scale inhibitor may be present in the composition in an amount less than about 20% by weight; less than about 15% by weight; less than about 10% by weight; less than about 5% by weight; less than about 2% by weight; less than about 1% by weight, relative to the total weight of the composition.
- the at least one scale inhibitor may be present in the composition in an amount between about 1% by weight and about 20% by weight; between about 5% by weight and about 15% by weight; between about 5% by weight and about 10% by weight; between about 10% by weight and about 15% by weight, based on the total weight of the composition.
- the composition further comprises a wetting agent.
- Suitable wetting agents in the compositions of the present disclosure include, but are not necessarily limited to, include glycols, silanes, anionic surfactants, cationic surfactants, non-ionic surfactants, and any other wetting agents known in the art.
- the wetting agent is an anionic surfactant, for example, sodium dioctyl sulfosuccinate.
- the at least one wetting agent may be present in an effective amount for lowering the surface tension of the composition.
- the at least one wetting agent may be present in the composition in an amount greater than about 0.001% by weight; greater than about 0.01% by weight; greater than about 0.1% by weight; greater than about 1% by weight; greater than about 2% by weight; greater than about 5% by weight; greater than about 10% by weight; greater than about 15% by weight, relative to the total weight of the composition.
- the at least one wetting agent may be present in the composition in an amount less than about 20% by weight; less than about 15% by weight; less than about 10% by weight; less than about 5% by weight; less than about 2% by weight; less than about 1% by weight, relative to the total weight of the composition.
- the at least one wetting agent may be present in the composition in an amount between about 0.001% by weight and about 20% by weight; between about 0.01% by weight and about 10% by weight; between about 0.1% by weight and about 1% by weight, based on the total weight of the composition.
- the composition further comprises an alkylene oxide.
- an alkylene oxide For example, each of aforementioned general structures containing a primary or secondary amine or hydroxyl functionality can also be subsequently reacted with one or more moles of an alkylene oxide as random or block-copolymers in any ratio or configuration to adjust solubility or optimize chemical performance.
- the alkylene oxide may be selected from ethylene oxide (EO), propylene oxide (PO) or butylene oxides (BO).
- compositions described herein may also include amid intermediates to the imidazolines, especially since the manufactured products may contain unconverted amid and the degree of conversion is a variable that may be adjusted for performance of the implementations described herein.
- Other amines and fatty acids, monoacids, diacids or higher acids and their derivatives can also be used to produce the chemical compounds of this disclosure according to the molecular structures described herein.
- the imidazoline function as indicated in the molecular structures described herein, can exist at any position along the polyethyleneamine chain and is not limited to the positions indicated in the structures above. It is also possible that more than one bisimidazoline link can exist between the same two polyethyleneamine molecules, or even several links with several polyethyleneamine molecules.
- the composition comprises the reaction products of at least one of: (a) terephthalic acid, (b) a neo-acid having the structure (R!R 2 3)-C-COOH, wherein Ri, R 2 and R 3 are each independently selected from linear or branched alkyl groups, the neo-acid may be a C 5 -C 2 2 neoacid, such as a such as a C5-C19 neoacid, for example, a C5-C.10 neoacid, with R1+R2+R3 having a combined 3 to 20 carbon atoms for a C 5 -C 2 2 neoacid, Ri+R2+R 3 having a combined 3 to 17 carbon atoms C5- 9 neoacid, R1+R2+R3 having a combined 3 to 8 carbon atoms and C5-C 10 neoacid, (c) acrylic acid, (d) di
- a mixture of one or more C 5 -C 22 neo-acids for example, a mixture of Cio-C ⁇ neo-acids or a mixture of C9-CB neo-acids, may be used for the C 5 -C 2 2 neo-acid described herein.
- Suitable neo-acids that may be used to form the compositions described herein include C5-C19 neo-acids having the structure (RiR2R3)-C-COOH, wherein R 1 ⁇ R2 and R3 are each independently, linear or branched alkyl groups having together a total of 3 to 17 carbon atoms (for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 or 17 carbon atoms).
- at least one of R 1? R2 and R3 is a methyl group.
- at least two of Ri, R2 and R3 are methyl groups.
- R 1 ⁇ R 2 and R3 are methyl groups.
- Suitable neo-acids that may be used to form the compositions described herein include neo-pentanoic acid, neo-hexanoic acid, neo-heptanoic acid, neo-nonanoic acid, neo-decanoic acid, isomers thereof, and combinations thereof.
- Examples of commercially available neo-acids that may be used with the implementations described herein are available from HEXIONTM under the tradename VersaticTM acid.
- Commercially available VersaticTM acids that may be used with the implementations described herein include VersaticTM Acid 10 and VersaticTM Acid 5.
- Suitable glycidyl esters of neo-acids that may be used to form the compositions described herein have the structure:
- Ri, R 2 and R 3 are each independently linear or branched alkyl groups having together a total of 2 to 9 carbon atoms (for example, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms).
- R 3 is a methyl group and Ri and R 2 together have a total of seven carbon atoms.
- Examples of commercially available glycidyl esters of neo-acids that may be used with the implementations described herein are available from HEXIONTM under the name CarduraTM Glycidyl Ester El OP (a glycidyl ester of VersaticTM acid 10).
- CarduraTM Glycidyl Ester El OP A glycidal ester of VersaticTM Acid 10, commercially available from HEXIONTM.
- VersaticTM Acid 10 A synthetic, highly branched C-10 tertiary carboxylic acid, commercially available from HEXIONTM. Also known as neo-decanoic acid. [00144] Procedure for the synthesis of Compound (V-D):
- Step 1 Step 1 :
- the first test method included a stainless steel coupon that was partially submersed into a glass container equipped with a magnetic stirrer positioned directly below the coupon.
- the glass container contained a fixed batch of process water obtained from a SAGD operating plant.
- FIG. 2 is a schematic diagram of the experimental test set-up 200 for the second test method.
- the second test method was similar, but the coupon was replaced with a stainless steel washer 210 on a stainless steel bolt 220 held in position by a stainless steel nut and placed in the SAGD produced fluid 225.
- the magnetic stirrer 230 was positioned directly below the horizontal washer, creating a high shear condition 240 at the bottom of the washer and a reduced shear rate 250 at the top of the washer.
- a nine-place magnetic stirrer plate was used in both test methods to ensure identical agitation in each test container for each set of experiments. Chemical performance was determined by evaluating the amount of deposited material as a function of time and chemical concentration.
- FIG, 3 shows a graph of mass of deposit recorded as a function of anti-fouling concentration for a formula containing Compound (I-H).
- Stainless steel coupons were exposed to SAGD fluid treated with Compound (I-H) at increasing concentrations for a period of four hours of stirring at 200 RPM at room temperature. The data is a reflection of the average deposit, including both conditions; high and low shear. It was noted that approximately 50% reduction in deposit amount is achieved at an anti-fouling concentration of 50 ppm.
- FIG. 4 shows a graph of mass of deposit recorded as a function of anti-fouling concentration for a formula containing Compound (VII) for a calcium-scaling test. The results are depicted in Table I. Dose, ppm Deposit, mg
- compositions of the present disclosure have demonstrated high effectiveness in reducing deposition of SAGD fluid on the metal surface in laboratory test.
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Abstract
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GB671141A (en) * | 1949-02-11 | 1952-04-30 | American Viscose Corp | Terephthalamide derivatives |
US3696048A (en) * | 1970-04-06 | 1972-10-03 | Universal Oil Prod Co | Corrosion inhibiting composition and use thereof |
JPS4911701B1 (en) * | 1970-12-30 | 1974-03-19 | ||
AU516824B2 (en) * | 1976-02-17 | 1981-06-25 | Ford Motor Company Of Canada Limited | Coagulating coating composition |
US4497702A (en) * | 1982-08-09 | 1985-02-05 | Atlantic Richfield Company | Corrosion inhibition |
USH1043H (en) * | 1990-01-16 | 1992-04-07 | Texaco Chemical Company | Bis-hydroxy diamides and methods therefor |
CA2056976A1 (en) * | 1990-12-05 | 1992-06-06 | Sanehiro Yamamoto | Aromatic polyamide resin composition |
US6488868B1 (en) * | 1999-03-15 | 2002-12-03 | Ondeo Nalco Energy Services, L.P. | Corrosion inhibitor compositions including quaternized compounds having a substituted diethylamino moiety |
US6303079B1 (en) * | 1999-03-15 | 2001-10-16 | Nalco/Exxon Energy Chemicals, L.P. | Corrosion inhibitor compositions |
JP2008505850A (en) * | 2004-02-19 | 2008-02-28 | エール ユニヴァーシティー | Telephtalamide peptide mimetic compounds and methods |
US7951754B2 (en) * | 2007-12-07 | 2011-05-31 | Nalco Company | Environmentally friendly bis-quaternary compounds for inhibiting corrosion and removing hydrocarbonaceous deposits in oil and gas applications |
EP3087216B1 (en) * | 2013-12-27 | 2018-10-10 | Dow Global Technologies LLC | Bis-imidazoline compounds as corrosion inhibitors and preparation thereof |
MX360320B (en) * | 2014-02-13 | 2018-10-05 | Corrosion Y Proteccion S A De C V | Process to obtain mixtures of imidazolines and corrosion inhibitors from coffee waste. |
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