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US20180312740A1 - Asphaltene dispersant and methods of use thereof - Google Patents

Asphaltene dispersant and methods of use thereof Download PDF

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Publication number
US20180312740A1
US20180312740A1 US15/580,904 US201615580904A US2018312740A1 US 20180312740 A1 US20180312740 A1 US 20180312740A1 US 201615580904 A US201615580904 A US 201615580904A US 2018312740 A1 US2018312740 A1 US 2018312740A1
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Prior art keywords
compound
wellbore fluid
fluid treatment
asphaltene
amino acid
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US15/580,904
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English (en)
Inventor
Avinash Pradyumna Deshpande
Yeshwant Shekhar Khandekar
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MI LLC
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MI LLC
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Publication date
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Priority to US15/580,904 priority Critical patent/US20180312740A1/en
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Abandoned legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C09K8/02—Well-drilling compositions
    • C09K8/03—Specific additives for general use in well-drilling compositions
    • C09K8/035—Organic additives

Definitions

  • Asphaltenes are complex heterocyclic molecules that are present in hydrocarbon fluids. Under reservoir conditions asphaltenes are stabilized by resins. During the production asphaltene precipitation can occur due to number of factors such as changes to pressure, temperature, chemical composition of the crude oil and during stimulation operations. Precipitated asphaltene particles may flocculate and deposit on to pipeline surfaces or equipments to cause plugging problems. Precipitated asphaltene particles can also increase hydrocarbon viscosity which may lead to separation problems. In addition precipitated asphaltene particles can cause pore throat plugging which may cause blockages and lead to lower production rates.
  • aromatic solvents can be added to dissolve asphaltenes.
  • solubility and of asphaltene in aromatic solvents is very low and improper cleaning can lead to possible slow re-precipitations.
  • an asphaltene inhibitor or a dispersant is typically added to the production system.
  • embodiments disclosed herein relate to a wellbore fluid treatment that includes a compound formed from reaction between cyclic anyhydride pendant groups on a polymer backbone with at least one amino acid, neutralized with a nitrogen containing compound.
  • embodiments disclosed herein relate to a method that includes introducing to a hydrocarbon production stream, a compound formed from reaction between cyclic anyhydride pendant groups on a polymer backbone with at least one amino acid, neutralized with a nitrogen containing compound.
  • embodiments disclosed herein relate to a method that includes reacting polybutadiene grafted maleic anhydride with at least one amino acid to produce an intermediate; and reacting the intermediate with an amide, amine, or imidazoline having at least a C4-C24 group to produce a compound.
  • FIG. 1 illustrates an asphaltene dispersant based on polybutadiene grafted maleic anhydride derivative, in accordance with the disclosed embodiments
  • FIGS. 2-4 illustrate synthesis of asphaltene dispersants, in accordance with the disclosed embodiments
  • FIG. 5 illustrates the percentage asphaltene precipitation for a blank and relative percentages of asphaltene dipsersancy for tested dispersants, in accordance with the disclosed embodiments
  • FIG. 6 illustrates the percentage transmission of the blank compared to asphaltene dispersant potted against time, in accordance with disclosed embodiments.
  • Embodiments disclosed herein are directed to methods and compositions for inhibiting or dispersing the deposition of asphaltenes from hydrocarbon fluids within wellbores.
  • methods and compositions in accordance with the present disclosure are directed to inhibiting or dispersing asphaltene deposition for topside and downhole oilfield applications.
  • Treatment fluid compositions of the present disclosure may be used in downhole and surface applications including dispersion of existing residues on wellbore equipment and wellbore surfaces, in addition to inhibition of asphaltene precipitation during production and transportation of various hydrocarbon fluids.
  • asphaltenes may precipitate out of the oil, creating aggregates that may entrain solids, which may initiate the formation of sludges and other insoluble residues.
  • Asphaltene deposits may accumulate on the surfaces of completions equipment and reservoir pore throats, which can lead to production impairment and other operational problems including but not limited to, plugging of equipment, pressure loss, increased utility costs, lost production due to downtime, and downgraded products from insufficient feeds.
  • Asphaltenes are organic materials containing aromatic and naphthenic ring compounds that may come in the form of polyaromatic or polycyclic structures, and which may include a number of alkyl chains and heteroatoms such as nitrogen, sulfur and oxygen. Asphaltenes are often described as the “hydrocarbon fraction,” which contains a wide variety of heavy and polar molecules from crude oils that are soluble in aromatic solvents, but insoluble in normal alkane-based solvents such as pentane or heptane.
  • Asphaltenes exist as a colloidal suspension stabilized by aromatic resins in crude oil.
  • the stability of asphaltic dispersions may depend in part on the ratio of resin to asphaltene molecules, which may be used to estimate potential damage created by asphaltenes.
  • asphaltenes may precipitate as a result of pressure drop, composition changes, pressure depletion above the saturation pressure, temperature changes, shear from turbulent flow, intermixing of incompatible fluids or materials that break the stability of the asphaltic dispersion, and other parameters such as pH, solution carbon dioxide, water cut, electro-kinetic effects.
  • Asphaltene inhibitor and treatment fluid compositions in accordance with the present disclosure may be used as additives that are provided to hydrocarbon mixtures to disperse asphaltene aggregates and/or prevent flocculation of heavy hydrocarbons.
  • Treatment fluids in accordance with the present disclosure may be suitable for use in downhole environments, at the surface, and in pipelines used to transport hydrocarbons.
  • asphaltene inhibitors may be placed into a hydrocarbon production stream at any point, including within the wellbore, at the surface of the well, and during transport of the hydrocarbon stream through pipelines or storage tanks.
  • Asphaltene inhibitor compositions of the present disclosure may be mixed with hydrocarbon fluids either by batch treatment or by continuous injection.
  • asphaltene inhibitors may be used as a wellbore fluid additive, and in other treatment fluids such as squeeze treatments, or fluid loss control pills.
  • compositions in accordance with the present disclosure may inhibitor asphaltene agglomeration under HPHT conditions.
  • treatment compositions may contain an asphaltene inhibitor combined with one or more aromatic solvents.
  • embodiments disclosed herein relate to polymeric asphaltene dispersants formed from reaction between cyclic anyhydride pendant groups on a polymer backbone with at least one amino acid, neutralized with a nitrogen containing compound.
  • the pendant groups may be formed by grafting a cyclic anhydride, such as maleic anhydride, onto a polymer backbone, such as polybutadiene. Grafting may allow for control of the pendant groups throughout the polymer backbone, as compared, for example to polyisobutylene succinic acid (PIBSA) where the polymer includes only one terminal anhydride functionality per molecular.
  • PIBSA polyisobutylene succinic acid
  • the grafted cyclic anhydride may be grafted at an amount ranging from 1 to 20 wt % of the polymer onto which it is being grafted.
  • the cyclic anhydride may be granted at an amount having a lower limit of any of 1, 2, or 3 wt % and an upper limit of any of 6, 8, 10, 15, and 20 wt %, where any lower limit can be used with any upper limit.
  • the pendant cyclic anhydride groups may be reacted with an amino acid to form an intermediate compound which is subsequently neutralized.
  • Amino acids may include, but are not limited to non-proteinogenic amino acids such as anthranilic acid, aminocaproic acid, or ⁇ -aminobutyric acid, as well as the twenty three proteinogenic amino acids, such as lysine, etc.
  • the neutralizer may be a nitrogen containing compound such as an amide, amine, imidazoline to yield the inhibitor/dispersant of the present disclosure.
  • the neutralizer may also include an alkyl chain having at least 4, 6, 8, or 12 carbon atoms up to, for example 18, 20, 22, or 24 carbon atoms, and may be linear, branched, saturated or unsaturated.
  • Such neutralizer may neutralize the acid of the amino acid and also may interact with the asphaltene to assist in the dispersant/inhibition effect.
  • An example of the neutralized (and final) product is shown in FIG. 1 . However, given that variations on the reactants are envisioned, as described above, FIG. 1 is only representative of the structure of the compounds of the present disclosure. Other potential structural formulas include, but are not limited to the final products presented in FIGS. 2-4 .
  • Polymeric asphaltene inhibitors in accordance with the present disclosure may range in molecular weight (Mn) from 900 Da to 100 kDa in some embodiments, and from 2 kDa to 25 kDa in particular embodiments.
  • Asphaltene inhibitors in accordance with the present disclosure may be added to a wellbore fluid formulation at a concentration that may range from 5 ppm to 1,500 ppm of the wellbore fluid in some embodiments, and from 10 ppm to 1,000 ppm in particular embodiments.
  • asphaltene inhibitors may be used in conjunction with one or more aromatic solvents that may increase the dispersion and/or inhibitory effects of the treatment.
  • Aromatic solvents in accordance with the present disclosure may be combined with an asphaltene inhibitor prior to injection downhole or subsequent to the injection of the asphaltene inhibitor or other wellbore fluid.
  • Suitable aromatic solvents of the composition of this invention include benzenes, alkyl benzenes such as toluene, xylene, trimethyl benzene, and the like. While a number of solvents are disclosed, it is also envisioned that other solvents may be selected that are miscible with petroleum fluids such as crude oil, condensates, diesel, and the like.
  • wellbore treatment compositions may contain one or more aromatic solvents at a percent by volume (v %) that ranges from 1 v % to 90 v %.
  • an asphaltene dispersant was prepared by charging 50 g polybutadiene grafted maleic anhydride [1] with number average molecular weight (Mn) of 5500 to a 500 ml reaction flask containing 35.89 g xylene, equipped with overhead stirrer, heating mantle, thermocouple, dean stark trap and water cooler condenser. 0.13 g PTSA catalyst was added. The material was then mixed for 30 min and 3.42 g of Anthranilic acid [2] added. The temperature increased to 145° C. until reflux started. The reaction continued until 0.46 g quantity of water was removed. The reaction then stirred for 30 min. Heating was ceased and reaction mixture [3] cooled.
  • Mn number average molecular weight
  • an asphaltene dispersant was prepared by charging 50 g polybutadiene grafted maleic anhydride [1] with number average molecular weight (Mn) of 5500 to a 500 ml reaction flask containing 56.89 g xylene, equipped with overhead stirrer, heating mantle, thermocouple, dean stark trap and water cooler condenser. 0.13 g PTSA catalyst was added. The material was then mixed for 30 min and 3.28 g of 6-aminocaproic acid [6] added. The temperature increased to 145° C. until reflux started. The reaction continued until 0.46 g quantity of water was removed. The intermediate product [7] was then stirred for 30 min.
  • an asphaltene dispersant was prepared by charging 50 g polybutadiene grafted maleic anhydride [1] with number average molecular weight (Mn) of 5500 to a 500 ml reaction flask containing 54.35 g xylene, equipped with overhead stirrer, heating mantle, thermocouple, dean stark trap and water cooler condenser. 0.13 g PTSA catalyst was added. The material was then mixed for 30 min and 3.28 g of aminocaproic acid [6] added. The temperature was then increased to 145° C. until reflux started. The reaction continued until 0.46 g quantity of water was removed. The reaction mixture intermediate [9] then stirred for 30 min. 8.87 g of imidazoline [4] was then added drop wise while stirring of mixture continued. Reaction was stirred for 1 hr. The final product [10] (115.67 g) was a dark amber color liquid.
  • Asphaltene Dispersant Test is widely used to screen and evaluate asphaltene dispersants in the oil and gas industry. The procedure is used for comparing the asphaltene content of crude oils and evaluating the ability of asphaltene dispersant to disperse asphaltenes within such oils.
  • n-alkane (C5, C7 or C9) is employed as the solvent.
  • N-alkanes are non-polar in nature and promote the precipitation and agglomeration of polar asphaltene molecules.
  • crude oil is mixed with toluene at a ratio of 1:1 for 2 hours.
  • a blank crude oil concentration is determined by adding different concentrations of 1:1 diluted solution as described above in a 10 ml graduated centrifuge tube containing 10 ml of n-alkane. The tubes were allowed to stand for 2 hours. A crude oil concentration was chosen which showed 4-10% asphaltene precipitation.
  • This procedure details the use of a specific piece of optical scanning equipment (Formulaction's TurbiscanTM MA2000) for the evaluation of the static performance of asphaltene dispersants in crude oil by exploiting settling-over-time phenomenon of asphaltenes intentionally driven from solution.
  • the method calls for blending with n-alkane to force the asphaltenes out of solution.
  • a number of scans over a period of time from 15 minutes to 24 hours
  • it is possible to see a visual result of whether the asphaltenes are settling to the bottom of the tube over time by observing an increase in light transmission in the Turbiscan plots over the length of the tube.
  • By observing the percentage of light transmission for an individual sample it is possible to obtain a separability number for dilutions of 1:3, 1:6, and 1:9 (oil:toluene).
  • the calculated dose rate of the asphaltene dispersant from Sample 1 was added to the selected crude:toluene dilution in a test tube and scans were taken in intervals for 24 hours. The same procedures were carried for benchmark Flowsolve 110 at the same dose rate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Geology (AREA)
  • Mining & Mineral Resources (AREA)
  • General Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Environmental & Geological Engineering (AREA)
  • Fluid Mechanics (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Mechanical Engineering (AREA)
US15/580,904 2015-06-08 2016-06-08 Asphaltene dispersant and methods of use thereof Abandoned US20180312740A1 (en)

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US201562172590P 2015-06-08 2015-06-08
PCT/US2016/036304 WO2016200856A1 (en) 2015-06-08 2016-06-08 Asphaltene dispersant and methods of use thereof
US15/580,904 US20180312740A1 (en) 2015-06-08 2016-06-08 Asphaltene dispersant and methods of use thereof

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WO2018112450A2 (en) * 2016-12-16 2018-06-21 M-I L.L.C. Alkyl cyclic anhydride based emulsifiers for oil based mud
US10655052B2 (en) 2016-12-30 2020-05-19 M-I L.L.C. Method and process to stabilize asphaltenes in petroleum fluids
US11180588B2 (en) 2016-12-30 2021-11-23 Stepan Company Compositions to stabilize asphaltenes in petroleum fluids
US11280779B2 (en) 2017-12-18 2022-03-22 Championx Usa Inc. Solvency for asphaltene deposit remediation or inhibition
GB2617934B (en) * 2019-06-21 2024-06-05 Cameron Tech Ltd Asphaltene dispersants
EP4669717A1 (en) 2023-03-24 2025-12-31 Cameron Technologies Limited HYPER-BRANDED CORROSION INHIBITORS

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US5214224A (en) * 1992-07-09 1993-05-25 Comer David G Dispersing asphaltenes in hydrocarbon refinery streams with α-olefin/maleic anhydride copolymer
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US10626317B2 (en) 2020-04-21
GB2556242B (en) 2021-11-03
MX2017016038A (es) 2018-11-09
US20160355629A1 (en) 2016-12-08
CA2988916A1 (en) 2016-12-15
GB2556242A (en) 2018-05-23
GB201722184D0 (en) 2018-02-14
WO2016200856A1 (en) 2016-12-15

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