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WO2025015393A1 - Composés inhibiteurs d'incrustations inorganiques et procédé de préparation de ceux-ci - Google Patents

Composés inhibiteurs d'incrustations inorganiques et procédé de préparation de ceux-ci Download PDF

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WO2025015393A1
WO2025015393A1 PCT/BR2024/050098 BR2024050098W WO2025015393A1 WO 2025015393 A1 WO2025015393 A1 WO 2025015393A1 BR 2024050098 W BR2024050098 W BR 2024050098W WO 2025015393 A1 WO2025015393 A1 WO 2025015393A1
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acid
thio
mixture
group
succinic acid
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English (en)
Portuguese (pt)
Inventor
Michelle Jakeline Cunha REZENDE
Brenno Danho Veras EVANGELISTA
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Universidade Federal do Rio de Janeiro UFRJ
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Universidade Federal do Rio de Janeiro UFRJ
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
    • C09K8/528—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning inorganic depositions, e.g. sulfates or carbonates

Definitions

  • the present disclosure is in the field of oilfield chemicals.
  • the present disclosure is also in the field of compounds derived from phosphonic acids.
  • Corrosion inhibitors are natural or synthetic substances capable of preventing the reaction of the metal with the corrosive medium (BELTR ⁇ O et al., 2009; Int. J. Electrochem. Sci., 2013, 8:9317-9331; Arabian Journal for Science and Engineering, 2018, 43:1-22; Journal of Molecular Liquids, 2022, 364:119992).
  • phosphonates are among the most widely used additives as chemical inhibitors (Revista Virtual de Qu ⁇ mica, 2011, 3(1):2- 13; Journal of Water Process Engineering, 2018, 21:1-8).
  • Phosphonates such as aminoalkylphosphonic acid compounds have several applications, such as inhibiting scaling in wells and equipment used in oil and gas production, in the rocks themselves reservoir, in cooling and water treatment systems, in sugar cane processing plants, in pulp and paper processing processes, mining and foliar fertilizer processes, anti-corrosion, aid in offshore oil drilling, detergent additives, chelating agents.
  • scale-forming ions such as calcium ions, barium ions, carbonates, hydrogen carbonates, sulfates, etc., which makes the oil field more susceptible to forming saline scale.
  • inhibitors When applying these inhibitors in oil fields, there is concern about their stability in the face of high temperatures and pressure found in reservoirs. Another growing concern is of an environmental nature and involves the use of toxic substances as inhibitors. Phosphonates can be toxic and cause eutrophication if used in excess. Therefore, it is of great interest and importance to develop more efficient inhibitors, which allow their use in smaller and still effective quantities, or inhibitors with low phosphorus content. Another relevant point is the process of obtaining inhibitors such as aminoalkylphosphonates, since they often involve the use of strong bases or acids as chemical catalysts, and these compounds contribute to environmental pollution.
  • Compounds containing phosphonate groups have been used as corrosion and scale inhibitors in various applications, such as in oil and gas production fields and water and sewage cooling and treatment systems, in sugar cane processing plants, in paper and cellulose processing processes, mining processes and foliar fertilizers, and may be part of the formulation of drilling fluids or varnishes and coating films for vessels, pipelines and other structures exposed to aqueous media containing inorganic foulants or corrosives.
  • Document US10094203B2 discloses corrosion inhibiting fluids prepared from phosphonates and gluconic acid, or their respective salts, said phosphonate being a tertiary amine phosphonate with the general formula X — N — Y2.
  • the document also discloses the method for inhibiting corrosion using combinations of these substances, which are added to drilling brine fluids.
  • the molecules which are aminoalkylphosphonates, are 2-(2-aminoethoxy)ethanol phosphonate and other products already marketed by the applicant.
  • Document CN103708637A discloses inhibitors formed from amino trimethylene phosphonic acid.
  • the synthesis of these amino trimethylene phosphonic N-oxides employs organic acids or alkali metal hydroxides/oxides as catalysts.
  • These scale and corrosion inhibitors are suitable for water systems with the presence of algaecides and chlorine-containing compounds, such as sodium hypochlorite and organic chlorine.
  • Document US20190256762A1 discloses the use of compounds synthesized from the reaction between 4-aminomethyl-1,8-octanediamine (TAN), a commercial product, and phosphorous acid as descaling agents in fluid compositions used in drilling fields.
  • TAN 4-aminomethyl-1,8-octanediamine
  • the described synthesis method is based on the presence of a formylating agent, as well as reaction conditions that convert at least one hydrogen of the TAN amine into a methylphosphonate group.
  • the control of the degree of phosphonation is achieved by the relative concentration of phosphorous acid, formylating agent and TAN used in the reaction mixture.
  • the primary or secondary amines contain at least one phosphoric or phosphonic radical.
  • the compounds present in the descriptive report are 2-aminoethyl phosphonic acid and 2-hydroxyethylamino-N,N-bismethylene phosphonic acid.
  • CN113402548A describes a multifunctional scale inhibitor belonging to the phosphonate class that has high efficiency in oil fields and would be stable for this application, but its synthesis does not start from renewable materials, such as biomass derivatives, and uses toxic compounds.
  • Document CN105600955A discloses 2-phosphono-butane-1,2,4-tricarboxylic acid (PBTCA) as a corrosion and scale inhibitor with a low phosphorus content.
  • the phosphorus content in the molecule is approximately 11.5% of the total mass of PBTCA, well below the 30.1% content found in 1-hydroxyethylene-1,1-diphosphonic acid (HEDP) and 31.1% found in aminotri(methylenephosphonic) acid (ATMP), commonly used inhibitors.
  • HEDP 1-hydroxyethylene-1,1-diphosphonic acid
  • ATMP aminotri(methylenephosphonic) acid
  • the product presented in the present patent application contains 16.2% phosphorus in its protonated form (HBM) or 12.1% in salt form (BM), levels well below those found in the commercial inhibitors HEDP and ATMP.
  • cysteamine hydrochloride with an acid selected from the group comprising maleic acid and fumaric acid, in a cysteamine:maleic acid molar ratio between 0.75:1.25 and 1.25:0.75;
  • aldehyde selected from the group comprising formaldehyde and paraformaldehyde, in a molar ratio of aldehyde:phosphorous acid between 0.75:1.25 and 1.25:0.75;
  • cysteamine hydrochloride and an acid selected from the group comprising maleic acid and fumaric acid, in a cysteamine/maleic acid molar ratio between 0.75:1.25 and 1.25:0.75;
  • the method of preparing the compound 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in its protonated form (HBM) may also comprise the following steps:
  • cysteamine hydrochloride with an acid selected from the group comprising maleic acid and fumaric acid, in a cysteamine/acid molar ratio between 0.75:1.25 and 1.25:0.75;
  • aldehyde selected from the group comprising formaldehyde and paraformaldehyde to the mixture of 2-((2-aminoethyl)thio)succinic acid and phosphorous acid after heating the latter to between 90 and 130 °C, with a molar ratio of aldehyde:phosphorous acid between 0.75:1.25 and 1.25:0.75;
  • the compounds described in this patent application are capable of inhibiting inorganic scaling and corrosion, mainly those caused by carbonates, in activities such as oil and gas production in oil fields.
  • the high efficiency achieved by these compounds allows them to be applied in low concentrations, thus reducing their toxicity and their contribution to the eutrophication of watercourses.
  • the synthesis processes described have a lower potential for environmental pollution, since they are synthetic routes that use green solvents, such as water, less aggressive reagents, of renewable origin, since Maleic acid and fumaric acid can be obtained from biomass.
  • Figure 1 presents the structural formula of the scale and corrosion inhibitor, 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid, in its protonated form (HBM), according to one embodiment of the present description.
  • Figure 2 shows the structural formula of the scale and corrosion inhibitor, 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid, in salt form (BM), where M x is a cation, for example, Na + , K + , Mg 2+ , Ca 2+ , NH 4 + , according to one embodiment of the present disclosure.
  • Figure 3 presents the structural formula of an intermediate product of the synthesis of the scale and corrosion inhibitor, in the form of 2-((2-aminoethyl)thio)succinic acid, according to an embodiment of the present description.
  • Figure 4 presents the structural formula of an intermediate product of the synthesis of the scale and corrosion inhibitor, in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride, according to an embodiment of the present description.
  • Figure 5 is a general schematic of the production process of the scale and corrosion inhibitor compound showing the formation of the intermediate synthesis product, according to an embodiment of the present disclosure.
  • Figure 6 is a general schematic of the production process of the scale and corrosion inhibitor compound, 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid, in its protonated form, according to one embodiment of the present disclosure.
  • Figure 7 is a spectrum obtained by Hydrogen Nuclear Magnetic Resonance ( 1 H NMR) of the intermediate synthesis product, in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride, according to an embodiment of the present description.
  • Figure 8 is a spectrum obtained by Carbon-13 Nuclear Magnetic Resonance ( 13 C NMR) of the intermediate synthesis product, in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride, according to one embodiment of the present description.
  • Figure 9 is a spectrum obtained by Hydrogen Nuclear Magnetic Resonance ( 1 H NMR) of the inhibitor compound in salt form (BM), according to one embodiment of the present disclosure.
  • Figure 10 is a Carbon-13 Nuclear Magnetic Resonance ( 13 C NMR) spectrum of the inhibitor compound in salt form (BM), according to one embodiment of the present disclosure.
  • Figure 11 is a Phosphorus-31 Nuclear Magnetic Resonance ( 31 P NMR) spectrum of the inhibitor compound in salt form (BM), according to one embodiment of the present disclosure.
  • Figure 12 is a spectrum obtained by Hydrogen Nuclear Magnetic Resonance ( 1 H NMR) of the inhibitor compound in protonated form (HBM), according to one embodiment of the present disclosure.
  • Figure 13 is a Carbon-13 Nuclear Magnetic Resonance ( 13 C NMR) spectrum of the inhibitor compound in protonated form (HBM), according to one embodiment of the present disclosure.
  • Figure 14 is a 31 Phosphorus Nuclear Magnetic Resonance ( 31 P NMR) spectrum of the inhibitor compound in protonated form (HBM), according to one embodiment of the present disclosure.
  • Figure 15 is a bar graph showing the percentage of scale inhibition efficiency of the substances HBM and BM, according to an embodiment of the present description, compared to the inhibitory effect of other commercial products of the prior art.
  • the present description discloses inorganic scale and corrosion inhibitor compounds consisting of the molecule 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in the protonated form or in the of a salt of the acid.
  • the scale inhibitor consists of a derivative of maleic acid or its geometric isomer, which is fumaric acid, containing a tertiary amine, a sulfur atom, and one or two phosphonate groups.
  • the scale inhibitor compound is 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in protonated form (HBM).
  • the scale inhibitor compound is 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in unprotonated form, i.e. in the form of a salt, preferably in the form of the sodium salt of 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid (BM).
  • HBM protonated form of the inhibitor compound
  • BM salt form of the inhibitor compound
  • the scale inhibitor compound has a general formula:
  • A is an atom selected from the group comprising O, N and S;
  • R is a radical selected from a group comprising a linear, branched, cyclic or aromatic C2-C10 chain, OR”, NHR”, NR”R” and SR”, where R” is a radical selected from the group comprising H, linear, branched cyclic or aromatic carbon chain, OH, COOH, NH 2 , SH;
  • R’ is a radical selected from the group comprising H, COOH or OH.
  • HBM protonated form
  • the process of producing the inhibitor compound in the non-protonated form (BM) comprises the following steps:
  • aldehyde selected from the group comprising formaldehyde and paraformaldehyde, in a molar ratio of aldehyde:phosphorous acid between 0.75:1.25 and 1.25:0.75;
  • the process of producing the inhibitor compound in protonated form (HBM) comprises following steps:
  • the reagents are solubilized in a solvent selected from the group comprising water and organic solvents, such as ethanol, acetone, methanol, and propanol.
  • Figure 5 shows a general scheme of the production process of the scale and corrosion inhibitor compound, illustrating the formation of 2-((2-aminoethyl)thio)succinic acid hydrochloride as an intermediate synthesis product.
  • the production of the inhibitor compound in protonated form (HBM) excludes the drying and washing step of the intermediate synthesis product called 2-((2-aminoethyl)thio)succinic acid, comprising the following steps:
  • Figure 6 is a general schematic of the production process of the scale and corrosion inhibitor compound in its protonated form (HBM) without the step of removing solvents and washing the intermediate product.
  • HBM protonated form
  • the compound 2-((2-aminoethyl)thio)succinic acid in the form of a salt is obtained from maleic or fumaric acid, by a method comprising the following steps:
  • maleic acid or fumaric acid is mixed with a substance of general formula HS(CH 2 ) n NH x , preferably cysteamine (C 2 H 7 NS), and from the reaction between the two molecules an intermediate product called maleic acid is generated.
  • a substance of general formula HS(CH 2 ) n NH x preferably cysteamine (C 2 H 7 NS)
  • cysteamine C 2 H 7 NS
  • 2-((2-aminoethyl)thio)succinic acid is seen in Figure 3.
  • maleic acid reacts with cysteamine in the form of cysteamine hydrochloride (C 2 H 8 CINS), generating 2-((2-aminoethyl)thio)succinic acid hydrochloride as the intermediate product.
  • cysteamine hydrochloride C 2 H 8 CINS
  • 2-((2-aminoethyl)thio)succinic acid hydrochloride The structural formula of this compound is seen in Figure 4.
  • the step of washing the resulting oil which consists of the compound called 2-((2-aminoethyl)thio)succinic acid in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride, it is washed three times with ethanol and dried in a high vacuum.
  • a solvent selected from the group comprising organic solvents such as ethanol, acetone, methanol and propanol is used.
  • the intermediate compound in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride will be used in the second stage of inhibitor production, in the form of 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid (BM) sodium salt.
  • the intermediate compound in the form of 2-((2-aminoethyl)thio)succinic acid hydrochloride will be used in the second stage of the production of the inhibitor in the protonated form, that is, in the form of 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid (HBM).
  • maleic acid or fumaric acid is obtained from renewable sources.
  • the substance of general formula HS(CH 2 ) n NH x is cysteamine (C 2 H 7 NS), preferably being a cysteamine hydrochloride salt (C 2 H 8 CINS).
  • the reaction between maleic acid and cysteamine occurs in an aqueous or alcoholic reaction medium, the alcohol being a short-chain alcohol, preferably ethanol.
  • the container for carrying out the synthesis process is a sealed container, preferably a glass or borosilicate container.
  • the maleic acid and the cysteamine salt are added to the reaction medium in a molar ratio between 0.75:1.25 and 1.25:0.75, with the equimolar ratio preferably being 1:1.
  • the mixture of maleic acid and cysteamine is stirred at a temperature between 20 and 40 °C for a period of 2 to 4 hours, preferably for a period of 3 hours.
  • phosphorous acid is added to 2-((2-aminoethyl)thio)succinic acid, in an aqueous or alcoholic reaction medium, and the resulting mixture is heated to a temperature between 90 and 130 °C, preferably at a temperature of 105 °C.
  • 2-((2-aminoethyl)thio)succinic acid and phosphorous acid are added in a molar ratio between 0.75:2.75 and 1.25:1.75, with the molar ratio preferably being 1:2.2.
  • formaldehyde or paraformaldehyde is added to the mixture of 2-((2-aminoethyl)thio)succinic acid hydrochloride and phosphorous acid immediately after heating the mixture, with a formaldehyde:phosphorous acid molar ratio between 0.75:1.25 and 1.25:0.75, preferably the equimolar ratio being 1:1, remaining under stirring and heating for a period of 2 to 30 hours, preferably for a period of 2.5 hours.
  • the pH of the reaction medium is adjusted to a value between 8 and 11, preferably pH 9, preferably using a concentrated sodium hydroxide solution; then, this medium is poured into a solvent solution, preferably a solution containing methanol/acetone in a volumetric ratio of 3:1. The addition of solvents will generate a precipitate.
  • the volumetric ratio between the medium reaction medium and the solvent solution is between 0.75:2.5 and 1.25:2.5, preferably with a volumetric ratio of 1:2 of reaction medium/solvent solution.
  • the precipitate is filtered, collected in a round-bottomed flask and dried in high vacuum for an interval between 2 and 4 hours, preferably for 3 hours, to obtain a dry-looking white solid, the structural formula of which can be seen in Figure 2, which corresponds to the inhibitor in the form of 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid salt (BM).
  • BM 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid salt
  • the solution containing the inhibitor compound 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in salt form (BM) or in protonated form (HBM) is used immediately after the synthesis step, without the need for a prior extraction or concentration step.
  • the solution containing the inhibitor compound 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid in salt form or in protonated form undergoes a solvent removal step to obtain the inhibitor in a concentrated form.
  • the solvent removal steps are performed by filtration or evaporation under reduced pressure.
  • the corrosion and incrustation inhibitor compound is used in applications such as oil and gas production fields and water and sewage cooling and treatment systems, in sugar cane processing plants, in paper and cellulose processing processes, mining processes and foliar fertilizers, and may be part of the formulation of drilling fluids or varnishes and coating films for vessels, pipelines and other structures exposed to aqueous media containing incrustants or inorganic corrosives.
  • a first step is performed, and the reaction results in the formation of an intermediate synthesis product.
  • This product after being isolated, is used in a second step, in which the inhibitor is formed.
  • Example 1.3 Second step: production of the inhibitor in the form of protonated 2-((2-(bis(phosphonomethyl)amino)ethyl)thio)succinic acid (HBM):
  • Example 2 The two-step inhibitor synthesis scheme (as per Example 1.1 followed by Example 1.2 or Example 1.3) is seen in Figure 5.
  • Example 2. Direct synthesis of the inhibitor from maleic acid and cysteamine, without intermediate product isolation step:
  • Figure 6 shows the scheme of the direct synthesis of the inhibitor, as per Example 2.
  • Example 1 The samples synthesized in Example 1 (BM and HBM) were evaluated for their effect on inhibiting scale formed by calcium carbonate.
  • the brine was prepared according to the standard test in Standard TM0374-2007, item no. 21208, of the National Association of Corrosion Engineers (NACE).
  • the brine containing calcium had the following composition: 12.15 g L 1 CaCl 2 .2H 2 O; 3.68 g L' 1 MgCl 2 .6H 2 O; 33.0 g L' 1 NaCl; and the composition of the brine containing bicarbonate was: 7.36 g L' 1 NaHCO 3 ; 33.0 g L' 1 NaCl.
  • Table 1 Scale inhibitory effect of HBM and BM substances according to standardized test in Standard TM0374-2007 (NACE).
  • Example 2 The sample synthesized in Example 2 was evaluated for its thermal stability at 4 °C for a period of 30 days and at 130 °C for a period 21 days. The product did not present turbidity, phase change, sludge formation or gelation in relation to the original sample. Table 2 presents the test results, with the captions “S” for positive formation results; “N” for negative formation results and for untested conditions.

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Abstract

La présente invention concerne des composés inhibiteurs d'incrustations inorganiques et de la corrosion, ainsi qu'un procédé de préparation desdits composés inhibiteurs qui sont des amino-alkyl phosphonates pouvant être obtenus sous leur forme chimique protonée ou sous leur forme chimique non protonée.
PCT/BR2024/050098 2023-07-14 2024-03-18 Composés inhibiteurs d'incrustations inorganiques et procédé de préparation de ceux-ci Pending WO2025015393A1 (fr)

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BR102023014170-6A BR102023014170A2 (pt) 2023-07-14 Compostos inibidores de incrustações inorgânicas e método de preparo dos mesmos
BR1020230141706 2023-07-14

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080071112A1 (en) * 2005-01-17 2008-03-20 Thermphos Trading Gmbh Process for the Manufacture of Aminoalkylenephosphonic Acid Compounds in the Presence of a Heterogeneous Catalyst
US20080272341A1 (en) * 2002-06-04 2008-11-06 Lumimove,Inc. Dba Crosslink Polyer Research Corrosion-responsive coating formulations for protection of metal surfaces
US20180346497A1 (en) * 2012-07-17 2018-12-06 Monsanto Technology Llc Method for the synthesis of alpha-aminoalkylenephosphonic acid
WO2022092125A1 (fr) * 2020-10-29 2022-05-05 佐々木化学株式会社 Produit cosmétique pour les cheveux et procédé de production de celui-ci, ainsi que procédé permettant d'améliorer la qualité des cheveux mettant en oeuvre ledit produit cosmétique et procédé permettant de façonner la coiffure
WO2023003943A1 (fr) * 2021-07-22 2023-01-26 Lfs Chemistry Incorporated Inhibiteurs de tartre et particules à libération contrôlée associées

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080272341A1 (en) * 2002-06-04 2008-11-06 Lumimove,Inc. Dba Crosslink Polyer Research Corrosion-responsive coating formulations for protection of metal surfaces
US20080071112A1 (en) * 2005-01-17 2008-03-20 Thermphos Trading Gmbh Process for the Manufacture of Aminoalkylenephosphonic Acid Compounds in the Presence of a Heterogeneous Catalyst
US20180346497A1 (en) * 2012-07-17 2018-12-06 Monsanto Technology Llc Method for the synthesis of alpha-aminoalkylenephosphonic acid
WO2022092125A1 (fr) * 2020-10-29 2022-05-05 佐々木化学株式会社 Produit cosmétique pour les cheveux et procédé de production de celui-ci, ainsi que procédé permettant d'améliorer la qualité des cheveux mettant en oeuvre ledit produit cosmétique et procédé permettant de façonner la coiffure
WO2023003943A1 (fr) * 2021-07-22 2023-01-26 Lfs Chemistry Incorporated Inhibiteurs de tartre et particules à libération contrôlée associées

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