WO2021226845A1 - Agent chélatant, agent de nettoyage et procédé de préparation d'un agent chélatant - Google Patents

Agent chélatant, agent de nettoyage et procédé de préparation d'un agent chélatant Download PDF

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WO2021226845A1
WO2021226845A1 PCT/CN2020/089864 CN2020089864W WO2021226845A1 WO 2021226845 A1 WO2021226845 A1 WO 2021226845A1 CN 2020089864 W CN2020089864 W CN 2020089864W WO 2021226845 A1 WO2021226845 A1 WO 2021226845A1
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salt
acid
compound
chelating agent
temperature
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PCT/CN2020/089864
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English (en)
Chinese (zh)
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欧敏
梅龙毅
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南京艾普拉斯化工有限公司
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Priority to PCT/CN2020/089864 priority Critical patent/WO2021226845A1/fr
Publication of WO2021226845A1 publication Critical patent/WO2021226845A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen

Definitions

  • This application relates to the technical field of organic chemistry synthesis, in particular to the preparation methods of chelating agents, cleaning agents and chelating agents.
  • common chelating agents mainly include phosphate, hydroxycarboxylic acid, aminocarboxylic acid, and carboxylic acid-containing polymers.
  • Phosphate has a better chelating effect, but the phosphorus content causes great pollution to the environment.
  • Sodium tripolyphosphate (STPP) is mainly used more frequently, but it has gradually faded out of the market in the global call for phosphorus restriction and prohibition.
  • Hydroxy carboxylic acids mainly include sodium gluconate, sodium citrate, etc.
  • the chelating performance of metal ions is poor and the cost performance is not high.
  • Acrylic polymer is a polymer chelating agent. In addition to its chelating ability, it also has thickening and flocculation effects.
  • Aminocarboxylic acids mainly include ethylenediaminetetraacetic acid (EDTA), Hydroxyethylethylenediaminetriacetic acid (HEDTA), Diethylenetriaminepentaacetic acid (DTPA), Nitrotriacetic acid (NTA), Iminodisuccinic acid (IDS), Glutamate diacetic acid (GLDA) ), methylglycine diacetic acid (MGDA) and so on.
  • EDTA ethylenediaminetetraacetic acid
  • HEDTA Hydroxyethylethylenediaminetriacetic acid
  • DTPA Diethylenetriaminepentaacetic acid
  • NDA Nitrotriacetic acid
  • GLDA Glutamate diacetic acid
  • MGDA methylglycine diacetic acid
  • EDTA is not easily biodegradable (OECD)
  • NTA has potential carcinogenicity
  • IDS has low performance in chelating metals
  • GLDA and MGDA have high raw material toxicity, high equipment requirements, industrialization difficulties, high production costs, and product prices. It is expensive and often limits its widespread use in real life.
  • This application provides a chelating agent, a cleaning agent, and a preparation method of a chelating agent, which can provide a chelating agent with no phosphorus and strong chelating performance.
  • this application provides a chelating agent, the general formula of the chelating agent is as follows:
  • R 1 , R 2 , R 3 and R 4 are alkyl groups
  • M 1 , M 2 , M 3 and M 4 are hydrogen atoms, metal atoms, ammonium groups or organic amine groups;
  • A is a hydroxyl group or an amino group.
  • the alkyl group is -(CH 2 ) n -, and 0 ⁇ n ⁇ 6.
  • R 1 and R 4 are -(CH 2 ) 0 -, and R 2 and R 3 are -CH 2 -.
  • the metal atom is Na.
  • this application provides a method for preparing the above chelating agent, the method comprising:
  • R is R 2 or R 3 as defined in claim 1
  • M is M 2 or M 3 as defined in claim 1
  • M 1 and M 2 have the same meaning as in claim 1
  • L is a leaving group group.
  • this application provides another method for preparing the above chelating agent, which method includes:
  • compound D is R 2 and R 3 have the same meanings as in claim 1, and M 5 and M 6 are hydrogen atoms, metal atoms, ammonium groups, or organic amine groups.
  • the addition reaction of epoxysuccinic acid (salt) and compound D to obtain the chelating agent includes:
  • the second temperature is 60-100°C; the fourth time is 0.5-2h; the fifth time is 2-24h.
  • said providing epoxysuccinic acid (salt) includes: providing maleic acid (salt) and/or fumaric acid (salt), and cyclizing maleic acid (salt) and/or fumaric acid (salt) Oxidation reaction to obtain epoxysuccinic acid (salt).
  • the epoxidation reaction of maleic acid (salt) and/or fumaric acid (salt) to obtain epoxysuccinic acid (salt) includes: making maleic acid (salt) and/or fumaric acid (salt) Acid (salt) undergoes epoxidation reaction under oxidant, catalyst and weakly alkaline or weakly acidic environment;
  • the catalyst is at least one of sodium tungstate, sodium molybdate, and ammonium vanadate;
  • the weakly alkaline or weakly acidic environment refers to an environment with a pH of 3-8.
  • the epoxidation reaction of maleic acid (salt) and/or fumaric acid (salt) in an oxidant, a catalyst and a weakly alkaline or weakly acidic environment includes:
  • the oxidant solution is added dropwise to maleic acid (salt) and/or fumaric acid (salt), while adjusting the maleic acid (salt) and/or fumaric acid (salt) by adding lye PH of the solution;
  • maleic acid (salt) and/or fumaric acid (salt) includes:
  • the maleic anhydride undergoes a hydrolysis reaction at the hydrolysis temperature to obtain maleic acid (salt) and/or fumaric acid (salt);
  • maleic acid (salt) and/or fumaric acid (salt) then includes:
  • the first time is 30-60min; the second time is 40-120min; the third time is 2-10h; the first temperature is 45-80°C; the third temperature is 40-60°C; The hydrolysis temperature is 0-75°C; the first pH is 4-8.
  • this application provides a method for preparing the above chelating agent, the method comprising:
  • compound C is L is a leaving group
  • R is R 2 or R 3 as defined in claim 1
  • M is M 2 or M 3 as defined in claim 1.
  • this application provides a method for preparing the above chelating agent, the method comprising:
  • L is a leaving group, and R is R 2 or R 3 as defined in claim 1.
  • the present application provides a cleaning agent, which includes the above-mentioned chelating agent.
  • the chelating agent disclosed in the present application has high chelating performance to calcium, magnesium and copper, and the chelating agent disclosed in the present application also has good chelating performance to iron ions.
  • the chelating agent disclosed in the application shows particularly good chelating properties for calcium, magnesium, iron, copper or other metals, and has a strong chelating ability.
  • this application is non-toxic and non-phosphorus, biodegradable, and can replace traditional chelating agents such as EDTA, DPTA, NTA, which are difficult to biodegrade or expensive.
  • it in addition to high solubility in high-concentration aqueous alkali and acid solutions, it also has excellent storage stability.
  • Figure 1 is a schematic diagram of a mass spectrum of an embodiment of the chelating agent of the present application.
  • Fig. 2 is a schematic diagram of the hydrogen nuclear magnetic spectrum of an embodiment of the chelating agent of the present application.
  • this application provides an embodiment of the chelating agent of Formula I:
  • R 1 , R 2 , R 3 and R 4 are alkyl groups.
  • M 1 , M 2 , M 3 and M 4 are hydrogen atoms, metal atoms, ammonium groups or organic amine groups.
  • A is a hydroxyl group or an amino group.
  • the chelating agent provided in this application can be synthesized by any kind of raw materials and methods by those skilled in the art according to its general structural formula.
  • R 1, R 2 , R 3 and R 4 are preferably -(CH 2 ) n -, 0 ⁇ n ⁇ 6, that is, n can be equal to 1, 2, 3, 4, 5 or 6. .
  • R 1 and R 4 are the same, and at least one of R 2 and R 3 is different from R 1.
  • R 1 and R 4 are -(CH 2 ) 0 -, and R 2 and R 3 are -CH 2 -.
  • the metal atom may be an alkali metal atom, a transition metal atom, a heavy metal atom, or a rare earth metal atom.
  • M 1 , M 2 , M 3 and M 4 are preferably H and alkali metal cations. More preferably, M 1 , M 2 , M 3 and M 4 are H and Na. In addition, M 1 , M 2 , M 3 and M 4 may be different from each other. Alternatively, M 1 , M 2 , M 3 and M 4 are all the same. Alternatively, M 1 and M 4 are the same, and at least one of M 2 and M 3 is different from M 1 .
  • the chelating agent of the present application is preferably Formula Ia, Formula Ib and Formula Ic.
  • the chelating agent represented by formula I can form a coordination geometric structure with the metal cation.
  • the coordination geometric structure formed by the chelating agent and iron ions is as follows:
  • This application takes the chelating agents represented by formulas Ia and Ib as representatives, and analyzes the chelating ability of the chelating agents disclosed in this application.
  • the chelating performance of the chelating agent disclosed in this application on calcium, magnesium, and copper has greatly exceeded that of EDTA and other similar biodegradable chelating agents, and the chelating agent disclosed in this application has a chelating effect on iron ions.
  • the chelating performance is also very good, that is, the chelating agent disclosed in the present application shows particularly good chelating performance for calcium, magnesium, iron, copper or other metals, and has a strong chelating ability.
  • the chelating agent disclosed in the present application has higher dispersibility, and may be more effective when used in conjunction with other chelating dispersing agents.
  • the chelating agent disclosed in the present application can be used as a cleaning agent, and the cleaning agent may include a household detergent, an industrial cleaning agent, a water softener, and an extractant of heavy metal contaminants.
  • the cleaning agent is widely used in printing and dyeing auxiliaries, dyeing and finishing processes, textile industry, paper industry, photosensitive materials, ceramic industry, electroplating industry and other industries.
  • the chelating agent disclosed in the present application can also be used as a scale inhibitor and dispersant in the field of traditional industrial circulating water.
  • the non-toxic, non-phosphorus, biodegradable, and expensive traditional chelating agents such as EDTA, DPTA, NTA, etc., disclosed in this application.
  • the chelating agent disclosed in the present application is a colorless or light yellow transparent liquid at room temperature. It is not easy to crystallize at -25°C and below for a long time. It has high solubility in both high-concentration aqueous alkali and acid solutions. It has excellent storage stability.
  • the present application provides a method for preparing the above-mentioned chelating agent according to the first embodiment.
  • the method for preparing a chelating agent in this embodiment includes the following steps.
  • Step 11 Provide epoxysuccinic acid (salt).
  • epoxysuccinic acid refers to epoxysuccinic acid and/or epoxysuccinate (including a form in which two carboxyl groups are a salt and a form in which only one carboxyl group is a salt).
  • epoxysuccinic acid (salt) can be self-made or commercially available.
  • epoxysuccinic acid (salt) may be cis-epoxysuccinic acid (salt) and/or trans-epoxysuccinic acid (salt).
  • cis-epoxysuccinic acid can be prepared by subjecting maleic acid (salt) to epoxidation reaction.
  • maleic acid (salt) refers to maleic acid and/or maleic acid salt (including two carboxyl groups as a salt form and only one carboxyl group as a salt form).
  • the maleic acid (salt) is subjected to the epoxidation reaction in an oxidizing agent and a catalyst, and a weakly acidic or weakly basic environment.
  • the oxidant may be hydrogen peroxide, but of course it is not limited to this.
  • sodium hypochlorite may also be used as the oxidant.
  • the oxidant solution added to the maleic acid (salt) can be a hydrogen peroxide solution with a mass fraction of 25%-40%.
  • the catalyst may include at least one of sodium tungstate, sodium molybdate, or sodium vanadate, but of course it is not limited thereto.
  • the molar ratio of maleic acid (salt) to the catalyst is greater than or equal to 1:0.005.
  • the molar ratio of maleic acid (salt) to catalyst is 1:0.015-1:0.4.
  • a weakly acidic or weakly alkaline environment refers to an environment with a pH of 3-8.
  • the weakly acidic or weakly alkaline environment refers to an environment with a pH of 6.0-7.5.
  • the weakly alkaline environment can be provided by LiOH, NaOH or KOH.
  • the weakly alkaline environment for the maleic acid (salt) reaction can be constructed by adding lye to the maleic acid (salt).
  • the lye is a solution of LiOH, NaOH and/or KOH with a mass fraction of 25%-60%.
  • the temperature environment for the epoxidation reaction of maleic acid (salt) may not be higher than 100°C.
  • the temperature environment for the epoxidation reaction of maleic acid (salt) may not be higher than 75°C.
  • the temperature environment for the epoxidation reaction of maleic acid (salt) may be 60-70°C.
  • the catalyst can be added to the maleic acid (salt) first, and stirred for the first time, and then the oxidant solution is added dropwise to the maleic acid (salt) during the second time, while adjusting the maleic acid (salt) by adding lye.
  • the pH of the acid (salt) solution After the addition of hydrogen peroxide is completed, the temperature is raised to the first temperature, and the mixture is stirred for the third time. It can be understood that the second time is the time taken to add the oxidant solvent dropwise to the maleic acid (salt).
  • the first time is 30-60 minutes.
  • the first time is 40-50 min. More preferably, the first time is 45 minutes.
  • the second time is 40-120 min. Preferably, the second time is 60-90 min.
  • the first temperature is 45-80°C.
  • the first temperature is 60-65°C.
  • the third time is 2-10h. Preferably, the third time is 3h.
  • maleic acid (salt) can be self-made or commercially available.
  • the present application can obtain maleic acid (salt) through the hydrolysis of maleic anhydride.
  • the pH of the maleic anhydride solution can be adjusted to a suitable range to accelerate the hydrolysis rate of maleic anhydride.
  • the pH of the maleic anhydride solution can be adjusted by NaOH, KOH, or LiOH.
  • the hydrolysis rate can also be adjusted by adjusting the hydrolysis temperature of maleic anhydride.
  • the hydrolysis temperature of maleic anhydride is 0-75°C, such as 20°C, 25°C, or 30°C.
  • the pH and temperature of the solution of the hydrolysate can also be adjusted to enable faster epoxidation.
  • the third temperature of the solution of the hydrolysate is adjusted to 40-60°C
  • the first pH of the solution of the hydrolysate is adjusted to 4-8.
  • trans-epoxysuccinic acid (salt) can be prepared by subjecting fumaric acid (salt) to epoxidation reaction.
  • maleic acid (salt) refers to maleic acid and/or maleic acid salt (including two carboxyl groups as a salt form and only one carboxyl group as a salt form).
  • the process of preparing trans-epoxysuccinic acid (salt) with fumaric acid (salt) can refer to the process of preparing cis-epoxysuccinic acid (salt) with maleic acid (salt), which will not be repeated here.
  • Step 12 Addition reaction of epoxysuccinic acid (salt) and compound A to obtain compound B.
  • M is M 2 and M 3 as defined in the first aspect
  • R is R 2 and R 3 as defined in the first aspect
  • M 1 and M 2 are as defined for formula I in the first aspect.
  • R in compound A is -CH 2 -, that is, compound A is aminoacetic acid.
  • Step 13 Substituting compound B and compound C to obtain the chelating agent represented by formula (I).
  • L is a leaving group.
  • L is Cl, I, or Br, etc., of course, it is not limited thereto.
  • M is the same as M 2 and M 3 defined in the first aspect.
  • M is Na or H.
  • R is as defined in the first aspect as R 2 and R 3 .
  • R is -CH 2 -.
  • compound C is chloroacetic acid.
  • the chelate compound represented by formula Ia of the first aspect can be obtained by reacting the addition product of aminoacetic acid and epoxysuccinic acid with chloroacetic acid.
  • this application provides a second method for preparing the above-mentioned chelating agent.
  • the method for preparing a chelating agent in this embodiment includes the following steps.
  • Step 21 Provide epoxysuccinic acid (salt) and compound D.
  • R 2 and R 3 are as defined for formula I in the first aspect.
  • M 5 and M 6 are hydrogen atoms, metal atoms, ammonium groups, or organic amine groups.
  • M 5 and M 6 are hydrogen atoms, and R 2 and R 3 are -CH 2 -, that is, compound D is iminodiacetic acid.
  • Step 22 Perform an addition reaction between epoxysuccinic acid (salt) and compound D to obtain the chelating agent.
  • epoxysuccinic acid (salt) and compound D can be mixed first, and then stirred for the fourth time, and then the hydroxide containing M 7 is added, the temperature is raised to the second temperature, and the reaction is performed for the fifth time to obtain the formula I
  • M 7 is the same as M 1 and M 4 defined in the first aspect.
  • the fourth time is 0.5-2h. Preferably, the fourth time is 1-1.5h.
  • the second temperature is 60-100°C. Preferably, the second temperature is 80-95°C.
  • the fifth time is 2-24h. Preferably, the fifth time is 3-15h.
  • the molar ratio of epoxysuccinic acid (salt), compound D and M 7 atoms is about 1:1:1 to 1:5.
  • the molar ratio of epoxysuccinic acid (salt), compound D and M 7 atoms is about 1:1:1.5-1:1:2.
  • compound D is iminodiacetic acid, so that the compound represented by formula Ia of the first aspect can be obtained by reacting epoxysuccinic acid (salt) with compound D.
  • the present application provides a method for preparing the above-mentioned chelating agent according to the third embodiment.
  • the method for preparing a chelating agent in this embodiment includes the following steps.
  • Step 31 Provide 3-hydroxyaspartic acid and compound C.
  • L is a leaving group.
  • L is Cl, I, or Br, etc., of course, it is not limited thereto.
  • M is the same as M 2 and M 3 defined in the first aspect.
  • M is Na or H.
  • R is the same as R 2 and R 3 defined in the first aspect.
  • R is -CH 2 -.
  • compound C is chloroacetic acid, iodoacetic acid, bromoacetic acid, or the like.
  • Step 32 Substituting 3-hydroxyaspartic acid and compound C to obtain the chelating agent represented by formula I.
  • 3-hydroxyaspartic acid and compound C can undergo a substitution reaction in an alkaline environment.
  • the alkaline environment can be provided by many alkaline substances.
  • the alkaline environment includes NaOH or KOH.
  • the chelating agent represented by formula Ia can be produced by the substitution reaction of 3-hydroxyaspartic acid and compound C.
  • this application provides a method for preparing the chelating agent represented by Formula I according to the fourth embodiment.
  • the method for preparing the chelating agent represented by Formula I in this embodiment includes the following steps.
  • Step 41 Provide 3-hydroxyaspartic acid and compound E.
  • R is as defined in the first aspect as R 2 and R 3 .
  • R is -CH 2 -.
  • L is a leaving group.
  • L is Cl, I, or Br, etc., of course, it is not limited thereto.
  • the compound E is chloroacetonitrile, iodoacetonitrile, bromoacetonitrile or the like.
  • Step 42 Substituting 3-hydroxyaspartic acid and compound E to obtain compound F.
  • this application can make 3-hydroxyaspartic acid and compound E undergo a substitution reaction under the action of the second catalyst.
  • the second catalyst is inorganic ammonium salt, organic amine or amide, etc.
  • the second catalyst is triethylamine.
  • Step 43 Make compound F undergo a hydrolysis reaction to obtain a chelating agent represented by formula I.
  • compound F By hydrolyzing the cyano group of compound F to produce carboxylic acid or carboxylate, compound F is converted into a chelating agent represented by formula I.
  • the compound F may undergo a hydrolysis reaction in an acidic environment or an alkaline environment.
  • the acid-base requirement for the hydrolysis reaction of compound F can be: the pH of the reaction solution of compound F is less than or equal to 3, or greater than or equal to 10.
  • Various bases can provide an alkaline environment, as long as the pH of the compound F reaction solution meets the above-mentioned acid-base requirements by adding a base.
  • NaOH provides an alkaline environment.
  • various acids can provide an acidic environment, as long as the pH of the compound F reaction solution meets the above-mentioned acid-base requirements by adding an acid.
  • the acidic environment is provided by hydrochloric acid.
  • the above method for preparing the chelating agent represented by formula I has a wide range of raw materials, low price, simple production equipment, chemical reactions in the reaction process can be synthesized in a one-pot method, high safety, no highly toxic substances involved, and product collection High rate, good performance and no negative impact on the environment. It is a green and environmentally friendly process that is easy for large-scale industrial production.
  • the chelating agent shown in Formula Ib can be obtained.
  • the mass spectrum of the obtained product is shown in Figure 1, the measured value is 266.1, and the measured value is consistent with the theoretical value of the chelating agent shown in formula Ib, which proves that the obtained product includes the chelating agent shown in formula Ib.
  • the purity of the chelating agent represented by formula Ib in the obtained product is greater than or equal to 99%.
  • this application uses the following test methods to determine the chelating performance of the chelating agent to various metal ions.
  • V 0 -Blank solution consumes 0.25mol/L MgCl 2 standard solution volume, ml;
  • the number of milligrams of complexed copper ions per gram of copolymer is the number of milligrams consumed during the titration of the standard solution.
  • V 1 The volume of the trivalent iron standard solution consumed by the sample solution (ml);
  • V 0 The volume of the trivalent iron standard solution consumed by the blank solution (ml);

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Abstract

La présente invention concerne un agent chélatant, un agent de nettoyage et un procédé de préparation de l'agent chélatant. L'agent chélatant a une formule générale développée telle que représentée par la formule (I), dans laquelle : R1, R2, R3 et R4 représentent des groupes alkyle ; M1, M2, M3 et M4 représentent des atomes d'hydrogène, des atomes métalliques, des groupes ammonium ou des groupes amine organiques ; A représente un groupe hydroxyle ou un groupe amino. L'agent chélatant fourni par la présente invention peut être exempt de phosphore et a une forte propriété de chélation.
PCT/CN2020/089864 2020-05-12 2020-05-12 Agent chélatant, agent de nettoyage et procédé de préparation d'un agent chélatant WO2021226845A1 (fr)

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