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WO2018006495A1 - Procédé de préparation d'un liquide ionique de type carboxylate et utilisation du liquide ionique de type carboxylate - Google Patents

Procédé de préparation d'un liquide ionique de type carboxylate et utilisation du liquide ionique de type carboxylate Download PDF

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Publication number
WO2018006495A1
WO2018006495A1 PCT/CN2016/098966 CN2016098966W WO2018006495A1 WO 2018006495 A1 WO2018006495 A1 WO 2018006495A1 CN 2016098966 W CN2016098966 W CN 2016098966W WO 2018006495 A1 WO2018006495 A1 WO 2018006495A1
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WIPO (PCT)
Prior art keywords
optionally substituted
ionic liquid
carboxylate
lewis base
carboxylic acid
Prior art date
Application number
PCT/CN2016/098966
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English (en)
Chinese (zh)
Inventor
孙大陟
雍怀松
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南方科技大学
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Publication of WO2018006495A1 publication Critical patent/WO2018006495A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/36—Oxalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/60—Maleic acid esters; Fumaric acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C10M133/46—Imidazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property

Definitions

  • the present invention relates to the field of materials technology, and in particular to a method for preparing a carboxylate type ionic liquid and a use of a carboxylate type ionic liquid.
  • Ionic liquids generally consist of organic cations and weakly ionized anions, wherein typical organic cations which can form ionic liquids generally contain N, P or S. Ionic liquids have many important applications, such as for catalysts, plastic additives, dispersants, and lubricant additives.
  • ionic liquids can be used as additive materials, such as lubricating oil additives, to exhibit some excellent performance, there are still some technical problems to be overcome in future applications.
  • the most typical three technical problems are as follows: First, the use of conventional inexpensive halide ionic liquids as additives can cause severe corrosion of some metal materials, such as corrosion of iron or steel; and second, traditional ionic liquid synthesis methods, such as The preparation method of the carboxylate type ionic liquid tends to be difficult to obtain the reaction raw material or the preparation process includes multiple steps, the process is lengthy, the energy consumption is high, and sometimes a large amount of waste is caused. Third, most of the existing ionic liquids are highly polar substances, and most of them are incompatible with non-polar media. These three technical problems limit the application of ionic liquids, especially their use in oily non-polar media.
  • the present invention aims to solve at least one of the technical problems in the related art to some extent. To this end, it is an object of the present invention to provide a process which is simple, economical, easy to implement, or capable of rapidly and efficiently preparing a halide-free carboxylate-type ionic liquid.
  • the invention provides a method of preparing a carboxylate-type ionic liquid.
  • the method comprises: chemically reacting a carboxylic acid ester with a Lewis base in an inert atmosphere and a closed environment, or contacting a carboxylic acid ester with a Lewis base to obtain the carboxylate type ion a liquid, wherein the Lewis base is a tertiary amine type or a tertiary phosphorus type Lewis base, and the temperature of the chemical reaction, or the temperature of the contact, is between the boiling temperature of the carboxylate and the Lewis base. between.
  • the halide-free carboxylate-type ionic liquid can be synthesized in a simple and rapid step, the steps are simple, easy to control, the reaction conditions are mild, and the preparation process is short in time, low in energy consumption, and low in cost.
  • the prepared ionic liquid can be effectively used to disperse carbon deposits in automobile engines.
  • the protective atmosphere is nitrogen or an inert gas that does not react with the reaction substrate.
  • the time of the chemical reaction, or the contact time is from 0.1 to 240 hours.
  • the time of the chemical reaction, or the contact time is 6-72 hours.
  • the parent acid of the carboxylic acid ester has an acidity coefficient pKa of less than 3.
  • the parent acid of the carboxylic acid ester has an acidity coefficient pKa of less than 2.3.
  • the carboxylic acid ester is one selected from the group consisting of:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently an alkyl group, an aryl group or a polyolefin molecular chain having a molecular weight of less than 3,000,
  • X is hydrogen or chlorine
  • y is 0 or 1.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently an alkyl group having 1 to 10 carbon atoms.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently 2-ethyl-1-hexyl, ethyl or methyl.
  • the Lewis base is a small molecule compound or a polymer
  • the small molecule compound is an optionally substituted imidazole, an optionally substituted pyrazoline, an optionally substituted thiazole, an optionally substituted pyridine, an optionally substituted pyrrolidine, an optionally substituted pyridazine, optionally Substituted pyrimidine, optionally substituted quinoline, optionally substituted isoquinoline, optionally substituted piperidine, optionally substituted oxazoline, optionally substituted tertiary amine, optionally substituted tertiary phosphine, optionally a substituted pyrazine, an optionally substituted thiazoline, an optionally substituted imidazoline, an optionally substituted triazoline, an optionally substituted 1,4-diazidebicyclo[2.2.2]octane and derivatives thereof Any of them,
  • the polymer is formed by polymerization of at least one of the following monomers:
  • R 7 is an alkyl group, an aryl group or a polyolefin molecular chain having a molecular weight of less than 3,000.
  • the small molecule compound is selected from one of the following:
  • R 8 , R 9 , R 10 and R 11 are each independently H, an alkyl group, an aryl group, or a polyolefin molecular chain having a molecular weight of less than 3,000.
  • R 8, R 9, R 10 and R 11 are each independently H or an alkyl group having 1-10 carbon atoms.
  • R 8 , R 9 , R 10 and R 11 are each independently H or n-butyl.
  • the molar ratio of the carboxylic acid ester to the Lewis base is (0.5-1.5): (0.5-1.5).
  • the molar ratio of the carboxylic acid ester to the Lewis base is 1:1.
  • the invention provides a carboxylate type ionic liquid.
  • the carboxylate type ionic liquid is prepared by the method described above. The inventors have found that such a carboxylate type ionic liquid can be effectively used to disperse carbon deposits in automobile engines.
  • the present invention provides the use of the carboxylate-type ionic liquid obtained by the above-described method or the carboxylate-type ionic liquid described above for dispersing carbon deposits in automobile engines.
  • the ionic liquid obtained by the method for preparing a carboxylate type ionic liquid of the present invention or the carboxylate type ionic liquid according to the embodiment of the present invention can be used as a dispersing agent for dispersing engine carbon deposits, and the ionic liquid can be effectively used for dispersion. Car engine carbon deposits.
  • Fig. 1 is a graph showing the experimental results of the dispersion stability of an engine ionic liquid and a general commercial detergent dispersant T154A according to an embodiment of the present invention.
  • the invention provides a method of preparing a carboxylate-type ionic liquid.
  • the method comprises: chemically reacting a carboxylic acid ester with a Lewis base in a protective atmosphere and a closed environment, or contacting a carboxylic acid ester with a Lewis base to obtain the carboxylate type ion a liquid, wherein the Lewis base is a tertiary amine type or a tertiary phosphorus type Lewis base, and the temperature of the chemical reaction, or the temperature of the contact is between the boiling temperature of the carboxylate and the Lewis base (standard Measured under atmospheric pressure).
  • the halide-free carboxylate-type ionic liquid can be synthesized in a simple and rapid step, the steps are simple, easy to control, the reaction conditions are mild, and the preparation process is short in time, low in energy consumption, and low in cost.
  • the prepared carboxylate type ionic liquid can be used as a dispersing agent for dispersing engine carbon deposits, and the ionic liquid can be effectively used for dispersing carbon deposits in automobile engines.
  • the carboxylic acid ester with a tertiary amine or tertiary phosphorus Lewis base in a closed vessel.
  • the closed environment can effectively promote the reaction equilibrium to proceed in the forward direction, so that the yield of the ionic liquid can be remarkably improved.
  • the air in the container can be discharged by passing the shielding gas, and then the container is sealed for reaction.
  • the protective atmosphere is not particularly limited, and those skilled in the art can flexibly select according to needs.
  • the protective atmosphere may be nitrogen or an inert gas.
  • inert gas refers to a gas that does not react with a reaction substrate, such as a rare gas, including helium, neon, argon, helium, neon, and the like.
  • the carboxylic acid ester can be reacted or contacted with a Lewis base for 0.1 to 240 hours. In some embodiments of the invention, the carboxylic acid ester can be reacted or contacted with a Lewis base for 6-72 hours. Thereby, it is possible to effectively ensure that the reaction is sufficiently performed without wasting time due to excessive time.
  • the parent acid of the carboxylic acid ester employed in the process has an acidity coefficient of less than 3. That is, the parent acid of pK a of carboxylic acid ester value of less than 3.
  • the coefficient of acidity of the parent acid carboxylic acid ester used in the process is less than 2.3, i.e., the parent acid of pK a of carboxylic acid ester value of less than 2.3.
  • the pK a value of the parent acid of the carboxylic acid ester dominates the reaction, and the pK a value of the parent acid of the carboxylic acid ester is controlled within the above range, and the ionic liquid can be remarkably improved. Yield.
  • the carboxylic acid ester used may be one selected from the group consisting of:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently an alkyl group, an aryl group or a polyolefin molecular chain having a molecular weight of less than 3000, X is hydrogen or chlorine, and y is 0 or 1 .
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently an alkyl group having from 1 to 10 carbon atoms. In still other embodiments of the invention, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently 2-ethyl-1-hexyl, ethyl or methyl. Thereby, the progress of the reaction can be further promoted, and the usability of the obtained ionic liquid can be improved.
  • the Lewis base is a small molecule compound or a polymer, wherein the small molecule compound is an optionally substituted imidazole, an optionally substituted pyrazoline, an optionally substituted thiazole, optionally substituted Pyridine, optionally substituted pyrrolidine, optionally substituted pyridazine, optionally substituted pyrimidine, optionally substituted quinoline, optionally substituted isoquinoline, optionally substituted piperidine, optionally substituted An oxazoline, an optionally substituted tertiary amine, an optionally substituted tertiary phosphine, an optionally substituted pyrazine, an optionally substituted thiazoline, an optionally substituted imidazoline, an optionally substituted triazoline, an optionally substituted 1 Any one of 4-diazidebicyclo[2.2.2]octane and a derivative thereof; the polymer is formed by polymerization of at least one of the following
  • R 7 is an alkyl group, an aryl group or a polyolefin molecular chain having a molecular weight of less than 3,000.
  • the above small molecule compound Lewis base may be one of the following:
  • R 8 , R 9 , R 10 and R 11 are each independently H, an alkyl group, an aryl group, or a polyolefin molecular chain having a molecular weight of less than 3,000.
  • the above Lewis base can be effectively reacted with a carboxylic acid ester to obtain an ionic liquid, and the obtained ionic liquid has better usability.
  • R 8 , R 9 , R 10 and R 11 are each independently H or an alkyl group having from 1 to 10 carbon atoms. In other embodiments of the invention, R 8 , R 9 , R 10 and R 11 are each independently H or n-butyl. Thereby, the usability of the obtained ionic liquid can be further improved.
  • the molar ratio of the carboxylic acid ester to the Lewis base is (0.5-1.5): (0.5-1.5). According to further embodiments of the invention, the molar ratio of the carboxylic acid ester to the Lewis base is 1:1. Within the above ratio range, the carboxylic acid ester and the Lewis base can be sufficiently reacted, which is advantageous for improving the reaction efficiency and yield.
  • the invention provides a carboxylate type ionic liquid.
  • the carboxylate type ionic liquid is prepared by the method described above. The inventors have found that such a carboxylate type ionic liquid can be effectively used to disperse carbon deposits in automobile engines.
  • the present invention provides the use of the carboxylate-type ionic liquid prepared by the method described above for dispersing carbon deposits in automobile engines.
  • the ionic liquid prepared by the method for preparing a carboxylate type ionic liquid of the present invention can be used as a dispersing agent for dispersing engine carbon deposits, and the ionic liquid can be effectively used for dispersing carbon deposits in automobile engines.
  • the reaction product is [1-butyl-3-isooctyl-imidazole][1,2,4-tris(isooctylcarboxylate)-5-benzoate] salt, containing a small amount of 1-butylimidazole and both Tetraisooctyl benzoate.
  • the chemical reaction equation of this example is shown below.
  • the reaction product was a salt of [1-butyl-3-isooctyl-imidazole][1-carboxylic acid isooctyl-2-carboxylate], and the product contained a small amount of 1-butylimidazole and diisooctyl maleate.
  • the chemical reaction equation of this example is shown below.
  • the reaction product was a salt of [1-butyl-3-ethyl-imidazole][1-carboxylate-formate], and the product contained a small amount of 1-butylimidazole and ethyl oxalate.
  • the chemical reaction equation of this example is shown below.
  • the reaction product was a salt of [1-butyl-3-methyl-imidazole][1-formic acid methyl ester-formate], and the product contained a small amount of 1-butylimidazole and dimethyl oxalate.
  • the chemical reaction equation of this example is shown below.
  • test sample preparation process is as follows:
  • Root] salt 0.1 g (0.5% by weight
  • the ionic liquid [1-butyl-3-isooctyl-imidazole][1-carboxylic acid isooctyl ester-2-acrylate] salt prepared in Example 2 0.1 g (0.5% by weight)
  • 250 SN mineral oil was added to the glass bottle C so that the total mass of the mixture was 20 g.
  • FIG. 1 is a schematic diagram of the effect of dispersing the engine carbon deposit of 0.5% by mass into 250 SN mineral oil without adding a detergent dispersant, and after ultrasonic treatment, after standing for one day.
  • FIG. 1 Schematic diagram of the effect of dispersing the carbon deposit of the engine with a mass fraction of 0.5% into 250SN mineral oil, adding the ordinary commercial detergent dispersant T154A with a mass fraction of 0.1%, and after ultrasonic treatment, after standing for seven days.
  • the experimental results shown in FIG. 1 it can be seen that after adding the ionic liquid prepared by the invention for one year, the engine carbon deposit still has very good dispersion stability in the 250 SN mineral oil, and the ionic liquid prepared by the invention can be As a highly efficient dispersant for dispersing engine carbon deposits.
  • first and second are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated.
  • features defining “first” and “second” may include one or more of the features either explicitly or implicitly.
  • the meaning of "a plurality" is two or more unless specifically and specifically defined otherwise.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

L'invention porte également sur un procédé de préparation d'un liquide ionique de type carboxylate et sur une utilisation du liquide ionique de type carboxylate. Le procédé comprend : dans une atmosphère protectrice et un environnement étanche, la soumission d'un ester carboxylique et d'une base de Lewis à une réaction chimique de façon à obtenir le liquide ionique de type carboxylate, la base de Lewis étant une base de Lewis de type amine tertiaire ou de type phosphore tertiaire, et la température de la réaction chimique mentionnée ci-dessus se situe entre les températures de point d'ébullition de l'ester carboxylique et de la base de Lewis.
PCT/CN2016/098966 2016-07-08 2016-09-14 Procédé de préparation d'un liquide ionique de type carboxylate et utilisation du liquide ionique de type carboxylate WO2018006495A1 (fr)

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CN201610538423.8A CN106187900A (zh) 2016-07-08 2016-07-08 制备羧酸盐型离子液体的方法及羧酸盐型离子液体的用途
CN201610538423.8 2016-07-08

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115605564A (zh) * 2020-04-16 2023-01-13 道达尔能量联动技术公司（Fr） 一种基于鏻的离子液体及其作为润滑剂添加剂的用途

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011000490A2 (fr) * 2009-06-30 2011-01-06 Merck Patent Gmbh Synthèse de liquides ioniques
CN102952078A (zh) * 2011-08-26 2013-03-06 中国石油化工股份有限公司 一种烷基咪唑羧酸盐离子液体的制备方法
CN103159632A (zh) * 2013-02-28 2013-06-19 南京大学 一类阴离子含双Lewis碱官能团的离子液体化合物及其制法和用途
US20140099249A1 (en) * 2012-10-10 2014-04-10 Basf Se Ionic liquids based on oxalic acid mono esters
WO2014056844A1 (fr) * 2012-10-10 2014-04-17 Basf Se Liquides ioniques à base de monoesters de l'acide oxalique
CN105254667A (zh) * 2015-11-17 2016-01-20 中国科学院兰州化学物理研究所 功能化油溶性离子液体及其制备方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4529342B2 (ja) * 2002-04-23 2010-08-25 東ソー株式会社 環状アミジニウム有機酸塩の製造方法
JP5214490B2 (ja) * 2008-03-31 2013-06-19 三洋化成工業株式会社 活性エネルギー線硬化型帯電防止性樹脂組成物
EP2589647A1 (fr) * 2011-11-04 2013-05-08 Basf Se Polyétheramines quaternisées et leur utilisation en tant qu'additifs dans des carburants et des lubrifiants

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011000490A2 (fr) * 2009-06-30 2011-01-06 Merck Patent Gmbh Synthèse de liquides ioniques
CN102952078A (zh) * 2011-08-26 2013-03-06 中国石油化工股份有限公司 一种烷基咪唑羧酸盐离子液体的制备方法
US20140099249A1 (en) * 2012-10-10 2014-04-10 Basf Se Ionic liquids based on oxalic acid mono esters
WO2014056844A1 (fr) * 2012-10-10 2014-04-17 Basf Se Liquides ioniques à base de monoesters de l'acide oxalique
CN103159632A (zh) * 2013-02-28 2013-06-19 南京大学 一类阴离子含双Lewis碱官能团的离子液体化合物及其制法和用途
CN105254667A (zh) * 2015-11-17 2016-01-20 中国科学院兰州化学物理研究所 功能化油溶性离子液体及其制备方法和应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115605564A (zh) * 2020-04-16 2023-01-13 道达尔能量联动技术公司（Fr） 一种基于鏻的离子液体及其作为润滑剂添加剂的用途

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