CN112552326B - Silole derivative, preparation method and application thereof, and photoluminescent lubricating grease - Google Patents

Silole derivative, preparation method and application thereof, and photoluminescent lubricating grease Download PDF

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CN112552326B
CN112552326B CN201910910017.3A CN201910910017A CN112552326B CN 112552326 B CN112552326 B CN 112552326B CN 201910910017 A CN201910910017 A CN 201910910017A CN 112552326 B CN112552326 B CN 112552326B
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grease
group
formula
base oil
silole derivative
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CN112552326A (en
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刘欣阳
何懿峰
郑会
刘伟
李朝宇
陈靖
刘中其
庄敏阳
姜靓
孙洪伟
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/06—Mixtures of thickeners and additives
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
    • C10M2207/1265—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic used as thickening agent
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
    • C10M2207/1285—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof used as thickening agents
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
    • C10M2207/1415—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic used as thickening agent
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/045—Polyureas; Polyurethanes
    • C10M2217/0456—Polyureas; Polyurethanes used as thickening agents
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract

The invention provides a silole derivative, a preparation method and application thereof, and photoluminescent lubricating grease containing the silole derivative. The silole derivative has a structure shown in a formula (I):

Description

Silole derivative, preparation method and application thereof, and photoluminescent lubricating grease
Technical Field
The invention relates to a silole derivative, in particular to a silole derivative with a light-emitting property.
Background
Traditional organic chromophores generally have strong luminescence at low concentrations, and weak or even no luminescence at high concentrations or in solid states, exhibiting an aggregate fluorescence quenching effect. This is because in the aggregate state, the strong intermolecular interactions lead to an enhancement of the non-radiative decay process of the excited state, with a significant decrease in fluorescence quantum yield. In the practical application process, the practical application of the organic light-emitting material is limited to a great extent by the aggregate fluorescence quenching effect. In recent years, research shows that some compounds show the opposite properties to the traditional organic luminescent compounds, not only do not have aggregation fluorescence quenching effect, but also show Aggregation Induced Emission (AIE) properties, and the appearance of the aggregation induced emission compounds provides a new solution for the application of organic luminescent materials in a solid state or at high concentration.
The lubricating grease is a solid to semi-fluid product prepared by dispersing a thickening agent in a liquid lubricant, has the functions of lubrication, protection and sealing, and plays a vital role in industrial machinery, agricultural machinery, the transportation industry, the aerospace industry, the electronic information industry and various military equipment. Under some dark working conditions, the monitoring of the lubricating grease has great difficulty. At present, the related report of the luminescent grease is rarely seen.
Disclosure of Invention
The invention provides a silole derivative, a preparation method and application thereof, and photoluminescent grease containing the silole derivative, which are described in the specification.
In a first aspect, the present invention provides a silole derivative.
The silole derivative has a structure shown in a formula (I):
Figure BDA0002214432450000011
wherein each R is 0 Are the same or different from each other and are each independently selected from hydrogen and C 1-6 Straight or branched chain hydrocarbon radicals (preferably hydrogen, C) 1-4 Straight or branched chain alkyl), each x is independently selected from an integer between 0 and 5 (preferably 0, 1,2, 3); the L' group is selected from
Figure BDA0002214432450000021
C 1-6 Straight or branched chain hydrocarbon radicals (preferred is device for selecting or keeping>
Figure BDA0002214432450000022
C 1-4 Straight or branched alkyl), wherein R is 0 Selected from hydrogen, C 1-6 Straight or branched chain hydrocarbon radicals (preferably hydrogen, C) 1-4 Linear or branched alkyl), x is selected from integers between 0 and 5 (preferably 0, 1,2, 3);
n is an integer of 1 to 10 (preferably an integer of 1 to 5); n A groups, equal to or different from each other, are each independently selected from the group represented by formula (II), H and C 1-6 Straight-chain or branched hydrocarbon groups (preferably a group of the formula (II), H and C 1-4 Straight or branched chain alkyl) and at least one A group is selected from the group represented by formula (II);
Figure BDA0002214432450000023
in formula (II), each R group is independently selected from C 1-20 Straight or branched chain alkylene (preferably selected from C) 1-10 Linear or branched alkylene); each R' group is independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); the R' group is selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); each R' "group is independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); y is an integer of 0 to 4 (preferably 0 or 1);
cyclic group
Figure BDA0002214432450000024
Selected from benzene rings and naphthalene rings (preferably selected from benzene rings);
the L group being a single bond or an (n + 1) -valent C 1-30 Hydrocarbyl (preferably a single bond or (n + 1) -valent C 1-6 Straight or branched chain alkyl).
According to the present invention, the silole derivative may have the following structure:
Figure BDA0002214432450000031
in a second aspect, the present invention provides a method for preparing silole derivatives.
The method for producing a silole derivative of the present invention comprises the step of reacting a silole compound represented by the formula (III) with a compound represented by the formula (IV),
Figure BDA0002214432450000032
in the formula (III), each R 0 Are the same or different from each other and are each independently selected from hydrogen and C 1-6 Straight or branched chain hydrocarbon radicals (preferably hydrogen, C) 1-4 Straight or branched chain alkyl), each x is independently selected from an integer between 0 and 5 (preferably 0, 1,2, 3); the L' group is selected from
Figure BDA0002214432450000033
C 1-6 Straight or branched chain hydrocarbon radicals (preferred is device for selecting or keeping>
Figure BDA0002214432450000034
C 1-4 Straight or branched alkyl), wherein R is 0 Selected from hydrogen, C 1-6 Straight or branched chain hydrocarbon radicals (preferably hydrogen, C) 1-4 Linear or branched alkyl), x is selected from integers between 0 and 5 (preferably 0, 1,2, 3); in formula (IV), the X group is F, cl, br, I or OH (preferably Cl, br); n is an integer of 1 to 10 (preferably an integer of 1 to 5); n A's are each independently selected from the group consisting of a group represented by the formula (V), C 1-10 Straight or branched chainAlkyl and H (preferably selected from the group consisting of a group represented by formula (V), C 1-6 Straight or branched chain alkyl and H), and at least one A group is selected from the group represented by formula (V),
Figure BDA0002214432450000035
in formula (V), each R group is independently selected from C 1-20 Straight or branched chain alkylene (preferably selected from C) 1-10 Linear or branched alkylene); each R' group is independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); r' group is selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); each R' "group is independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-10 Straight or branched chain alkyl); y is an integer of 0 to 4 (preferably 0 or 1);
cyclic group
Figure BDA0002214432450000041
Selected from the group consisting of benzene rings and naphthalene rings (preferably selected from benzene rings);
the group L is a single bond or (n + 1) -valent C 1-30 A hydrocarbon group (preferably a single bond or (n + 1) -valent C 1-6 Straight or branched chain alkyl).
According to the preparation method of the present invention, the silole compound represented by formula (III) may be selected from one or more of the following compounds:
Figure BDA0002214432450000042
according to the preparation method of the present invention, the compound represented by the formula (IV) may be selected from one or more of the following compounds:
Figure BDA0002214432450000043
according to the production method of the present invention, in the reaction, the molar ratio between the silole compound represented by the formula (III) and the compound represented by the formula (IV) is preferably 1:0.5 to 5, most preferably 1:0.8 to 1.2.
According to the preparation method of the present invention, preferably, the temperature of the reaction is 0 to 50 ℃, preferably 15 to 35 ℃.
According to the preparation method of the invention, the reaction time is preferably 6 to 96 hours, preferably 12 to 72 hours.
According to the invention, a catalyst is preferably added to the reaction. The catalyst is preferably one or more of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, more preferably a mixture of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, the molar ratio of the three preferably being 1:0.1 to 10:0.1 to 10, more preferably 1:0.2 to 5:0.2 to 5.
According to the present invention, preferably, the metal phosphine complex has the structure
Figure BDA0002214432450000051
Wherein M is Pd, ru or Rh, L is selected from PPh 3 Ph, F, cl, br, I. The metal phosphine complex can be one or more of tetrakis (triphenylphosphine) palladium, tris (triphenylphosphine) palladium chloride, bis (triphenylphosphine) palladium dichloride, (triphenylphosphine) palladium trichloride, tetrakis (triphenylphosphine) ruthenium, tris (triphenylphosphine) ruthenium chloride, bis (triphenylphosphine) ruthenium dichloride, (triphenylphosphine) ruthenium trichloride, tetrakis (triphenylphosphine) rhodium, tris (triphenylphosphine) rhodium chloride, bis (triphenylphosphine) rhodium dichloride and (triphenylphosphine) rhodium trichloride, preferably one or more of tetrakis (triphenylphosphine) palladium, tris (triphenylphosphine) palladium chloride, bis (triphenylphosphine) palladium dichloride and (triphenylphosphine) palladium trichloride.
According to the present invention, preferably, the metal halide may be one or more of copper halide, iron halide and zinc halide, for example, one or more of copper chloride, cuprous chloride, copper bromide, cuprous bromide, copper iodide, cuprous iodide, ferric chloride, ferrous chloride, ferric bromide, ferrous bromide, ferric iodide, ferrous iodide, zinc chloride, zinc chlorite, zinc bromide, zinc iodide and zinc iodide may be used, and more preferably one or more of copper chloride, cuprous chloride, copper bromide, cuprous bromide, copper iodide and cuprous iodide.
According to the present invention, preferably, the hydrocarbyl phosphine compound has the structure
Figure BDA0002214432450000052
Wherein each R is independently selected from C 6 ～C 10 Aryl and C 1 ～C 6 Wherein at least one R is C 6 ～C 10 Aryl group of (1). Said C is 6 ～C 10 The aryl group of (a) may be selected from phenyl, naphthyl; said C is 1 ～C 6 The linear or branched alkyl group of (b) may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl or isohexyl. The hydrocarbyl phosphine compound can be selected from triphenylphosphine and diphenylbutylphosphine.
According to the invention, the amount of the catalyst added is preferably 1% to 20% of the amount of the silole compound of formula (II).
According to the production method of the present invention, preferably, a solvent is added in the reaction. The solvent is preferably C 1 ～C 10 Examples of the organic amine and furan include methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine and tetrahydrofuran, and most preferably C 1 ～C 10 The volume ratio of the organic amine to the furan is preferably 1:0.1 to 10. The solvent may be removed by a method known in the art after the completion of the reaction, and the removal method is not particularly limited, and includes a method of distillation, evaporation, and column chromatography.
According to the preparation method of the present invention, preferably, the silole derivative of the present invention is isolated and purified by column chromatography, and a mixed solvent of dichloromethane/petroleum ether may be used as an eluent, and the volume ratio of dichloromethane to petroleum ether is preferably 1:0.5 to 5.
The silole derivative provided by the invention has excellent photoluminescence performance and extreme pressure anti-wear performance, can emit yellow green fluorescence under ultraviolet irradiation, and can be applied to light-emitting components and devices, fluorescent probes, biological imaging, lubricating oil and lubricating grease.
In a third aspect, the present invention provides a grease.
The lubricating grease comprises the silole derivative, a thickening agent and lubricating base oil. The silole derivative accounts for 0.01-5%, preferably 0.05-1% of the total mass of the lubricating grease; the thickening agent accounts for 5-30% of the total mass of the lubricating grease, preferably 10-20%; the lubricating base oil constitutes the main component of the grease.
The thickener comprises one or more of a polyurea thickener, a lithium-based thickener, a composite lithium-based thickener, a calcium-based thickener and a composite aluminum-based thickener, preferably the polyurea thickener, the lithium-based thickener, the composite lithium-based thickener and the composite aluminum-based thickener, and most preferably the lithium-based thickener.
The lubricating base oil can be one or more of mineral oil, vegetable oil and synthetic oil, and is preferably mineral oil or synthetic oil.
The preparation method of the lubricating grease comprises the following steps: mixing lubricating base oil, thickener and silole derivative, refining, and grinding into grease. The refining operation temperature is 160-240 ℃, preferably 180-220 ℃; the refining time is not particularly limited as long as the grease is formed, and the refining operation may be completed when the temperature is raised to the refining temperature, or the refining operation may be performed for a certain time period when the temperature is raised to the refining temperature, and the refining time is generally 10 to 240min, preferably 20 to 60min. All of the lubricating base oil, the silole derivative and the thickening agent can be mixed and refined, or part of the lubricating base oil, part of the silole derivative and the thickening agent can be mixed and refined, and then the lubricating base oil, the silole derivative and the thickening agent are mixed.
The thickener can be a soap-based thickener or a non-soap-based thickener. The soap-based thickener is preferably a metal soap, which can be a single metal soap or a composite metal soap, and the metal can be one or more of lithium, sodium, calcium, aluminum, zinc, potassium, barium, lead and manganese. The non-soap-based grease thickener is preferably one or more of graphite, carbon black, asbestos, polyurea group, bentonite and organic clay.
The grease of the present invention is preferably polyurea grease, lithium-based grease and complex aluminum-based grease.
The preparation method of the polyurea lubricating grease comprises the following steps: mixing part of lubricating base oil, the silole derivative, the amine and the isocyanate, reacting for 10-60min at 65-95 ℃, continuously heating to 190-220 ℃ after the reaction is completed, refining at high temperature, adding the rest base oil, cooling to 60-120 ℃, and grinding into grease. The amine is C 2 ～C 20 Alkylamine and/or C 6 ～C 20 Aromatic amines, such as one or more of octadecylamine, cyclohexylamine, aniline; the isocyanate is C 2 ～C 20 The isocyanate of (b) may be one or more of Toluene Diisocyanate (TDI), 4' -diphenylmethane diisocyanate (MDI).
The preparation method of the lithium-based lubricating grease comprises the following steps: mixing and heating part of lubricating base oil and fatty acid in a reaction kettle, heating to 40-90 ℃, adding the aqueous solution of the silole derivative and lithium hydroxide, heating to remove water, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest lubricating base oil, cooling to 60-120 ℃, and grinding into grease. The fatty acid is C 12 ～C 20 Fatty acid and/or C 12 ～C 20 The hydroxy fatty acid can be one or more of lauric acid, palmitic acid, stearic acid and 12-hydroxystearic acid.
The preparation method of the composite aluminum-based lubricating grease comprises the following steps: mixing and heating part of base oil, fatty acid and micromolecular acid in a reaction kettle, heating to 40-90 ℃, adding the silole derivative, mixing and heating the other part of lubricating base oil and an aluminum alkoxide compound to 40-100 ℃, adding the mixture into the reaction kettle after the aluminum alkoxide compound is completely dissolved, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest of lubricating base oil, cooling to 60-120 ℃, and grinding into grease. The fatty acid is C 12 ～C 20 Fatty acid and/or C 12 ～C 20 Hydroxy fatty acid, which can be one or more of lauric acid, palmitic acid, stearic acid and 12-hydroxystearic acid; the small molecular acid is C 2 ～C 11 The organic acid of (2) can be one or more of acetic acid, propionic acid, oxalic acid, adipic acid, azelaic acid, sebacic acid and terephthalic acid; the aluminium alkoxide compound is preferably selected from aluminium isopropoxide, aluminium isopropoxide dimer, aluminium isopropoxide trimer.
According to the method for preparing a grease of the present invention, it is preferable that the silole derivative is dissolved in a solvent in advance. The solvent is preferably an aromatic hydrocarbon solvent, for example, benzene, toluene or xylene, and the weight of the solvent is 0.5 to 100 times (preferably 1 to 20 times) that of the silole derivative.
The lubricating grease has excellent photoluminescence performance and extreme pressure abrasion resistance, and can be applied to relevant mechanical equipment in the electrical appliance industry, the metallurgical industry, the food industry, the paper industry, the automobile industry and the airplane industry.
Detailed Description
In the context of the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond" is meant that the group is absent. For example, assume the structural formula-CH 2 -A-CH 3 Wherein the group a is defined as being selected from the group consisting of single bonds and methyl groups. In this respect, if A is a single bond, this means that the group A is absent, in which case the formula is correspondingly simplified to-CH 2 -CH 3 。
In the context of the present specification, the expression "number + valence + group" or the like refers to a group obtained by removing the number of hydrogen atoms represented by the number from the basic structure (such as a chain, a ring, a combination thereof, or the like) to which the group corresponds, and preferably refers to a group obtained by removing the number of hydrogen atoms represented by the number from a carbon atom (preferably a saturated carbon atom and/or a non-identical carbon atom) contained in the structure. For example, "3-valent straight or branched alkyl" refers to a straight or branched alkane (i.e., the base chain to which the straight or branched alkyl corresponds) from which 3 hydrogen atoms have been removedThe resulting group, and "2-valent straight or branched heteroalkyl" refers to a group derived from a straight or branched heteroalkane (preferably from a carbon atom contained in the heteroalkane, or further, from a non-identical carbon atom) by removal of 2 hydrogen atoms. For example, the 2-valent propyl group can be-CH 2 -CH 2 -CH 2 -*、
Figure BDA0002214432450000081
The 3-valent propyl group may be
Figure BDA0002214432450000082
The 4-valent propyl group can be->
Figure BDA0002214432450000083
Wherein represents a binding end in the group that may be bonded to other groups.
The main raw materials used are as follows:
chemical reagents such as 1-alkynyl-1, 2,3,4, 5-pentaphenylsilole, 1-methyl-1-alkynyl-2, 3,4, 5-tetraphenylsilole, bromobenzotriazolyl octadecylamine, cuprous iodide, triphenylphosphine, tetratriphenylphosphine palladium, octadecylamine, MDI, 12-hydroxystearic acid, stearic acid, benzoic acid, lithium hydroxide monohydrate, aluminum isopropoxide trimer, tetrahydrofuran, triethylamine, dichloromethane, petroleum ether, etc. are available from Bailinger reagent, imokay reagent, or Sigma reagent; the PAO10 base oil was obtained from Exxon Mobil.
Example 1
A100 mL Schlenk reaction flask is added with 1mmol of 1-alkynyl-1, 2,3,4, 5-pentaphenyl silole, 1.2mmol of bromobenzotriazole octadecylamine salt, 0.1mmol of cuprous iodide and 0.1mmol of triphenylphosphine, and added with 0.02mmol of tetratriphenylphosphine palladium and 30mL of tetrahydrofuran/triethylamine (2/1, v/v) under the protection of nitrogen, and the mixture is reacted at room temperature for 48 hours. After the reaction is finished, filtering, drying the filtrate in a spinning mode, and separating and purifying the product by using a column chromatography method by using a dichloromethane/petroleum ether (1/2, v/v) mixed solvent as an eluent to obtain a light yellow solid product with the yield of 69%. The mass spectrum result of the product is as follows: MS (MALDI-TOF): m/z calcd:872.5[ M ]] + ,found:872.5。
The reaction formula of example 1 is as follows:
Figure BDA0002214432450000084
example 2
A100 mLSchlenk reaction flask was charged with 1mmol of 1-methyl-1-alkynyl-2, 3,4, 5-tetraphenylthiapyrrole, 1.2mmol of bromobenzotriazole octadecylamine salt, 0.1mmol of cuprous iodide, 0.1mmol of triphenylphosphine, and 0.02mmol of tetratriphenylphosphine palladium, 30mL of tetrahydrofuran/triethylamine (2/1, v/v) under nitrogen atmosphere, and reacted at room temperature for 48 hours. After the reaction is finished, filtering and spin-drying the filtrate, and separating and purifying the product by column chromatography with a dichloromethane/petroleum ether (1/2, v/v) mixed solvent as an eluent to obtain a light yellow solid product with the yield of 73%. The mass spectrum result of the product is as follows: MS (MALDI-TOF) m/z calcd:810.5[ 2 ] M] + ,found:810.5。
The reaction formula of example 2 is as follows:
Figure BDA0002214432450000091
example 3
145 g of PAO10 base oil and 44.39 g of octadecylamine were mixed and heated to 60 ℃ in a reaction kettle, 2.5 g of 1- (phenyltriazolyl octadecylamine salt) -1,2,3,4, 5-pentaphenylsilole prepared in example 1 was dissolved in 25 g of toluene and added to the reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI were mixed and heated to 60 ℃ until MDI was completely dissolved, added to the reaction kettle, heated to 80 ℃ for reaction for 30 minutes, heated to 210 ℃ continuously, 145 g of PAO10 base oil was added to cool to about 100 ℃, and ground to grease.
Example 4
145 g of PAO10 base oil and 44.39 g of octadecylamine are mixed and heated to 60 ℃ in a reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI are mixed and heated to 60 ℃, the mixture is added into the reaction kettle after the MDI is completely dissolved, the temperature is increased to 80 ℃ for reaction for 30 minutes, the temperature is continuously increased to 210 ℃, 145 g of PAO10 base oil is added for cooling to about 100 ℃, 2.5 g of 1- (phenyltriazolyl octadecylamine salt) -1,2,3,4, 5-pentaphenylsilole prepared in example 1 is added, and the mixture is ground into grease.
Example 5
145 g of PAO10 base oil and 44.39 g of octadecylamine were mixed and heated to 60 ℃ in a reaction kettle, 2.5 g of 1-methyl-1- (benzenetriazolyl octadecylamine) -2,3,4, 5-tetraphenylsilole prepared in example 2 was dissolved in 25 g of toluene and then added to the reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI were mixed and heated to 60 ℃, after all MDI was dissolved, the mixture was added to the reaction kettle, the temperature was raised to 80 ℃ for reaction for 30 minutes, the temperature was further raised to 210 ℃, 145 g of PAO10 base oil was added and cooled to about 100 ℃ and then ground into grease.
Comparative example 1
145 g of PAO10 base oil and 44.39 g of octadecylamine are mixed and heated to 60 ℃ in a reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI are mixed and heated to 60 ℃, the mixture is added into the reaction kettle after the MDI is completely dissolved, the temperature is increased to 80 ℃ for reaction for 30 minutes, the temperature is continuously increased to 210 ℃, 145 g of PAO10 base oil is added to be cooled to about 100 ℃, and the mixture is ground into grease.
The greases of examples 3-5 and comparative example 1 were evaluated for performance according to GB/T3498, GB/T269, SH/T0202, SH/T0204 and SH/T0324, and the evaluation results are shown in Table 1.
TABLE 1 evaluation results
Figure BDA0002214432450000101
Example 6
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid were mixed and heated to 85 ℃ in a reaction kettle, 2.5 g of 1- (benzenetriazoletetraacetic acid octadecyl amine) -1,2,3,4, 5-pentaphenylsilole prepared in example 1 was dissolved in 25 g of toluene and added to the reaction kettle, 6.06 g of lithium hydroxide monohydrate and 40 g of distilled water were mixed and heated to 95 ℃, the mixture was added to the reaction kettle after all the lithium hydroxide was dissolved, the temperature was continuously raised to 210 ℃ after the water removal by heating, 160 g of PAO10 base oil was added, and the mixture was cooled and ground into grease.
Example 7
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid were mixed and heated to 85 ℃ in a reaction kettle, 2.5 g of 1-methyl-1- (phenyltriazoloctadecylamine) -2,3,4, 5-tetraphenylsilole obtained in example 2 was dissolved in 25 g of toluene and then added to the reaction kettle, 6.06 g of lithium hydroxide monohydrate and 40 g of distilled water were mixed and heated to 95 ℃, after all the lithium hydroxide was dissolved, the mixture was added to the reaction kettle, after heating and dewatering, the temperature was continuously raised to 210 ℃, 160 g of PAO10 base oil was added, and after cooling, the mixture was ground to grease.
Comparative example 2
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid are mixed and heated to 85 ℃ in a reaction kettle, 6.06 g of lithium hydroxide monohydrate and 40 g of distilled water are mixed and heated to 95 ℃, the mixture is added into the reaction kettle after the lithium hydroxide is completely dissolved, the temperature is continuously raised to 210 ℃ after the water is removed by heating, 160 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
The greases of example 6, example 7 and comparative example 2 were evaluated for their properties in the same manner as described above, and the results are shown in Table 2.
TABLE 2 evaluation results
Figure BDA0002214432450000111
Example 8
200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid are mixed and heated to 90 ℃ in a reaction kettle, 2.5 g of 1- (benzenetriazoletetraacetic amine) -1,2,3,4, 5-pentaphenylsilole prepared in example 1 is dissolved in 25 g of toluene and added into the reaction kettle, 100 g of PAO10 base oil and 32 g of aluminum isopropoxide trimer are mixed and heated, the mixture is added into the reaction kettle after the aluminum isopropoxide trimer is completely dissolved, the temperature is continuously raised to 210 ℃ for reaction for 30 minutes, 150 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
Example 9
200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid are mixed and heated to 90 ℃ in a reaction kettle, 2.5 g of 1-methyl-1- (phenyltriazoloctadecylamine) -2,3,4, 5-tetraphenylsilole prepared in example 2 is dissolved in 25 g of toluene and then added into the reaction kettle, 100 g of PAO10 base oil and 32 g of aluminum isopropoxide trimer are mixed and heated, the mixture is added into the reaction kettle after the aluminum isopropoxide trimer is completely dissolved, the temperature is continuously raised to 210 ℃ for reaction for 30 minutes, 150 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
Comparative example 3
Mixing 200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid in a reaction kettle, heating to 90 ℃, mixing and heating 100 g of PAO10 base oil and 32 g of aluminum isopropoxide trimer, adding the mixture into the reaction kettle after the aluminum isopropoxide trimer is completely dissolved, continuously heating to 210 ℃ for reaction for 30 minutes, adding 150 g of PAO10 base oil, cooling and grinding into grease.
The greases of example 8, example 9 and comparative example 3 were evaluated for their properties according to the same evaluation method as described above, and the evaluation results are shown in Table 3.
TABLE 3 evaluation results
Figure BDA0002214432450000121
/>

Claims (17)

1. Silole derivative, the structure of which is shown in formula (I):
Figure FDA0004057450680000011
wherein each R is 0 Are the same or different from each other and are each independently selected from hydrogen and C 1-4 Straight or branched chain alkyl, each x is independently selected from 0, 1,2, 3; the L' group is selected from
Figure FDA0004057450680000012
C 1-4 Straight or branched chain alkyl, wherein R 0 Selected from hydrogen, C 1-4 Straight or branched chain alkyl, x is selected from 0, 1,2, 3;
n is 1; the A group is selected from the group shown in the formula (II);
Figure FDA0004057450680000013
in formula (II), the R group is selected from C 1-20 A linear or branched alkylene group; each R' group is selected from H; the R' group is selected from H; each R' "group is selected from H; y is 0 or 1;
cyclic group
Figure FDA0004057450680000014
Selected from benzene rings; the L group is a single bond.
2. Silole derivatives according to claim 1, characterized in that they have the structure:
Figure FDA0004057450680000015
3. a process for producing the silole derivative according to claim 1, which comprises the step of reacting a compound represented by the formula (III) with a compound represented by the formula (IV),
Figure FDA0004057450680000021
in the formula (III), each R 0 Are the same or different from each other and are each independently selected from hydrogen, C 1-4 Straight or branched chain alkyl, each x is independently selected from 0, 1,2, 3; the L' group is selected from
Figure FDA0004057450680000022
C 1-4 Straight or branched chain alkyl, wherein R 0 Selected from hydrogen, C 1-4 Straight or branched chain alkyl, x is selected from 0, 1,2, 3;
in formula (IV), X is F, cl, br, I or OH; n is 1; a is selected from the group represented by formula (V),
Figure FDA0004057450680000023
in formula (V), the R group is selected from C 1-20 A linear or branched alkylene group; each R' group is selected from H; the R' group is selected from H; each R' "group is selected from H; y is 0 or 1;
cyclic group
Figure FDA0004057450680000024
Selected from benzene rings; the group L is a single bond.
4. The process according to claim 3, wherein the compound represented by the formula (III) is one or more selected from the group consisting of:
Figure FDA0004057450680000025
the compound shown in the formula (IV) is selected from one or more of the following compounds:
Figure FDA0004057450680000031
5. the process according to claim 3, wherein in the reaction, the molar ratio between the compound represented by the formula (III) and the compound represented by the formula (IV) is 1:0.5 to 5; the reaction temperature is 0-50 ℃.
6. The process according to claim 3, wherein in the reaction, the molar ratio between the compound represented by the formula (III) and the compound represented by the formula (IV) is 1:0.8 to 1.2; the reaction temperature is 15-35 ℃.
7. The process according to claim 3, wherein the reaction is carried out under an inert gas atmosphere.
8. The process according to claim 3, wherein a catalyst is added to the reaction, and the catalyst is one or more of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound.
9. The process according to claim 3, wherein a catalyst is added to the reaction, and the catalyst is a mixture of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, and the molar ratio of the three is 1:0.1 to 10:0.1 to 10.
10. Use of the silole derivatives according to any of claims 1-2 or prepared according to any of claims 3-9 in lubricating oils and greases.
11. A grease comprising a silole derivative according to any of claims 1 to 2 or a silole derivative obtainable by a process according to any of claims 3 to 9, a thickener and a lubricating base oil.
12. The grease of claim 11 wherein the silole derivative is present in an amount of 0.01% to 5% of the total weight of the grease; the thickening agent accounts for 5-30% of the total mass of the lubricating grease; the lubricating base oil constitutes the main component of the grease.
13. The grease of claim 11 wherein the silole derivative comprises from 0.05% to 1% of the total mass of the grease; the thickening agent accounts for 10-20% of the total mass of the lubricating grease; the lubricating base oil constitutes the main component of the grease.
14. The grease of claim 11 wherein the thickener comprises one or more of a polyurea thickener, a lithium-based thickener, a complex lithium-based thickener, a calcium-based thickener, and a complex aluminum-based thickener.
15. A method of preparing a grease according to any one of claims 11 to 14, comprising: mixing lubricating base oil, thickener and silole derivative, refining, and grinding into grease.
16. The method according to claim 15, wherein the silole derivative is dissolved in a solvent in advance, and the solvent is an aromatic hydrocarbon solvent.
17. A method for preparing a grease according to any one of claims 11 to 14, wherein the grease is a polyurea grease, a lithium-based grease, or a composite aluminum-based grease;
the preparation method of the polyurea lubricating grease comprises the following steps: mixing part of lubricating base oil, silole derivative, amine and isocyanate, reacting at 65-95 ℃ for 10-60min, continuously heating to 190-220 ℃ after complete reaction, refining at high temperature, adding the rest base oil, cooling to 60-120 ℃, and grinding into grease;
the preparation method of the lithium-based lubricating grease comprises the following steps: mixing and heating part of lubricating base oil and fatty acid in a reaction kettle, heating to 40-90 ℃, adding aqueous solution of silole derivative and lithium hydroxide, heating to remove water, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest lubricating base oil, cooling to 60-120 ℃, and grinding into grease;
the preparation method of the composite aluminum-based lubricating grease comprises the following steps: mixing and heating part of base oil, fatty acid and micromolecular acid in a reaction kettle, heating to 40-90 ℃, adding a silole derivative, mixing and heating the other part of lubricating base oil and an aluminum alkoxide compound to 40-100 ℃, adding the mixture into the reaction kettle after the aluminum alkoxide compound is completely dissolved, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest of lubricating base oil, cooling to 60-120 ℃, and grinding into grease; the fatty acid is C 12 ～C 20 Fatty acid and/or C 12 ～C 20 A hydroxy fatty acid, the small molecular acid is C 2 ～C 11 The organic acid of (1).
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