CN116789582A - Imide compound and preparation method and application thereof - Google Patents

Imide compound and preparation method and application thereof Download PDF

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Publication number
CN116789582A
CN116789582A CN202210262094.4A CN202210262094A CN116789582A CN 116789582 A CN116789582 A CN 116789582A CN 202210262094 A CN202210262094 A CN 202210262094A CN 116789582 A CN116789582 A CN 116789582A
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formula
succinic anhydride
linear
compound
group
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赵梦亚
贺景坚
梁宇翔
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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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon 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
    • 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
    • C10M133/48—Heterocyclic nitrogen compounds the ring containing both nitrogen and oxygen
    • C10M133/50—Morpholines
    • 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
    • C10M2215/086—Imides
    • 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
    • C10M2215/221—Six-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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

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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)
  • Indole Compounds (AREA)

Abstract

The invention relates to the technical field of rust inhibitors and/or antioxidants, and discloses an imide compound, a preparation method and application thereof, and a composition with rust prevention and/or antioxidant functions. The imide compound has a structure shown in a formula (I), wherein R 0 A hydrocarbon group of 3 to 20 carbon atoms; y is a group having a structure represented by formula (II), wherein in formula (II), the site bonded to the nitrogen atom in formula (I); m is an integer of 1 to 10; r in m repeating units 1 Each independently is a C1-C20 linear or branched alkylene group; t in the m repeating units is each independently a C3-C10 nitrogen-containing heterocyclic group；R 2 Selected from the group consisting of H, C C20 linear or branched alkyl, or R 2 Is not present. The imide compound has excellent rust and/or oxidation resistance, particularly has good compatibility with ester base oil, can synergistically play a role, and further improves the rust and/or oxidation resistance.

Description

Imide compound and preparation method and application thereof
Technical Field
The invention relates to the technical field of rust inhibitors and/or antioxidants, in particular to an imide compound, a preparation method and application thereof, and a composition with rust prevention and/or antioxidant functions.
Background
Lubricating oil is the most widely used lubricating material at present and mainly plays roles of lubrication, cooling, rust prevention, cleaning, sealing, buffering and the like. Lubricating oils generally consist of two parts, a base oil, which is the main component of the lubricating oil, and additives, which determine the basic properties of the lubricating oil, and which make up for and improve the deficiencies in base oil properties, giving certain new properties, which are also important components of the lubricating oil. The ester base oil has the characteristics of excellent low-temperature performance, good lubricating performance, high degradation rate, long service life and the like, and is more and more concerned, and is more and more widely applied, but has poor rust resistance, so that the rust resistance is usually improved by adding a rust inhibitor.
At present, common rust inhibitors in lubricating oils include: petroleum sulfonates, carboxylic acids, esters, and the like. The rust inhibitors still have the defects of complex process, serious pollution, low yield, limited performance, single function, less ideal rust prevention effect when used in ester base oil, and the like. Moreover, with the development of society, the demands for oxidation resistance of lubricating oils are increasing. Aiming at the defects, the development of the multifunctional additive which is green, environment-friendly, low in pollution and excellent in performance is the trend and direction of the development of the additive in the future.
US5382667a discloses a compound obtained by reacting alkenyl substituted succinic anhydrides with 4- (2-aminoethyl) morpholone or hydroxyethyl ethylenediamine for obtaining concentrates of metalworking fluids, in particular for preventing corrosion.
US6043199a discloses a turbine oil composition comprising a synthetic ester base oil, a corrosion inhibiting additive wherein the first component of the additive is a dicarboxylic acid and the second component is (a) a hydroxy derivative of a linear or branched alkyl or alkenyl succinic acid/anhydride ester or half-ester or succinic acid/anhydride ester or half-ester and (b) a linear or branched alkyl or alkenyl substituted succinimide or succinamide or mixtures thereof or an amino substituted succinimide or succinamide or mixtures thereof, and wherein the (b) component is formed by reacting a linear or branched alkyl or alkenyl substituted succinic anhydride with a substituted amino imidazoline, to provide corrosion resistance.
CN101993743B discloses an additive composition comprising an aromatic amine antioxidant and/or a hindered phenol antioxidant, an ammonolysis reaction product of an acylating agent containing two acyl groups in the component molecule and ammonia and/or amine in a molar ratio of 1: (0.5-2), a component metal deactivator, a diesel composition containing the additive composition and a method for improving oxidation stability of biodiesel by using the additive composition, wherein the diesel composition has better oxidation stability.
CN112442398A discloses a biodiesel antioxidant containing olefine-based succinimide or/and olefine-based butanediamide, which has better antioxidant property and good solubility with biodiesel.
However, the above reported imide-based materials have complicated synthesis steps, and have poor corrosion resistance when used alone, and require combination with other corrosion inhibitors to further improve corrosion resistance; and there is no report on the use of the above imide-based substances as rust inhibitors.
Disclosure of Invention
The invention aims to overcome the technical problems in the prior art and provide an imide compound, a preparation method and application thereof and a composition with rust prevention and/or oxidation resistance.
In order to achieve the above object, a first aspect of the present invention provides an imide compound having a structure represented by formula (I),
wherein in formula (I), R 0 A hydrocarbon group of 3 to 20 carbon atoms; y is a group having a structure represented by formula (II),
in formula (II), represents a site bonded to a nitrogen atom in formula (I); m is an integer of 1 to 10; r in m repeating units 1 Each independently is a C1-C20 linear or branched alkylene group; t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 Selected from the group consisting of H, C C20 linear or branched alkyl, or R 2 Is not present.
In a second aspect, the present invention provides a process for producing an imide compound, which comprises: contacting a compound shown in a formula (IV) with a compound shown in a formula (V) to carry out imidization reaction;
in the formula (IV), R 0 ' is a C3-C20 hydrocarbyl group;
in the formula (V), m is a positive integer of 1-10; r in m repeating units 1 ' each independently is a C1-C20 linear or branched alkylene group; t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 ' straight or branched alkyl selected from H, C-C20, or R 2 ' no present.
The third aspect of the invention provides an application of the imide compound or the method in antirust agent and/or antioxidant.
In a fourth aspect of the present invention, a composition having rust and/or oxidation preventing functions, the composition comprising: comprising the base oil of the imide compound or the product of imidization prepared by the method.
In a fifth aspect, the present invention provides the use of the aforementioned imide compound or the aforementioned method for improving the rust and/or oxidation resistance of an ester base oil.
The imide compound provided by the invention has excellent rust prevention and/or oxidation resistance, and better rust prevention effect than that of the conventional rust inhibitor T747A (alkenyl succinic acid ester) used in ester oil, so that the imide compound can be used as an additive of lubricating oil, particularly has good compatibility with ester base oil, can act synergistically, and further improves the rust prevention and/or oxidation resistance.
Drawings
FIG. 1 is an infrared spectrum of product 1 of example 1 of the present invention;
FIG. 2 is a mass spectrum of product 1 of example 1 of the present invention;
FIG. 3 is an infrared spectrum of product 2 of example 2 of the present invention;
FIG. 4 is a mass spectrum of product 2 in example 2 of the present invention.
Detailed Description
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
In the present invention, "C3-C20 hydrocarbon group" means a branched or straight-chain alkyl group, alkenyl group or alkynyl group having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms. "C1-C6 straight or branched chain alkylene" means methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl.
"C3-C10 nitrogen-containing heterocyclic group" means a nitrogen-containing heterocyclic ring having 3, 4, 5, 6, 7, 8, 9, 10 carbon atoms, and the nitrogen-containing heterocyclic ring may contain other hetero atoms such as O or S.
The first aspect of the present invention provides an imide compound having a structure represented by the formula (I),
wherein in formula (I), R 0 A hydrocarbon group of 3 to 20 carbon atoms; y is a group having a structure represented by formula (II),
in formula (II), represents a site bonded to a nitrogen atom in formula (I); m is an integer of 1-10 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10); r in m repeating units 1 Each independently is a linear or branched alkylene of C1-C20 (having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms); t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 A linear or branched alkyl group selected from H, C1 to C20 (having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms), or R 2 Absence (R) 2 Absence means R 2 No chemical bond and no group exists between T).
According to some embodiments of the invention, in formula (I), R 0 May be a C6-C18 hydrocarbon group, preferably a C9-C18 hydrocarbon group, more preferably a C12-C18 hydrocarbon group.
According to some embodiments of the invention, in formula (II), m may be an integer from 1 to 5, preferably 1 or 2; r in m repeating units 1 May each independently be a C1-C10 linear or branched alkylene group, preferably a C1-C6 (more preferably C1-C4) linear or branched alkylene group; t in the m repeating units may each independently be a C3-C6 nitrogen-containing heterocyclic group.
According to some embodiments of the invention, T has a structure of formula (III),
in the formula (III), R 3 And R is 4 May each independently be a C1-C9 linear or branched alkylene group, preferably a C1-C6 (more preferably C1-C4) linear or branched alkylene group, and R 3 And R is R 4 The sum of carbon atoms of (a) is an integer of 3 to 10 (e.g., 3, 4, 5, 6, 7, 8, 9, 10), preferably an integer of 3 to 8; a is O or NR 5 ，R 5 A linear or branched alkyl group selected from H, C1 to C6 (more preferably C1 to C4).
According to some embodiments of the invention, the imide compound has a structure represented by formula (I'):
in the formula (I'), X is NH or O; n is an integer of 0 to 6; l is a C1-C18 linear or branched alkylene group (number of carbon atoms 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18) or is absent; q isOr is absent; when Q is +.>When p is an integer from 0 to 18 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18); r is R 6 、R 7 And R is 8 Each independently selected from H, C1-C6 alkyl (more preferably C1-C4 alkyl);
preferably, the sum of the number of carbon atoms in L and the value of p is an integer not less than 8 and not more than 20 (e.g., 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20).
According to some embodiments of the invention, the imide compound has a structure represented by formula (I "):
in formula (I'), X may be NH or O; n is an integer from 0 to 6 (0, 1, 2, 3, 4, 5, 6); l is absent or a C1-C6 (more preferably C1-C4) linear or branched alkylene group; p is an integer from 6 to 15 (6, 7, 8, 9, 10, 11, 12, 13, 14, 15); r is R 6 、R 7 And R is 8 Each independently selected from H, C1-C6 alkyl groups.
According to some embodiments of the invention, the imide compound may be selected from at least one of the following compounds:
wherein, in the formulae (M1) to (M3), the groups in brackets represent that the double bond may be at any position (also including the case where the double bond is directly linked to the succinimide ring). In the formulae (M1) and (M2), the end of the radical in brackets is preferably isopropyl.
According to some embodiments of the invention, the imide compound may be selected from at least one of the following compounds:
in a second aspect, the present invention provides a process for producing an imide compound, which comprises: contacting a compound shown in a formula (IV) with a compound shown in a formula (V) to carry out imidization reaction;
in the formula (IV), R 0 ' may be a C3-C20 hydrocarbon group;
in the formula (V), m can be a positive integer of 1-10; r in m repeating units 1 ' each ofIndependently a C1-C20 linear or branched alkylene group; t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 ' straight or branched alkyl selected from H, C-C20, or R 2 Absence (R) 2 ' absence means R 2 ' no chemical bond and no group exists between T).
According to some embodiments of the invention, in formula (IV), R 0 ' may be a C6-C18 hydrocarbon group, preferably a C9-C18 hydrocarbon group, more preferably a C12-C18 hydrocarbon group.
According to some embodiments of the invention, in formula (V), m is an integer from 1 to 5, preferably 1 or 2; r in m repeating units 1 ' are each independently a C1-C10 linear or branched alkylene group, preferably a C1-C6 (more preferably C1-C4) linear or branched alkylene group; t in the m repeating units is each independently a C3-C6 nitrogen-containing heterocyclic group.
The structure of T according to the second aspect of the present invention is as described above, and will not be described here.
According to a preferred embodiment of the invention, the method comprises: contacting a compound shown in a formula (VI) with a compound shown in a formula (VII) to carry out imidization reaction:
in the formula (VI) or the formula (VII), X is NH or O; n is an integer of 0 to 6; l is absent or is a C1-C6 linear or branched alkylene group; p is an integer of 6 to 15; r is R 6 、R 7 And R is 8 Each independently selected from H, C1-C6 alkyl groups.
According to some embodiments of the present invention, the compound of formula (IV) may be selected from one of octyl succinic anhydride, nonyl succinic anhydride, decyl succinic anhydride, dodecyl succinic anhydride, tridecyl succinic anhydride, tetradecyl succinic anhydride, pentadecyl succinic anhydride, hexadecyl succinic anhydride, octadecyl succinic anhydride, eicosyl succinic anhydride, octenyl succinic anhydride, nonenyl succinic anhydride, decenyl succinic anhydride, dodecenyl succinic anhydride, tetradecenyl succinic anhydride, pentadecyl succinic anhydride, hexadecenyl succinic anhydride, octadecyl succinic anhydride, and isostearyl succinic anhydride.
According to some embodiments of the invention, the compound of formula (V) is selected from one of 4-aminomorpholine, 3-methyl-4-aminomorpholine, 4- (2-aminomethyl) morpholine, 4- (2-aminoethyl) morpholine, 3-methyl-4- (2-aminoethyl) morpholine, N- (3-aminopropyl) morpholine, 4-morpholinbutamine, 1, 4-bis- (3-aminopropyl) piperazine, N- (3-aminopropyl) piperazine, 1, 4-piperazinediethylamine, 1- (2-aminoethyl) piperazine, 2-methyl-1- (2-aminoethyl) piperazine, 1, 4-piperazinediamine, piperazine-1-methylamine, 1, 4-diaminopiperazine, 2-methyl-1, 4-piperazinediamine, 2- (2-methylpiperazin-1-yl) -1-ethylamine, 2-methyl-2- (4-morpholin) propylamine, 2- (2-methylmorpholin-4-yl) ethane-1-amine.
According to some embodiments of the invention, the compound of formula (IV) is dodecenyl succinic anhydride or isostearyl succinic anhydride, and the compound of formula (V) is 4- (2-aminoethyl) morpholine or 1- (2-aminoethyl) piperazine.
Preferably, the compound shown in the formula (IV) is isostearyl succinic anhydride, and the compound shown in the formula (V) is 4- (2-aminoethyl) morpholine; or alternatively, the process may be performed,
the compound shown in the formula (IV) is isostearenyl succinic anhydride, and the compound shown in the formula (V) is 1- (2-aminoethyl) piperazine; or alternatively, the process may be performed,
the compound shown in the formula (IV) is dodecenyl succinic anhydride, and the compound shown in the formula (V) is 1- (2-aminoethyl) piperazine.
The conditions of the imidization reaction are not particularly limited in the present invention, as long as the requirements of the present invention can be satisfied. Preferably, the imidization reaction is carried out at a temperature of 40 to 180 ℃, preferably 50 to 160 ℃; the time is 0.5-20h, preferably 1-15h.
According to some embodiments of the invention, the molar ratio of the compound of formula (IV) to the compound of formula (V) may be 1: (0.3-2), preferably 1: (0.4-1.5).
In the present invention, the manner of charging the imide reaction is not particularly limited as long as the requirements of the present invention can be satisfied. In order to obtain a better effect, the feeding manner of the imide reaction can be carried out as follows: the material containing the compound of formula (V) is added (preferably dropwise) to the material containing the compound of formula (IV). Wherein the material of the compound of formula (V) is added at a rate of 0.01 to 0.04mol/min relative to 1mol of the compound of formula (IV).
According to some embodiments of the invention, the imidization reaction is performed under the protection of an inert atmosphere provided by an inert gas and/or nitrogen.
In the present invention, the imidization reaction is performed in the presence of a solvent. Wherein the solvent is preferably a hydrocarbon solvent, for example the solvent may be a C6-C10 aromatic hydrocarbon, preferably at least one from toluene, ortho-xylene, meta-xylene, para-xylene and ethylbenzene.
In the present invention, the amount of the solvent is not particularly limited, and it is preferable to promote the smooth progress of the reaction. For example, the solvent may be used in an amount of 0.5 to 2 times the total weight of the compound represented by formula (IV) and the compound represented by formula (V). Wherein the solvent may be removed after the end of the reaction by methods conventional in the art, such as distillation, rectification, etc. In the invention, the system after the reaction can be subjected to water removal operation (such as a water separator) before the solvent is removed; the step of removing water may be carried out in a manner conventional in the art, such as gradually heating the reacted system.
According to the present invention, after the completion of the imide reaction, the reaction product may be subjected to a purification treatment, and the method of the purification treatment may include at least one of water washing, distillation, rectification, molecular distillation, filtration, drying, and recrystallization methods, which are not particularly limited.
According to the present invention, the reaction product of the imide reaction may be a single imide compound or a mixture of a plurality of imide compounds. The differences in the form of the reaction products of these imidization reactions described above do not affect the achievement of the effects of the present invention. Therefore, according to the present invention, a post-purification treatment (as the purification or separation method, column chromatography or preparative chromatography may be used) may be performed, or further purification may not be performed. Of course, such purification or isolation is preferable for further improvement of the effect of the present invention.
The method for preparing the imidization reaction has the advantages of simple process, mild condition, safety and no toxicity.
The third aspect of the invention provides an application of the imide compound or the method in antirust agent and/or antioxidant.
In particular, the imide compound provided by the invention can be used as an additive (such as an antirust agent and/or an antioxidant) of ester base oil.
In a fourth aspect of the present invention, a composition having rust and/or oxidation preventing functions, the composition comprising: comprising the base oil of the imide compound or the product of imidization prepared by the method.
According to some embodiments of the present invention, the base oil may be present in an amount of 94 to 99.5wt% and the imide compound may be present in an amount of 0.19 to 0.98wt%, based on the total weight of the composition.
According to some embodiments of the invention, the imide compound may be 2 to 10g, preferably 4 to 8g, by weight relative to 1kg of base oil.
According to some embodiments of the invention, the base oil may be an ester base oil, preferably a neopentyl polyol ester base oil. The ester base oil is more preferably formed by condensing an alcohol with a carboxylic acid,
the alcohol is a polyol represented by the formula (VI), the carboxylic acid is a saturated monocarboxylic acid with 4-20 carbon atoms,
in the formula (VI), R 9 、R 10 、R 11 、R 12 Each independently selected from H, C C10 alkyl or hydroxy, and R 9 、R 10 、R 11 、R 12 At least 2 of which are hydroxyl groups.
According to some embodiments of the invention, the composition may further contain an antioxidant and/or an extreme pressure antiwear agent.
According to some embodiments of the invention, the antioxidant may be present in an amount of 0.1 to 4wt% and the extreme pressure antiwear agent may be present in an amount of 0.2 to 1.5wt%, based on the total weight of the composition.
According to some embodiments of the invention, the antioxidant is selected from at least one of aminothioesters, alkylated diphenylamines, N-phenyl-alpha-naphthylamine, and shielding phenols.
According to some embodiments of the invention, the extreme pressure antiwear agent may be selected from phosphate esters and/or phosphate amine salts. The extreme pressure antiwear agent is preferably at least one selected from di-n-butyl phosphite, tricresyl phosphate and octadecyl phosphate.
According to some embodiments of the invention, the ester base oil may be selected from at least one of neopentyl glycol ester, trimethylolpropane ester, and pentaerythritol ester.
In a fifth aspect, the present invention provides the use of the aforementioned imide compound or the aforementioned method for improving the rust and/or oxidation resistance of an ester base oil. Wherein the imide compound and the method are as described above.
The present invention will be described in detail by examples.
In the following examples, the starting materials used, solvents were all commercially available, unless otherwise specified.
Example 1
A toluene solution of isostearyl succinic anhydride (isostearyl succinic anhydride 35.09 g+toluene 70.03 g) was added to the three-necked flask, and mechanical stirring, a nitrogen gas pipe, and a constant pressure dropping funnel were installed; a toluene solution of 4- (2-aminoethyl) -morpholine (4- (2-aminoethyl) -morpholine 11.97 g+toluene 26.00 g) was prepared and the toluene solution of 4- (2-aminoethyl) -morpholine was poured into a constant pressure dropping funnel; placing the three-neck flask in a constant-temperature oil bath at 5 ℃, starting mechanical stirring and introducing nitrogen for 30 minutes; stopping introducing nitrogen, and dropwise adding a toluene solution of 4- (2-aminoethyl) -morpholine into the three-neck flask; when the dripping is finished, the time is 35min; the constant pressure dropping funnel is removed, the water separator and the condenser pipe are replaced by the toluene, the temperature of the oil bath is raised to 60 ℃ and kept constant for 2 hours, then the temperature is raised to 90 ℃ and kept constant for 2 hours, and finally the temperature is raised to 150 ℃ until no water is condensed in the water separator. Toluene was removed from the reacted mixture by spin-evaporation to obtain a product 1 (a product containing a compound having a structure represented by the above formula (a)).
The infrared spectrum of the product 1 is determined, see fig. 1.
Determination conditions of infrared spectrum:
instrument model: siemens technology NICOLET IS50, instrument parameters: the scanning times are 16 times, the resolution is 4cm -1 Scanning range 4000-400cm -1 The product adopts a smear method.
In FIG. 1, 1772cm -1 And 1699cm -1 Symmetrical and asymmetrical stretching vibration peaks of cyclic imide carbonyl C=O, 1206cm -1 C-N stretching vibration peak of cyclic imide, 978cm -1 Is double bond = C-H trans-configured out-of-plane bending vibration peak. The infrared spectrum test results show that the product 1 has a cyclic imide group and a double bond.
Mass spectrometry was performed on product 1, see figure 2.
The measurement conditions of the mass spectrum were as follows:
fourier transform ion cyclotron resonance mass spectrometer (FT-ICR MS), model Bruker SolariX XR, magnetic field strength 15T. Experimental conditions: sample injection rate 120 muL/h, electrospray ion source, positive ion mode (ESI+), capillary voltage 4500V, atomizer 1bar, drying air flow rate 4.0L/min, dryer temperature 200 ℃, TOF 0.6ms, Q1 mass 150u, RF 800Vpp, front and rear baffle voltage 1.8V, SEP (Sweep Excitation Power) 15, mass-to-charge ratio (m/z) detection range 50-1500, scanning accumulation 64 times during sampling. Sample preparation: a sample of about 0.1mg/mL was prepared with chromatographically pure methanol. 485.3719 in FIG. 2 is product 1 combined with Na + Molecular ion peaks of (2).
The above results indicate that this example successfully synthesizes product 1 containing the structural compound represented by formula (a).
Example 2
A toluene solution of isostearyl succinic anhydride (30.08 g of isostearyl succinic anhydride+ 70.05g of toluene) was added to a three-necked flask, and mechanical stirring, a nitrogen gas pipe, and a constant pressure dropping funnel were installed; a toluene solution of 1- (2-aminoethyl) piperazine (11.75 g of 1- (2-aminoethyl) piperazine+23.52 g of toluene) was prepared, and the toluene solution of 1- (2-aminoethyl) piperazine was poured into a constant pressure dropping funnel; placing the three-neck flask in a constant-temperature oil bath at 5 ℃, starting mechanical stirring and introducing nitrogen for 30 minutes; stopping introducing nitrogen, and dropwise adding a toluene solution of 1- (2-aminoethyl) piperazine into the three-neck flask; when the dripping is finished, the time is 30min; the constant pressure dropping funnel is removed, the water separator and the condenser pipe are replaced by the toluene, the temperature of the oil bath is raised to 60 ℃ and kept constant for 1.5 hours, then the temperature is raised to 90 ℃ and kept constant for 2 hours, and finally the temperature is raised to 160 ℃ until no water is condensed in the water separator. Toluene was removed from the reacted mixture by spin-evaporation to obtain a product 2 (a product containing a compound having a structure represented by the above formula (b)).
The infrared spectrum of the product 2 is determined, see fig. 3.
The infrared spectrum was measured under the following conditions: instrument model: siemens technology NICOLET IS50, instrument parameters: the scanning times are 16 times, the resolution is 4cm -1 Scanning range 4000-400cm -1 The product adopts a smear method.
In FIG. 3, 1771cm -1 And 1702cm -1 Symmetrical and asymmetrical stretching vibration peaks of cyclic imide carbonyl C=O, 1188cm -1 C-N stretching vibration peak of cyclic imide, 977cm -1 Is double bond = C-H trans-configured out-of-plane bending vibration peak. The infrared spectrum test results show that the product 1 has a cyclic imide group and a double bond.
Mass spectrometry was performed on product 2, see figure 4.
The measurement conditions of the mass spectrum were as follows:
fourier transform ion cyclotron resonance mass spectrometer (FT-ICR MS), model Bruker SolariX XR, magnetic field strength 15T. Experimental conditions: sample injection rate 120 muL/h, electrospray ion source, positive ion mode (ESI+), capillary voltage 4500V, atomizer 1bar, drying air flow rate 4.0L/min, dryer temperature 200 ℃, TOF 0.6ms, Q1 mass 150u, RF 800Vpp, front and rear baffle voltage 1.8V, SEP (Sweep Excitation Power) 15, mass-to-charge ratio (m/z) detection range 50-1500, scanning accumulation 64 times during sampling. Sample preparation: a sample of about 0.1mg/mL was prepared with chromatographically pure methanol. 462.4060 in FIG. 4 is product 2 combined with an H + Molecular ion peaks of (2).
The above results indicate that this example successfully synthesizes product 2 containing the structural compound represented by formula (b).
Example 3
An orthoxylene solution of dodecenyl succinic anhydride (dodecenyl succinic anhydride 42.65 g+orthoxylene 50 g) was added to a three-neck flask, and a mechanical stirring, a nitrogen gas conduit, and a constant pressure dropping funnel were installed; preparing an o-xylene solution of 1- (2-aminoethyl) piperazine (24.82 g of 1- (2-aminoethyl) piperazine+ 25.01g of o-xylene), and pouring the o-xylene solution of 1- (2-aminoethyl) piperazine into a constant pressure dropping funnel; placing the three-neck flask in a constant-temperature oil bath at 5 ℃, starting mechanical stirring and introducing nitrogen for 30 minutes; stopping introducing nitrogen, and dropwise adding an o-xylene solution of 1- (2-aminoethyl) piperazine into the three-neck flask; when the dripping is finished, the time is 42min; the constant pressure dropping funnel is removed, the water separator and the condenser pipe are replaced by the water separator filled with o-xylene, the temperature of the oil bath is raised to 50 ℃ and kept constant for 1h, then the temperature is raised to 80 ℃ and kept constant for 3h, and finally the temperature is raised to 150 ℃ until no water is condensed in the water separator. The reacted mixture was subjected to rotary evaporation to remove o-xylene, whereby product 3 (a product containing the compound represented by the above formula (c)) was obtained.
Test results for product 3:
1773cm -1 and 1700cm -1 Symmetrical and asymmetrical stretching vibration peaks for cyclic imide carbonyl C=O, 1195cm -1 C-N stretching vibration peak of cyclic imide, 979cm -1 Is double bond = C-H trans-configured out-of-plane bending vibration peak. The above infrared spectrum results show that the product 3 has a cyclic imide group and a double bond, which indicates that the product 3 containing the structural compound represented by the formula (c) was successfully synthesized in this example.
Test example 1
Determination of rust inhibitive Property
T747A (alkenyl succinic acid ester rust inhibitor) is selected as a comparison additive 1; mineral oil (150N) is selected as the comparison base oil 1; polyalphaolefin (PAO 6) is selected as the comparative base oil 2; diester (dioctyl sebacate) was chosen as the comparative base oil 3.
The rust inhibitive effect of the above-prepared products 1, 2, 3 and comparative additive 1 (T747A (alkenyl succinate rust inhibitive agent)) in lubricating oil was evaluated by using the GB/T11143A method, respectively.
The rust inhibitive performance of the additives (products 1, 2, 3 and T747A above) was evaluated by adding 8g/kg of the additive to the base oil (pentaerythritol ester base oil), respectively. The test method GB/T11143A specifies a method for determining the rust inhibitive performance of inhibitor mineral oil in the presence of water, which comprises the following specific steps: 300mL of the sample was mixed with 30mL of distilled water, and the whole cylindrical test steel bar was immersed therein, followed by stirring at 60 ℃. The test period is 24 hours, and the trace and the degree of rust of the test steel bar are observed after the test period is finished. The rust inhibitive performance test results are shown in Table 1.
TABLE 1
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As can be seen from the results of Table 1, the addition of the imide compound provided by the present invention has a great improvement in rust of the specific ester base oils provided by the present invention, which is better than the above-mentioned comparative additives.
Test example 2
Evaluation of antioxidant Properties
The oxidation resistance of the products 1, 2, 3 at 240℃was assessed by the SH/T0719 method, respectively.
The antioxidant properties of the additives were evaluated by adding 5g/kg of the additive (products 1, 2, 3 prepared above) to the ester base oil (pentaerythritol ester base oil), respectively. Test method SH/T0719 specifies a lubricating oil oxidation induction period assay, which comprises the following specific methods: a small amount of sample was weighed with a sample dish and placed in a PDSC meter test cell. And heating the PDSC instrument test tank to a specified temperature, and introducing oxygen with a certain pressure after balancing. The PDSC meter cell was maintained at the specified temperature and oxygen pressure until the exothermic oxidation reaction occurred. The extrapolated inflection point time was measured as the oxidation induction period of the lubricating oil at the prescribed test temperature. The results of the antioxidant test are shown in Table 2.
TABLE 2
As can be seen from Table 2, the addition of the imide compound provided by the invention has a good oxidation resistance effect on lubricating oil (especially on a system containing ester base oil (such as pentaerythritol ester base oil)).
Test example 3
The lubricating properties are the basic properties of the lubricating oil, and the lubricating properties of the pentaerythritol ester base oil and the lubricating oil after compounding the additives were evaluated by using the GB/T3142-2019 method (test conditions: 1200rpm, 392N, 75 ℃ C. For 60 min), and the average mill-base diameter results obtained are shown in Table 3.
TABLE 3 Table 3
Oil sample Average mill spot diameter (mm)
Pentaerythritol ester base oil 0.91
Pentaerythritol ester base oil+product 2 0.91
As can be seen from Table 3, after the imide compound provided by the invention is added, the lubricating oil has improved rust resistance and/or oxidation resistance, and other basic characteristics are not reduced. The product 1 obtained in example 1 and the product 3 obtained in example 3 also have similar results in terms of basic properties of the lubricating oil.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.

Claims (14)

1. An imide compound, which is characterized in that the imide compound has a structure shown in a formula (I),
wherein in formula (I), R 0 A hydrocarbon group of 3 to 20 carbon atoms; y is a group having a structure represented by formula (II),
in formula (II), represents a site bonded to a nitrogen atom in formula (I); m is an integer of 1 to 10; r in m repeating units 1 Each independently is a C1-C20 linear or branched alkylene group; t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 Selected from the group consisting of H, C C20 linear or branched alkyl, or R 2 Is not present.
2. The imide compound of claim 1 wherein in formula (I), R 0 A C6-C18 hydrocarbon group, preferably a C9-C18 hydrocarbon group, more preferably a C12-C18 hydrocarbon group;
and/or in formula (II), m is an integer from 1 to 5, preferably 1 or 2; r in m repeating units 1 Each independently is a C1-C10 linear or branched alkylene group, preferably a C1-C6 linear or branched alkylene group; t in the m repeating units is each independently a C3-C6 nitrogen-containing heterocyclic group.
3. The imide compound according to claim 1 or 2, wherein T has a structure represented by the formula (III),
in the formula (III), R 3 And R is 4 Each independently is a C1-C9 linear or branched alkylene group, preferably a C1-C6 linear or branched alkylene group, and R 3 And R is R 4 The sum of carbon atoms of (2) is an integer of 3 to 10, preferably an integer of 3 to 8; a is O or NR 5 ，R 5 A linear or branched alkyl group selected from H, C1-C6.
4. The imide compound according to claim 3, wherein the imide compound has a structure represented by the formula (I'):
in the formula (I'), X is NH or O; n is an integer of 0 to 6; l is a C1-C18 linear or branched alkylene group or is absent; q isOr is absent, p is an integer from 0 to 18; r is R 6 、R 7 And R is 8 Each independently selected from H, C1-C6 alkyl;
preferably, the sum of the number of carbon atoms in L and the value of p is an integer of not less than 8 and not more than 20.
5. The imide compound according to claim 1 or 2, wherein the imide compound is selected from at least one of the following compounds:
6. a method for producing an imide compound, comprising: contacting a compound shown in a formula (IV) with a compound shown in a formula (V) to carry out imidization reaction;
in the formula (IV), R 0 ' is a C3-C20 hydrocarbyl group;
in the formula (V), m is a positive integer of 1-10; r in m repeating units 1 ' each independently is a C1-C20 linear or branched alkylene group; t in the m repeating units is independently a C3-C10 nitrogen-containing heterocyclic group; r is R 2 ' straight or branched alkyl selected from H, C-C20, or R 2 ' no present.
7. The process of claim 6, wherein in formula (IV), R 0 ' is a C6-C18 hydrocarbyl group, preferably a C9-C18 hydrocarbyl group, more preferably a C12-C18 hydrocarbyl group;
and/or, in formula (V), m is an integer from 1 to 5, preferably 1 or 2; r in m repeating units 1 ' each independently is a C1-C10 linear or branched alkylene group, preferably a C1-C6 linear or branched alkylene group; t in the m repeating units is each independently a C3-C6 nitrogen-containing heterocyclyl, preferably a C4-C6 nitrogen-containing heterocyclyl;
preferably, T has a structure represented by formula (III),
in the formula (III), R 3 And R is 4 Each independently is a C1-C9 linear or branched alkylene group, preferably a C1-C6 linear or branched alkylene group, and R 3 And R is R 4 The sum of carbon atoms of (2) is an integer of 3 to 10, preferably an integer of 3 to 8; a is O or NR 5 ，R 5 A linear or branched alkyl group selected from H, C1-C6.
8. The method according to claim 6 or 7, wherein the compound represented by formula (IV) is selected from one of octyl succinic anhydride, nonyl succinic anhydride, decyl succinic anhydride, dodecyl succinic anhydride, tridecyl succinic anhydride, tetradecyl succinic anhydride, pentadecyl succinic anhydride, hexadecyl succinic anhydride, octadecyl succinic anhydride, eicosyl succinic anhydride, octenyl succinic anhydride, nonenyl succinic anhydride, decenyl succinic anhydride, dodecenyl succinic anhydride, tetradecenyl succinic anhydride, pentadecyl succinic anhydride, hexadecenyl succinic anhydride, octadecyl succinic anhydride, and isostearyl succinic anhydride;
and/or one of the compounds of formula (V) selected from 4-aminomorpholine, 3-methyl-4-aminomorpholine, 4- (2-aminomethyl) morpholine, 4- (2-aminoethyl) morpholine, 3-methyl-4- (2-aminoethyl) morpholine, N- (3-aminopropyl) morpholine, 4-morpholinbutamine, 1, 4-bis- (3-aminopropyl) piperazine, N- (3-aminopropyl) piperazine, 1, 4-piperazine diethylamine, 1- (2-aminoethyl) piperazine, 2-methyl-1- (2-aminoethyl) piperazine, 1, 4-piperazine dimethylamine, piperazine-1-methylamine, 1, 4-diaminopiperazine, 2-methyl-1, 4-piperazine diamine, 2- (2-methylpiperazin-1-yl) -1-ethylamine, 2-methyl-2- (4-morpholinopropylamine, 2- (2-methylmorpholin-4-yl) ethane-1-amine;
preferably, the compound shown in the formula (IV) is dodecenyl succinic anhydride or isostearyl succinic anhydride, and the compound shown in the formula (V) is 4- (2-aminoethyl) morpholine or 1- (2-aminoethyl) piperazine;
more preferably, the compound of formula (IV) is isostearyl succinic anhydride and the compound of formula (V) is 4- (2-aminoethyl) morpholine; or alternatively, the process may be performed,
the compound shown in the formula (IV) is isostearenyl succinic anhydride, and the compound shown in the formula (V) is 1- (2-aminoethyl) piperazine; or alternatively, the process may be performed,
the compound shown in the formula (IV) is dodecenyl succinic anhydride, and the compound shown in the formula (V) is 1- (2-aminoethyl) piperazine.
9. A process according to claim 6 or 7, wherein the imidisation reaction temperature is 40-180 ℃, preferably 50-160 ℃; the time is 0.5-20h, preferably 1-15h;
and/or the molar ratio of the compound represented by the formula (IV) to the compound represented by the formula (V) is 1: (0.3-2), preferably 1: (0.4-1.5);
and/or the imidization reaction is performed under the protection of an inert atmosphere provided by inert gas and/or nitrogen.
10. Use of the imide compound of any one of claims 1 to 5 or the method of any one of claims 6 to 9 in rust inhibitors and/or antioxidants.
11. A composition having rust and/or oxidation preventing functions, comprising: comprising a base oil and the imide compound of any one of claims 1 to 5 or the product of the imidization reaction produced according to the method of any one of claims 6 to 9;
preferably, the base oil is present in an amount of 94 to 99.5wt% and the imide compound is present in an amount of 0.19 to 0.98wt% based on the total weight of the composition;
preferably, the imide compound is contained in an amount of 2 to 10g relative to 1kg of the base oil.
12. The composition of claim 11, wherein the base oil is an ester base oil, wherein the ester base oil is preferably formed by condensing an alcohol with a carboxylic acid,
the alcohol is a polyol represented by the formula (VI), the carboxylic acid is a saturated monocarboxylic acid with 4-20 carbon atoms,
in the formula (VI), R 9 、R 10 、R 11 、R 12 Each independently selected from H, C C10 alkyl or hydroxy, and R 9 、R 10 、R 11 、R 12 At least 2 of which are hydroxyl groups;
and/or the composition further comprises an antioxidant and/or an extreme pressure antiwear agent;
preferably, the content of the antioxidant is 0.1-4wt% based on the total weight of the composition, and the content of the extreme pressure antiwear agent is 0.2-1.5wt%;
preferably, the antioxidant is selected from at least one of aminothioesters, alkylated diphenylamines, N-phenyl-alpha-naphthylamine and shielding phenols;
preferably, the extreme pressure antiwear agent is selected from phosphate esters and/or phosphate amine salts.
13. The composition of claim 11 or 12, wherein the ester base oil is selected from at least one of neopentyl glycol esters, trimethylol propane esters, and pentaerythritol esters.
14. Use of an imide compound as claimed in any one of claims 1 to 5 or a method as claimed in any one of claims 6 to 9 to improve rust and/or oxidation resistance of an ester base oil.
CN202210262094.4A 2022-03-16 2022-03-16 Imide compound and preparation method and application thereof Pending CN116789582A (en)

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Publication number Priority date Publication date Assignee Title
JP7500693B2 (en) 2022-11-25 2024-06-17 日本化薬株式会社 Compound, curable resin composition and cured product thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7500693B2 (en) 2022-11-25 2024-06-17 日本化薬株式会社 Compound, curable resin composition and cured product thereof

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