CN112707834B - Ester compound and preparation method and application thereof - Google Patents

Ester compound and preparation method and application thereof Download PDF

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CN112707834B
CN112707834B CN201911017564.5A CN201911017564A CN112707834B CN 112707834 B CN112707834 B CN 112707834B CN 201911017564 A CN201911017564 A CN 201911017564A CN 112707834 B CN112707834 B CN 112707834B
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CN112707834A (en
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张耀
段庆华
鱼鲲
李勇
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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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Priority to EP20879644.1A priority patent/EP4049994A4/en
Priority to US17/755,075 priority patent/US20230012456A1/en
Priority to PCT/CN2020/123197 priority patent/WO2021078249A1/en
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives

Abstract

The invention provides an ester compound and a preparation method and application thereof. The structure of the ester compound is shown as the formula (I):

Description

Ester compound and preparation method and application thereof
Technical Field
The invention relates to the field of petroleum products, in particular to an ester compound.
Background
Reducing frictional wear is an important means for improving fuel economy and prolonging the service life of equipment. Research shows that low molecular alkane with relatively low polarity and alkane structure can only be physically adsorbed on metal surface and has relatively low adsorption energy and thus no good lubricating effect. The sulfur, nitrogen and oxygen compounds and aromatic hydrocarbon substances with higher polarity can be stably adsorbed on the metal surface, and play a good role in lubrication. However, with increasingly strict environmental requirements, the removal of sulfur, nitrogen and aromatic substances by deep processing refining processes such as hydrofining, hydrocracking and the like has become a necessary trend in the development of oil refining, the lubricating performance of oil products is synchronously reduced, and the abrasion of engine parts is aggravated.
Therefore, the introduction of a proper amount of a lubricating property improver to improve the lubricating property of the oil becomes an effective means for solving the above-mentioned contradiction. Many additives of ester structure have been developed in the prior art.
CN 1524935A reports an application method of modified grease as a low-sulfur diesel antiwear agent, which comprises the following steps: adding 10-2000 ppm of modified oil into low-sulfur diesel oil, wherein the modified oil is prepared by mixing natural oil and alcohol or amine according to the weight ratio of 1: 0.1-5 at 50-200 deg.c for 1-20 hr, and the natural oil may be vegetable oil or animal oil. The modified grease is added into diesel oil with the sulfur content of less than 500ppm in an amount of 10-2000 ppm, so that the lubricity of low-sulfur diesel oil can be improved.
US 5282990 reports an improvement in the fuel economy of an internal combustion engine lubricating oil by incorporating into the lubricating oil an amine/amide and ester/alcohol blended friction modifier, for example, by reacting a carboxylic acid (such as oleic acid or isostearic acid) with an amine (such as diethylenetriamine or tetraethylenepentamine) and glycerol monooleate or glycerol monoricinoleate.
Although the existing ester structure additives can improve the lubricating performance of the oil, the ester structure additives have great improvement space. In view of this, there is still a need in the art for friction performance modifiers with even better performance.
Disclosure of Invention
The invention provides an ester compound and a preparation method and application thereof.
The structure of the ester compound is shown as the formula (I):
Figure BDA0002246190470000021
in formula (I), I is an integer of 1 to 10 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5); j is an integer of 1 to 10 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5);
the L radical being selected from (i + j) valent C 1-30 A hydrocarbon group, a single bond (preferably selected from (i + j) -valent C 1-20 Straight or branched alkyl, more preferably selected from (i + j) -valent C 1-10 Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C 1-30 Hydrocarbyl (preferably selected from (i + j) -valent C 1-20 Straight or branched alkyl, more preferably C selected from (i + j valent) 1-10 Straight or branched chain alkyl); when i = j =1, the L group is selected from C 1-30 Alkylene, single bond (preferably selected from C) 1-20 Straight or branched alkylene, single bond, more preferably selected from C 1-10 Linear or branched alkylene, single bond);
the individual R groups may be the same OR different from each other, each independently selected from-OR ', -N (R') 2 Wherein each R' is independently selected from C 1-10 Straight or branched alkyl, H (preferably selected from C) 1-6 Straight or branched alkyl, H, more preferably selected from C 1-3 Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from single bond, C 1-20 Alkylene (preferably C) 1-12 Straight or branched alkylene, more preferably C 1-8 Linear or branched alkylene);
m is an integer of 1 to 12 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5);
each R' group, which may be the same or different from each other, is independently selected from the group consisting of a single bond, C 1-10 Alkylene (preferably C) 1-6 Straight or branched alkylene, more preferably C 1-3 Linear or branched alkylene);
each R is 0 The groups are the same or different from each other and are each independently selected from H, C 1-10 Hydrocarbyl (preferably C) 1-6 Straight or branched alkyl, more preferably C 1-3 Straight or branched chain alkyl);
each A group, which may be the same or different from each other, is independently selected from the group consisting of a group represented by the formula (II), a group represented by the formula (III),
Figure BDA0002246190470000022
Ethylene, propylene, and at least one A group is selected from a group represented by formula (II) or a group represented by formula (III);
Figure BDA0002246190470000031
in formulae (II) and (III), each G 1 Each independently selected from the group consisting of a single bond, — R 4 -and-OR 4 - (wherein R) 4 To the N atom), wherein R 4 Is C 1-10 Alkylene (preferably C) 1-6 Straight or branched alkylene, more preferably C 1-3 Straight or branched alkylene) (each G) 1 The radicals are each independently preferably selected from the group consisting of a single bond, C 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); each G 2 Each independently selected from a single bond, a,
Figure BDA0002246190470000032
And C 1-10 Alkylene (preferably selected from the group consisting of a single bond, C 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); each R is 1 Each independently selected from C 1-18 Alkylene (preferably selected from C) 1-15 Straight or branched alkylene, C 6-15 Arylene radical, C 7-15 Alkylene aryl, more preferably selected from C 1-12 Straight or branched alkylene, C 6-12 Arylene radical, C 7-12 An alkylene aryl group;
each R is 2 Each independently selected from H, C 1-6 Straight or branched chain alkyl, -L' -OH (preferably selected from H, C) 1-3 Straight or branched alkyl, -L '-OH, more preferably H), wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is 3 Each independently selected from H, C 1-10 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000033
(preferably selected from H, C 1-6 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000034
more preferably H, C 1-3 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000035
) Wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene), G 2 The radicals are selected from single bonds,
Figure BDA0002246190470000041
And C 1-10 Alkylene (preferably selected from the group consisting of a single bond, C 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); each R is 1 Each independently selected from C 1-18 Alkylene (preferably selected from C) 1-15 Straight or branched alkylene, C 6-15 Arylene, more preferably selected from C 1-12 Straight or branched alkylene, C 6-12 An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3), R 2 The group is H, C 1-6 Straight or branched chain alkyl, -L' -OH (preferably selected from H, C) 1-3 Straight or branched alkyl, -L' -OH, more preferably H), each R) 3 Each independently selected from H, C 1-10 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000042
(preferably selected from H, C) 1-6 Straight or branched alkyl, -L' -OH, more preferably selected from H, C 1-3 Straight or branched alkyl, -L '-OH), wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene).
According to the invention, optionally, in formulae (II) and (III), each G 1 Each of the groups is independently preferably selected from single bonds; each G 2 Each independently selected from a single bond, C 1-10 Alkylene, -L' -OH; each R is 3 Each group is independently selected from H; each R is 2 Each independently selected from H, C 1-6 Straight or branched chain alkyl, -L' -OH.
According to the invention, when i = j =1, the structure of the ester compound is shown in formula (IV):
Figure BDA0002246190470000043
in formula (IV), the L group is selected from C 1-30 Alkylene, single bond (preferably selected from C) 1-20 Straight or branched alkylene, single bond, more preferably selected from C 1-10 Linear or branched alkylene, single bond).
The ester compound with a specific structure comprises one or more of the following compounds:
Figure BDA0002246190470000051
Figure BDA0002246190470000061
Figure BDA0002246190470000071
Figure BDA0002246190470000081
Figure BDA0002246190470000091
Figure BDA0002246190470000101
Figure BDA0002246190470000111
Figure BDA0002246190470000121
the invention also provides a preparation method of the ester compound, which comprises the steps of carrying out epoxidation reaction on at least one olefinic bond in the compound shown in the formula (alpha) and then carrying out reaction with the compound shown in the formula (beta),
Figure BDA0002246190470000131
Figure BDA0002246190470000132
in formula (. Alpha.), i is an integer of 1 to 10 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5); j is an integer of 1 to 10 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5);
the L group being selected from (i + j) -valent C 1-30 A hydrocarbon group, a single bond (preferably selected from (i + j) valent)C of (A) 1-20 Straight or branched alkyl, more preferably C selected from (i + j valent) 1-10 Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C 1-30 Hydrocarbyl (preferably selected from (i + j) -valent C 1-20 Straight or branched alkyl, more preferably C selected from (i + j valent) 1-10 Straight or branched chain alkyl); when i = j =1, the L group is selected from C 1-30 Alkylene, single bond (preferably selected from C) 1-20 Straight or branched alkylene, a single bond, more preferably C 1-10 Linear or branched alkylene, single bond);
the individual R groups may be the same OR different from each other, each independently selected from-OR ', -N (R') 2 Wherein each R' is independently selected from C 1-10 Straight or branched chain alkyl, H (preferably selected from C) 1-6 Straight or branched alkyl, H, more preferably selected from C 1-3 Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from single bond, C 1-20 Alkylene (preferably C) 1-12 Straight or branched alkylene, more preferably C 1-8 Linear or branched alkylene);
m is an integer of 1 to 12 (preferably an integer of 1 to 8, more preferably an integer of 1 to 5);
each R' group is the same or different from each other and is independently selected from the group consisting of a single bond, C 1-10 Alkylene (preferably C) 1-6 Straight or branched alkylene, more preferably C 1-3 Linear or branched alkylene);
each R is 0 The groups are the same or different from each other and are each independently selected from H, C 1-10 Hydrocarbyl (preferably C) 1-6 Straight or branched alkyl, more preferably C 1-3 Straight or branched chain alkyl);
each A' group, equal to or different from each other, is independently selected from the group consisting of,
Figure BDA0002246190470000133
Ethylene, propylene, and at least one a "group is selected from-CH = CH-;
in the formula (. Beta.), G 1 The radicals being selected from single bonds, -R 4 -and-OR 4 - (wherein R is 4 To the N atom), wherein R 4 Is C 1-10 Alkylene (preferably C) 1-6 Straight or branched alkylene, more preferably C 1-3 Straight or branched alkylene) (G) 1 The radicals are preferably selected from the group consisting of single bonds, C 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); g 2 The radicals are selected from single bonds,
Figure BDA0002246190470000141
And C 1-10 Alkylene (preferably selected from single bond, C) 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); each R is 1 Each independently selected from C 1-18 Alkylene (preferably selected from C) 1-15 Straight or branched alkylene, C 6-15 Arylene radical, C 7-15 Alkylene aryl, more preferably selected from C 1-12 Straight or branched alkylene, C 6-12 Arylene radical, C 7-12 An alkylene aryl group;
R 2 the group is H, C 1-6 Straight or branched chain alkyl, — L' -OH (preferably selected from H, C) 1-3 Straight or branched alkyl, -L '-OH, more preferably H), wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is 3 Each independently selected from H, C 1-10 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000142
(preferably selected from H, C 1-6 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000143
more preferably H, C 1-3 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000144
) Wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene), G 2 The radicals are selected from single bonds,
Figure BDA0002246190470000145
And C 1-10 Alkylene (preferably selected from single bond, C) 1-6 Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C 1-3 Linear or branched alkylene); each R is 1 Each independently selected from C 1-18 Alkylene (preferably selected from C) 1-15 Straight or branched alkylene, C 6-15 Arylene, more preferably selected from C 1-12 Straight or branched alkylene, C 6-12 An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3), R 2 The group is H, C 1-6 Straight or branched chain alkyl, -L' -OH (preferably selected from H, C) 1-3 Straight or branched alkyl, -L' -OH, more preferably H), each R) 3 Each independently selected from H, C 1-10 Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000146
(preferably selected from H, C) 1-6 Straight or branched alkyl, — L' -OH, more preferably selected from H, C 1-3 Straight or branched alkyl, -L '-OH), wherein the L' group is selected from C 1-10 Alkylene (preferably selected from C) 1-10 Straight or branched alkylene, C 3-10 Cycloalkylene radical, C 6-10 Arylene radical, C 7-10 Alkylene aryl, more preferably selected from C 1-6 Straight or branched alkylene, C 4-8 Cycloalkylene radical, C 6-8 Arylene);
the X group is selected from H.
According to the invention, optionally in the formula (. Beta.), G 1 The radicals being selected from single bonds, G 2 The radicals being selected from single bonds, C 1-10 An alkylene group; each R is 3 Each independently selected from H, — L' -OH; r 2 The group is H, C 1-6 Straight or branched chain alkyl, -L' -OH.
According to the preparation method of the present invention, when i = j =1, the structure of the compound represented by formula (α) is represented by formula (γ):
Figure BDA0002246190470000151
in formula (. Gamma.), the L group is selected from C 1-30 Alkylene, single bond (preferably selected from C) 1-20 Straight or branched alkylene, single bond, more preferably selected from C 1-10 Linear or branched alkylene, single bond).
According to the preparation method of the invention, the compound represented by the formula (alpha) can be selected from one or more of the following specific compounds, or condensation products of the compounds with themselves or each other: eicosenoic acid, oleic acid, linoleic acid, linolenic acid, hexadecenoic acid, tetradecenoic acid, dodecenoic acid, undecenoic acid, decenoic acid, octenoic acid, eicosenoic acid methyl ester, oleic acid methyl ester, linoleic acid methyl ester, linolenic acid methyl ester, hexadecenoic acid methyl ester, decatetraenoic acid methyl ester, dodecenoic acid methyl ester, undecenoic acid methyl ester, decenoic acid methyl ester, octenoic acid methyl ester, eicosenoic acid amide, oleic acid amide, linoleic acid amide, linolenic acid amide, hexadecenoic acid amide, decaenoic acid amide, dodecenoic acid amide, undecenic acid amide, decenoic acid amide, octenoic acid amide.
According to the preparation method of the present invention, the compound represented by the formula (β) may be optionally selected from one or more of the following specific compounds: ethylenediamine, propylenediamine, butylenediamine, pentylenediamine, hexylenediamine, phenylenediamine, nonylenediamine, decylenediamine, dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, dipentylamine, dihexylamine, dioctylamine, diisooctylamine, ethanolamine, diethanolamine, n-propanolamine, isopropanolamine, diisopropanolamine, 2-amino-1-butanol, 6-amino-1-hexanol, 8-amino-1-octanol.
According to the preparation method of the present invention, the compound represented by the formula (α) may be optionally subjected to an epoxidation reaction with an oxidizing agent. The oxidant is capable of epoxidizing at least one olefinic bond in the compound of formula (α) (conversion of an alkenyl group to an epoxy group). The oxidant comprises organic peroxide and/or inorganic peroxide, and specifically can be one or more of the following compounds: hydrogen peroxide, tert-butyl hydroperoxide, ethylbenzene hydroperoxide, cumene hydroperoxide. The reaction equivalent ratio between the compound represented by the formula (α) (in-C = C-) and the oxidizing agent is preferably 1:1 to 5, more preferably 1: 1-2; the reaction temperature is preferably 0 to 200 ℃ and more preferably 30 to 100 ℃. The time of the epoxidation reaction is preferably such that the epoxidation reaction proceeds smoothly, and in general, the longer the reaction time, the better the reaction time, preferably from 0.5 to 24 hours, and more preferably from 1 to 10 hours. The epoxidation reaction of the compound represented by the formula (α) may be carried out by a conventional phase transfer reaction, for example, by reacting hydrogen peroxide with formic acid in situ to generate peroxy acid, and then completing an oxygen atom transfer reaction with an olefinic bond, or by adding a catalyst to the epoxidation reaction of the compound represented by the formula (α). The catalyst can be a catalyst containing heteroatom metal and/or an acid catalyst, and specifically can be one or more of a titanium-silicon material, a tungstophosphate, a molybdenum-containing complex, methyl rhenium trioxide, aluminum sulfate, sulfuric acid, hydrochloric acid, nitric acid and phosphoric acid. The amount of the catalyst is preferably 0.01 to 10% by mass of the compound represented by the formula (. Alpha.).
According to the preparation method of the invention, at least one olefinic bond in the compound shown in the formula (alpha) is subjected to epoxidation reaction to generate an epoxidation product of the compound shown in the formula (alpha). The epoxidation product of the compound represented by the formula (α) may be subjected to the next reaction after purification, or may be subjected to the next reaction without purification. And (c) reacting the epoxidation product of the compound shown in the formula (alpha) with the compound shown in the formula (beta) to obtain the ester compound. The ester compound can be a compound with a single structure, and can also be a mixture containing compounds with different structures. For a mixture of compounds of different structures, it is sometimes possible to separate it into compounds of a single structure, and it is sometimes also possible to use the mixture of compounds of different structures as it is without separating it into compounds of a single structure.
According to the production process of the present invention, preferably, an epoxidation product of a compound represented by the formula (. Alpha.) in terms of epoxy group is reacted with a compound represented by the formula (. Beta.) (in terms of X-G) 1 Amount of-N) is preferably 1:0.1 to 10, more preferably 1:0.2 to 5; the reaction temperature is preferably 20 to 200 ℃ and more preferably 40 to 150 ℃. The reaction time is preferably such that the reaction proceeds smoothly, and generally, the longer the reaction time, the better, preferably from 0.5 to 24 hours, and more preferably from 2 to 16 hours.
According to the present invention, a catalyst may or may not be added, preferably a catalyst is added, to the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β). The catalyst can be one or more of inorganic acid, organic acid, solid acid, heteropoly acid, acidic ionic liquid, acidic resin, acidic molecular sieve, inorganic base, organic base, metal chloride and metal oxide, for example, sulfuric acid, perchloric acid, p-toluenesulfonic acid, acidic resin, phosphotungstic heteropoly acid, acidic ionic liquid, acidic molecular sieve, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium propoxide, sodium propoxide, alCl 3 One or more of tin chloride, n-butyl tin oxide and dibutyl tin oxide, preferably perchloric acid, tin chloride, n-butyl tin oxide, p-toluenesulfonic acid, acidic resins and phosphotungstic heteropoly acids. The amount of the catalyst added is preferably 0.1 to 10% of the amount of the compound represented by the formula (α).
According to the preparation method of the present invention, a solvent may be added or not added, preferably a solvent is added, in the epoxidation reaction of the compound represented by the formula (α) and/or the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β). The solvent is preferably a hydrocarbon solvent, preferably one or more of alkane, aromatic hydrocarbon and ether, more preferably an alkane solvent, and for example, one or more of hexane, heptane, octane, nonane, decane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, benzene, toluene, xylene, ethylbenzene, propylbenzene, diethyl ether, propyl ether, isopropyl ether and dibutyl ether may be used. The amount of the solvent to be added is not particularly limited, as long as the reaction is promoted to proceed smoothly. The solvent may be removed by a known method, for example, distillation, rectification, or the like, and is not particularly limited.
According to the production method of the present invention, in the epoxidation reaction of the compound represented by the formula (α) and/or the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β), the reaction product is preferably washed and purified with a solvent, and the solvent which can be washed is preferably a hydrocarbon solvent. The solvent may be removed by conventional techniques such as drying, evaporation, distillation, and the like. According to the preparation method of the present invention, the epoxidation reaction of the compound represented by the formula (α) and/or the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β) may be carried out in a continuous or batch reaction apparatus such as a reaction vessel, a fixed bed, a fluidized bed, a microchannel reactor, or the like.
The ester compound has excellent wear resistance and friction reduction performance, can be used as a wear resistance agent and a friction reducing agent, is suitable for being used as a wear resistance agent and a friction reducing agent of petroleum products, and is particularly used as a wear resistance agent and a friction reducing agent of lubricating grease.
The invention also provides a lubricating oil composition which comprises the ester compound or the ester compound prepared by the method and lubricating oil base oil. Wherein the ester compound accounts for 0.1-100% of the total mass of the lubricating oil composition, preferably 0.1-90%, more preferably 1-50%, further optionally 2-30%, and 3-25%. The lubricating oil composition has excellent wear resistance and friction reduction performance.
According to the present invention, the lubricating oil composition may further comprise other components. Examples of the other components include various additives which are allowed to be added to the lubricating oil composition in the art, and specific examples thereof include phenol type, amine type or sulfur phosphorus type antioxidants, carboxylate, sulfonate or alkylphenate detergents, succinimide type ashless dispersants, polyester, polyolefin or alkylnaphthalene type pour point depressants, methacrylate ester copolymers, ethylene-propylene copolymers, polyisobutylene, hydrogenated styrene/butadiene copolymer type viscosity index improvers, sulfur/phosphorus type friction modifiers, sulfur/phosphorus and boric acid type extreme pressure agents, and silicon type or non-silicon type antifoaming agents. The kind and amount of these additives are well known to those skilled in the art and will not be described herein. These additives may be used singly or in combination in any ratio.
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", it 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 a single bond and a methyl group. 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-chain or branched alkyl" refers to a group obtained by removing 3 hydrogen atoms from a straight-chain or branched alkane (i.e., the base chain to which the straight-chain or branched alkyl corresponds), and "2-valent straight-chain or branched heteroalkyl" refers to a group obtained by removing 2 hydrogen atoms from a straight-chain or branched heteroalkane (preferably from a carbon atom contained in the heteroalkane, or further, from a non-identical carbon atom). For example, the 2-valent propyl group may be-CH 2 -CH 2 -CH 2 -*、
Figure BDA0002246190470000181
The 3-valent propyl group may be
Figure BDA0002246190470000182
The 4-valent propyl group may be
Figure BDA0002246190470000183
Wherein represents a binding end in the group that may be bonded to other groups.
Example 1: preparation of epoxy methyl oleate A
The reaction was carried out in a reaction vessel equipped with a vent, stirrer and thermocouple. Adding 2000g of methyl oleate, 158g of formic acid and 15g of sulfuric acid into a reaction kettle, heating to 60 ℃, pumping 1150g of hydrogen peroxide with the concentration of 30% into the reaction kettle for 6h, removing the residual formic acid and water in a distillation mode after the reaction is finished, cooling to room temperature, and washing with deionized water for three times to obtain epoxy methyl oleate A.
Example 2: preparation of ester Compound A-1
60g of ethylenediamine and 150g of epoxy methyl oleate A were placed in a 500mL three-necked glass flask, heated to 80 ℃ and maintained at 80 ℃ for reaction for 6 hours, and excess ethylenediamine was distilled off. Washing the crude product to neutrality to obtain an ester compound A-1, wherein the structure of the ester compound A-1 is shown in the specification.
Figure BDA0002246190470000191
Example 3: preparation of ester Compound A-2
37g of diethylamine and 150g of epoxy methyl oleate A were charged into a 500mL autoclave, heated to 70 ℃ and maintained at 70 ℃ for further reaction for 5h, and excess diethylamine was distilled off. Washing the crude product to neutrality to obtain an ester compound A-2, wherein the structure of the ester compound A-2 is shown in the specification.
Figure BDA0002246190470000192
Example 4: preparation of ester Compound A-3
60g of benzamide, 2g of sodium ethoxide and 150g of epoxy methyl oleate A are added into a 500mL reaction kettle, the reaction kettle is heated to 100 ℃, the temperature is maintained at 100 ℃, the reaction is continued for 7h, and the excessive benzamide is removed by distillation. Washing the crude product to neutrality to obtain an ester compound A-3, wherein the structure of the ester compound A-3 is shown in the specification.
Figure BDA0002246190470000193
Comparative example 1: preparation of ester Compound D-1
The preparation method of D-1 is the same as that of A-1 except that ethylenediamine is replaced by ethanol with the same mole, and the ester compound D-1 is obtained.
Example 5: preparation of epoxy linoleic acid B
The reaction was carried out in a reaction vessel equipped with a vent, stirrer and thermocouple. Adding 1900g of linoleic acid, 300g of formic acid and 15g of sulfuric acid into a reaction kettle, heating to 60 ℃, pumping 2300g of hydrogen peroxide with the concentration of 30% into the reaction kettle for 6h, removing the rest formic acid and water by adopting a distillation mode after the reaction is finished, cooling to room temperature, and washing with deionized water for three times to obtain the epoxy linoleic acid B.
Example 6: preparation of ester Compound B-1
90g of ethylenediamine and 156g of methyl epoxylinoleate B were placed in a 500mL three-necked glass flask, heated to 80 ℃ and maintained at 80 ℃ for reaction for 6h, and excess ethylenediamine was removed by distillation. Washing the crude product to neutrality to obtain ester compound B-1 with the structure shown in the specification.
Figure BDA0002246190470000201
Example 7: preparation of ester Compound B-2
37g of diethylamine and 156g of methyl epoxylinoleate B were added into a 500mL high-pressure reaction kettle, heated to 70 ℃, maintained at 70 ℃ for further reaction for 5h, and excess diethylamine was removed by distillation. Washing the crude product to neutrality to obtain ester compound B-2 with the structure shown in the specification.
Figure BDA0002246190470000202
Comparative example 2: preparation of ester Compound D-2
The preparation method of D-2 is the same as that of B-2 except that diethylamine is replaced with equimolar ethanol, to obtain an ester compound D-2.
The ester compounds of examples and comparative examples were examined for their frictional wear properties, respectively, and the evaluation of lubricating properties in diesel oil was carried out according to ISO12156-1 method using a high frequency reciprocating testing machine (HFRR) and the evaluation of sliding properties in lubricating oil was carried out according to SH/T0762 method of measuring the coefficient of friction of lubricating oil (four-ball method). The results are shown in Table 1.
TABLE 1
Sample (I) Steel ball grinding spot diameter/mum Average coefficient of friction
A-1 221 0.061
A-2 237 0.063
A-3 259 0.067
D-1 531 0.089
D-2 465 0.080
B-1 202 0.060
B-2 219 0.061

Claims (9)

1. An ester compound having the structure:
Figure FDA0003772123070000011
2. a process for preparing an ester compound according to claim 1, which comprises the step of epoxidizing an olefinic bond in the compound represented by the formula (α) and reacting the product with a compound represented by the formula (β),
Figure FDA0003772123070000012
in formula (α), i is 1; j is 1; the L group is selected from C 1-30 Alkylene, single bond; r is selected from-OR', wherein R "" is selected from methyl; r' is selected from C 1-20 A hydrocarbylene group; m is an integer between 1 and 12; each R "
The groups are the same or different from each other and are each independently selected from the group consisting of a single bond, C 1-10 A hydrocarbylene group; each R is 0 The groups are the same or different from each other and are each independently selected from H, C 1-10 A hydrocarbyl group; each a' group is selected from the formula-CH = CH-;
in the formula (. Beta.), G 1 The group is selected from single bonds; g 2 The group is selected from single bonds; r 1 The group is selected from ethylene;
R 2 the group is selected from H; n is 1; each R is 3 The group is selected from H; the X group is selected from H;
further, the compound shown in the formula (alpha) is methyl oleate or methyl linoleate, and the compound shown in the formula (beta) is ethylenediamine.
3. The process according to claim 2, wherein the compound represented by the formula (α) is epoxidized with an oxidizing agent comprising an organic peroxide and/or an inorganic peroxide.
4. A process according to claim 2, wherein the epoxidation product of the compound of formula (α) is represented by X-G, and the amount of the epoxy group is represented by 1 -N, in an amount such that the equivalent ratio of the reaction between the epoxidation product of the compound of formula (α) and the compound of formula (β) is 1: 0.1E
10; the reaction temperature is 20-200 ℃.
5. A process according to claim 2, wherein the epoxidation product of the compound of formula (α) is represented by X-G, and the amount of the epoxy group is represented by 1 -N, in an amount such that the equivalent ratio of the reaction between the epoxidation product of the compound of formula (α) and the compound of formula (β) is 1: 0.2E
5; the reaction temperature is 40-150 ℃.
6. The process according to claim 2, wherein a catalyst is added to the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β), and the catalyst is one or more selected from the group consisting of an inorganic acid, an organic acid, a solid acid, a heteropolyacid, an acidic ionic liquid, an acidic resin, an acidic molecular sieve, an inorganic base, an organic base, a metal chloride and a metal oxide.
7. The process according to claim 2, wherein a catalyst is added to the reaction of the epoxidation product of the compound represented by the formula (α) with the compound represented by the formula (β), and the catalyst is selected from the group consisting of sulfuric acid, perchloric acid, p-toluenesulfonic acid, acidic resins, phosphotungstic heteropoly acids, acidic ionic liquids, acidic molecular sieves, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium propoxide, sodium propoxide, alCl 3 One or more of tin chloride, n-butyltin oxide and dibutyltin oxide.
8. Use of an ester compound according to claim 1 or prepared according to the process of any one of claims 2 to 7 as an antiwear and/or antifriction agent.
9. A lubricating oil composition comprising the ester compound of claim 1 or the ester compound obtained by the method according to any one of claims 2 to 7, and a lubricating base oil.
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