CN112707834A - Ester compound and preparation method and application thereof - Google Patents

Ester compound and preparation method and application thereof Download PDF

Info

Publication number
CN112707834A
CN112707834A CN201911017564.5A CN201911017564A CN112707834A CN 112707834 A CN112707834 A CN 112707834A CN 201911017564 A CN201911017564 A CN 201911017564A CN 112707834 A CN112707834 A CN 112707834A
Authority
CN
China
Prior art keywords
straight
alkylene
group
branched
single bond
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201911017564.5A
Other languages
Chinese (zh)
Other versions
CN112707834B (en
Inventor
张耀
段庆华
鱼鲲
李勇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Original Assignee
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sinopec Research Institute of Petroleum Processing, China Petroleum and Chemical Corp filed Critical Sinopec Research Institute of Petroleum Processing
Priority to CN201911017564.5A priority Critical patent/CN112707834B/en
Priority to US17/755,075 priority patent/US20230012456A1/en
Priority to PCT/CN2020/123197 priority patent/WO2021078249A1/en
Priority to EP20879644.1A priority patent/EP4049994A4/en
Publication of CN112707834A publication Critical patent/CN112707834A/en
Application granted granted Critical
Publication of CN112707834B publication Critical patent/CN112707834B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/10—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms cycloaliphatic
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
    • 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
    • C10M133/16—Amides; 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
    • C10M2215/02—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
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10M2215/02—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
    • 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
    • C10M2215/02—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
    • 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
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives

Landscapes

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

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, wherein the modified oil is prepared by mixing natural oil and alcohol or amine according to the weight ratio of 1: 0.1-5, and reacting at 50-200 deg.C for 1-20 hr, wherein the natural oil can 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 additive can improve the lubricating performance of oil products, the improvement space is large. 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 the 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 group being selected from (i + j) -valent C1-30A hydrocarbon group, a single bond (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably selected from (i + j) -valent C1-10Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C1-30Hydrocarbyl (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when i ═ j ═ 1, the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond);
each R group, equal to OR different from each other, is independently chosen from-OR ', -N (R')2Wherein each R' is independently selected from C1-10Straight or branched alkyl, H (preferably selected from C)1-6Straight or branched alkyl, H, more preferably selected from C1-3Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from single bond, C1-20Alkylene (preferably C)1-12Straight or branched chainAlkalkylene, more preferably C1-8Linear 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, C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Linear or branched alkylene);
each R is0The radicals, equal to or different from each other, are each independently selected from H, C1-10Hydrocarbyl (preferably C)1-6Straight or branched alkyl, more preferably C1-3Straight 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 G1Each independently selected from the group consisting of a single bond, — R4-and-OR4- (wherein R is4To the N atom), wherein R4Is C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Straight or branched alkylene) (each G)1The radicals are each independently preferably selected from the group consisting of a single bond, C1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each G2Each independently selected from a single bond, a,
Figure BDA0002246190470000032
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene radical, C7-15Alkylene aryl, more preferably selected from C1-12Straight or branched alkylene, C6-12Arylene radical, C7-12An alkylene aryl group;
each R is2Each independently selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L '-OH, more preferably H), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000033
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000034
more preferably H, C1-3Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000035
) Wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene), G2The radicals are selected from single bonds,
Figure BDA0002246190470000041
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene, more preferably selected from C1-12Straight or branched alkylene, C6-12An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3), R2The group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L' -OH, more preferably H), each R)3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000042
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH, more preferably selected from H, C1-3Straight or branched alkyl, -L '-OH), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene).
According to the invention, optionally, in formulae (II) and (III), each G1Each of the groups is independently preferably selected from single bonds; each G2Each independently selected from a single bond, C1-10Alkylene, -L' -OH; each R is3Each group is independently selected from H; each R is2Each independently selected from H, C1-6Straight or branched chain alkyl, -L' -OH.
According to the present invention, when i ═ j ═ 1, the structure of the ester compound is represented by formula (IV):
Figure BDA0002246190470000043
in formula (IV), the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear 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 the 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 C1-30A hydrocarbon group, a single bond (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C1-30Hydrocarbyl (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when i ═ j ═ 1, the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond);
each R group, equal to OR different from each other, is independently chosen from-OR ', -N (R')2Wherein each R' is independently selected from C1-10Straight or branched alkyl, H (preferably selected from C)1-6Straight or branched alkyl, H, more preferably selected from C1-3Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from single bond, C1-20Alkylene (preferably C)1-12Straight or branched alkylene, more preferably C1-8Linear 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, C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Linear or branched alkylene);
each R is0The radicals, equal to or different from each other, are each independently selected from H, C1-10Hydrocarbyl (preferably C)1-6Straight or branched alkyl, more preferably C1-3Straight 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,
Figure BDA0002246190470000133
Ethylene, propylene, and at least one a "group is selected from-CH ═ CH —;
in the formula (. beta.), G1The radicals being selected from single bonds, - (R)4-and-OR4- (wherein R is4To the N atom), wherein R4Is C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Straight or branched alkylene) (G)1The radicals are preferably selected from the group consisting of single bonds, C1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); g2The radicals are selected from single bonds,
Figure BDA0002246190470000141
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene radical, C7-15Alkylene aryl, more preferably selected from C1-12Straight or branched alkylene, C6-12Arylene radical, C7-12An alkylene aryl group;
R2the group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched chainAlkyl, -L '-OH, more preferably H), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000142
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000143
more preferably H, C1-3Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000144
) Wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene), G2The radicals are selected from single bonds,
Figure BDA0002246190470000145
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene, more preferably selected from C1-12Straight or branched alkylene, C6-12An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3)，R2The group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L' -OH, more preferably H), each R)3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure BDA0002246190470000146
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH, more preferably selected from H, C1-3Straight or branched alkyl, -L '-OH), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene);
the X group is selected from H.
According to the invention, optionally in the formula (. beta.), G1The radicals being selected from single bonds, G2The radicals being selected from single bonds, C1-10A hydrocarbylene group; each R is3Each independently selected from H, — L' -OH; r2The group is selected from H, C1-6Straight 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 C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear 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.
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 terms of-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 ℃, more preferably 30 to 100 ℃. The time of the epoxidation reaction is preferably as long as the epoxidation reaction proceeds smoothly, and generally, the longer the reaction time is, the more preferably 0.5 to 24 hours, and the more preferably 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 (α).
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)1Amount 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 0.5 to 24 hours, and more preferably 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, etc,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 and AlCl3One 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 or may not be 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, etc., 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 formula-CH2-A-CH3Wherein 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-CH2-CH3。
In the context of the present specification, the expression "number + valence + group" or the like refers to the base structure corresponding to the group from which it corresponds(e.g., a chain, a ring, a combination thereof, or the like) from which the number of hydrogen atoms represented by the number have been removed, preferably refers to a group obtained from a carbon atom (preferably a saturated carbon atom and/or a non-identical carbon atom) contained in the structure from which the number of hydrogen atoms represented by the number have been removed. For example, "3-valent straight or branched alkyl" refers to a group obtained by removing 3 hydrogen atoms from a straight or branched alkane (i.e., the base chain to which the straight or branched alkyl corresponds), and "2-valent straight or branched heteroalkyl" refers to a group obtained by removing 2 hydrogen atoms from a straight 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-CH2-CH2-CH2-*、
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 temperature is heated to 100 ℃, the reaction is continued for 7h under the condition of maintaining the temperature at 100 ℃, 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 in 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 by equimolar ethanol, and the ester compound D-2 is obtained.
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 (13)

1. An ester compound has a structure shown in formula (I):
Figure FDA0002246190460000011
in the 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 group being selected from (i + j) -valent C1-30A hydrocarbon group, a single bond (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably selected from (i + j) -valent C1-10Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C1-30Hydrocarbyl (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when i ═ j ═ 1, the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond);
each R group, equal to OR different from each other, is independently chosen from-OR ', -N (R')2Wherein each R' is independently selected from C1-10Straight or branched alkyl, H (preferably selected from C)1-6Straight or branched alkyl, H, more preferably selected from C1-3Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from single bond, C1-20Alkylene (preferably C)1-12Straight or branched alkylene, more preferably C1-8Linear 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, C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Linear or branched alkylene);
each R is0The radicals, equal to or different from each other, are each independently selected from H, C1-10Hydrocarbyl (preferably C)1-6Straight or branched alkyl, more preferably C1-3Straight 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) - (CH) -,
Figure FDA0002246190460000012
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 FDA0002246190460000021
in formulae (II) and (III), each G1Each independently selected from the group consisting of a single bond, — R4-and-OR4- (wherein R is4To the N atom), wherein R4Is C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Straight or branched alkylene) (each G)1The radicals are each independently preferably selected from the group consisting of a single bond, C1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each G2Each independently selected from a single bond, a,
Figure FDA0002246190460000022
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene radical, C7-15Alkylene aryl, more preferably selected from C1-12Straight or branched alkylene, C6-12Arylene radical, C7-12An alkylene aryl group;
each R is2Each independently selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L '-OH, more preferably H), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000023
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000024
more preferably H, C1-3Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000025
) Wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene), G2The radicals are selected from single bonds,
Figure FDA0002246190460000026
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene, more preferably selected from C1-12Straight or branched alkylene, C6-12An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3), R2The group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L' -OH, more preferably H), each R)3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000031
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH, more preferably selected from H, C1-3Straight or branched chain alkyl, -L '-OH), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene).
2. Esters according to claim 1, characterized in that in the formulae (II) and (III), each G is1Each group is independently selected from a single bond; each G2Each independently selected from a single bond, C1-10Alkylene, -L' -OH; each R is3Each group is independently selected from H; each R is2Each independently selected from H, C1-6Straight or branched chain alkyl, -L' -OH.
3. An ester compound according to claim 1, wherein i ═ j ═ 1, and the structure of the ester compound is represented by formula (IV):
Figure FDA0002246190460000032
in formula (IV), the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond).
4. An ester compound as claimed in claim 1, wherein the ester compound comprises one or more of the following compounds:
Figure FDA0002246190460000041
Figure FDA0002246190460000051
Figure FDA0002246190460000061
Figure FDA0002246190460000071
Figure FDA0002246190460000081
Figure FDA0002246190460000091
Figure FDA0002246190460000101
Figure FDA0002246190460000111
5. a process for producing an ester compound, comprising the steps of epoxidizing at least one ethylenic bond in a compound represented by the formula (alpha) and reacting the resultant product with a compound represented by the formula (beta),
Figure FDA0002246190460000121
in the 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 C1-30A hydrocarbon group, a single bond (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when one of i and j is greater than 1, the L group is selected from (i + j) -valent C1-30Hydrocarbyl (preferably selected from (i + j) -valent C1-20Straight or branched alkyl, more preferably C selected from (i + j valent)1-10Straight or branched chain alkyl); when i ═ j ═ 1, the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond);
each R group, equal to OR different from each other, is independently chosen from-OR ', -N (R')2Wherein each R' is independently selected from C1-10Straight or branched alkyl, H (preferably selected from C)1-6Straight or branched alkyl, H, more preferably selected from C1-3Straight or branched alkyl, H);
each R' group is the same or different from each other and is independently selected from the group consisting of a single bond, C1-20Alkylene (preferably C)1-12Straight or branched alkylene, more preferably C1-8Linear 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 single bond, C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Linear or branched alkylene);
each R is0The radicals, equal to or different from each other, are each independently selected from H, C1-10Hydrocarbyl (preferably C)1-6Straight or branched alkyl, more preferably C1-3Straight 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,
Figure FDA0002246190460000122
Ethylene, propylene, and at least one a' group is selected from-CH ═ CH —;
in the formula (. beta.), G1The radicals being selected from single bonds, - (R)4-and-OR4- (wherein R is4To the N atom), wherein R4Is C1-10Alkylene (preferably C)1-6Straight or branched alkylene, more preferably C1-3Straight or branched alkylene) (G)1The radicals are preferably selected from the group consisting of single bonds, C1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); g2The radicals are selected from single bonds,
Figure FDA0002246190460000123
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene radical, C7-15Alkylene aryl, more preferably selected from C1-12Straight or branched alkylene, C6-12Arylene radical, C7-12An alkylene aryl group;
R2the group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L '-OH, more preferably H), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene); n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3);
each R is3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000131
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000132
more preferably H, C1-3Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000133
) Wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene), G2The radicals are selected from single bonds,
Figure FDA0002246190460000134
And C1-10Alkylene (preferably selected from single bond, C)1-6Straight or branched alkylene, more preferably selected from the group consisting of a single bond, C1-3Linear or branched alkylene); each R is1Each independently selected from C1-18Alkylene (preferably selected from C)1-15Straight or branched alkylene, C6-15Arylene, more preferably selected from C1-12Straight or branched alkylene, C6-12An arylene group; n is an integer of 0 to 10 (preferably an integer of 1 to 6, more preferably 1, 2 or 3), R2The group is selected from H, C1-6Straight or branched alkyl, -L' -OH (preferably selected from H, C)1-3Straight or branched alkyl, -L' -OH, more preferably H), each R)3Each independently selected from H, C1-10Straight or branched alkyl, -L' -OH and
Figure FDA0002246190460000135
(preferably selected from H, C1-6Straight or branched alkyl, -L' -OH, more preferably selected from H, C1-3Straight or branched chain alkyl, -L '-OH), wherein the L' group is selected from C1-10Alkylene (preferably selected from C)1-10Straight or branched alkylene, C3-10Cycloalkylene radical, C6-10Arylene radical, C7-10Alkylene aryl, more preferably selected from C1-6Straight or branched alkylene, C4-8Cycloalkylene radical, C6-8Arylene);
the X group is selected from H.
6. The process according to claim 5, wherein in the formula (β), G1The radicals being selected from single bonds, G2The radicals being selected from single bonds, C1-10A hydrocarbylene group; each R is3Each independently selected from H,
—L'—OH；R2The group is selected from H, C1-6Straight or branched chain alkyl, -L' -OH.
7. The process according to claim 5, wherein i ═ j ═ 1, and the compound represented by formula (α) has a structure represented by formula (γ):
Figure FDA0002246190460000141
in formula (. gamma.), the L group is selected from C1-30Alkylene, single bond (preferably selected from C)1-20Straight or branched alkylene, single bond, more preferably selected from C1-10Linear or branched alkylene, single bond).
8. The process according to claim 5, wherein the compound of formula (α) is selected from one or more of the following compounds, or a condensation product of these compounds with each other or with 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, undecenoic acid amide, decenoic acid amide, octenoic;
or the compound shown in the formula (beta) is selected from one or more of the following 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.
9. The process according to claim 5, wherein the compound of formula (α) is epoxidated with an oxidizing agent (preferably comprising an organic peroxide and/or an inorganic peroxide).
10. A process according to claim 5, wherein the epoxidation product of the compound of formula (α) (in terms of epoxy groups) is reacted with a compound of formula (β) (in terms of X-G)1Amount of-N) is 1: 0.1 to 10 (preferably 1: 0.2 to 5); the reaction temperature is 20-200 ℃ (preferably 40-150 ℃).
11. The process according to claim 5, wherein a catalyst (which may be an inorganic acid, an organic acid, a solid acid, a heteropoly acid, an acidic ionic liquid, an acidic resin, an acidic molecular sieve, an inorganic base, an organic base, a metal chloride, or a metal oxide) 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)One or more of the above-mentioned substances may be selected from sulfuric acid, perchloric acid, p-toluenesulfonic acid, acidic resins, phosphotungstic heteropoly acid, acidic ionic liquids, acidic molecular sieves, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium propoxide, sodium propoxide, AlCl3One or more of tin chloride, n-butyltin oxide, and dibutyltin oxide).
12. The ester compound of any one of claims 1 to 4 or the ester compound obtained by the method of any one of claims 5 to 11 is used as an antiwear agent and/or a friction reducing agent (preferably as an antiwear agent and/or a friction reducing agent for petroleum products, more preferably as an antiwear agent and/or a friction reducing agent for lubricating grease).
13. A lubricating oil composition comprising the ester compound according to any one of claims 1 to 4 or the ester compound obtained by the method according to any one of claims 5 to 11, and a lubricating oil base oil.
CN201911017564.5A 2019-10-24 2019-10-24 Ester compound and preparation method and application thereof Active CN112707834B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201911017564.5A CN112707834B (en) 2019-10-24 2019-10-24 Ester compound and preparation method and application thereof
US17/755,075 US20230012456A1 (en) 2019-10-24 2020-10-23 Ester compound and preparation method therefor and uses thereof
PCT/CN2020/123197 WO2021078249A1 (en) 2019-10-24 2020-10-23 Ester compound and preparation method therefor and uses thereof
EP20879644.1A EP4049994A4 (en) 2019-10-24 2020-10-23 Ester compound and preparation method therefor and uses thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911017564.5A CN112707834B (en) 2019-10-24 2019-10-24 Ester compound and preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN112707834A true CN112707834A (en) 2021-04-27
CN112707834B CN112707834B (en) 2022-10-21

Family

ID=75541472

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911017564.5A Active CN112707834B (en) 2019-10-24 2019-10-24 Ester compound and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN112707834B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115404118A (en) * 2022-09-16 2022-11-29 季华实验室 Aluminum shell stretching oil composition
CN116462600A (en) * 2023-04-23 2023-07-21 安徽农业大学 Multifunctional aliphatic long-chain diester, preparation method, application and prepared functional polyamide thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8841470B1 (en) * 2010-08-26 2014-09-23 The United States Of America, As Represented By The Secretary Of Agriculture Process for preparation of nitrogen-containing vegetable oil-based lubricant additive

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8841470B1 (en) * 2010-08-26 2014-09-23 The United States Of America, As Represented By The Secretary Of Agriculture Process for preparation of nitrogen-containing vegetable oil-based lubricant additive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JÜRGEN O. METZGER等: "Synthesis of New Heterocyclic Fatty Compounds", 《EUR. J. ORG. CHEM.》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115404118A (en) * 2022-09-16 2022-11-29 季华实验室 Aluminum shell stretching oil composition
CN116462600A (en) * 2023-04-23 2023-07-21 安徽农业大学 Multifunctional aliphatic long-chain diester, preparation method, application and prepared functional polyamide thereof
CN116462600B (en) * 2023-04-23 2024-05-28 安徽农业大学 Multifunctional aliphatic long-chain diester, preparation method, application and prepared functional polyamide thereof

Also Published As

Publication number Publication date
CN112707834B (en) 2022-10-21

Similar Documents

Publication Publication Date Title
CN1028874C (en) High molecular weight nitrogen-containing condensates and fuel and lubricants containing same
RU2485171C2 (en) Functional fluids for internal combustion engines
JP5207468B2 (en) Fuel additive
RU2499034C2 (en) Poly(hydroxycarboxylic acid) amide salt derivative and lubricant composition containing said derivative
CN112707834B (en) Ester compound and preparation method and application thereof
EP1788067B1 (en) Lubricant formulations for providing friction modification
CN1871329A (en) Fatty acid esters and uses thereof
SK155398A3 (en) Process for preparing polyalkene amines
JP2002539321A (en) Oil-soluble molybdenum polyfunctional friction reducer additive for lubricating compositions
US9719027B2 (en) Low viscosity metal-based hydrogen sulfide scavengers
CN112707820B (en) Ester compound and preparation method and application thereof
CN1252089A (en) Friction reducing additives for fuels and lubricants
CN1102668A (en) High molecular weight nitrogen-containing condensates and fuels and lubricants containing same
DE102007047229B4 (en) Branched succinimide dispersant compounds and methods of preparing the compounds
CN108018092B (en) Composition with diesel anti-wear properties, diesel composition and preparation method thereof
EP4049994A1 (en) Ester compound and preparation method therefor and uses thereof
CN1041433C (en) Additive concentrates
CN112707817B (en) Ester compound and preparation method and application thereof
US10577542B2 (en) Low viscosity metal-based hydrogen sulfide scavengers
KR102125974B1 (en) Pyran dispersants
CN108003950B (en) Composition with diesel anti-wear properties, diesel composition and preparation method thereof
CN1132912C (en) Suspension bed hydrogenation process for refining heavy and residual oil mixed with waste oil
EP2935543A1 (en) A post-treated molybdenum imide additive composition, methods of making same and lubricating oil compositions containing same
CN108018100B (en) Composition with diesel anti-wear properties, diesel composition and preparation method thereof
CN113861031A (en) Ester compound, preparation method and application thereof, and lubricating oil composition

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant