Organomolybdenum compounds, process for their preparation, use thereof

Abstract

The application provides an organic molybdenum compound, a preparation method and application thereof. The structure of the organic molybdenum compound is shown in formula (I): wherein definitions of the groups are shown in the specification. The organic molybdenum compound has excellent anti-wear and anti-friction performance and oxidation resistance.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic molybdenum compound and a preparation method and use thereof, in particular to a sulfur-free and phosphorus-free organic molybdenum compound and a preparation method and use thereof. BACKGROUND

[0002] In the lubrication process, the oil-soluble organic molybdenum can decompose to generate ultra-fine molybdenum disulfide, which adheres to the surface of the friction pair, fills the rough surface and increases the lubrication, thereby reducing the friction coefficient. With the increasing requirement of environmental protection, the requirement for oil-soluble lubricating oil additives is also increasing. The additive with high phosphorus content can poison the automobile exhaust catalyst, and the additive with a large amount of sulfur can pollute the environment. Therefore, the new type of organic molybdenum without P and S, the oil-soluble molybdenum amine complex additive is widely used in high-grade internal combustion engine oil, which can meet the increasingly stringent energy-saving and environmental protection requirements.

[0003] US 5,137,647 discloses an organic molybdenum lubricating oil additive prepared by reacting a fatty oil or acid, 2-(2-aminoethyl) aminoethanol and an inorganic molybdenum compound, which has the properties of anti-wear and friction reduction, oxidation resistance, etc. US 5,412,130 discloses a method for preparing an organic molybdenum lubricating oil additive by reacting a diol, a diamine, a thiol and an aminoethanol with an inorganic molybdenum compound. Patent ZL200610008072.6 discloses an organic molybdenum additive prepared by reacting p-hydroxybenzyl acid polyol ester, an inorganic molybdenum compound and a fatty amine, an aromatic amine, an amide or a mixture thereof. CN102796592B discloses an organic molybdenum additive prepared by reacting an aliphatic amide, a polyisobutylene succinimide and an inorganic molybdenum compound.

[0004] At present, the sulfur-free and phosphorus-free organic molybdenum has good anti-wear and friction reduction performance, but its oxidation resistance performance still has a large space for improvement. In addition, the trend of additive technology development is multifunctionalization. The development of multifunctional additives can improve the performance of the additives, reduce the variety and amount of additives in the formula system, improve the formula applicability, and is conducive to meeting the requirements of energy saving and environmental protection. SUMMARY

[0005] The purpose of the present application is to provide a sulfur-free and phosphorus-free organic molybdenum compound and a preparation method and use thereof, which has excellent anti-wear and friction reduction performance and oxidation resistance performance.

[0006] The organic molybdenum compound of the present application has the structure as shown in formula (I):

[0007]

[0008] In formula (I), there are a number of repeating units L and b number of molybdenum-containing groups, each A' group in the b number of molybdenum-containing groups represents a binding end to the a number of L groups, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), the a number of L groups are identical to or different from each other and are each independently selected from the group of radicals represented by formula (II);

[0009]

[0010] In formula (II), HO is bound to the phenyl ring (HO is preferably located in the meta position of the chain on which R1 is located); y number of R groups are bound to the phenyl ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 linear or branched alkyl (preferably each independently selected from H and C 1-4 linear or branched alkyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R1 is each independently selected from a single bond and C 1-20 linear or branched alkylene (preferably selected from a single bond and C 1-4 linear or branched alkylene); R2 in the n number of repeating units are identical to or different from each other and are each independently selected from a single bond and C 1-20 linear or branched alkylene (preferably each independently selected from a single bond and C 1-4 linear or branched alkylene); R3 is selected from H and C 1-20 linear or branched alkyl (preferably selected from H and C 1-4 linear or branched alkyl); a group represented by formula (III) and a group represented by formula (IV),

[0011]

[0012] the R4 groups are each independently selected from H and C 1-20 linear or branched alkyl (preferably selected from H and C 1-4 linear or branched alkyl);

[0013] m is an integer between 0 and 10 (preferably an integer between 1 and 5); the G1 group is a binding end to the molybdenum-containing group or H; the G2 group is a binding end to the molybdenum-containing group, a binding end to another L group other than the L group on which it is located, H, the R5 groups are each independently selected from C 1-20 linear or branched alkylene (preferably each independently selected from C 1-4 linear or branched alkylene), the R6 groups are selected from H, C 1-20 linear or branched alkyl (preferably each independently selected from H, C1-4 linear or branched alkyl group) ;

[0014] G3is a binding end to other L groups than the L group it is in, H;

[0015] In the a L groups, at least one A group is selected from the group represented by formula (III) ;

[0016] In the a L groups, the sum of the number of G1groups and G2groups which are binding ends to the molybdenum-containing group is 2b;

[0017] In the two groups which are binding ends to the same molybdenum-containing group, at least one G2group is bonded thereto.

[0018] According to the present application, the two binding ends to formula (II) in formula (III) or formula (IV) can be bonded to the groups in formula (II) in any manner, for example, can be bonded to formula (II) in one direction, or can be bonded to formula (II) in the opposite direction.

[0019] According to the present application, examples of the organic molybdenum compound that can be cited include one or more of the following structural compounds:

[0020]

[0021]

[0022]

[0023] According to the present application, the method for producing the organic molybdenum compound includes the following steps:

[0024] (1) reacting a compound represented by formula (X) with a peroxide;

[0025]

[0026] In formula (X), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R1is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); each R group is independently selected from H and C 1-20 linear or branched alkyl group (preferably each is independently selected from H and C 1-4 linear or branched alkyl group); n is an integer between 1 and 10 (preferably an integer between 1 and 3); each R1is independently selected from a single bond and C 1-20 linear or branched alkylene group (preferably selected from a single bond and C 1-4 linear or branched alkylene group); R2in the n repeating units are the same or different from each other, and each is independently selected from a single bond and C 1-20straight-chain or branched alkylene (preferably each independently selected from the group consisting of a single bond and C 1-4 straight-chain or branched alkylene) ; R3is selected from the group consisting of H and C 1-20 straight-chain or branched alkyl (preferably selected from the group consisting of H and C 1-4 straight-chain or branched alkyl) ; A" in n repeating units is the same or different from each other, and is each independently selected from the group consisting of a single bond, wherein the R4groups are each independently selected from the group consisting of H and C 1-20 straight-chain or branched alkyl (preferably selected from the group consisting of H and C 1-4 straight-chain or branched alkyl) ; at least one A" in formula (X) is

[0027] (2) reacting the reaction product of step (1) with a compound represented by formula (Y) ;

[0028]

[0029] in formula (Y), R I groups are each independently selected from the group consisting of C 1-20 straight-chain or branched alkylene (preferably each independently selected from the group consisting of C 1-4 straight-chain or branched alkylene), R II groups are each independently selected from the group consisting of H, C 1-20 straight-chain or branched alkyl; m is an integer between 0 and 10 (preferably an integer between 1 and 5) ;

[0030] (3) reacting the reaction product of step (2) with an inorganic molybdenum compound, and collecting the product.

[0031] According to the present application, in step (1), the compound represented by formula (X) can be selected from cardanol, alkylated cardanol, which can be obtained by reacting cardanol with an alkylating agent, for example, t-butylated cardanol can be obtained by reacting cardanol with t-butyl chloride.

[0032] According to the present application, in step (1), the peroxide is preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid, peroxy sulfonic acid, meta-chloro peroxy benzoic acid, t-butyl hydroperoxide, t-butyl peroxy acetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide, more preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid and peroxy sulfonic acid.

[0033] According to the present application, in step (2), the compound represented by formula (Y) can be selected from polyene polyamines, for example, one or more of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine.

[0034] According to the present application, in step (3), the inorganic molybdenum compound can be selected from one or more of molybdic acid, ammonium molybdate, ammonium dimolybdate, molybdenum trioxide and sodium molybdate.

[0035] According to the present application, the equivalent ratio between the compound of formula (X) and the peroxide, the compound of formula (Y), the inorganic molybdenum compound is preferably 1:0.5-10:0.5-10:0.5-5, more preferably 1:2-3:2-3:1-2.

[0036] According to the present application, the reaction temperature of step (1) is preferably 0-100°C, more preferably 20-80°C; the reaction temperature of step (2) is preferably 50-150°C, more preferably 70-100°C; the reaction temperature of step (3) is preferably 80-200°C, more preferably 120-160°C.

[0037] According to the present application, the reaction time of step (1), step (2) and step (3) is generally longer the better, in general, the reaction time of step (1) is preferably 1-10h, more preferably 3-5h; the reaction time of step (2) is preferably 1-10h, more preferably 2-4h; the reaction time of step (3) is preferably 1-10h, more preferably 3-5h.

[0038] According to the present application, in step (3), a polyisobutylene succinimide can be added in the reaction between the reaction product of step (2) and the inorganic molybdenum compound, the molecular weight of the polyisobutylene part of the polyisobutylene succinimide is preferably 500-4000, more preferably 700-3000, further preferably 1000-2400; the mass ratio between the polyisobutylene succinimide and the inorganic molybdenum compound is preferably 1:0.01-1, more preferably 1:0.1-0.5. The polyisobutylene succinimide can be selected from one or more of T151, T152, T153, T154 and T161 produced by Suzhou Special Oil Factory, Jinzhou Petrochemical Branch Additive Factory, Wuxi South Additive Factory.

[0039] According to the present application, the reaction step (1), (2) or (3) can be carried out in the presence of a diluent and / or a solvent, or can be carried out without using a diluent and / or a solvent.

[0040] According to the present application, the diluent can be selected from one or more of API I, II, III, IV and V base oils, common commercial products or brands include 150SN, 200SN, 350SN, 500SN, 650SN, 150BS, HVI-100, HVI-150, HVI-200, HVI-350, HVI-400, HVI-500, HVI-150BS, PAO4, PAO6, PAO8, PAO10, alkylbenzene, alkylnaphthalene, etc.

[0041] According to the present application, the solvent can be selected from C 6-20 aromatic hydrocarbons (such as benzene, toluene, xylene and cumene), C 6-10 alkanes (such as n-hexane, cyclohexane and petroleum ether), solvent naphtha and the like. These solvents can be used singly or in combination of two or more. The solvent can be removed after the reaction is completed using a method known to those skilled in the art, for example, under normal or reduced pressure.

[0042] According to a particular embodiment of the present application, the diluent and / or solvent can be added at any stage of the reaction step in an amount according to the conventional use in the art, and is not particularly limited.

[0043] According to the present application, it is apparent that the reaction step is generally carried out under the protection of an inert gas atmosphere. As the inert gas, for example, nitrogen and argon and the like can be mentioned, and is not particularly limited.

[0044] According to the present application, in step (3), a promoter for promoting the completion of the reaction can be added, and common promoters include water, ethanol, propanol, butanol, aqueous ammonia and the like. If a promoter is added, it can be removed after the reaction is completed using a method known to those skilled in the art, for example, under normal or reduced pressure.

[0045] According to the present application, by the aforementioned method for producing an organic molybdenum compound, as the reaction product, a single kind of organic molybdenum compound can be produced, or a mixture of a plurality of kinds of organic molybdenum compounds can be produced, or a mixture of one or more kinds of the organic molybdenum compound and the aforementioned diluent (if used) can be produced. These reaction products are all intended by the present application, and the difference in the form of existence thereof does not affect the realization of the effect of the present application. Therefore, these reaction products are collectively referred to as an organic molybdenum compound without distinction in the context of the present specification. In view of this, according to the present application, there is no absolute necessity to further purify the reaction product, or to further separate a specific structure of an organic molybdenum compound from the reaction product. Of course, the purification or separation is preferred for the further enhancement of the intended effect of the present application, but is not essential to the present application. Nevertheless, as the method for the purification or separation, for example, a method of purifying or separating the reaction product by column chromatography or preparative chromatography and the like can be mentioned.

[0046] The organic molybdenum compound of the present application can be used as an anti-wear agent, a friction-reducing agent, an antioxidant for lubricating oil.

[0047] The method for producing an organic molybdenum compound of the present application is simple in steps and high in conversion rate in the reaction process. The organic molybdenum compound of the present application has excellent anti-wear and friction-reducing properties and antioxidant properties. BRIEF DESCRIPTION OF DRAWINGS

[0048] Figure 1 IR of the product of Example 2. DETAILED DESCRIPTION

[0049] In 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 -CH2-A-CH3, wherein group A is defined as being selected from the group consisting of a single bond and a methyl group. In view of this, if A is a single bond, then it means that group A is absent, in which case the structural formula is correspondingly simplified to -CH2-CH3.

[0050] The application will be further described in the following examples without limiting the application thereto.

[0051] The raw materials used are as follows:

[0052] Cardanol, Shanghai Wu-Jing Chemical Co., Ltd., technical product

[0053] Zinc chloride, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0054] Concentrated sulfuric acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0055] Hydrogen peroxide (30%), National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0056] Formic acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0057] Ammonium molybdate, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0058] Molybdenum trioxide, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0059] Tert-butyl chloride, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0060] Antioxidant T501, Xingpu Company of Research Institute of Petroleum Processing, technical product

[0061] Antioxidant T512, Xingpu Company of Research Institute of Petroleum Processing, technical product

[0062] Polyisobutylene succinimide T151, Wuxi Nanfang Additive Factory, technical product

[0063] Polyisobutylene succinimide T153, Wuxi Nanfang Additive Factory, technical product

[0064] Polyisobutylene succinimide T161, Wuxi Nanfang Additive Factory, technical product

[0065] Oleic acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0066] N-(2-hydroxyethyl)ethylenediamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0067] Acetone, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0068] Xylene, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0069] Diethylenetriamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0070] Diisooctyl sebacate, Beijing Chemical Factory No. 3, industrial product

[0071] The inorganic molybdenum compound selected in the embodiment of the present application includes:

[0072] C-1: ammonium molybdate, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0073] C-2: molybdenum trioxide, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0074] The diluent selected in the embodiment of the present application includes:

[0075] D-1: 150SN, Dalian Petrochemical

[0076] D-2: alkyl benzene, Nanjing Alkyl Benzene Factory

[0077] D-3: alkyl naphthalene, ExxonMobil

[0078] Preparation of t-butylated amino cardanol in Example 1

[0079] Take 100 g of cardanol, 8 g of formic acid, 0.3 g of sulfuric acid, and 200 g of hydrogen peroxide, and add them to a three-necked flask with mechanical stirring, a reflux condenser, and temperature control, and then start stirring and heating. Maintain the reaction temperature at 70°C, and react for 3 hours. After the reaction is completed, cool down, and obtain a transparent brown-red liquid. Filter the reaction product, wash it with a 5% KOH solution, then wash it with distilled water until it is neutral, and then distill the organic phase under reduced pressure at 100 Pa and 150°C for 1 h to remove water and unreacted raw materials, and obtain transparent orange-red liquid epoxidized cardanol.

[0080] The 35 g epoxidized cardanol was dissolved in 100 ml acetone, and then the solution was put into a 250 ml three-necked flask, 0.9 g zinc chloride catalyst was added, and the stirring and heating were started. The reaction temperature was maintained at 60 °C, 9.5 g t-butyl chloride was slowly added dropwise into the flask, and the reaction was continued for 3 hours after the dropwise addition was completed. After the reaction was finished, the temperature was lowered, and a brownish red transparent liquid was obtained. The reaction product was filtered, washed with 5% KOH solution, and then washed with distilled water until neutral. The solvent, water and unreacted raw materials were removed by distillation under reduced pressure at 1000 Pa and 120 °C for 1 hour, and a brownish red viscous liquid t-butylated epoxidized cardanol was obtained.

[0081] The 32 g t-butylated epoxidized cardanol, 6 g diethylenetriamine and 90 g m-xylene were put into a 250 ml three-necked flask, and heated with stirring. The reaction was continued for 3 hours at 90 °C. After the reaction was finished, the solvent and unreacted raw materials were removed by distillation under reduced pressure for 1 hour, and a dark brownish red viscous liquid t-butylated aminocardanol was obtained.

[0082] The example reaction formula of the above reaction is shown in the following formula.

[0083]

[0084] Example 2

[0085] The 22 g t-butylated aminocardanol prepared in Example 1, 13 g polyisobutylene succinimide, 6.5 g ammonium molybdate, 8 g distilled water, 10 g 150SN and 70 g xylene were put into a reaction vessel, and stirred and heated to remove water. The reaction was continued for 4 hours at 140 °C, and finally filtered and distilled to remove the solvent, and an organic molybdenum additive W-01 was obtained, which had a molybdenum content of 5.5% by mass.

[0086] The example reaction formula of the above reaction is shown in the following formula.

[0087]

[0088] The product prepared in Example 2 was subjected to infrared spectrum analysis, and the infrared spectrum chart is shown in Figure 1 , and the analysis results are shown in Table 1.

[0089] Table 1 Infrared analysis results of the product

[0090]

[0091] In Table 1, it can be shown that the synthesized product is the target compound, because the characteristic peaks of C-OH stretching vibration peak, C-NH stretching vibration peak, benzene ring skeleton stretching vibration peak, N-C stretching vibration peak, O-C stretching vibration peak and Mo=O stretching vibration peak exist in the product.

[0092] Example 3-4

[0093] According to the reaction raw materials and reaction conditions in Table 2, the tert-butylated aminyl cardanol, polyisobutylene succinimide, inorganic molybdenum compound, distilled water, diluent and solvent prepared in Example 1 were added into a reaction vessel, stirred, heated, removed water, reacted at 120-160℃ for 1-10 hours, finally filtered, and distilled off the solvent to obtain organic molybdenum additives W-02-W-03, respectively, with the mass fraction of molybdenum content of 9.3%, 8.4%, respectively.

[0094] Comparative Example 1

[0095] The condensation product of oleic acid and N-(2-hydroxyethyl)ethylenediamine in a molar ratio of 1:1 was prepared by reacting at 120℃ for 5 hours, and was named as oleic acid amide.

[0096] According to the reaction raw materials and reaction conditions in Table 2, the oleic acid amide, inorganic molybdenum compound, distilled water, diluent and solvent were added into a reaction vessel, stirred, heated, removed water, reacted at 140℃ for 4 hours, cooled and filtered, and finally filtered and distilled off the solvent to obtain comparative organic molybdenum additive V-01 with the mass fraction of molybdenum content of 5.5%.

[0097] Table 2

[0098]

[0099] Example 5

[0100] W-01, W-02, W-03, V-01 and Vanderbilt 855 (with the mass fraction of molybdenum content of 6.6%) were added into diisooctyl sebacate base oil at a dosage of 0.5% (the mass of the added additive was 0.5% of the total mass of the prepared oil), and the anti-wear and friction-reducing properties were determined. The test conditions of the SRV anti-wear and friction-reducing evaluation experiment were: temperature 30℃, load 100N, stroke 1mm, test time 1 hour, and frequency 50Hz. The SRV method was in accordance with the national standard NB / SH / T 0847-2010. The measurement results are shown in Table 3.

[0101] Table 3 SRV test results of the organic molybdenum compounds of the application and the comparative organic molybdenum compounds

[0102] Number Organomolybdenum additive class Abrasion diameter / mm Friction coefficient 1 — 0.69 0.121 2 W-01 0.46 0.115 3 W-02 0.41 0.109 4 W-03 0.45 0.111 5 V-01 0.50 0.116 6 855 0.59 0.119

[0103] As can be seen from the test results in Table 3, the organic molybdenum compounds of the application have lower friction coefficient and wear scar diameter than the comparative organic molybdenum compounds, indicating that the organic molybdenum compounds of the application have better anti-wear and friction-reducing properties.

[0104] Example 6

[0105] W-01, W-02, W-03, V-01, 855 of Vanderbilt Company and hindered phenolic antioxidant T501, T512 were added into diisooctyl sebacate base oil respectively at a dosage of 0.5% (the mass of the evaluated additive is 0.5% of the total mass of the prepared oil), and antioxidation performance test was conducted, and the test instrument was TA5000 model DSC of TA Company, and the test condition was: 190℃, oxygen pressure 0.5MPa, and the temperature rising speed was 10℃ / min, and the test result is shown in Table 4.

[0106] It can be known by comparison that the organic molybdenum compound of the application significantly improves the oxidation induction period.

[0107] Table 4: Antioxidation test result

[0108] Evaluation sample Oxidation induction period / min W-01 30.0 W-02 38.6 W-03 32.3 V-01 17.1 855 13.0 T501 16.5 T512 13.0

Claims

1. An organomolybdenum compound, which is one or more of the following compounds:

2. A method for producing the organomolybdenum compound according to claim 1, comprising the steps of: (1) reacting a compound (X) with a peroxide; the compound (X) is selected from the group consisting of cardanol and / or alkylated cardanol; (2) reacting the reaction product of step (1) with a compound (Y); the compound (Y) is selected from the group consisting of polyene polyamine; (3) reacting the reaction product of step (2) with an inorganic molybdenum compound, and collecting the product.

3. The production process according to claim 2, characterized in that, In step (1), the peroxide is one or more of the group consisting of hydrogen peroxide, peroxyformic acid, peroxyacetic acid, peroxy sulfonic acid, meta-chloro peroxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peroxyacetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide.

4. The production process according to claim 2, characterized in that, In step (2), the compound (Y) is one or more of the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine.

5. The production process according to claim 2, characterized in that, In step (3), the inorganic molybdenum compound is one or more of the group consisting of molybdic acid, ammonium molybdate, ammonium paramolybdate, molybdenum trioxide and sodium molybdate.

6. The production process according to claim 2, characterized in that, The equivalent ratio between the compound (X), the peroxide, the compound (Y) and the inorganic molybdenum compound is 1:0.5-10:0.5-10:0.5-5.

7. The production process according to claim 2, characterized in that, The equivalent ratio between the compound (X), the peroxide, the compound (Y) and the inorganic molybdenum compound is 1:2-3:2-3:1-2.

8. The production process according to claim 2, characterized in that, The reaction temperature of step (1) is 0-100°C; the reaction temperature of step (2) is 50-150°C; and the reaction temperature of step (3) is 80-200°C.

9. The production process according to claim 2, characterized in that, The reaction temperature of step (1) is 20-80°C; the reaction temperature of step (2) is 70-100°C; and the reaction temperature of step (3) is 120-160°C.

10. The production process according to claim 2, characterized in that, In step (3), a polyisobutylene succinimide is added to the reaction of the reaction product of step (2) with the inorganic molybdenum compound.

11. The production process according to claim 10, characterized in that, In step (3), the mass ratio between the polyisobutylene succinimide and the inorganic molybdenum compound is 1:0.01-1.

12. The organomolybdenum compound according to claim 1 and the organomolybdenum compound produced by the method according to any one of claims 2 to 11 for use as an anti-wear agent, a friction-reducing agent, an antioxidant for lubricating oil.

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