Organophosphorus compounds, processes for their preparation, uses thereof

Abstract

The application provides an organic phosphorus compound, a preparation method and application thereof. The structure of the organic phosphorus compound is shown in the following formula (I): wherein at least one A group is selected from a group shown in the following formula (II), a group shown in the following formula (III) or a group shown in the following formula (IV); wherein the definitions of the groups are shown in the description. The organic phosphorus compound has excellent anti-oxidation, anti-wear and friction-reducing performances. The preparation method of the organic phosphorus compound has simple steps and high conversion rate.

Description

Technical Field

[0001] This invention relates to an organophosphorus compound, and more particularly to a sulfur-free organophosphorus compound, its preparation method, and its uses. Background Technology

[0002] Lubricating oil can perform its lubricating function under fluid lubrication conditions due to its own viscosity. However, under mixed lubrication conditions, the viscosity of the lubricating oil alone is insufficient to meet lubrication requirements. In this case, anti-wear agents need to be added to improve the anti-wear and friction-reducing capabilities of the lubricating oil. Anti-wear agents can be adsorbed onto metal surfaces or react with metal surfaces to form adsorption or reaction films, preventing scratches or even welding on metal surfaces. They are used to improve the lubricity and anti-wear properties of oils. These agents mainly include high-viscosity ester anti-wear agents, phosphorus-containing anti-wear agents, nitrogen-containing anti-wear agents, metal salt anti-wear agents, boron-containing anti-wear agents, etc. Among them, phosphorus-containing anti-wear agents are widely used due to their high stability and good compatibility.

[0003] Currently, widely used anti-wear agents in the lubricating oil field include tricresyl phosphate (T306), acid phosphate (T304), and ammonium phosphate (IRGALUBE 349), but their anti-wear and friction-reducing properties need further improvement. For example, CN102260572B discloses a phosphorus-nitrogen type anti-wear agent with good antioxidant, rust-preventive, and corrosion-preventive properties, as well as good anti-wear properties. It can be used as a multifunctional additive for hydraulic oil, gear oil, and various industrial lubricating greases. However, it is only used as a supplement to sulfur-phosphorus composite anti-wear agents and does not show outstanding anti-wear performance.

[0004] Currently, ashless phosphorus-containing additives exhibit good anti-wear and friction-reducing properties, but lack strong antioxidant properties. The trend in additive technology development is towards multifunctionality. Developing multifunctional additives can improve additive performance, reduce the variety and amount of additives in the formulation system, improve formulation applicability, and help meet energy conservation and environmental protection requirements. Summary of the Invention

[0005] This invention proposes an organophosphorus compound, its preparation method, and its uses.

[0006] The organophosphorus compound of the present invention has the structure shown in formula (I):

[0007]

[0008] In formula (I), HO is bonded to the benzene ring; y R groups are bonded to the benzene ring; y is selected from integers between 0 and 4; and each R group is independently selected from H and C. 1-10 Straight-chain or branched alkyl groups; n is an integer between 1 and 10; R1 is independently selected from C 1-20 A straight-chain or branched alkylene group; the R2s in the n repeating units may be the same or different from each other, and each is independently selected from C.1-20 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-20 Straight-chain or branched alkyl; the A groups in the n repeating units may be the same or different from each other, and each is independently selected from... The groups shown, the groups shown in formula (III) and the groups shown in formula (IV) include at least one A group selected from the group shown in formula (II), the group shown in formula (III) or the group shown in formula (IV);

[0009]

[0010] The R4 groups are each independently selected from H and C. 1-20 Straight-chain or branched alkyl groups;

[0011] The R0 groups are each independently selected from R5 and OR5, wherein the R5 groups are selected from H and C. 1-20 Straight-chain or branched alkyl groups and C 6-18 aryl, wherein the aryl group is optionally coated with one or more C 1-4 The R5 group may be substituted with a straight-chain or branched alkyl group, and may be optionally substituted with one or more halogens or hydroxyl groups.

[0012] In equations (II), (III), and (IV), * represents the junction with equation (I);

[0013] Each of the G1 groups is independently selected from R6, OR6, and the bonding end of the group of formula (I'), wherein the R6 group is selected from H, C 1-20 Straight-chain or branched alkyl groups and C 6-18 aryl, wherein the aryl group is optionally coated with one or more C 1-4 The R6 group may be substituted with a straight-chain or branched alkyl group, and may optionally be substituted with one or more halogens or one or more hydroxyl groups.

[0014]

[0015] The definitions of HO, R, y, R1, R2, R3, and n in equation (I') are the same as in equation (I);

[0016] The A' group in formula (I') is selected from The groups shown, the groups shown in formula (III), the groups shown in formula (IV), the groups shown in formula (III'), and the groups shown in formula (IV')

[0017]

[0018] The definition of the R0 group in formula (IV') is the same as that in formulas (II), (III) and (IV); the * in formulas (III') and (IV') represents the bonding end with formula (I'); the △ in formulas (III') and (IV') represents the bonding end bonded to formula (I) or the bonding end bonded to a group in formula (I') other than the group it contains; the △ in formulas (III') and (IV') do not bond to each other;

[0019] The G1' groups are each independently selected from R6, OR6, and the Δ-bonded ends of formula (I') groups other than the group they belong to, where the R6 group is selected from H, C 1-20 Straight-chain or branched alkyl groups and C 6-18 aryl, wherein the aryl group is optionally coated with one or more C 1-4 The R6 group may be substituted with a straight-chain or branched alkyl group, and may optionally be substituted with one or more halogens or hydroxyl groups.

[0020] According to the present invention, the R5 and R6 groups can each be independently selected from methyl, ethyl, hydroxymethyl, chloromethyl, and phenyl, for example, the R5 group is selected from methyl or ethyl, and the R6 group is selected from phenyl.

[0021] According to the present invention, preferably, in formulas (I) and (I'), HO is located at the meta position on the chain containing R1 on the benzene ring, y is an integer between 1 and 3, y R groups are located at the para or ortho position on the chain containing R1 on the benzene ring, and the R groups are selected from C 1-4 Straight-chain or branched alkyl groups, n being an integer between 1 and 5, and R1 being independently selected from C1. 1-10 A straight-chain or branched alkylene group, wherein the R2 in each of the n repeating units is independently selected from C 1-10 Straight-chain or branched alkylene groups, R3 selected from H and C 1-10 Straight-chain or branched alkyl groups; each of the R4 groups is independently selected from H and C. 1-10 Straight-chain or branched alkyl groups; the R5 group is selected from H, C 1-10 Straight-chain or branched alkyl groups and C 6-10 Aryl group; the R6 group is selected from H, C 1-10 Straight-chain or branched alkyl groups and C 6-10 Aryl.

[0022] According to the present invention, more preferably, in formulas (I) and (I'), HO is located at the meta position on the chain containing R1 on the benzene ring, y is 1, the R group is located at the para position on the chain containing R1 on the benzene ring, the R group is selected from tert-butyl, n is an integer between 1 and 3, and R1 is independently selected from C 1-4 A straight-chain or branched alkylene group, wherein the R2 in each of the n repeating units is independently selected from C 1-4Straight-chain or branched alkylene groups, R3 selected from H and C 1-4 Straight-chain or branched alkyl groups; each of the R4 groups is independently selected from H and C. 1-4 Straight-chain or branched alkyl groups; the R5 group is selected from H, C 1-4 Straight-chain or branched alkyl and phenyl groups; the R6 group is selected from H, C 1-4 Straight-chain or branched alkyl and phenyl groups.

[0023] According to the present invention, the individual groups in the organophosphorus compound conform to the bonding rules.

[0024] According to the present invention, examples of the organophosphorus compound include one or more of the following structural compounds:

[0025]

[0026]

[0027]

[0028] According to the present invention, the method for preparing the organophosphorus compound includes the following steps:

[0029] (1) React the compound shown in formula (α) with the peroxide;

[0030]

[0031] In formula (α), HO is bonded to the benzene ring; y R groups are bonded to the benzene ring; y is selected from integers between 0 and 4; and each R group is independently selected from H and C. 1-10 Straight-chain or branched alkyl groups; n is an integer between 1 and 10; R1 is independently selected from C 1-20 A straight-chain or branched alkylene group; the R2s in the n repeating units may be the same or different from each other, and each is independently selected from C. 1-20 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-20 Straight-chain or branched alkyl; the A” groups in the n repeating units may be the same or different from each other, and each is independently selected from... The R4 groups are each independently selected from H and C. 1-20 Straight-chain or branched alkyl groups;

[0032] (2) React the reaction product of step (1) with the compound shown in formula (β) and collect the product;

[0033]

[0034] In formula (β), the X group is selected from R5 and OR5, where the R5 group is selected from H and C. 1-20 Straight-chain or branched alkyl groups and C6-18 aryl, wherein the aryl group is optionally coated with one or more C 1-4 The R5 group is optionally substituted with one or more halogens, and the R5 group is optionally substituted with one or more hydroxyl groups; the X' group is selected from R6 and OR6, wherein the R6 group is selected from H and C. 1-20 Straight-chain or branched alkyl groups and C 6-18 aryl, wherein the aryl group is optionally coated with one or more C 1-4 The R6 group may be substituted with a straight-chain or branched alkyl group, and may optionally be substituted with one or more halogens or hydroxyl groups.

[0035] According to the present invention, the R5 and R6 groups can each be independently selected from methyl, ethyl, hydroxymethyl, chloromethyl, and phenyl, for example, the R5 group is selected from methyl or ethyl, and the R6 group is selected from phenyl.

[0036] According to the present invention, preferably, in formula (α), HO is located at the meta position on the chain containing R1 on the benzene ring, y is an integer between 1 and 3, y R groups are located at the para or ortho position on the chain containing R1 on the benzene ring, and the R groups are selected from C 1-4 Straight-chain or branched alkyl groups, n being an integer between 1 and 5, and R1 being independently selected from C1. 1-10 A straight-chain or branched alkylene group, wherein the R2 in each of the n repeating units is independently selected from C 1-10 Straight-chain or branched alkylene groups, R3 selected from H and C 1-10 Straight-chain or branched alkyl groups; each of the R4 groups is independently selected from H and C. 1-10 Straight-chain or branched alkyl groups; the R5 group is selected from H, C 1-10 Straight-chain or branched alkyl groups and C 6-10 Aryl group; the R6 group is selected from H, C 1-10 Straight-chain or branched alkyl groups and C 6-10 Aryl.

[0037] According to the present invention, more preferably, in formula (α), HO is located at the meta position on the chain containing R1 on the benzene ring, y is 1, the R group is located at the para position on the chain containing R1 on the benzene ring, the R group is selected from tert-butyl, n is an integer between 1 and 3, and R1 is independently selected from C 1-4 A straight-chain or branched alkylene group, wherein the R2 in each of the n repeating units is independently selected from C 1-4 Straight-chain or branched alkylene groups, R3 selected from H and C 1-4 Straight-chain or branched alkyl groups; each of the R4 groups is independently selected from H and C. 1-4 Straight-chain or branched alkyl groups; the R5 group is selected from H, C 1-4 Straight-chain or branched alkyl and phenyl groups; the R6 group is selected from H, C 1-4Straight-chain or branched alkyl and phenyl groups.

[0038] According to the present invention, in step (1), the compound represented by formula (α) can be selected from cashew phenol and alkylated cashew phenol. The alkylated cashew phenol can be obtained by reacting cashew phenol with an alkylating agent, for example, by reacting cashew phenol with tert-butyl chloride to obtain tert-butylated cashew phenol.

[0039] According to the present invention, in step (1), the peroxide is preferably one or more of hydrogen peroxide, formic acid, peracetic acid, persulfonic acid, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peracetic acid, methyl ethyl ketone peroxide, benzoyl peroxide and cyclohexanone peroxide, more preferably one or more of hydrogen peroxide, formic acid, peracetic acid and persulfonic acid.

[0040] According to the present invention, in step (2), the compound represented by formula (β) may be selected from one or more of alkoxyphosphoric acid, aryloxyphosphoric acid, alkoxyphosphonic acid, haloalkylphosphonic acid and hydroxysubstituted alkylphosphoric acid, for example, one or more of methylphosphonic acid, chloromethylphosphonic acid, phenoxyphosphoric acid, ethoxyphosphoric acid, hydroxymethylphosphonic acid and phenoxymethoxyphosphoric acid may be selected.

[0041] According to the present invention, the equivalence ratio between the compound represented by formula (α) and the peroxide and the compound represented by formula (β) is preferably 1:0.5 to 10:0.5 to 10, more preferably 1:2 to 5:2 to 5.

[0042] According to the present invention, 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 70-120°C.

[0043] According to the present invention, a catalyst may be added in step (1), preferably an acidic catalyst, such as one or more of concentrated sulfuric acid, zinc chloride, aluminum trichloride, benzenesulfonic acid and titanate, and the amount of catalyst added is preferably 0.01% to 3% of the compound shown in formula (α). After the reaction in step (1) is completed, the catalyst may be removed by alkaline washing and / or water washing.

[0044] According to the present invention, a catalyst may be added in step (2), preferably an acidic catalyst, such as one or more of concentrated sulfuric acid, zinc chloride, aluminum trichloride, benzenesulfonic acid and titanate, and the amount of catalyst added is preferably 0.5% to 10% of the compound shown in (α). After the reaction in step (2) is completed, the catalyst may be removed by alkaline washing and / or water washing.

[0045] According to the present invention, the reaction steps (1) and (2) can be carried out in the presence of a diluent and / or a solvent, or without the use of a diluent and / or a solvent.

[0046] According to the present invention, the diluent may be selected from one or more of API Group I, II, III, IV and V base oils. Common products or grades 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.

[0047] According to the present invention, the solvent may be water, 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 gasoline, etc. These solvents may be used individually, or in combination of two or more. The solvents may be removed after the reaction is complete, using methods known to those skilled in the art, such as under normal or reduced pressure.

[0048] According to a particular embodiment of the present invention, the diluent and / or solvent may be added at any stage of the reaction step in the amounts conventional in the art, without particular limitation.

[0049] According to the present invention, the reaction can be carried out under the protection of an inert gas atmosphere. Examples of inert gases include nitrogen and argon, and there is no particular limitation.

[0050] According to the present invention, the aforementioned preparation method can produce a single organophosphorus compound, a mixture of multiple organophosphorus compounds, or a mixture of one or more organophosphorus compounds with the aforementioned diluent (if used) as the reaction product. These reaction products are all contemplated by the present invention, and their different forms do not affect the achievement of the effects of the present invention. Therefore, in the context of this specification, these reaction products are collectively referred to as organophosphorus compounds without distinction. In view of this, according to the present invention, there is no absolute necessity for further purification of the reaction product or for further separation of an organophosphorus compound with a specific structure from the reaction product. Of course, such purification or separation is preferred for further enhancing the intended effects of the present invention, but is not essential to the present invention. Nevertheless, methods for purification or separation, such as column chromatography or preparative chromatography, can be cited as examples.

[0051] The organophosphorus compounds of this invention also possess excellent antioxidant, anti-wear, and friction-reducing properties.

[0052] The method for preparing organophosphorus compounds of the present invention has simple steps and high conversion rate in the reaction process.

[0053] The organophosphorus compounds of the present invention can be used as antioxidants, anti-wear agents, and friction reducers in lubricants. Attached Figure Description

[0054] Figure 1 The infrared spectrum of the product of Example 2 is shown below.

[0055] Figure 2 The image shows the carbon NMR spectrum of the product from Example 2. Detailed Implementation

[0056] The present invention will be further illustrated by the following embodiments, but these are not intended to limit the scope of the invention.

[0057] The raw materials used are as follows:

[0058] Cashew phenol, Shanghai Wujing Chemical Technology Co., Ltd., industrial products

[0059] Zinc chloride, Sinopharm Chemical Reagent Co., Ltd., analytical grade

[0060] Concentrated sulfuric acid, Sinopharm Chemical Reagent Co., Ltd., analytical grade.

[0061] Hydrogen peroxide (30%), Sinopharm Chemical Reagent Co., Ltd., analytical grade.

[0062] Formic acid, Sinopharm Chemical Reagent Co., Ltd., analytical grade

[0063] Methylphosphonic acid, Sinopharm Chemical Reagent Co., Ltd., chemically pure

[0064] Chloromethylphosphonic acid, Sinopharm Chemical Reagent Co., Ltd., chemically pure

[0065] Ethoxyphenoxyphosphate, Sinopharm Chemical Reagent Co., Ltd., chemically pure

[0066] tert-butyl chloride, Sinopharm Chemical Reagent Co., Ltd., analytical grade

[0067] Antioxidant T501, Xingpu Company, Research Institute of Petroleum and Chemical Industry, Industrial Product

[0068] Antioxidant T512, Xingpu Company, Research Institute of Petroleum and Chemical Industry, Industrial Products

[0069] Toluene, Sinopharm Chemical Reagent Co., Ltd., analytical grade

[0070] Tricresol phosphate (TCP), Sinopharm Chemical Reagent Co., Ltd., chemically pure.

[0071] Polyol esters, Sinopec Lubricating Oil Company Chongqing Branch, industrial products

[0072] 150SN base oil, Sinopec Yanshan Petrochemical Branch, industrial products

[0073] Example 1: Preparation of tert-butylated cashew phenol

[0074] Take 100g of cashew nut shell powder, 8g of formic acid, 0.3g of sulfuric acid, and 200g of hydrogen peroxide, and add them to a three-necked flask equipped with a mechanical stirrer, reflux condenser, and temperature control. Turn on the stirrer and heat. Maintain the reaction temperature at 70℃ and react for 3 hours. After the reaction is complete, cool down to obtain a brownish-red transparent liquid. Filter the reaction product and wash it with 5% KOH solution, then wash it with distilled water until neutral. Distill the organic phase under reduced pressure at 100Pa and 150℃ for 1 hour to remove water and unreacted raw materials, obtaining an orange-red transparent liquid epoxidized cashew nut shell powder.

[0075] 35g of epoxidized cashew nut shell phenol was dissolved in 100ml of acetone. After dissolution, the solution was transferred to a 250ml three-necked reaction flask, and 0.9g of zinc chloride catalyst was added. The mixture was stirred and heated. The reaction temperature was maintained at 60℃. 9.5g of tert-butyl chloride was slowly added dropwise to the reaction flask. After the addition was complete, the reaction was continued for 3 hours. After the reaction was completed, the temperature was lowered to obtain a brownish-red transparent liquid. The reaction product was filtered and washed with 5% KOH solution, then washed with distilled water until neutral. The product was then distilled under reduced pressure at 1000Pa and 120℃ for 1 hour to remove the solvent, water, and unreacted raw materials, yielding a brownish-red viscous liquid, tert-butylated epoxidized cashew nut shell phenol.

[0076] An example reaction formula for the above reaction is shown below.

[0077]

[0078] 20g of the tert-butylated epoxy cashew phenol prepared in Example 1, 0.2g of concentrated sulfuric acid, 10g of water, and 100g of toluene were added to a three-necked flask equipped with a mechanical stirrer and a reflux condenser. The mixture was stirred, heated, and refluxed at 85°C for 1 hour. Then, 50g of an aqueous solution of methylphosphonic acid (containing 10g of methylphosphonic acid) was added dropwise. After the addition was complete, the reaction was continued under reflux for 5 hours, and then the reaction was stopped. The product was washed three times with water, and finally the solvent was evaporated to obtain organophosphorus compound W-01 with a phosphorus content of 9.8%.

[0079] Since the reactants are a mixture of tert-butylated epoxide cashew phenols such as monoepoxides, diepoxides, and triepoxides, there are many reactions and reaction products. Therefore, the main reaction formulas that represent the reaction with tert-butylated epoxide cashew phenols as raw materials are shown in the following example.

[0080]

[0081] The product prepared in Example 2 was subjected to infrared spectroscopy and nuclear magnetic resonance analysis. The infrared spectrum is shown in the figure. Figure 1 The analysis results are shown in Table 1, and the NMR spectra are shown in Table 1. Figure 2 The analysis results are shown in Table 2.

[0082] Table 1 Infrared analysis results of the products

[0083]

[0084] Table 1 shows that the product contains characteristic peaks such as C-OH stretching vibration peak, P=O stretching vibration peak, benzene ring skeleton stretching vibration peak, POC stretching vibration peak, and PO stretching vibration peak, which indicates that the synthesized product is the target compound.

[0085] Table 2. Results of NMR spectroscopy analysis of the products

[0086]

[0087] The C element assignments in Table 2 indicate that the synthesized product is the target compound.

[0088] Example 3

[0089] 20g of the tert-butylated epoxy cashew phenol prepared in Example 1, 0.2g of concentrated sulfuric acid, 10g of water, and 100g of toluene were added to a three-necked flask equipped with a mechanical stirrer and a reflux condenser. The mixture was stirred, heated, and refluxed at 95°C for 1 hour. Then, 50g of an aqueous solution of chloromethylphosphonic acid (containing 10g of chloromethylphosphonic acid) was added dropwise. After the addition was complete, the reaction was continued under reflux for 3 hours, and then the reaction was stopped. The product was washed three times with water, and finally the solvent was evaporated to obtain the organophosphorus compound W-02 with a phosphorus content of 8.1%.

[0090] Example 4

[0091] 20g of the tert-butylated epoxy cashew phenol prepared in Example 1, 0.2g of concentrated sulfuric acid, 10g of water, and 100g of toluene were added to a three-necked flask equipped with a mechanical stirrer and a reflux condenser. The mixture was stirred, heated, and refluxed at 110°C for 1 hour. Then, 20g of ethoxyphenoxyphosphoric acid was added dropwise. After the addition was complete, the reaction was continued under reflux for 6 hours, at which point the reaction was stopped. The product was washed three times with water, and finally the solvent was evaporated to obtain the organophosphorus compound W-03, which had a phosphorus content of 7.5%.

[0092] Example 5

[0093] W-01, W-02, W-03, the comparative extreme pressure anti-wear agent TCP, and the hindered phenolic antioxidants T501 and T512 were added to polyol esters or 150SN base oil at a dosage of 0.5% to conduct SRV anti-wear and friction reduction evaluation experiments to determine their anti-wear and friction reduction performance. The test conditions for the SRV anti-wear and friction reduction evaluation experiment were: temperature 30℃, load 200N, stroke 1mm, test time 1 hour, and frequency 50Hz. The SRV method is described in the National Energy Administration standard NB / SH / T 0847-2010. The measurement results are shown in Table 3.

[0094] Table 3 SRV Test Results

[0095]

[0096] As can be seen from the test results in Table 3, the organophosphorus compounds of the present invention have a lower coefficient of friction and wear scar diameter compared with the blank base oil, and also have a lower coefficient of friction and wear scar diameter compared with the comparative additives. In particular, they exhibit excellent anti-wear and friction-reducing properties in 150SN base oil.

[0097] Example 6

[0098] W-01, W-02, W-03, hindered phenolic antioxidants T501 and T512, and extreme pressure anti-wear agent TCP were added to polyol esters or 150SN base oil at a dosage of 0.5% respectively, and their antioxidant properties were tested. The test results are shown in Table 4. The test instrument was a TA5000 DSC instrument from TA Instruments, USA. The test conditions were: 190℃, oxygen pressure 0.5MPa, and heating rate 10℃ / min.

[0099] Table 4. Antioxidant Test Results

[0100]

[0101] The comparison shows that the organophosphorus compounds of the present invention can significantly improve the oxidation induction period of base oils and have a higher oxidation induction period compared with comparative additives, especially exhibiting excellent antioxidant properties in polyol ester base oils.

Claims

1. An organophosphorus compound, selected from one or more compounds with the following structures: 。 2. A method for preparing the organophosphorus compound according to claim 1, comprising the following steps: (1) React tert-butylated cashew phenol with peroxide; (2) React the reaction product of step (1) with compound (β) and collect the product; the compound (β) is selected from one or more of methylphosphonic acid, chloromethylphosphonic acid and ethoxyphenoxyphosphoric acid.

3. The method according to claim 2, characterized in that, The peroxide is selected from one or more of hydrogen peroxide, peroxyformic acid, peracetic acid, persulfonic acid, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peracetic acid, methyl ethyl ketone peroxide, benzoyl peroxide, and cyclohexanone peroxide.

4. The method according to claim 2, characterized in that, The equivalence ratio between tert-butylated cashew phenol and peroxide, (β) compound is 1:0.5~10:0.5~10; the reaction temperature of step (1) is 0-100℃; the reaction temperature of step (2) is 50-150℃.

5. The method according to claim 2, characterized in that, The equivalence ratio between tert-butylated cashew phenol and peroxide, (β) compound is 1:2~5:2~5; the reaction temperature of step (1) is 20-80℃; the reaction temperature of step (2) is 70-120℃.

6. Use of the organophosphorus compound of claim 1 or the organophosphorus compound prepared by the method according to any one of claims 2 to 5 as an antioxidant, anti-wear agent or friction reducer in lubricants.

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