CN113293038A

CN113293038A - Preparation method and application of amine antiwear agent for ultra-low sulfur clean diesel oil

Info

Publication number: CN113293038A
Application number: CN202110697768.9A
Authority: CN
Inventors: 胡震; 李合; 于海莲; 朱蠡庆
Original assignee: Sichuan University of Science and Engineering
Current assignee: Sichuan University of Science and Engineering
Priority date: 2021-06-23
Filing date: 2021-06-23
Publication date: 2021-08-24
Anticipated expiration: 2041-06-23
Also published as: CN113293038B

Abstract

The invention discloses a preparation method and application of an amine antiwear agent for ultra-low sulfur clean diesel oil, wherein idesia oil and glycol amine are selected as raw materials, the idesia oil and the glycol amine are added into an organic solvent according to the molar ratio of 1 (1.0-3.5), sodium ethoxide is added as a catalyst, the mixture is stirred and mixed, a reaction system is heated to 115-165 ℃ for reaction, and then the reaction system is refined to obtain the antiwear agent. The idesia oil diethanolamide as a new antiwear agent is prepared by using idesia oil and diethanolamide as raw materials under the catalysis of sodium ethoxide through a one-step method, and the method has the advantages of mild conditions in the whole reaction process, simplicity in operation, easiness in obtaining of raw materials and good industrial prospect.

Description

Preparation method and application of amine antiwear agent for ultra-low sulfur clean diesel oil

Technical Field

The invention relates to the technical field of organic synthesis, in particular to a preparation method and application of an amine antiwear agent for ultra-low sulfur clean diesel oil.

Background

In recent years, the national requirements for sulfur indexes of automobile exhaust emission are more and more strict, and the development of a diesel oil deep hydrodesulfurization technology is promoted. The deep hydrodesulfurization technology used for processing the clean diesel fuel can obviously and effectively remove sulfur-containing components in crude oil to obtain high-quality clean fuel, but while removing a plurality of harmful hydrocarbons and sulfur-containing components, nitrogen-containing substances and naphthenes with natural lubricating property of the diesel are removed, which aggravates the damage caused by mutual friction of mechanical parts of a diesel engine. In order to solve the problem, the prior art adopts a high-efficiency antiwear agent to be doped into diesel oil to improve the lubricating property of the diesel oil, which is the most convenient, fastest and most effective technical means for reducing the loss of engine equipment. At present, diesel antiwear agents which are sold and widely used in the market are mainly fatty acids and fatty acid ester diesel antiwear agents. After the fatty acid antiwear agent is added into diesel oil, the acid value index of the diesel oil is increased, the corrosivity of the diesel oil is enhanced, if the additive is used for a long time, severe corrosion can be caused to an engine, particularly, an alkaline dispersing agent in hydrogenated diesel oil can also react with the fatty acid, magnesium salt and calcium salt in a generated product can block a fuel injection system of the engine, and great potential safety hazard exists. The fatty acid ester diesel antiwear agent contains various oxygen-containing functional groups, can form a compact protective film to cover a metal surface layer, can slow down the corrosion of metal and can enhance the lubricating performance, but the diesel antiwear agent is added into the diesel to cause the emulsification phenomenon of the diesel and easily cause the filter blockage, and the addition amount of the diesel antiwear agent is larger, so that the diesel antiwear agent can play a positive lubricating role only when the mass reaches more than 10 percent of the mass of the diesel. How to reduce the adverse effect of the antiwear agent on the engine system is a technical problem which needs to be solved by the technical personnel in the field.

Disclosure of Invention

Aiming at the defects in the prior art, the invention aims to provide a preparation method of an amine antiwear agent for ultra-low sulfur clean diesel oil, so as to solve the problems that an engine system is easy to block and corrode due to an antiwear agent in the prior art, and the dosage of the antiwear agent is large.

The invention also provides an application of the amine antiwear agent for the ultra-low sulfur clean diesel oil.

In order to solve the technical problems, the invention adopts the following technical scheme:

a preparation method of an amine antiwear agent for ultra-low sulfur clean diesel oil comprises the steps of selecting idesia oil and glycol amine as raw materials, adding the idesia oil and the glycol amine into an organic solvent according to a molar ratio of 1 (1.0-3.5), adding sodium ethoxide as a catalyst, stirring and mixing, heating a reaction system to 115-165 ℃ for reaction, and refining to obtain the antiwear agent.

Preferably, the addition amount of the sodium ethoxide is 0.05wt% to 1.1 wt%.

Preferably, the molar ratio of the idesia oil to the glycol amine is 1 (1.0-3.0).

Preferably, the reaction temperature is 120 ℃ to 160 ℃.

Preferably, the reaction time is 2.5h to 7.5 h.

Preferably, the organic solvent comprises one of carbon tetrachloride, toluene or benzene.

Preferably, the amount of the organic solvent is 15wt% to 70wt% of the total mass of the reaction system.

The invention also provides application of the amine antiwear agent for the ultra-low sulfur clean diesel oil, and the amine antiwear agent is added into 0# diesel oil and is mixed for use.

Preferably, the addition amount of the antiwear agent is 200 to 600 mu g/g.

Compared with the prior art, the invention has the following beneficial effects:

1. the idesia oil diethanolamide as a new antiwear agent is prepared by using idesia oil and diethanolamide as raw materials under the catalysis of sodium ethoxide through a one-step method, and the method has the advantages of mild conditions in the whole reaction process, simplicity in operation, easiness in obtaining of raw materials and good industrial prospect.

2. The idesia oil diethanolamide as the antiwear agent prepared by the method has good lubricating property, when the addition amount of the idesia oil diethanolamide in 0# diesel oil is only 200 mug/g, the diameter of a grinding mark of the 0# diesel oil is obviously reduced, the depth of the grinding mark is obviously reduced, and the lubricating property of the 0# diesel oil is obviously improved; meanwhile, the idesia oil diethanolamide as the antiwear agent prepared by the method can control the amine value of the product in a lower range, obviously weakens the corrosion effect on metals, and also avoids the reaction of the antiwear agent and other additives in diesel oil, thereby reducing the occurrence of the phenomenon of engine system blockage.

Drawings

FIG. 1 is an infrared spectrum of idesia oil and the antiwear agent of example 1.

FIG. 2 is a graph showing the effect of reaction temperature on the synthesis of diethanolamide of idesia polycarpa oil.

FIG. 3 is a graph showing the effect of reaction time on the synthesis of diethanolamide of idesia oil.

FIG. 4 shows the effect of the molar ratio of diethanolamine and idesia oil on the synthesis of the diethanolamide of idesia oil.

FIG. 5 is a graph showing the effect of catalyst loading on the synthesis of diethanolamide of idesia oil.

FIG. 6 is a graph showing the effect of solvent usage on the synthesis of diethanolamide of idesia oil.

FIG. 7 is an SEM micrograph of the wear plaques on the friction pair iron balls of non-additivated 0# diesel without the addition of the antiwear agent.

FIG. 8 is an SEM micrograph of wear specks on iron balls of a friction pair after addition of an antiwear agent of the present invention to non-additivated 0# diesel fuel.

FIG. 9 is an SEM micrograph of wear plaques on friction pair iron balls with additive 0# diesel without the antiwear agent added.

FIG. 10 is an SEM micrograph of wear specks on a friction pair iron ball after addition of 0# diesel fuel plus an antiwear agent of the present invention.

FIG. 11 shows the corrosion profile of non-additivated 0# diesel with the addition of an acid type antiwear agent.

FIG. 12 shows the corrosion profile of non-additivated 0# diesel with the antiwear agent of this patent added.

In the figure: 1 is the infrared spectrum of idesia oil, and 2 is the infrared spectrum of the antiwear agent prepared by the invention.

Detailed Description

The invention will be further explained with reference to the drawings and the embodiments.

Preparation method of amine antiwear agent for ultra-low sulfur clean diesel oil

The anti-wear agent is prepared by using idesia oil and glycol amine as raw materials, adding the idesia oil and the glycol amine into an organic solvent according to the molar ratio of 1 (1.0-3.5), adding sodium ethoxide as a catalyst, stirring and mixing, heating a reaction system to 115-165 ℃ for reaction, and refining the reaction system to obtain the anti-wear agent.

In specific implementation, the addition amount of the sodium ethoxide is 0.05wt% -1.1 wt%. The molar ratio of the idesia oil to the glycol amine is 1 (1.0-3.0). The reaction temperature is 120-160 ℃. The reaction time is 2.5 h-7.5 h. The organic solvent comprises one of carbon tetrachloride, toluene or benzene. The dosage of the organic solvent is 15wt% -70 wt% of the total mass of the reaction system.

TABLE 1

Examples	Reaction time	Reaction temperature	Sodium ethoxide addition	Molar ratio of idesia oil to glycol amine	Conversion rate of idesia oil
						1	5h	140℃	0.10wt％	1:2	95.85％
2	5h	135℃	0.05wt％	1:1.5	91.64％
						3	5.5h	140℃	0.05wt％	1:2.5	90.24％
4	5.5h	135℃	0.15wt％	1:2	89.96％
						5	6h	135℃	0.10wt％	1:2.5	89.90％

When the reaction process is researched, the reaction temperature, the reaction time, the molar ratio of diethanol amine to idesia polycarpa oil and the dosage of the catalyst can cause different influences on the conversion rate and the properties of the product, the performance of the antiwear agent is judged by measuring the amine value of the antiwear agent, and the higher the amine value is, the stronger the corrosion of the antiwear agent to an engine system is, so the amine value of the antiwear agent is strictly controlled.

1. Method for measuring amine value of antiwear agent

(1) Configuration of 0.5% bromophenol blue indicator

Weighing 0.5000g of bromophenol blue solid and a 100mL beaker, adding a little absolute ethyl alcohol to dissolve, transferring to a 100mL volumetric flask, and fixing the volume for later use.

(2) Measuring the amine number of the product

0.2000g of the product was accurately weighed into a 50mL Erlenmeyer flask. 40.00mL of absolute ethyl alcohol is measured by a measuring cylinder to dissolve the product, and 3-5 drops of 0.5% bromophenol blue indicator are added to obtain a blue solution. Titration was carried out with 0.1000mol/L hydrochloric acid-ethanol solution, and the end point was determined when the solution changed from blue to bright yellow and did not change color for 30 seconds. The consumption of the hydrochloric acid-ethanol solution was recorded. Triplicate determinations were made and the average was taken.

(3) Calculation of amine number

X: amine number of idesia oil diethanolamide (calculated by KOH), mg/g;

V₃: titrating the consumed hydrochloric acid-ethanol solution by mL;

m₂: weighing the product, g;

2. calculation method of idesia oil conversion rate

X₂: conversion of idesia oil,%;

n₁: mass of diethanolamine, mol;

n₂: amount of idesia oil, mol;

m₃: weighing the mass g of idesia oil;

m₄weighing the mass of diethanolamine in g.

3. Infrared spectroscopic analysis of product idesia oil diethanolamide

The products of examples 1-5 were characterized and analyzed by an infrared spectrometer, taking example 1 as an example, and the results are shown in fig. 1. As can be seen from the absorption peak wave number in FIG. 1, idesia oil and experimental product, 3431cm^-1The peak is a stretching vibration absorption peak of-OH association, 2925cm^-1The peak is-CH₃、-CH₂C-H stretching vibration absorption peak of-1738 cm^-1The peak is the carboxylic acid-C ═ O stretching vibration absorption peak at 1464cm^-1The peak is-CH₃、-CH₂Middle C-H bending vibration absorption peak. The idesia oil and the experimental product contain hydroxyl and carboxylic acid functional groups. 1626cm in the infrared spectrum of the experimental product^-1The peak is the stretching vibration peak of-C ═ O in-CON-, 1051cm^-1The peak is the C-N stretching vibration peak, and the two absorption peaks are the characteristic absorption peaks of the tertiary amide. From the analysis, the invention synthesizes the target product idesia oil diethanolamide through a one-step method.

4. Influence of reaction temperature on synthesis of idesia oil diethanolamide

Under the conditions that the molar ratio of the idesia oil to the diethanol amine is 1:2, the dosage of carbon tetrachloride as a solvent is 25 percent, and the dosage of sodium ethoxide as a catalyst is 1 percent, and the reaction is carried out for 5 hours, the influence of the reaction temperature on the conversion rate of the idesia oil is examined, as shown in the attached figure 2. It can be seen from FIG. 2 that the amine number of the antiwear agent prepared decreases with increasing reaction temperature at a stage where the reaction temperature is below 140 ℃. When the reaction temperature reaches 140 ℃, the amine value of the prepared antiwear agent is minimum. When the reaction temperature is higher than 140 ℃, the amine value of the prepared antiwear agent is slightly improved. The conversion rate of the idesia oil increases with the increase of the reaction temperature before the reaction temperature is 140 ℃. As the temperature rises, the energy of reactants increases, the number of activated molecules increases, the number of effective collisions increases, and the conversion increases. When the reaction temperature is 140 ℃, the conversion rate of the idesia oil reaches 90.92 percent at most, and the conversion rate is reduced when the reaction temperature is higher than 140 ℃, probably because the idesia oil and the diethanol have esterification reaction. Research shows that the optimal reaction temperature of the reaction under the condition is 140 ℃, and at the moment, the esterification reaction rate of the idesia oil and the diethanol amine is accelerated, so that the amine value of the product is minimum, and the conversion rate of the idesia oil is highest.

5. Influence of reaction time on synthesis of diethanolamide of idesia polycarpa oil

When the molar ratio of the idesia oil to the diethanol amine is 1:2, the amount of carbon tetrachloride as a solvent is 25%, the amount of sodium ethoxide as a catalyst is 1%, and the reaction temperature is 140 ℃, the influence of the reaction time on the conversion rate of the idesia oil is examined, as shown in the attached figure 3. As can be seen from FIG. 3, the amine number of the product decreased with the increase of the reaction time before the reaction time of 6 hours, the amine number of the product did not differ much between the reaction times of 5 hours and 6 hours, and the amine number of the product was the smallest at the reaction time of 6 hours. The conversion rate of the idesia oil is increased along with the increase of the reaction time before the reaction time is 5 h. The reaction time is 5-6 h, and the conversion rate is stable. When the reaction time is 6 hours, the conversion rate of the idesia oil reaches 94.03 percent. When the reaction time exceeds 6 hours, the conversion rate of the idesia oil is obviously reduced, the product is viscous and black, oxidation reaction possibly occurs, meanwhile, the amine value of the product is obviously increased, and hydrolysis possibly occurs under the alkaline and long-time reflux condition of the idesia oil diethanolamide. The study showed that the optimum reaction time of idesia oil under this condition was 6 h.

6. Influence of the molar ratio of diethanolamine to idesia oil on synthesis of idesia oil diethanolamide

When the amount of carbon tetrachloride is 25%, the amount of sodium ethoxide is 1%, the reaction temperature is 140 ℃ and the reaction time is 4 hours, the influence of the molar ratio of diethanolamine to idesia oil on the conversion rate of idesia oil is examined, as shown in figure 4. As can be seen from FIG. 4, the amine number of the product increased with increasing diethanolamine level. When the molar ratio of the idesia oil to the diethanolamine is less than 1:2, the conversion of the idesia oil increases with the increase of the diethanolamine, probably because of the probability of the amide reaction of the carboxyl group in the idesia oil with the increase of the diethanolamine amount. When the molar ratio of the idesia oil to the diethanol amine reaches 1: at 2, the conversion rate of the idesia oil is maximum and reaches 91.72 percent. When the molar ratio is more than 1:2, the conversion rate of the idesia oil is reduced, probably because the reaction between the idesia oil and the diethanol amine has competition of amidation reaction and esterification reaction, and along with the increase of the dosage of the diethanol amine, the probability of generating diethanol amine monoester and diethanol amine diester by side reaction is increased, and the generation of the diethanol amide of the idesia oil is influenced. Research shows that the optimal molar ratio of the idesia oil to the diethanol amine is 1:2 under the condition.

7. Influence of catalyst dosage on synthesis of idesia oil diethanolamide

When the molar ratio of the idesia oil to the diethanol amine is 1:2, the amount of carbon tetrachloride as a solvent is 25%, the reaction time is 5 hours, and the reaction temperature is 140 ℃, the influence of the sodium ethoxide as a catalyst on the conversion rate of the idesia oil diethanol amine is examined, as shown in figure 5. In the absence of catalyst, the fatty acid and diethanolamine can also undergo amidation reaction, but the reaction rate is extremely slow. As can be seen from FIG. 5, the amine number of the product decreases and then increases and then levels off as sodium ethoxide is added. When the addition amount of the sodium ethoxide is 0.1 wt%, the conversion rate of the idesia oil is the highest and can reach 95.85%. When the sodium ethoxide is added in an amount exceeding 0.1 wt%, the conversion rate of idesia oil gradually decreases, which is probably because as sodium ethoxide is added more hydrochloric acid is consumed in titrating the amine value, and as the alkalinity increases, the hydrolysis ability of the amide also increases, resulting in a decrease in the conversion rate of idesia oil. Research shows that under the condition, the optimal addition amount of the catalyst sodium ethoxide is 0.1%, and the excessive use amount of the sodium ethoxide catalyst can cause the amine value of the product to be larger.

8. Influence of solvent dosage on synthesis of idesia oil diethanolamide

When the molar ratio of the idesia oil to the diethanol amine is 1:2, the addition amount of the catalyst sodium ethoxide is 0.1%, the reaction time is 5 hours, and the reaction temperature is 140 ℃, the influence of the amount of the solvent carbon tetrachloride on the conversion rate of the idesia oil is examined, as shown in figure 6. As can be seen from the attached FIG. 6, the maximum phase difference value of the amine value of the product is only 2.05KOH mg/g with the increase of the solvent, and the dosage of the solvent has little influence on the amine value of the product. Meanwhile, the influence of the solvent dosage on the conversion rate of the idesia oil is not too large, the overall conversion rate tends to be stable and is kept above 95 percent, which probably means that the effect of solvent carbon tetrachloride as a dehydrating agent is good, and water generated in the amidation reaction can be fully brought out of a reaction system through boiling.

9. Orthogonal optimization experiment

Considering that the influence of the solvent dosage on the conversion rate of the idesia oil is not large, the synthesis process is optimized by respectively selecting four-factor three-level to perform an orthogonal test based on the factors of reaction time, reaction temperature, mole ratio of the idesia oil diethanolamide and catalyst dosage, and taking the conversion rate of the idesia oil as an investigation index. As the factor levels are shown in table 2, and the results of the orthogonal experiments are shown in table 3:

TABLE 2 level-factor table

TABLE 3 orthogonal experiment L₉(3⁴)

As can be seen from the above table, R is the corresponding factor K₁、K₂、K₃The difference between the median maximum and minimum. Comparing the R values, the reaction time is the most influenced on the reaction process, the molar ratio of the idesia oil to the diethanol amine and the dosage of the catalyst are the next, and the reaction temperature is the least influenced on the reaction. And adding the conversion rates of the levels corresponding to the factors to obtain the contribution to the conversion rate respectively. The results show that the optimum condition level is A₁B₂C₂D₂Namely: the reaction time is 5 hours, the reaction temperature is 140 ℃, the molar ratio of the idesia oil to the diethanol amine is 1:2, the dosage of the catalyst is 0.10 percent, and the conversion rate of the idesia oil is 95.85 percent.

Application of amine antiwear agent for ultra-low sulfur clean diesel oil

The antiwear agent is added into 0# diesel oil and used after being mixed, wherein the addition amount of the antiwear agent is 200-600 mug/g.

The effect evaluation of the antiwear agent adopts an SH/T0765 method, and the test is carried out on a high-frequency reciprocating tester under the following test conditions: the temperature is 60 ℃, the load is 200g, the frequency is 50Hz, the stroke is 1.0mm, the test time is 75min, the volume of an oil product is 2.0mL, the surface area of an oil groove is 600mm². In order to eliminate the influence of air humidity on abrasion, a corrected wear scar diameter WSD of l.4 was obtained by correction based on a water vapor pressure of 1.4kPa, and a friction coefficient was obtained and averaged.

Taking example 1 as an example, 200 μ g/g of the antiwear agent prepared in example 1 was added to non-additivated 0# diesel oil (wherein non-additivated means that no additive was added to the oil product), the influence of the antiwear agent on the lubricating performance of the non-additivated diesel oil was examined, the shapes of iron balls and iron pieces on friction pairs were measured using the Wear Scar Diameter (WSD) as an evaluation index, the results of the non-additivated 0# diesel oil of example 1 being not added are shown in fig. 7, and the results of the non-additivated 0# diesel oil of example 1 being added are shown in fig. 8. The comparison shows that the idesia oil diethanolamide antiwear agent prepared by the invention is applied to ultra-low sulfur non-additive 0# diesel oil, when the addition amount is only 200 mug/g, the diameter of the abrasion spot of the diesel oil corresponding to a friction pair iron ball is reduced to 320 mu m from the original 630 mu m, the reduction amplitude reaches 49.2 percent, and is far lower than the national requirement of 360 mu m, and the use requirement is met. In addition, the width of the abrasion marks of the iron sheet of the friction pair corresponding to the diesel oil is reduced to 440 μm from 550 μm, the reduction amplitude reaches 20.0%, and the scratch depth is obviously shallow after the antiwear agent prepared by the invention is added, which indicates that the friction is obviously reduced.

The antiwear agent prepared in example 1 was added to additivated 0# diesel fuel in an amount of 200 μ g/g, and the influence of the antiwear agent on the lubricating performance of additivated diesel fuel was examined, and the shapes of the iron balls and iron pieces of the friction pair were measured using the Wear Scar Diameter (WSD) as an evaluation index, and the results of adding additivated 0# diesel fuel in example 1 are shown in fig. 9 and the results of adding additivated 0# diesel fuel in example 1 are shown in fig. 10. The idesia oil diethanolamide antiwear agent prepared by the invention is applied to ultra-low sulfur additive 0# diesel, when the addition amount is only 200 mug/g, the diameter of the grinding spot of the diesel corresponding to a friction pair iron ball is reduced to 206μm from the original 318μm, the reduction amplitude reaches 35.2%, the reduction amplitude is far lower than the national requirement of 360μm, and the use requirement is met. In addition, the width of the abrasion marks of the iron sheet of the friction pair corresponding to the diesel oil is reduced to 270 mu m from the original 350 mu m, the reduction amplitude reaches 22.8 percent, and the scratch depth is obviously reduced after the antiwear agent prepared by the invention is added, which indicates that the friction is obviously reduced.

The corrosion appearance of the diesel oil on the friction pair iron ball is observed, so that whether the diesel oil corrodes the metal after the antiwear agent is added can be known. Respectively observing the corrosion morphology on the friction pair iron ball after the addition of the additive 0# diesel oil with the acid type antiwear agent and the addition of the antiwear agent of the invention to obtain a graph 11 and a graph 12, wherein the graph 11 shows the corrosion morphology on the friction pair iron ball after the addition of the additive 0# diesel oil with the acid type antiwear agent, and the graph 12 shows the corrosion morphology on the friction pair iron ball after the addition of the additive 0# diesel oil with the antiwear agent of the invention, and after comparing the graph 11 with the graph 12, a large number of black spots exist in the graph 11, which are formed by the friction pair being corroded by the acid component in the acid type antiwear agent, are very obvious and numerous, and can be seen everywhere in each area, so that the metal surface forms a pattern of scab and hundreds of holes. However, this phenomenon is not seen in fig. 12, and black spots are not seen on the wear spots after the antiwear agent of the present invention is added, and the surface of the friction pair is not uneven, and the trace of corrosion is not seen, which indicates that the antiwear agent of the present invention can effectively inhibit the occurrence of corrosion to the friction pair, thereby preventing the engine system from being damaged due to corrosion,

finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the technical solutions, and those skilled in the art should understand that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions, and all that should be covered by the claims of the present invention.

Claims

1. A preparation method of an amine antiwear agent for ultra-low sulfur clean diesel oil is characterized by selecting idesia oil and glycol amine as raw materials, adding the idesia oil and the glycol amine into an organic solvent according to a molar ratio of 1 (1.0-3.5), adding sodium ethoxide as a catalyst, stirring and mixing, heating a reaction system to 115-165 ℃ for reaction, and refining to obtain the antiwear agent.

2. The preparation method of the amine antiwear agent for ultra-low sulfur clean diesel oil according to claim 1, wherein the addition amount of sodium ethoxide is 0.05wt% -1.1 wt%.

3. The preparation method of the amine antiwear agent for the ultra-low sulfur clean diesel oil according to claim 1, wherein the molar ratio of the idesia oil to the glycol amine is 1 (1.0-3.0).

4. The preparation method of the amine antiwear agent for the ultra-low sulfur clean diesel oil according to claim 1, wherein the reaction temperature is 120-160 ℃.

5. The preparation method of the amine antiwear agent for the ultra-low sulfur clean diesel oil according to claim 1, wherein the reaction time is 2.5 h-7.5 h.

6. The method for preparing the amine antiwear agent for ultra-low sulfur clean diesel oil according to claim 1, wherein the organic solvent comprises one of carbon tetrachloride, toluene or benzene.

7. The preparation method of the amine antiwear agent for ultra-low sulfur clean diesel oil according to claim 1, wherein the amount of the organic solvent is 15wt% -70 wt% of the total mass of the reaction system.

8. The application of the amine antiwear agent for the ultra-low sulfur clean diesel oil is characterized in that the antiwear agent is added into 0# diesel oil and is used after being mixed.

9. The application of the amine antiwear agent for the ultra-low sulfur clean diesel oil according to claim 8 is characterized in that the addition amount of the antiwear agent is 200-600 [ mu ] g/g.