Preparation method and application of organic amide friction modifier

Abstract

The invention discloses a preparation method of an organic amide friction modifier, which specifically comprises the following steps: mixing unsaturated fatty acid ester and alkyl diamine, adding a catalyst, carrying out a stirring reaction, then carrying out reduced pressure distillation, taking out byproducts generated in the reaction process through a water diversion device, promoting the reaction to proceed to a target product, cooling after the reaction is finished, and filtering to obtain the organic amide friction modifier. The organic amide friction modifier is obtained. The organic amide friction modifier can be applied to lubricating oil. The organic amide friction modifier disclosed by the invention does not contain S, P and metal elements, so that generation of thermal oxide deposits of oil products is not increased; and when the organic amide friction modifier is cooperatively used with other additives in lubricating oil, the friction coefficient of an oil product can be reduced, and the purposes of saving energy and reducing fuel consumption are achieved.

Description

Technical Field

[0001] The invention belongs to the technical field of preparation of novel lubricating oil additives, and specifically relates to a method for preparing an organic amide friction modifier, and also relates to the application of the organic amide friction modifier Background Art

[0002] During the operation of machinery, friction and wear are one of the three main forms of damage and failure of materials and equipment. If friction can be controlled and reduced, it can not only reduce the cost of equipment maintenance, but also save the cost of manufacturing parts and the materials required. Therefore, reducing friction and reducing wear are the key points to reduce economic losses. The increase in fuel consumption and crude oil demand caused by automobile traffic, and the mandatory implementation of the national standard for vehicle fuel consumption limits have made improving automobile fuel economy and reducing automobile fuel consumption a technical problem that the automobile manufacturing industry and related industries urgently need to solve.

[0003] Improving the fuel economy of engine lubricants by adding friction modifiers helps reduce wear and save energy, which is an important direction for future development; however, friction modifiers containing elements such as S and P, although they have excellent tribological properties, can bring about relatively serious corrosion problems; although organic metal molybdenum friction modifiers improve the friction reduction performance of oil products, they contain metal elements and increase the formation of thermal oxide deposits in the oil products, thereby affecting the exhaust emission three-way catalytic converter system, and the friction reduction performance decreases as the oil products oxidize.

[0004] With the iterative upgrade of engine emission specifications, increasingly stringent emission regulations, higher and higher energy-saving requirements and the application of new materials, the wear resistance of the engine friction surface has improved, the gap in the structural design has become smaller, the lubricating oil film strength and film-forming ability have increased and the viscosity has become lower. The viscosity of the lubricating oil on the market is generally high, which is not conducive to energy saving and reducing fuel consumption. Summary of the invention

[0005] The purpose of the present invention is to provide a method for preparing an organic amide friction modifier, thereby improving the anti-wear and friction-reducing performance of the friction modifier.

[0006] Another object of the present invention is to provide the use of the above organic amide friction modifier in lubricating oil.

[0007] The technical scheme adopted by the present invention is a method for preparing an organic amide friction modifier, which specifically comprises: mixing an unsaturated fatty acid ester and an alkyl diamine, adding a catalyst, carrying out a stirring reaction, and then carrying out reduced pressure distillation, taking out the by-products produced during the reaction process through a water separation device, cooling after the reaction is completed, and obtaining the organic amide friction modifier.

[0008] The present invention is also characterized in that:

[0009] The temperature during the stirring reaction is 120-180°C for 4-8 hours; the reduced pressure distillation time is 2-5 hours.

[0010] The unsaturated fatty acid ester is unsaturated fatty acid methyl ester or unsaturated fatty acid ethyl ester; the carbon chain lengths of the unsaturated fatty acid methyl ester and the unsaturated fatty acid ethyl ester are both between 14 and 20.

[0011] The alkyl diamine is any one of N-coconut oil-1,3-propylene diamine, N-tallow oil-1,3-propylene diamine, N-hydrogenated tallow oil-1,3-propylene diamine, N-hydrogenated palmityl-1,3-propylene diamine, N-octadecyl-1,3-propylene diamine, N-dodecyl-1,3-propylene diamine and N-tetradecyl-1,3-propylene diamine.

[0012] The mass ratio of unsaturated fatty acid ester to alkyl diamine is 0.85-1.15:1.

[0013] The catalyst is sodium methoxide, hexamethylenetetramine or a solid base catalyst.

[0014] The solid base catalyst is a HND solid base catalyst or a phosphazene solid base catalyst.

[0015] The beneficial effects of the present invention are:

[0016] 1. The organic amide friction modifier of the present invention does not contain S, P and metal elements, and will not increase the formation of thermal oxide deposits in oil products;

[0017] 2. The organic amide friction modifier of the present invention has a relatively high desorption temperature, forms good protection on the friction surface of low-viscosity oil products, and reduces the friction coefficient;

[0018] 3. When the organic amide friction modifier of the present invention is used in conjunction with other additives in lubricating oil, it can reduce the friction coefficient of the oil, thereby achieving the purpose of energy saving and reducing fuel consumption;

[0019] 4. The organic amide friction modifier of the present invention has a simple preparation process, good process stability, an environmentally friendly reaction system, and mild reaction conditions. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 is the infrared spectrum of the organic amide friction modifier of the present invention;

[0021] Figure 2 is a thermogravimetric spectrum of the organic amide friction modifier of the present invention;

[0022] Figure 3 It is a friction performance test chart of the organic amide friction modifier in Examples 1-3 of the present invention. DETAILED DESCRIPTION

[0023] The present invention is described in detail below through specific implementation modes and accompanying drawings.

[0024] The preparation method of the organic amide friction modifier of the present invention specifically comprises the following steps: unsaturated fatty acid ester and alkyl diamine are mixed, a catalyst is added, and a stirring reaction is carried out. After the reaction has lasted for a period of time, the pressure is reduced at the temperature, by-products generated during the reaction are taken out through a water separation device to promote the reaction to the target product, and the temperature is lowered after the reaction is completed to obtain the organic amide friction modifier.

[0025] When stirring the reaction, the temperature is 120-180°C, the time is 4-8 hours, and the reduced pressure distillation time is 2-5 hours;

[0026] The unsaturated fatty acid ester is unsaturated fatty acid methyl ester or unsaturated fatty acid ethyl ester; the carbon chain length of the unsaturated fatty acid methyl ester and the unsaturated fatty acid ethyl ester is between 14 and 20;

[0027] Such as methyl hexadecenoate, methyl octadecenoate, methyl heavy oleate, methyl octadecadienoate, methyl linolenate, methyl ricinoleate, ethyl hexadecenoate, ethyl octadecenoate, ethyl heavy oleate, ethyl octadecadienoate, ethyl linolenate, ethyl ricinoleate, etc.;

[0028] The alkyl diamine is any one of N-coconut oil-1,3-propylene diamine, N-tallow-1,3-propylene diamine, N-hydrogenated tallow-1,3-propylene diamine, N-hydrogenated palmityl-1,3-propylene diamine, N-octadecyl-1,3-propylene diamine, N-dodecyl-1,3-propylene diamine and N-tetradecyl-1,3-propylene diamine;

[0029] The mass ratio of unsaturated fatty acid ester to alkyl diamine is 0.85-1.15:1;

[0030] The catalyst is sodium methoxide, hexamethylenetetramine or a solid base catalyst; the solid base catalyst is specifically a HND solid base catalyst or a phosphazene solid base catalyst;

[0031] The product of the present invention is a friction modifier used as a lubricating oil additive. Considering the solubility of the prepared organic amide friction modifier in lubricating oil, the availability of raw materials and other performance requirements, the present invention selects unsaturated fatty acid esters and alkyl diamines as reactants. The reaction mechanism is that the unsaturated fatty acid ester and the alkyl diamine are condensed to obtain the organic amide friction modifier. The reaction equation is as follows:

[0032]

[0033] In the amide molecule, C, N and the four atoms connected to C and N are all on the same plane, and the functional group has a strong adsorption force that can react with the metal surface and anchor on the metal surface. The hydrocarbon group at the other end of the molecule dissolves in the oil and forms a directional arrangement on the metal surface, thereby forming a protective layer between the friction mechanical interface, thereby achieving the purpose of reducing friction. During use, the protective layer formed by the amide friction modifier on the metal surface will not cause molecular structure damage due to high temperature and long-term use, thereby destroying the protective layer, achieving a long-term friction reduction and lasting effect.

[0034] Example 1

[0035] The first step of the reaction is to add 135g of methyl hexadecenoate and 18.3g of N-cocoyl-1,3-propylene diamine into a four-necked flask, and then add 0.3g of an alkaline catalyst containing sodium element into the four-necked flask while the two materials are heated and dissolved; the temperature is raised to 125°C, and the reaction is stirred for 8h, and then the reduced pressure distillation is carried out at this temperature for 5h, and the temperature is lowered after the reaction is completed to obtain an organic amide friction modifier.

[0036] Example 2

[0037] The first step of the reaction is to add 148.3g of methyl octadecenoate and 51g of N-tallow-1,3-propylene diamine into a four-necked flask, and then add 0.5g of HND solid base catalyst into the four-necked flask while the two materials are heated and dissolved; the temperature is raised to 150°C, and the reaction is stirred for 6h, and then the reduced pressure distillation is carried out at this temperature for 4h. After the reaction is completed, the temperature is lowered to obtain an organic amide friction modifier.

[0038] Example 3

[0039] The first step of the reaction is to add 146g of methyl linolenate and 81g of N-oleyl-1,3-propylene diamine into a four-necked flask, and then add 1g of sodium hydroxide into the four-necked flask while the two materials are heated and dissolved; the temperature is raised to 180°C, and the reaction is stirred for 3h, and then the reduced pressure distillation is carried out at this temperature for 2h. After the reaction is completed, the temperature is lowered to obtain an organic amide friction modifier.

[0040] The infrared spectra of the organic amide friction modifiers prepared in Examples 1-3 are shown in Figure 1 , it can be seen from the figure that 3315cm -1 The NH contraction vibration absorption of amide group, 1636cm -1 The carbonyl stretching vibration of the amide I band is 1559 cm -1 The amide II band is the amide bending and stretching vibration, 1272 cm -1 It is the absorption peak of amide III band; 2923cm -1 、2853cm -1It is the absorption peak of CH2 asymmetric and symmetric stretching vibration; therefore, it can be concluded that there is an amide structure in the synthesized organic amide friction modifier; the thermogravimetric decomposition spectrum is shown in Figure 2 ,It can be seen from the figure that the synthesized organic amide friction modifier has a higher thermal decomposition temperature and can be applied to higher working environments, avoiding functional failure caused by its own thermal decomposition;

[0041] The friction performance evaluation results of different embodiments in the formulation system are shown in Figure 3 ,It can be seen from the figure that the organic amide friction modifier has a smaller friction coefficient under different temperature conditions, that is, it can achieve a good friction reduction effect in oil products.

[0042] The preparation method of the organic amide friction modifier of the present invention can reduce the friction coefficient of the oil product when used in conjunction with other additives in lubricating oil, thereby achieving the purpose of energy saving and improving fuel economy. At the same time, the preparation process of the present invention is simple, the process is stable, and the reaction system is safe, environmentally friendly, and has high controllability and mild reaction conditions.

Claims

1. A method for preparing an organic amide friction modifier, characterized in that: Specifically, unsaturated fatty acid ester and alkyl diamine are mixed, a catalyst is added, and a stirring reaction is carried out, followed by vacuum distillation, by-products produced during the reaction are taken out through a water separation device to promote the reaction to the target product, and the temperature is lowered after the reaction is completed to obtain an organic amide friction modifier.

2. The method for preparing the organic amide friction modifier according to claim 1, characterized in that: The temperature during the stirring reaction is 120-180°C for 4-8 hours; the reduced pressure distillation time is 2-5 hours.

3. The method for preparing the organic amide friction modifier according to claim 1, characterized in that: The unsaturated fatty acid ester is unsaturated fatty acid methyl ester or unsaturated fatty acid ethyl ester; the carbon chain lengths of the unsaturated fatty acid methyl ester and the unsaturated fatty acid ethyl ester are both between 14 and 20.

4. The method for preparing the organic amide friction modifier according to claim 1, characterized in that: The alkyl diamine is any one of N-coconut oil-1,3-propylene diamine, N-tallow-1,3-propylene diamine, N-hydrogenated tallow-1,3-propylene diamine, N-hydrogenated palmityl-1,3-propylene diamine, N-octadecyl-1,3-propylene diamine, N-dodecyl-1,3-propylene diamine, and N-tetradecyl-1,3-propylene diamine.

5. The method for preparing the organic amide friction modifier according to claim 1, characterized in that: The mass ratio of the unsaturated fatty acid ester to the alkyl diamine is 0.85-1.15:

1.

6. The method for preparing the organic amide friction modifier according to claim 1, characterized in that: The catalyst is sodium methoxide, hexamethylenetetramine or a solid base catalyst.

7. The method for preparing the organic amide friction modifier according to claim 6, characterized in that: The solid base catalyst is a HND solid base catalyst or a phosphazene solid base catalyst.

8. Use of the organic amide friction modifier according to any one of claims 1 to 7 in lubricating oil.

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