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Hydroxy-containing thiadiazole derivative, and preparation method and application thereof

A technology of hydroxythiadiazole and its derivatives, which is applied in the field of organic compounds and its preparation, can solve problems such as not meeting the requirements of environmental protection, achieve the effects of reducing the diameter of wear spots and enhancing the effect of extreme pressure and anti-wear

Active Publication Date: 2014-04-02
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] CN00801801.4 and CN00802316.6 disclose the reaction products and adducts of thiadiazole dimers and poly(ether) glycols as extreme pressure additives, and CN200480029627.4 discloses the lubricating combination of molybdenum-containing compounds and thiadiazoles The alkoxy chain is introduced into the thiadiazole parent material, which has good anti-wear and extreme pressure resistance properties, but its preparation uses halogenated hydrocarbons, which does not meet the requirements of environmental protection

Method used

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  • Hydroxy-containing thiadiazole derivative, and preparation method and application thereof
  • Hydroxy-containing thiadiazole derivative, and preparation method and application thereof
  • Hydroxy-containing thiadiazole derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take 7.5 g (0.05 mol) of 2,5-dimercapto-1,3,4-thiadiazole in a 150 ml three-necked flask, and add 50 ml of tetrahydrofuran as a solvent. After stirring at room temperature until uniformly mixed, 2.9 g (0.05 mol) of propylene oxide was slowly added dropwise. After the dropwise addition was completed, the temperature was raised to 80° C. to react for 24 hours. After the reaction, cool to room temperature, filter the reaction solution to remove insoluble matter, and then distill off the organic solvent to obtain the extreme pressure antiwear agent containing thiadiazole derivatives containing hydroxy. The product 2-(2'-hydroxypropyl)mercapto-5-mercapto-1,3,4-thiadiazole has a mass of 9.6 g and a yield of 92.3%. figure 1 Is the infrared spectrum analysis of the product, and the analysis results are as follows: IR (cm -1 ): 3399.27 (O-H), 2968.96, 2923.94 (-CH 3 、-CH 2 -), 1667.35 (C=N), 1489.04, 1419.20 (thiadiazole ring skeleton), 1265.86 (O-H), 1119.02, 1052.00 (C-O),...

Embodiment 2

[0037] Take 7.5 g (0.05 mol) of 2,5-dimercapto-1,3,4-thiadiazole in a 150 ml three-necked flask, and add 50 ml of tetrahydrofuran as a solvent. After stirring at room temperature until uniformly mixed, 18.4 g (0.1 mole) of dodecane oxide was slowly added dropwise. After the dropwise addition was completed, the temperature was raised to 80° C. to react for 24 hours. After the reaction, cool to room temperature, filter the reaction solution to remove insoluble matter, and then distill off the organic solvent to obtain the extreme pressure antiwear agent containing thiadiazole derivatives containing hydroxy. The product 2,5-bis(2'-hydroxydodecyl)mercapto-1,3,4-thiadiazole has a mass of 24.5 grams and a yield of 94.6%. figure 2 Is the infrared spectrum analysis of the product, and the analysis results are as follows: IR (cm -1 ): 3428.68 (O-H), 2920.83, 2851.26 (-CH 3 、-CH 2 -), 1642.36 (C=N), 1384.75 (-CH 3 ), 1068.25 (C-O), 719.75 (C-S). Figure 4 Be the proton nuclear ma...

Embodiment 3

[0041] This example is an elemental analysis of a sample. Table 1 has listed the elemental analysis result of embodiment 1~2. From the elemental analysis results in Table 1, it can be seen that the measured values ​​of C, H, N, and S elements of all target compounds and the theoretical values ​​calculated according to the molecular formula basically meet the requirements of grease additives, and the absolute error is within the allowable range. It can be confirmed that the obtained compound is the target compound.

[0042] Table 1 elemental analysis results

[0043]

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Abstract

The invention provides a hydroxy-containing thiadiazole derivative. The hydroxy-containing thiadiazole derivative has a structural formula shown in the specification, R in the structural formula is also shown in the specification, and R1 and R2 in the formula of R are respectively independently selected from C1-C30 straight-chain or branched-chain or C3-C30 cycloalkyl groups. The introduction of a hydroxy-containing oil-soluble carbon chain into the hydroxy-containing thiadiazole derivative makes the hydroxy-containing thiadiazole derivative well compatible with grease, and the hydroxy group can be effectively adsorbed by the surface of a metal, and can enhance the extreme pressure wear resistance.

Description

technical field [0001] The invention relates to an organic compound and its preparation method, in particular to a hydroxy-containing thiadiazole derivative, its preparation method and its application as an extreme pressure antiwear agent. Background technique [0002] Grease (oil) can reduce friction and wear during mechanical operation, prevent gluing, improve mechanical efficiency, reduce energy consumption, and prolong mechanical life, so it is widely used in various sectors of the national economy. Mineral-based grease (oil) has poor degradation ability in the natural environment, and if it accumulates in the environment, it will cause great pollution to the living environment of animals, plants and humans. Foreign countries began to study environmentally friendly lubricants in the 1970s, and the development speed has been more rapid in the past ten years. So far, a large number of mature products have come out. The research on environment-friendly lubricants started ...

Claims

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Application Information

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IPC IPC(8): C10M135/36C07D285/125C10N30/06
Inventor 水琳申宝武周轶张国茹徐魏陈琳宋朝新孟震英
Owner CHINA PETROLEUM & CHEM CORP
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