1,3,4-thiadiazole derivatives, preparing method thereof and applications of the derivatives

A thiadiazole derivative, thiadiazole technology, applied in the direction of lubricating composition, petroleum industry, additives, etc., can solve the problems that are not involved, and achieve easy realization, high yield, good performance of anti-friction and extreme pressure resistance Effect

Inactive Publication Date: 2016-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] None of the previously described lubricating oil additives has addressed the use of derivatives of 5-acetamido-2-mercapto-1,3,4-thiadiazole to solve the problems of friction reduction and extreme pressure resistance in lubricating oils

Method used

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  • 1,3,4-thiadiazole derivatives, preparing method thereof and applications of the derivatives
  • 1,3,4-thiadiazole derivatives, preparing method thereof and applications of the derivatives
  • 1,3,4-thiadiazole derivatives, preparing method thereof and applications of the derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of compound 5-acetylamino-2-thio-n-octyl-1,3,4-thiadiazole (T1).

[0035] Add 1.32g (10mmol) 5-amino-2-mercapto-1,3,4-thiadiazole and 0.84g (15mmol) KOH into a 50ml round bottom flask, add 1ml deionized water, stir until all solids disappear, add 1.94g (10mmol) n-octane bromide, 10ml absolute ethanol. When a large amount of white solid appeared in the reaction system, the reaction was continued for another 2 h. After the reaction, 30ml of water was added, suction filtered, washed with water, and dried. Recrystallized from 95% ethanol to obtain 5-amino-2-thio-n-octyl-1,3,4-thiadiazole as a white solid. Add 1.68g (10mmol) of 5-amino-2-thio-n-octyl-1,3,4-thiadiazole, 0.94ml (10mmol) of acetic anhydride, and 1.2ml of glacial acetic acid into a 50ml round bottom flask at 70°C Heat and stir in a water bath, and continue to react for 1 h when a large amount of white solid appears in the reaction system. Cool, filter with suction, wash with water, dry, ...

Embodiment 2

[0038] Example 2: Synthesis of 5-acetylamino-2-thiobenzyl-1,3,4-thiadiazole (T2).

[0039] Add 1.76g (10mmol) of 5-acetamido-2-mercapto-1,3,4-thiadiazole and 1ml deionized water into a 50ml round bottom flask, add 0.84g (15mmol) KOH to the system and stir until solid All disappear, add 2.27g (10mmol) benzyl chloride, 10ml absolute ethanol. When a large amount of white solid appeared in the reaction system, the reaction was continued for another 30 minutes. After the reaction, add 30ml of water, filter with suction, wash with water, dry, and recrystallize from absolute ethanol to obtain 1.97g of white needle-like crystals of 5-acetylamino-2-thiobenzyl-1,3,4-thiadiazole, The yield was 74.09%, and the melting point was 169-170°C.

[0040] The structural characterization results of 5-acetylamino-2-thiobenyl-1,3,4-thiadiazole (T2), the data are as follows:

[0041] T2: IR (KBr, cm -1 )v: 3162.24, 3034.42, 2919.48, 2790.54, 1694.00, 1566.76, 1496.84, 1454.25, 1374.30, 1044.15, 769...

Embodiment 3

[0042] Example 3: Synthesis of the compound n-octyl 5-acetylamino-1,3,4-thiadiazole-2-thioglycolate (T3).

[0043] Take 1.17g (6.7mmol) of 5-acetylamino-2-mercapto-1,3,4-thiadiazole, 0.48g (8.6mmol) of KOH, and 5ml of deionized water in a 50mL round bottom flask, and stir until all the solids are After the disappearance, 5 mL of an ethanol solution containing 1.38 g (6.7 mmol) of n-octyl chloroacetate was slowly added dropwise under an ice-water bath. After 1 h of addition, the mixture was stirred at room temperature for 4 h. Suction filtration, washing with water, drying, and recrystallization from anhydrous methanol yielded 1.75 g of white needle-like crystals with a yield of 76.09% and a melting point of 121-123°C.

[0044] The structural characterization results of n-octyl 5-acetylamino-1,3,4-thiadiazole-2-thioglycolate (T3), the data are as follows:

[0045] T3: IR (KBr, cm -1 )v: 3160.94, 2926.65, 2852.40, 2791.81, 1740.76, 1687.94, 1567.20, 1467.97, 1377.21, 1159.80, ...

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Abstract

The invention provides 1,3,4-thiadiazole derivatives, a preparing method thereof and applications of the derivatives. Structures of the derivatives are characterized through infrared spectroscopy and nuclear magnetic resonance. Antifriction and extreme-pressure resisting properties of the derivatives as 150 SN base oil additives are evaluated in an SRV testing machine. Results show that the synthesized compounds have a good lubricating property, can effectively improve antifriction and extreme-pressure resisting properties of lubricating oil, and are lubricating oil additives with good properties. The compounds are synthesized by adopting 5-amino-2-mercapto-1,3,4-thiadiazole as a raw material. A reaction process is simple and easy to implement. The product yield is high. The production cost can meet requirements on industrial production. In addition, the 1,3,4-thiadiazole compounds have good antifriction and extreme-pressure resisting properties when being adopted as lubricating additives, and can be used as antifriction and extreme-pressure resisting additives for lubricating oil.

Description

technical field [0001] The invention provides the synthesis of a class of 1,3,4-thiadiazole lubricating oil additive and its application as lubricating oil anti-friction and extreme pressure resistance agent. Background technique [0002] As we all know, zinc dialkyldithiophosphate (ZDDP) is a kind of multi-functional lubricating oil additive with excellent extreme pressure anti-wear, anti-oxidation and anti-corrosion properties and widely used. It is widely used in engine oil, hydraulic oil and in gear oil. However, with the continuous improvement of modern mechanical properties and increasingly stringent environmental requirements, higher requirements are placed on lubricating oil additives. Since ZDDP contains zinc element that can cause electrochemical corrosion and phosphorus element that is easy to poison the catalyst in the automobile exhaust treatment device, in order to meet the requirements of environmental protection, it has become the current tribology to find a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135C10M135/36C10N30/06
CPCC07D285/135C10M135/36C10N2030/06
Inventor 陈宏博宋春雪
Owner DALIAN UNIV OF TECH
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