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Screen phenol-containing thiadiazole type antioxygen antiwear additive and preparation method thereof

A thiadiazole type, shielding phenol technology, applied in the direction of additives, petroleum industry, organic chemistry, etc., to achieve good solubility and excellent anti-oxidation effect

Inactive Publication Date: 2013-09-25
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis process of the anti-oxidation and anti-wear additives of thiadiazole derivatives containing shielding phenol prepared by the two-step method in the present invention has no identical reports in the literature and patents at home and abroad.

Method used

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  • Screen phenol-containing thiadiazole type antioxygen antiwear additive and preparation method thereof
  • Screen phenol-containing thiadiazole type antioxygen antiwear additive and preparation method thereof
  • Screen phenol-containing thiadiazole type antioxygen antiwear additive and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 15.0g 2,5-dimercapto-1,3,4-thiadiazole (0.1mol) and 80ml ethyl acetate into a 500ml four-neck flask equipped with a reflux condenser and a thermometer, stir to dissolve, and Add 20mL of 4.0g NaOH (0.1mol) aqueous solution dropwise for 10min, then add 0.3g tetrabutylammonium bromide (0.001mol) as a catalyst, add 13.7g (0.1mol) bromobutyl at 20°C dropwise Alkanes, the time for the dropwise addition is 30 minutes. After the dropwise addition, gradually raise the temperature to 76°C for reflux reaction for 4 hours. After the reaction, cool to room temperature and filter to obtain a pale yellow solid powder , 4-thiadiazole.

Embodiment 2

[0044] Add 20.5g 2-thiobutyl-5-mercapto-1,3,4-thiadiazole (0.1mol) synthesized by Example 1 in a 500ml four-necked flask equipped with a reflux condenser and a thermometer, while mixing and adding 20.6 g 2,6-di-tert-butylphenol (0.1mol), 3.6g paraformaldehyde (0.12mol), carry out stirring reaction with 75ml N,N-dimethylformamide as solvent, heat up to 120°C and add catalyst two n Butylamine 0.65g (0.005mol) was refluxed at 120-130°C for 5 hours. After the reaction, the product was diluted with a mixed solvent of petroleum ether and tetrahydrofuran, poured out and washed with water until neutral, dried with anhydrous sodium sulfate, and evaporated. The solvent was removed to obtain the product 2-(3,5-di-tert-butyl-4-hydroxy-benzyl)thio-5-butylthio-1,3,4-thiadiazole. The S content of the product is 21.69%, and the theoretical S content is 22.14%; the N content of the product is 6.56%, and the theoretical N content is 6.60%; the melting point of the product is 90°C. figure 1 It ...

Embodiment 3

[0046] Add 15.0g of 2,5-dimercapto-1,3,4-thiadiazole (0.1mol) and 80ml of ethanol into a 500ml four-necked flask equipped with a reflux condenser and a thermometer, stir to dissolve, and add dropwise at room temperature at 20°C 4.4g NaOH (0.11mol) aqueous solution 21mL, dropwise time is 20min, then add 0.3g tetrabutylammonium bromide (0.001mol) as a catalyst, add dropwise 14.9g (0.1mol) chlorooctane at 20°C, The dropwise addition time is 40min. After the dropwise addition, gradually raise the temperature to 76°C for reflux reaction for 6h. After the reaction, cool to room temperature and filter to obtain light yellow solid powder 2-thiooctyl-5-mercapto-1,3,4 - Thiadiazoles.

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Abstract

The invention discloses a screen phenol-containing thiadiazole type antioxygen antiwear additive and a preparation method thereof, wherein the chemical name of the additive is 2-(3,5-di-tert-butyl-4-hydroxy-benzyl)thio-5-alkylthio 1,3,4-thiadiazole. According to the preparation method, 2,5-dimercapto-1,3,4-thiadiazole is adopted as a raw material, the 2,5-dimercapto-1,3,4-thiadiazole and a halogenated alkane are subjected to a nucleophilic substitution reaction under a catalyst effect to generate monoalkyl thiadiazole, and the monoalkyl thiadiazole, formaldehyde and 2,6-di-tert-butylphenol are subjected to a condensation polymerization reaction under a catalyst effect to obtain 2-(3,5-di-tert-butyl-4-hydroxy-benzyl)thio-5-alkylthio 1,3,4-thiadiazole type lubricating oil multifunction additive, wherein the additive is characterized in that good oxidation resistance, extreme pressure property, wear resistance and corrosion resistance are provided for the lubricant with the additive, and the additive can be combined with other additives to provide good synergy effects, can be adopted to partly or completely replace ZDDP, and is applicable for internal combustion engine oils and industrial lubricating oils.

Description

technical field [0001] The invention relates to a thiadiazole-type anti-oxidation and anti-wear multifunctional additive containing shielding phenol, a preparation method and application characteristics thereof, and belongs to the field of lubricants. Background technique [0002] Lubricating oils will be oxidized and deteriorated during use due to factors such as ambient temperature, oxygen in the air, and metal catalysis, and produce alcohols, ketones, and acid compounds. These low-molecular-weight substances will further undergo polycondensation reactions to generate high-molecular-weight substances. The polymers in the lubricant will form deposits, resulting in increased oil viscosity, poor lubricating performance, increased wear, and even severe corrosion of mechanical equipment, greatly reducing the function of lubricating oil and shortening the service life of the oil. For most modern lubricating oils, antioxidant components must be added. The role of antioxidants is...

Claims

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Application Information

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IPC IPC(8): C10M135/36C07D285/125C10N30/10C10N30/06
Inventor 薛卫国李建明周旭光胡正厚李桂云
Owner PETROCHINA CO LTD
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