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Double thiadiazole derivative and preparation method thereof

A technology of bisthiadiazole and derivatives, applied in lubricating compositions, petroleum industry, additives, etc., to achieve the effects of good solubility and excellent extreme pressure

Active 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 alkylbisthiadiazole derivatives prepared by the two-step method of the present invention has not been reported in the literature and patents at home and abroad

Method used

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  • Double thiadiazole derivative and preparation method thereof
  • Double thiadiazole derivative and preparation method thereof
  • Double thiadiazole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 15.0g of 2,5-dimercapto-1,3,4-thiadiazole (0.1mol) and 80ml of ethyl acetate into a 500ml four-neck flask equipped with a reflux condenser and a thermometer, stir to dissolve, and add dropwise at 20°C 4.0g NaOH (0.1mol) aqueous solution 20mL, dropwise time is 10min, then add 0.3g tetrabutylammonium bromide (0.001mol) as catalyst, drop 13.7g (0.1mol) bromobutane at 20°C, The dropping time is 30min. After the dropping is completed, the temperature is gradually raised to 76°C for reflux reaction for 4h. After the reaction is completed, it is cooled to room temperature and filtered to obtain light yellow solid powder 2-thiobutyl-5-mercapto-1,3,4 - Thiadiazoles.

Embodiment 2

[0040] Add 15.0g of 2,5-dimercapto-1,3,4-thiadiazole (0.1mol) and 80ml of ethanol into a 500ml four-neck flask equipped with a reflux condenser and a thermometer, stir to dissolve, and add 4.4g of NaOH dropwise at 20°C (0.11mol) aqueous solution 21mL, dropwise time is 20min, then add 0.3g tetrabutylammonium bromide (0.001mol) as catalyst, drop 14.9g (0.1mol) chlorooctane at 20 ℃, dropwise time After the dropwise addition, gradually raise the temperature to 76°C for reflux reaction for 6 hours. After the reaction, cool to room temperature and filter to obtain light yellow solid powder 2-thiooctyl-5-mercapto-1,3,4-thiadiol azole.

Embodiment 3

[0042] Add 20.5g of 2-thiobutyl-5-mercapto-1,3,4-thiadiazole (0.1mol) synthesized in Example 1 in a 500ml four-necked flask equipped with a reflux condenser and a thermometer, and use 75ml of distilled water as The solvent was stirred and reacted, 13.6g of oxidant 0.12mol hydrogen peroxide (30%) was added dropwise, the dropping time was controlled at 10-15min, and then the temperature was raised to reflux for 6h. After the reaction, the product was extracted with petroleum ether, poured out and washed with water To neutrality, dry with anhydrous sodium sulfate and distill off the solvent to obtain a light yellow liquid product bis-5,5'-dithiobis-(1,3,4-thiadiazole-2-thiobutyl) additive. The S content of the product is 45.44%, and the theoretical S content is 46.82%.

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Abstract

The invention discloses a double thiadiazole derivative lubricant additive and a preparation method thereof, wherein 2,5-dimercapto-1,3,4-thiadiazole is adopted as a raw material, the 2,5-dimercapto-1,3,4-thiadiazole and halogenated alkane are subjected to a nucleophilic substitution reaction under a catalyst effect to generate monoalkyl thiadiazole, and the monoalkyl thiadiazole is subjected to a coupled reaction under an oxidizing agent effect to obtain bis-5,5'-dithiodi-(1,3,4-thiadiazole-2-thioalkyl) additive, wherein the additive is characterized in that excellent extreme pressure property and antifriction property are provided for the lubricant with the additive, and the additive can be adopted as a lubricant additive to be separately used or is compounded with other additives to be used, and is applicable for industrial lubricating oils and lubricating greases.

Description

[0001] Technology area [0002] The invention relates to a bithiadiazole derivative lubricant additive, a preparation method thereof, and use characteristics thereof, belonging to the field of lubricants. Background technique [0003] Since the lubricant is in use, the protruding parts of the surfaces in contact with each other, or the rough surface will form friction, when the friction surfaces start to interact, the friction is initially reduced by the elastohydrodynamic lubricating film, and in extreme cases, the direct surface contact, which increases friction and the possibility of surface damage. In this case, antiwear and extreme pressure additives are added to the lubricant to reduce wear and prevent seizure. Commonly used extreme pressure additives contain organic compounds such as S, P, and Cl, which can react with metals at high temperatures to form lubricating substances, and provide lubrication under severe conditions. Some current studies have shown that thiadi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/08C10M135/36C10N30/06C10N30/10
Inventor 薛卫国李久盛李建明
Owner PETROCHINA CO LTD
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