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Thiocarbamate-containing thiadiazole derivative, and preparation method and use thereof

A technology containing thiocarbamate and thiadiazole derivatives, which is applied in lubricating compositions, petroleum industry, additives, etc., and can solve unseen problems

Active Publication Date: 2014-08-06
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] After investigation, there is no domestic and foreign literature report on the synthesis of anti-wear additives using 2,5-dimercapto-1,3,4 thiadiazole and thiocarbamate as raw materials

Method used

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  • Thiocarbamate-containing thiadiazole derivative, and preparation method and use thereof
  • Thiocarbamate-containing thiadiazole derivative, and preparation method and use thereof
  • Thiocarbamate-containing thiadiazole derivative, and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 30.0g of 2,5-dimercapto-1,3,4-thiadiazole into 100mL of reaction medium toluene, add 8.0g of sodium hydroxide catalyst under stirring, after heating to 60°C, slowly add 152.0g of N,N' - Diisooctyldithiocarbamate ethyl chloride toluene solution, after the dropwise addition, the temperature was raised to 90°C, and the reaction was carried out for 5 hours. After cooling to room temperature, a small amount of insoluble matter was filtered off, and then washed with distilled water until neutral , evaporated to remove the solvent, and dried in vacuo to obtain a yellow oily liquid that is a thiadiazole derivative product containing thiocarbamate.

Embodiment 2

[0034] Add 15.0g of 2,5-dimercapto-1,3,4-thiadiazole into 100mL of reaction medium ethanol, add 10.1g of triethylamine catalyst under stirring, after heating to 60°C, slowly add 59.7g of N,N' - Di-n-butyldithiocarbamate methyl bromide benzene solution, after the dropwise addition, the temperature was raised to 75°C, and reacted for 4 hours. After cooling to room temperature, a small amount of insoluble matter was filtered off, and then washed with distilled water until neutral , evaporated to remove the solvent, and dried in vacuo to obtain a light yellow liquid that is a thiadiazole derivative product containing thiocarbamate.

Embodiment 3

[0036] Add 15.0g of 2,5-dimercapto-1,3,4-thiadiazole to 150mL of N,N'-dimethylformamide, add 8.4g of sodium bicarbonate catalyst under stirring, heat to 90°C, slowly Add dropwise 81.6g of N,N'-dioctyldithiocarbamate butyl chloride N,N'-dimethylformamide solution, after the dropwise addition, heat up to 155°C, react for 6 hours, and wait to cool to room temperature Finally, filter out a small amount of insoluble matter, then wash with distilled water until neutral, evaporate the solvent, and dry in vacuum to obtain a yellow liquid that is a thiadiazole derivative product containing thiocarbamate.

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PUM

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Abstract

The invention relates to a thiocarbamate-containing thiadiazole derivative. The derivative is 2,5-diN,N'-dialkyldithiocarbamate alkylthioether-1,3,4-thiadiazole, and has the structural formula defined in the description. A preparation method of the derivative comprises the steps of: adding 2,5-dimercapto-1,3,4-thiadiazole and N,N'-dialkyldithiocarbamate alkyl chloro-ester or N,N'-dialkyldithiocarbamate alkyl bromo-ester to a reaction medium, and adding a catalyst to the reaction medium at the same time, wherein the molar ratio of 2,5-dimercapto-1,3,4-thiadiazole to N,N'-dialkyldithiocarbamate alkyl chloro-ester or N,N'-dialkyldithiocarbamate alkyl bromo-ester is 1:2.0-1:2.3; carrying out a reaction for 1-10 hours at a temperature of 10-160 DEG C; removing the reaction medium by filtering and washing; and obtaining a thiocarbamate-containing thiadiazole derivative product by vacuum drying. The invention is characterized in that a thiocarbamate-based oil-soluble group, i.e. an extreme pressure antiwear group, is introduced into thiadiazole, so that the thiadiazole derivative is soluble in the base oil of a lubricant, thereby enabling the lubricant to have excellent extreme pressure antiwear performance.

Description

technical field [0001] The invention relates to an anti-wear additive for lubricating oil, in particular to a thiadiazole derivative containing thiocarbamate and its preparation and application. Background technique [0002] At present, 2,5-dimercapto-1,3,4-thiadiazole (DMTD) derivatives are widely used in the field of lubricating oil additives. It can well inhibit the corrosion of metals such as copper and stainless steel, and has certain Anti-oxidize effect. The most important application of DMTD derivatives is as an anti-wear additive for lubricants. S, N and other elements are active elements that increase the extreme pressure and anti-wear performance of lubricating oil. DMTD derivatives are heterocyclic compounds containing S and N elements, and it is a kind of mild lubricating oil additive, which can be combined with other functional additives It works great. [0003] The Chinese invention patent discloses a thiadiazole dimer additive with application number 008018...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/125C10M135/36C10N30/06
CPCC07D285/125C10M135/36C10M2219/106C10N2030/06
Inventor 官婷婷张东恒李韶辉
Owner PETROCHINA CO LTD
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