Alkyl acetamidobenzotriazole derivative lubricating oil additive and preparation method thereof

A technology of benzotriazole and lubricating oil additives, which is applied in the field of alkylacetamidobenzotriazole derivative lubricating oil additives and its preparation, can solve problems such as environment and health, and achieve good Extreme pressure and anti-wear properties, mild reaction conditions, cheap and easy-to-obtain raw materials

Inactive Publication Date: 2017-12-29
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The molecular design of traditional lubricating oil additives is mainly to meet the performance of the additives, and less consideration is given to factors such as the environment and health. Most of the molecular structures contai...

Method used

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  • Alkyl acetamidobenzotriazole derivative lubricating oil additive and preparation method thereof
  • Alkyl acetamidobenzotriazole derivative lubricating oil additive and preparation method thereof
  • Alkyl acetamidobenzotriazole derivative lubricating oil additive and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 0.1mol (12.9g) di-n-butylamine, 0.1mol (12.2g) 4-dimethylaminopyridine (DMAP) and 75mL chloroform to a 250mL three-necked flask, add dropwise under ice bath (0℃~5℃) Chloroacetyl chloride 0.1mol (11.3g), stirred and reacted for 3h. After the reaction, the reaction solution was washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove the solvent to obtain N,N-dibutyl-2-chloroacetamide.

[0037] Add 0.1 mol (11.9 g) benzotriazole, 0.1 mol (4.0 g) NaOH, 100 mL ethanol to a 250 mL three-necked flask. At room temperature, add N,N-dibutyl-2-chloride dissolved in 20 mL tetrahydrofuran dropwise Acetamide, after stirring for 1.5 hours, the temperature was raised and refluxed for 3.5 hours. After the reaction, it was cooled to room temperature, the insoluble matter was removed by filtration, the solvent was removed from the filtrate, and the silica gel column chromatography was used for separation...

Embodiment 2

[0039] Add 0.1mol (18.5g) di-n-hexylamine, 0.1mol (12.2g) 4-dimethylaminopyridine (DMAP), 75mL chloroform to a 250mL three-necked flask, add chlorine dropwise under ice bath (0℃~5℃) Acetyl chloride 0.1mol (11.3g), stirred and reacted for 3h. After the reaction, the reaction solution was washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove the solvent to obtain N,N-dihexyl-2-chloroacetamide.

[0040] Add 0.1 mol (11.9 g) benzotriazole, 0.1 mol (4.0 g) NaOH, and 100 mL ethanol to a 250 mL three-necked flask. At room temperature, add N,N-dihexyl-2-chloroethyl dissolved in 20 mL tetrahydrofuran dropwise After stirring for 1.5h, the amide was heated and refluxed for 3.5h. After the reaction, it was cooled to room temperature, the insoluble matter was removed by filtration, the solvent was removed from the filtrate, and the silica gel column chromatography was used for separation and purification to...

Embodiment 3

[0042] Add 0.1mol (24.1g) di-n-octylamine, 0.1mol (12.2g) 4-dimethylaminopyridine (DMAP), 75mL chloroform into a 250mL three-necked flask, dropwise under ice bath (0℃~5℃) 0.1mol (11.3g) of chloroacetyl chloride was added, and the reaction was stirred for 3h. After the completion of the reaction, the reaction solution was washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove the solvent to obtain N,N-dioctyl-2-chloroacetamide.

[0043] Add 0.1 mol (11.9 g) benzotriazole, 0.1 mol (4.0 g) NaOH, and 100 mL ethanol to a 250 mL three-necked flask. Add N,N-dioctyl-2-chloride dissolved in 20 mL tetrahydrofuran at room temperature. Acetamide, after stirring for 1.5 hours, the temperature was raised and refluxed for 3.5 hours. After the reaction, it was cooled to room temperature, the insoluble matter was removed by filtration, the solvent was removed from the filtrate, and the silica gel column chromato...

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Abstract

The invention discloses a biodegradable alkyl acetamidobenzotriazole derivative lubricating oil additive which does not contain sulfur, phosphorus, halogens and metal elements as well as a preparation method and application thereof. The preparation method comprises the following steps: under the action of alkali, performing amidation on alkyl amine and chloroacetyl chloride to obtain alkyl chloroacetamide; and then performing a nucleophilic substitution reaction with benzotriazole to obtain a target compound of a formula I. The preparation method disclosed by the invention is simple in preparation method, mild in process condition, easily available in raw material, low in preparation cost and high in synthetic yield. The novel alkyl acetamidobenzotriazole derivative can be independently used as an extreme pressure anti-wear corrosion-resistant additive of lubricating oil, also can be used with other lubricating oil additives in a compound manner, also can be used in common working conditions and high-temperature working conditions, can improve the bearing capacity of basic oil obviously and improve the anti-wear performance, and is the lubricating oil additive which is environmentally friendly and multi-functional. The formula I is as shown in the specification.

Description

Technical field: [0001] The invention relates to an alkylacetamidobenzotriazole derivative lubricating oil additive and a preparation method thereof. Such derivatives can be widely used in the fields of energy, environment, material science and the like, and are particularly suitable for use as a lubricating oil additive. Background technique: [0002] Traditional lubricating oil additives are mainly designed to meet the performance of the additives in their molecular design, and few factors such as environment and health are considered. Most of their molecular structures contain sulfur, phosphorus, halogen, metal elements and other elements harmful to the environment and health. , And now these traditional lubricant additives are facing severe challenges to the environment, ecology and human health. Modern lubrication technology has developed from focusing only on use efficiency to simultaneously focusing on the duality of use efficiency and ecological efficiency. The developmen...

Claims

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Application Information

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IPC IPC(8): C07D249/18C10M133/44C10N30/06C10N30/08C10N30/12
CPCC07D249/18C10M133/44C10M2215/223C10N2030/06C10N2030/08C10N2030/12C10N2030/41C10N2030/42C10N2030/43C10N2030/45C10N2030/64
Inventor 韩利芬戴康徐赵鸿斌曹华鲁浩廖俊旭官彩霞胡嘉漫
Owner DONGGUAN UNIV OF TECH
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