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A kind of bis-(2-aminoacetyl)-piperazine amide derivative lubricating oil additive and its preparation method

The technology of lubricating oil additive and aminoacetyl is applied in the field of bis-piperazine amide derivative lubricating oil additive and its preparation, and achieves the effects of good extreme pressure, anti-wear and friction reduction, simple preparation process and mild reaction conditions.

Inactive Publication Date: 2019-06-04
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The molecular structure of traditional lubricating oil additives mostly contains sulfur, phosphorus, halogen, metal elements and other elements that are harmful to the environment or health, which has certain limitations

Method used

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  • A kind of bis-(2-aminoacetyl)-piperazine amide derivative lubricating oil additive and its preparation method
  • A kind of bis-(2-aminoacetyl)-piperazine amide derivative lubricating oil additive and its preparation method
  • A kind of bis-(2-aminoacetyl)-piperazine amide derivative lubricating oil additive and its preparation method

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0033] Preparation of Intermediate 1:

[0034] Add 8.6g of piperazine, 150mL of chloroform and 100mL of saturated potassium carbonate aqueous solution into a 500mL three-neck flask, add 24.8g of chloroacetyl chloride dropwise under ice cooling, and stir at room temperature for 3h. Stop the reaction, transfer the reaction solution to a separatory funnel, separate the organic phase, wash twice with 1M hydrochloric acid solution, wash three times with saturated brine, dry over anhydrous magnesium sulfate, filter, and remove the organic solvent to obtain Intermediate 1.

Embodiment 1

[0036] Add 15.5g of di-n-butylamine, 11.9g of intermediate 1, 12.6g of sodium bicarbonate and 100mL of acetonitrile into a 250mL three-necked flask, and react at 65°C for 8h. Stop the reaction, cool to room temperature, filter to remove insoluble matter, remove the solvent by rotary evaporation, dissolve with dichloromethane, wash with saturated brine, dry over anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation of the filtrate to obtain 19.3 g of a light yellow liquid. The rate is 91.0%. 1 H NMR (400MHz, CDCl 3 ,TMS,ppm)δ:3.72–3.56(m,8H),3.26(s,4H),2.45(dd,J=12.4,5.7Hz,8H),1.47–1.36(m,8H),1.29(dd, J=14.5,7.2Hz,8H),0.93–0.88(m,12H).MALDI-TOF-MS,m / z:calcd for C 24 h 48 N 4 o 2 [M+1] + :425.378,found:425.355.

Embodiment 2

[0038] Add 27.0g of dioctylamine, 11.9g of intermediate 1, 12.6g of sodium bicarbonate and 100mL of acetonitrile into a 250mL three-necked flask, and react at 65°C for 8h. Stop the reaction, cool to room temperature, remove the insoluble matter by filtration, remove the solvent by rotary evaporation, dissolve with dichloromethane, wash with saturated brine, dry over anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation of the filtrate to obtain 29.4 g of light yellow liquid. The rate is 90.7%. 1 H NMR (400MHz, CDCl 3 ,TMS,ppm)δ:3.60(dd,J=24.6,15.4Hz,8H),3.23(s,4H),2.40(s,8H),1.24(s,48H),0.85(s,12H).MALDI -TOF-MS, m / z: calcd for C 40 h 80 N 4 o 2 [M+1] + :649.628,found:649.735.

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Abstract

The invention discloses a novel green multifunctional bi-(2-amidoacetyl)-piperazine amides derivative lubricant additive and a preparation method thereof. The preparation method specifically comprises the following steps: under the action of alkaline, firstly executing the amidation to piperazine and chloroacetyl chloride so as to obtain bi-(chloracetyl)-piperazine amide, and executing the nucleophilic substitution with corresponding amine to obtain a target compound as shown in the formula I. The preparation method is simple, the technological conditions are moderate, the raw materials are easily obtained, the synthesis cost is low, and the yield is high. The novel nitrogen-enriched bi-(2-amidoacetyl)-piperazine amides derivative can be exclusively used as a multifunctional additive of lubricating oil, or compounded to be used as the additive of other lubricating oil. The novel green multifunctional bi-(2-amidoacetyl)-piperazine amides derivative lubricant additive can be used for the general working conditions and the high-temperature working condition environment, is capable of remarkably improving the extreme pressure wear-resistant antifriction property of base oil and effectively improving the corrosion resistance of the base oil, and is a green biodegradable multifunctional lubricant additive.

Description

Technical field: [0001] The invention relates to a bis-(2-aminoacetyl)-piperazine amide derivative lubricating oil additive and a preparation method thereof. The derivative can be widely used in the fields of energy, environment, material science and the like, and is especially suitable for use as Lubricant additives. Background technique: [0002] Friction is an unavoidable natural phenomenon. The fuel used to reduce the friction and wear of mechanical parts accounts for about 1 / 3 of the total fuel consumption. In addition, friction will also cause useless loss of mechanical parts, shorten machine life, reduce Mechanical efficiency. In order to reduce friction and reduce wear, lubricating oil is usually added, and in order to improve the performance of lubricating oil, appropriate additives are added to lubricating oil. Most of the molecular structures of traditional lubricating oil additives contain elements harmful to the environment or health, such as sulfur, phosphoru...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185C07D295/192C07D295/215C10M133/40
CPCC07D295/185C07D295/192C07D295/215C10M133/40C10M2215/221
Inventor 韩利芬戴康徐赵鸿斌曹华鲁浩张文涛陆建雄黎晓莉
Owner DONGGUAN UNIV OF TECH
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