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Phosphorothioate type antiwear agent

A compound and straight-chain technology, applied in additives, lubricating compositions, petroleum industry, etc., can solve problems such as poor thermal stability, clogged filters, high acidity of water layer, etc., and achieve excellent anti-rust performance

Active Publication Date: 2017-01-11
XCMG CONSTR MACHINERY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the hydrolysis stability test of hydraulic oil (SH / T 0301-1993), the above-mentioned ashless anti-wear agent showed the advantage of less weight loss of copper sheet, but also showed the disadvantage of high acidity of the water layer
The high acidity of the water layer is unfavorable for the use of hydraulic oil, because once the hydraulic oil enters the water, too much acidic substance will easily deteriorate the oil
In addition, the thermal stability of ammonium phosphoric acid complex ester is poor, and it is easy to form sludge at high temperature, which can block the filter

Method used

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  • Phosphorothioate type antiwear agent
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  • Phosphorothioate type antiwear agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0049] Example 1 Diisooctyl dithiophosphoric acid-2-methyl-succinic acid dimethyl ester (AW-1)

[0050]

[0051] Under nitrogen protection, 70.8g of bis(2-ethylhexyl)dithiophosphoric acid was added to a 250ml four-necked reaction flask, heated to 100°C, and then 7.08g of p-toluenesulfonic acid was added as a catalyst, and then stirred and used 1.5 31.2 g of dimethyl itaconic acid was slowly added dropwise over a period of hours, and the reaction was continued to stir for 8 hours under nitrogen protection to obtain a crude product.

[0052] Separation and purification: the above crude product was extracted with 10wt% sodium carbonate aqueous solution and petroleum ether in turn, and the oil phase was dried with anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The liquid distilled under reduced pressure was separated by silica gel chromatography. The inner diameter of the chromatography column is 35 mm and the height is 400 mm, the adsorbent is ...

Embodiment 2 2

[0053] Example 2 Diisooctyl dithiophosphoric acid-2-methyl-succinic acid diethyl ester (AW-2)

[0054]

[0055] Under nitrogen protection, 70.8g of bis(2-ethylhexyl)dithiophosphoric acid was added to a 250ml four-necked reaction flask, heated to 100°C, and then 7.08g of p-toluenesulfonic acid was added as a catalyst, and then stirred and used 1.5 36.8 g of itaconic acid diethyl ester was slowly added dropwise over a period of hours, and the reaction was continued to stir for 9 hours under nitrogen protection to obtain a crude product.

[0056] Separation and purification: the above crude product was washed with 10wt% sodium carbonate aqueous solution, then extracted with petroleum ether, and the oil phase was dried with anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The liquid distilled under reduced pressure was separated by silica gel chromatography. The inner diameter of the chromatography column is 35 mm and the height is 400 mm, the ads...

Embodiment 3 2

[0057] Example 3 Diisooctyl dithiophosphoric acid-2-methyl-succinic acid dibutyl ester (AW-3)

[0058]

[0059] Under nitrogen protection, 70.8g of bis(2-ethylhexyl)dithiophosphoric acid was added to a 250ml four-necked reaction flask, heated to 100°C, and then 7.08g of p-toluenesulfonic acid was added as a catalyst, and then stirred and used 1.5 48.0 g of itaconic acid dibutyl ester was slowly added dropwise over a period of 10 hours, and the reaction was then continued to stir for 10 hours under nitrogen protection to obtain a crude product.

[0060] Separation and purification: the above crude product was washed with 10wt% sodium carbonate aqueous solution, then extracted with petroleum ether, and the oil phase was dried with anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The liquid distilled under reduced pressure was separated by silica gel chromatography. The inner diameter of the chromatography column is 35 mm and the height is 400 mm...

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Abstract

The invention relates to a phosphorothioate type antiwear agent, and in particular relates to a compound of formula I, wherein R1 and R2 are independently selected from C1-12 straight or branched chain alkyl groups, R3 and R4 are each independently selected from the group consisting of H, C1-12 straight or branched chain alkyl groups, C1-12 straight or branched chain alkyloxy groups, and the C1-12 straight or branched chain alkyl groups and the C1-12 straight or branched chain alkyloxy groups are optionally mono-substituted or polysubstituted by substitutes selected from the group consisting of a halogen, C1-4 alkyl groups, halogen-substituted C1-4 alkyl groups, C1-4 alkoxy groups, halogen-substituted C1-4 alkoxy groups, hydroxyl groups, cyano groups, nitro groups, amino groups or trifluoromethyl groups. The compound as a hydraulic oil or lubricating oil additive exhibits excellent rust resistance, good antiwear property, thermal stability, filtration and hydrolytic stability.

Description

technical field [0001] The invention belongs to the field of lubricating oil additives, in particular to a phosphorothioate type antiwear agent. Background technique [0002] Zinc dialkyldithiophosphate (ZDDP), as a multifunctional additive with anti-oxidation, anti-wear and anti-corrosion properties, is widely used in hydraulic oil. However, ZDDP will cause heavy metal pollution to the environment; and when it is polluted by water during use, ZDDP is easy to hydrolyze and produce sludge to block the filter; in addition, ZDDP is also corrosive to copper. [0003] People have been trying to use ashless antiwear agents to replace the application of ZDDP in hydraulic oils. At present, the widely used ashless antiwear agents mainly include tricresyl phosphate (T306), ammonium thiophosphate complex ester, triphenylsulfur Phosphate (T309), etc. In the hydraulic oil hydrolysis stability test (SH / T 0301-1993), the above-mentioned ashless anti-wear agent showed the advantage of les...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/17C10M137/10C10N30/06C10N30/12C10N30/10C10N40/08C10N40/04
Inventor 郑东东王月行闫龙龙
Owner XCMG CONSTR MACHINERY
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