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Thioether-containing hindered phenol antioxidant and preparation method thereof

A hindered phenol antioxidant and sulfide-containing technology, which is applied in the field of lubricants to achieve outstanding anti-oxidation performance

Inactive Publication Date: 2013-09-25
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis process of the sulfide-containing hindered phenol ashless antioxidant prepared by the Mannich reaction in the present invention has not been reported in domestic literature and patents

Method used

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  • Thioether-containing hindered phenol antioxidant and preparation method thereof
  • Thioether-containing hindered phenol antioxidant and preparation method thereof
  • Thioether-containing hindered phenol antioxidant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Mix 20.6g (0.1mol) of 2,6-di-tert-butylphenol, 3.6g (0.12mol) of paraformaldehyde, and 20.4g (0.1mol) of isooctyl mercaptoacetate into a 500ml four-necked bottle, and use 80mlN, N-dimethylformamide was used as a solvent, and 0.2 g (0.002 mol) of catalyst triethylamine was added under stirring conditions, gradually heated to 120 ° C, and kept for reflux reaction for 7 hours. After the reaction was completed, the product was extracted with petroleum ether, washed with water for 3 ~5 times, and then distilled under reduced pressure to obtain a yellow-brown transparent liquid product. The S content of the product is 7.31%, and the theoretical S content is 7.55%. figure 1 It is the infrared spectrogram of (3,5-di-tert-butyl-4-hydroxyl-) benzylthioglycolate isooctyl that example 1 obtains, wherein 3642cm -1 Is the absorption peak of phenol-O-H; 883cm -1 Near = C-H deformation vibration (four-substituted -C-H vibration on the benzene ring); 494cm -1 The -S-stretching vibrat...

Embodiment 2

[0033] Mix 20.6g (0.1mol) of 2,6-di-tert-butylphenol, 12.2g (0.15mol) of formaldehyde solution (37%), and 14.8g (0.1mol) of n-butyl thioglycolate into a 500ml four-necked bottle, Using 80ml of ethyl acetate as a solvent, add 0.12g (0.001mol) of catalyst N,N-dimethylaniline under stirring conditions, gradually heat to 75°C, keep reflux reaction for 4 hours, after the reaction, extract the product with petroleum ether , washed with water for 3 to 5 times, and distilled under reduced pressure to obtain a reddish-brown transparent liquid product. The S content of the product is 8.62%, and the theoretical S content is 8.74%.

Embodiment 3

[0035] Mix 12.3g (0.1mol) of 2,6-dimethylphenol, 4.2g (0.14mol) of paraformaldehyde, and 20.4g (0.1mol) of isooctyl thioglycolate into a 500ml four-necked bottle, and use 80mlN, N - Dimethylformamide as a solvent, then add 0.2 g (0.002 mol) of triethylamine as a catalyst, gradually heat to 120 ° C under stirring conditions, keep reflux reaction for 6 hours, after the reaction, extract the product with petroleum ether, wash with water 3 to 5 times, and then distilled under reduced pressure to obtain a yellow-brown transparent liquid product. The S content of the product is 9.41%, and the theoretical S content is 9.44%.

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Abstract

The present invention provides a thioether bond structure-containing hindered phenol antioxidant and a preparation method thereof, wherein screen phenol, thiol ester and formaldehyde in a reaction medium are subjected to a reaction under a certain condition in the presence of a catalyst to obtain a thioether bond-containing hindered phenol antioxidant compound, wherein the compound has an excellent antioxidation performance in hydrogenation base oil, and can be adopted as a lubricating agent antioxidant to be separately used or is compounded with other additives to be used, and the antioxidant is applicable for internal combustion engine oils and industrial lubricating oils.

Description

technical field [0001] The invention relates to a sulfide-containing hindered phenol antioxidant, a preparation method and application characteristics thereof, and belongs to the field of lubricants. Background technique [0002] Antioxidant additives are a class of additives with a wide range of applications. With the stringent requirements of high-grade lubricating oils in terms of viscosity control, deposit reduction, and valve system wear reduction, higher requirements are placed on the performance of antioxidants. The use of ZDDP series anti-oxidant and anti-corrosion agents has been unable to meet the anti-oxidation performance of high-grade lubricating oils. Therefore, the development of new anti-oxidation additives such as various phenolic types, amine types, organic copper salts, and alkali metal salts has been rapidly developed. develop. [0003] In previous reports, sulfur-containing phenolic antioxidants were mostly used in rubber or plastics, and rarely used in...

Claims

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Application Information

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IPC IPC(8): C10M135/26C07C323/52C07C319/14C10N30/10
Inventor 薛卫国周旭光李建明
Owner PETROCHINA CO LTD
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