Preparation method of thioether sterically hindered phenol antioxidant

A technology of sterically hindered phenol and antioxidant is applied in the field of preparation of thioether type sterically hindered phenol antioxidant, which can solve the problems of difficulty in realizing industrial application, low conversion rate of effective products, complicated operation process, etc., and achieves easy separation. , the effect of short production cycle and simple synthesis process

Active Publication Date: 2020-08-04
XINXIANG RICHFUL LUBE ADDITIVE CO LTD
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  • Summary
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Problems solved by technology

[0010] 1. The effective product conversion rate of patents US4085132 and US4228297 is low, and the requirements must be purified by solvents. When the reaction mixture is crystallized and separated, the separation effect is poor, and the product yield is only about 50%, which is difficult to realize industrial application
[0011] 2. Patent CN102050768A uses a tin compound as a catalyst. After the reaction, acetic acid needs to be added to destroy the catalyst, and then crystallized, filtered, and dried to obtain the product. The operation process is cumbersome, and the solvent needs to be recovered and processed. The production cost is high and it is not conducive to Environmental friendly

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  • Preparation method of thioether sterically hindered phenol antioxidant

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[0037] For this reason, the present invention provides a kind of preparation method of thioether type hindered phenolic antioxidant, this method selects solid alkali as catalyst, while ensuring product purity, does not need to carry out crystallization purification to reaction mixture, directly cooling can obtain Sulfide-type hindered phenolic antioxidant products, the product yield is significantly improved. The solid base catalyst is easy to separate from the product, reusable and environmentally friendly. The process for synthesizing ethyl 2,2-thiobis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] has simple operation, significantly reduced production cost and easy industrial application.

[0038] specific:

[0039] like figure 1 As shown, the present invention provides a kind of preparation method of sulfide type hindered phenolic antioxidant, comprising:

[0040] Step 1, the first stage: 3-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl propionate and thiodiglycol are sub...

Embodiment 1

[0060] The present invention provides a kind of preparation method of sulfide type hindered phenolic antioxidant, comprising:

[0061] Add 58.98g (0.202mol) 3-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl propionate, 1.18g (2% of the mass of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate)KOH / Al 2 o 3 Catalyst, replace the air in the reaction system with nitrogen, heat the system to 120 °C, add 12.2 g (0.1 mol) of thiodiglycol in four times, and the time interval between each addition of thiodiglycol is 30 minutes. After feeding, the temperature was raised to 160°C, and the temperature was maintained at 160±5°C for 30 minutes. Turn on the vacuum pump to increase the vacuum degree in the flask (vacuum degree-0.09MPa), keep the reaction for 2 hours, and remove the by-product methanol generated by the reaction. After the reaction, raise the temperature to 170°C, maintain 170±5°C for 30 minutes under reduced pressure, then open the nitrogen valve to purge for 10 minutes, al...

Embodiment 2

[0062] Embodiment 2 (change feed ratio):

[0063] The present invention provides a kind of preparation method of sulfide type hindered phenolic antioxidant, comprising:

[0064] 3-(3,5-di-tert-butyl-4-hydroxyl phenyl) the charging capacity 58.98g (0.202mol) of methyl propionate in embodiment 1 is changed into 61.32g (0.21mol), all the other parts and embodiment 1 remained the same, and the product 2 was obtained in 99.5% yield and 96.7% purity.

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Abstract

The invention discloses a preparation method of a thioether sterically hindered phenol antioxidant, which comprises the following steps: a first stage: carrying out transesterification on 3-(3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate and thiodiglycol under the action of a solid base catalyst; a second stage: removing by-product methanol under reduced pressure; and a third stage, alternately removing unreacted raw materials by nitrogen purging and pressure reduction, cooling, filtering, and collecting the solid base catalyst to obtain the target product. The synthesis process is simple, solvent crystallization purification, drying and other operations do not need to be conducted on a reaction mixture, and the product can be obtained through direct cooling; the production period is short, the later solvent waste liquid treatment is reduced, and the production cost is obviously reduced.

Description

technical field [0001] The invention relates to the technical field of antioxidants, in particular to a preparation method of a sulfide type hindered phenolic antioxidant. Background technique [0002] Lubricating oil is affected by light, oxygen, and heat during use, and oxidized and deteriorated to form ketones, aldehydes, organic acids, etc., causing corrosion of equipment lubrication parts; at the same time, the above-mentioned oxidized substances will further polymerize to form sludge, paint film, etc. Lubrication and heat dissipation of the equipment, and too much sludge can easily cause the piston ring to stick and block the oil circuit. In order to inhibit the oxidative deterioration of lubricating oil and prolong the service life of lubricating oil, it is necessary to add a certain amount of antioxidant. [0003] Currently, zinc dialkyldithiophosphate (ZDDP) is a commonly used antioxidant in lubricating oils. In recent years, in order to improve the thermal effici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/28C07C319/20C07C323/12
CPCC07C319/28C07C319/20C07C323/12
Inventor 王倩倩徐坤范金凤
Owner XINXIANG RICHFUL LUBE ADDITIVE CO LTD
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