SU540862A1 - 2.2 "Bis (diethanolamine) dialkyl (aryl) disulfides, as anti-friction and anti-seize and anti-wear additives for lubricants, and method for their preparation - Google Patents

Description

Vat is another solvent danethanolamine, such as dioxane. The reaction is carried out at reflux and, if necessary, with a trap (to collect possible unreacted hydrocarbons) for 1-10 hours. The time limit depends on the temperature, the intensity of mixing, and the activity of the starting dichlorodisulfide. The hemierature of the boiling point of the reaction mixture depends on the amount of water or dioxane taken. After refluxing, the reaction mass is cooled to 60, approximately half the amount of solvent disulfide (benzene, benzene) is poured into the reaction, stirred, aqueous diethanolamine (which is subsequently regenerated and used in the following syntheses) is separated and separated. the funnel, the solution is boiled with a Dean and Stark type trap until complete dehydration (1 - 2 hours), cooled, filtered, then the solvent is distilled off under vacuum at a temperature of up to 10U-120 ° C. Example 1: A 0.5 l three-necked flask equipped with a stirrer, a thermometer and a dropping funnel is charged with 120 g of a technical fraction of a-olefins with a boiling point of 140-ISO C and an iodine number of 170 g L / VO HIB for 30 minutes with stirring, 54 are added dropwise g of sulfur monochloride. The reaction mass is kept for 2 hours at a temperature of 50 ± 2 ° C and left overnight, ha the next day the resulting 2.2-dichlorodialkyl disulfide is placed in a 1 liter flask equipped with a stirrer, a thermometer and a trap to collect unreacted hydrocarbons under reflux, a mixture of 200 g of diethanolamine and 200 ml of water and boiled for 1 hour at a temperature of 105--, then 37 g of distilled unreacted hydrocarbons and BO ml of water are drained from the trap, and then boiled for another 7 hours at a temperature of intensive mixing. The reaction mass is cooled to 60 ° C, 100 ml of gasoline is added, stirred for 5 minutes, aqueous diethanolamine is poured, and the gasoline solution is boiled for 1 hour with a Dean and Stark trap to separate the water, and then the gasoline is distilled off at a water pump ( residual pressure 0.3 atm) at temperatures up to 110 ° C. 96 g are obtained (yield based on the starting unsaturated compound is 827 °)

lightly transparent brown liquid.

The hydroxyl number is 276 mg CCP / g, the viscosity 149 eats at 50 ° С, the S content is 16.2%, N is 3.92%, and C1 is 0.0%. The product is unlimited soluble in mineral oils.

Example 2. p, p-Dichlorodialkyl disulfide, obtained according to a known method 1 (so-called additive HCO-200) and containing S 14%, C1 12.5% with a viscosity of 15 eats at 50 ° С,

then left overnight to complete the reaction. The next day, a solution of 420 g (4 mol) of diethanolamine and 200 ml of water is added, the dropping funnel is replaced with a reflux condenser and the reaction mixture is boiled at a temperature of 108-110 ° C for

4 hours, after which it is cooled to 60 ° C, 150 ml of benzene is added, stirred

5 min, the aqueous diethanolamine is separated in a separating funnel, washed with water after the amount of I kg is loaded into a three-neck colou with a capacity of 3.5 liters, equipped with a stirrer, a thermometer and a reflux condenser, a mixture of 1 l of diethanolamine and ZiO ml is added and boiled vigorous stirring for 3 hours. The boiling point of the mixture rises at the beginning to 127 ° C at the end of the exposure. The reaction mass is cooled to / and C, is added and, 5 liters of gasoline, is stirred for 5 minutes, an aqueous diethanolamine layer is separated in a separatory funnel, and the gasoline layer is boiled with a trap for 1 hour until complete dehydration. Then the solution is cooled, filtered through a filter paper and gasoline is distilled off under vacuum (residual pressure 0.2 atm) at a temperature of up to. Get I kg (81% calculated on the original dichlorodisulfnd) product containing S 15,07o, N 3.5%, C1 0 ,. The hydroxyl number is 202 mg KOP / G, the viscosity 152 eats at. The product is a clear, brown liquid that dissolves indefinitely in mineral oils. Example 3. In a round-bottom flask with a capacity of 1 l, 207.5 g (0.5 mol) p of rdichlorodidecyl disulfide, obtained from mission-1 and sulfur monochloride according to the procedure described in example 1, 315 g (3 mol) of diethanolamine and lUO ml of water is heated under vigorous stirring until boiling and at this temperature () is boiled for 5 hours. The subsequent treatment is carried out as in Example 1. 250 g (90.5%, based on the starting material, 3-p-dichlorodidecyl disulfide) of the product, which is a light brown transparent liquid with a viscosity of 178, are eaten at. Found,%: S 11.58; N 5.01; C1 0.0. Hydroxyl number 400 mg CPC / g. Calculated, 7o: s 11.60; N 5.07, C1 0.0. Hydroxyl number 406 mg KOP / g. Gross formula С28ПБО1 2О482 - 2,2-bis (diethanolamia) -decidyl disulfide. The product is unlimited soluble in mineral oils. Example 4. In a 1-liter round-bottomed flask equipped with a stirrer, an addition funnel and a thermometer, 104 g (1 mol) of freshly distilled styrene was placed and, under vigorous stirring and cooling with an ice-water bath, in 20 min, 67.5 g (0, 5 mol) of sulfur monochloride. The reaction mass is kept for 1 hour at room temperature, then for 2 hours at 50 ± 3 ° С,

of which is boiled with a Dean and Sgarka trap for 1.5 hours until complete dehydration.

After distillation of benzene under vacuum (0.2 atm). At a temperature of up to 100 ° C, 341 g (71% based on the taken styrene) of a clear, viscous, clear-brown product are obtained.

Found,%: S 13.2; N 5.75; CI 0.0 The hydroxyl number is 461 mg KOH / g.

Calculated,%: S 13.35; N 5.83; C1 0.0. The hydroxyl number is 466 mg KOH / g.

Gross forma and C24H36N2O4S2 - 2,2-bis (diethanolamine) -2,2 - diphenyldistildisulfate.

The product is highly soluble in acetone, benzene, diethylene glycol and poorly in mineral oils.

The proposed compounds have good extreme pressure (in terms of four-ball friction machine) and anti-friction (in terms of MAST-1 device) properties presented in the table.