Preparation method of benzotriazole diethyl phosphate

A technology of benzotriazole diethyl phosphate and benzotriazole, which is applied in the field of preparation of benzotriazole diethyl phosphate, can solve the problems of reaction pollution, use of toxic raw materials, etc., and achieves easy separation, The effect of mild conditions and high product yield

Pending Publication Date: 2021-12-21
NORTH CHINA UNIV OF WATER RESOURCES & ELECTRIC POWER
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Problems solved by technology

[0009] The method for synthesizing diethyl benzotriazole phosphate in the prior art has the problems of using toxic raw materials and causing pollution in the reaction

Method used

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  • Preparation method of benzotriazole diethyl phosphate
  • Preparation method of benzotriazole diethyl phosphate
  • Preparation method of benzotriazole diethyl phosphate

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[0025] The invention provides a kind of preparation method of benzotriazole diethyl phosphate, comprising the following steps:

[0026] Diethyl phosphite, benzotriazole, oxidant and iodine catalyst are mixed for oxidative coupling reaction to obtain the benzotriazole diethyl phosphate; the oxidant is hydrogen peroxide or tert-butyl hydrogen peroxide alcohol, the iodine catalyst is I 2 or compounds containing iodide ions.

[0027] In the present invention, unless otherwise specified, the raw materials used are all commercially available products in this field.

[0028] In the present invention, the compound containing iodide ion is preferably sodium iodide, potassium iodide or tetrabutylammonium iodide.

[0029] In the present invention, the equivalent ratio of the iodine catalyst to benzotriazole is preferably 0.1˜0.2:1.

[0030] In the present invention, the equivalent ratio of diethyl phosphite to benzotriazole is preferably 1˜2:1.

[0031] In the present invention, the ...

Embodiment 1

[0049] A 100mL round bottom flask was fixed on a magnetic stirrer with a stand, and a rotor was added to the flask. Weigh 1.19g (10.0mmol) of benzotriazole with a balance, add 40mL of dichloromethane and 1.41mL (11.0mmol) of diethyl phosphite, add a catalytic amount of iodine 253mg (1.0mmol), add 1.24mL at room temperature 30% hydrogen peroxide (11.0 mmol). The rotating speed of the magnetic stirrer was 500 rpm, and the reaction was carried out at room temperature for 24 hours.

[0050] After the reaction is complete, transfer the reaction mixture solution to a separatory funnel, let it stand to separate layers, and keep the lower organic phase. Wash twice with saturated sodium bicarbonate solution and once with saturated sodium chloride solution. Pour the above-mentioned washed organic solution into an Erlenmeyer flask, and dry it with anhydrous sodium sulfate to remove the moisture in the solution. Vacuum suction filtration, the organic solution was placed on a rotary eva...

Embodiment 2

[0052] A 100mL round bottom flask was fixed on a magnetic stirrer with a stand, and a rotor was added to the flask. Weigh 1.19g (10.0mmol) of benzotriazole with a balance, add 40mL of dichloromethane and 1.41mL (11.0mmol) of diethyl phosphite, add catalytic amount of tetrabutylammonium iodide 369mg (1.0mmol), 1.24 mL of 30% hydrogen peroxide (11.0 mmol) was added at room temperature. The rotating speed of the magnetic stirrer was 500 rpm, and the reaction was carried out at room temperature for 24 hours.

[0053]After the reaction is complete, transfer the reaction mixture solution to a separatory funnel, let it stand to separate layers, and keep the lower organic phase. Wash twice with saturated sodium bicarbonate solution and once with saturated sodium chloride solution. Pour the above-mentioned washed organic solution into an Erlenmeyer flask, and dry it with anhydrous sodium sulfate to remove the moisture in the solution. Vacuum filtration, the organic solution was plac...

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Abstract

The invention provides a preparation method of benzotriazole diethyl phosphate, which belongs to the field of organic synthesis. The method comprises the following steps of mixing diethyl phosphite, benzotriazole, an oxidant and an iodine catalyst, and carrying out oxidative coupling reaction to obtain benzotriazole diethyl phosphate. The oxidant is hydrogen peroxide or tert-butyl hydroperoxide, and the iodine catalyst is I2 or a compound containing iodide ions. According to the method, the benzotriazole diethyl phosphate is prepared through one-step reaction by using green oxidants such as hydrogen peroxide and hydrogen peroxide tert-butyl alcohol under the condition of an iodine catalyst, carbon tetrachloride with high toxicity or phosphoryl chloride with high corrosivity is not used, the reaction conditions are more green, toxic wastes are not generated, the reaction steps are simple, the conditions are mild, and the product is easy to separate and high in yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of benzotriazole diethyl phosphate. Background technique [0002] Antiwear agent is a high-tech lubricating oil additive, usually used in lubricating oil are sulfur antiwear agent, phosphorus antiwear agent, sulfur phosphorus antiwear agent, halogen antiwear agent, organic Metal antiwear agents and boron antiwear agents can reduce engine wear and increase engine power, so they are also called engine maintenance agents or powerful repair agents. [0003] Diethyl benzotriazole phosphate, English name Phosphonic acid, P-1H-benzotriazol-1-yl-, diethyl ester, CAS number 199532-56-4, molecular formula C 10 h 14 N 3 o 3 P, molecular weight 255.21, colorless oily liquid, is a phosphorus nitrogen type antiwear agent, contains phosphoramide and phosphoester groups in its structure, and is a neutral antiwear agent. [0004] The method for synthesizing ben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6518
CPCC07F9/65188
Inventor 刘辉韩龙飞郭俊杰刘秉涛潘璐
Owner NORTH CHINA UNIV OF WATER RESOURCES & ELECTRIC POWER
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