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Synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane

A synthetic method and technology of chloropropane, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high cost and difficult operation, and achieve the effect of simple operation, low cost, safe and reliable process

Inactive Publication Date: 2017-07-18
滨海博大化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the problems in the prior art that high temperature and high pressure reaction conditions are required, the operation is difficult and the cost is high, the invention provides a (s)-1-(4-diphenyl ether group)-2-hydroxyl-3-chloro The synthesis method of propane has the advantages of simple operation, high product purity and high yield, and is suitable for industrial production

Method used

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  • Synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane
  • Synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane
  • Synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane

Examples

Experimental program
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Effect test

Embodiment 1

[0036] (1) Put diphenyl ether (44.2g, 0.26mol) into a 250ml four-necked bottle, add (123.5g, (1.25mol) dichloroethane and stir for 1 hour, cool down to -5~0°C, quickly drop into (21g ,0.13mol) bromine, stirred for 1 hour, cooled to -5~0°C, began to drop 30% hydrogen peroxide (15g, (0.13mol), and finished dropping in 0.5~1 hour, the temperature was controlled at 0~5°C After the dropwise addition, the temperature was naturally raised to 25°C, kept at 27°C for 32 hours, quenched with 49g of 15% sodium bisulfite, after phase separation, washed with water until neutral, and distilled to recover dichloro Ethane was distilled under reduced pressure to recover foreboiling diphenyl ether, and finally 51.7 g of 4-bromodiphenyl ether was collected, with a yield of 80.0% and a content of 98.2%.

[0037](2) Under the protection of high-purity nitrogen, 3 g of 4-bromodiphenyl ether, 50 g of tetrahydrofuran, and 3.3 g of magnesium wire were put into a 500 ml four-necked bottle, and the tempe...

Embodiment 2

[0039] (1) Put diphenyl ether (44.2g, 0.26mol) into a 250ml four-necked bottle, add (109g, 1.1mol) dichloroethane and stir for 1 hour, cool down to -5 ~ 0°C, quickly drop into (25.6g, 0.16mol) of bromine, stirred for 1 hour, cooled to -5~0°C, started to add 30% hydrogen peroxide (15g, 0.13mol) dropwise, and finished dropping in 0.5 hour, controlled the temperature between 0~5°C, dropped After the addition, the temperature was naturally raised to 25°C, kept at 28°C for 30 hours, quenched with 49 g of 15% sodium bisulfite, after phase separation, washed with water until neutral, distilled to recover dichloroethane, and reduced Diphenyl ether was recovered by pressure distillation, and 47.8 g of 4-bromodiphenyl ether was finally collected, with a yield of 74.0% and a content of 98.5%.

[0040] (2) Under the protection of high-purity nitrogen, 3 g of 4-bromodiphenyl ether, 71 g of methyl tert-butyl ether, and 3.3 g of magnesium wire were dropped into a 500 ml four-necked bottle, a...

Embodiment 3

[0042] (1) Put diphenyl ether (44.2g, 0.26mol) into a 250ml four-necked bottle, add (136g, 1.37mol) dichloroethane and stir for 1 hour, cool down to -5 ~ 0°C, quickly drop into (17.3g, 0.11mol) of bromine, stirred for 1 hour, cooled to -5~0°C, started to add 30% hydrogen peroxide (15g, 0.13mol) dropwise, and finished dropping in 0.6 hours, controlled the temperature between 0~5°C, dropped After the addition, the temperature was naturally raised to 25°C, kept at 25°C for 48 hours, quenched with 49 g of 15% sodium bisulfite, after phase separation, washed with water until neutral, distilled to recover dichloroethane, and reduced Diphenyl ether was recovered by pressure distillation, and finally 49.3 g of 4-bromodiphenyl ether was collected, with a yield of 76.3% and a content of 98.0%.

[0043] (2) Under the protection of high-purity nitrogen, put 3 g of 4-bromodiphenyl ether, 61 g of ether, and 3.3 g of magnesium wire into a 500 ml four-necked bottle, heat up to 35 ° C and stir...

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Abstract

The invention provides a synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane. The synthesis method comprises the following steps of (1) generating 4-bromodiphenyl ether by using diphenyl ether and bromine under catalysis of hydrogen peroxide; (2) adding 4-bromodiphenyl ether, a solvent A and magnesium wires into a reaction vessel in an atmosphere of high-pure nitrogen, raising the temperature to 25-40 DEG C and stirring rapidly to induce Grignard reaction, dripping a solution of 4-bromodiphenyl ether-solvent A, and continuing reacting for 2 hours; and (3) reducing the temperature of a Grignard reagent to 0-5 DEG C, adding a composite coupling agent and a solution of S-epichlorohydrin-solvent A for reaction, pouring a reaction solution into dilute sulfuric acid, taking the upper layer and performing reduced pressure distillation so as to recycle the solvent A, adding residue into water, cooling and performing suction filtration, and drying a wet product to obtain a final product. The synthesis method is easy to operate, the product yield and purity are high, and no solid waste is generated in a production process, so that the synthesis method has higher economic feasibility and is applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of (s)-1-(4-diphenyl ether)-2-hydroxyl-3-chloropropane. Background technique [0002] There are many types of flame retardants, which are divided into additive flame retardants and reactive flame retardants according to the method of use. Additive flame retardants are added to polymers by mechanical mixing to make polymers flame retardant. At present, additive flame retardants mainly include organic flame retardants and inorganic flame retardants, and reactive flame retardants are As a monomer to participate in the polymerization reaction, so that the polymer itself contains flame retardant components, the advantage is that it has little impact on the performance of the polymer material, and the flame retardancy is durable. (s)-1-(4-diphenyl ether)-2-hydroxy-3-chloropropane can be used as a novel flame retardant for improving the combusti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C43/295
CPCC07C41/22C07C41/30C07C43/29C07C43/295
Inventor 巫辅才
Owner 滨海博大化工有限公司
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