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Preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and intermediate of DOPO

An o-phenylphenol and compound technology, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, and organic chemistry, etc. problems, to achieve the effect of simplifying production operations

Active Publication Date: 2018-01-09
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First of all, in the process of preparing CDOP, if the excessive amount of phosphorus trichloride is too much, it is easy to cause side reactions, which not only causes difficulties in the purification of intermediate products, but also affects the reaction yield and the purity of the final product; for this reason, the existing preparation The method usually adopts the mode of adding phosphorus trichloride in batches during the reaction process, and most of them are added dropwise, and the operation is too complicated (refer to: CN102219806A)
Secondly, after the Friedel-Crafts reaction is completed, phosphorus trichloride and other by-products that do not participate in the reaction need to be removed by distillation before entering the next step of the hydrolysis process, otherwise side reactions will also occur, which further increases the preparation process. the complexity of

Method used

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  • Preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and intermediate of DOPO
  • Preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and intermediate of DOPO
  • Preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and intermediate of DOPO

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Example 1 Preparation of DOPO by the method of the present invention

[0047] 1. Add 100g o-phenylphenol (1eq, 0.588mol), 1g anhydrous zinc chloride (0.0125eq, 0.0073mol) and 80.7g phosphorus trichloride (1eq, 0.588mol) into a 500mL four-necked flask, and heat up to After reacting at 100° C. for 2 hours, continue to raise the temperature to 160° C. for 2 hours. The reaction was complete as detected by HPLC, and the reaction solution was directly used for the next reaction.

[0048] 2. Add 150 g of toluene and 5 g of diatomaceous earth to the reaction liquid in the previous step, stir at room temperature for 0.5 h, and filter to obtain a colorless clear liquid. 50 g of purified water was added to the filtrate, the temperature was raised to reflux for 4 h, and the reaction was detected by TLC to be complete. Cool down to 0°C, stir vigorously to precipitate a white solid, filter, wash the filter cake twice with 50 g of purified water, the filter cake is detected as a HPPA...

Embodiment 2

[0051] Example 2 Preparation of DOPO by the method of the present invention

[0052] 1. Add 100g of o-phenylphenol (1eq, 0.588mol), 1g of anhydrous zinc chloride (0.0125eq, 0.0073mol) and 112.98g of phosphorus trichloride (1.4eq) into a 500mL four-necked flask, and heat up to 80°C After reacting for 2 hours, continue to heat up to 180° C. for 2 hours, and the reaction is complete as detected by HPLC, and the reaction solution is directly used for the next reaction.

[0053]2. Add 150 g of toluene and 5 g of diatomaceous earth to the reaction liquid in the previous step, stir at room temperature for 0.5 h, and filter to obtain a colorless clear liquid. 50 g of purified water was added to the filtrate, the temperature was raised to reflux for 4 h, and the reaction was detected by TLC to be complete. Cool down to 0°C, stir vigorously to precipitate a white solid, filter, wash the filter cake twice with 50 g of purified water, collect the filter cake, and directly use it for the ...

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Abstract

The invention relates to a preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and an intermediate of DOPO and belongs to the field of chemistry. Aiming at solving the technical problems, the invention provides the preparation method of the DOPO intermediate CDOP; the method comprises the following steps: raising the temperature of a mixture of o-phenylphenol, zinc chloride and phosphorus trichloride to 60 DEG C to 140 DEG C and carrying out esterification reaction; continually raising the temperature to 160 DEG C to 220 DEG C and reacting to obtain the product. Byadopting the preparation method provided by the invention, the phosphorus trichloride can be added in one step in a material feeding process and the excessive phosphorus trichloride and reaction byproducts do not need to be removed by decompressing and distilling after the reaction is finished, so that the production operation is greatly simplified; compared with an existing technology, the preparation method has remarkable advantages.

Description

technical field [0001] The invention relates to a preparation method of DOPO and its intermediate, belonging to the field of chemistry. Background technique [0002] 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, referred to as DOPO, molecular formula C 12 h 9 PO 2 , CAS No.: 35948-25-5, molecular weight 216.2, melting point 117-121°C, white flaky or powdery solid. The flame retardant synthesized by DOPO and its derivatives has the characteristics of high efficiency, no halogen, less smoke, low toxicity, no migration, and long-lasting flame retardant performance. It is a new type of halogen-free and environmentally friendly flame retardant developed in recent years. At present, its synthesis and application have attracted extensive attention. [0003] The synthetic route of DOPO is as follows: [0004] [0005] Mainly comprise the following steps: 1, ortho-phenylphenol OPP and phosphorus trichloride under the effect of catalyst (such as zinc chloride) one-pot es...

Claims

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Application Information

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IPC IPC(8): C07F9/6571C07F9/6574
Inventor 姚中伟王福雄程柯
Owner LIER CHEM CO LTD
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