A kind of synthetic method of 2,2'-bisdiphenylphosphino-1,1'-binaphthalene

A technology of diphenylphosphino group and synthesis method, which is applied in the field of synthesis of 2,2'-bis-diphenylphosphino-1,1'-binaphthyl, can solve the problems of high production cost, great difficulty in operation and the like , to achieve the effect of low price, strong industrial application prospects, and easy availability

Active Publication Date: 2020-03-24
XINXIANG RUNYU NEW MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method uses nickel and noble metal palladium as a mixed catalyst to complete the final catalytic coupling reaction, which makes the production cost of the new coupling method still high
At the same time, the catalytic coupling method requires an inert atmosphere (such as nitrogen, argon) to protect the reaction system, so that the catalytic coupling synthesis process (Merck method, Monsanto method and Chinese patent CN104370963) still has great operational difficulty

Method used

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  • A kind of synthetic method of 2,2'-bisdiphenylphosphino-1,1'-binaphthalene
  • A kind of synthetic method of 2,2'-bisdiphenylphosphino-1,1'-binaphthalene
  • A kind of synthetic method of 2,2'-bisdiphenylphosphino-1,1'-binaphthalene

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Synthesis of 2,2'-bisethoxy-1,1'-binaphthalene

[0032] In a 50L glass reactor equipped with a reflux condenser and mechanical stirring, add 5.7Kg binaphthyldiol, 4.7Kg iodoethane, 8.3Kg potassium carbonate and 30L acetonitrile, heat to 80°C under stirring, and react for 12 hours. After the reaction solution returns to room temperature, remove potassium carbonate by filtration, concentrate acetonitrile to obtain the crude product 2,2'-bisethoxy-1,1'-binaphthalene, wash with water, and then dry in vacuum to obtain a white solid 2,2'- Diethoxy-1,1'-binaphthalene 6.3Kg, yield 92%. The acetonitrile solvent concentrated by distillation is retained and can be used in the next batch.

[0033] (2) Synthesis of 2,2'-bisdiphenylphosphino-1,1'-binaphthyl

[0034] In a 50L glass reactor equipped with a reflux condenser and mechanical stirring, add 3.4Kg of 2,2'-bisethoxy-1,1'-binaphthalene prepared in the above step (1), and 350g of lithium metal flakes, 5.8kg of tetramethyl...

Embodiment 2

[0036] In a 50L glass reactor equipped with a reflux condenser and mechanical stirring, add 3.4Kg of 2,2'-bisethoxy-1,1'-binaphthalene prepared in step (1) of Example 1, and 350g of lithium metal Tablets, 5.8kg tetramethylethylenediamine and 30L dibutyl ether, heated to 140°C under stirring, reacted for 6 hours, lowered to 0°C, added dropwise 8.8Kg diphenylphosphine chloride, and then added 900g water to quench reaction. Concentrate the product solution, filter and wash with methanol, then vacuum-dry to obtain off-white solid 5.8Kg, the product is passed through 1 H-NMR, 13 C-NMR and 31 P-NMR confirmed the structure as 2,2'-bisdiphenylphosphino-1,1'-binaphthyl, the yield was 93%, and the purity of the product analyzed by liquid chromatography was 99.6%.

Embodiment 3

[0038]In a 50L glass reactor equipped with a reflux condenser and mechanical stirring, add 3.4Kg of 2,2'-bisethoxy-1,1'-binaphthalene prepared in step (1) of Example 1, and 350g of lithium metal Tablets, 5.8kg tetramethylethylenediamine and 30L dioxane, heated to 100°C under stirring, after 8 hours of reaction, lowered to 0°C, added dropwise 8.8Kg diphenylphosphine chloride, and then added 900g water to quench extinction reaction. Concentrate the product solution, filter and wash with methanol, then vacuum-dry to obtain off-white solid 5.9Kg, the product is passed through 1 H-NMR, 13 C-NMR and 31 P-NMR confirmed the structure as 2,2'-bisdiphenylphosphino-1,1'-binaphthyl, the yield was 95%, and the purity of the product analyzed by liquid chromatography was 99.6%.

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Abstract

The invention discloses a synthetic method of 2,2'-double diphenyl phosphine-1,1'-dinaphthalene. The method comprises the following steps: adding a lithium metal sheet, a ligand, 2,2'-diethoxy-1,1'-dinaphthalene and an ethers solvent are added in a reaction still, heating the materials to the temperature of 60-140 DEG C, reacting the materials for 6-12 hours, dropping chlorodiphenylphosphine at the temperature of 0 DEG C, heating the material to room temperature, and obtaining the product after the reaction is completed; equivalent water quenching is carried out, a product solution is concentrated and filtered, a filter cake is washed with methanol, and vacuum drying is carried out to obtain the product 2,2'-double diphenyl phosphine-1,1'-dinaphthalene (BINAP). The method has the advantages of high yield, low preparation cost, simple post-treatment, high product purity, and is suitable for process enlargement.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic phosphine compounds, and in particular relates to a synthesis method of 2,2'-bisdiphenylphosphino-1,1'-binaphthalene. Background technique [0002] With the development of new drugs and new material industries, efficient, green and atom-economical synthesis processes are becoming more and more important. In recent years, new catalytic systems have developed rapidly in scientific research and industrial applications. Catalysts in chemical reactions can effectively speed up the reaction rate, improve the yield and selectivity of the reaction, so as to achieve the long-term goal of green chemistry. It is worth noting that the organophosphine ligands that regulate the catalytic reaction play a crucial role in the novel catalytic system. Therefore, organic phosphine ligands have become a class of widely used new chemical products, as well as fine chemicals with high added value. The mark...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50C07F1/02
CPCC07F1/02C07F9/5022
Inventor 李恒
Owner XINXIANG RUNYU NEW MATERIAL TECH CO LTD
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