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Bis-phosphorous acid triphenyl (3,3',5,5'-tetra-tert-butyl-2,2'-xenol) ester microwave synthesis method

A technology of trialkyl phosphite and bisphosphite, which is applied in the field of microwave synthesis of bisphosphite triester, to achieve the effects of high product yield, simple post-processing and short reaction time

Active Publication Date: 2013-12-25
CNOOC TIANJIN CHEM RES & DESIGN INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of this invention is to provide a kind of microwave synthesis method of bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol) ester, in order to solve the problem of using in the prior art A series of problems caused by phosphorus trichloride as raw material

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  • Bis-phosphorous acid triphenyl (3,3',5,5'-tetra-tert-butyl-2,2'-xenol) ester microwave synthesis method

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Embodiment 1

[0020] 16.6 grams of triethyl phosphite, 41.1 grams of 3,3',5,5'-tetra-tert-butyl-2,2'-biphenol and 2.9 grams of diphenylphosphorous chloride catalyst were placed in a microwave reaction device , after mixing and stirring evenly, react under microwave radiation with a power of 200w for 25 minutes. After the reaction is completed, the crude product of the reaction is recrystallized with a mixed solvent of toluene and n-hexane to obtain white crystals. Chromatographic analysis verification, the product is bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol) ester, yield 88% (yield is based on 3,3',5 ,5'-tetra-tert-butyl-2,2'-biphenol as the basis for calculation).

Embodiment 2

[0022] Put 49.8 grams of triethyl phosphite, 41.1 grams of 3,3',5,5'-tetra-tert-butyl-2,2'-biphenol and 0.9 grams of phenyl phosphorus dichloride catalyst in a microwave reaction device , after mixing and stirring evenly, react under microwave radiation with a power of 200w for 15 minutes. After the reaction is completed, the crude product of the reaction is recrystallized with acetonitrile to obtain white crystals, which are analyzed and reported in the literature by hydrogen nuclear magnetic resonance spectrum, phosphorus spectrum and high performance liquid chromatography. Consistent, the product is bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol) ester, yield 91% (yield is 3,3',5,5 '-tetra-tert-butyl-2,2'-biphenol as the basis for calculation).

Embodiment 3

[0024] 24.8 grams of trimethyl phosphite, 41.1 grams of 3,3',5,5'-tetra-tert-butyl-2,2'-biphenol and 6.6 grams of diphenylphosphorous chloride catalyst were placed in a microwave reaction device , after mixing and stirring evenly, react under microwave radiation with a power of 500w for 10 minutes. After the reaction is completed, the reaction crude product is recrystallized with a mixed solvent of ethyl acetate and petroleum ether to obtain white crystals. The liquid chromatographic analysis is consistent with the literature report, and the product is bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol) ester, and the yield is 93% (the yield is based on 3 ,3',5,5'-tetra-tert-butyl-2,2'-biphenol as the basis for calculation).

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Abstract

The invention discloses a bis-phosphorous acid triphenyl (3,3',5,5'-tetra-tert-butyl-2,2'-xenol) ester microwave synthesis method. According to the method, phosphorous acid trialkyl ester and 3,3',5,5'-tetra-tert-butyl-2,2'-xenol are used as raw materials, wherein the molar ratio of the phosphorous acid trialkyl ester and the 3,3',5,5'-tetra-tert-butyl-2,2'-xenol is 1:1-10:1; aryl substitute phosphoric chloride or alkyl substitute phosphoric chloride servers as a catalyst; bis-phosphorous acid triphenyl (3,3',5,5'-tetra-tert-butyl-2,2'-xenol) ester is formed by synthesis under microwave radiation without solvent; microwave radiation power is 100-1000w, and microwave reaction time is 5-30min. The method has the advantages of being high in bis-phosphite acid ester yield, small in number of by-products, short in reaction time, capable of achieving solvent-free operation, environmentally friendly, free of pollution, simple in aftertreatment and the like.

Description

Technical field: [0001] The invention relates to a microwave synthesis method of bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol). Background technique: [0002] Bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol) ligand contains two coordinated phosphorus atoms in its molecular structure, which can be coordinated with transition metal catalysts to form A double chelate-coordinated metal complex, the ligand plays an important role in transition metal-catalyzed reactions. [0003] The synthesis method disclosed in the prior art is mainly divided into two steps: (1) the reaction of phosphorus trichloride and 3,3',5,5'-tetra-tert-butyl-2,2'-biphenol to generate 3,3', 5,5'-tetra-tert-butyl-2,2'-bisphenoxyphosphine chlorine intermediate; (2) This intermediate is then combined with 3,3',5,5'-tetra-tert-butyl-2,2 '-Biphenol reacts under the action of acid-binding agent to generate bisphosphite tris(3,3',5,5'-tetra-tert-butyl-2,2'-biphenol). [0004] In the exi...

Claims

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Application Information

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IPC IPC(8): C07F9/6574
Inventor 李晨于海斌蒋凌云李继霞李俊郝婷婷
Owner CNOOC TIANJIN CHEM RES & DESIGN INST