Preparation method of biphenyl tetradentate phosphite ligand

A technology of biphenyl tetradentate phosphite and biphenyl tetradentate phosphite, which is applied in the field of preparation of biphenyl tetradentate phosphonite ligands and can solve the problem of high production cost of 1-butene

Pending Publication Date: 2020-11-10
广东欧凯新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional PPh-based 3 The current technology can only realize the hydroformylation reaction of 1-butene, the production cost of 1-butene is high, and the cheaper raw material is mixed butene or ether-butene

Method used

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  • Preparation method of biphenyl tetradentate phosphite ligand
  • Preparation method of biphenyl tetradentate phosphite ligand
  • Preparation method of biphenyl tetradentate phosphite ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 2,2’,6,6’-tetramethoxy-1,1’-biphenyl:

[0020]

[0021] Add 1 (13.8g), THF (200mL), tetramethylethylenediamine (16 g) in sequence to a 1L three-neck flask, and add n-butyllithium (40mL 2.5mol / L ), then add ferric chloride (16.1g), after addition completes, reaction bottle is heated to room temperature reaction 24 hours. The solvent was spin-dried under reduced pressure, 400 mL of water was added, and extracted three times with ethyl acetate (500 mL each time). The obtained organic phase was dried over anhydrous sodium sulfate and then spin-dried under reduced pressure, and the residue was subjected to flash column chromatography to obtain 22 g of the target product with a yield of 80%.

Embodiment 2

[0023] Preparation of 2,2’,6,6’-tetrahydroxy-1,1’-biphenyl:

[0024]

[0025] In a 1L four-neck round-bottom flask, add 2 (27g) and 500mL of dichloromethane in sequence, drop boron tribromide (101g) at -30°C, and raise the resulting reaction system to 30°C to react 4 Hour. After the resulting reaction mixture was concentrated, 400 mL of water was added and extracted three times with ethyl acetate (600 mL each time). The residue was subjected to column chromatography to obtain 20.5 g of the target product with a yield of 91%.

Embodiment 3

[0027] Preparation of 2,2',6,6'-tetramethoxy-3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl:

[0028]

[0029] Add 3 (22.0 g) to a dry 1 L Schlenk bottle, replace the reaction bottle with a nitrogen atmosphere, and add 200 mL of tetrahydrofuran, organic or inorganic acid (1.0 g) at 25°C. Isobutene at a pressure of 1.5 atmospheres was continuously fed, and the reaction was continued for 12 hours. After the reaction solution was quenched with water, 300 mL of water was added and extracted three times with ethyl acetate (400 mL each time). The obtained organic phase was dried over anhydrous sodium sulfate, and then spin-dried under reduced pressure to obtain a light yellow solid. Column chromatography obtained 40.0 g of the target product with a yield of 90%. 1 H NMR (600MHz, (CD 3 ) 2 SO): δ=7.53(s,4H), 7.17(s,2H), 1.37(s,36H).

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PUM

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Abstract

The invention discloses a preparation method of a novel biphenyl tetradentate phosphite ligand 2,2',6,6'-tetra [(1,1'-biphenyl-2,2'-diyl) phosphite]-3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl and derivatives thereof. The novel biphenyl tetradentate phosphite ligand has a structure as shown in a general formula I, wherein a substituent R in the general formula I can be a cyclic phosphine structure. The novel biphenyl tetradentate phosphite ligand has good conversion rate and normal-to-isomeric ratio in a mixed/etherified C4 (butylene) hydroformylation reaction system.

Description

technical field [0001] The invention relates to a novel biphenyl tetradentate phosphonite ligand 2,2',6,6'-tetrakis[(1,1'-biphenyl-2,2'-diyl)phosphonite] - a preparation method of 3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl and derivatives thereof. Background technique [0002] Since the hydroformylation reaction was discovered by Professor Otto Roelen in 1938 (Chem Abstr, 1994, 38-550), it has been widely used in industry. Since aldehydes can be easily converted into corresponding alcohols, carboxylic acids, esters, imines, etc., which have important uses in organic synthesis, aldehydes synthesized by hydroformylation are widely used in industrial production. Scale synthesis. The annual industrial production of aldehydes produced by hydroformylation has reached 10 million tons (Adv. Synth. Catal. 2009, 351, 537-540). [0003] In the hydroformylation reaction, although bidentate phosphine ligands and tetradentate phosphine ligands have been widely reported and patented by la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574B01J31/22C07C47/02C07C45/50
CPCC07F9/65744B01J31/185C07C45/505B01J2531/827B01J2231/321C07C2531/18C07C47/02
Inventor 张润通彭江华王建新闫鑫
Owner 广东欧凯新材料有限公司
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