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Preparation of novel biphenyl tetradentate phosphite ligand and application of novel biphenyl tetradentate phosphite ligand in mixed/etherified C4 hydroformylation reaction

A technology of biphenyl tetradentate phosphonite and phosphonite, which is applied in the field of hydroformylation reaction 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 of novel biphenyl tetradentate phosphite ligand and application of novel biphenyl tetradentate phosphite ligand in mixed/etherified C4 hydroformylation reaction
  • Preparation of novel biphenyl tetradentate phosphite ligand and application of novel biphenyl tetradentate phosphite ligand in mixed/etherified C4 hydroformylation reaction
  • Preparation of novel biphenyl tetradentate phosphite ligand and application of novel biphenyl tetradentate phosphite ligand in mixed/etherified C4 hydroformylation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 4,6-di-tert-butyl-1,3-dihydroxybenzene (route 1 and 2):

[0028]

[0029] 1 (55g), tert-butanol (92.5g) and concentrated sulfuric acid (70g) were sequentially added into a 2L three-necked flask. After the addition was complete, the reaction bottle was replaced with a nitrogen atmosphere, and heated to reflux for 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 88 g of the target product with a yield of 80%. The NMR spectrum of compound 2 ( 1 H NMR) see attached figure 1 . 1 H NMR (400MHz, CDCl 3 ): δ=7.13 (s, 1H), 6.09 (s, 1H), 4.83 (s, 2H), 1.38 (s, 18H).

Embodiment 2

[0031] Preparation of 4,6-di-tert-butyl-1,3-dimethoxybenzene (route 1):

[0032]

[0033] In a 2L four-neck round bottom flask, 2 (31.5g), iodomethane (101g), potassium carbonate (98.2g) and 0.5L acetone were added in sequence. The resulting reaction system was raised to 30° C. for 4 hours. 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 30.5 g of the target product with a yield of 86%. The NMR spectrum of compound 3 ( 1 H NMR) see attached figure 2 . 1 H NMR (400MHz, CDCl 3 ): δ=7.17(s, 1H), 6.47(s, 1H), 3.83(s, 6H), 1.35(s, 18H).

Embodiment 3

[0035] Preparation of 2,2',6,6'-tetramethoxy-3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl (Route 1):

[0036]

[0037]Add 25.0 g of 4,6-di-tert-butyl-1,3-dimethoxybenzene into a dry 1L Schlenk bottle, replace the reaction bottle with a nitrogen atmosphere, and add 100 mL of tetrahydrofuran and TMEDA at -78°C (14g). A 2.5M n-butyllithium solution (44 mL) was added dropwise thereto, and then, 100 mL of a tetrahydrofuran solution of iron trichloride (39 g) was further added. The resulting mixture was reacted at -78°C for 8 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 oil. Column chromatography obtained 5.0 g of the target product with a yield of 21%. The NMR spectrum of compound 4 ( 1 H NMR) see attached image 3 . 1 H NMR (400MHz, CDCl ...

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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 general formula I, wherein a substituent R in the general formula I can be a cyclic phosphinestructure. Meanwhile, the invention discloses an application in a mixed / etherified C4 (butene) hydroformylation reaction system taking a novel biphenyl tetradentate phosphite ligand as a ligand.

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] - Preparation of 3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl and its hydroformylation reaction method in mixed carbon four. 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 widel...

Claims

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Application Information

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IPC IPC(8): C07F9/6571C07F9/145B01J31/18C07C45/50C07C47/02
CPCB01J2231/321B01J2531/822C07C37/11C07C41/16C07C41/30C07C37/055B01J31/1875B01J31/2433B01J31/2438C07C45/50C07C39/08C07C43/2055C07C43/205C07C39/15C07C47/02
Inventor 张润通彭江华
Owner 广东欧凯新材料有限公司
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