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Phosphoramidite ligand, catalyst and method for preparing 4-acetoxyl butaldehyde

A phosphoramidite and catalyst technology, which is applied in the field of preparation of 4-acetoxybutyraldehyde, can solve the problems of weak coordination, easy hydrolysis, and influence on catalyst separation and application, and achieve high reaction conversion rate and high selectivity Effect

Active Publication Date: 2018-04-17
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this phosphite ligand has the disadvantages of instability and easy hydrolysis, and its coordination with rhodium is not strong, so the formed catalyst is easily deactivated at high temperature, which affects the separation and application of the catalyst.

Method used

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  • Phosphoramidite ligand, catalyst and method for preparing 4-acetoxyl butaldehyde
  • Phosphoramidite ligand, catalyst and method for preparing 4-acetoxyl butaldehyde
  • Phosphoramidite ligand, catalyst and method for preparing 4-acetoxyl butaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] To prepare the phosphoramidite ligand L1, proceed as follows:

[0057] 1. Dissolve 9,9-dimethylxanthene (21.0g, 0.1mol) in 200mL of n-hexane. After it is completely dissolved, cool the system to -78°C in a dry ice acetone bath; Add n-BuLi (n-butyllithium) hexane solution (2M, 100mL) dropwise, remove the dry ice acetone bath, and naturally warm up to room temperature for 6 hours to obtain a lithium salt solution. After testing, the lithium salt has the formula the structural formula of (II);

[0058] 2. Dissolve phosphorus trichloride (27.5g, 0.2mol) and triethylamine (40.5g, 0.4mol) in 200mL of n-hexane, and place the solution in an ice-water bath to cool to 0-5°C; N, N-dimethylethylenediamine (17.6g, 0.2mol) n-hexane solution was slowly added dropwise to the mixture; after the dropwise addition, the ice-water bath was removed, the temperature was naturally raised to room temperature, and the reaction was continued for 4 hours; the reaction was completed, filtered, and...

Embodiment 2-6

[0064] Compared with Example 1, Examples 2-6 only use ethylenediamine with different substituents as raw materials, and synthesize phosphoramidite ligands in the same way as Example 1, which are respectively numbered L2-L6.

[0065] The substituent ethylenediamine structural formula used in embodiment 2-6 is shown in formula (IV), wherein, the R groups in the compound of formula (IV) used in embodiment 2-6 are respectively isopropyl , Cyclohexyl, phenyl, p-methylphenyl, p-tert-butylphenyl.

[0066] The obtained product L2-L6 of embodiment 2-6 all has structural formula (I), wherein the R group in L2 is isopropyl group, and the R group in L3 is cyclohexyl group, and the R group in L4 is All are phenyl groups, the R groups in L5 are all p-methylphenyl groups, and the R groups in L6 are all p-tert-butylphenyl groups.

[0067] The phosphoramidite ligands L1-L6 prepared in Examples 1-6 were qualitatively analyzed by NMR, 1 H NMR (300MHz, CDCl 3 ) data looks like this:

[0068] ...

Embodiment 7

[0075] This embodiment is an embodiment of allyl acetate hydroformylation to synthesize 4-acetoxybutyraldehyde, and its preparation steps are as follows:

[0076] 10 mg of rhodium acetylacetonate was dissolved in 100 g of allyl acetate, 343.7 mg of ligand L1 was dissolved in 100 g of allyl acetate, the two solutions were added to a 1 L reaction kettle, and then 200 g of allyl acetate was added. Nitrogen replacement, synthesis gas replacement, filling with synthesis gas, boosting the pressure to 1MPa. Start the stirring, and raise the temperature to 100° C. to carry out the hydroformylation reaction. After the reaction was completed, the temperature was lowered to room temperature, and the pressure was released. The target product 4-acetoxybutyraldehyde was separated from the reaction liquid by rectification under reduced pressure, and the tower bottom liquid was reused as a catalyst solution. The raw material conversion rate is above 99%, and the yield of 4-acetoxybutyraldehy...

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Abstract

The invention provides a phosphoramidite ligand, a catalyst and a method for preparing 4-acetoxyl butaldehyde. The phosphoramidite ligand has the following structural formula (I) as shown in the specification. In the formula, the various groups R in the formula (I) are the same or different; and the various groups R are respectively independently selected from C1-C6 alkyl fragments or C6-C10 aryl-containing fragments. The catalyst containing the phosphoramidite ligand provided by the invention has the characteristics of being high in catalytic activity, easy to recycle and the like. Moreover,the 4-acetoxyl butaldehyde is prepared by adopting the catalyst disclosed by the invention and has high conversion ratio and yield.

Description

technical field [0001] The invention relates to the technical field of preparation of 4-acetoxybutyraldehyde, in particular to a phosphoramidite ligand and a catalyst containing the ligand, and the use of the catalyst to catalyze the hydroformylation of allyl acetate to generate 4-acetyl Oxybutyraldehyde method. Background technique [0002] 1,4-Butanediol (BDO for short) is an important organic and fine chemical raw material, which is widely used in the fields of medicine, chemical industry, textile, papermaking, automobile and daily chemical industry. BDO can produce polybutylene terephthalate (PBT), γ-butyrolactone (GBL) and polyurethane resin (PU Resin), coatings and plasticizers, etc., as well as solvents and brighteners in the electroplating industry Wait. [0003] The current process for industrialized production of BDO is that allyl alcohol undergoes a liquid-phase hydroformylation reaction under the action of a rhodium-triphenylphosphine system catalyst to generat...

Claims

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Application Information

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IPC IPC(8): C07F9/6584B01J31/24C07C67/293C07C69/14
CPCB01J31/187B01J2231/321B01J2531/822C07C67/293C07F9/65848C07C69/14
Inventor 吕英东朱龙龙刘俊贤宋明焱薛勇勇李金明张涛黎源
Owner WANHUA CHEM GRP CO LTD
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