Method used for preparing unsaturated aromatic ester from phenylacetylene via carbonylation

A phenylacetylene and unsaturated technology, which is applied in the field of polymer-supported palladium-based catalysts, can solve problems that affect industrial applications, that homogeneous catalysts are difficult to recycle, and increase production costs.

Active Publication Date: 2017-06-16
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the homogeneous catalyst is difficult to separate from the product for recycling, which affects the industrial application of the process
In addition, the reaction requires the use of highly corrosive protonic acid, and the reaction device is seriously corroded, which greatly increases the production cost

Method used

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  • Method used for preparing unsaturated aromatic ester from phenylacetylene via carbonylation
  • Method used for preparing unsaturated aromatic ester from phenylacetylene via carbonylation
  • Method used for preparing unsaturated aromatic ester from phenylacetylene via carbonylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] POL-2V-P,N-SO 3 H Preparation method: In a liquid nitrogen bath and a nitrogen atmosphere, add 45ml of tetrahydrofuran, 0.12mol of n-butyllithium, 0.1mol of o-bromopyridine, and 0.135mol to a 1L three-necked round-bottomed flask with a magnetic stirrer ZnCl 2 , 45ml pyridine, 90ml tetrahydrofuran, and react at room temperature for 14h. Pour out the liquid in the bottle under nitrogen protection, then add 60ml pyridine, 180ml tetrahydrofuran, and 0.12mol of PCl3 solution (dissolved in 60ml pyridine, 60ml tetrahydrofuran) under liquid nitrogen bath conditions, then react at room temperature for 26h (named reaction Liquid 1). In a liquid nitrogen bath and a nitrogen atmosphere, add 0.22mol (5.4g) of magnesium chips, 35ml of tetrahydrofuran, and 36.6g (0.2mol) of p-bromostyrene to another 1L three-necked round-bottomed flask with a magnetic stirrer (named as reaction solution 2). After the reaction solution 1 was filtered, it was added to the reaction solution 2 in a li...

Embodiment 2

[0022] Reaction temperature is 40 ℃, and other conditions are with embodiment 1.

Embodiment 3

[0024] Reaction temperature is 50 ℃, and other conditions are with embodiment 1.

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Abstract

The invention provides a method used for preparing an unsaturated aromatic ester from phenylacetylene via carbonylation. According to the method, phenylacetylene, methanol, and carbon monoxide are taken as reaction raw materials, reaction temperature is controlled to be 30 to 90 DEG C, initial pressure is controlled to be 2 to 6MPa, a multifunctional polymer supported palladium-based catalyst is adopted, and carbonylation of phenylacetylene is catalyzed so as to synthesize the unsaturated aromatic ester. The solid multifunctional polymer (POL-2V-P, N-SO3H) is obtained via hinge polymerization of vinyl2-pyridine diphenylphosphine with vinylbenzene sulfonate under certain conditions, and the solid multifunctional polymer is used for complexing and immobilizing palladium acetate so as to prepare the multifunctional polymer supported palladium-based catalyst. Synthesis of the unsaturated aromatic ester from phenylacetylene via carbonylation is realized via one-step method, activity and selectivity are both high, corrosion on equipment is low, and separation and recycling are convenient to realize.

Description

technical field [0001] The invention relates to a method for synthesizing unsaturated aromatic esters by carbonylation of phenylacetylene, in particular to a method using phenylacetylene, carbon monoxide and methanol as reaction raw materials, at a reaction temperature of 30-90°C, and an initial pressure of carbon monoxide of 2-6 MPa Under the conditions, the palladium-based catalyst supported by the multifunctional polymer is used to catalyze the carbonylation of phenylacetylene to prepare the unsaturated aromatic ester. Background technique [0002] Unsaturated aromatic ester (methyl cinnamate and its isomers) is a white crystal with cinnamon paste and sweet fruit aroma. It is mainly used in food, daily chemical and pharmaceutical industries and as raw materials for organic synthesis. Broad development prospects. At present, the synthesis of methyl cinnamate is based on cinnamic acid and methanol as raw materials, and is directly synthesized by esterification under the ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/618C07C67/38B01J31/24
CPCB01J31/2409B01J2231/321B01J2531/824C07C67/38C07C69/618Y02P20/50
Inventor 丁云杰陈兴坤朱何俊
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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