Method for preparing pelargonic acid and isononanoic acid by catalyzing 1-octylene through water-soluble palladium-phosphine complex catalyst

A catalyst and water-soluble technology, applied in the direction of chemical instruments and methods, carbon monoxide reaction to prepare carboxylic acid, organic compound/hydride/coordination complex catalyst, etc., can solve the problem of polluting products, high catalytic cost, and catalysts that cannot be recycled, etc. problems, to achieve the effect of easy separation, saving production cost and good recycling effect

Inactive Publication Date: 2011-05-04
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are also relevant reports on the carbonylation reaction of olefins, but they all use triphenylphosphine (TPP) as a ligand, and palladium acetate is a catalyst for the reaction. Since the catalyst and the product cannot be effectively separated, this method not only pollutes the product Moreover, the catalyst cannot be recycled, so its catalytic cost is higher

Method used

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  • Method for preparing pelargonic acid and isononanoic acid by catalyzing 1-octylene through water-soluble palladium-phosphine complex catalyst

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Experimental program
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Effect test

Embodiment 1

[0016] a. Add 60 mL of deoxygenated water (pH=7), 0.1 g of palladium acetate and 1 g of m-trisulfonate triphenylphosphine ligand to the autoclave in sequence, and stir at room temperature for 1 h after vacuuming;

[0017] b. Add 2 g of phase transfer agent cetyltrimethylammonium bromide, 2 g of p-toluenesulfonic acid and 10 g of substrate 1-octene with a purity of 50%, and seal the autoclave;

[0018] c. Replace the air in the kettle with high-purity CO gas once to reach a reaction temperature of 80°C, and press in CO gas with a pressure of 0.5MPa at one time to carry out a full carbonylation reaction for 2 hours;

[0019] d. After the reaction is over, fully cool with an ice bath, slowly discharge CO gas, then take out the reactor material, extract the reactor material twice with the organic solvent ethyl acetate, separate the catalyst aqueous phase and the product organic phase, and combine the extracted organic phase solution, the catalyst water phase continues to be recycl...

Embodiment 2

[0021] a. Add 60 mL of deoxygenated water (pH=7), 0.1 g of palladium acetate and 1 g of m-disulfonate triphenylphosphine ligand to the autoclave in turn, and stir at room temperature for 2 h after vacuuming;

[0022] B, add phase transfer agent sodium dodecylbenzene sulfonate 2g again, phosphoric acid 5g and purity are 75% substrate 1-octene 10g, airtight autoclave;

[0023] c. Replace the air in the kettle with high-purity CO gas for 3 times to reach a reaction temperature of 140°C, and press in 6MPa CO gas at one time to carry out a full carbonylation reaction for 12 hours;

[0024] d. After the reaction is completed, fully cool with an ice bath, slowly discharge CO gas, then take out the reactor material, extract the reactor material 4 times with the organic solvent ethyl acetate, separate the catalyst aqueous phase and the product organic phase, and combine the extracted organic phase solution, the catalyst water phase continues to be recycled, and then the combined produc...

Embodiment 3

[0026] a. Add 60 mL of deoxygenated water (pH=7), 0.1 g of palladium chloride and 5 g of m-trisulfonate triphenylphosphine ligand to the autoclave in sequence, and stir at room temperature for 1.5 h after vacuuming;

[0027] b. Add 2 g of cetyltrimethylammonium bromide as a phase transfer agent, 5 mL of concentrated hydrochloric acid and 10 g of substrate 1-octene with a purity of 99%, and seal the autoclave;

[0028] c. Replace the air in the kettle with high-purity CO gas for 5 times. After reaching the reaction temperature of 180°C, press in CO gas at a pressure of 12MPa at one time to carry out a full carbonylation reaction for 20 hours;

[0029] d. After the reaction is completed, fully cool with an ice bath, slowly discharge CO gas, then take out the reactor material, extract the reactor material 6 times with the organic solvent ethyl acetate, separate the catalyst aqueous phase and the product organic phase, and combine the extracted organic phase solution, the catalyst...

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Abstract

The invention discloses a method for preparing pelargonic acid and isononanoic acid by catalyzing 1-octylene through a water-soluble palladium-phosphine complex catalyst, comprising the following steps of: adding deoxygenated water, palladium acetate or palladium chloride as a catalyst and a water-soluble ligand in an autoclave, vacuumizing and stirring; adding a phase transfer agent, an acid addictive and the 1-octylene as a substrate; closing the autoclave and displacing the air in the autoclave with high-purity CO gas; and after reaching the reaction temperature, pressing the CO gas at one step and introducing the 1-octylene to carry out carbonylation with CO to obtain pelargonic acid and isononanoic acid. The product organic phase is easily separated from a catalyst water phase, thereby reducing the pollution of the catalyst to the products, saving the cost and realizing the continuous recycling of the catalyst.

Description

technical field [0001] The invention relates to a method for preparing nonanoic acid and isononanoic acid by catalyzing 1-octene with a water-soluble palladium-phosphine complex catalyst. Background technique [0002] Both nonanoic acid and isononanoic acid are very important organic raw materials, mainly used in the synthesis of fragrances and lubricating oils. At present, the preparation of nonanoic acid is mainly obtained by oxidation of oleic acid with nitric acid or ozone. Ozone oxidation of oleic acid is used to synthesize pelargonic acid, which has the advantages of environmentally friendly process and low pollution, but the ozonation of oleic acid not only obtains pelargonic acid, but also brings equimolar amounts of azelaic acid. The demand is limited, leading to an imbalance in the demand for nonanoic acid and azelaic acid. The use of 1-octene carbonylation to synthesize nonanoic acid can break the balance of the existing oleic acid oxidation process to prepare n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/14C07C53/126B01J31/24
CPCY02P20/584
Inventor 吾满江·艾力王永垒侯震山何珍红张乐涛
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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