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Method for synthesizing straight-chain octadecanedioic acid

An octadecanedioic acid and straight-chain technology, applied in the field of synthesizing straight-chain octadecanedioic acid, can solve the problems of complex process, inability to industrialize production, and high cost of synthesizing straight-chain octadecanedioic acid, and achieve simple raw materials, Easy mass production, low cost effect

Pending Publication Date: 2022-03-22
HANGZHOU ALLSINO CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a method for synthesizing straight-chain octadecanedioic acid in order to solve the problems that the existing method has high cost for synthesizing straight-chain octadecanedioic acid, complicated process, and impossibility for industrialized production. The readily available oleic acid is used as a raw material to generate diacids and long-chain hydrocarbons easily soluble in low-polarity organic solvents through metathesis, and then to synthesize straight-chain octadecanedioic acid through hydrogenation. The method of the present invention is easy to operate and simple in process , the raw materials are simple and easy to obtain, and the cost is low, which is suitable for both small-scale preparation in the laboratory and industrial production

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  • Method for synthesizing straight-chain octadecanedioic acid
  • Method for synthesizing straight-chain octadecanedioic acid

Examples

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Embodiment 1

[0029] This embodiment provides a method for synthesizing linear octadecanedioic acid, comprising:

[0030] a) Under nitrogen protection, add 2340.0 kg of n-heptane, 600.0 kg of oleic acid, and 1.0 kg of Grubbs (II) catalyst into a 5000L glass-lined reactor, stir and heat up to 35-45°C. Insulated and reacted for 5 hours, then cooled to room temperature 20-25 ° C, centrifuged, the filter cake was washed with 160.0 kg of n-heptane, and the filter cake was dried to obtain 260.0 kg of the compound shown in formula II (9-octadecenedioic acid) , yield 78.4%;

[0031] b) Under nitrogen protection, add 3000.0 kg of tetrahydrofuran and 260.0 kg of the compound represented by formula II into a 5000L glass-lined reactor. After stirring to dissolve, the solution was transferred to a 5000L hydrogenation tank. 18.0 kg of 5% wet palladium carbon was added to the hydrogenation kettle, and after nitrogen replacement, hydrogen replacement was carried out to keep the pressure in the kettle at ...

Embodiment 2

[0033] This embodiment provides a method for synthesizing linear octadecanedioic acid, comprising:

[0034] a) Under nitrogen protection, add 1200.0 kg of n-heptane, 300.0 kg of oleic acid, and 0.6 kg of Grubbs (II) catalyst into a 3000L glass-lined reactor; stir and heat up to 40-50°C. Insulate and react for 4 hours, then cool down to room temperature 20-25°C, centrifuge, wash the filter cake with 160.0kg n-heptane, and dry the filter cake to obtain 140.0kg of the compound (9-octadecenedioic acid) shown in formula II , yield 84.4%.

[0035] b) Under nitrogen protection, add 2000.0 kg of tetrahydrofuran and 180.0 kg of the compound represented by formula II into a 5000L glass-lined reactor. After stirring and dissolving, transfer to a 5000L hydrogenation tank. Then add 15.0 kg of 5% wet palladium carbon to the hydrogenation kettle; after nitrogen replacement, hydrogen replacement is carried out to keep the pressure in the kettle at 0.3-0.6 bar, stir and raise the temperature...

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Abstract

The invention provides a method for synthesizing straight-chain octadecanedioic acid, which comprises the following steps of: carrying out double decomposition reaction on a compound shown in a formula (I) under the condition of a Grubbs catalyst to generate an unsaturated acid compound shown in a formula (II); and reducing the compound as shown in the formula (II) into a compound as shown in a formula (III) through palladium-carbon hydrogenation. The method disclosed by the invention is convenient to operate, simple in process, simple and easily available in raw materials and low in cost, and is suitable for small-scale preparation in a laboratory and industrial production.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a method for synthesizing linear octadecanedioic acid by using oleic acid as a starting material through metathesis reaction and hydrogenation. Background technique [0002] Octadecanedioic acid is widely used and is an important chemical raw material. It is widely used in the structural modification of new medicines and the synthesis of special materials, such as nylon 1818. However, for the chemical preparation of octadecanedioic acid, so far there are few reports at home and abroad, resulting in high prices. It has been reported that 9-octadecenedioic acid ester is prepared by McMurry coupling reaction with 9-oxononanoic acid ester, and octadecanedioic acid (CN111302890A) is prepared through hydrogenation, hydrolysis and acidification or synthesized by 9-bromononanoic acid Corresponding Negishi reagent, and then through nickel-catalyzed self-coupling reacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/36C07C51/43C07C55/02C07C51/353C07C57/13
CPCC07C51/36C07C51/43C07C51/353C07C57/13C07C55/02
Inventor 李小清段亚亚张琦孔明熊卫宝李锋张芳东
Owner HANGZHOU ALLSINO CHEM
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