Preparation method of octadecanedioic acid

A technology of octadecanedioic acid and octadecanedioic acid dimethyl, which is applied in the field of preparation of octadecanedioic acid, can solve the problems of being unsuitable for industrial production, octadecanedioic acid is not environmentally friendly, and the preparation cost is high. Achieve the effect of being beneficial to environmental protection, improving the purification steps, and shortening the synthesis steps

Inactive Publication Date: 2020-06-19
CHANGZHOU INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the defects that the method for preparing octadecanedioic acid in the prior art is not environmentally friendly, not suitable for industrial production, and has high preparation costs, a method for preparing octadecanedioic acid is provided. The method of the present invention has low preparation cost and high yield. high

Method used

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  • Preparation method of octadecanedioic acid
  • Preparation method of octadecanedioic acid
  • Preparation method of octadecanedioic acid

Examples

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Effect test

Embodiment 1

[0031] A preparation method of octadecanedioic acid, comprising the steps of:

[0032] (1) prepare the coupling intermediate shown in formula III:

[0033]

[0034] Under nitrogen atmosphere, in a 1000 ml three-neck flask equipped with a mechanical stirring device, add 26 grams (400 mmol) of zinc powder and 250 ml of tetrahydrofuran solution, and add dropwise with a constant pressure dropping funnel under continuous stirring. Titanium trichloride liquid (wherein titanium trichloride 100 millimoles), be warming up to 45 ℃ after dropwise addition, heat and stir reaction 1 hour to generate zero-valent titanium;

[0035] After cooling down to the range of 0°C to 5°C with an ice bath, add the starting material 9-oxononanoic acid methyl ester (18.6 grams, 100 mmoles) dropwise with a constant pressure dropping funnel. ) in tetrahydrofuran (50 milliliters), then warming up to 60°C and stirring for 16 hours to carry out McMurry coupling reaction (McMurry Coupling), after the reacti...

Embodiment 2

[0044] A preparation method of octadecanedioic acid, comprising the steps of:

[0045] (1) prepare the coupling intermediate shown in formula III:

[0046]

[0047] Under nitrogen atmosphere, in a 2000 ml three-necked flask equipped with a mechanical stirring device, add 39.2 g (600 mmol) of zinc powder and 500 ml of tetrahydrofuran solution, under continuous stirring, add dropwise with a constant pressure dropping funnel Titanium trichloride liquid (wherein titanium trichloride 200 millimoles), be warming up to 35 ℃ after dropwise addition, heat and stir reaction 4 hours to generate zero-valent titanium;

[0048] After cooling down to the range of 0°C to 5°C with an ice bath, add the starting material 9-oxononanoic acid methyl ester (37.2 grams, 200 mmoles) dropwise with a constant pressure dropping funnel. ) THF solution (100 milliliters), then warming up to 45 ° C and stirring for 24 hours to carry out McMurry coupling reaction (McMurry Coupling), after the reaction was...

Embodiment 3

[0057] A preparation method of octadecanedioic acid, comprising the steps of:

[0058] (1) prepare the coupling intermediate shown in formula III:

[0059]

[0060] Under nitrogen atmosphere, in a 2000 ml three-neck flask equipped with a mechanical stirring device, add 52.3 g (800 mmol) of zinc powder and 500 ml of tetrahydrofuran solution, under continuous stirring, add dropwise with a constant pressure dropping funnel Titanium trichloride liquid (wherein titanium trichloride 400 millimoles), be warming up to 60 ℃ of heating and stirring reaction for 1 hour to generate zero-valent titanium after dropwise addition;

[0061] After cooling down to the range of 0°C to 5°C with an ice bath, add the starting material 9-oxononanoic acid methyl ester (18.6 grams, 100 mmoles) dropwise with a constant pressure dropping funnel. ) in tetrahydrofuran (50 milliliters), then warming up to 70°C and stirring for 8 hours to carry out McMurry coupling reaction (McMurry Coupling), after the ...

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Abstract

The invention relates to a preparation method of octadecanedioic acid, which comprises the following steps: carrying out McMurry coupling reaction on 9-oxononanoic acid methyl ester as an initial rawmaterial under the promotion of low-valent titanium to form a coupling intermediate; carrying out double bond reduction on the coupling intermediate under palladium-carbon catalytic hydrogenation to form dimethyl octadecanedioate; and finally, hydrolyzing the dimethyl octadecanedioate to obtain the target product octadecanedioic acid with high yield and high purity. The method has the advantages of cheap and accessible raw materials and simple post-treatment steps, does not involve highly toxic substances such as heavy metals, and is beneficial to environmental protection. Furthermore, the separation and purification method of the target product is very simple, the production cost and sales unit price of the octadecanedioic acid can be greatly reduced, so that the synthesis, preparation and development of various novel medicines and other materials taking the octadecanedioic acid as a raw material are facilitated, the research and development of medical intermediates taking the octadecanedioic acid as a raw material are also facilitated, and the commercial value is relatively high.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of octadecanedioic acid. Background technique [0002] Long-chain dibasic acid compounds are very important raw materials for the chemical industry. They are industrially used to manufacture high-performance nylon materials, pesticides, and important pharmaceutical intermediates. They can also be used in advanced hot-melt adhesives and advanced coatings. It is a kind of high-grade chemical raw materials with wide demand. However, due to its special structure, it cannot be obtained from nature and can only be synthesized by chemical or biological methods, so their prices have remained high. Octadecanedioic acid is an extremely important kind of long-chain dibasic acid. Due to its wide application range, new medicines, special materials (such as nylon 1818) and advanced coatings produced with it as raw materials have excellent performance. However, du...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/02C07C55/02C07C67/343C07C69/593C07C67/303C07C69/34
CPCC07C51/09C07C67/303C07C67/343C07C55/02C07C69/593C07C69/34
Inventor 吴泽颖孟佳瑶曹桂萍壮亚峰刘宝亮张震威向梅丁琳琳魏雪姣
Owner CHANGZHOU INST OF TECH
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