Synthesis of plant growth hormone 3-indolebutyric acid

A technology of plant auxin and indole butyric acid, applied in the direction of organic chemistry, can solve the problems of harsh process conditions, large environmental pollution, high cost of raw materials, etc., and achieve the effect of simple synthesis process, avoiding environmental pollution, and low production cost

Inactive Publication Date: 2006-03-15
TIANJIN NORMAL UNIVERSITY
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Problems solved by technology

[0003] The purpose of the present invention is to carry out the research aimed at the above-mentioned problems, and solve the problems of high cost of raw materials, difficulty in obtaining, harsh process conditions, complex processes, and large environmental pollution caused; A new process for the synthesis of an environmentally friendly and energy-saving plant auxin 3-indolebutyric acid with greatly simplified synthesis steps

Method used

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  • Synthesis of plant growth hormone 3-indolebutyric acid

Examples

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example 1

[0017] Example 1. Under normal temperature and pressure, charge about 10 liters of hydrogen to the hydrogen metering bottle of the hydrogenation unit (until it is full), add 300ml (5.2mol) absolute ethanol, 13.8g (0.1mol) salicylic acid in the there-necked bottle and 3g of silicon dioxide-poly-γ-diphenylphosphinopropylsiloxane-platinum complex (Si-P-Pt), open the valve between the hydrogen metering device and the there-necked bottle, and make the hydrogen Press down to contact with the reaction solution, and after 30 minutes, 6.7 liters of hydrogen gas was absorbed. Separate the hydrogenation catalyst, then pour the reaction solution into a three-necked bottle, add 5g of 10-15 mesh perfluorosulfonic acid resin at the same time, install a reflux condenser and a thermometer, and reflux for 1.5 hours, then separate the perfluorosulfonic acid resin and recover it. Ethanol was distilled off again to obtain the product ethyl o-hydroxycyclohexyl carboxylate with a yield of 98.7%.

...

example 2

[0019] Example 2. hydrogenation unit, charging capacity and operating steps are the same as example 1, and the polymer hydrogenation catalyst is changed into 3g carbon fiber diphenylphosphine-palladium complex, after hydrogenation, carry out catalytic esterification again, obtain o-hydroxycyclohexyl formate ethyl ester, The yield was 95.5% based on salicylic acid.

example 3

[0020] Example 3. The polymer hydrogenation catalyst in Example 1 was replaced with 3g polystyrene-diphenylphosphine-palladium complex, reacted as above, and the calculated yield was 96.1%.

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Abstract

Synthesis of auxin 3-indolebutyric acid is carried out by catalytic hydrogenating for salicylic acid from polymer hydrogenation catalyst at normal temperature and pressure, esterifying with organic super acidic as catalyst with salicylic acid and alcohol=1: 20-1: 80, oxidation reacting from polymer oxidant at 70 Deg C. with saliclyl cyclomenthyl formate: polymer oxidant=1: 1.5-1: 2, condensation reacting at -5-10 Deg C., basic hydrolyzing under water bath condition, acidifying at room temperature with dimethylketone-2-ethyl formate: aniline=1: 1, re-arranging from Fischer, heating to 225-230 Deg C. and decarboxylation reacting. It costs low, has no environmental pollution and gentle reaction condition.

Description

technical field [0001] The invention relates to a synthesis process of plant auxin, in particular to a technology for process design with cheap salicylic acid as the starting material. Background technique [0002] 3-Indolebutyric acid is referred to as IBA for short, and it is a kind of auxin that naturally exists in plants. In order to better promote plant growth, therefore, synthetic IBA has been widely used. Years of practice have proved that the synthesized IBA is a high-efficiency, low-toxicity, high-activity, broad-spectrum pollution-free biochemical preparation. Accelerator. The synthesis process of the prior art has many steps and low conversion rate. Its main raw materials are indole, 4-chlorobutyronitrile or indole, γ-butyrolactone, etc. The synthesis of these raw materials is quite complicated, the process conditions are harsh, they are not easy to obtain, the cost is high, and they are easy to cause environmental pollution, resulting in 3-indole butyric acid ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/18
Inventor 赵增国张红艳刘尚远李伟
Owner TIANJIN NORMAL UNIVERSITY
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