Ethylene antagonist and preparation method thereof

An antagonist and ethylene technology, applied in the field of ethylene antagonists and its preparation, can solve the problems of adverse effects on the environment and equipment, human injury, large amount of by-product waste acid, etc., to avoid corrosive hydrochloric acid gas and high yield Effects on economy, reduction of environmental and equipment hazards

Inactive Publication Date: 2019-06-28
西安集佰侬生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] The present invention provides an ethylene antagonist and a preparation method thereof, one of the purposes of which is to solve the problems that the existing ethylene antagonists have greater damage to the human body and cause hidden dangers of withering to crops to be kept fresh; The second is to solve the problems of low synthesis yield and large amount of by-product waste acid in the preparation method, which will cause adverse effects on the environment and equipment.

Method used

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  • Ethylene antagonist and preparation method thereof
  • Ethylene antagonist and preparation method thereof
  • Ethylene antagonist and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0033] The preparation method of an ethylene antagonist provided by the invention is obtained through the reaction of isopropylidene aminooxyacetic acid and non-volatile acid.

[0034] The specific preparation method is: heating isopropylidene aminooxyacetic acid in an aqueous solution of a non-volatile acid to remove the protective group to generate a salt of aminooxyacetic acid, and detect when the residual amount of isopropylidene aminooxyacetic acid in the raw material is <0.1%. It is the end point of the reaction; the obtained product aqueous solution is concentrated under reduced pressure to remove part of the water; then an alcoholic organic solvent is added to crystallize the salt, and cooled and stirred to complete the crystallization; then the solvent is removed by filtration, and the filter cake is washed with an alcoholic solvent and dried to obtain the final product .

Embodiment 1

[0036] Add 26 grams (0.2 moles) of isopropylidene aminooxyacetic acid into 200 ml of 1 mol / liter sulfuric acid aqueous solution and heat to reflux at 100°C for 15 hours, (the residual amount of isopropylidene aminooxyacetic acid in the raw material is detected <0.1%) , and then the reaction solution was concentrated under reduced pressure to 50 ml. Then 200 milliliters of isopropanol was added under stirring while hot, and a large amount of white crystals could be observed to separate out. The temperature of the system was lowered to 0°C-5°C, stirred and crystallized for 2 hours, then filtered, and the filter cake was washed with 40 ml of cold isopropanol, and vacuum-dried to obtain 25.2 g of aminooxyacetic acid sulfate (90% molar yield). The molar ratio of aminooxyacetic acid to sulfate in the obtained sulfate is 2:1, that is, one molecule of sulfate can form a salt with two molecules of aminooxyacetic acid. The reaction equation is as follows:

[0037]

Embodiment 2

[0039] 26 grams (0.2 moles) of isopropylidene aminooxyacetic acid was added to 200 milliliters of 1.5 mol / liter phosphoric acid aqueous solution and heated to reflux at 80°C for 20 hours (the residual amount of isopropylidene aminooxyacetic acid in the raw material was detected <0.1%), Then the reaction solution was concentrated under reduced pressure to 60 mL. Then, 200 milliliters of isopropanol was added under stirring while hot, and a large amount of white crystals could be observed to separate out. The temperature of the system was lowered to 0°C-5°C, stirred and crystallized for 2 hours, then filtered, and the filter cake was washed with 40 ml of cold isopropanol, and then vacuum-dried to obtain 33.6 g of aminooxyacetic acid phosphate (89% molar yield). The molar ratio of aminooxyacetic acid to phosphate in the obtained phosphate is 1:1, that is, one molecule of phosphate can form a salt with one molecule of aminooxyacetic acid. The reaction equation is as follows:

[00...

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Abstract

The invention belongs to the technical field of organic chemical synthesis and particularly relates to an ethylene antagonist and a preparation method thereof. The first purpose of the invention is tosolve the problems that an existing ethylene antagonist is relatively harmful to a human body, and to-be-preserved crops are easily withered; and the second purpose of the invention is to solve the problems that an existing preparation method is low in synthetic yield, the generation amount of a byproduct, namely waste acid is relatively large, and adverse influences are caused to the environmentand equipment. The preparation method comprises the following steps: heating isopropyl aminooxyeacetic acid in a non-volatile acid water solution to remove protecting groups so as to generate salt ofaminooxyacetic acid, wherein the reaction terminal is arrived when the residual amount of isopropyl aminooxyeacetic acid is less than 0.1%; carrying out reduced pressure concentration on the obtainedproduct water solution so as to remove partial moisture; adding an alcohol organic solvent so as to crystalize salt, cooling, and stirring so as to realize complete crystallization; and filtering toremove the solvent, washing a filter cake by virtue of an alcohol solvent, and drying, so as to obtain a finial product.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to an ethylene antagonist and a preparation method thereof. Background technique [0002] Ethylene is a substance with the simplest molecular structure among plant hormones. It is gaseous under normal conditions, and it is closely related to the physiological process of plants. It can accelerate the ripening of fruits, the senescence and shedding of leaves, the opening and withering of flowers and regulate the growth of plants. Ethylene can be divided into endogenous and exogenous according to the source. Endogenous ethylene is produced by the plant itself, while other sources can be called exogenous ethylene. In many cases, people need to eliminate some adverse effects of ethylene, such as preservation of flowers and fruits, regulation of plant growth height, etc. Commonly used ethylene antagonists include 1-methylcyclopropene (1-MCP), aminooxyethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/00A01N3/02
CPCY02P20/55
Inventor 王慎谦
Owner 西安集佰侬生物科技有限公司
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