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Method for synthesizing 3-methyl-2-butene aldehyde

A synthetic method and technology of crotonaldehyde, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of many by-products and poor selectivity, and achieve less side reactions, less environmental pollution, and The effect of mild reaction conditions

Inactive Publication Date: 2010-05-19
ZHEJIANG MEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In DE-2517859, a tubular reactor is used at 150-300°C in an excess oxygen atmosphere to catalyze the oxidation of 3-methyl-2-butenol by copper to synthesize 3-methyl-2-butenal. More by-products, poor selectivity

Method used

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  • Method for synthesizing 3-methyl-2-butene aldehyde
  • Method for synthesizing 3-methyl-2-butene aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 250ml three-necked round bottom flask equipped with magnetic stirring, 12.9g (0.15mol) of 3-methyl-2-butenol and 100ml of dichloromethane as a solvent were added, and replaced by nitrogen gas. Add 2.0 g (5 mmol) of ferric nitrate nonahydrate and 0.71 g (4.5 mmol) of TEMPO, and slowly introduce pure oxygen at 25°C. After reacting for about 6 hours, the conversion rate of 3-methyl-2-butenol was 99%. The obtained reaction liquid was filtered, and the solvent was distilled off to obtain 11.9 g of 3-methyl-2-butenal (the content detected by gas chromatography was 97.7%), and the yield was 92.3%.

Embodiment 2

[0022] In a 250ml three-neck round bottom flask equipped with magnetic stirring, 12.9g (0.15mol) of 3-methyl-2-butenol and 100ml of solvent toluene were added, and replaced by nitrogen gas. Add 1.4 g (5 mmol) of cobalt nitrate and 0.71 g (4.5 mmol) of 4-OCH3-TEMPO, and slowly introduce air at 70°C. After reacting for about 14 hours, the conversion rate of 3-methyl-2-butenol was 95%. The reaction solution was filtered, and the solvent was distilled off to obtain 10.8 g of 3-methyl-2-butenal (content: 95.2%), with a yield of 81.6%.

Embodiment 3

[0024] In a 250ml three-necked round bottom flask equipped with magnetic stirring, 12.9g (0.15mol) of 3-methyl-2-butenol and 100ml of solvent cyclohexane were added, and replaced by nitrogen gas. Add 0.84 g (3 mmol) of manganese nitrate and 0.51 g (3 mmol) of 4-O-TEMPO, and slowly introduce air at 20°C. After reacting for about 8 hours, the conversion rate of 3-methyl-2-butenol was 97%. The resulting reaction solution was filtered, and the solvent was evaporated to obtain 11.3 g of 3-methyl-2-butenal (content 96.8%), with a yield of 86.8%.

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Abstract

The invention discloses a method for synthesizing intermediate of 3-methyl-2-butene aldehyde which is used for synthesizing the medicine and the spice, aiming at solving the problems of low conversion rate, many by-products from some reaction and poor selectivity in the prior method for synthesizing the intermediate of 3-methyl-2-butene aldehyde. The 3-methyl-2-butene aldehyde is prepared by catalyzing and oxidizing 3-methyl-2-butenol which is used as raw material with the oxygen-containing gas which is used as oxidant at room temperature or heating condition. The method for synthesizing the 3-methyl-2-butene aldehyde is characterized in that the catalyst used in the reaction is 2, 2, 6, 6-tetramethyl piperidine nitroxide radical compound, and the additive used in the reaction is iron nitrate, cobalt nitrate or manganese nitrate. The catalyst can be used for high selectively synthesizing the 3-methyl-2-butene aldehyde, is environmental friendly and can be recycled. The method for synthesizing the 3-methyl-2-butene aldehyde ensures the mild reaction condition, the little side reaction and the high reaction yield.

Description

technical field [0001] The invention relates to a method for synthesizing intermediate 3-methyl-2-butenal for synthesizing medicine and spices. Background technique [0002] 3-methyl-2-butenal, also known as isopentenal, is the raw material for the synthesis of isophytic alcohol; it can also be used as the starting material for the synthesis of citral, and then for the production of vitamin A, vitamin E, and β-carotene; It can also be used to synthesize spices such as ironone and damascenone. [0003] JP-60 / 246340 reported that 3-methyl-2-butenal was prepared by oxygen oxidation of 3-methyl-2-butenol at 400-500°C using a silver and copper composite catalyst loaded on a carrier. The selectivity can reach 96%, but high temperature is required, and the conversion rate of 3-methyl-2-butenol is low. In DE-2517859, a tubular reactor is used at 150-300°C in an excess oxygen atmosphere to catalyze the oxidation of 3-methyl-2-butenol by copper to synthesize 3-methyl-2-butenal. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/21C07C45/38B01J31/02
CPCY02P20/584
Inventor 胡赞喜梁智平王渭军于绪平汪国炎孟喻剑
Owner ZHEJIANG MEDICINE CO LTD
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