Method for preparing 3-methyl-3-butenal

A technology of crotonaldehyde and methyl, which is applied in the field of preparing 3-methyl-3-crotonaldehyde, can solve the problems such as difficult recycling, and achieve the effects of easy manipulation, avoiding high temperature conditions, and simple and easy method

Active Publication Date: 2019-03-08
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalyst is a homogeneous catalyst and is not easy to recycle

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A method for preparing 3-methyl-3-butenal, the steps are:

[0037] Under the protection of nitrogen atmosphere, 0.645g (5mmol) quinoline, 2g (5% palladium loading) palladium carbon, 85.5mg (0.25mmol) dicobalt octacarbonyl and 152.1g (1mol) citral were added into the autoclave. Replace with hydrogen for 6 times, and after the volume content of oxygen drops below 10ppm, start the heating button, raise the temperature of the reactor to 100°C, and keep the pressure at 0.5MPa. Add 86.1 g (1 mol) of 3-methyl-3-butenol into the reactor at a rate of 5 g / min, and keep the temperature of the reactor for 3 hours after the feeding is completed. The temperature of the reaction kettle was lowered, and the reaction solution was obtained by filtering after pressure release.

[0038] A small amount of the reaction liquid was analyzed by gas chromatography, and the composition of the reaction liquid was: 64.35% citronellal, 0.20% 3-methyl-3-butenol, 35.00% 3-methyl-3-butenal, and 0.45% ...

Embodiment 2

[0041] A method for preparing 3-methyl-3-butenal, the steps are:

[0042] Under the protection of nitrogen atmosphere, 1.033g (8mmol) quinoline, 5g (5% palladium loading) palladium carbon, 85.5mg (0.25mmol) dicobalt octacarbonyl and 153.7g (0.8mol) pseudoionone were added to the autoclave middle. Replace with hydrogen for 6 times, and after the volume content of oxygen drops below 10ppm, start the heating button, raise the temperature of the reactor to 60°C, and keep the pressure at 1.5MPa. Add 86.1 g (1 mol) of 3-methyl-3-butenol into the reactor at a rate of 5 g / min, and keep the temperature of the reactor for 5 hours after the feeding is completed. The temperature of the reaction kettle was lowered, and the reaction solution was obtained by filtering after pressure release.

[0043] A small amount of reaction solution was analyzed by gas chromatography, and the composition of the reaction solution was: 64.07% of dihydropseudoionone, 0.37% of 3-methyl-3-butenol, 34.34% of ...

Embodiment 3

[0045] A method for preparing 3-methyl-3-butenal, the steps are:

[0046] Under the protection of nitrogen atmosphere, 3.96g (50mmol) pyridine, 18g (5% palladium loading) palladium carbon, 80.6mg (0.16mmol) iron dodecacarbonyl and 152.1g (1mol) citral were added into the autoclave. Replace with hydrogen for 6 times, and after the volume content of oxygen drops below 10ppm, start the heating button, raise the temperature of the reactor to 100°C, and keep the pressure at 1.0MPa. Add 94.7 g (1.1 mol) of 3-methyl-3-butenol into the reactor at a rate of 5 g / min, and keep the temperature of the reactor for 8 hours after the feeding is completed. The temperature of the reaction kettle was lowered, and the reaction solution was obtained by filtering after pressure release.

[0047] A small amount of the reaction liquid was analyzed by gas chromatography. The composition of the reaction liquid was: 61.29% citronellal, 0.28% 3-methyl-3-butenol, 36.33% 3-methyl-3-butenal, and 2.10% othe...

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Abstract

The invention provides a method for preparing 3-methyl-3-butenal. The method includes: taking raw material 3-methyl-3-butenol as a hydrogen donor and a compound containing unsaturated bonds as a hydrogen receptor, and allowing intramolecular hydrogen transfer reaction under action of a catalyst system to obtain 3-methyl-3-butenal, wherein the catalyst system comprises azacycloligand, palladium carbon and metal carbonyl compound. The method is mild in reaction condition and easy in control, and product selectivity and raw material conversion rate are improved. Easy separation of 3-methyl-3-butenal can be realized by means of rectification; the method is simple and easy to implement and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for preparing 3-methyl-3-butenal, in particular to a method for preparing 3-methyl-3-butene from 3-methyl-3-butenol Aldehyde method. Background technique [0002] 3-methyl-3-butenal is an important organic intermediate for the production of citral, and the traditional production method is mainly to obtain 3-methyl-3-butenal by oxidation of 3-methyl-3-butenol. This method involves a dangerous oxidation process. Due to the large amount of heat released by the oxidation process, the requirements for the material and form of the reactor are harsh. The hydroxyl product is formed. [0003] BASF patent DE2041976 mainly discloses that copper and silver are used as main catalysts to add alkali metal oxides or use alkali metal oxides as carriers to catalyze the oxidation of 3-methyl-2-butenol to obtain 3-methyl-2-butenal In order to reduce side reactions, silver with go...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C47/21
CPCC07C45/002C07C47/21
Inventor 鲍元野王文张永振黎源
Owner WANHUA CHEM GRP CO LTD
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