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Method for preparing alpha, beta unsaturated alcohol from compound of ketone or aldehyde containing carbonyl

An aldehyde compound and unsaturated technology, which is applied in the preparation of hydroxyl compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of excessive reduction product yield, lower product quality, air pollution, etc., and achieve easy control of the reaction , Improve the purity and quality, and reduce the pollution load

Inactive Publication Date: 2005-08-31
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

α, the partial hydrogenation reduction of β-unsaturated acetylenic alcohol product, except the Lindlar catalyst that can use Pd content 0.25%, can also use the catalyst that noble metals such as: nickel, cobalt, palladium, platinum, rhodium, iridium etc. make, also can use Na, LiAlH can be used 4 Wait for the reducing agent to reduce, but it is easy to reduce the product yield and product quality due to excessive reduction
The main disadvantage of the "ethynylation reduction method" is the need for low temperature and a large amount of liquid ammonia, strict operating requirements, a high-pressure closed reaction system, and a decompression evaporation and compression recovery treatment device, the possibility of air pollution caused by a large amount of ammonia overflow very big

Method used

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  • Method for preparing alpha, beta unsaturated alcohol from compound of ketone or aldehyde containing carbonyl
  • Method for preparing alpha, beta unsaturated alcohol from compound of ketone or aldehyde containing carbonyl
  • Method for preparing alpha, beta unsaturated alcohol from compound of ketone or aldehyde containing carbonyl

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Experimental program
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Effect test

Embodiment 1

[0046] A method for preparing α, β-unsaturated alcohols from carbonyl-containing ketones or aldehydes, the carbonyl-containing ketones or aldehydes can be: general formula R 1 COR 2 Ketone compounds, in this embodiment can be methyl heptenone, geranyl acetone, neryl acetone, farnesyl acetone, phytoketone, cyclohexanone, etc., the general formula is R 1 Aldehyde compounds of CHO, such as citral, geranial, neral, citronellal, vanillin, trimethoxybenzaldehyde, benzaldehyde. In this embodiment, the carbonyl-containing ketone compound is a terpene-based acetone compound, which can obtain better results, and the effect when the terpene-based acetone compound is geranyl acetone, neryl acetone, farnesyl acetone and phytoketone better.

[0047] Ethynylation of carbonyl-containing ketones or aldehydes:

[0048] The first step: put a strong base compound equivalent to 1 to 5 times the molar mass of carbonyl-containing ketones or aldehydes and an organic solvent equivalent to 5 to 15 t...

Embodiment 2

[0059] Preparation of dehydronerolidol with geranylacetone as raw material:

[0060] Add 0.35mol potassium hydroxide powder and 200mL organic solvent (tetrahydrofuran or toluene) to a 250mL four-necked bottle, place in a liquid bath at -20 to 10°C and stir to make the temperature reach internal and external equilibrium, and then pass through acetylene gas to replace and remove the reaction. The air in the container is then continuously fed with acetylene gas. The reaction is carried out in a simple airtight balloon system with a pressure of 0.1-0.25 MPa to avoid the overflow and loss of acetylene gas. After 0.5 hours, slowly drop through the constant pressure dropping funnel. Add 0.1mol (19.4g, about 22.3mL, if necessary, dilute with a little solvent) geranyl acetone. After the dropwise addition, continue to keep warm and stir until the reaction is over. The reaction time is 0.5~100h. During the reaction, keep the reactants in the reactor in an acetylene atmosphere with a pres...

Embodiment 3

[0064] Other conditions in Implementation 2 are unchanged, only the solvent used is changed, and then the same ethynylation reaction is carried out. The obtained results are shown in Table 1.

[0065] no

[0066] All hydrogenation reaction conditions in embodiment 2 do not change, carry out the same selective hydrogenation reaction as embodiment 2, make nerolidol.

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PUM

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Abstract

A process for preparing unsaturated alpha, beta-alcohol from the carbonyl contained ketone or aldehyde compound includes mixing strong-alkaline compound with organic solvent, filling acetylene gas, dropping carbonyl contained ketone or aldehyde compound, reaction while stirring, solid-liquid separation to remove solid alkali, adding acidic compound, releasing unsaturated alpha, beta-ethynol, water washing to obtain liquid product of unsaturated alpha, beta-ethynol, vacuum distilling to obtain unsaturated alpha, beta-ethynol, and hydrogenating to obtain unsaturated alpha, beta-enol.

Description

technical field [0001] The invention relates to a method for preparing α, β-unsaturated alcohols, in particular to a method for preparing α, β-unsaturated alkynols or α, β-unsaturated enols from carbonyl-containing ketones or aldehyde compounds. Background technique [0002] As long as the α, β-position contains unsaturated bond alcohol compounds can be called α, β-unsaturated alcohol compounds, but in general, α, β-unsaturated alcohol compounds mainly refer to α, β- Alcohol compounds containing unsaturated C=C bonds or C≡C bonds. Through the addition reaction of ketones or aldehydes containing carbonyl groups with compounds containing alkene groups such as vinyl or alkyne groups such as ethynyl, α, β-unsaturated alcohols containing allyl groups or containing propargyl groups can be generated. α,β-unsaturated alcohols. α, β-unsaturated alcohols are very important compounds, especially most of them are important spices or pharmaceutical int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/38C07C33/02
Inventor 赵振东毕良武李冬梅王婧古研刘先章
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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