Method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol

A technology of propargyl alcohol and allyl alcohol, applied in hydrogenation preparation, organic chemistry, etc., can solve the problems of low selectivity, serious catalyst loss, and low selectivity of allyl alcohol, and achieve low catalyst unit consumption, The effect of low stirring speed and stable catalyst

Active Publication Date: 2015-12-23
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] (1) Conversion rate of propargyl alcohols, low selectivity of allyl alcohol, high selectivity of overhydrogenation products, high waste, low yield
[0012] (2) The solid-supported catalytic system is used in the prior art, and the reaction system is a solid-liquid-gas three-phase reaction. The reaction requires high-intensity stirring to make the catalyst evenly dispersed in the system. Uneven catalyst loading or uneven dispersion will lead to local Catalyst concentration too high, resulting in low selectivity and high waste
[0013] (3) Catalyst separation is complicated, requiring long-term sedimentation and filtration, serious loss of catalyst, and cumbersome operation process

Method used

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  • Method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol
  • Method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 A kind of method for the selective hydrogenation of propargyl alcohol to prepare allyl alcohol

[0039] The propargyl alcohol is methyl butynol, and the allyl alcohol is methyl butenol.

[0040] Described method comprises the following steps:

[0041] (1) Feeding

[0042] A complex catalyst of 3g ammonium chloroplatinite and sodium triphenylphosphine intersulfonate, and 100g water were added to a 1L autoclave with magnetic stirring and a temperature controller, and then 200g methyl butynol was added; complexation The mass ratio of platinum chloride and sodium triphenylphosphine intersulfonate in the product is 0.01:1.

[0043] (2) Nitrogen, hydrogen replacement

[0044] It was replaced three times with nitrogen and three times with hydrogen.

[0045] (3) Hydrogenation reaction

[0046] Heat to 70°C, increase the hydrogen pressure to 2.0MPa, stir at 200rpm, react for 8 hours, take a sample and analyze the conversion rate of methyl butynol >99.9%, stop...

Embodiment 2

[0051] Embodiment 2 A method for preparing allyl alcohol by selective hydrogenation of propargyl alcohol

[0052] The propargyl alcohol is dehydrolinalool, and the allyl alcohol is linalool.

[0053] Described method comprises the following steps:

[0054] (1) Feeding

[0055] Add 6g of palladium chloride and tri-(2,4-dimethyl-5-sodium sulfonate phenyl) phosphine complex catalyst, 200g of water into a 1L autoclave with magnetic stirring and temperature controller, and then Add 200 g of dehydrolinalool; the mass ratio of the complex palladium chloride to tris-(2,4-dimethyl-5-sulfonate sodium phenyl)phosphine is 0.008:1.

[0056] (2) Nitrogen, hydrogen replacement

[0057] It was replaced three times with nitrogen and three times with hydrogen.

[0058] (3) Hydrogenation reaction

[0059] Heating to 80°C, increasing the hydrogen pressure to 2.0MPa, stirring at 400rpm, and reacting for 15 hours, sampling and analyzing the conversion rate of dehydrolinalool>99.9%, and the r...

Embodiment 3

[0064] Embodiment 3 A kind of method for the selective hydrogenation of propargyl alcohol to prepare allyl alcohol

[0065] The propargyl alcohol is dehydronerolidol, and the allyl alcohol is nerolidol.

[0066] Described method comprises the following steps:

[0067] (1) Feeding

[0068] Add the complex catalyst of 8g palladium chloride and tris-(2-sodium sulfonate dibenzofuryl) phosphine, 200g water into a 1L autoclave with magnetic stirring and temperature controller, and then add dehydroneroli 200g of tertiary alcohol; the mass ratio of complex palladium chloride to tris-(2-sodium sulfonate dibenzofuryl)phosphine is 0.006:1.

[0069] (2) Nitrogen, hydrogen replacement

[0070] It was replaced three times with nitrogen and three times with hydrogen.

[0071] (3) Hydrogenation reaction

[0072] Heating to 80°C, increasing the hydrogen pressure to 2.0MPa, stirring at 400rpm, and reacting for 17 hours, sampling and analyzing the conversion rate of nerolidol >99.9%.

[...

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Abstract

The invention provides a method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol. According to existing methods for synthesis of allyl alcohol through hydrogenation of propargyl alcohol, an immobilized heterogeneous catalysis system is adopted mostly, and high conversion rate, high selectivity and low leftover rate are hard to realize at the same time. The method is characterized in that the weaknesses of an immobilized catalyst are avoided, and VIII-group water-soluble metal salt and a water-soluble ligand are adopted for complexing to form a complex catalyst so as to achieve water-organic biphasic hydrogenation reaction. The method comprises the steps of material charging, nitrogen and hydrogen replacement, and hydrogenation reaction. During material charging, 0.1-5 parts of water and 0.005-0.1 part of catalyst are added to a kettle, and then 1 part of propargyl alcohol is added. The conversion rate of propargyl alcohol is 99.9-99.99%, gas phase selectivity is high, and yield is high; the catalyst is evenly and stably dispersed, unit consumption is low, recycling can be conducted for more than 30 times, the catalyst, the product and a catalytic system are easy to separate, operation is easy, and the method is suitable for industrial production.

Description

technical field [0001] The present invention relates to a method for producing VE main intermediate, DV chrysanthemic acid (pyrethrin intermediate), synthetic vitamin A, vitamin K1, carotenoid intermediate, synthetic rubber monomer and perfume, specifically a kind of propargyl The invention discloses a method for preparing allyl alcohol through selective hydrogenation of base alcohol in water-organic two-phase, belonging to the technical field of organic synthesis. Background technique [0002] Allyl alcohol is a method for fine chemical industry to prepare intermediates and chemical products. It is mainly used for the production of VE main intermediates, DV chrysanthemic acid (pyrethrin intermediates), synthetic vitamin A, vitamin K1, and carotenoid intermediates , synthetic rubber monomers and fragrances. [0003] Its general reaction formula is: [0004] [0005] Wherein, R1, R2 are hydrogen or hydrocarbon group. [0006] The selective hydrogenation of propargyl alc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/03C07C29/17C07C33/02
CPCC07C29/17C07C33/03C07C33/02
Inventor 马啸鲁光银赵文乐马书召张相如陈为超
Owner SHANDONG NHU PHARMA
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