Preparation method of allylic alcohol

A technology of isopentenol and butene, applied in the direction of isomerization preparation, chemical instruments and methods, organic compound/hydride/coordination complex catalyst, etc., can solve difficult guarantee, difficult separation, affecting yield, etc. problems, to achieve the effect of high raw material conversion rate and product selectivity, low reaction temperature, and many application times

Inactive Publication Date: 2020-02-07
CHAMBROAD CHEM IND RES INST CO LTD
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

In order to reduce the coking of the catalyst, hydrogen can be passed through during the isomerization reaction, but this will cause hydrogenation of double bonds to produce a small amount of saturated alcohol by-products
[0014] The above-mentioned catalytic transposition reactions are all in the presence of a catalyst, through the isomerization reaction in the hydrogen atmosphere to generate isopentenol, the participation of hydrogen will inevitably lead to the generation of isoamyl alcohol, it is difficult to ensure a higher isoamyl alcohol in the isomerization reaction Selectivity, at the same time, because isoamyl alcohol is close to the boiling point of raw material 3-methyl-3-buten-1-ol, it is difficult to separate, resulting in increased energy consumption when reclaiming 3-methyl-3-buten-1-ol , and affect the yield

Method used

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  • Preparation method of allylic alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Weigh 0.165g of bisphosphine ligand 1,3-bis(diphenylphosphine)propane (DPPP), 0.089g of transition metal compound such as palladium acetate, add them into a three-necked flask, add 100ml of acetone, replace with nitrogen for 3 times, at 28°C Stir for 25 minutes, then stop the reaction, and spin dry at 50° C. to obtain 0.15 g of the complex catalyst with the chelate structure.

[0030] Add 150 grams of 3-methyl-3-buten-1-ol and 0.15 g of the catalyst prepared by the above method into a 500 m autoclave, replace the nitrogen three times, keep the hydrogen pressure at 0.7 Mpa, control the temperature at 55 ° C, and rotate at 200 rpm After reacting for 60 minutes, stop the reaction, ventilate and filter to obtain 150 g of prenol, with a selectivity of 95.21% and a conversion rate of 79.18%.

Embodiment 2

[0032] Weigh 0.165g of bisphosphine ligand 1,3-bis(diphenylphosphine)propane (DPPP) and 0.098g of transition metal compound such as palladium acetate into a three-neck flask, add 150ml of acetone, replace with nitrogen for 3 times, at 25°C Stir for 30 minutes, then stop the reaction, and spin dry at 50° C. to obtain 0.16 g of the complex catalyst with the chelate structure.

[0033] Add 150 grams of 3-methyl-3-buten-1-ol and 0.075 g of the catalyst prepared by the above method into a 500m autoclave, replace with nitrogen three times, keep the pressure of hydrogen at 1.0Mpa, control the temperature at 50°C, and rotate at 50 rpm After reacting for 20 minutes, the reaction was stopped, and the gas was ventilated and filtered to obtain 169.1 g of prenol, with a selectivity of 95.34% and a conversion rate of 89.26%.

Embodiment 3

[0035]Weigh 0.165g of bisphosphine ligand 1,3-bis(diphenylphosphine)propane (DPPP), 0.108g of transition metal compound such as palladium acetate (molar ratio 1:1.2), add them into a three-necked flask, add 150ml of acetone, Replaced with nitrogen three times, stirred at 23°C for 35 minutes, then stopped the reaction, and spin-dried in vacuum at 50°C to obtain 0.14 g of the complex catalyst with the chelate structure.

[0036] Add 150g of 3-methyl-3-buten-1-ol and 0.105g of the catalyst prepared by the above method into a 500m autoclave, replace with nitrogen 3 times, keep the pressure of hydrogen at 1.2Mpa, control the temperature at 70°C, and react at 400 rpm for 90 minutes, the reaction was stopped, and the gas was vented and filtered to obtain 174.8 g of prenol, with a selectivity of 95.97% and a conversion rate of 92.35%.

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Abstract

The invention belongs to the technical field of fine chemical industry. A heterogeneous catalyst technology is adopted, a complex catalyst is of a chelate structure and is formed by diphosphine ligandand transition metal compounds, the complex catalyst is used for catalyzing heterogeneous rearrangement of 3-methyl-3-butene-1-alcohol, production of by-products such as isoamyl alcohol and isopreneare inhibited at the same time, the conversion rate of raw materials is increased, and the product selectivity is improved. The invention provides a preparation method of the catalyst. The invention relates to a preparation method of allylic alcohol. Preparation is carried out by adopting a 3-methyl-3-butene-1-alcohol heterogeneous rearrangement technology. The preparation method is characterizedin that heterogeneous rearrangement is completed with the 1,3-bi(diphenylphosphine)propane-palladium-acetate chelate complex as the catalyst and on the conditions that hydrogen exists, the temperatureranges from 50 DEG C to 80 DEG C, and the time ranges from 20 minutes to 2 hours. According to the preparation method, the raw materials are easy to get, the cost is low, the repeated usage time number of catalysts is large, no three wastes are produced, and the energy consumption is low; and because of energy saving, consumption reduction and environmental protection, and the high conversion rate of the raw materials and the high product selectivity, the preparation method is suitable for preparing allylic alcohol and is especially suitable for preparing high-quality allylic alcohol.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to chemical synthesis technology, in particular to the preparation technology of isopentenol. Background technique [0002] The main application of isopentenol: used in rubber accelerators, intermediates in the synthesis of high-efficiency and low-toxicity pesticides pyrethroids insecticides, and its downstream products permethrin, DV chrysanthemum Chrysanthemum acid chloride), etc., can also be used as an intermediate in the synthesis of fragrances. With people's continuous research on the synthesis process of prenol and the continuous deepening of application development, its application range will also continue to expand, and its demand will also increase significantly. Especially as a raw material for the synthesis of vitamin E, it is used in a large amount. At the same time, this product is an intermediate of the drug neovacdin and has a wide range of uses. Therefore, it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/56C07C33/025B01J31/24
CPCC07C29/56B01J31/2409B01J2531/0213B01J2531/824C07C33/025
Inventor 王旭亮张凤崎郭龙龙龙显灵杨鹏飞刘鹏
Owner CHAMBROAD CHEM IND RES INST CO LTD
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