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Preparation method of 4-tert-butyl phenylpropionaldehyde

A technology of tert-butylphenylpropionaldehyde and tert-butylstyrene, which is applied in the field of preparation of 4-tert-butylphenylpropionaldehyde, can solve the problems of difficult control of the reaction process, large quality differences, and great environmental hazards, and achieve Increased reaction rate and selectivity, low production cost, and low environmental hazards

Pending Publication Date: 2021-03-12
XIAN CATALYST NEW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Condensation is the most commonly used in the synthetic method of 4-tert-butylphenylpropanal in the prior art at present, is usually made up of multiple steps of condensation reaction, hydrogenation and hydrolysis, and raw material aldehyde is prepared through condensation reaction to obtain enal, Subsequent hydrogenation under the palladium carbon catalyst effect, obtains the product 4-tert-butylphenylpropionaldehyde, needs multiple steps in the condensation method preparation 4-tert-butylphenylpropionaldehyde, and the kind of raw material aldehyde is different in addition, the product 4- that obtains Tert-butylphenylpropionaldehyde often has large quality differences, and has defects such as high production costs, high difficulty in controlling the reaction process, and great environmental hazards.

Method used

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  • Preparation method of 4-tert-butyl phenylpropionaldehyde

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Embodiment 1

[0027] The present embodiment provides a kind of preparation method of 4-tert-butylphenylpropionaldehyde, comprises the following steps:

[0028] Step 1, 0.0360g rhodium catalyst and 0.2953g phosphine ligand are added in the polytetrafluoroethylene liner of autoclave; Described rhodium catalyst is Rh(CO) 2 C 5 h 7 o 2 , the phosphine ligand is two (2,4-dicumylphenyl) pentaerythritol diphosphite; the molecular formula of the two (2,4-dicumylphenyl) pentaerythritol diphosphite is C 33 h 50 o 6 P 2 , the molecular weight is 604.7;

[0029] Step 2: Add 20mL of 4-tert-butylstyrene, 100mL of dimethylformamide and 0.1800g of an organic base compound to the polytetrafluoroethylene lining of the autoclave described in step 1, add the rotor to cover the lid of the reaction kettle, Nitrogen is passed through for leak detection, and after confirming that there is no leak, it is replaced three times with nitrogen and then three times with a mixture of hydrogen and carbon monoxide to...

Embodiment 2

[0035] The present embodiment provides a kind of preparation method of 4-tert-butylphenylpropionaldehyde, comprises the following steps:

[0036] Step 1, add 0.0272g rhodium catalyst and 0.2230g phosphine ligand in the polytetrafluoroethylene lining of autoclave; Described rhodium catalyst is Rh(CO) 2 C 5 h 7 o 2 , the phosphine ligand is bis(2,4-dicumylphenyl) pentaerythritol diphosphite;

[0037] Step 2: Add 20mL of 4-tert-butylstyrene, 100mL of dimethylformamide and 0.1361g of an organic base compound to the polytetrafluoroethylene lining of the autoclave described in step 1, add the rotor to cover the lid of the reaction kettle, Nitrogen is passed through for leak detection, and after confirming that there is no leak, it is replaced three times with nitrogen and then three times with a mixture of hydrogen and carbon monoxide to obtain a mixed system; the organic base compound is triethylamine; the mixture of hydrogen and carbon monoxide is The volume ratio of hydrogen ...

Embodiment 3

[0040] The present embodiment provides a kind of preparation method of 4-tert-butylphenylpropionaldehyde, comprises the following steps:

[0041] Step 1, 0.0272g rhodium catalyst and 0.1727g phosphine ligand are added in the polytetrafluoroethylene liner of autoclave; Described rhodium catalyst is Rh(CO) 2 C 5 h 7 o 2 , the phosphine ligand is diphenyl phosphite;

[0042]Step 2: Add 20mL of 4-tert-butylstyrene, 100mL of dimethylformamide and 0.1361g of an organic base compound to the polytetrafluoroethylene lining of the autoclave described in step 1, add the rotor to cover the lid of the reaction kettle, Nitrogen gas is passed through for leak detection, and after confirming that there is no gas leak, it is replaced three times with nitrogen gas and then replaced three times with a mixture of hydrogen and carbon monoxide to obtain a mixed system; the organic base compound is N,N-diisopropylethylamine; the The volume ratio of hydrogen and carbon monoxide in the mixture of ...

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Abstract

The invention discloses a preparation method of 4-tert-butyl phenylpropionaldehyde, which comprises the following steps: carrying out hydroformylation reaction by using 4-tert-butyl styrene as a raw material to obtain 4-tert-butyl phenylpropionaldehyde, wherein the solvent is dimethylformamide, the catalyst is a rhodium catalyst, the rhodium catalyst is Rh(CO)2C5H7O2, RhHCO(PPh3)3 or Rh(C5H7O2)(CO)(PPh3), the auxiliary agent is a phosphine ligand and an organic alkali compound, the phosphine ligand is diphenyl phosphite, tris (o-methylphenylphosphine) or bis (2,4-dicumylphenyl)pentaerythritoldiphosphite, the organic alkali compound is triethylamine, triphenylphosphine oxide or N,N-diisopropylethylamine. According to the method, the 4-tert-butyl styrene is used as the raw material to prepare 4-tert-butyl phenylpropionaldehyde through one-step hydroformylation reaction, wherein the raw material conversion rate is higher than 98%, and the product yield is higher than 80%. The compound issimple in preparation method, low in production cost and small in environmental harm.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 4-tert-butylphenylpropionaldehyde. Background technique [0002] 4-tert-butylphenylpropionaldehyde, also known as Bojiehong aldehyde, is an intermediate in the synthesis of flavors and fragrances and a raw material in the food industry and pharmaceutical industry. As a strong and penetrating raw material, 4-tert-butylphenylpropionaldehyde It has a fresh lily-of-the-valley floral fragrance, accompanied by a watery green fragrance. Its unique lily-of-the-valley-aldehyde fragrance feature is widely used in cosmetics and perfumes. [0003] At present, most of my country's 4-tert-butylphenylpropanal depends on imports. However, with the continuous development of my country's national economy, the demand for 4-tert-butylphenylpropanal is also increasing. Therefore, it is necessary to develop a 4-tert-butyl The efficient and popularized synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/228B01J31/24B01J31/22
CPCC07C45/50B01J31/2213B01J31/2404B01J31/185B01J2531/822B01J2231/321C07C47/228Y02P20/584
Inventor 黄琼淋校大伟姚琪张高鹏李小安许涛涛高武
Owner XIAN CATALYST NEW MATERIALS CO LTD
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