Synthetic method of trans-4-acetoxyl-2-methyl-2-butene-1-aldehyde

An acetoxy and synthetic method technology, applied in the synthesis field of trans-4-acetoxy-2-methyl-2-butene-1-aldehyde, can solve the problem of high reaction pressure requirements, low raw material utilization, The reaction requires a large pressure and other problems to achieve the effects of improving selectivity, reducing losses, and reducing production costs and process complexity.

Inactive Publication Date: 2016-09-28
FUJIAN FUERJIN BIOTECHNOLOGY CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although this patent solves the difficult problem of separation, the raw material utilization rate of this route is low, and the problem that the reaction also requires relatively high pressure still exists. Patent US4124619 reports that 1,4-butenediol diethyl ester is used as raw material to synthesize trans 4-acetoxy-2-methyl-2-buten-1-al, the route is as Figure 5 shown
[0005

Method used

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  • Synthetic method of trans-4-acetoxyl-2-methyl-2-butene-1-aldehyde

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Embodiment 1

[0031] Get 100 grams of 3,4-diacetoxy-1-butene, 0.1 grams of catalyst rhodium trichloride (rhodium content 39.5%) and 9.88 grams of triphenylphosphine into the autoclave, exhaust the air, Raise the temperature to 85°C, and then use the mixed gas of hydrogen and carbon monoxide with a molar ratio of 1:2 to increase the pressure of the reactor to 100 kg, and maintain this temperature. When the pressure of the reactor drops by about 3 kg and does not continue to drop, Start to cool down to room temperature, exhaust the gas, and carry out vacuum distillation of the reaction solution to obtain 85 grams of product, the content of the target product 3-formyl-1,2-butanediol diethyl ester is 91%, and the by-product formula 3 The content is 6%.

Embodiment 2

[0033] Get 100 grams of 3,4-diacetoxy-1-butene, 0.01 grams of catalyst tris(triphenylphosphine) carbonyl rhodium hydride (rhodium content 11.2%) and 0.55 grams of triphenylphosphine together for high pressure reaction Exhaust all the air in the kettle, heat up to 100°C, then use the mixed gas of hydrogen and carbon monoxide with a molar ratio of 1:1 to raise the pressure of the reactor to 85 kg, maintain this temperature, and when the pressure of the reactor drops by 3 kg When the left and right do not continue to decline, start to cool down to room temperature, exhaust the gas, and carry out vacuum distillation of the reaction solution to obtain 93 grams of product. The content of the target product 3-formyl-1,2-butanediol diethyl ester is 95.3 %, the content of by-product formula 3 is 1.8%.

Embodiment 3

[0035] Get 100 grams of 3,4-diacetoxy-1-butene, 0.05 grams of catalyst tris(triphenylphosphine)rhodium carbonyl hydride (rhodium content 11.2%) and 1.64 grams of triphenylphosphine together for high-pressure reaction Exhaust the air, raise the temperature to 95°C, and then use the mixed gas of hydrogen and carbon monoxide with a molar ratio of 2:1 to raise the pressure of the reactor to 90 kg, maintain this temperature, and when the pressure of the reactor drops by 3 kg When the left and right do not continue to decline, start to cool down to room temperature, exhaust the gas, and carry out vacuum distillation of the reaction solution to obtain 93 grams of product. The content of the target product 3-formyl-1,2-butanediol diethyl ester is 96.3 %, the content of by-product formula 3 is 0.8%.

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Abstract

The invention discloses a synthetic method of trans-4-acetoxyl-2-methyl-2-butene-1-aldehyde. The method comprises the steps that 3,4-diacetoxy-1-butene and synthetic gas are used as raw materials, a formylation reaction is carried out at the temperature of 85-100 DEG C and pressure of 85-100 kg under the effects of a rhodium catalyst and an additive, the synthetic gas is mixed gas of nitrogen and carbon monoxide, and 3-formoxyl-1,2-butanediol diethyl ester is prepared; the 3-formoxyl-1,2-butanediol diethyl ester is subjected to a decarboxylic reaction at the temperature of 85-120 DEG C through an acid catalyst, and the trans-4-acetoxyl-2-methyl-2-butene-1-aldehyde is obtained. By adding the additive in the formylation reaction and adjusting the mass ratio of the additive to rhodium in the rhodium catalyst, the formylation selectivity is greatly improved, and the formylation reaction pressure is lowered; no solvent is needed, the loss caused by solvent recycling can be lowered, the production cost and production difficulty are reduced, and the raw material utilization rate is improved.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a synthesis method of trans 4-acetoxy-2-methyl-2-butene-1-aldehyde. Background technique [0002] Vitamin A acetate belongs to the category of drugs, and its main function is to maintain the normal metabolism of animals and humans, maintain the stability and development of cell membranes, and maintain the normal functions of the reproductive system. And trans-4-acetoxy-2-methyl-2-buten-1-al is the key intermediate for the chemical synthesis of vitamin A acetate, and its research has never been interrupted, and the methods are not the same, Among them, there is a kind of method to synthesize the key intermediate with the ester compound of butenediol as the starting material. U.S. Patent No. 3,732,287 reports that 3,4-diacetoxy-1-butene is used as the raw material to synthesize 3-formyl-1 , 2-butanediol diethyl ester, the process is as figure 1 shown. But this paten...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/297
CPCC07B2200/09C07C67/293C07C67/297C07C69/145C07C69/16
Inventor 蓝晓春
Owner FUJIAN FUERJIN BIOTECHNOLOGY CO LTD
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