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Preparation method of intermediate for synthesizing anise camphor

A kind of technology of anethole and intermediates, applied in the field of production process of organic spices, can solve the problems of high cost, low conversion rate or yield, and conversion rate of only 71%

Active Publication Date: 2014-07-30
SUQIAN COSMOS CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0017] This route raw material is easy to get, and the yield of the first step and the third step is all higher, and the second step reduction step is a key step, and this step prepares 1-( When using 4-methoxyphenyl) propanol, because the carbonyl is located at the benzyl position, and there is a strong donor group at the para position, the side reactions are greatly increased
Although the catalyst that adopts ruthenium-loaded ligand in the prior art can catalytically reduce p-methoxypropiophenone to generate 1-(4-methoxyphenyl)propanol, the conversion rate is only 71%, and the catalyst used is very expensive
In addition, ammonium formate is used as a hydrogen source to reduce this similar substrate, but the disadvantage is that the reaction requires a large amount of ammonium formate, and produces a large amount of waste ammonia, which brings environmental pollution
[0018] From the prior art analysis, it can be seen that there are many problems in the existing synthetic anethole, especially trans-anethole technology, such as raw materials are not easy to obtain or expensive, the conversion rate or yield is not high, and the reaction reagents or reaction conditions are harsh. , side reactions and by-products increase and environmental pollution caused by "three wastes"

Method used

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  • Preparation method of intermediate for synthesizing anise camphor
  • Preparation method of intermediate for synthesizing anise camphor
  • Preparation method of intermediate for synthesizing anise camphor

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preparation example Construction

[0027] According to the present invention, a kind of preparation method of the intermediate of synthetic anethole is provided, and this preparation method comprises following 3 steps:

[0028] Step 1. Add aluminum-nickel alloy in batches to the alkaline aqueous solution, react the aluminum in the alloy completely, pour off the supernatant liquid, add water to wash until neutral, pour off the upper water layer, add solvent and wash until the water content is less than 2% to prepare a Raney nickel catalyst and store it under a solvent cover.

[0029] According to the present invention, at first synthesize Raney nickel catalyst, preferably W-2 type Raney nickel, can adopt existing preparation W-2 type Raney nickel preparation method to prepare, but must control washing water to neutrality during washing, finally use The solvent is washed until the water content is less than 2%, preferably less than 1.5%, more preferably less than 1%, which is particularly important for the subseq...

Embodiment 1

[0053] Embodiment 1: the preparation of Raney nickel catalyst

[0054] Into a 4L four-neck flask, throw 380g of sodium hydroxide dissolved in 1.5L of water, stir, and cool to 10°C under an ice bath. Under stirring, add 300g of aluminum-nickel alloy in batches to the liquid caustic soda in small amounts, the speed of adding should be controlled so that the temperature of the solution does not exceed 25°C (under ice bath). When all the addition was complete, the stirring was stopped, the ice bath was removed, and the reaction solution was allowed to rise to room temperature. When the hydrogen generation rate is slow, it can be heated slowly on a boiling water bath (avoid heating up too fast, in case there are too many bubbles and the reaction solution overflows), until the bubbles slow down again. Then let it stand still, let the nickel powder sink, pour off the supernatant, add water to the original volume, stir the solution to suspend the nickel powder, let it stand again to ...

Embodiment 2

[0055] Example 2: 1-(4-methoxyphenyl)propanol

[0056] In a 1L autoclave, add 300g of p-methoxypropiophenone and 300g of methanol, heat to 60°C, dissolve the p-methoxypropiophenone solid under stirring, then add 30g of Raney nickel prepared in Example 1, and use nitrogen gas After replacing three times, hydrogen gas was introduced, and the temperature was raised slowly. The temperature was controlled at 80°C, and the hydrogen pressure was controlled at 2.0 MPa. After 5 hours of hydrogenation reaction, the reaction did not absorb hydrogen, and the hydrogenation reaction was stopped.

[0057] The temperature was lowered to room temperature, the catalyst was recovered by filtration, and the content of the filtrate was detected by gas chromatography to be 93%. Methanol was recovered by atmospheric distillation, and 275 g of 1-(4-methoxyphenyl)propanol (GC content: 98.5%) was obtained by vacuum distillation at the bottom, with a yield of 90.6%.

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Abstract

The invention discloses organic spice anise camphor and a production process of an intermediate of the anise camphor. The production process mainly comprises the following step: performing catalytic hydrogenation on methoxypropiophenone to generate 1-(4-methoxyphenyl) propanol. Cheap raney nickel is taken as a catalyst for the hydrogenation reaction in the production process, and consequently, the production cost is greatly reduced and the reaction time is shortened, and the product purity is also guaranteed; the product yield is more than 90%.

Description

technical field [0001] The invention relates to a production process of organic spices, in particular to a new production process of anethole as an organic spice; it belongs to the technical field of chemical industry. Background technique [0002] Anethole, also known as anethole, is called anethole in English, and its chemical name is 1-(4-methoxyphenyl)propene. There are two isomers of cis and trans, and the CAS of the mixture of cis and trans anethole The number is 104-46-1, the CAS number of trans-anethole is 4180-23-8, and the structural formula is: [0003] [0004] The use of trans-anethol as a condiment has been confirmed as "generally recognized as safe" (GRAS) by the US Food and Drug Administration (FDA) and the American Flavor and Extract Manufacturers Association (FEMA). The industrial production of anethole is mainly obtained by isolation of essential oil, separation of crude sulfate turpentine (CST) and chemical synthesis. [0005] Among the chemical synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/26C07C43/23C07C41/18
CPCC07C41/18C07C41/26C07C43/23C07C43/215Y02P20/584
Inventor 陈和平葛建军刘建生沈宏宇许治永
Owner SUQIAN COSMOS CHEM
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