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Continuous flow microchannel synthesis process of flavonoid compounds

A flavonoid compound and flow synthesis technology, applied in chemical/physical processes, chemical/physical/physical chemical processes, chemical/physical/physical chemical reactors, etc., can solve the problem of unfriendly environment, hazards to operators, and long preparation time and other problems, to achieve the effect of improving the conversion rate, broad application prospects, and shortening the preparation time

Pending Publication Date: 2021-06-18
宜宾西华大学研究院 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the irritating solvent used in the production process of this method will cause great harm to the operator and is not friendly enough to the environment
Moreover, the preparation time of the process is long, time-consuming and energy-consuming

Method used

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  • Continuous flow microchannel synthesis process of flavonoid compounds
  • Continuous flow microchannel synthesis process of flavonoid compounds
  • Continuous flow microchannel synthesis process of flavonoid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]Embodiment 1, the continuous flow microchannel synthesis technique of diosmin

[0044] Using a continuous flow microchannel reactor, according to figure 1 The process flow shown prepares diosmin, and the reaction scheme is as follows figure 2 shown. The specific operation is as follows:

[0045] Step 1: Reaction liquid pretreatment: Mix hesperidin, iodine simple substance, and solvent pyridine evenly, and stir at 10°C under normal pressure for 30 minutes to obtain a reaction liquid; wherein, the raw material concentration (hesperidin / pyridine, mass-volume ratio) is 50 mg / ml, the raw material molar ratio (iodine / hesperidin) is 1.5:1.

[0046] Step 2: Feed the reaction solution obtained after stirring in step 1 to the continuous flow microreactor for reaction. The reaction conditions of the continuous flow microchannel are: volume flow rate of reaction solution 1.0mL / min, pressure 10Bar, reaction temperature 170°C, reaction time 2.7 min.

[0047] Step 3: post-proces...

Embodiment 2

[0051] Embodiment 2, the continuous flow microchannel synthetic technique of flavonoid compound

[0052] Using a continuous flow microchannel reactor, according to figure 1 The process flow shown prepares diosmin, and the reaction scheme is as follows:

[0053]

[0054] The structure of the compound shown in Formula A is as shown in Table 1, m, n, R in the compound shown in Formula B 1 , R 2 , R 3 With m, n, R in the compound shown in formula A 1 , R 2 , R 3 same.

[0055] The specific operation is as follows:

[0056] Step 1: Reaction solution pretreatment: Mix the compound shown in formula B, iodine element, and solvent pyridine evenly, and stir at 10°C under normal pressure for 30 minutes to obtain the reaction solution; wherein, the raw material concentration (hesperidin / pyridine, mass volume ratio) The molar ratio of raw materials (iodine / hesperidin) is 1.5:1.

[0057] Step 2: Feed the reaction solution obtained after stirring in step 1 to the continuous flow ...

experiment example 1

[0064] Experimental example 1. Screening experiment of continuous flow microchannel synthesis process under different conditions under normal pressure

[0065] 1. Experimental method

[0066] (1) Screening experiments at different reaction temperatures:

[0067] Mix hesperidin, elemental iodine, and solvent pyridine evenly to obtain a reaction solution; wherein the concentration of raw materials (hesperidin / pyridine, mass-to-volume ratio) is 50 mg / ml, and the molar ratio of raw materials (elemental iodine / hesperidin) is 1.1: 1;

[0068] The reaction solution was fed to the continuous flow microreactor for reaction, and the continuous flow microchannel reaction conditions were (see Table 2): reaction solution volume flow rate 1.2mL / min, normal pressure, reaction temperature 60-130°C, reaction time 135s.

[0069] Then follow the same method as Step 3 of Example 1 for post-processing to obtain the target product diosmin. The yield of diosmin under each condition is shown in Ta...

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Abstract

The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the field of synthesis technology, and in particular relates to a continuous flow microchannel synthesis technology of flavonoids. Background technique [0002] Flavonoids are active ingredients of many Chinese herbal medicines and have many important physiological and biochemical effects on mammalian and other types of cells due to their unique chemical structures. With the in-depth study of clinical drugs and the continuous improvement of national health concepts, the consumption demand of modern Chinese medicine is also increasing, and the market prospect of flavonoids is very promising. At present, flavonoids are mainly obtained by extraction and isolation from plants, total synthesis and semi-synthesis. It is an important method to prepare flavonoids by dehydrogenating flavonoids as raw materials to synthesize corresponding flavonoids, including iododehydrogenation, bromodehydrogenation, hydrogen peroxide dehydrogenation ...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07H17/07C07H1/00C07D407/04C07D311/36C07D493/14B01J19/00
CPCC07D311/30C07H17/07C07H1/00C07D407/04C07D311/36C07D493/14B01J19/0093
Inventor 钱珊王周玉宋巧朱章燕梁烽罗宗源陈建军
Owner 宜宾西华大学研究院
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