Method for chemical synthesis of vitamin K2

A chemical synthesis and vitamin technology, applied in organic chemistry, quinone oxide preparation, etc., can solve the problems of high equipment requirements, difficult separation, large amount of eluent and adsorbent, etc., and achieve equipment and energy consumption reduction, separation The treatment is simple and beneficial to the effect of environmental protection

Inactive Publication Date: 2012-02-15
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 1. What the reaction that 2-methyl-1,4-naphthoquinone is reduced into hydroquinone of this method adopts is common reducing agent reducing method, needs to use reducing agent KBH in a large amount 4 , the follow-up separation is difficult, the corresponding energy consumption is large, and the production cost is high
[0005] 2. The Fridel-Crafts alkylation reaction itself of this method is the process of constantly generating water, and the catalyst anhydrous zinc chloride, boron trifluoride ether, and cuprous bromide are sensitive to water and easily decompose in water. It will inevitably lead to the deactivation of part of the catalyst, resulting in waste of the catalyst, which in turn affects the yield of this step reaction, which is not good for production
Because the catalyst is sensitive to wate

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0029] A chemically synthesized vitamin K 2 The method, its specific method steps are as follows:

[0030] (1) Catalytic hydrogenation reduction reaction

[0031] With 2-methyl-1,4-naphthoquinone as raw material, Pd / C with a mass concentration of 5% as a catalyst, and isopropyl ether as a solvent, according to the molar amount of 2-methyl-1,4-naphthoquinone (mol): the volume (ml) of isopropyl ether: the ratio of the mass (g) of 5% Pd / C is the ratio of 1: 5000: 20, in the dry reflux reactor with stirring device, add 2 -Methyl-1,4-naphthoquinone and isopropyl ether and stir and mix evenly, then pass through nitrogen protection, and heat until the reaction liquid starts to reflux, and under the condition of maintaining reflux, switch nitrogen to hydrogen to the entire reactor Until the inside is filled with hydrogen, then under stirring conditions, add a Pd / C catalyst with a mass concentration of 5%, and continue to pass hydrogen to carry out the catalytic hydrogenation reducti...

Embodiment 2

[0040] A chemically synthesized vitamin K 2 The method, with embodiment 1, wherein:

[0041] In the (1) step, the molar weight (mol) of 2-methyl-1,4-naphthoquinone: the volume (ml) of isopropyl ether: the ratio of the mass (g) of the Pd / C of 5% is 1: 4000:15, the collected filtrate was distilled at a constant temperature of 70°C to recover the solvent isopropyl ether, and the distilled product was placed in a vacuum desiccator, and vacuum-dried at 95°C for 0.75 hours.

[0042] (in the 2nd step, the molar weight (mol) of geraniol: the molar weight (mol) of the 2-methyl-1,4-naphthalenediol that (1) step reaction makes: the volume of solvent isopropyl ether (ml): water-resistant Lewis acid catalyst (ie Sm(OTf) 3 ) in a molar (mol) ratio of 1:1:4000:0.05, the Fridel-Crafts alkylation reaction was carried out at a constant temperature of 40° C. for 6 hours. The ratio of reaction liquid: volume (ml) of distilled water was 1:0.5, and the ratio of organic layer: volume (ml) of dist...

Embodiment 3

[0046] A chemically synthesized vitamin K 2 The method, with embodiment 1, wherein:

[0047]In the (1) step, the molar weight (mol) of 2-methyl-1,4-naphthoquinone: the volume (ml) of isopropyl ether: the ratio of the mass (g) of the Pd / C of 5% is 1: 6000:25, the collected filtrate was distilled at a constant temperature of 71°C to recover the solvent isopropyl ether, and the distilled product was placed in a vacuum desiccator, and vacuum-dried at 100°C for 0.5 hours.

[0048] (in the 2nd step, the molar weight (mol) of geraniol: the molar weight (mol) of the 2-methyl-1,4-naphthalenediol that (1) step reaction makes: the volume of solvent isopropyl ether (ml): water-resistant Lewis acid catalyst (ie Sm(OTf) 3 ) in a molar (mol) ratio of 1:2:6000:0.2, the Fridel-Crafts alkylation reaction was carried out at a constant temperature of 40° C. for 3 hours. The ratio of reaction solution: volume (ml) of distilled water was 1:1, the ratio of organic layer: volume (ml) of distilled ...

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Abstract

The invention relates to a method for chemical synthesis of vitamin K2, and belongs to the technical field of organic synthesis. In the method, 2-methyl-1,4-naphthoquinone and geraniol are taken as raw materials, catalytic hydrogenation is firstly performed on 2-methyl-1,4-naphthoquinone for reducing 2-methyl-1,4-naphthoquinone into 2-methyl-1,4-hydronaphthoquinone, then Fridel-Crafts alkylation reaction is further performed with geraniol, and the product is finally obtained by oxidation reaction. The method has the characteristics of high product yield, high recycling rate of materials, low production cost, simplicity and convenience in production process and low energy consumption, and is conductive to environmental protection, convenient to popularize and apply and the like. The method can be widely used for industrialized large-scale production of vitamin K2, and vitamin K2 product synthesized by adopting the method can be widely used as the raw material for medicines, health-care products and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a chemically synthesized vitamin K 2 Methods. Background technique [0002] Vitamin K 2 It is a general term for a series of 2-methyl-1,4-naphthoquinone derivatives with biological activity of phylloquinone, and it is one of the indispensable important vitamins in the human body. Vitamin K 2 It can prevent liver cirrhosis from progressing to liver cancer. It is used to treat vitamin K deficiency hemorrhage, promote the formation of prothrombin, accelerate blood coagulation, and treat osteoporosis. It also has functions such as diuresis, strengthening the detoxification function of the liver, and lowering blood pressure. Great medical value. Therefore, synthetic vitamin K 2 become a major research topic. [0003] Existing chemically synthesized vitamin K 2 methods, such as the patent application number 20071006604.4 "a vitamin K 2 In the "synthetic method of a se...

Claims

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Application Information

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IPC IPC(8): C07C50/14C07C46/06
Inventor 罗自萍谭世语陈红梅张红晶杨灵莉杨海燕许其亮刘子林田婉洁徐迪
Owner CHONGQING UNIV
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