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A kind of vitamin B prepared from malic acid 6 Methods

A vitamin and malic acid technology, applied in the field of pharmaceutical biochemical industry, can solve the problems of long production cycle, heavy color of products, environmental pollution, etc., and achieve the effects of low cost, easy handling, and easy metabolism and decomposition

Active Publication Date: 2018-01-26
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the existing VB 6 The chemical synthesis method of the preparation process mostly uses 4-methyl-5-alkoxy-oxazole and 2-n-propyl-4,7-dihydro-1,3-dioxin as starting materials, after adding Synthesis and aromatization reaction etc. to prepare VB 6 , there are problems such as long production cycle, many three wastes produced, environmental pollution, and the product is heavily colored and difficult to decolorize

Method used

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  • A kind of vitamin B prepared from malic acid <sub>6</sub> Methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Vitamin B 6 (I) Preparation

[0041] Step (1): Preparation of 1H,4H-dihydrofuro[3,4-c]dihydrofuran-1,4-dione Ⅲ

[0042] Add 100 grams of toluene, 10 grams of water, 13.4 grams (0.1 mole) of D, L-malic acid, 0.85 grams of piperidine into a 500 ml four-neck flask equipped with stirring, a thermometer and a water separator, heat up to 50 ° C, drop Add 30 g of 30% aqueous formaldehyde solution, dropwise, and react at 50° C. for 5 hours. Add 3.0 grams of p-toluenesulfonic acid, reflux with azeotropic water until the water is completely separated, cool to 20 ° C, filter to remove piperidine-p-toluenesulfonate, wash the filter cake twice with toluene (using 20 grams of toluene ), reclaiming toluene to obtain 14.1 grams of oil compound III, with a purity of 98.6% (GC), and a pure yield of 99.3%, which was directly used in the next step.

[0043] Step (2): Vitamin B 6 (I) Preparation

[0044] Add 80 grams of tetrahydrofuran, 8.3 grams (0.11 moles) of nitroethane,...

Embodiment 2

[0045] Example 2: Vitamin B 6 (I) Preparation

[0046] Step (1): Preparation of 1H,4H-dihydrofuro[3,4-c]dihydrofuran-1,4-dione Ⅲ

[0047] Add 100 grams of toluene, 15 grams of water, 13.4 grams (0.1 moles) of D, L-malic acid, 0.85 grams of piperidine into a 500 ml four-neck flask equipped with stirring, a thermometer and a water separator, heat up to 50 ° C, drop Add 30 g of 30% aqueous formaldehyde solution, dropwise, and react at 50° C. for 5 hours. Add 1.5 grams of 98% concentrated sulfuric acid, reflux with azeotropic water until the water is completely separated, cool to 20°C, filter to remove the piperidine sulfate salt, wash the filter cake twice with toluene (using 20 grams of toluene), and recycle the toluene to obtain an oily substance Compound III was 13.8 g, with a purity of 98.5% (GC), and a pure yield of 97.1%, which was directly used in the next step.

[0048] Step (2): Vitamin B 6 (I) Preparation

[0049] Add 80 grams of tetrahydrofuran, 8.3 grams (0.11 mo...

Embodiment 3

[0050] Example 3: Vitamin B 6 (I) Preparation

[0051] Step (1): Preparation of 1H,4H-dihydrofuro[3,4-c]dihydrofuran-1,4-dione Ⅲ

[0052] Add 120 grams of toluene, 10 grams of water, 13.4 grams (0.1 moles) of L-malic acid, and 1.5 grams of tri-n-butylamine into a 500 milliliter four-neck flask equipped with stirring, a thermometer and a water separator. Add 30 grams of 30% formaldehyde aqueous solution, drop it, and react at 40-45° C. for 5 hours. Add 3.5 grams of p-toluenesulfonic acid, reflux with azeotropic water until the water is completely separated, cool to 20 ° C, filter to remove tri-n-butylamine p-toluenesulfonate, wash the filter cake twice with toluene (using 20 grams toluene), reclaiming toluene to obtain 13.9 grams of oil compound III, with a purity of 98.8% (GC), and a pure yield of 98.1%, which was directly used in the next step.

[0053] Step (2): Vitamin B 6 (I) Preparation

[0054] Add 80 grams of tetrahydrofuran, 8.3 grams (0.11 moles) of nitroethane, ...

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Abstract

The present invention relates to a method of using malic acid to prepare vitamin B6. The method comprises: using malic acid as a starting material; carrying out a hydroxymethylation reaction on the malic acid and formaldehyde in the presence of a basic catalyst to generate 2-hydroxy-2,3-dimethylol butanedioic acid; performing acid catalysis and lactonization for ring-forming to obtain 1H,4H-dihydrofuro[3,4-c]dihydrofuran-1,4-diketone (III); under base catalysis, condensing the obtained compound III and nitro ethane to obtain a compound IV; reducing the compound IV by using sodium borohydride or potassium borohydride to obtain a compound V; performing catalytic hydrogenation on the compound V to obtain a compound VI; and performing hydrolysis and ring-forming on the compound VI in an ethanol-hydrochloric acid system to obtain vitamin B6. According to the method of the present invention, the use of the 4-methyl-5-alkoxyl oxazole intermediate that is expensive and of which the preparation process causes pollution is avoid; the raw materials are inexpensive and readily available; the process is short; and the cost is low. The method in the present invention is simple in operation, less in wastewater discharge, highly environmentally friendly, and suitable for green industrial production of VB6.

Description

technical field [0001] The invention relates to a method for preparing vitamin B from malic acid 6 The method belongs to the field of pharmaceutical biochemical technology. Background technique [0002] Vitamin B 6 , chemical name: 5-hydroxy-6-methyl-3,4-pyridinedimethanol hydrochloride or 3-hydroxy-2-methyl-4,5-dimethylolpyridine hydrochloride, referred to as VB 6 , is one of the essential vitamins for the human body. It plays a key role in the growth of animals, so it is widely used in the fields of medicine, food, feed additives and cosmetics industries. Vitamin B 6 In nature, there are three forms of pyridoxine, pyridoxal and pyridoxamine. Under certain conditions, the three can be transformed into each other in the body. The industrial synthesis is generally pyridoxine hydrochloride, that is, 2-methyl -3-hydroxy-4,5-dimethylolpyridine hydrochloride. [0003] At present, the industry usually uses chemical synthesis to produce vitamin B 6 , such as US Patent US32277...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/67
CPCC07D213/67
Inventor 戚聿新吕强三鞠立柱李新发
Owner XINFA PHARMA
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