Green preparation method of menadione sodium bisulfite

A technology of menadione sodium bisulfite and sodium bisulfite, which is applied in the field of green preparation of menadione sodium bisulfite, can solve the problem of high prices of 2-methylnaphthalene and m-chloroperoxybenzoic acid, and sulfurous acid Menadione hydrogen sodium has poor reaction selectivity and no industrial application value, etc., and achieves the effects of easy scale-up and control, less side reactions, high specificity and selectivity

Active Publication Date: 2021-07-30
XINFA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Although the above synthetic route 2 avoids the heavy metal pollution caused by the oxidation of chromium ions, the price of 2-methylnaphthalene and m-chloroperoxybenzoic acid is high and the yield is low, resulting in high cost and no industrial application value
[0011] In summary, in the prior art, the preparation method of sodium bisulfite menadione has disadvantages such as poor reaction selectivity, many side reactions, low product purity and yield, poor environmental protection, and high cost. Therefore, a complete, green and environmentally friendly The synthetic route of menadione sodium bisulfite, easy to realize, low cost, high reaction selectivity and yield and purity is of great significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: the preparation of 1-naphthol (Ⅲ)

[0065] To a 500-milliliter four-neck flask connected with a stirring, thermometer, reflux condenser, air duct and 30 wt% sodium hydroxide aqueous solution absorption device, add 300 grams of 1,2-dichloroethane, 73.0 grams (0.5 moles) of 3, 4-Dihydro-1(2H)-naphthalenone (II), heat, keep at 40-45°C, slowly pass in 39.0 g (0.55 moles) of chlorine gas, and pass in about 2-3 hours, then 45- Stir and react at 50°C for 3 hours, cool to 20-25°C, add 60.0 g (0.6 moles) of 40wt% sodium hydroxide aqueous solution, stir and react at 30-35°C for 2 hours, cool to 20-25°C, acidify the pH of the system with 30wt% hydrochloric acid The value is 3.0-4.0, separate layers, the water layer is extracted 3 times with 1,2-dichloroethane, 50 grams each time, the organic phases are combined, the solvent is recovered by distillation, and dried to obtain 69.5 grams of 1-naphthol (Ⅲ), Yield 96.5%, gas phase purity 99.8%.

Embodiment 2

[0066] Embodiment 2: the preparation of 1-naphthol (Ⅲ)

[0067] To a 500-milliliter four-neck flask connected with a stirring, thermometer, reflux condenser, air duct and 30 wt% sodium hydroxide aqueous solution absorption device, add 300 grams of 1,2-dichloroethane, 73.0 grams (0.5 moles) of 3, 4-Dihydro-1(2H)-naphthalenone (II), 62.5g (0.6mol) 35wt% hydrochloric acid, add 61.5g (0.55mol) 30wt% hydrogen peroxide dropwise at 35-40°C for about 3-4 hours After the dropwise addition is completed, stir and react at 40-45°C for 4 hours, cool to 20-25°C, add 60.0 g (0.6 moles) of 40wt% sodium hydroxide aqueous solution, stir and react at 30-35°C for 2 hours, and cool to 20-25°C , 30wt% hydrochloric acid acidification system pH value is 3.0-4.0, layering, the aqueous layer is extracted 3 times with 1,2-dichloroethane, 50 grams each time, the organic phase is combined, the solvent is recovered by distillation, and dried to obtain 69.1 grams of 1 -Naphthol (Ⅲ), yield 96.0%, gas phase ...

Embodiment 3

[0068] Embodiment 3: the preparation of 1-naphthol (Ⅲ)

[0069] To a 500-milliliter four-neck flask connected with a stirring, thermometer, reflux condenser, air duct and 30 wt% sodium hydroxide aqueous solution absorption device, add 300 grams of dichloromethane, 73.0 grams (0.5 moles) of 3,4-dihydro- 1(2H)-Naphthone (II), 111g (0.55mol) 40wt% hydrobromic acid, add 56.0g (0.5mol) 30wt% hydrogen peroxide dropwise between 25-30°C, and dropwise add in about 3-4 hours , after this 25-30 ℃ stirring reaction 2 hours; Add 60.0 grams (0.6 mole) 40wt% sodium hydroxide aqueous solution, 25-30 ℃ stirring reaction 2 hours; 30wt% hydrochloric acid acidification system pH value is 3.0-4.0, layering, water The layer was extracted 3 times with dichloromethane, 50 g each time, the organic phases were combined, the solvent was recovered by distillation, and dried to obtain 71.0 g of 1-naphthol (III), with a yield of 98.6% and a gas phase purity of 99.9%.

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Abstract

The invention provides a preparation method of menadione sodium bisulfite. The method comprises the following steps of: by using cheap and easily available 3, 4-dihydro-1 (2H)-naphthalenone as a raw material, carrying out halogenation-elimination to obtain 1-naphthol; carrying out methylation reaction to generate 2-methyl-1-naphthol; carrying out air oxidation on the 2-methyl-1-naphthol to obtain 2-methyl-1, 4-naphthoquinone; and carrying out addition reaction on the 2-methyl-1, 4-naphthoquinone and sodium hydrogen sulfite so as to obtain the menadione sodium bisulfite. The method has the advantages of cheap and easily available raw materials, low cost, safe, simple and convenient process operation, less process wastewater generation, green and environment-friendly performance, high stability of raw materials and intermediate products, high reaction activity and selectivity, easy realization of reaction conditions, few side reactions and high product purity and yield, and can facilitate the industrial production of the menadione sodium bisulfite.

Description

technical field [0001] The invention relates to a green preparation method of menadione sodium bisulfite, which belongs to the technical field of organic synthesis. Background technique [0002] Menadione sodium bisulfite (I), also known as vitamin K3, the English name is Menadione sodium bisulfite, the CAS number is 130-37-0, the chemical name is 2-methyl-1,4-naphthoquinone sodium bisulfite , the molecular formula is C 11 h 8 o 2 NaHSO 3· 3H 2 O, relative molecular weight 330.29, white or light yellow crystalline powder, odorless or slightly peculiar odor, easily soluble in water, slightly soluble in ethanol, isopropanol and acetone, not volatile, easy to absorb moisture, decomposes when exposed to light, no Smell, slightly bitter. Menadione sodium bisulfite is an indispensable nutrient element for the life activities of livestock and poultry, and is an essential component of feed additives; its main function is to participate in the synthesis of thrombin in the anima...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/32C07C309/25
CPCC07C37/00C07C46/08C07C303/32C07C39/14C07C50/10C07C309/25Y02A40/70
Inventor 江枭南周立山戚聿新
Owner XINFA PHARMA
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