Preparation method of glassine

Abstract

The invention discloses a preparation method of a glassine. The preparation method comprises the following steps: a) preparing raw materials; step b) condensation reaction; c) reduction reaction; step d) electrophilic substitution reaction; step e) crystallization and purification: step a) raw material preparation. According to the present invention, the electrophilic substitution reaction can be performed under the mild condition without the extreme reaction conditions such as the high temperature or the high pressure, such that the reaction is easily controlled, and the monomer source used by the electrophilic substitution reaction is generally convenient compared with the other types of the organic reactions; the xylose subjected to the condensation reaction is beneficial to improving the permeability of the glassy pigment, so that the glassy pigment can be deeply permeated into the skin, the energy consumption and waste emission in the production process can be reduced, and meanwhile, the treatment is performed in a heating and pressurizing manner in the reaction process, so that incomplete reaction or by-product generation can be avoided, and the production cost is reduced. And the final crystallization purification can improve the purity of the product.

Description

Technical Field

[0001] The invention relates to the technical field of boson preparation, in particular to a method for preparing boson. Background Art

[0002] Bosera is a xylose derivative with anti-aging activity. It is derived from xylose, which is found in large quantities in beech trees. Bosera can promote the synthesis of collagen, thereby enhancing skin elasticity, reducing wrinkles, improving skin texture, and activating the synthesis of glycosaminoglycans (GAGs): Based on the principles of bionics, bosera can activate the synthesis of glycosaminoglycans, which are an important component of the skin's extracellular matrix (ECM). They can absorb moisture, prevent skin moisture loss, and keep the skin hydrated. At the same time, the molecular structure of glycosaminoglycans helps to enhance the elasticity of the matrix network structure, improve the firmness of cells, and make the skin more elastic.

[0003] For example, the patent number published on the China Patent Network is: 202310496185.9, and the patent name is: A method for preparing high-purity boson, the method comprising the following steps: D-xylose and acetylacetone are condensed under alkaline conditions to form a ketone intermediate; the ketone intermediate described in step 1 is acylated to obtain a triacyl ketone intermediate; a boron reducing agent is used to selectively reduce the triacyl ketone intermediate to obtain a crude triacyl alcohol intermediate, which is a triacyl boson intermediate; the crude triacyl boson intermediate is extracted using a non-water-soluble organic solvent and water, and the organic phase is washed with a hydroxyl-containing compound selected from a polyhydroxy compound and / or an o-hydroxy acid or an aqueous solution thereof to obtain a deboronized and desalted triacyl boson intermediate; organic impurities are removed by crystallization to obtain a desalted and deboronized pure triacyl boson intermediate; the acylation protecting group is removed and amide impurities are removed to obtain high-purity boson.

[0004] However, the existing bosogenin preparation process requires specific temperature and pH conditions to ensure the efficient reaction. These conditions may be harsh and require precise control, otherwise the reaction may be incomplete or by-products may be produced. Since the condensation reduction reaction produces a variety of by-products, the purity of the product may be affected, which requires the use of efficient purification technology to ensure the quality and purity of the product.

[0005] Therefore, it is necessary to design and modify the preparation method of boson. Summary of the invention

[0006] In order to solve the problems raised in the above background technology, the purpose of the present invention is to provide a method for preparing bosone, which has the advantage of improving the reaction preparation effect and solving the problems that lead to incomplete reaction or generation of by-products. Since the condensation reduction reaction produces a variety of by-products, the purity of the product may be affected, which requires the use of efficient purification technology to ensure the quality and purity of the product.

[0007] To achieve the above object, the present invention provides the following technical solution: a method for preparing boson, comprising step a) raw material preparation; step b) condensation reaction; step c) reduction reaction; step d) electrophilic substitution reaction; step e) crystallization purification: Step a) Raw material preparation: using a large amount of xylose extracted from beech as the main raw material; Step b) condensation reaction: xylose and acetylacetone liquid are added to an alkaline aqueous solution to cause a Knoevenagel condensation reaction between the two to generate 1-C-(beta-D-xylopyranosyl)-acetone; Step c) Reduction reaction: Reduction reaction is then carried out with sodium borohydride to reduce the ketone carbonyl group in the product; Step d) Electrophilic substitution reaction: electrophilic substitution reaction is carried out on the keto carbonyl group. Electrophilic substitution reaction is a commonly used organic synthesis reaction. By electrophilically substituting a hydrogen atom of the keto carbonyl group to form the structure of bosone, 1-C-(beta-D-xylopyranosyl)-2-hydroxy-propane, i.e. bosone, can be obtained; Step e) Crystallization purification: The synthesized boson usually exists in the form of a solvent and needs to be crystallized and purified to improve its purity.

[0008] As a preferred embodiment of the present invention, in step a), raw materials are prepared and processed into xylose powder by grinding and pulverizing, and xylose powder with larger particle size is removed by screening.

[0009] As a preferred embodiment of the present invention, the step b) condensation reaction: continuously heating the mixed alkaline aqueous solution of xylose and acetylacetone liquid by microwave heating, wherein the alkaline aqueous solution is a sodium hydroxide solution.

[0010] As a preferred embodiment of the present invention, in the reduction reaction of step c), sodium borohydride and 1-C-(beta-D-xylopyranosyl)-acetone are added to a reactor, and a mixing reaction is carried out by continuous stirring and pressurizing. The pressurized pressure is greater than 2 MPa and the temperature is higher than 60 degrees. At the same time, after the reaction is completed, the reaction mixed gas is first extracted and processed by ventilation equipment.

[0011] As a preferred embodiment of the present invention, in step d) the electrophilic substitution reaction, water is used as the nucleophilic reagent, and after the treatment, the reaction is heated in a water bath at a temperature between 30-60 degrees.

[0012] As a preferred method of the present invention, the step e) is crystallization purification, adding the bosogenin solution to be purified into an appropriate amount of acetone solution, and stirring or heating to dissolve until it is completely dissolved, using appropriate filtering equipment to pass the solution through a filter to filter out solid particles or suspended matter to obtain a relatively pure solution, introducing enzyme crystals, and under the action of an inducer, the solute in the solution begins to crystallize and is wrapped around the surface of the enzyme crystals. During the crystallization process, the concentration of the solution will gradually increase, causing the substance to gradually transform into crystals.

[0013] As a preferred embodiment of the present invention, in step e) crystallization purification, the crystals are centrifuged to separate the solution, the crystals are washed with ethanol for multiple times to remove residual impurities, and the washed crystals are dried at low temperature to completely remove moisture.

[0014] As a preferred embodiment of the present invention, in step e) crystallization purification, the purity of bosphenic acid crystals can be determined by measuring the melting point of the bosphenic acid crystals. When the purity of the crystals is lower than the required level, the crystals can be further purified by repeated crystallization.

[0015] Compared with the prior art, the present invention has the following beneficial effects: 1. The present invention can be carried out under mild conditions by subjecting the ketone carbonyl to electrophilic substitution reaction, and does not require extreme reaction conditions such as high temperature or high pressure, which makes the reaction easier to control and reduces the risk of the reaction. At the same time, compared with other types of organic reactions, the source of monomers used in the electrophilic substitution reaction is usually more convenient, and the xylose in the condensation reaction helps to improve the permeability of bosone, allowing it to penetrate deeper into the skin. It is a relatively environmentally friendly and sustainable synthesis method that can reduce energy consumption and waste emissions in the production process. At the same time, the treatment by heating and pressurizing during the reaction process can avoid incomplete reaction or the generation of by-products, and the final crystallization purification can improve the purity of the product.

[0016] 2. The present invention can form crystal seeds by adding enzyme crystals during the crystallization process, thereby improving the crystallization efficiency of the phosphotin reaction. At the same time, the enzyme crystals usually undergo a special production and preservation process to maintain the high activity of the enzyme. The enzyme crystals are usually made by fermenting natural plants without adding any chemical ingredients, which can avoid reaction with phosphotin.

[0017] 3. The present invention can effectively guide the growth of botoxime crystals on its surface by setting enzyme crystals, thereby forming crystals more quickly. At the same time, the size and shape of botoxime crystals can be more accurately controlled to form crystals faster, thereby shortening the production cycle and reducing production costs. DETAILED DESCRIPTION

[0018] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0019] The present invention provides a method for preparing boson, comprising the steps of a) raw material preparation; b) condensation reaction; c) reduction reaction; d) electrophilic substitution reaction; and e) crystallization purification: Step a) Raw material preparation: using a large amount of xylose extracted from beech as the main raw material; Step b) condensation reaction: xylose and acetylacetone liquid are added to an alkaline aqueous solution to cause a Knoevenagel condensation reaction between the two to generate 1-C-(beta-D-xylopyranosyl)-acetone; Step c) Reduction reaction: Reduction reaction is then carried out with sodium borohydride to reduce the ketone carbonyl group in the product; Step d) Electrophilic substitution reaction: electrophilic substitution reaction is carried out on the keto carbonyl group. Electrophilic substitution reaction is a commonly used organic synthesis reaction. By electrophilically substituting a hydrogen atom of the keto carbonyl group to form the structure of bosone, 1-C-(beta-D-xylopyranosyl)-2-hydroxy-propane, i.e. bosone, can be obtained; Step e) Crystallization purification: The synthesized boson usually exists in the form of a solvent and needs to be crystallized and purified to improve its purity.

[0020] As a technical optimization solution of the present invention, the xylose powder is processed into xylose powder by grinding and crushing, and the xylose powder with larger particle size is removed by screening.

[0021] As a technical optimization solution of the present invention, the mixed alkaline aqueous solution of xylose and acetylacetone liquid is continuously heated by microwave heating, and the alkaline aqueous solution is a sodium hydroxide solution.

[0022] As a technical optimization scheme of the present invention, sodium borohydride and 1-C-(beta-D-xylopyranosyl)-acetone are added into a reactor, and a mixed reaction is carried out by continuous stirring and pressurization. The pressurization pressure is greater than 2MPa and the temperature is higher than 60 degrees. At the same time, after the reaction is completed, the reaction mixed gas is first extracted and processed by ventilation equipment.

[0023] As a technical optimization solution of the present invention, water is used as a nucleophilic reagent and heated in a water bath after the treatment, and the heating temperature is between 30-60 degrees.

[0024] As a technical optimization scheme of the present invention, the bosogenin solution to be purified is added to an appropriate amount of acetone solution and stirred or heated to dissolve until it is completely dissolved. The solution is passed through a filter using appropriate filtering equipment to filter out solid particles or suspended matter to obtain a relatively pure solution. The enzyme crystals are introduced. Under the action of the inducer, the solute in the solution begins to crystallize and is wrapped around the surface of the enzyme crystals. During the crystallization process, the concentration of the solution will gradually increase, causing the substance to gradually transform into crystals.

[0025] As a technical optimization scheme of the present invention, the crystals are centrifuged and precipitated by a centrifuge to separate the solution, and the crystals are washed with ethanol for multiple times to remove residual impurities, and the washed crystals are dried at a low temperature to completely remove moisture.

[0026] As a technical optimization scheme of the present invention, the purity of the boson crystals can be determined by measuring the melting point thereof. When the purity of the crystals is lower than the required value, they can be further purified by repeated crystallization.

[0027] The working principle and use process of the present invention are as follows: a large amount of xylose extracted from beech is used as a main raw material, xylose and acetylacetone liquid are added into an alkaline aqueous solution, and the two undergo a Knoevenagel condensation reaction to generate 1-C-(beta-D-xylopyranosyl)-acetone, and then a reduction reaction is performed with sodium borohydride to reduce the ketone carbonyl in the product, and the ketone carbonyl is subjected to an electrophilic substitution reaction. The electrophilic substitution reaction is a commonly used organic synthesis reaction. By electrophilically substituting a hydrogen atom of the ketone carbonyl to form a bosone structure, 1-C-(beta-D-xylopyranosyl)-2-hydroxy-propane, i.e. bosone, can be obtained. The synthesized bosone usually exists in the form of a solvent and needs to be crystallized and purified to improve the purity.

[0028] In summary: the preparation method of bosone, through the electrophilic substitution reaction of the ketone carbonyl group, can be carried out under mild conditions and does not require extreme reaction conditions such as high temperature or high pressure, which makes the reaction easier to control and reduces the risk of the reaction. At the same time, compared with other types of organic reactions, the source of monomers used in the electrophilic substitution reaction is usually more convenient, and the xylose from the condensation reaction helps to improve the permeability of bosone, allowing it to penetrate deeper into the skin. It is a relatively environmentally friendly and sustainable synthesis method that can reduce energy consumption and waste emissions in the production process. At the same time, the reaction is treated by heating and pressurizing to avoid incomplete reaction or the production of by-products, and the final crystallization purification can improve the purity of the product.

[0029] It should be noted that, in this article, relational terms such as first and second, etc. are only used to distinguish one entity or operation from another entity or operation, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Moreover, the terms "include", "comprise" or any other variants thereof are intended to cover non-exclusive inclusion, so that a process, method, article or device including a series of elements includes not only those elements, but also other elements not explicitly listed, or also includes elements inherent to such process, method, article or device.

[0030] Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions and variations may be made to the embodiments without departing from the principles and spirit of the present invention, and that the scope of the present invention is defined by the appended claims and their equivalents.

Claims

1. A method for preparing boson, characterized in that: The method comprises the steps of a) raw material preparation; b) condensation reaction; c) reduction reaction; d) electrophilic substitution reaction; and e) crystallization purification. Step a) Raw material preparation: using a large amount of xylose extracted from beech as the main raw material; Step b) condensation reaction: xylose and acetylacetone liquid are added to an alkaline aqueous solution to cause a Knoevenagel condensation reaction between the two to generate 1-C-(beta-D-xylopyranosyl)-acetone; Step c) Reduction reaction: Reduction reaction is then carried out with sodium borohydride to reduce the ketone carbonyl group in the product; Step d) Electrophilic substitution reaction: electrophilic substitution reaction is carried out on the keto carbonyl group. Electrophilic substitution reaction is a commonly used organic synthesis reaction. By electrophilically substituting a hydrogen atom of the keto carbonyl group to form the structure of bosone, 1-C-(beta-D-xylopyranosyl)-2-hydroxy-propane, i.e. bosone, can be obtained; Step e) Crystallization purification: The synthesized boson usually exists in the form of a solvent and needs to be crystallized and purified to improve its purity.

2. The method for preparing boson according to claim 1, characterized in that: In the step a), raw materials are prepared and processed into xylose powder by grinding and crushing, and xylose powder with larger particle size is removed by screening.

3. The method for preparing boson according to claim 1, characterized in that: The step b) condensation reaction: continuously heating the mixed alkaline aqueous solution of xylose and acetylacetone liquid by microwave heating, wherein the alkaline aqueous solution is a sodium hydroxide solution.

4. The method for preparing boson according to claim 1, characterized in that: In the step c) reduction reaction, sodium borohydride and 1-C-(beta-D-xylopyranosyl)-acetone are added to a reactor, and a mixed reaction is carried out by continuous stirring and pressurization. The pressurization pressure is greater than 2 MPa and the temperature is higher than 60 degrees. After the reaction is completed, the reaction mixed gas is first extracted and processed through ventilation equipment.

5. The method for preparing boson according to claim 1, characterized in that: In the step d) electrophilic substitution reaction, water is used as a nucleophilic reagent, and after the treatment, the reaction is heated in a water bath at a temperature between 30 and 60 degrees.

6. The method for preparing boson according to claim 1, characterized in that: In the step e) crystallization purification, the bosogenin solution to be purified is added to an appropriate amount of acetone solution, and stirred or heated to dissolve until it is completely dissolved. The solution is passed through a filter using appropriate filtering equipment to filter out solid particles or suspended matter to obtain a relatively pure solution. The enzyme crystals are introduced. Under the action of the inducer, the solute in the solution begins to crystallize and is wrapped around the surface of the enzyme crystals. During the crystallization process, the concentration of the solution will gradually increase, causing the substance to gradually transform into crystals.

7. The method for preparing boson according to claim 6, characterized in that: In the step e) of crystallization purification, the crystals are centrifuged to separate the solution, the crystals are washed with ethanol for multiple times to remove residual impurities, and the washed crystals are dried at low temperature to completely remove moisture.

8. The method for preparing boson according to claim 7, characterized in that: In the step e) of crystallization purification, the purity of bosphenic acid crystals can be determined by measuring the melting point of the crystals. When the purity of the crystals is lower than the required level, the crystals can be further purified by repeated crystallization.