CN111393276B - Extraction method of natural p-hydroxybenzaldehyde - Google Patents
Extraction method of natural p-hydroxybenzaldehyde Download PDFInfo
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- CN111393276B CN111393276B CN201910575257.2A CN201910575257A CN111393276B CN 111393276 B CN111393276 B CN 111393276B CN 201910575257 A CN201910575257 A CN 201910575257A CN 111393276 B CN111393276 B CN 111393276B
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- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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Abstract
The invention discloses an extraction method of natural p-hydroxybenzaldehyde, which takes triarrhena sacchariflora as an extraction object to extract the natural p-hydroxybenzaldehyde, wherein the extraction object is preferably triarrhena sacchariflora tender stem, in particular to triarrhena sacchariflora tender stem without shell or waste bamboo shoot shell of the triarrhena sacchariflora tender stem or waste bamboo shoot head of the triarrhena sacchariflora tender stem. The method disclosed by the invention is initiated in the field by selecting the triarrhena sacchariflora as the extraction object, has the advantages of sufficient raw material source, simple and convenient process, low cost, high product purity, less impurities, environmental friendliness, large-scale production, high commercial value and wide application prospect.
Description
Technical Field
The invention relates to an extraction method of natural products, in particular to a method for extracting natural p-hydroxybenzaldehyde from tender stems of Triarrhena (Triarrhena luteoria L Liu).
Background
P-hydroxybenzaldehyde is an important intermediate in the fragrance industry and in the pharmaceutical industry. It is used in the perfume industry for synthesizing the perfumes such as vanillin, ethyl vanillin, heliotropin, syringaldehyde, anisaldehyde and raspberry ketone. Can be used for synthesizing amoxicillin (amoxicillin), antibacterial synergist Trimethoprim (TMP), 3,4, 5-trimethoxybenzaldehyde, p-hydroxy glycine, amoxicillin cefadriamycin, artificial rhizoma Gastrodiae, farrerol, and abrin.
At present, the preparation method of the parahydroxybenzaldehyde is mainly chemical preparation, and the chemical preparation method of the parahydroxybenzaldehyde mainly has a synthetic route taking phenol or p-nitrotoluene or p-methylphenol as raw materials.
The method using phenol as the starting material is divided into a plurality of synthetic process routes such as Reimer-Tiemann reaction, gattermann reaction, phenol-chloral route, phenol-glyoxylic acid route, phenol-formaldehyde route and the like. The phenol method has the technical characteristics of easily obtained raw materials, simpler manufacturing process, more difficult separation and purification in the later period, lower yield and higher cost.
The process for producing p-hydroxybenzaldehyde by taking p-nitrotoluene as a starting material comprises three steps of oxidation reduction, diazotization and hydrolysis. The process has the characteristics of low raw material price, long process route, complex process and toxic intermediate product.
The synthetic route using p-methyl phenol as raw material is to oxidize p-methyl phenol by transition metal catalytic air or oxygen in a pressure container to obtain the target product. The method has harsh technological conditions, and the oxygen introduction rate, the total oxygen introduction amount and the reaction temperature are strictly controlled.
In conclusion, the chemical process for preparing p-hydroxybenzaldehyde inevitably involves problems such as environmental pollution, complicated process conditions or high costs, and therefore, it is necessary and practical to develop a new process for preparing p-hydroxybenzaldehyde.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides the method for extracting the natural p-hydroxybenzaldehyde, which has the advantages of easily obtained raw materials, simple and convenient process, high yield and low cost.
In order to solve the technical problems, the invention adopts the following technical scheme.
An extraction method of natural p-hydroxybenzaldehyde, which takes Triarrhena sacchariflora L Liu as an extraction object to extract the natural p-hydroxybenzaldehyde.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, the extraction target is tender stems of triarrhena sacchariflora.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, the extraction object is peeled triarrhena armandii tender stem or waste bamboo shoot shell of triarrhena armandii tender stem or waste bamboo shoot head of triarrhena armandii tender stem.
Among the above-mentioned methods for extracting natural parahydroxybenzaldehyde, the preferred method for extracting natural parahydroxybenzaldehyde is as follows:
(1) Heating and drying the peeled triarrhena sacchariflora tender stem or waste bamboo shoot shells of the triarrhena sacchariflora tender stem or waste bamboo shoot heads of the triarrhena sacchariflora tender stem, and crushing and sieving to obtain triarrhena sacchariflora tender stem dry powder;
(2) Adding the triarrhena sacchariflora tender stem dry powder into a polar organic solvent to obtain a suspension, standing or vibrating the suspension at room temperature, soaking and extracting, and performing suction filtration and reduced pressure concentration to obtain a crude extract of natural p-hydroxybenzaldehyde;
(3) And separating and purifying the crude extract of the natural p-hydroxybenzaldehyde to obtain the natural p-hydroxybenzaldehyde.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, in the step (1), the temperature for heating and drying is controlled to be 40-80 ℃, and the sieving is a 40-mesh sieve;
and/or in the step (2), the mass of the polar organic solvent is 4-10 times of that of the dry powder of the amur silvergrass twig, the polar organic solvent comprises at least one of ethanol (with the volume concentration of 70-100%), methanol, diethyl ether, tetrahydrofuran, 1, 4-dioxane and acetonitrile, the soaking and extraction time is 4 hours to 5 days, the vibration is to shake the suspension on a shaking table or to perform ultrasonic-assisted oscillation on the suspension to obtain the crude extract of the natural p-hydroxybenzaldehyde, and then the crude extract of the natural p-hydroxybenzaldehyde is stored in a dark place under the conditions of sealing and shading.
In the above method for extracting natural p-hydroxybenzaldehyde, it is more preferable that the temperature of the heating and drying in the step (1) is controlled to be 50 to 60 ℃.
Among the above-mentioned methods for extracting natural parahydroxybenzaldehyde, the preferred method for extracting natural parahydroxybenzaldehyde is as follows:
(1) Cutting or crushing fresh triarrhena armandii tender stem or waste bamboo shoot shell of triarrhena armandii tender stem or waste bamboo shoot head of triarrhena armandii tender stem to obtain triarrhena armandii tender stem fragments, leaching the triarrhena armandii tender stem fragments by hot water or ethanol, filtering to remove solid residues, concentrating the obtained filtrate under reduced pressure to obtain solute residues, extracting natural p-hydroxybenzaldehyde from the solute residues by adopting an organic solvent, washing and concentrating to obtain crude extracts of the natural p-hydroxybenzaldehyde;
(2) And separating and purifying the crude extract of the natural p-hydroxybenzaldehyde to obtain the natural p-hydroxybenzaldehyde.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, in the step (1), when hot water extraction is adopted, the temperature of the hot water is 60 ℃ to 90 ℃, the extraction time is 2 hours to 5 hours, after extraction, the obtained suspension is allowed to stand at room temperature for 12 hours to 24 hours, and then filtered;
when ethanol is used for leaching, the leaching time is 12 to 60 hours.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, the crude extract of natural p-hydroxybenzaldehyde is separated and purified by column chromatography or recrystallization.
In the above method for extracting natural p-hydroxybenzaldehyde, preferably, when column chromatography is adopted for separation and purification, forward chromatography is adopted, silica gel of 100-300 meshes is taken as a stationary phase, and one of petroleum ether/ethyl acetate, n-hexane/ethyl acetate and cyclohexane/ethyl acetate is taken as a mobile phase;
when recrystallization is used for separation and purification, the solvent is water or an organic solvent.
In the present invention, p-hydroxybenzaldehyde has a chemical structural formula represented by formula (1), and is a colorless needle crystal:
in the present invention, when the crude extract of natural p-hydroxybenzaldehyde is separated and purified by column chromatography, the following steps can be preferably adopted: weighing crude extract of natural p-hydroxybenzaldehyde, dissolving with appropriate amount of organic solvent, adding silica gel, stirring, evaporating organic solvent to make sample adsorbed by silica gel, loading to silica gel column, eluting with eluent, and collecting target eluate. Wherein, the organic solvent can be absolute ethyl alcohol, aether, dichloromethane and the like, the silica gel is 100-300 meshes of silica gel, and the eluent can be one of petroleum ether/ethyl acetate, n-hexane/ethyl acetate, hexane/ethyl acetate and the like. Petroleum ether/ethyl acetate means a combination of petroleum ether and ethyl acetate, as otherwise described herein.
Compared with the prior art, the invention has the advantages that:
the invention provides a method for extracting natural p-hydroxybenzaldehyde from triarrhena sacchariflora, the triarrhena sacchariflora is a plant widely distributed in lake beaches and riversides in middle and lower regions of Yangtze river in China, and the method selects the triarrhena sacchariflora as an extraction object and is pioneer in the field. The raw material of the invention can be the whole triarrhena armandii tender stem, preferably the peeled triarrhena armandii tender stem or the waste bamboo shoot shell of the triarrhena armandii tender stem or the waste bamboo shoot head (the waste bamboo shoot head when the triarrhena armandii tender stem is picked) when the triarrhena armandii tender stem is peeled, and the like, thus not only the main components of the triarrhena armandii tender stem, but also the waste part can be utilized, and the effective utilization of waste is realized. The method has the advantages of easily available raw materials and sufficient sources, is suitable for large-scale production, and has great significance for fully developing the triarrhena sacchariflora. The applicant finds in research that the content of the p-hydroxybenzaldehyde in the triarrhena sacchariflora is high, the p-hydroxybenzaldehyde is extracted by adopting the triarrhena sacchariflora, and the prepared natural p-hydroxybenzaldehyde has high purity, less impurities and high safety because the raw materials are safe and easy to obtain and the solvent used in the process method is relatively safe, so that the prepared natural p-hydroxybenzaldehyde is obviously superior to the p-hydroxybenzaldehyde prepared by the existing chemical method and has higher commercial value.
The method for directly extracting the natural p-hydroxybenzaldehyde from the triarrhena sacchariflora has simple and convenient process, simple equipment requirement and low cost, and avoids the defects of multiple steps, complex process, complicated purification, high cost, environmental pollution and the like of a chemical preparation method. The method of the invention can provide p-hydroxybenzaldehyde in a large scale, and provides a new solution for meeting the requirements of producing downstream products.
Drawings
FIG. 1 is a TIC total ion flux map of crude extract of natural p-hydroxybenzaldehyde according to example 1 of the present invention.
FIG. 2 is a MS (EI) spectrum of natural p-hydroxybenzaldehyde according to example 1 of the present invention.
FIG. 3 is a TIC total ion flux map of crude extract of natural p-hydroxybenzaldehyde according to example 2 of the present invention.
FIG. 4 is a TIC total ion flow diagram of crude natural p-hydroxybenzaldehyde extract of example 3 of the present invention.
Detailed Description
The invention is further described below with reference to the drawings and specific preferred embodiments of the description, without thereby limiting the scope of protection of the invention.
The materials and equipment used in the following examples are commercially available.
Example 1
The invention relates to a method for extracting natural p-hydroxybenzaldehyde, which comprises the following steps:
(1) Removing shell of picked tender stems (about 10-25 cm long and about 2cm diameter near the root), heating at 60 deg.C, oven drying, pulverizing, and sieving with 40 mesh sieve to obtain dry powder of tender stems of triarrhena sacchariflora.
(2) Taking 10 g of triarrhena armandii tender stem dry powder, placing the powder in a glass container, adding 50 g of ethanol with the volume concentration of 95% to obtain a suspension, sealing, standing at room temperature, soaking for 24 hours, or shaking the suspension on a shaking table, or placing the suspension in an ultrasonic instrument and extracting with the aid of ultrasound. Extracting, filtering, concentrating the filtrate under reduced pressure to obtain crude extract of natural p-hydroxybenzaldehyde 1.6 g, sealing, keeping in the dark, and storing. The TIC total ion flow diagram of the crude extract is shown in FIG. 1, and the chromatographic peak with the retention time of 19.26 minutes is p-hydroxybenzaldehyde.
(3) Separating and purifying the crude extract of the p-hydroxybenzaldehyde by using column chromatography, firstly dissolving the crude extract by using a small amount of absolute ethyl alcohol, adding about 5 g of 200-300 mesh silica gel, carrying out reduced pressure spin-drying to enable a sample to be adsorbed on the silica gel, and then adding another proper amount of siliconPacking the gel into chromatographic column, loading by dry method, eluting with cyclohexane/ethyl acetate (v/v = 3/1), and collecting R f =0.4 sample, and 0.8 g of pure natural p-hydroxybenzaldehyde is obtained. The MS (EI) spectrum of the obtained natural p-hydroxybenzaldehyde is shown in figure 2, and the mass spectrum is consistent with the spectrum of a standard sample of the p-hydroxybenzaldehyde, which confirms that the invention really obtains the p-hydroxybenzaldehyde.
Example 2
The invention relates to a method for extracting natural p-hydroxybenzaldehyde, which comprises the following steps:
(1) The picked tender stems of the triarrhena sacchariflora (about 10-25 cm long and about 2cm diameter close to the root) are shelled, each fresh shelled tender stem of the triarrhena sacchariflora is cut into four petals along the stem direction, then is transversely cut into 2-3 cm/segment, 1000 g of cut tender stem is added with 2000 g of water, is heated for 2 hours in a water bath at the temperature of 60 ℃, then is kept stand and soaked for 14 hours at the room temperature, is filtered to obtain brown water solution, and the brown water solution is concentrated under reduced pressure to obtain 60 g of solute residue. Adding 600mL acetonitrile into solute residue for extraction and 100mL saturated salt water for washing, shaking, standing, separating, filtering floccule in acetonitrile layer, concentrating acetonitrile under reduced pressure (distilling under reduced pressure) to obtain 3.1 g crude extract of natural p-hydroxybenzaldehyde, detecting by GC-MS that the chromatographic purity of p-hydroxybenzaldehyde in the crude extract is 88%, and the TIC total ion flow diagram is shown in figure 3, and the chromatographic peak with retention time of 19.26 minutes is p-hydroxybenzaldehyde.
(2) Recrystallizing the crude extract of 3.1 g of natural p-hydroxybenzaldehyde with water to obtain a pure product of 1.3 g of natural p-hydroxybenzaldehyde.
Example 3
The invention relates to a method for extracting natural p-hydroxybenzaldehyde, which comprises the following steps:
(1) The method comprises the steps of shelling picked tender stems of the triarrhena armandii (about 10-25 cm long and about 2cm diameter close to the root), crushing 150 g of shelled tender stems of the triarrhena armandii with a juicer, adding 200mL of absolute ethyl alcohol, soaking for 60 hours, carrying out suction filtration, carefully extruding liquid contained in filter residues, carrying out reduced pressure evaporation on the ethyl alcohol and water in filtrate to obtain solute residues, adding 180mL of acetonitrile into the solute residues for leaching, adding 40 g of saturated saline solution for washing, shaking, transferring into a separating funnel for standing, carrying out liquid separation, concentrating an acetonitrile layer to obtain 0.48 g of crude extract of natural p-hydroxybenzaldehyde, wherein a TIC total ion flow diagram is shown in figure 4, and a chromatographic peak with the retention time of 19.26 minutes is p-hydroxybenzaldehyde.
(2) Separating and purifying the crude extract of the p-hydroxybenzaldehyde by using column chromatography, firstly dissolving the crude extract by using a small amount of absolute ethyl alcohol, adding 2 g of 200-300 mesh silica gel, carrying out reduced pressure spin-drying to enable a sample to be adsorbed on the silica gel, then filling another proper amount of silica gel into the chromatographic column, eluting by using an eluent cyclohexane/ethyl acetate (v/v = 3/1) after dry-method sample loading, and collecting R f =0.4 sample, and 0.31 g of pure natural p-hydroxybenzaldehyde is obtained.
The foregoing is illustrative of the preferred embodiments of the present invention and is not to be construed as limiting the invention in any way. Although the present invention has been described with reference to the preferred embodiments, it is not intended to be limited thereto. Those skilled in the art can make many variations and modifications to the disclosed embodiments, or equivalent variations, without departing from the spirit and scope of the invention, using the methods and techniques disclosed above. Therefore, any simple modification, equivalent replacement, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the scope of the protection of the technical solution of the present invention.
Claims (6)
1. The extraction method of natural p-hydroxybenzaldehyde is characterized in that the extraction method is that the triarrhena sacchariflora (triarrhena sacchariflora) (A.Merr.) (B.saccharina)Triarrhena lutarioriparia L Liu) Extracting natural p-hydroxybenzaldehyde as an extraction object, wherein the extraction object is the peeled triarrhena sacchariflora tender stem or the waste bamboo shoot shell of the triarrhena sacchariflora tender stem or the waste bamboo shoot head of the triarrhena sacchariflora tender stem;
the extraction method comprises the following steps:
(1) Heating and drying the peeled triarrhena sacchariflora tender stem or waste bamboo shoot shells of the triarrhena sacchariflora tender stem or waste bamboo shoot heads of the triarrhena sacchariflora tender stem, and crushing and sieving to obtain triarrhena sacchariflora tender stem dry powder;
(2) Adding the dry powder of the tender stems of the triarrhena sacchariflora into a polar organic solvent to obtain a suspension, standing or vibrating the suspension at room temperature, soaking and extracting, and performing suction filtration and reduced pressure concentration to obtain a crude extract of the natural p-hydroxybenzaldehyde;
(3) Separating and purifying the crude extract of the natural p-hydroxybenzaldehyde to obtain the natural p-hydroxybenzaldehyde;
in the step (1), the heating and drying temperature is controlled to be 40-80 ℃, and the sieving is to be a 40-mesh sieve;
in the step (2), the mass of the polar organic solvent is 4-10 times of that of the dry powder of the tender stems of the triarrhena sacchariflora, the polar organic solvent comprises at least one of ethanol, methanol, diethyl ether, tetrahydrofuran, 1, 4-dioxane and acetonitrile, the soaking and extraction time is 4 hours to 5 days, the vibration is to shake the suspension on a shaking table or to vibrate the suspension with the assistance of ultrasound to obtain the crude extract of the natural p-hydroxybenzaldehyde, and then the crude extract of the natural p-hydroxybenzaldehyde is stored in a dark place under the conditions of sealing and keeping out of the sun.
2. The method for extracting natural p-hydroxybenzaldehyde according to claim 1, wherein the temperature of the heating and drying is controlled to be 50-60 ℃ in the step (1).
3. The extraction method of natural p-hydroxybenzaldehyde is characterized in that the extraction method is implemented by using triarrhena sacchariflora (triarrhena sacchariflora) (triarrhena sacchariflora: (triarrhena sacchariflora)Triarrhena lutarioriparia L Liu) Extracting natural p-hydroxybenzaldehyde as an extraction object, wherein the extraction object is the peeled triarrhena sacchariflora tender stem or the waste bamboo shoot shell of the triarrhena sacchariflora tender stem or the waste bamboo shoot head of the triarrhena sacchariflora tender stem;
the extraction method comprises the following steps:
(1) Cutting or smashing fresh peeled triarrhena armandii tender stem or waste bamboo shoot shells of the triarrhena armandii tender stem or waste bamboo shoot heads of the triarrhena armandii tender stem to obtain triarrhena armandii tender stem fragments, leaching the triarrhena armandii tender stem fragments by hot water or ethanol, filtering to remove solid residues, concentrating the obtained filtrate under reduced pressure to obtain solute residues, extracting natural p-hydroxybenzaldehyde from the solute residues by adopting an organic solvent, wherein the organic solvent is acetonitrile, and washing and concentrating to obtain crude extracts of the natural p-hydroxybenzaldehyde;
(2) And separating and purifying the crude extract of the natural p-hydroxybenzaldehyde to obtain the natural p-hydroxybenzaldehyde.
4. The method for extracting natural p-hydroxybenzaldehyde according to claim 3, wherein in the step (1), when hot water extraction is adopted, the temperature of the hot water is 60 ℃ to 90 ℃, the extraction time is 2 hours to 5 hours, after the extraction, the obtained suspension is allowed to stand at room temperature for 12 hours to 24 hours, and then filtered;
when ethanol is used for leaching, the leaching time is 12 to 60 hours.
5. The method for extracting natural p-hydroxybenzaldehyde according to any one of claims 1 to 4, wherein the crude extract of natural p-hydroxybenzaldehyde is separated and purified by column chromatography or recrystallization.
6. The method for extracting natural p-hydroxybenzaldehyde according to claim 5, wherein when the column chromatography is adopted for separation and purification, the forward chromatography is adopted, silica gel of 100-300 meshes is taken as a stationary phase, and one of petroleum ether/ethyl acetate, n-hexane/ethyl acetate and cyclohexane/ethyl acetate is taken as a mobile phase;
when recrystallization is used for separation and purification, the solvent is water or an organic solvent.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111055A (en) * | 2015-09-23 | 2015-12-02 | 昆明理工大学 | Method for preparing natural p-hydroxy benzaldehyde from bamboo shoots |
| CN107935834A (en) * | 2017-11-17 | 2018-04-20 | 西北化工研究院 | A kind of synthetic method of parahydroxyben-zaldehyde |
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|---|---|---|---|---|
| CN105111055A (en) * | 2015-09-23 | 2015-12-02 | 昆明理工大学 | Method for preparing natural p-hydroxy benzaldehyde from bamboo shoots |
| CN107935834A (en) * | 2017-11-17 | 2018-04-20 | 西北化工研究院 | A kind of synthetic method of parahydroxyben-zaldehyde |
Non-Patent Citations (3)
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| 芒草中总黄酮的提取工艺研究及其挥发油成分的鉴定;徐乐乐等;《植物科学学报》;20160816;第34卷(第4期);第622-629页 * |
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