CN110845735A - Hybrid silica gel for extracting lipophilic vitamins in peach gum and preparation method and extraction method thereof - Google Patents
Hybrid silica gel for extracting lipophilic vitamins in peach gum and preparation method and extraction method thereof Download PDFInfo
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- CN110845735A CN110845735A CN201911236815.9A CN201911236815A CN110845735A CN 110845735 A CN110845735 A CN 110845735A CN 201911236815 A CN201911236815 A CN 201911236815A CN 110845735 A CN110845735 A CN 110845735A
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
The invention discloses a hybrid silica gel material with a surface containing carbon chains, which is synthesized by using hexadecyl trimethyl ammonium bromide (CTAB) as a template agent and absolute ethyl alcohol as a solvent and adopting Tetraethoxysilane (TEOS) and aminopropyl triethoxysilane (APTES) dimethyl octadecyl [ 3-trimethoxy silicon propyl ] ammonium chloride through a part of method.
Description
Technical Field
The invention relates to hybrid silica gel, in particular to hybrid silica gel for extracting lipophilic vitamins in peach gum, and a preparation method and an extraction method thereof.
Background
Vitamins are a kind of trace organic substances which must be obtained from food for human and animals to maintain normal physiological functions, and play an important role in the growth, metabolism and development processes of human bodies. Vitamins can be classified into fat-soluble vitamins and water-soluble vitamins according to their solubility. Wherein the fat-soluble vitamins are vitamins insoluble in water and soluble in lipid and organic solvent, including vitamin A, D, E, K. At present, the vitamin determination method mainly adopts a liquid-liquid extraction technology, namely fat-soluble vitamins are extracted by an organic solvent, then are dried by nitrogen, and are re-dissolved by a mobile phase of liquid chromatography (HPLC). This process is not only time consuming and laborious, but also involves large amounts of organic solvents.
The Solid Phase Extraction (SPE) technology is used for enriching, separating and purifying samples by adopting selective adsorption and selective elution, comprises a liquid phase and solid phase physical extraction process, and is not only suitable for extracting and enriching trace organic compounds in food and environmental water samples, but also suitable for enriching trace components to be measured in biological samples. Compared with liquid-liquid extraction, SPE has less organic solvent involved in the determination process and simple operation process.
Peach gum is a colloid semitransparent substance secreted by trunks of plants such as peaches or wild peaches in Rosaceae after mechanical damage (such as insect bite, cutting wound and the like) or pathogenicity, and is also named peach oil and peach grease. According to the records of Tang materia Medica: sweet and bitter taste, mild and non-toxic. In recent years, the Chinese medicinal composition has obvious effects of treating urinary calculus and assisting in treating leukemia and diabetes, and has curative effects on pain, bloody stranguria, dysentery and the like. The peach gum can be used as food additive, and has the function of changing food physical properties; the product has effects of caring skin, controlling blood sugar, reducing blood lipid, nourishing brain, and improving intelligence; the functional characteristic of the adhesive can also be utilized to apply the paper pasting and paper gluing, etc. At present, most of the nutrients in peach gum are reported to be polysaccharide and protein, and no report is found about whether the peach gum contains vitamins.
The hybrid silica gel material can selectively adsorb different substances as a solid phase extraction adsorbent, so that the problems of liquid-liquid extraction in the current vitamin determination can be solved by adopting the modified hybrid silica gel to extract different types of vitamins in peach gum, and a novel adsorbent with high recovery rate is provided for the SPE determination technology.
Disclosure of Invention
The first technical problem to be solved by the invention is to provide a hybrid silica gel for extracting lipophilic vitamins in peach gum.
The technical scheme adopted by the invention for solving the technical problems is as follows: a hybrid silica gel for extracting lipophilic vitamins in peach gum is characterized in that a branched chain of the hybrid silica gel contains a hydrophobic carbon chain, and a basic unit of a chemical structural formula of the hybrid silica gel is as follows:
The second technical problem to be solved by the invention is to provide a preparation method of hybrid silica gel for extracting lipophilic vitamins in peach gum.
The technical scheme adopted by the invention for solving the technical problems is as follows: a preparation method of hybrid silica gel for extracting lipophilic vitamins in peach gum is characterized by comprising the following steps:
1) absolute ethyl alcohol is used as a solvent, and hexadecyl trimethyl ammonium bromide, tetraethoxy silane, aminopropyl triethoxy silane and dimethyl octadecyl [ 3-trimethoxy silicon propyl ] ammonium chloride are added;
2) adding water, and reacting the mixture to generate a hybrid silica gel material with a surface containing carbon chains;
3) washing with absolute ethyl alcohol;
the hybrid silica gel is prepared by hybridizing hexadecyl trimethyl ammonium bromide serving as a template agent with tetraethoxysilane, aminopropyl triethoxysilane and dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride, and the hybrid silica gel material synthesized from tetraethoxysilane and aminopropyl triethoxysilane is not provided with a hydrophobic carbon chain, so that the capability of retaining lipophilic vitamins is weak, the adsorption effect of the hybrid silica gel material is poor, and the capability of adsorbing the lipophilic vitamins of the hybrid silica gel material containing the carbon chain is enhanced by modifying the hybrid silica gel material with dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride, so that the extraction efficiency is improved.
Dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride, tetraethoxysilane and aminopropyl triethoxysilane are hydrolyzed and condensed by siloxy to form a Si-O-Si structure which is used as a framework of the hybrid silica gel material.
Preferably, the reaction conditions of step 2) are as follows: and heating the mixture at 28-35 ℃ until the hexadecyl trimethyl ammonium bromide is completely dissolved, and reacting at 38-45 ℃ for 20-40 h to generate the hybrid silica gel material.
Preferably, in the step 1), the volume ratio of aminopropyltriethoxysilane to tetraethoxysilane is: 0.9-1.2, wherein the ratio of the added dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride to the tetraethoxysilane is less than or equal to 1.52 g: 1 mL.
The volume ratio of aminopropyltriethoxysilane to tetraethoxysilane is as follows: 0.9-1.2, and a hybrid silica gel structure can be well formed.
The proportion of dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride and tetraethoxysilane is less than or equal to 1.52 g: 1mL, after multiple experiments, the white color of the hybrid silica gel gradually becomes lighter with the increase of the content of dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride, and when the ratio of the dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride to tetraethoxysilane is more than 1.52 g: at 1mL, the polymer can not be polymerized into a hybrid silica gel material, so the ratio of dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride to tetraethoxysilane is less than or equal to 1.52 g: 1 mL.
The third technical problem to be solved by the invention is to provide an extraction method of hybrid silica gel for extracting lipophilic vitamins in peach gum.
The technical scheme adopted by the invention for solving the technical problems is as follows: a method for extracting hybrid silica gel of lipophilic vitamin in peach gum is characterized in that: activating the prepared hybrid silica gel extraction column, adding a fat-soluble vitamin standard substance into the peach gum extracting solution, enabling the methanol concentration (v/v) of the peach gum extracting solution to be less than or equal to 40%, enabling the concentration of each sample to be 0.0001-0.1 mg/mL, loading 1mL, and enabling the mixture to flow through the solid phase extraction column at the flow rate of 1mL/min to finish loading; eluting with a buffer solution containing 80-90% (v/v) methanol and having a pH of 10.0-12.0 to obtain the fat-soluble vitamin.
Preferably, the hybrid silica gel extraction column is activated with 5.0mL of methanol and 5.0mL of water, respectively.
Preferably, the recovery rate of the fat-soluble vitamins is not less than 85%.
Preferably, the hybrid silica gel powder is packed in a 3mL column tube with a lower sieve plate having a pore size of 5 μm, packed in an upper sieve plate having a pore size of 20 μm, and then compacted.
Compared with the prior art, the invention has the advantages that: 1) cetyl Trimethyl Ammonium Bromide (CTAB) is used as a template agent, absolute ethyl alcohol is used as a solvent, Tetraethoxysilane (TEOS), aminopropyl triethoxysilane (APTES) and dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride are adopted to synthesize the hybrid silica gel material with the surface containing hydrophobic carbon chains in a one-step method, the hybrid silica gel material containing the hydrophobic carbon chains has the function of extracting fat-soluble vitamins, the extraction and determination of the fat-soluble vitamins in peach gum are met, and compared with the traditional liquid-liquid extraction, the solid-phase extraction method has the advantages that less organic solvents are involved in the determination process, and the operation process is simple.
2) The hydrophobic hybrid silica gel has good effect on the adsorption of fat-soluble vitamins, and the recovery rate is more than or equal to 85 percent.
Drawings
FIG. 1 is a schematic diagram of the preparation of the hybrid silica gel of the present invention;
FIG. 2 a is the IR spectrum analysis chart of hybrid silica gel material without dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride modification; b is an infrared spectrum analysis chart of the hybrid silica gel material modified by dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride;
FIG. 3 is a chromatogram of extraction of vitamin D3 from peach gum by using the hybrid silica gel material of example 5 as a solid phase extraction column. Peak 1: vitamin D2 as an internal standard; peak 2: vitamin D3, concentration 0.0004 mg/mL;
FIG. 4 is a chromatogram of extraction of vitamin A from peach gum by using the hybrid silica gel material as a solid phase extraction column in example 1 of the present invention. Peak 1: is vitamin A, the concentration is 0.02 mg/mL;
FIG. 5 is a scanning electron micrograph (X3500) of the hybrid silica gel of the present invention.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
The preparation method of the hybrid silica gel of the embodiment 1-10 comprises the following steps: 320mg of hexadecyl trimethyl ammonium bromide is weighed into a 50mL plastic centrifuge tube, 4.48mL of tetraethoxysilane, 4.72mL of aminopropyl triethoxysilane, 4000mg of dimethyl octadecyl [ 3-trimethoxy silylpropyl ] ammonium chloride and 8.7mL of absolute ethyl alcohol are added, the mixture is shaken by a vortex mixer and then subjected to water bath at 30 ℃ until the hexadecyl trimethyl ammonium bromide is completely dissolved, 1.28mL of water is added, the mixture is shaken and mixed by the vortex mixer, and the mixture is subjected to water bath reaction at 40 ℃ for 24 hours to generate the hybrid silica gel material.
Comparative example 1 is a hybrid silica gel without the addition of dimethyloctadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride.
Preparation of extraction column: the hybrid silica gel powder was packed into a 3mL column tube with a lower sieve plate of 5 μm pore size, packed into an upper sieve plate of 20 μm pore size and then compacted.
Preparation of peach gum samples:
1) treatment of peach gum
Soaking the peach gum in cold water for 24 hr, repeatedly washing with clear water, collecting the cleaned peach gum, vacuum drying at 80 deg.C, pulverizing with a multi-purpose plant pulverizer, and filtering with 80 mesh sieve for several times to obtain peach gum powder.
2) Method for extracting fat-soluble vitamins from peach gum (aiming at vitamins A and D)
Accurately weighing 2-5 g of peach gum powder into a 150mL flat-bottomed flask, adding about 20mL of warm water, adding 1.0g of ascorbic acid and 0.1g of BHT (2, 6-di-tert-butyl-p-methylphenol), uniformly mixing, adding 30mL of methanol, adding 10-20 mL of 50% (v/v) potassium hydroxide aqueous solution, vibrating while adding, uniformly mixing, oscillating in a constant-temperature water bath at 80 ℃, refluxing and saponifying for 30min, immediately cooling to room temperature with cold water after saponification, and adjusting the pH to be neutral with concentrated hydrochloric acid.
3) Adding vitamin A and D mixed standard sample into the peach gum extract, and diluting the peach gum extract with water until the methanol concentration (v/v) is less than or equal to 40%. And (3) extracting fat-soluble vitamins: the solid phase extraction column filled with the hybrid silica gel material is activated by 5.0mL of methanol and 5.0mL of water respectively. Each sample concentration is 0.0001-0.1 mg/mL, the sample loading is 1mL, and the sample flows through the solid phase extraction column at the flow rate of 1mL/min to finish the sample loading; subsequently, rinsing with < 40% (v/v) aqueous methanol to wash off impurities; then eluting with a buffer solution containing 2mL of 80-90% (v/v) methanol and having a pH of 10.0-12.0.
HPLC analytical testing and recovery determination: the effluent samples were collected and then analyzed by HPLC for assay and recovery.
The examples are the same as the comparative examples for the preparation of the extraction column, the samples used, the activation of the extraction column and the loading conditions.
As shown in Table 1, the hybrid silica gel of comparative example 1 contains no carbon chain, and does not have the capacity of adsorbing fat-soluble vitamins under the condition of satisfying elution, so that A and D are not detected by HPLC; examples 1 to 10 are hybrid silica gels containing hydrophobic carbon chains, which have retention ability for fat-soluble vitamins, so that detection of fat-soluble vitamins by HPLC detection indicates that the hybrid silica gels have the ability to adsorb fat-soluble vitamins, and examples 1 to 8 indicate that the hybrid silica gels have excellent adsorption ability, because the recovery rate of the fat-soluble vitamins is not less than 85% under the condition of satisfying elution. Example 9 and example 10 other elution conditions were used, and HPLC detected A and D, but the recovery was only 35% and 32%, respectively, indicating that the elution was poor.
2853 and 2926cm can be seen from the infrared spectra of a and b in FIG. 2-1is-CH2Symmetric stretching vibration and antisymmetric stretching vibration of-type, via dimethyldecaOctaalkyl [ 3-trimethoxysilylpropyl group]The hybrid silica gel material modified by ammonium chloride contains long carbon chain C18, so the absorption intensity of the two peaks in b is higher than that of the hybrid silica gel material without dimethyl octadecyl [ 3-trimethoxy silicon propyl group]The high absorption strength of the ammonium chloride modification indicates that the dimethyl octadecyl [ 3-trimethoxysilylpropyl group]Ammonium chloride is preferably synthesized in hybrid silica gels.
As can be seen from FIG. 5, the hybrid silica gel of the present invention is formed by linking small spheres with a particle size of 1-5 μm to form a porous hybrid silica gel, wherein the pores are about 2-3 μm. The small ball with the particle size of 1-5 microns increases the specific surface area for adsorbing fat-soluble vitamins, and the pores between the small balls improve the permeability, so that the solvent can pass through the pores.
Table 1 vitamin detection and recovery test under different elution conditions for the examples of the invention and the comparative examples
Claims (8)
1. A hybrid silica gel for extracting lipophilic vitamins in peach gum is characterized in that a branched chain of the hybrid silica gel contains a hydrophobic carbon chain, and a basic unit of a chemical structural formula of the hybrid silica gel is as follows:
2. A method for preparing a hybrid silica gel for extracting lipophilic vitamins from peach gum according to claim 1, which comprises the following steps:
1) adding cetyl trimethyl ammonium bromide, tetraethoxysilane, aminopropyl triethoxysilane and dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride into anhydrous ethanol solvent;
2) reacting the mixture to generate a hybrid silica gel material with a surface containing carbon chains;
3) washing with anhydrous ethanol.
3. The method for preparing the hybrid silica gel for extracting lipophilic vitamins from peach gum as claimed in claim 2, wherein the reaction conditions of the step 2) are as follows: and heating the mixture at 28-35 ℃ until the hexadecyl trimethyl ammonium bromide is completely dissolved, and reacting at 38-45 ℃ for 20-40 h to generate the hybrid silica gel material.
4. The method for preparing the hybrid silica gel for extracting the lipophilic vitamins from the peach gum as claimed in claim 2, wherein the volume ratio of the aminopropyltriethoxysilane to the tetraethoxysilane added in the step 1) is as follows: 0.9-1.2, wherein the ratio of the added dimethyl octadecyl [ 3-trimethoxysilylpropyl ] ammonium chloride to the tetraethoxysilane is less than or equal to 1.52 g: 1 mL.
5. A method for extracting the hybrid silica gel of claim 1 for extracting lipophilic vitamins from peach gum, which comprises the following steps: activating the prepared hybrid silica gel extraction column, adding a fat-soluble vitamin standard substance into the peach gum extracting solution, enabling the methanol concentration (v/v) of the peach gum extracting solution to be less than or equal to 40%, enabling the concentration of each sample to be 0.0001-0.1 mg/mL, loading 1mL, and enabling the mixture to flow through the solid phase extraction column at the flow rate of 1mL/min to finish loading; eluting with a buffer solution containing 80-90% (v/v) methanol and having a pH of 10.0-12.0 to obtain the fat-soluble vitamin.
6. The method for extracting the hybrid silica gel of lipophilic vitamin from peach gum as claimed in claim 5, wherein the method comprises the following steps: the hybrid silica gel extraction column was activated with 5.0mL methanol and 5.0mL water, respectively.
7. The method for extracting the hybrid silica gel of lipophilic vitamin from peach gum as claimed in claim 5, wherein the method comprises the following steps: the recovery rate of the fat-soluble vitamins is more than or equal to 85 percent.
8. The method for extracting the hybrid silica gel of lipophilic vitamin from peach gum as claimed in claim 5, wherein the method comprises the following steps: the preparation process of the extraction column comprises the following steps: the hybrid silica gel powder was packed into a 3mL column tube with a lower sieve plate of 5 μm pore size, packed into an upper sieve plate of 20 μm pore size and then compacted.
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| CN112083108A (en) * | 2020-09-23 | 2020-12-15 | 辽宁润生康泰医学检验实验室有限公司 | Accurate detection method and kit for folic acid in blood |
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| CN102993229A (en) * | 2012-12-19 | 2013-03-27 | 宁波工程学院 | Amphoteric electrolyte-modified hybrid silica gel material and solid-phase extraction method thereof |
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| CN102993229A (en) * | 2012-12-19 | 2013-03-27 | 宁波工程学院 | Amphoteric electrolyte-modified hybrid silica gel material and solid-phase extraction method thereof |
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| CN112083108A (en) * | 2020-09-23 | 2020-12-15 | 辽宁润生康泰医学检验实验室有限公司 | Accurate detection method and kit for folic acid in blood |
| CN112083108B (en) * | 2020-09-23 | 2021-04-27 | 辽宁润生康泰医学检验实验室有限公司 | Accurate detection method and kit for folic acid in blood |
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