CN111760033B - Method for preparing beta-cyclodextrin and essential oil inclusion compound by alkaline electrolytic water method - Google Patents
Method for preparing beta-cyclodextrin and essential oil inclusion compound by alkaline electrolytic water method Download PDFInfo
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- CN111760033B CN111760033B CN202010534051.8A CN202010534051A CN111760033B CN 111760033 B CN111760033 B CN 111760033B CN 202010534051 A CN202010534051 A CN 202010534051A CN 111760033 B CN111760033 B CN 111760033B
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- essential oil
- cyclodextrin
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- 239000000341 volatile oil Substances 0.000 title claims abstract description 68
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 50
- 239000001116 FEMA 4028 Substances 0.000 title claims abstract description 44
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 44
- 235000011175 beta-cyclodextrine Nutrition 0.000 title claims abstract description 44
- 229960004853 betadex Drugs 0.000 title claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 12
- 239000000839 emulsion Substances 0.000 claims abstract description 6
- 239000012065 filter cake Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 238000000967 suction filtration Methods 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 235000009024 Ceanothus sanguineus Nutrition 0.000 claims description 18
- 240000003553 Leptospermum scoparium Species 0.000 claims description 18
- 235000015459 Lycium barbarum Nutrition 0.000 claims description 18
- 235000010254 Jasminum officinale Nutrition 0.000 claims description 6
- 241000220317 Rosa Species 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 240000005385 Jasminum sambac Species 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 241000207840 Jasminum Species 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 2
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
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- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- -1 cyclic oligosaccharide Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003215 pyranoses Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036620 skin dryness Effects 0.000 description 1
- 230000037394 skin elasticity Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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Abstract
The invention discloses a method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method, which comprises the following steps: (1) Dissolving the recrystallized beta-cyclodextrin in alkaline electrolyzed water with the pH =10-12 to obtain a solution I; dissolving the essential oil in absolute ethyl alcohol to obtain a solution II; (2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 20-75 ℃ for 3-7h to obtain emulsion; adjusting the temperature to room temperature, standing for 24-48h, filtering, washing a filter cake with absolute ethyl alcohol, performing suction filtration to obtain a white solid, and drying to obtain the beta-cyclodextrin and essential oil inclusion compound. The invention introduces alkaline electrolyzed water as a solvent and a medium, provides favorable reaction conditions for inclusion reaction, and the alkaline electrolyzed water can be naturally recovered to the state of neutral water after being used, thereby being green and environment-friendly. The beta-cyclodextrin and essential oil inclusion compound has high inclusion rate and yield, and has the advantages of simple operation, low energy consumption and simple post-treatment.
Description
Technical Field
The invention belongs to the chemical field of beta-cyclodextrin inclusion compound synthesis, the field of green chemistry and the technical field of essential oil inclusion compound preparation, and particularly relates to a method for preparing beta-cyclodextrin and tea tree essential oil inclusion compounds by an alkaline electrolyzed water method.
Background
Essential Oil (Tree Oil) is volatile aromatic substance obtained by distilling root, stem and leaf of plant with steam, cold soaking or solvent extraction, and is mostly liquid at room temperature, and few solid with special fragrance. Common essential oils include tea tree essential oil, jasmine essential oil, rose essential oil, and the like. Each plant essential oil has a chemical structure to determine its fragrance, color, fluidity and the way it operates with the system, and each plant essential oil has a specific set of functional characteristics. For example, the tea tree essential oil has the effects of resisting bacteria, corrosion and oxidation, is a more effective medicament than the traditional corrosion inhibitor, and has certain antiviral activity, anti-inflammatory activity and anti-tumor activity; the jasmine essential oil can relieve depression, revivify, improve self-confidence, and care and improve skin dryness; the rose essential oil has good effects of beautifying and protecting skin, can nourish interior and exterior, fade spots, promote melanin decomposition and restore skin elasticity. The essential oil has a plurality of advantages and can be widely applied to the fields of medicines, foods, daily necessities and the like.
Cyclodextrins (CD) are produced from starch by enzymatic hydrolysis. Cyclodextrin molecules are classified into alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-CD) and gamma-cyclodextrin (gamma-CD) according to the number of pyranoses contained. The yield of the beta-CD accounts for more than 95 percent of that of a cyclodextrin product due to the characteristics of low production cost, proper cavity structure and the like. The beta-CD is a cyclic oligosaccharide formed by connecting 7 chair-shaped D-pyranose monomers through alpha- (1,4) glycosidic bonds, and the molecular appearance is in a ring hollow conical cylinder shape with a narrow top and a wide bottom. beta-CD can be combined with a plurality of hydrophobic guest molecules due to the special ring structure of 'internal hydrophobicity and external hydrophilicity', and forms inclusion compounds through intermolecular force, van der Waals force and the like. In recent years, beta-CD has become more and more widely used in the fields of chromatographic separation, food and molecular catalysis.
The electrolyzed water is produced by direct current electrolysis of a dilute potassium chloride or sodium chloride solution in an electrolytic cell. After the electrolysis starts, under the influence of an electric field, OH < - > is oxidized in the anode region to generate O2 and H2O, the concentration of OH < - > is gradually reduced, the solution is acidic, and acidic electrolyzed water is generated; h + in the cathode region is reduced to generate H2, and the solution is alkaline due to the gradual reduction of the H + concentration, so that alkaline electrolyzed water is generated. The alkaline electrolyzed water has excellent degerming performance as multifunctional ionized water with alkaline characteristics, but no report of applying the alkaline electrolyzed water to the synthesis of beta-CD inclusion compounds exists at present.
The essential oil is greatly limited in storage and application because of its strong volatility and easy oxidation in air. To improve the stability of essential oils, masking the pungent odor of essential oils, essential oils are often prepared with β -CD as an inclusion compound. Although the utilization of essential oil is improved in the current synthetic method, the specific product stability is not reported in detail, the inclusion rate and the yield of the product are low, the reaction condition is complex, and the utilization rate of raw materials is not ideal.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for preparing beta-cyclodextrin and essential oil inclusion compounds by an alkaline electrolytic water method.
The technical scheme of the invention is summarized as follows:
a method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method comprises the following steps:
(1) Dissolving the recrystallized beta-cyclodextrin in alkaline electrolyzed water with the pH =10-12 to obtain a solution I; dissolving the essential oil in absolute ethyl alcohol to obtain a solution II;
(2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 20-75 ℃ for 3-7h to obtain an emulsion; adjusting the temperature to room temperature, standing for 24-48h, filtering, washing a filter cake with absolute ethyl alcohol, and performing suction filtration to obtain a white solid; and (3) drying the white solid in vacuum for 4-6h to obtain the beta-cyclodextrin and essential oil inclusion compound.
Preferably, the ratio of beta-cyclodextrin to alkaline electrolyzed water of pH =10-12 is 1g (20 mL-40 mL).
Preferably, the mass ratio of the absolute ethyl alcohol to the essential oil is 1 (1.7-5.2).
Preferably, the mass ratio of the essential oil to the beta-cyclodextrin is 1 (0.997-1.58).
The essential oil is preferably tea tree essential oil, jasmine essential oil or rose essential oil, and may be other essential oils.
The invention has the advantages that:
the invention provides a method for preparing beta-cyclodextrin and essential oil inclusion compounds by adopting green alkaline electrolyzed water, the alkaline electrolyzed water is introduced to serve as a solvent and a medium, favorable reaction conditions are provided for inclusion reaction, the alkaline electrolyzed water can be naturally recovered to a neutral water state after being used, and the method has the characteristics of green and environmental protection. The beta-cyclodextrin and essential oil inclusion compound prepared by the method has higher inclusion rate and yield which respectively reach 54.35 percent and 80.26 percent, the stability of essential oil in the essential oil inclusion compound is greatly enhanced, and meanwhile, the process has the advantages of simple operation, low energy consumption and simple post-treatment.
Drawings
FIG. 1 is an infrared spectrum of beta-CD;
FIG. 2 is an infrared spectrum of an inclusion compound of beta-cyclodextrin and tea tree essential oil;
FIG. 3 is an X-ray diffraction pattern of β -CD;
FIG. 4 is an X-ray diffraction pattern of beta-cyclodextrin and tea tree essential oil inclusion compound;
FIG. 5 is a DSC of β -CD;
FIG. 6 is a DSC chart of inclusion compound of beta-cyclodextrin and tea tree essential oil.
Detailed Description
The invention is further illustrated by the following examples, which are intended to be exemplary and representative of specific embodiments, and are not to be construed as limiting the scope of the invention.
Example 1
A method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method comprises the following steps:
(1) Dissolving 60g (0.0529 mol) of recrystallized beta-cyclodextrin (beta-CD) (see fig. 1, 3 and 5) in 1200mL of alkaline electrolyzed water with pH =10 to obtain a solution one; dissolving 37.9g (0.0529 mol) of tea tree essential oil in 7.3g (0.1587 mol) of absolute ethyl alcohol to obtain a solution II;
(2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 20 ℃ for 7 hours to obtain emulsion; adjusting the temperature to room temperature, standing for 24h, filtering, washing a filter cake with absolute ethyl alcohol, removing unreacted tea tree essential oil and impurities, and performing suction filtration to obtain a white solid; vacuum drying the white solid for 4h to obtain beta-cyclodextrin and tea tree essential oil clathrate (see fig. 2, fig. 4 and fig. 6). The inclusion rate was 72.56%, and the yield was 87.68%.
Example 2
A method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method comprises the following steps:
(1) Dissolving 50g (0.044 mol) of recrystallized beta-cyclodextrin in 1500mL of alkaline electrolyzed water with pH =11 to obtain a solution I; 44.13g (0.0616 mol) of tea tree essential oil is dissolved in 17g (0.3696 mol) of absolute ethyl alcohol to obtain a solution II;
(2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 55 ℃ for 5 hours to obtain emulsion; adjusting the temperature to room temperature, standing for 36h, filtering, washing a filter cake with absolute ethyl alcohol, removing unreacted tea tree essential oil and impurities, and performing suction filtration to obtain a white solid; and (3) drying the white solid in vacuum for 5 hours to obtain the beta-cyclodextrin and tea tree essential oil inclusion compound. The clathration rate is 70.86% and the yield is 87.98%.
In this example, a tea tree essential oil was replaced with a jasmine essential oil or a rose essential oil, and in the same manner as in this example, a beta-cyclodextrin and jasmine essential oil inclusion compound or a beta-cyclodextrin and rose essential oil inclusion compound was prepared, which had an inclusion rate and a yield similar to those of the product obtained in this example.
Example 3
A method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method comprises the following steps:
(1) Dissolving 40g (0.035 mol) of recrystallized beta-cyclodextrin in 1600mL of alkaline electrolyzed water with pH =12 to obtain a first solution; dissolving 40.12g (0.056 mol) of tea tree essential oil in 23.18g (0.504 mol) of absolute ethyl alcohol to obtain a solution II;
(2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 75 ℃ for 3 hours to obtain emulsion; adjusting the temperature to room temperature, standing for 48h, filtering, washing a filter cake with absolute ethyl alcohol, removing tea tree essential oil and impurities which are not completely reacted, and performing suction filtration to obtain a white solid; and (3) drying the white solid in vacuum for 6 hours to obtain the beta-cyclodextrin and tea tree essential oil inclusion compound. The inclusion rate was 54.35%, and the yield was 80.26%.
The above description is only for illustrative purposes and is not intended to be construed as limiting the scope of the invention, and all equivalent changes, modifications, or equivalent arrangements or changes in size or dimensions that are not necessarily required to practice the invention are intended to be included therein.
Claims (4)
1. A method for preparing beta-cyclodextrin and essential oil inclusion compound by an alkaline electrolytic water method is characterized by comprising the following steps:
(1) Dissolving the recrystallized beta-cyclodextrin in alkaline electrolyzed water with the pH =10-12 to obtain a solution I; dissolving the essential oil in absolute ethyl alcohol to obtain a solution II;
(2) Dropwise adding the solution I into the solution II under stirring, and reacting in a constant-temperature water bath at 20-75 ℃ for 3-7h to obtain emulsion; adjusting the temperature to room temperature, standing for 24-48h, filtering, washing a filter cake with absolute ethyl alcohol, and performing suction filtration to obtain a white solid; vacuum drying the white solid for 4-6h to obtain beta-cyclodextrin and essential oil clathrate;
the ratio of the beta-cyclodextrin to alkaline electrolyzed water with pH =10-12 is 1g (20 mL-40 mL).
2. The method as set forth in claim 1, wherein the mass ratio of the absolute ethanol to the essential oil is 1 (1.7-5.2).
3. The method as set forth in claim 1, wherein the mass ratio of the essential oil to the beta-cyclodextrin is 1 (0.997-1.58).
4. A process according to claim 1, 2 or 3, wherein the essential oil is tea tree essential oil, jasmine essential oil or rose essential oil.
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