CN106370494A - Method for extracting and separating coumarin by utilizing [BuPy(Butyl Pyridine)] PF6 - Google Patents
Method for extracting and separating coumarin by utilizing [BuPy(Butyl Pyridine)] PF6 Download PDFInfo
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- CN106370494A CN106370494A CN201610888678.7A CN201610888678A CN106370494A CN 106370494 A CN106370494 A CN 106370494A CN 201610888678 A CN201610888678 A CN 201610888678A CN 106370494 A CN106370494 A CN 106370494A
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- Prior art keywords
- coumarin
- bupy
- ionic liquid
- butyl
- liquid
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 229960000956 coumarin Drugs 0.000 title claims abstract description 67
- 235000001671 coumarin Nutrition 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 25
- ADSOSINJPNKUJK-UHFFFAOYSA-N 2-butylpyridine Chemical compound CCCCC1=CC=CC=N1 ADSOSINJPNKUJK-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002608 ionic liquid Substances 0.000 claims abstract description 68
- 238000000605 extraction Methods 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 11
- 239000012488 sample solution Substances 0.000 claims abstract description 11
- 238000005303 weighing Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000007865 diluting Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000000523 sample Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 238000002137 ultrasound extraction Methods 0.000 claims abstract description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 claims abstract 2
- 239000007788 liquid Substances 0.000 claims description 28
- -1 n- butyl-pyridinium hexafluorophosphate Chemical compound 0.000 claims description 24
- 238000002835 absorbance Methods 0.000 claims description 17
- 239000008346 aqueous phase Substances 0.000 claims description 17
- 239000000284 extract Substances 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 9
- 230000009514 concussion Effects 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 238000002798 spectrophotometry method Methods 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 4
- 238000005893 bromination reaction Methods 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000005086 pumping Methods 0.000 claims description 3
- 238000002390 rotary evaporation Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000013517 stratification Methods 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 6
- 241000522215 Dipteryx odorata Species 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005452 bending Methods 0.000 description 3
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 150000001768 cations Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PKRPFNXROFUNDE-LLVKDONJSA-N Byakangelicin Chemical compound O1C(=O)C=CC2=C1C(OC[C@@H](O)C(C)(C)O)=C1OC=CC1=C2OC PKRPFNXROFUNDE-LLVKDONJSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 101710094902 Legumin Proteins 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- NEKNNCABDXGBEN-UHFFFAOYSA-L disodium;4-(4-chloro-2-methylphenoxy)butanoate;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O.[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl NEKNNCABDXGBEN-UHFFFAOYSA-L 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229940046010 vitamin k Drugs 0.000 description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- 241000213006 Angelica dahurica Species 0.000 description 1
- 240000002514 Cymbidium ensifolium Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 241001473382 Trilisa odoratissima Species 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 102000004210 Vitamin K Epoxide Reductases Human genes 0.000 description 1
- 108090000779 Vitamin K Epoxide Reductases Proteins 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003698 antivitamin K Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000680 avirulence Effects 0.000 description 1
- PKRPFNXROFUNDE-UHFFFAOYSA-N biac-angelicin Natural products O1C(=O)C=CC2=C1C(OCC(O)C(C)(C)O)=C1OC=CC1=C2OC PKRPFNXROFUNDE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- OLOOJGVNMBJLLR-UHFFFAOYSA-N imperatorin Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OCC=C(C)C OLOOJGVNMBJLLR-UHFFFAOYSA-N 0.000 description 1
- XKVWLLRDBHAWBL-UHFFFAOYSA-N imperatorin Natural products CC(=CCOc1c2OCCc2cc3C=CC(=O)Oc13)C XKVWLLRDBHAWBL-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940019333 vitamin k antagonists Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a method for extracting and separating coumarin by utilizing [BuPy(Butyl Pyridine)] PF6. The method comprises the following steps: weighing and putting 20g of radix angelicae dahurioae sample powder in a 50mL of conical flask with a cover, accurately weighing and adding 25mL of methyl alcohol in the conical flask, weighing, carrying out ultrasonic extraction for one hour, compensating the weight and weighing after taking the mixture out and cooling to room temperature, shaking well, and filtering, thus obtaining a sample solution; adding 10mL of the sample solution in a colorimetric tube, then adding 0.6g of the [BuPy]PF6, heating, oscillating and standing, taking out 1mL of water phase, diluting to consistent volume, and measuring absorbancy in a 278nm wavelength position by using an ultraviolet-visual spectrophotometer; determining the concentration of the coumarin according to a made standard working curve. According to the method disclosed by the invention, the [BuPy]PF6 is used as an extracting agent for extracting and separating the active component-coumarin in radix angelicae dahurioae, the extraction rate of the coumarin is up to 92.05 percent, the mass concentration of the coumarin is determined by adopting ultraviolet spectroscopy, and the influence of factors such as the extraction time, the PH (Potential of Hydrogen) value, the mass concentration of the coumarin and the dosage of ionic liquid on the extraction effect is investigated.
Description
Technical field
The present invention relates to a kind of utilize n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method.
Background technology
Ionic liquid has as the possible of alternative volatile organic solvent and is found in multiple research fields and has perhaps
Many applications, the nearest appearance of ionic liquid as " green " and environmentally friendly solvent chemical industry production in made
With.Come in the past few decades, ionic liquid is gradually available in different applications, seems: organic synthesiss, catalytic electrochemical device
Extraction with the various compound of solvent.Ionic liquid be developed using the advantage being because physicochemical property that it has, such as:
Vapour pressure, high heat stability and electrochemical stability, high-solvency etc., the selection of ionic liquid cationic and anion
Composition in physical property, there is profound influence, such as density, viscosity, electrical conductivity and polarity.Ionic liquid has very in performance
Big motility, because the composition of cation and anion is at a relatively high, however, the extensive and classification of cation and anion makes conjunction
Become research extremely difficult.A suitable ionic liquid is selected to need the comprehensive of a fundamental property for a specific application program
Close data base, such as, the stability of the ionic liquid in wide range, density, these data such as viscosity and compatibility, ion
Liquid can be gone to provide some comparable performances by circulation in chemical reaction.
Ionic liquid is found to have an optimistic view of in many organic reactions, such as diels-Alder, bail-Harry Hillman, and He Ke is anti-
Should, esterification, in isomerization reaction and many coupling reactions, pressure, the progress of temperature and reactant concentration control reaction, from
Sub- liquid can be that very effective solvent medium obtains optimal output with minimum possible environmental pollution in some applications,
Because these some advantages of ionic liquid, people increasingly can modify ionic liquid and programmable function as one kind
Type molecule, conveniently obtains more using values from this novel dissolvent, here it is described functional type ionic liquid, refers to
Ionic liquid containing functional group in ion (anion or cation), but ionic liquid and functional group must be seen as one not
Alienable entirety [3].In functional type ionic liquid, ionic liquid and functional group all there occurs that significantly property changes, example
As participated in impact reaction as reagent, solvent, carrier or catalyst in organic solvent.
Go deep into to ionic liquid work studieies, ionic liquid is carried out functionalization, not only can enrich ion
The multiformity of class of liquids, can also impart to the special chemistry of ion special body size, physical property, is also greatly expanded its application
Field.The research of functionalized ion liquid, can be important directions studying field of ionic liquid in the future.But at present, have
The further investigation report closing this kind of ionic liquid chemical physical property is few, and relevant n- butyl-pyridinium hexafluorophosphate work(
The research of the performance and extraction application that can change ionic liquid has no report.So, synthesize n- butyl-pyridinium hexafluorophosphoric acid herein
Functionalized ion liquid, is studied to its Partial Physical Property and structure composition, and has been inquired into as extractant pair
The extraction ability of coumarin.
Coumarin, English name is coumarin, molecular formula: c9h6o2, relative molecular weight 146.15, and white crystals are solid
Body, 68～70 DEG C of fusing point, 298 DEG C/266pa of boiling point, relative density 0.9350.Natural discovery be present in tonka beans, Liatris odoratissima,
In wild vanilla, Cymbidium ensifolium (L.) Sw., there is fresh Radix Glycyrrhizae perfume and tonkabean is fragrant, typically do not make edible it is allowed to cigarette is used and external [4].Coumarin
The effect of class medicine be anticoagulant the factor liver synthesis, Coumarinses medicine is similar to the structure of vitamin k, coumarin
Class medicine is combined with vitamin k epoxide reductase in liver, and suppression vitamin k is converted from epoxide to hydroquinone type, dimension
The circulation of raw element k is suppressed it may be said that Coumarinses medicine is vitamin k antagonist, or competitive inhibitor [5].
At present, the extracting method of the coumarin of commercial Application remains traditional solvent extraction.Patent
Cn200510013353.6 discloses a kind of supercritical extraction process method of Radix Angelicae Dahuricae oleoresin, and its advantage is to avoid organic solvent
Residual.Because in Radix angelicae dahuricae medical material, coumarin kind compound content is very low, only 0.1% about, single extracting method is often
The gratifying separating effect of difficult to reach, therefore, various complex technologys are increasingly paid attention to.Patent cn200710079571.9
A kind of extraction method of dahurian angelica root coumarin is disclosed, and by the Radix Angelicae Dahuricae with alcohol reflux, extracting solution, after filtration, concentration, precipitate with ethanol, uses stone
Oily ether and chloroform are extracted.Patent cn200710019809.9 is proposed using solvent and macroporous resin combined process prepares the Radix Angelicae Dahuricae
Annoying coumarin extract.Patent cn200810200253.8 disclose a kind of from the methanol extraction Radix Angelicae Dahuricae, then with macroporous resin with
High performance preparative liquid chromatography isolates and purifies imperatorin therein and byak-angelicin.Above-mentioned Technology respectively has speciality, but exists
That complex process, production cost be high and the problems such as pollution environment it is difficult to industrialized application.
Content of the invention
For the problems referred to above, the invention provides a kind of utilize n- butyl-pyridinium hexafluorophosphate extract and separate coumarin side
Method.
For solving above-mentioned technical problem, the technical solution adopted in the present invention is: one kind utilizes n- butyl-pyridinium hexafluoro phosphorus
Hydrochlorate extract and separate coumarin method, adds the n- butyl-pyridinium six of a certain amount of volume in coumarin aqueous solution (0.01g/l)
Fluorophosphate [bupy] pf6Ionic liquid, heating concussion in temperature chamber (80 DEG C), stratification, cooling, after being extracted
Aqueous phase and ionic liquid body phase, finally adopt the content of coumarin in Water by Ultraviolet Spectrophotometry phase.
Further, a length of 278nm of the maximum absorption wave of described coumarin.
Further, described extraction time is 10 minutes.
Further, described coumarin mass concentration is 0.02g/l.
Further, described n- butyl-pyridinium hexafluorophosphate [bupy] pf6The consumption 0.6g of ionic liquid.
Further, described n- butyl-pyridinium hexafluorophosphate [bupy] pf6The preparation method of ionic liquid is following walking
Rapid:
(a), the bromination of n-butane accurately weighing 136.9996g (0.5mol) with electronic balance and 76.8276g (0.5mol)
Pyridine add 250ml three-neck flask in, be subsequently adding 20ml hexamethylene, mechanical agitation 20h under 65 DEG C of heating in water bath, obtain
To lower floor's yellow liquid, upper strata milky white liquid, inclined in upper strata, the temperature of Rotary Evaporators is set as 90 DEG C, and here
At a temperature of lower floor's liquid evaporated in Rotary Evaporators 2h, the solid obtaining is faint yellow, then is washed with ethyl acetate (50ml)
Wash three times, be put in vacuum drying oven and 24h be dried at a temperature of 60 DEG C, obtaining 114.8441g faint yellow solid is middle producing
Thing, yield is 96.200%；
(b), accurately weigh the intermediate product and 45.0200 of 43.0400g in step (a) (0.2mol) with electronic balance
(0.2mol) Potassium Hexafluorophosphate, in round-bottomed flask, adds 50ml acetone, stirs in digital display thermostat water bath under 30 DEG C of heating
Mix 24h, sucking filtration, obtain upper strata white solid, take off metafiltration liquid rotary evaporation at 50 DEG C, after cooling, obtain white solid powder
End, is washed three times with distilled water (50ml), pumping rate, then puts it into 24h (temperature be 50 DEG C) is dried in just empty drying baker, obtains final product
White powder ionic liquid [bupy] pf to 40.7505g6, yield is 92.4667%.
Further, 7, described one kind utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be, comprise the steps:
(1) configure sample solution: weigh Radix Angelicae Dahuricae sample powder 0.2g, be placed in 50ml conical flask with cover, accurately measure
25ml methanol is added to conical flask, weighs, and (about 25 DEG C) ultrasonic extraction 1h, treats after taking-up that it is cooled to room temperature at room temperature
Afterwards, mend and weigh again, shake up, filter, that is, obtain sample solution；
(2) measure the content of coumarin aqueous solution: add the sample solution of 10ml in color comparison tube, be subsequently adding 0.6g's
N- butyl-pyridinium hexafluorophosphate [bupy] pf6Ionic liquid, stands after heating concussion in temperature chamber (80 DEG C), takes out 1ml
Aqueous phase, is placed in 50ml volumetric flask, plus distilled water diluting constant volume, with measuring at 278nm wavelength on spectrophotometry instrument
Corresponding absorbance；By the standard working curve made, abscissa is the concentration of coumarin, and vertical coordinate is absorbance, root
To determine the concentration of coumarin according to absorbance.
From the above-mentioned description to present configuration, compared to the prior art, the present invention has the advantage that
1 by the present invention in that send out the content measuring coumarin, traditional liquid chromatograph etc. with other with uv-spectrophotometric
Method compares, simple, and the concentration range being suitable for is wider.
2nd, the present invention have studied ionic liquid [bupy] pf6Consumption to during the experiment of the impact of extraction yield, result shows,
Even if adding little [bupy] pf6Ionic liquid, (m=0.6g extraction yield is up to also to reach very high extraction yield
99.025%).
3rd, the present invention [bupy] pf6 ion liquid abstraction coumarin, its extraction yield reaches as high as 99%, and does not need
Add other extractants it is possible to [bupy] pf6Ionic liquid is used for extracting directly as extractant.
4th, the open loop closed loop conversion by coumarin for the present invention, effectively from ionic liquid, coumarin is taken out in back extraction, real
The recovery of coumarin and recycling of ionic liquid are showed.
5th, the present invention passes through to adopt [bupy] pf6Coumarin in the ionic liquid extract Radix Angelicae Dahuricae, because ionic liquid has
Low volatility, low solvent borne, avirulence, pollution-free, to multiple properties such as thermally-stabilised, therefore its extraction process environmentally safe
While environmental protection, can by environmental factorss and economic factor be incorporated into one, realize sustainable development.
Brief description
The accompanying drawing constituting the part of the application is used for providing a further understanding of the present invention, the schematic reality of the present invention
Apply example and its illustrate, for explaining the present invention, not constituting inappropriate limitation of the present invention.In the accompanying drawings:
Fig. 1 is the maximum absorption wavelength curve chart of coumarin；
Fig. 2 is the working curve diagram of coumarin；
Fig. 3 is the impact result figure to extraction yield for the buffer solution of ph value；
Fig. 4 is the impact result figure to extraction yield for the extraction time；
Fig. 5 is the impact result figure to extraction yield for the coumarin mass concentration；
Fig. 6 is [bupy] pf6The impact result figure to extraction yield for the ionic liquid consumption；
Fig. 7 is [bupy] pf6The infrared spectrogram of ionic liquid.
Specific embodiment
In order that the objects, technical solutions and advantages of the present invention become more apparent, below in conjunction with drawings and Examples, right
The present invention is further elaborated.It should be appreciated that specific embodiment described herein is only in order to explain the present invention, and
It is not used in the restriction present invention.
Embodiment 1: using n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method
1st, instrument, reagent
(1) instrument: hh-4 digital display thermostat water bath (Guo Hua Electrical Appliances Co., Ltd), electronic balance ar224cn (Ao Haosi instrument
The manufacture of device (Shanghai) Co., Ltd., Rotary Evaporators (Zhengzhou Greatwall Scientific Industrial ＆ Trading Co., Ltd.), shz-d circulating water type vacuum pump
(it is limited that the U.S. spectrum in Shanghai reaches instrument for (Zi Hua instrument Co., Ltd of Gongyi City), u8-1800pc type ultraviolet-uisible spectrophotometer
Company), dzf 6050 vacuum drying oven (upper Nereid's grand experimental facilitiess company limited), avatar360fi-ir fourier infrared
(upper Nereid is grand for spectrogrph (U.S.), wrs-1 type numeral melting point instrument (Shanghai physico-optical instrument), dzf 6050 vacuum drying oven
Experimental facilitiess company limited), tc-15 shell type thermostat (Zhejiang Xinhua medical apparatus and instruments factory), kq-200kde ultrasonic washing unit
(Gu Deng industry (Shanghai) Co., Ltd.).
(2) reagent: pyridine (development in science and technology company limited is recovered in Tianjin)；(western Gansu Province chemical industry share is limited for bromination of n-butane
Company)；Ethyl acetate (ar), analysis is pure；Hexamethylene；Acetone；Potassium Hexafluorophosphate；Coumarin, analysis is pure, coumarin needs heat
Water hydrotropy；The Radix Angelicae Dahuricae；Methanol.
2nd, test method and result
Test method: [bupy] pf6Coumarin in the ion liquid abstraction Radix Angelicae Dahuricae and fragrant with determined by ultraviolet spectrophotometry
The method of the content of legumin
(1) configure sample solution: weigh Radix Angelicae Dahuricae sample powder 0.2g, be placed in 50ml conical flask with cover, accurately measure
25ml methanol is added to conical flask, weighs, and (about 25 DEG C) ultrasonic extraction 1h, treats after taking-up that it is cooled to room temperature at room temperature
Afterwards, mend and weigh again, shake up, filter, that is, obtain sample solution；
(2) measure the content of coumarin aqueous solution: add the sample solution of 10ml in color comparison tube, be subsequently adding 0.6g's
N- butyl-pyridinium hexafluorophosphate [bupy] pf6Ionic liquid, stands after heating concussion in temperature chamber (80 DEG C), takes out 1ml
Aqueous phase, is placed in 50ml volumetric flask, plus distilled water diluting constant volume, with measuring at 278nm wavelength on spectrophotometry instrument
Corresponding absorbance；By the standard working curve made, abscissa is the concentration of coumarin, and vertical coordinate is absorbance, root
To determine the concentration of coumarin according to absorbance.
Based in this approach, determine the determination of the maximum absorption wavelength of coumarin, and it is molten to study the buffering of different ph values
Liquid, extraction time, coumarin mass concentration and [bupy] pf6The shadow to extraction yield, stripping rate for the factors such as ionic liquid consumption
Ring, to draw optimal conditionss.
Result and discussion:
(1) determination of coumarin maximum absorption wavelength
Using distilled water as reference, it is to scan (0.01g/l) under 200-320nm in the wave-length coverage of ultraviolet spectrophotometer
The ultra-violet absorption spectrum (light path of cuvette is 1cm) of aqueous phase after coumarin aqueous solution and extraction, and determine the maximum suction of coumarin
Receive wavelength, as described in Figure 1, result shows result, and in this experiment, absorbance at 278nm for the coumarin is maximum, because
This, a length of 278nm of maximum absorption wave of coumarin.
Make the perfume (or spice) that mass concentration is 0.001g/l, 0.0025g/l, 0.005g/l, 0.0075g/l, 0.01g/l respectively
Legumin aqueous solution, then using distilled water as reference, measuring maximum absorption wavelength 278nm, measuring the tonkabean of variable concentrations respectively
The absorbance of plain aqueous solution, determines regression equation according to the relation of coumarin aqueous solution mass concentration and absorbance, result such as Fig. 2
Described, result shows, in this experiment, absorbance is proportional with concentration, and with absorbance as abscissa, concentration is vertical seat
Mark, draws out standard curve and can calculate regression equation and be: y=0.0219 × x+0.0873r=0.99242, according to this time
Return equation and sampling amount, you can calculate the content of coumarin.
(2) impact to extraction yield for the buffer solution methanol of different ph values
Add the coumarin aqueous solution of 10ml (0.01g/l) in different color comparison tubes, and be separately added into 3ml difference ph's
Buffer solution methanol, is subsequently adding [bupy] pf of equivalent6Ionic liquid, in temperature chamber (80 DEG C), heating concussion is then quiet
Put, take out the aqueous phase after 1ml extraction after cooling and be placed in 50ml volumetric flask, and add distilled water diluting constant volume, after measuring dilution
Aqueous phase absorbance simultaneously calculates extraction yield, and as described in Figure 3, result shows result, in this experiment, [bupy] pf6To tonkabean in water
The change in acidity and alkaline environment of the extraction yield of element is little, and this is because in the range of ph value, coumarin is relatively stable,
Both do not change coumarin electriferous state, do not change its structure yet, and because coumarin aqueous solution itself is close neutral, therefore
Extracting selected ph value is 7, that is, neutral environment is it is not necessary to be adjusted to ph.
(3) impact to extraction yield for the extraction time
Measure 10ml coumarin aqueous solution (0.01g/l) in color comparison tube, add a certain amount of [bupy] pf6Ionic liquid
Body, in temperature chamber (80 DEG C), heating concussion and then standing, often take out 1ml aqueous phase at regular intervals, are placed in 50ml volumetric flask
In, plus distilled water diluting constant volume, the absorbance of aqueous phase calculate extraction yield after measuring dilution.As described in Figure 4, result shows result
Show, in this experiment, in 1-10min, extraction yield increase over time significantly raised, after 10min arrive 20min, with
The prolongation of time, extraction yield is gradually walked straight to constant, now, has reached maximum extraction rate, and biphase to have reached distribution flat
Weighing apparatus, therefore, the extraction yield highest in 10min, preferably, extraction time should elect 10 minutes as to effect of extracting.
(4) impact to extraction yield for the coumarin mass concentration
The coumarin aqueous solution for 0.01g/l, 0.02g/l, 0.03g/l, 0.04g/l for the concentration is separately added into color comparison tube
In, and add [bupy] pf of equivalent6Ionic liquid, heating concussion and then standing in temperature chamber (80 DEG C), take out 1ml respectively
Aqueous phase, is placed in 50ml volumetric flask, plus distilled water diluting constant volume, the absorbance of aqueous phase calculate extraction yield after measuring dilution.Knot
As described in Figure 5, result shows fruit, in this experiment, as seen from the figure, with the increase of coumarin aqueous solution mass concentration, ion
Liquid also constantly raises to its extraction yield, because the water solublity of coumarin aqueous solution is poor, this experiment coumarin used
Mass concentration less, in little concentration more, sample may also be far from reaching balance, so extraction yield is smaller, and
In the mass concentration of 0.02g/l, extraction yield has reached 94.05%, then the increase with concentration, and extraction yield no longer substantially rises
Height, so, extract optimum coumarin mass concentration 0.02g/l.
(5)[bupy]pf6The impact to extraction yield for the ionic liquid consumption
Add the coumarin aqueous solution of 10ml0.01g/l in different color comparison tubes, and be separately added into different volumes ion
Liquid, in constant temperature (80 DEG C), heating concussion and then standing, take out 1ml aqueous phase respectively, are placed in 50ml volumetric flask, plus distilled water
Dilution constant volume, the absorbance of aqueous phase calculate extraction yield after measuring dilution.As described in Figure 6, result shows result, in this experiment
In, as seen from the figure, with the increase of ionic liquid consumption, extraction yield is gradually increased, when ionic liquid consumption is 0.6g, extraction
Rate highest, so [bupy] pf6The consumption of ionic liquid should elect 0.6g as.
Embodiment 2:[bupy] pf6The back extraction of ionic liquid
Ionic liquid aqueous phase in color comparison tube after extraction is poured out, organic with the ionic liquid of solid-state separated, with three times
Ionic liquid organic faciess after the 1.o mol/l naoh solution washing extraction of amount, then ion is detected by ultra-violet absorption spectrum
Liquid, can't detect the residual having coumarin in ionic liquid, the aqueous phase after washing is acidified with hydrochloric acid, can retrieve tonkabean
Element, response rate yield 93.2%.
Embodiment 3:n- butyl-pyridinium hexafluorophosphate [bupy] pf6The preparation of ionic liquid and characteristic present
1st, n- butyl-pyridinium hexafluorophosphate [bupy] pf6The synthetic route of ionic liquid
2、[bupy]pf6The concrete synthesis step of ionic liquid is as follows:
(a), the bromination of n-butane accurately weighing 136.9996g (0.5mol) with electronic balance and 76.8276g (0.5mol)
Pyridine add 250ml three-neck flask in, be subsequently adding 20ml hexamethylene, mechanical agitation 20h under 65 DEG C of heating in water bath, obtain
To lower floor's yellow liquid, upper strata milky white liquid, inclined in upper strata, the temperature of Rotary Evaporators is set as 90 DEG C, and here
At a temperature of lower floor's liquid evaporated in Rotary Evaporators 2h, the solid obtaining is faint yellow, then is washed with ethyl acetate (50ml)
Wash three times, be put in vacuum drying oven and 24h be dried at a temperature of 60 DEG C, obtaining 114.8441g faint yellow solid is middle producing
Thing, yield is 96.200%；
(b), accurately weigh the intermediate product and 45.0200 of 43.0400g in step (a) (0.2mol) with electronic balance
(0.2mol) Potassium Hexafluorophosphate, in round-bottomed flask, adds 50ml acetone, stirs in digital display thermostat water bath under 30 DEG C of heating
Mix 24h, sucking filtration, obtain upper strata white solid, take off metafiltration liquid rotary evaporation at 50 DEG C, after cooling, obtain white solid powder
End, is washed three times with distilled water (50ml), pumping rate, then puts it into 24h (temperature be 50 DEG C) is dried in just empty drying baker, obtains final product
White powder ionic liquid [bupy] pf to 40.7505g6, yield is 92.4667%.
3rd, n- butyl-pyridinium hexafluorophosphate [bupy] pf6The characteristic present of ionic liquid
By synthesized final product [bupy] pf6Ionic liquid carries out infrared spectrum sign, and its characterization result is shown in Fig. 7.
The absworption peak explanation sample of 3423.25cm-1 causes o h stretching vibration due to absorbing a small amount of moisture content；
3145.81cm-1 and 3105.96cm-1 is due to the c h stretching vibration on ring；2972.28cm-1 is that the c h of ch3 is not right
Claim flexible peak；2882.69cm-1 is the c h symmetrically flexible peak of ch3；1638.30cm-1 being the stretching vibration peak of c=n,
1505.18cm-1 and 1470.77cm-1 illustrates that this compound contains pyridine ring；1489.33cm-1 being that in pyridine ring, c=n stretches
Vibration peak；1456.92cm-1 is the asymmetric vibration peak of bending of ch3；1173.53cm-1 being c h in-plane bending vibration peak；
And 685.51cm-1 is c h out-of-plane bending vibration peak；782.91cm-1 is because on pyridine ring, c=c flexural vibrations peak causes
's.In addition, passing through consulting literatures [11], this two absworption peaks of 834.27cm-1,556.98cm-1 are all pf6- peculiar.Knot
As described in Figure 7, result shows fruit, and synthesized final product is [bpy] pf6 ionic liquid.
4th, ionic liquid [bupy] pf6Fusing point
The ionic liquid of synthesis is white powder at normal temperatures, is in liquid, needs ion when therefore extracting under high temperature
Liquid is heated to melting, then is extracted, and such as shown in table 1 (the melting point data table of [bupy] pf6), the just fusing point of ionic liquid is big
About at 63.4 DEG C, and melt at 67.3 DEG C about eventually.
| Sequence number | 1 | 2 | 3 |
| Incipient melting DEG C | 63.3 | 63.5 | 63.4 |
| Molten DEG C eventually | 67.2 | 67.4 | 67.1 |
Described in result table 1, fusing point spacing is big, illustrates that ionic liquid is impure, result shows, in this experiment, synthesis from
Sub- liquid [bupy] pf6Purity high.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention
Any modification, equivalent and improvement made within god and principle etc., should be included within the scope of the present invention.
Claims (7)
1. a kind of using n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method it is characterised in that: water-soluble in coumarin
N- butyl-pyridinium hexafluorophosphate [bupy] pf of a certain amount of volume is added in liquid (0.01g/l)6Ionic liquid, in temperature chamber
Heating concussion in (80 DEG C), stratification, cooling, the aqueous phase after being extracted and ionic liquid body phase, finally adopt ultraviolet spectrometry
The content of coumarin in spectrphotometric method for measuring aqueous phase.
2. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be: a length of 278nm of maximum absorption wave of described coumarin.
3. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be: described extraction time is 10 minutes.
4. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be: described coumarin mass concentration is 0.02g/l.
5. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be: described n- butyl-pyridinium hexafluorophosphate [bupy] pf6The consumption 0.6g of ionic liquid.
6. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be: described n- butyl-pyridinium hexafluorophosphate [bupy] pf6The preparation method of ionic liquid is following steps:
The pyrrole of (a), the bromination of n-butane accurately weighing 136.9996g (0.5mol) with electronic balance and 76.8276g (0.5mol)
Pyridine adds in the three-neck flask of 250ml, is subsequently adding 20ml hexamethylene, mechanical agitation 20h under 65 DEG C of heating in water bath, under obtaining
Layer yellow liquid, upper strata milky white liquid, inclined in upper strata, the temperature of Rotary Evaporators is set as 90 DEG C, and in this temperature
Lower lower floor's liquid is evaporated in Rotary Evaporators 2h, the solid obtaining is faint yellow, then washs three with ethyl acetate (50ml)
Secondary, it is put in vacuum drying oven and 24h is dried at a temperature of 60 DEG C, obtaining 114.8441g faint yellow solid is intermediate product, produce
Rate is 96.200%；
(b), accurately weigh the intermediate product and 45.0200 of 43.0400g in step (a) (0.2mol) with electronic balance
(0.2mol) Potassium Hexafluorophosphate, in round-bottomed flask, adds 50ml acetone, stirs in digital display thermostat water bath under 30 DEG C of heating
Mix 24h, sucking filtration, obtain upper strata white solid, take off metafiltration liquid rotary evaporation at 50 DEG C, after cooling, obtain white solid powder
End, is washed three times with distilled water (50ml), pumping rate, then puts it into 24h (temperature be 50 DEG C) is dried in just empty drying baker, obtains final product
White powder ionic liquid [bupy] pf to 40.7505g6, yield is 92.4667%.
7. one kind according to claim 1 utilizes n- butyl-pyridinium hexafluorophosphate extract and separate coumarin method, and it is special
Levy and be, comprise the steps:
(1) configure sample solution: weigh Radix Angelicae Dahuricae sample powder 0.2g, be placed in 50ml conical flask with cover, accurately measure 25ml first
Alcohol is added to conical flask, weighs, and (about 25 DEG C) ultrasonic extraction 1h, is cooled to after room temperature after it after taking-up at room temperature, mends weight
Weigh, shake up, filter, that is, obtain sample solution；
(2) measure the content of coumarin aqueous solution: add the sample solution of 10ml in color comparison tube, be subsequently adding the n- fourth of 0.6g
Yl pyridines hexafluorophosphate [bupy] pf6Ionic liquid, stands after heating concussion in temperature chamber (80 DEG C), takes out 1ml aqueous phase,
It is placed in 50ml volumetric flask, plus distilled water diluting constant volume, corresponded at 278nm wavelength with measuring on spectrophotometry instrument
Absorbance；By the standard working curve made, abscissa is the concentration of coumarin, and vertical coordinate is absorbance, according to suction
Shading value is determining the concentration of coumarin.
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