CN104119904B - P-coumaric acid-LEuH complex body and synthetic method thereof - Google Patents

P-coumaric acid-LEuH complex body and synthetic method thereof Download PDF

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CN104119904B
CN104119904B CN201410295668.3A CN201410295668A CN104119904B CN 104119904 B CN104119904 B CN 104119904B CN 201410295668 A CN201410295668 A CN 201410295668A CN 104119904 B CN104119904 B CN 104119904B
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leuh
coumaric acid
complex body
synthetic method
water
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CN104119904A (en
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马淑兰
谷庆阳
苏飞飞
马腾
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Beijing Normal University
Beijing Normal University Science Park Technology Development Co Ltd
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Beijing Normal University
Beijing Normal University Science Park Technology Development Co Ltd
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Abstract

The embodiment of the invention discloses a kind of P-coumaric acid-LEuH complex body and synthetic method thereof, this complex body has following chemical formula composition: Eu (OH) 2.4(C 9h 6o 3) 0.31.33H 2o.P-coumaric acid and stratiform europium oxyhydroxide LEuH utilize ion exchange method to synthesize P-coumaric acid-LEuH complex body by the present invention.After forming complex body, because P-coumaric acid is to Eu in LEuH 3+the cancellation effect of fluorescence, thus, the fluorescent characteristic of LEuH and P-coumaric acid-LEuH complex body shows larger difference.The difference of this fluorescent characteristic is utilized indirectly to detect P-coumaric acid.

Description

P-coumaric acid-LEuH complex body and synthetic method thereof
Technical field
The present invention relates to organic synthesis field, particularly P-coumaric acid-LEuH complex body and synthetic method thereof.
Background technology
P-coumaric acid (Naringeninic acid) is that one has bioactive organic phenolic acid, and it is mainly present in leguminous plants, can be widely used in the fields such as medicine, agricultural, chemical industry.In medical, P-coumaric acid has anticancer, antitumor action, and has provide protection to the mutagenesis of liver and oxidative damage.In addition, it or the important intermediate of some drug manufacture, can be used to prepare narcotic, sterilant and hemostatic agent.Agriculturally, P-coumaric acid may be used for producing plant growth promoter, sterilant and fruit and vegetable fresh-keeping agent etc.In chemical industry, the intermediate that P-coumaric acid can be produced as essence and flavoring agent, is also often used in electronic material due to its electroconductibility.
From the above, P-coumaric acid is a kind of very important organic compound, therefore, how detects it and just becomes a very important problem.
Summary of the invention
For solving the problem, the embodiment of the invention discloses P-coumaric acid-LEuH complex body and synthetic method thereof; Technical scheme is as follows:
P-coumaric acid-LEuH complex body, has following chemical formula composition:
Eu(OH) 2.4(C 9H 6O 3) 0.3·1.33H 2O。
Use X-ray diffractometer to test the X-ray diffractogram obtaining described complex body to this complex body, wherein, the pass at spacing d and θ angle, Prague 2 is:
Use infrared spectrometer to test the infrared spectra obtaining described complex body to this complex body, wherein, the wave number of the charateristic avsorption band in infrared spectra is respectively: 3423 (cm -1), 1630 (cm -1), 1593 (cm -1), 1508 (cm -1), 1429 (cm -1), 1384 (cm -1), 980 (cm -1), 836 (cm -1) and 566 (cm -1).
The present invention discloses a kind of synthetic method of P-coumaric acid-LEuH complex body, comprise the following steps:
A) be scattered in water by LEuH, then add P-coumaric acid sodium-salt aqueous solution, obtain mixed solution, wherein, the mol ratio of LEuH and P-coumaric acid sodium salt is: 1:(2-9);
B) by described mixed solution at 40-120 DEG C, hydro-thermal reaction 12-24 hour at preferred 70-100 DEG C, reaction terminates to carry out aftertreatment to obtained product afterwards.
Wherein, the synthetic method of described P-coumaric acid sodium-salt aqueous solution is: by P-coumaric acid and NaOH soluble in water obtained.
In the preferred embodiment of the present invention, the mol ratio of described P-coumaric acid and NaOH is: 1:(1.5-2.5).
In the preferred embodiment of the present invention, the mol ratio of described LEuH and P-coumaric acid sodium salt is: 1:(3-6).
In the preferred embodiment of the present invention, described aftertreatment comprises: filtration, washing, drying.
In the preferred embodiment of the present invention, the synthetic method of described LEuH is:
By Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is soluble in water, obtain the aqueous solution, then in obtained aqueous solution, pass into N 23-10 minute, carries out hydro-thermal reaction 12-18h at 70-100 DEG C, and reaction terminates rear to the filtration of obtained product, washing, drying;
Wherein, Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine mol ratio be: 1:(10-15): (0.5-1.5).
In the preferred embodiment of the present invention, described by Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is soluble in water, be specially:
By Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is dissolved in de aerated water, the amount of described de aerated water is 60-120ml/mmolEu (NO 3) 36H 2o.
P-coumaric acid and stratiform europium oxyhydroxide LEuH utilize ion exchange method to synthesize P-coumaric acid-LEuH complex body by the present invention.After forming complex body, because P-coumaric acid is to Eu in LEuH 3+the cancellation effect of fluorescence, thus, the fluorescent characteristic of LEuH and P-coumaric acid-LEuH complex body shows larger difference.The difference of this fluorescent characteristic is utilized indirectly to detect P-coumaric acid.
Accompanying drawing explanation
In order to be illustrated more clearly in the embodiment of the present invention or technical scheme of the prior art, be briefly described to the accompanying drawing used required in embodiment or description of the prior art below, apparently, accompanying drawing in the following describes is only some embodiments of the present invention, for those of ordinary skill in the art, under the prerequisite not paying creative work, other accompanying drawing can also be obtained according to these accompanying drawings.
Fig. 1 is the LEuH of the embodiment of the present invention 1 preparation, the XRD figure of P-coumaric acid-LEuH complex body;
Fig. 2 is the infrared spectrogram of the P-coumaric acid-LEuH complex body of preparation in the LEuH and the embodiment of the present invention 1 prepared in P-coumaric acid, the embodiment of the present invention 1;
Fig. 3 is the LEuH of preparation and the fluorescence spectrum figure of P-coumaric acid-LEuH complex body in the embodiment of the present invention 1.
Embodiment
In the last few years, stratified material caused people with the character of its uniqueness and paid close attention to greatly, stratiform europium oxyhydroxide Eu (OH) especially wherein 2.4(NO 3) 0.60.85H 2o (being called for short LEuH), because introducing rare-earth europium ion on main body laminate, becomes the layered ion type functional materials that a class is novel.
Because LEuH laminate is positively charged, interlayer is tradable negatively charged ion, therefore, it easily and anionic compound react.
Utilize its this character, P-coumaric acid after deprotonation, is reacted by ion exchange method with LEuH, synthesizes P-coumaric acid-LEuH complex body by contriver's design.
The invention provides P-coumaric acid-LEuH complex body, this complex body has following chemical constitution:
Eu(OH) 2.4(C 9H 6O 3) 0.3·1.33H 2O；
Use X-ray diffractometer to carry out test to this complex body and obtain X-ray diffractogram, wherein, the pass at spacing d and θ angle, Prague 2 is:
Use infrared spectrometer to carry out detection to this complex body and obtain infrared spectra, wherein, in red place spectrum, the contrast relationship of wave number and absorption peak is:
3423 – OH stretching vibration
1630 Trans double bond stretching vibration
1593 –COO ˉAntisymmetric stretching vibration
1429 –COO ˉSymmetrical stretching vibration
1508 Phenyl ring stretching vibration
1384 NO 3 ˉMiddle N-O flexural vibration
980 Trans double bond C-H out-of-plane deformation vibration
836 Disubstituted benzenes fingerprint region is absorbed
566 Eu-O is flexible/flexural vibration
The synthetic method of above-mentioned P-coumaric acid-LEuH complex body can comprise the following steps:
1) LEuH is synthesized:
By Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is soluble in water, obtains the aqueous solution, wherein, Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine mol ratio be: 1:(10-15): (0.5-1.5); Preferably by Eu (NO3) 36H 2o, NaNO 3, hexamethylenetetramine is dissolved in de aerated water, de aerated water refers to eliminate the water of institute's dissolved gases in water, and boiled by distilled water and namely can obtain for 10 minutes, the degassed water yield is preferably 60-120ml/mmolEu (NO 3) 36H 2o.
N is passed in the above-mentioned aqueous solution 2, pass into N 2time be preferably 3-10min, then carry out hydro-thermal reaction, preferred temperature of reaction is 70-100 DEG C; The preferred reaction times is 12-18h, and after reaction terminates, filter the product obtained, filter the filter method that chemical field can be adopted conventional, such as adopt the mode of suction filtration to filter, this is not restricted for the embodiment embodiment of the present invention of filtration.Filter again after washing product with water, 1-4 time repeatedly, finally vacuum-drying 18-24 hour at 40-70 DEG C, obtain white powder Eu (OH) 2.4(NO 3) 0.60.85H 2o, is called for short LEuH.
2) P-coumaric acid-LEuH complex body is synthesized:
By P-coumaric acid and NaOH obtained P-coumaric acid sodium-salt aqueous solution soluble in water, wherein, the mol ratio of P-coumaric acid and NaOH is: 1:(1.5-2.5), and the consumption of water is preferably 5-20ml/mmol P-coumaric acid.
By step 1) in the LEuH of synthesis be scattered in after in water, add P-coumaric acid sodium-salt aqueous solution, obtain mixed solution, wherein, the mol ratio of LEuH and P-coumaric acid sodium salt is: 1:(2-9), preferably 1:(3-6).
By above-mentioned mixed solution at hydro-thermal reaction 12-24 hour at 40-120 DEG C; After reaction terminates, filter the product obtained, filter again after washing product with water, 1-4 time repeatedly, finally vacuum-drying 18-24 hour at 40-70 DEG C, namely obtain yellow powder P-coumaric acid-LEuH complex body.
It should be noted that, the embodiment of the present invention is in the process of synthesizing LEuH and P-coumaric acid-LEuH complex body, and the water used is preferably deionized water or distilled water.
It should be noted that all raw materials that the embodiment of the present invention adopts do not have special restriction to its source, commercially buy or make by oneself further.
The experimental installation that the embodiment of the present invention adopts in the process of synthesizing LEuH and P-coumaric acid-LEuH complex body, is the equipment that this area is general, does not have special requirement, all can commercially buy.Contriver believes, those skilled in the art completely can by selecting suitable experimental installation to the description of technical solution of the present invention, and the present invention does not carry out concrete restriction and explanation to experimental installation at this.
In order to further illustrate the present invention, be described this bright technical scheme below in conjunction with specific embodiment, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtained under creative work prerequisite, belong to the scope of protection of the invention.
Reagent used in following examples is commercially available.
Embodiment 1
By 0.446g (1mmol) Eu (NO 3) 36H 2o, 0.846g (10mmol) NaNO 3, 0.07g (0.5mmol) hexamethylenetetramine is dissolved in 65ml de aerated water, obtains the aqueous solution, this aqueous solution to be transferred in reactor and pass into N in this aqueous solution 23min, then 70 DEG C of hydro-thermal reactions 18 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration again with after deionized water wash product, 2 times repeatedly, and then vacuum-drying 24 hours at 40 DEG C, obtains white powder LeuH0.196g.Take LEuH as benchmark, productive rate is 80%.
Join in 20mL deionized water by the NaOH of the P-coumaric acid of 0.207g (1.26mmol) and 0.108g (2.52mmol), the ultrasonic P-coumaric acid that makes dissolves, and obtains the P-coumaric acid sodium-salt aqueous solution clarified.
Mix with above-mentioned obtained P-coumaric acid sodium-salt aqueous solution after 0.10g (0.42mmol) LEuH being scattered in 140ml deionized water, and transfer in reactor, 50 DEG C of hydro-thermal reactions 22 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration after washing product with water again, 3 times repeatedly; Last vacuum-drying 24 hours at 40 DEG C, obtains yellow powder P-coumaric acid-LEuH complex body 0.089g.Take LEuH as benchmark, productive rate is 80%.
Embodiment 2
By 0.446g (1mmol) Eu (NO 3) 36H 2o, 1.10g (13mmol) NaNO 3, 0.14g (1mmol) hexamethylenetetramine is dissolved in 80ml and is vented in water, obtains the aqueous solution, this aqueous solution to be transferred in reactor and pass into N in this aqueous solution 25min, then 90 DEG C of hydro-thermal reactions 14 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration again with after deionized water wash product, 3 times repeatedly, then vacuum-drying 20 hours at 60 DEG C, obtains white powder LeuH0.240g.Take LEuH as benchmark, productive rate is 98%.
Join in 15mL deionized water by the NaOH of the P-coumaric acid of 0.207g (1.26mmol) and 0.081g (1.9mmol), the ultrasonic P-coumaric acid that makes dissolves, and obtains the P-coumaric acid sodium-salt aqueous solution clarified.
Mix with above-mentioned obtained P-coumaric acid sodium-salt aqueous solution after 0.05g (0.21mmol) LEuH being scattered in 100ml deionized water, and transfer in reactor, 100 DEG C of hydro-thermal reactions 16 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration after washing product with water again, 4 times repeatedly; Then vacuum-drying 20 hours at 60 DEG C, obtains yellow powder P-coumaric acid-LEuH complex body 0.055g.Take LEuH as benchmark, productive rate is 98%.
Embodiment 3
By 0.446g (1mmol) Eu (NO 3) 36H 2o, 1.27g (15mmol) NaNO 3, 0.225g (1.5mmol) hexamethylenetetramine is dissolved in 100ml and is vented in water, obtains the aqueous solution, this aqueous solution to be transferred in reactor and to pass into N to this aqueous solution 210min, 100 DEG C of hydro-thermal reactions 12 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration again with after deionized water wash product, 4 times repeatedly, and then vacuum-drying 24 hours at 40 DEG C, obtains white powder LEuH0.240g.Be benchmark according to LEuH, calculating productive rate is 98%.
Join in 25mL deionized water by the NaOH of the P-coumaric acid of 0.207g (1.26mmol) and 0.135g (3.15mmol), the ultrasonic P-coumaric acid that makes dissolves, and obtains the P-coumaric acid sodium-salt aqueous solution clarified.
Mix with above-mentioned obtained P-coumaric acid sodium-salt aqueous solution after 0.038g (0.16mmol) LEuH being scattered in 70ml deionized water, and transfer in reactor, 120 DEG C of hydro-thermal reactions 12 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration after washing product with water again, 3 times repeatedly, and then vacuum-drying 24 hours at 40 DEG C, obtains yellow powder P-coumaric acid-LEuH complex body 0.041g.Take LEuH as benchmark, productive rate is 96%.
Characterize and analyze
1, ultimate analysis
For determining the LEuH of preparation and the composition of P-coumaric acid-LEuH complex body in the embodiment of the present invention 1, the elemental analyser adopting German Elementar company to produce (model: Vario EL) records the LEuH of preparation and C, H, the N content of P-coumaric acid-LEuH complex body in the embodiment of the present invention 1 respectively; Plasma body inductance linking atom emission spectrometer (ICP) (model: SPECTROARCOSEOP) adopting Spectro Analypical Instruments GmbH to produce records the Eu content of LEuH and the P-coumaric acid-LEuH complex body prepared in the embodiment of the present invention respectively, thus the chemical constitution calculating the LEuH of preparation in the embodiment of the present invention 1 is Eu (OH) 2.4(NO 3) 0.60.85H 2the chemical constitution of O, P-coumaric acid-LEuH complex body is Eu (OH) 2.4(C 9h 6o 3) 0.31.33H 2o, related data is as shown in table 1 and table 2.
The ultimate analysis of table 1LEuH and icp analysis data
The ultimate analysis of table 2 P-coumaric acid-LEuH complex body and icp analysis data
2, XRD (ray diffraction, X-ray diffraction) analyzes
The x-ray powder diffraction instrument (model: X Pert PRO MPD) adopting Dutch PA Nalytical company to produce carries out XRD sign to the LEuH of preparation in the embodiment of the present invention 1 and P-coumaric acid-LEuH complex body, and XRD figure as shown in Figure 1.
The XRD figure of the LEuH that (a) is prepared for embodiment 1 in Fig. 1, as seen from the figure, in the XRD figure of the LEuH of gained occur 0.83,0.42,0.32,0.26nm series of features diffraction peak, illustrate and define laminate structure.Diffraction peak shape is sharp-pointed, illustrates that degree of crystallinity is very high.Illustrate and all can obtain the good LEuH of degree of crystallinity in above concentration proportioning and temperature range.
The XRD figure of the P-coumaric acid-LEuH complex body that (b) is prepared for embodiment 1 in Fig. 1, as seen from the figure, hydro-thermal reaction gained complex body keeps NO 3 --the laminate structure of type LEuH, occurs 1.48,0.77,0.52, the a series of diffraction peak of 0.39,0.31nm, form layers spacing is the complex body of 1.48nm, and interlamellar spacing increases, show that between P-coumaric acid success interposed layer, form layers spacing is the complex body of 1.48nm, and the degree of crystallinity of products obtained therefrom is better.
3, Infrared spectroscopy
P-coumaric acid-LEuH the complex body of Fourier transform infrared spectrometer (FT-IR) (model: Nicolet360) to preparation in the LEuH of preparation in P-coumaric acid, the embodiment of the present invention 1 and the embodiment of the present invention 1 adopting Nicolet company of the U.S. to produce carries out Infrared Characterization and (adopts KBr pressed disc method, scan under room temperature, test specification is 4000 ~ 400cm -1), infrared spectrogram is as shown in Figure 2.
In Fig. 2, (a) is the infrared spectrogram of the LEuH of preparation in the embodiment of the present invention 1; The infrared spectrogram that in Fig. 2, (b) is P-coumaric acid; In Fig. 2, (c) is the infrared spectrogram of the P-coumaric acid-LEuH complex body of preparation in the embodiment of the present invention 1.
As seen from the figure, 3539cm in LEuH (a) -1for the stretching vibration of-OH absorbs, 1643cm -1for the flexural vibration of-OH absorb, 1384cm -1for NO 3 --n-O flexural vibration, 594cm -1for Eu-O flexible/flexural vibration absorb.3362cm in P-coumaric acid (b) -1for the stretching vibration of-OH absorbs, 1672 and 1448cm -1the unsymmetrically and the symmetrical stretching vibration that are respectively carboxyl C=O absorb, 1627cm -1for the stretching vibration of trans double bond absorbs, 1512cm -1for the stretching vibration of phenyl ring absorbs, 978cm -1for trans double bond C-H out-of-plane deformation vibration absorbs, 833cm -1for absorbing the fingerprint region of disubstituted benzenes.After forming complex body (c), 1593 and 1429cm -1place is respectively to answering – COO --the flexible and symmetrical stretching vibration of unsymmetrically absorb, due to deprotonation, absorb position and all occur red shift (respective absorption of intercalation Qian – COOH is at 1672cm -1and 1448cm -1), 1508cm -1place is the stretching vibration of phenyl ring, 980cm -1for trans double bond C-H out-of-plane deformation vibration absorbs, 836cm -1for absorbing the fingerprint region of disubstituted benzenes, due to intercalation, in complex body all there is displacement in the group absorptions of organism negatively charged ion, and the effect of interlayer object and laminate is described.Above information proves successfully to have prepared P-coumaric acid-LEuH complex body further.
4, fluorescent spectroscopy
The spectrophotofluorometer (model: RF-5301PC) adopting Japanese Shimadzu Corporation to produce carries out fluorometric investigation to the LEuH of preparation in the embodiment of the present invention 1 and P-coumaric acid-LEuH complex body, and fluorescence spectrum as shown in Figure 3; Wherein, excite slit to be 1.5nm in test, transmitting slit is 3.0nm.
In Fig. 3, (a) is the emmission spectrum of LEuH under 395nm excites.Emission peak is positioned at 578,595,613,660,700nm, belong to Eu respectively 3+'s 5d 0- 7f j(J=0,1,2,3,4) transition.Wherein be positioned at launching the most by force of 613nm 5d 0- 7f 2for electric dipole transition, corresponding Eu 3+characteristic red light emission. 5d 0- 7f jthe relative intensity of transition emission peak and the usual detectable Eu of the division situation at peak 3+one-tenth key environment.In LEuH precursor, 5d 0- 7f 2transition is main peak, and Eu is described 3+in lattice, occupy non-centrosymmetry position, in structure, there is no the centre of inversion.In addition, 5d 0- 7f 1with 5d 0- 7f 2emission peak is all split into two peaks, and Eu is described 3+around crystal structure symmetry is low.
In figure, (b) is the emmission spectrum of P-coumaric acid-LEuH complex body under 395nm excites of preparation in the embodiment of the present invention 1 under same test condition.As seen from the figure, as interlayer NO 3 --after being exchanged for P-coumaric acid root, fluorescence intensity significantly reduces, and illustrates and to form after complex body cancellation Eu 3+fluorescence
Be understandable that, because the composition of LEuH prepared in embodiment 2-3 and P-coumaric acid-LEuH complex body and the LeuH prepared by embodiment 1 and P-coumaric acid-LEuH complex body and structure are consistent.Therefore, the sign of the LEuH that the embodiment of the present invention is prepared in this is to embodiment 2-3 and P-coumaric acid-LEuH complex body is not described specifically, with reference to embodiment 1.
P-coumaric acid and stratiform europium oxyhydroxide LEuH utilize ion exchange method to synthesize P-coumaric acid-LEuH complex body by the present invention.After forming complex body, due to the quenching effect of-OH in P-coumaric acid, make the Eu of former LEuH 3+fluorescence be quenched, thus, the fluorescent characteristic of LEuH and P-coumaric acid-LEuH complex body shows larger difference.The difference of this fluorescent characteristic is utilized indirectly to detect P-coumaric acid.
Moreover, due to the existence of inorganic lamellar material LEuH, make the stability of the P-coumaric acid group of P-coumaric acid-LEuH complex body be higher than P-coumaric acid monomer, namely serve the effect of protection P-coumaric acid.
Above P-coumaric acid-LEuH complex body provided by the present invention and synthetic method thereof are described in detail.Apply specific embodiment herein to set forth principle of the present invention and embodiment, the explanation of above embodiment just understands method of the present invention and clou thereof for helping.It should be pointed out that for the person of ordinary skill of the art, under the premise without departing from the principles of the invention, can also carry out some improvement and modification to the present invention, these improve and modify and also fall in the protection domain of the claims in the present invention.

Claims (11)

1. P-coumaric acid-LEuH complex body, is characterized in that, has following chemical formula composition:
Eu(OH) 2.4(C 9H 6O 3) 0.3·1.33H 2O。
2. complex body as claimed in claim 1, is characterized in that, use X-ray diffractometer to test the X-ray diffractogram obtaining described complex body to this complex body, wherein, the pass at spacing d and θ angle, Prague 2 is:
3. complex body as claimed in claim 1, is characterized in that, use infrared spectrometer to test the infrared spectra obtaining described complex body to this complex body, wherein, the wave number of the charateristic avsorption band in infrared spectra is respectively: 3423 (cm -1), 1630 (cm -1), 1593 (cm -1), 1508 (cm -1), 1429 (cm -1), 1384 (cm -1), 980 (cm -1), 836 (cm -1) and 566 (cm -1).
4. the synthetic method of P-coumaric acid-LEuH complex body as claimed in claim 1, is characterized in that, comprise the following steps:
A) be scattered in water by LEuH, then add P-coumaric acid sodium-salt aqueous solution, obtain mixed solution, wherein, the mol ratio of LEuH and P-coumaric acid sodium salt is: 1:(2-9);
B) by described mixed solution at 40-120 DEG C, hydro-thermal reaction 12-24 hour at preferred 70-100 DEG C, reaction terminates to carry out aftertreatment to obtained product afterwards.
5. synthetic method as claimed in claim 4, it is characterized in that, the temperature of described hydro-thermal reaction is 70-100 DEG C.
6. synthetic method as claimed in claim 4, it is characterized in that, the synthetic method of described P-coumaric acid sodium-salt aqueous solution is: obtained with NaOH is soluble in water by P-coumaric acid.
7. synthetic method as claimed in claim 6, it is characterized in that, the mol ratio of described P-coumaric acid and NaOH is: 1:(1.5-2.5).
8. synthetic method as claimed in claim 4, it is characterized in that, the mol ratio of described LEuH and P-coumaric acid sodium salt is: 1:(3-6).
9. synthetic method as claimed in claim 4, it is characterized in that, described aftertreatment comprises: filtration, washing, drying.
10. synthetic method as claimed in claim 4, it is characterized in that, the synthetic method of described LEuH is:
By Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is soluble in water, obtain the aqueous solution, then in obtained aqueous solution, pass into N 23-10 minute, carries out hydro-thermal reaction 12-18h at 70-100 DEG C, and reaction terminates rear to the filtration of obtained product, washing, drying;
Wherein, Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine mol ratio be: 1:(10-15): (0.5-1.5).
11. synthetic methods as claimed in claim 10, is characterized in that, described by Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is soluble in water, be specially:
By Eu (NO 3) 36H 2o, NaNO 3, hexamethylenetetramine is dissolved in de aerated water, the amount of described de aerated water is 60-120ml/mmolEu (NO 3) 36H 2o.
CN201410295668.3A 2014-06-26 2014-06-26 P-coumaric acid-LEuH complex body and synthetic method thereof Expired - Fee Related CN104119904B (en)

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CN102565421A (en) * 2011-12-27 2012-07-11 北京师范大学 Tyrosine radical/LRH complex for amino acid detection and synthesis method of the complex
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