CN104267007A - p-coumaric acid-LTbH complex and synthesis method thereof - Google Patents

p-coumaric acid-LTbH complex and synthesis method thereof Download PDF

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CN104267007A
CN104267007A CN201410413510.1A CN201410413510A CN104267007A CN 104267007 A CN104267007 A CN 104267007A CN 201410413510 A CN201410413510 A CN 201410413510A CN 104267007 A CN104267007 A CN 104267007A
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ltbh
coumaric acid
complex
synthetic method
water
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CN104267007B (en
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马淑兰
苏飞飞
谷庆阳
李新新
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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 invention discloses a p-coumaric acid-LTbH complex and a synthesis method thereof. The p-coumaric acid-LTbH complex has the chemical formula of Tb(OH)<2.5>(C9H6O3)<0.24>.2.3H2O. p-coumaric acid and Cl<->-type layered terbium hydroxide Cl-LTbH are synthesized into the p-coumaric acid-LTbH complex by an ion exchange method. After complex formation, p-coumaric acid has effects of quenching fluorescence of Tb<3+> in LTbH and thus fluorescence characteristics of the p-coumaric acid-LTbH complex are very different from those of Cl-LTbH. Through use of the difference of the fluorescence characteristics, p-coumaric acid can be indirectly detected.

Description

P-Coumaric Acid-LTbH complex and synthetic method thereof
Technical field
The present invention relates to organic synthesis field, particularly p-Coumaric Acid-LTbH complex 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 legume, can be widely used in the fields such as medicine, agricultural, chemical industry.In medical, p-Coumaric Acid has anticancer, antitumor action, and has protective effect to the mutagenesis of liver and oxidative damage.In addition, the important intermediate that it or some medicines are produced, can be used to prepare anesthetic, germifuge and styptic.Agriculturally, p-Coumaric Acid may be used for producing plant growth promoter, germifuge 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 electric conductivity.
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-LTbH complex and synthetic method thereof; Technical scheme is as follows:
P-Coumaric Acid-LTbH complex, has following chemical formula composition:
Tb(OH) 2.5(C 9H 6O 3) 0.24·2.3H 2O。
Use infrared spectrometer to test the infrared spectrum obtaining described complex to this complex, wherein, the wave number of the characteristic absorption peak in infrared spectrum is respectively: 3452 (cm -1), 1630 (cm -1), 1594 (cm -1), 1507 (cm -1), 1384 (cm -1), 1170 (cm -1), 980 (cm -1), 837 (cm -1), 597 (cm -1), 412 (cm -1).
The present invention also provides the synthetic method of p-Coumaric Acid-LTbH complex simultaneously, comprises the following steps:
A) be scattered in water by Cl-LTbH, then add p-Coumaric Acid sodium-salt aqueous solution, obtain mixed liquor, wherein, the mol ratio of Cl-LTbH and p-Coumaric Acid sodium salt is 1:(2.5-4);
B) by described mixed liquor at 60-130 DEG C, hydro-thermal reaction 12-24 hour at preferred 70-110 DEG C, reaction terminates to carry out aftertreatment to obtained product afterwards.
In the preferred embodiment of the present invention, 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 Cl-LTbH and p-Coumaric Acid sodium salt is 1:3.
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 Cl-LTbH is:
By Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are soluble in water, obtain 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, Tb (NO 3) 36H 2the mol ratio of O, NaCl, hexamethylenetetramine is: 1:(10-15): (0.5-1.5).
In the preferred embodiment of the present invention, described by Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are soluble in water, are specially:
By Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are dissolved in de aerated water, and the amount of described de aerated water is 60-120mL/mmolTb (NO 3) 36H 2o.
The present invention is by p-Coumaric Acid and Cl --type stratiform terbium oxyhydroxide Cl-LTbH utilizes ion exchange process to synthesize p-Coumaric Acid-LTbH complex.After forming complex, because p-Coumaric Acid is to Tb in LTbH 3+the cancellation effect of fluorescence, thus, the fluorescent characteristic of Cl-LTbH and p-Coumaric Acid-LTbH complex 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 Cl-LTbH of the embodiment of the present invention 1 preparation, the XRD figure of p-Coumaric Acid-LTbH complex;
Fig. 2 is the infrared spectrogram of the p-Coumaric Acid-LTbH complex of preparation in the Cl-LTbH and the embodiment of the present invention 1 prepared in p-Coumaric Acid, the embodiment of the present invention 1;
Fig. 3 is the Cl-LTbH of preparation and the fluorescence spectrum figure of p-Coumaric Acid-LTbH complex 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 terbium oxyhydroxide Tb (OH) especially wherein 2.5cl 0.36(CO 3) 0.070.82H 2(interlayer anion is Cl to O --, be called for short Cl-LTbH), because introducing rare earth terbium ion on main body laminate, become the layered ion type functional material that a class is novel.
Because Cl-LTbH laminate is positively charged, the Cl of interlayer --for tradable negative ion, therefore, it easily and other anionic compound carry out exchange reaction.
Utilize its this character, p-Coumaric Acid after deprotonation, is reacted by ion exchange process with Cl-LTbH, synthesizes p-Coumaric Acid-LTbH complex by inventor's design.
The invention provides p-Coumaric Acid-LTbH complex, this complex has following chemical composition:
Tb(OH) 2.5(C 9H 6O 3) 0.24·2.3H 2O；
Use infrared spectrometer to carry out detection to this complex and obtain infrared spectrum, wherein, the wave number of the characteristic absorption peak in infrared spectrum is respectively:
3452(cm -1)、1630(cm -1)、1594(cm -1)、1507(cm -1)、1384(cm -1)、1170(cm -1)、980(cm -1)、837(cm -1)、597(cm -1)、412(cm -1)。The synthetic method of above-mentioned p-Coumaric Acid-LTbH complex can comprise the following steps:
1) Cl-LTbH is synthesized:
By Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are soluble in water, obtain aqueous solution, wherein, and Tb (NO 3) 36H 2the mol ratio of O, NaCl, hexamethylenetetramine is: 1:(10-15): (0.5-1.5); Preferably by Tb (NO3) 36H 2o, NaCl, hexamethylenetetramine are dissolved in de aerated water, and 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/mmolTb (NO 3) 36H 2o.
N is passed in 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 time 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 Tb (OH) 2.5cl 0.36(CO 3) 0.070.82H 2o, is called for short Cl-LTbH.
2) p-Coumaric Acid-LTbH complex 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 Cl-LTbH of synthesis be scattered in after in water, add p-Coumaric Acid sodium-salt aqueous solution, obtain mixed liquor, wherein, the mol ratio of Cl-LTbH and p-Coumaric Acid sodium salt is: 1:(2.5-4), preferably 1:3.
By above-mentioned mixed liquor at 60-130 DEG C, at preferred 70-110 DEG C, react 12-24 hour; 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 the Powdered p-Coumaric Acid of khaki-LTbH complex.
It should be noted that, the embodiment of the present invention is in the process of synthesizing Cl-LTbH and p-Coumaric Acid-LTbH complex, 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 facilities that the embodiment of the present invention adopts in the process of synthesizing Cl-LTbH and p-Coumaric Acid-LTbH complex, is the equipment that this area is general, does not have special requirement, all can commercially buy.Inventor believes, those skilled in the art completely can by selecting suitable experimental facilities to the description of technical solution of the present invention, and the present invention does not carry out concrete restriction and explanation to experimental facilities at this.
In order to further illustrate the present invention, be described technical scheme of the present invention 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 0.453g (1mmol) Tb (NO 3) 36H 2o, 0.585g (10mmol) NaCl, 0.07g (0.5mmol) hexamethylenetetramine is dissolved in 65mL de aerated water, obtains aqueous solution, this aqueous solution to be transferred in reactor and pass into N in this aqueous solution 23min, then reaction 18 hours at 70 DEG C.After reaction terminates, suction filtration obtains product, carries out suction filtration again after spending deionized water product, 2 times repeatedly, and then vacuum drying 24 hours at 40 DEG C, obtain white powder Cl-LTbH0.210g, productive rate is 90%.
Join in 10mL deionized water by the NaOH of the p-Coumaric Acid of 0.103g (0.63mmol) and 0.054g (1.26mmol), 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) Cl-LTbH being scattered in 75mL deionized water, and transfer in reactor, 70 DEG C of hydro-thermal reactions 20 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 khaki powder p-Coumaric Acid-LTbH complex 0.056g.Take Cl-LTbH as benchmark, productive rate is 95%.
Embodiment 2
By 0.453g (1mmol) Tb (NO 3) 36H 2o, 0.761g (13mmol) NaCl, 0.14g (1mmol) hexamethylenetetramine is dissolved in 80mL and is vented in water, obtains 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 after spending deionized water product again, 3 times repeatedly, then vacuum drying 20 hours at 60 DEG C, obtain white powder Cl-LTbH0.221g, productive rate is 95%.
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 0.075g (0.32mmol) Cl-LTbH being scattered in 85mL deionized water, and transfer in reactor, 90 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 khaki powder p-Coumaric Acid-LTbH complex 0.087g.Take LTbH as benchmark, productive rate is 96%.
Embodiment 3
By 0.453g (1mmol) Tb (NO 3) 36H 2o, 0.878g (15mmol) NaCl, 0.225g (1.5mmol) hexamethylenetetramine is dissolved in 100mL and is vented in water, obtains aqueous solution, this aqueous solution to be transferred in reactor and to pass into N to this aqueous solution 210min, 110 DEG C of hydro-thermal reactions 12 hours.After reaction terminates, the product that suction filtration obtains, carries out suction filtration after spending deionized water product again, 4 times repeatedly, and then vacuum drying 24 hours at 40 DEG C, obtain white powder LTbH 0.228g, 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 0.12g (0.50mmol) Cl-LTbH being scattered in 90mL deionized water, and transfer in reactor, 110 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 khaki powder p-Coumaric Acid-LTbH complex 0.135g.Take LTbH as benchmark, productive rate is 97%.
Characterize and analyze
1, ultimate analysis
For determining the Cl-LTbH of preparation and the composition of p-Coumaric Acid-LTbH complex in the embodiment of the present invention 1, the elemental analyser adopting German Elementar company to produce (model: Vario EL) records the Cl-LTbH of preparation and C, H, the N content of p-Coumaric Acid-LTbH complex in the embodiment of the present invention 1 respectively; Plasma inductance linking atom emission spectrometer (ICP) (model: SPECTROARCOSEOP) adopting Spectro Analypical Instruments GmbH to produce records the Tb content of Cl-LTbH and the p-Coumaric Acid-LTbH complex prepared in the embodiment of the present invention respectively, thus the chemical composition calculating the Cl-LTbH of preparation in the embodiment of the present invention 1 is Tb (OH) 2.5cl 0.36(CO 3) 0.070.82H 2the chemical composition of O, p-Coumaric Acid-LTbH complex is Tb (OH) 2.5(C 9h 6o 3) 0.242.3H 2o.
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 Cl-LTbH of preparation in the embodiment of the present invention 1 and p-Coumaric Acid-LTbH complex, and XRD figure as shown in Figure 1.
In Fig. 1 the Cl-LTbH that (a) is prepared for embodiment 1 XRD figure, as seen from the figure, in the XRD figure of the LTbH of gained occur 0.84,0.42,0.32,0.30,0.26nm series of features diffraction peak, illustrate and define layer structure.Diffraction peak shape is sharp-pointed, illustrates that crystallinity is very high.Illustrate that embodiment 1 can obtain the good Cl-LTbH of crystallinity.
The XRD figure of the p-Coumaric Acid-LTbH complex that (b) is prepared for embodiment 1 in Fig. 1, as seen from the figure, hydro-thermal reaction gained complex keeps layer structure, occurs 1.56,0.75, the a series of diffraction peak of 0.51nm, forming interlamellar spacing is the complex of 1.56nm, and interlamellar spacing increases, and shows between p-Coumaric Acid success insert layer, forming interlamellar spacing is the complex of 1.56nm, and the crystallinity of products obtained therefrom is better.
3, Infrared spectroscopy
P-Coumaric Acid-LTbH the complex of Fourier transform infrared spectrometer (FT-IR) (model: Nicolet360) to preparation in the Cl-LTbH 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 IR 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.
The infrared spectrogram that in Fig. 2, (a) is p-Coumaric Acid; In Fig. 2, (b) is the infrared spectrogram of the Cl-LTbH of preparation in the embodiment of the present invention 1; In Fig. 2, (c) is the infrared spectrogram of the p-Coumaric Acid-LTbH complex of preparation in the embodiment of the present invention 1.
As seen from the figure, 3374cm in p-Coumaric Acid -1for the stretching vibration of-OH absorbs, 1672 and 1449cm -1the antisymmetry and the symmetrical stretching vibration that are respectively carboxyl C=O absorb, 1601cm -1for the stretching vibration of trans double bond absorbs, 1512cm -1for the stretching vibration of phenyl ring absorbs.3522cm in precursor Cl-LTbH -1for the stretching vibration of-OH absorbs, 1632cm -1for the flexural vibrations of-OH absorb, 637cm -1for Tb-O flexible/flexural vibrations absorb.Formed after complex, 1594 and 1384cm -1– COO in the corresponding p-Coumaric Acid of place's difference --the flexible and symmetrical stretching vibration of antisymmetry absorb, due to deprotonation, absorb position and all occur red shift (before intercalation, respective absorption is 1672 and 1449cm -1), 1507cm -1place is the stretching vibration of phenyl ring.Due to special adsorption, in complex there is displacement in the group absorptions of p-Coumaric Acid radical ion, and the effect of interlayer object and laminate is described.Above information proves successfully to have prepared p-Coumaric Acid-LTbH complex further.
4, fluorescent spectroscopy
The fluorospectrophotometer (model: RF-5301PC) adopting Japanese Shimadzu Corporation to produce carries out fluorometric investigation to the Cl-LTbH of preparation in the embodiment of the present invention 1 and p-Coumaric Acid-LTbH complex, 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 emission spectrum of Cl-LTbH under 395nm excites.Emission peak is positioned at 489,545,586,622nm, belong to Tb respectively 3+'s 5d 4- 7f j(J=6,5,4,3) transition.Wherein be positioned at launching the most by force of 545nm 5d 4- 7f 5for electric dipole transition, corresponding Tb 3+green light characteristic launch. 5d 4- 7f jthe relative intensity of transition emission peak and the usual detectable Tb of the division situation at peak 3+one-tenth key environment.In Cl-LTbH precursor, 5d 4- 7f 5transition is main peak, and Tb is described 3+in lattice, occupy non-centrosymmetry position, in structure, there is no inversion center.Point in LTbH 5d 4- 7f 6energy level transition splitting becomes two emission peaks, and Tb is described 3+be in a low symmetrical environment.This is due to Tb in LTbH crystal 3+have that two kinds of coordination modes cause.Bimodal from splitting, Tb in LTbH structure 3+based on two kinds of coordination modes.As interlayer Cl -after being exchanged for p-Coumaric Acid root, fluorescence intensity significantly reduces, and as Fig. 3 (b), illustrates and to form after complex cancellation Tb 3+fluorescence.
Be understandable that, because the composition of Cl-LTbH prepared in embodiment 2-3 and p-Coumaric Acid-LTbH complex and the LTbH prepared by embodiment 1 and p-Coumaric Acid-LTbH complex and structure are consistent.Therefore, the sign of the LTbH that the embodiment of the present invention is prepared in this is to embodiment 2-3 and p-Coumaric Acid-LTbH complex is not described specifically, with reference to embodiment 1.
P-Coumaric Acid and stratiform terbium oxyhydroxide Cl-LTbH utilize ion exchange process to synthesize p-Coumaric Acid-LTbH complex by the present invention.After forming complex, due to the quenching effect of p-Coumaric Acid, make former LTbH laminate Tb 3+fluorescence be quenched, thus, the fluorescent characteristic of Cl-LTbH and p-Coumaric Acid-LTbH complex 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 LTbH, make the stability of the p-Coumaric Acid group of p-Coumaric Acid-LTbH complex be higher than p-Coumaric Acid itself, namely serve the effect of protection p-Coumaric Acid.
Above p-Coumaric Acid-LTbH complex 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 central idea 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 (9)

1. p-Coumaric Acid-LTbH complex, is characterized in that, has following chemical formula composition:
Tb(OH) 2.5(C 9H 6O 3) 0.24·2.3H 2O。
2. complex as claimed in claim 1, is characterized in that, use infrared spectrometer to test the infrared spectrum obtaining described complex to this complex, wherein, the wave number of the characteristic absorption peak in infrared spectrum is respectively: 3452 (cm -1), 1630 (cm -1), 1594 (cm -1), 1507 (cm -1), 1384 (cm -1), 1170 (cm -1), 980 (cm -1), 837 (cm -1), 597 (cm -1), 412 (cm -1).
3. the synthetic method of p-Coumaric Acid-LTbH complex as claimed in claim 1, is characterized in that, comprise the following steps:
A) be scattered in water by Cl-LTbH, then add p-Coumaric Acid sodium-salt aqueous solution, obtain mixed liquor, wherein, the mol ratio of Cl-LTbH and p-Coumaric Acid sodium salt is 1:(2.5-4);
B) by described mixed liquor at 60-130 DEG C, hydro-thermal reaction 12-24 hour at preferred 70-110 DEG C, reaction terminates to carry out aftertreatment to obtained product afterwards.
4. synthetic method as claimed in claim 3, 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.
5. synthetic method as claimed in claim 4, it is characterized in that, the mol ratio of described p-Coumaric Acid and NaOH is: 1:(1.5-2.5).
6. synthetic method as claimed in claim 3, it is characterized in that, the mol ratio of described Cl-LTbH and p-Coumaric Acid sodium salt is 1:3.
7. synthetic method as claimed in claim 3, it is characterized in that, described aftertreatment comprises: filtration, washing, drying.
8. synthetic method as claimed in claim 3, it is characterized in that, the synthetic method of described Cl-LTbH is:
By Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are soluble in water, obtain 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, Tb (NO 3) 36H 2the mol ratio of O, NaCl, hexamethylenetetramine is: 1:(10-15): (0.5-1.5).
9. synthetic method as claimed in claim 8, is characterized in that, described by Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are soluble in water, are specially:
By Tb (NO 3) 36H 2o, NaCl, hexamethylenetetramine are dissolved in de aerated water, and the amount of described de aerated water is 60-120mL/mmolTb (NO 3) 36H 2o.
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CN105802613A (en) * 2016-04-29 2016-07-27 北京石油化工学院 Preparation method of coumarins complex
CN105802613B (en) * 2016-04-29 2018-07-06 北京石油化工学院 A kind of preparation method of Coumarins complex

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