CN105561927B - A kind of method using nitrogenous material adsorbing separation palladium - Google Patents
A kind of method using nitrogenous material adsorbing separation palladium Download PDFInfo
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- CN105561927B CN105561927B CN201610079678.2A CN201610079678A CN105561927B CN 105561927 B CN105561927 B CN 105561927B CN 201610079678 A CN201610079678 A CN 201610079678A CN 105561927 B CN105561927 B CN 105561927B
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- 0 CCC1C(N=NC(*2)=C3C=Cc4ccc(ccc(C(*CNC(C(C5)C5(C)C5(C)*)=C5I*)=I)n5)c5c4*3)=C2C(C)(C)C1(C)C Chemical compound CCC1C(N=NC(*2)=C3C=Cc4ccc(ccc(C(*CNC(C(C5)C5(C)C5(C)*)=C5I*)=I)n5)c5c4*3)=C2C(C)(C)C1(C)C 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/46—Materials comprising a mixture of inorganic and organic materials
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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Abstract
The invention discloses a kind of method using nitrogenous material adsorbing separation palladium, include the following steps：Adsorbent is mixed with the aqueous solution of nitric acid containing various metals ion, the palladium ion in aqueous solution of nitric acid is adsorbed by adsorbent separation, and the adsorbent is made of compound loaded as shown in structural formula I on carrier.Every gram of adsorbent is mixed with 20~30 milliliters of aqueous solution of nitric acid.The carrier is the macro-pore SiO of coated polymer2.In aqueous solution of nitric acid, the concentration of nitric acid is 0.4~6M.The present invention utilizes the method for nitrogenous material adsorbing separation palladium in use, it is not necessary to adds other organic compounds, selectivity is good, and separating rate is fast, easy to operate, easy to spread.
Description
Technical field
The present invention relates to palladium element sepatation technical field, and in particular to a kind of side using nitrogenous material adsorbing separation palladium
Method.
Background technology
Precious metal palladium has special structure, there is special adsorption capacity to hydrogen and oxygen, therefore, is led in Industrial Catalysis
The status that can not substitute is occupied in domain.
Palladium can keep chemical inertness and with molten in addition to excellent catalytic activity within the scope of very wide temperature
Point height, rub resistance, the characteristic such as corrosion-resistant, ductility is strong, thermoelectrical stability is strong, are widely used in the industrial each neck of its people
Domain.
At present, palladium resource reserve in China's is limited, and yield is very low, far can not meet the needs of modern chemical industry, big portion
Divide and rely on import, and it is expensive.In the prior art, the preparation of palladium metal mainly passes through following three approach with source：
(1) the naturally utilization of the mineral resources containing palladium；
(2) palladium is recycled from cu-ni sulphide ore byproduct；
(3) recycling of the secondary resource containing palladium such as industrial waste gas palladium catalyst.
The metals resources such as the palladium obtained by these three approach are limited, and with the increase of palladium resource loss, it is difficult to realize
Sustainable use.
Nuclear power will not discharge since energy density is big, pollution is few and cause greenhouse gases and vigorously be sent out in recent years
Exhibition, but can be inevitably generated spentnuclear fuel among nuclear power operation.High activity liquid waste (HLLW) caused by spentnuclear fuel post processing,
It is a kind of peracidity, high radioactivity and highly toxic mixed solution, wherein containing a certain amount of Pd107, the half-life period of palladium is 6.5
×106Year, radiation sexual cycle is long, harm is big and content is high, if it is possible to realization recycling is carried out, it is significant, and it is still, existing
The separation of palladium element is still in conceptual phase in stage high activity liquid waste, does not find efficient recycling approach also.
The content of the invention
Easy to operate the present invention provides a kind of method using nitrogenous material adsorbing separation palladium, selectivity is good, separation effect
Rate is high, is easy to carry out industrial application.
A kind of method using nitrogenous material adsorbing separation palladium, includes the following steps：By adsorbent and contain various metals
The aqueous solution of nitric acid of ion mixes, and the palladium ion in aqueous solution of nitric acid is adsorbed by adsorbent separation, and the adsorbent is by such as structure
Compound loaded shown in Formulas I is made on carrier：
Wherein, R C1-C10Straight chain alkyl substituent, C1-C10Cycloalkanes base class substituent or C1-C10Phenyl ring substitution
Base.
Adsorbent is by (5,9,9- trimethyl -5,6,7,8- tetrahydrochysene -5,8- methylene the benzos of hydrophobicity 2,9- bis- in the present invention
[e] (1,2,4- triazine -3- bases))-[2,2'] -1,10- phenanthroline (R-BTPhen) (as shown in structural formula I) and carrier press one
Certainty ratio is for composite to be prepared.
Preferably, every gram of adsorbent is mixed with 20~30 milliliters of aqueous solution of nitric acid.Adsorbent selection provided by the invention
Property it is good, separative efficiency is high.
Preferably, the adsorbent is made of compound loaded as shown in formula II on carrier：
In the present invention, the carrier is the macro-pore SiO of coated polymer2。
The macro-pore SiO of the coated polymer2For silicon substrate-styrene-divinylbenzene polymer (SiO2- P), it is a kind of
Novel inorganic/organic support material, discloses SiO in United States Patent (USP) US68439212- styrene-divinylbenzene polymer,
SiO2- P is a kind of organic high polymer complex carrier of particle containing porous silicon dioxide carrier, and its preparation method is as follows：
(1) by the SiO of macropore2Washed, filtered with concentrated nitric acid, deionized water is washed till neutrality, repetition more than 10 times, drying.
(2) vacuum and have under argon gas protective condition, with 1,2,3- trichloropropane and m- dimethylbenzene for solvent, to macro-pore SiO2
The m/p- formyl styrene of middle addition 48.7g, the m/p- divinylbenzenes of 8.9g, 72.2g dioctyls face phthalic acid ester,
54.0g benzoin methyl acid sodium, 0.56g α, α-idol bis-isobutyronitrile and 0.57g1,1 '-idol dicyclohexyl amine -1- nitriles, by room temperature progressively
Be heated to 90 DEG C, and keep 13 it is small when, afterwards, be progressively cooled to room temperature.
(3) washed respectively with acetone and methanol, filter above-mentioned product, repeated more than 10 times, it is dry.
In the present invention, the preparation method of the adsorbent is as follows：
Compound as shown in structural formula I is dissolved in dichloromethane, carrier is added in resulting solution and is uniformly mixed,
After revolving is dry, adsorbent is obtained.
Preferably, the compound as shown in formula II is dissolved in dichloromethane, adds and carry in resulting solution
Body is uniformly mixed, and after revolving is dry, obtains adsorbent.
During revolving, most of dichloromethane is evaporated into closely dry state, under capillarity and physisorption, change
Adduct molecule enter carrier gap in, then the material of nearly dry state be dried in vacuo at 45~55 DEG C at least 24 it is small when,
Obtain adsorbent.
Preferably, every gram of compound as shown in structural formula I (compound as shown in formula II) is dissolved in 130~150
In milliliter dichloromethane.The mass ratio of compound (compound as shown in formula II) and carrier as shown in structural formula I is 1：8~
10。
In order to ensure separating effect, it is preferable that adsorbent and aqueous solution of nitric acid mixing and absorption under room temperature (25 ± 5 DEG C),
Adsorption time is 25~180min.Mixing and absorption carries out under oscillating condition, oscillation rate 120-150rpm.
In aqueous solution of nitric acid, the concentration of metal ion and the concentration of nitric acid can influence separating effect, it is preferable that nitric acid
In aqueous solution, the concentration per metal ion species is 5.0 × 10-4~1.0 × 10-3M.In aqueous solution of nitric acid, the concentration of nitric acid is
0.4~6M.
Contain Pd (II) and other metal ions in the aqueous solution of nitric acid, other metal ions are Li (I), Na (I), K
(I)、Rb(I)、Cs(I)、Ca(Ⅱ)、Mg(Ⅱ)、Sr(Ⅱ)、Ba(Ⅱ)、Nd(Ⅱ)、Ni(Ⅱ)、Co(Ⅱ)、La(Ⅲ)、Ru
(III), at least one of Yb (III), Y (III), Fe (III), Zr (IV), Mo (VI).
The present invention utilizes the method for nitrogenous material adsorbing separation palladium in use, it is not necessary to adds other organic compounds
Thing, selectivity is good, and separating rate is fast, easy to operate, easy to spread.
Brief description of the drawings
The nuclear-magnetism that Fig. 1 is compound CA-BTPhen in embodiment 1 characterizes collection of illustrative plates；
Fig. 2 is compound CA-BTPhen in embodiment 113C NMR spectras；
The MSI-MS that Fig. 3 is compound CA-BTPhen in embodiment 1 characterizes collection of illustrative plates；
Fig. 4 is the distribution coefficient using adsorbent separating element palladium from aqueous solution of nitric acid of embodiment 4 with concentration of nitric acid
The graph of a relation of change；
Fig. 5 is the distribution coefficient using adsorbent separating element palladium from aqueous solution of nitric acid of embodiment 4 with time of contact
The graph of a relation of change.
Embodiment
Embodiment 1
The synthetic route of the present embodiment is as follows：
The synthesis step of the present embodiment includes：
(1) 4.5g camphorquinones (i.e. compound III) are placed in 500mL single-necked flasks, add 250mL THF and dissolved
Obtain golden transparent solution；
(2) 4.5g 2.9- diformamide hydrazone -1,10- o-phenanthrolins are added into step 1 resulting solution under agitation
(i.e. compounds Ⅳ) and 24.0mL catalyst of triethylamine (TEA) form mixed solution, are stirred at reflux reaction 7 days, (thin using TLC
Layer chromatography) tracking reaction is until raw material stops after the reaction was complete.
(3) after reaction stops, it is cooled to room temperature and filters out solid impurity, filtrate obtains grease through rotating away solvent,
Use ethyl acetate/petroleum ether (volume ratio 2:1) solvent is used as, by silica gel column chromatography isolation technics separate pure
Change, purified components obtain bright yellow solid 1.3g, i.e. compound ii (CA-BTPhen), yield 20% after 80 DEG C of vacuum drying.
The structure of compound CA-BTPhen is characterized as below：
(a)1H NMR(400MHz,CDCl3,298K)
In 25 DEG C in deuterochloroform, the CA-BTPhen compounds of synthesis are tested1H NMR spectras, as shown in Figure 1,
Wherein each peak is attributed to：
δ(ppm):8.83 (d, J=8.3Hz, 2H), 8.42 (d, J=8.4Hz, 2H), 8.03 (s, 2H), 3.54 (d, J=
3.6Hz, 2H), 2.04 (d, J=5.1Hz, 4H, after adding heavy water, it is active H that peak, which disappears), 1.74 (s, 4H), 1.49 (d, J=
5.2Hz,4H),0.99(s,12H),0.83(s,6H)。
It is the proton peak of deuterochloroform at δ=7.2ppm in Fig. 1, unimodal at δ=5.3ppm is in methylene chloride
The peak that proton is formed, chemical shift and numbers of hydrogen atoms etc. point out result and are consistent with the structural information of CA-BTPhen.
(b)13C NMR(101MHz,CDCl3,298K)
In 25 DEG C in deuterochloroform, the 1H NMR spectras of the CA-BTPhen compounds of synthesis are tested, as shown in Fig. 2,
Wherein each carbon atom peak is attributed to：
δ(ppm):207.62,165.30,158.62,150.47,144.31,137.08,130.81,127.91,
122.30,58.76,48.68,44.72,30.88,24.20,20.97,17.87,9.12。
Carbon spectrum qualification result is to show that the compound molecule has containing the different carbon of 17 chemical environments in the compound
The symmetry of height, as a result identical with target compound structure, the compound for illustrating synthesis is target compound.
(c)MSI-MS
The MS-ESI positive spectrums of CA-BTPhen are tested in methanol solution, the result is shown in Fig. 3, analysis result shows：
[M+H+]=591.6, [M+Na+]=613.5, calculated value m/z are 590.6.The theoretical molecular of CA-BTPhen is 590.6, this
As a result the theoretical value with CA-BTPhen molecular weight is consistent, and MS-ESI interpretations of result explanation successfully synthesizes target compound.
Embodiment 2
Compound CA-BTPhen prepared by 0.5 gram of embodiment 1 is dissolved in 70.0mL dichloromethane, is fully dissolved
To golden solution；4.5 grams of SiO are added into this golden solution2- P is stirred evenly, and makes SiO2- P is uniformly mixed with compound,
Make dichloromethane volatilization most of to material to nearly dry state, in capillarity and physisorption through depressurizing rotary evaporation
Under organic molecule is entered SiO2In-P apertures, then the material of nearly dry state is dried in vacuo 24h at 45 DEG C again, obtains
CA-BTPhen/SiO2- P composite materials, i.e. adsorbent.
Embodiment 3
Compound CA-BTPhen prepared by 0.5 gram of embodiment 1 is dissolved in 75.0mL dichloromethane, is fully dissolved
To golden solution；4.0 grams of SiO are added into this golden solution2- P is stirred evenly, and makes SiO2- P is uniformly mixed with compound,
Make dichloromethane volatilization most of to material to nearly dry state, in capillarity and physisorption through depressurizing rotary evaporation
Under organic molecule is entered SiO2In-P apertures, then the material of nearly dry state is dried in vacuo 24h at 50 DEG C again, obtains
CA-BTPhen/SiO2- P composite materials, i.e. adsorbent.
Embodiment 4
Compound CA-BTPhen prepared by 0.5 gram of embodiment 1 is dissolved in 80.0mL dichloromethane, is fully dissolved
To golden solution；5.0 grams of SiO are added into this golden solution2- P is stirred evenly, and makes SiO2- P is uniformly mixed with compound,
Make dichloromethane volatilization most of to material to nearly dry state, in capillarity and physisorption through depressurizing rotary evaporation
Under organic molecule is entered SiO2In-P apertures, then the material of nearly dry state is dried in vacuo 24h at 55 DEG C again, obtains
CA-BTPhen/SiO2- P composite materials, i.e. adsorbent.
Embodiment 5~11
(1) by alkali metal salt LiNO3、NaNO3、KNO3、RbNO3、CsNO3；Alkali salt Mg (NO3)2、Ca(NO3)2、Sr
(NO3)2、Ba(NO3)2；Transition metal salt Fe (NO3)3、(NH4)6Mo7O24·4H2O、ZrO(NO3)2、Co(NO3)2、Ni(NO3)2；
Precious metals pd (5%w/w) nitrate solution, the nitrate solution of Ru；Rare-earth oxide Y2O3, rare-earth metal nitrate La
(NO3)3、Yb(NO3)3And Nd (NO3)3Deng 20 kinds of metal salts, it is dissolved in salpeter solution addition deionized water and is configured to contain at the same time
The aqueous solution of nitric acid of various metals ion, the concentration of nitric acid in aqueous solution of nitric acid are 4.0M, the concentration of each metal ion for 2.0~
5.0×10-3M。
(2) concentrated nitric acid and deionized water are added in aqueous solution of nitric acid, adjusts the concentration of nitric acid difference in aqueous solution of nitric acid
For 0.4,1.0,2.0,3.0,4.0,5.0,6.0M, the concentration per metal ion species is 5.0 × 10-4M。
(3) aqueous solution for the different concentration of nitric acid containing 20 kinds of metallic elements for obtaining step (2) is prepared with embodiment 2
Adsorbent contact mixing, amount ratio during mixing is：0.15g adsorbents are corresponded to per 3.0mL aqueous solution of nitric acid；
(4) mixed liquor obtained by step (3) is subjected to adsorption experiment, oscillator vibration on TAITECMM-10 type oscillators
Speed is 150rpm, is operated under room temperature 298K, and adsorption time 180min, makes absorption reach balance, then before and after measurement absorption,
The content of each metallic element in different aqueous solution of nitric acid.
For the absorption result of embodiment 5~11 as shown in figure 4, abscissa is concentration of nitric acid in Fig. 4, ordinate is segregative line
Number.As seen from Figure 4, when concentration of nitric acid is 0.4M, the effect of separating element palladium is best, and the adsorption rate of palladium is higher than 99%,
And it is less than 6 for other 19 metal ion species distribution coefficients, illustrate that adsorbent provided by the invention is strong to palladium-selective, be adapted to use
In carrying out efficiently separating recycling to palladium from containing multiple metallic element water phase, application range is extremely wide.
Embodiment 12~17
Experiment condition and step are same as Example 5, and difference is, by aqueous solution of nitric acid, concentration of nitric acid is solid
Be set to 0.4M, change successively time of contact for 1,2,20,30,80,120min, gained separating resulting is as shown in figure 5, horizontal in Fig. 5
Coordinate is concentration of nitric acid, and ordinate is separation.
As seen from Figure 5, when contacting between when being 20min, the absorption to palladium has had reached equilibrium state, the suction of palladium
Attached rate is higher than 99%, and is less than 6 for other 19 metal ion species distribution coefficients, illustrates that adsorbent provided by the invention selects palladium
Selecting property is strong, is suitable for that palladium is carried out from containing multiple metallic element water phase to efficiently separate recycling, application range is extremely wide.
Claims (7)
- A kind of 1. method using nitrogenous material adsorbing separation palladium, it is characterised in that include the following steps：By adsorbent with containing The aqueous solution of nitric acid of various metals ion mixes, and the palladium ion in aqueous solution of nitric acid is adsorbed by adsorbent separation, the adsorbent It is made of compound loaded as shown in structural formula I on carrier：IWherein, R C1-C10Straight chain alkyl substituent, C1-C10Cycloalkanes base class substituent or C1-C10Benzene ring substitution group；Every gram of adsorbent is mixed with 20 ~ 30 milliliters of aqueous solution of nitric acid；The carrier is the macro-pore SiO of coated polymer2, the mass ratio of compound and carrier as shown in structural formula I is 1：8~10.
- 2. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 1, it is characterised in that the adsorbent is by such as Compound loaded shown in formula II is made on carrier：II。
- 3. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 1, it is characterised in that in aqueous solution of nitric acid, Concentration per metal ion species is 5.0 × 10-4~1.0×10-3M。
- 4. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 1, it is characterised in that in aqueous solution of nitric acid, The concentration of nitric acid is 0.4 ~ 6M.
- 5. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 1, it is characterised in that the system of the adsorbent Preparation Method is as follows：Compound as shown in structural formula I is dissolved in dichloromethane, carrier is added in resulting solution and is uniformly mixed, through rotation Be evaporated it is dry after, obtain adsorbent.
- 6. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 5, it is characterised in that every gram such as structural formula I Shown compound is dissolved in 130 ~ 150 milliliters of dichloromethane.
- 7. the method for nitrogenous material adsorbing separation palladium is utilized as claimed in claim 1, it is characterised in that adsorbent and nitric acid aqueous solution Mixing and absorption, adsorption time are 25 ~ 180min to solution at room temperature.
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| CN108998672B (en) * | 2018-08-02 | 2019-09-20 | 浙江大学 | A kind of method of separate palladium |
| CN109179550B (en) * | 2018-08-02 | 2019-10-29 | 浙江大学 | A method of using adsorbent from acidic aqueous solution separate palladium |
| CN109182776B (en) * | 2018-08-02 | 2019-10-25 | 浙江大学 | A method of the separate palladium from acidic aqueous solution |
| CN112593088B (en) * | 2020-12-11 | 2021-11-16 | 浙江大学 | Method for adsorbing and separating noble metal palladium |
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| CN101690853A (en) * | 2009-10-19 | 2010-04-07 | 浙江大学 | Method for separating element Pd from high-level radioactive waste |
| JP4521498B2 (en) * | 2007-05-14 | 2010-08-11 | 独立行政法人産業技術総合研究所 | Sulfur compound adsorbent and method for producing the same |
| CN104762489A (en) * | 2015-04-22 | 2015-07-08 | 浙江大学 | Method for separating palladium ion from multi-metallic ion aqueous solution |
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| JP4521498B2 (en) * | 2007-05-14 | 2010-08-11 | 独立行政法人産業技術総合研究所 | Sulfur compound adsorbent and method for producing the same |
| CN101690853A (en) * | 2009-10-19 | 2010-04-07 | 浙江大学 | Method for separating element Pd from high-level radioactive waste |
| CN104762489A (en) * | 2015-04-22 | 2015-07-08 | 浙江大学 | Method for separating palladium ion from multi-metallic ion aqueous solution |
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