CN102140089B - Thiacalix [8] arene diethyl acetamide as well as synthesis method and application thereof - Google Patents

Thiacalix [8] arene diethyl acetamide as well as synthesis method and application thereof Download PDF

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CN102140089B
CN102140089B CN2011100435921A CN201110043592A CN102140089B CN 102140089 B CN102140089 B CN 102140089B CN 2011100435921 A CN2011100435921 A CN 2011100435921A CN 201110043592 A CN201110043592 A CN 201110043592A CN 102140089 B CN102140089 B CN 102140089B
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cup
sulfo
aromatic hydrocarbons
diethyl
acetamide
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CN102140089A (en
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李春斌
岳玉莲
刘宝全
王剑峰
范圣第
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DALIAN JINGUIYUAN TECHNOLOGY DEVELOPMENT Co Ltd
Dalian Minzu University
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DALIAN JINGUIYUAN TECHNOLOGY DEVELOPMENT Co Ltd
Dalian Nationalities University
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

The invention provides thiacalix [8] arene diethyl acetamide as well as a synthesis method and application thereof. The synthesis method comprises the following steps: modifying the lower edge of thiacalix [8] arene (TC8A) by using caesium carbonate as a catalyst and taking the TC8A and N,N-diethyl-2-chloroacetamide as substrates so as to synthesize a TC8A derivative, namely thiacalix [8] arene diethyl acetamide. The study of extraction on an automobile purification catalyst solution containing night metal ions indicates that when the pH value is 3.0, TC8A-CH2CON (CH2CH3)2 has a high selective recognition capability on zirconium ions in a metal mixed liquid, extraction rate can reach 96.7%; and when the pH is 4.0, the extraction rate of TC8A-CH2CON (CH2CH3)2 on palladium ions in the metalmixed liquid can reach 44.5%. The rare metal extractant produced by the invention is a white powder, is stable in property, and is convenient for use.

Description

Sulfo-cup [8] aromatic hydrocarbons diethyl acetamide and preparation method and use thereof
Technical field
The invention provides a kind of rare metal extraction agent and preparation method and use thereof, this metal extraction agent can separate different metal ions from the rare metal mixed solution.
Background technology
Along with the arrival of industrial age, the discharging of vehicle exhaust has become the main source of atmospheric pollution.The Global Auto recoverable amount is approximately 1,000,000,000 at present, and China will break through 7,000 ten thousand.First since on automobile, the exhaust purification catalytic convertor being installed, this became the most effective external purification control method of improvement automobile exhaust pollution that Global Access is used from the U.S. in 1974.The emission standard of vehicle NOx has improved in United States Government from the eighties in last century, thereby generation and the development of vehicle tail gas cleaning catalyst have been promoted, the three-way catalyst that contains the platinum metals (Platinum-group metals, PGM) such as platinum, palladium and rhodium arises at the historic moment.As well-known three-way catalyst, PGM can reduce the discharging of vehicle exhaust 99%.The platinum metals is very limited at natural content regrettably, therefore recycles the platinum metals and seem very important from discarded cleaning catalyst for tail gases of automobiles, as someone reports leaching PGM from discarded cleaning catalyst for tail gases of automobiles residue.The industrial also reagent such as own thioether, trioctylamine or tributyl phosphate commonly used come the selective extraction precious metal ion from basic metal, but unfortunately these reagent are difficult to these precious metals are separated individually, therefore need exploitation one class can separate individually the reagent of certain precious metal from the precious metal mixed solution.
Calixarene is the macrocylc compound that is formed by phenol units and formaldehyde condensation, itself has closely adjacent a plurality of hydroxyls and a π system hole, makes calixarene and derivative thereof form title complex with various metals.a kind of four methylene radical in fragrant four hydrocarbon of cup of classics are replaced by sulphur in 1997 and synthetic sulfo-cup [4] aromatic hydrocarbons (thiacalix[4] arean, TC4A) simple and easy method is implemented, along with going deep into of research, the structural performance that it is found that coupling sulphur is fully different from methylene radical with the characteristic of domination electronics, and because coupling sulphur contains non-shared electron pair, make Thiacalixarenes greatly improve the affinity of metal ion, utilize the Thiacalixarenes characteristic high to the metal ion affinity, synthetic dissimilar Thiacalixarenes derivative, come the platinum in the vehicle tail gas catalyzer, rhodium, the rare metals such as palladium carry out respectively that solely selective recovery is significant.
Summary of the invention
1, the technical problem to be solved in the present invention is:
1. synthesize a kind of novel compound: sulfo-cup [8] aromatic hydrocarbons diethyl acetamide
2. the synthetic method of sulfo-cup [8] aromatic hydrocarbons diethyl acetamide is provided
3. a kind of purposes of sulfo-cup [8] aromatic hydrocarbons diethyl acetamide is disclosed: recycle rare metal from discarded cleaning catalyst for tail gases of automobiles.
2, technical scheme of the present invention is as follows:
Sulfo-cup [8] aromatic hydrocarbons diethyl acetamide (TC[8] A-CH 2CON (CH 2CH 3) 2), structural formula is as follows:
Figure BDA0000047708120000021
Sulfo-cup [8] aromatic hydrocarbons diethyl acetamide (TC[8] A-CH 2CON (CH 2CH 3) 2) the building-up reactions formula as follows:
Figure BDA0000047708120000022
Add N in acetone soln, N-diethyl-2-chlor(o)acetamide and sodium iodide, under 20-25 ℃, reaction added sulfo-cup [8] aromatic hydrocarbons (sulfo-cup [8] aromatic hydrocarbons is TC8A) and uses water-soluble cesium carbonate after 2 hours, described N, N-diethyl-2-chlor(o)acetamide, sodium iodide, sulfo-cup [8] aromatic hydrocarbons, cesium carbonate and the mol ratio that is used for the water of dissolving cesium carbonate are 1: 1: 0.06: 0.75: 100; Reflux 48 hours, TLC detects sulfo-cup [8] aroamtic hydrocarbon raw material point and disappears, and reaction is carried out rotary evaporation after finishing, and gets resultant I, then adds the chloroform dissolving resultant I of resultant I50 times volume, gets chloroformic solution; Use respectively with the isopyknic 2 mol/L hydrochloric acid of chloroformic solution and distilled water chloroformic solution is respectively extracted 2 times, abandon after water chloroformic solution with anhydrous sodium sulfate drying and carry out rotary evaporation and remove chloroform, obtain to add again the acetone of 50 times of product volumes to obtain white precipitate after product, sedimentation and filtration and vacuum-drying got white powder TC[8] A-CH 2CON (CH 2CH 3) 2
A kind of purposes of sulfo-cup [8] aromatic hydrocarbons diethyl acetamide:
Sulfo-cup [8] aromatic hydrocarbons diethyl acetamide is used for recycling rare metal from discarded cleaning catalyst for tail gases of automobiles as extraction agent, in particular for reclaiming zirconium ion wherein, discarded cleaning catalyst for tail gases of automobiles is obtained containing the metallic solution of precious metal (as platinum, rhodium, palladium etc.) after with the strong acid dissolution filter, during use, sulfo-cup [8] aromatic hydrocarbons diethyl acetamide is dissolved in chloroformic solution, can carries out to the zirconium ion in metallic solution the extraction of high selectivity.Total concentration of metal ions mol ratio in sulfo-cup [8] aromatic hydrocarbons diethyl acetamide and metallic solution is 1: 1 o'clock best results.
Description of drawings
Fig. 1 is synthetic product TC[8 of the present invention] A-CH 2CON (CH 2CH 3) 2Jointly grind infrared spectrogram after compressing tablet with potassium bromide crystal, at 2963 places be-CH as seen from Figure 1 3Characteristic peak, 2874 places are-the CN characteristic peak, and 1647 places are the C=O characteristic peak, and 1468 places are-CH 2,-CH 3Characteristic peak, 1385 places are-the CH characteristic peak, and 1221 places are the Ar-O characteristic peak, and 1092 places are the Ar-O-C characteristic peak, can determine that thus this compound contains phenyl ring, Ar-O, C=O, CH 2, CH 3Deng group.
Fig. 2 is synthetic product TC[8 of the present invention] A-CH 2CON (CH 2CH 3) 2At CDCl 3In hydrogen spectrum nmr spectrum, chemical shift 7.11 places are 16 H on phenyl ring, integrated value is 1.00, chemical shift 4.74 places are OCH 216 H of CO, integrated value is 1.04; Chemical shift 3.38,3.42 places are-(NCH 2CH 3) 2In 2 CH 232 H, integrated value is respectively 1.05 and 1.09; Chemical shift 1.11,1.01 places are-N (CH 2CH 3) 2In 2 CH 348 H, integrated value is respectively 1.52 and 1.55; Chemical shift 1.08 places are C (CH 3) 3In 3 CH 372 H, integrated value is 4.78.
TC[8 in theory] A-CH 2CON (CH 2CH 3) 2The ratio of the number of middle H is:
[ArH∶OCH 2CO∶N(CH 2CH 3) 2∶N(CH 2CH 3) 2∶C(CH 3) 3]
[1∶1∶2(1+1)∶3(1.5+1.5)∶4.5]
1HNMR is measured as [1: 1.04: (1.07+1.09): (1.52+1.55): (4.78)].
Fig. 3 is synthetic product TC[8 of the present invention] A-CH 2CON (CH 2CH 3) 2At CDCl 3In carbon spectrum nmr spectrum, chemical shift 13.3,14.7 places are-N (CH 2CH 3) 2In, 2 CH 3In C, chemical shift 31.5 places are-C (CH 3) 3In 3 CH 3In C, chemical shift 34.4 places are-C (CH 3) 3In season C, chemical shift 40.2,41.6 places are-(CH 2CH 3) 2In 2 CH 2In C, chemical shift 69.4 places are-OCH 2Carbon, chemical shift 127.9 places are 2 C that are connected with S on phenyl ring, chemical shift 133.0 places are the C that is not connected with any substituting group on phenyl ring, chemical shift 145.9 places be on phenyl ring with the C that the tertiary butyl is connected, chemical shift 158.1 places are the C that is connected with O on phenyl ring, chemical shift 166.8 places are-and C on CO.
Fig. 4 is synthetic product TC[8 of the present invention] A-CH 2CON (CH 2CH 3) 2Mass spectrogram, TC[8] A-CH 2CON (CH 2CH 3) 2Theoretical molecular be 2347.4, the molecular weight of mass spectroscopy is 2349.6.
Fig. 5 is invention synthetic product TC[8] A-CH 2CON (CH 2CH 3) 2(C 128H 184O 16N 8S 8) ultimate analysis raw data, TC[8 in theory] A-CH 2CON (CH 2CH 3) 2Middle C content is 65.49%; H content is 7.90%; N content is that 4.77%. experiment survey C content is 65.09%; H content is 7.80%; N content is 4.24%.
The product that provable the present invention of infrared spectra, proton nmr spectra, carbon-13 nmr spectra, mass spectrum and ultimate analysis of the invention synthetic product that is shown by Fig. 1-5 synthesizes is TC[8 really] A-CH 2CON (CH 2CH 3) 2
Fig. 6 is invention synthetic product TC[8] A-CH 2CON (CH 2CH 3) 2The pH value that contains nine metal ion species is respectively 1.0,1.5, and 2.0,3.0,4.0 cleaning catalyst for tail gases of automobiles GOLD FROM PLATING SOLUTION belong to the extraction results of ion, are 3.0 o'clock TC8A-CH at pH as seen from Figure 6 2CON (CH 2CH 3) 2Wherein zirconium ion is had the highest selectivity recognition capability, and percentage extraction can reach 96.7%, is 4.0 o'clock TC8A-CH at pH 2CON (CH 2CH 3) 2Percentage extraction to wherein palladium ion can reach 44.5%.
Embodiment
Embodiment
Add N in acetone soln, N-diethyl-2-chlor(o)acetamide and sodium iodide, under 20-25 ℃, reaction added sulfo-cup [8] aromatic hydrocarbons and uses water-soluble cesium carbonate after 2 hours, N, the mol ratio of N-diethyl-2-chlor(o)acetamide, sodium iodide, sulfo-cup [8] aromatic hydrocarbons, cesium carbonate and water is 1: 1: 0.06: 0.75: 100; Reflux 48 hours, TLC detects sulfo-cup [8] aroamtic hydrocarbon raw material point and disappears, and reaction is carried out rotary evaporation after finishing, and gets resultant, then adds the chloroform dissolving resultant of 50 times of volumes of resultant, gets chloroformic solution; Use respectively with the isopyknic 2 mol/L hydrochloric acid of chloroformic solution and distilled water chloroformic solution is respectively extracted 2 times, abandon after water chloroformic solution with anhydrous sodium sulfate drying and carry out rotary evaporation and remove chloroform, obtain to add again the acetone of 50 times of product volumes to obtain white precipitate after product, sedimentation and filtration and vacuum-drying got white powder TC[8] A-CH 2CON (CH 2CH 3) 2, productive rate 61.5%.
Product is carried out infrared spectra, proton nmr spectra, carbon-13 nmr spectra, mass spectrum and ultimate analysis detect, get spectrogram such as Fig. 1-5.Can determine product be sulfo-cup [8] the aromatic hydrocarbons diethyl acetamide described in summary of the invention part (TC[8] A-CH 2CON (CH 2CH 3) 2).
Extraction test: the abandoned car tai-gas clean-up catalyst under dismounting on abandoned car is ground, is crushed to 40 orders, get the 500g powder with containing 1vol%H 2O 2Concentrated hydrochloric acid 1000ml filter after extracting 3 hours under 65 ℃ and obtain PGM stoste.Get PGM stoste and be used for afterwards extraction research with 50 times of distilled water dilutings.Adopt inductively coupled plasma atomic emission spectrometer (ICP-AES) to measure (measurement result sees Table 1) to the concentration that the PGM GOLD FROM PLATING SOLUTION belongs to ion.The pH of PGM solution regulates by 6 mol/L hydrochloric acid or 5 mol/L sodium hydroxide.Prepare the TC[8 of 10 milliliters 2.92 mM/ls] A-CH 2CON (CH 2CH 3) 25 parts of chloroformic solutions, respectively from the dilution of five kinds of different pH after 10 milliliters of PGM solution be put in a vial and stir, the speed that at room temperature turns with per minute 900 stirs carried out liquid-liquid extraction in 24 hours, after extraction finishes, the concentration of aqueous phase metal ion adopts ICP-AES to measure, each extraction experiments repeats 2 times, and measurement result is got mean value 3 times.
Advantage and effect
We have studied TC[8] A-CH 2CON (CH 2CH 3) 2The effect of extracting that the PGM GOLD FROM PLATING SOLUTION is belonged to ion, formula 1 and 2 are seen in the calculating of percentage extraction E%, extraction results is seen Fig. 6
E%=[organic phase concentration of metal ions]/[aqueous metal ionic concn before extraction] * 100%1;
[organic phase concentration of metal ions]=[aqueous metal ionic concn before extraction]-[aqueous metal ionic concn after extraction] 2.
Table 1 PGM GOLD FROM PLATING SOLUTION belongs to composition and the concentration of ion
Figure BDA0000047708120000051
The cleaning catalyst for tail gases of automobiles solution that contains nine metal ion species is extracted studies show that, is TC8A-CH in 3.0 o'clock extraction liquids at pH 2CON (CH 2CH 3) 2Wherein zirconium ion is had the highest selectivity recognition capability, and percentage extraction can reach 96.7%, is TC8A-CH in 4.0 o'clock extraction liquids at pH 2CON (CH 2CH 3) 2Percentage extraction to wherein palladium ion can reach 44.5%.

Claims (4)

1. sulfo-cup [8] aromatic hydrocarbons diethyl acetamide, molecular formula TC[8] A-CH 2CON (CH 2CH 3) 2, structural formula is as follows:
Figure FDA00002733205300011
2. the synthetic method of sulfo-cup as claimed in claim 1 [8] aromatic hydrocarbons diethyl acetamide, its concrete steps are as follows:
Add N in acetone soln, N-diethyl-2-chlor(o)acetamide and sodium iodide, under 20-25 ℃, reaction added sulfo-cup [8] aromatic hydrocarbons and uses water-soluble cesium carbonate after 2 hours, described N, N-diethyl-2-chlor(o)acetamide, sodium iodide, sulfo-cup [8] aromatic hydrocarbons, cesium carbonate and the mol ratio that is used for the water of dissolving cesium carbonate are 1 ︰ 1 ︰ 0.06 ︰ 0.75 ︰ 100; Reflux 48 hours, TLC detects sulfo-cup [8] aroamtic hydrocarbon raw material point and disappears, and reaction is carried out rotary evaporation after finishing, and gets the resultant I, then adds the chloroform dissolving resultant I of 50 times of volumes of resultant I, gets chloroformic solution; Use respectively with the isopyknic 2 mol/L hydrochloric acid of chloroformic solution and distilled water chloroformic solution is respectively extracted 2 times, abandon after water chloroformic solution with anhydrous sodium sulfate drying and carry out rotary evaporation and remove chloroform, obtain to add again the acetone of 50 times of product volumes to obtain white precipitate after product, sedimentation and filtration and vacuum-drying got white powder TC[8] A-CH 2CON (CH 2CH 3) 2
Described sulfo-cup [8] aromatic hydrocarbons has following structure:
Figure FDA00002733205300021
3. sulfo-cup as claimed in claim 1 [8] aromatic hydrocarbons diethyl acetamide reclaims the purposes of rare metal from discarded cleaning catalyst for tail gases of automobiles as extraction agent.
4. sulfo-cup as claimed in claim 1 [8] aromatic hydrocarbons diethyl acetamide as the extracting process of extraction agent, grinds the abandoned car tai-gas clean-up catalyst under dismounting on abandoned car, be crushed to 40 orders, gets the 500g powder with containing 1vol%H 2O 2Concentrated hydrochloric acid 1000ml filter after extracting 3 hours under 65 ℃ and obtain PGM stoste, get PGM stoste and be used for afterwards extraction research with 50 times of distilled water dilutings; Adopt inductively coupled plasma atomic emission spectrum ICP-AES that the concentration that the PGM GOLD FROM PLATING SOLUTION belongs to ion is measured; The pH of PGM solution regulates by 6 mol/L hydrochloric acid or 5 mol/L sodium hydroxide; Prepare the TC[8 of 10 milliliters 2.92 mM/ls] A-CH 2CON (CH 2CH 3) 2Chloroformic solution is put in a vial with 10 milliliters of PGM solution after the dilution of pH3.0 and stirs, and the speed that at room temperature turns with per minute 900 stirs carried out liquid-liquid extraction in 24 hours.
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CN105671332B (en) * 2016-02-04 2018-06-22 浙江大学 A kind of method using column arene derivatives extraction and separation palladium ion
CN105837554B (en) * 2016-05-06 2018-05-15 河北科技大学 The synthetic method of 1,3,5- trithian derivatives
CN106478617A (en) * 2016-08-28 2017-03-08 谢长江 A kind of sulphur bridge is oxidized and lower edge contains thio cup [4] arene derivatives and its synthetic method and the application of picolyl amides
CN106632292A (en) * 2016-08-28 2017-05-10 谢长江 Thiacalix [4] aromatic acylhydrazone Schiff base derivative and synthetic method and application thereof

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