高效亲CO_2开链冠醚螯合剂的分子设计、合成及应用
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摘要
重金属污染的治理和贵重金属的回收,日益成为世界各国关注的焦点问题之一。传统有机溶剂萃取金属离子易造成环境的二次污染。超临界CO2萃取技术环境友好、清洁绿色,在金属离子处理领域具有巨大的应用潜力。但是,超临界CO2不能直接溶解金属离子,需要借助亲CO2的螯合剂才能达到萃取金属离子的目的。大量实验表明,在超临界CO2萃取金属离子中含氟螯合剂的效率最高,但其高应用成本和强生物毒性阻碍了规模化应用。所以,开发设计高效的无氟螯合剂分子成为当前该领域的研究热点,也是该领域研究的挑战。传统设计无氟螯合剂的思路因过度关注螯合剂分子本身对CO2的亲和能力,所得螯合剂分子往往在超临界CO2中的溶解度很高,但是超临界CO2螯合萃取金属离子的效率低下,甚至不能实现萃取。因此,采用新的设计思路非常必要。
本文采用量子化学和真实溶剂似导体屏蔽模型(COSMO-RS)计算的方法,研究了金属螯合物La(p-二酮)3与CO2分子间的相互作用规律。结果表明,在含氟体系中,具有强吸电子作用-CF3基团能够有效地分散集中在螯合内核上的极性电子,起到了降低金属螯合物极性的作用；同时,C-F键强偶极矩与CO2四极矩之间发生的强偶极-四极矩相互作用,进一步增强了含氟金属螯合物对CO2的亲和性。在此基础上,提出了新的设计思路：当金属离子与螯合剂形成螯合物时,金属离子上的正电荷能够直接并有效分散在整个金属螯合物体系中以避免形成高极性中心,进而降低整个体系的极性；同时借助不参与配位的供体位点与CO2分子之间的特异作用,如路易斯酸(LA)-路易斯碱(LB)相互作用,进一步提高非氟金属螯合物的亲C02能力。据此构建了系列具有开链冠醚结构的有机磷类螯合剂分子,(MeO)(RO)P(O)-Xn-OP(O)(OR)(OMe),其中,Xn为中间桥链：-(OCH2CH2)n-或-(OCH(CH3)CH2)n-,n=2、3、4；R为端基侧链：正辛基、2-乙基己基或含有醚氧单元的长链基。COSMO-RS计算表明,在La(Ⅲ)的螯合物体系中,桥链能够有效分散La3+的正电荷,并且未参与配位的O原子(P-O-C基团)能够促进与CO2分子的作用,从而提高了螯合物分子对CO2的亲和能力。
采用溶剂催化法制备了此系列螯合剂,其中以POCl3低聚乙二醇或低聚丙二醇、长链醇、甲醇、三乙胺为反应原料、以甲苯为反应溶剂、以1H-四氮唑为催化剂,经过三步反应,粗产物经硅胶柱层析分离提纯(洗脱剂：丙酮/二氯甲烷),螯合剂的最终收率为22-47%。1H-NMR、13C-NMR、APCI-MS和元素分析等表征结果显示螯合剂分子结构正确。
采用静态浊点法测定了温度(313.15至333.15K)和压力(10至22MPa)范围内,螯合剂在超临界C02中的浊点压力和溶解度。在实验范围内,新螯合剂的摩尔分率溶解度均在10-3数量级,显示螯合剂具有良好的C02亲和能力。半经验Bartle模型对溶解度数据的拟合结果与实验结果能够良好吻合。另外,利用COSMO-RS计算了C02在以-(OCH2CH2)n-为桥链的螯合剂中的亨利常数(KH,298.15K),1/KH的大小顺序能够反映桥链长度对螯合剂溶解度的影响规律,即n越小,螯合剂在scCO2中的溶解度越高,1/KH越大。在此基础上,进一步计算发现,与含O的结构单元相比,含S的结构单元更有利于增强分子对CO2的亲和性；含N的硝基基团比乙酰基基团更有利于提高分子对CO2的亲和能力。这为设计亲CO2的分子提供了新的重要信息。
采用静态原位萃取的方式,在313K,20MPa条件下,初步考察了利用超临界CO2和新系列螯合剂从滤纸上萃取La3+、Gd3+和yb3+等三种镧系金属离子的效率。结果表明：(1)在不借助有机改性剂或含氟反离子的条件下,螯合剂萃取效率可达80%,与含氟的螯合剂萃取效率具有一定可比性,例如六氟乙酰丙酮(hfa)对La3+的萃取效率为70%(萃取条件：333K,15MPa,5%甲醇,静态与动态萃取耦合方式)；(2)桥链单元数量n=3或4的螯合剂萃取效率高于nn=2的螯合剂萃取效率；(3)此外,桥链对螯合剂的萃取选择性具有重要影响,如n=2时,螯合剂对La展现了高萃取选择性,而n=3或4时,螯合剂对镧系中部的Gd有一定选择性。金属螯合物的FT-IR光谱和量子化学计算结果表明,金属离子对螯合剂分子配位前的优势构象扰动越小,两者的亲和性越强,萃取选择性越高。
The control of heavy metal pollution and the recycling of precious metals have increasingly become a hot issue in the world. Supercritical CO2(scCO?) is a promising alternative to the traditional organic solvents in the treatments of metals, due to its green features. However, the CO2-philic chelating ligands are necessary for scCO2extraction of metal ions. Up to now, it has been acknowledged that the fluorinated chelating ligands are quite superior to the non-fluorinated ones. Unfortunately, the high cost and environmental toxicity hampered their large-scale application. As a result, it is highly desirable to develop new efficient non-fluorinated chelating ligands for scCO2, but it is still a challenge job in this field. It could afford CO2-philic ligands by simply attaching CO2-philic non-fluorinated groups to the chelating heads, however, which generally exhibited low scCO2extraction efficiency of metal ions, because of much more emphasis on the CO2affinity of the free ligands in the designing process. Therefore, the new design methodology is quite necessary.
A deeper insight into the impact of F-based groups on the interactions between the La((3-diketone)3chelates and CO2has been achieved by quantum chemistry and COSMO-RS calculations. It was clearly found that (1) the most negative F atoms can effectively disperse the trapped electrons in the highly polar chelation core, leading to the reduced polarity of the system;(2) the-CF3groups could enthapically enhance the CO2-philicity of metal chelates through the electrostatic interactions between the highly dipolar C-F bonds and the quadrupolar CO2. Subsequently, a new strategy for designing non-fluorinated ligands for scCO2was proposed by the combination of both concepts:(1) The positive charges on the central metal cation could be dispersed among the metal chelate system, avoiding highly-polar center;(2) The non-chelating donors could interact with CO2molecule, e.g. through the specific Lewis Acid (LA)-Lewis base (LB) interactions, energetically enhanced the CO2-philicity of the metal chelate. Accordingly, a series of new neutral organophosphorous open-chain crown ether analogues was designed,(MeO)(RO)P(O)-Xn-OP(O)(OR)(OMe), where the bridging chains X is-(OCH2CH2)n-or-(OCH(CH3)CH2)n-, n=2、3、4; R is the side chain of the phosphoryl group:n-Octyl,2-ethylhexyl and other long chains containing ether oxygen units. The COSMO-RS calculations suggested that the oxygenated bridging chains and the non-chelating O donors (P-O-C groups) in the new La(Ⅲ) chelate systems can provide the two favorable effects above, and subsequently the new ligands can enhance the CO2-philicity of metal chelates.
The new series of chelating ligands were prepared by a modified method involving the catalyst,1H-tetrazole. POCl3, oligo(ethylene glcol)(or oligo(propylene glycol)), long-chained alcohol, methanol and triethylamine were employed as the reactants and toluene was as the reaction solvent. After three reactions steps, the crude products were separated and purified by silica gel column chromatography (acetone/dichloromethane). The final yields of the yellow oils were22-47%. The molecules were characterized by1H-NMR,13C-NMR, APCI-MS and element analysis.
The cloud point pressures and solubilities of chelating ligands in SCCO2were determined by a static method at temperatures from (313.15to333.15) K and over a pressure range of (10to22) MPa. The solubilities of ligands were all high in the10-3orders of magnitude. The values calculated by the Bartle semi-empirical model exhibited good agreement with the experimental data. Additionally, the Henry's constants (KH) of CO2in the new chelating ligands as molecule solvents (298.15K) were calculated by COSMO-RS method. The order of the1/KH was the same with that of the number (n) of oxygenated units in the bridging chains of oligo(ethylene glycol), namely that the smaller n was, the bigger1/KH was, the more CO2-philic the ligands were. Based on the results, COSMO-RS calculations were further performed for the linear molecules containing O, N or S atoms. In terms of the enhancement of the CO2-philicity, the S-based groups were more favorable than O-based groups, and the N-based group,-NO2, was more effective than the acetyl group. This was new important information for designing CO2-philic molecules.
The extractability of the lanthanides (La3+, Gd3+and Yb3+) from the filter paper using scCO2and the new chelating ligands was preliminarily investigated at313K,20MPa by the static in-situ manner. These ligands exhibited high extraction efficiencies (close to80%) even without organic modifiers or fluorinated counter anions, which were much higher than that of tetraethylene glycol, tributyl phosphate and15-crown-5, encouragely, which reached the level of the fluorinated ones, e.g. the extraction efficiency of La3+by hexafluoroacetone (hfa) was70%under the condition:333K,15MPa,5%methanol by the static-dynamic coupling manner. In addition, these ligands showed different selectivities for lanthanide ions, e.g. X=-(OCH2CH2)n-, when n=2, the higher affinity for La3+; when n=3or4, the moderately higher selectivity for Gd3+. The results of quantum chemistry calculations and FT-IR spectroscopy analysis for the metal chelates demonstrated that if the perturbation effect for the pre-organized conformation of ligand caused by the metal ion was weaker, the ligand would present stronger affinity to the corresponding metal ion.
本文采用量子化学和真实溶剂似导体屏蔽模型(COSMO-RS)计算的方法,研究了金属螯合物La(p-二酮)3与CO2分子间的相互作用规律。结果表明,在含氟体系中,具有强吸电子作用-CF3基团能够有效地分散集中在螯合内核上的极性电子,起到了降低金属螯合物极性的作用；同时,C-F键强偶极矩与CO2四极矩之间发生的强偶极-四极矩相互作用,进一步增强了含氟金属螯合物对CO2的亲和性。在此基础上,提出了新的设计思路：当金属离子与螯合剂形成螯合物时,金属离子上的正电荷能够直接并有效分散在整个金属螯合物体系中以避免形成高极性中心,进而降低整个体系的极性；同时借助不参与配位的供体位点与CO2分子之间的特异作用,如路易斯酸(LA)-路易斯碱(LB)相互作用,进一步提高非氟金属螯合物的亲C02能力。据此构建了系列具有开链冠醚结构的有机磷类螯合剂分子,(MeO)(RO)P(O)-Xn-OP(O)(OR)(OMe),其中,Xn为中间桥链：-(OCH2CH2)n-或-(OCH(CH3)CH2)n-,n=2、3、4；R为端基侧链：正辛基、2-乙基己基或含有醚氧单元的长链基。COSMO-RS计算表明,在La(Ⅲ)的螯合物体系中,桥链能够有效分散La3+的正电荷,并且未参与配位的O原子(P-O-C基团)能够促进与CO2分子的作用,从而提高了螯合物分子对CO2的亲和能力。
采用溶剂催化法制备了此系列螯合剂,其中以POCl3低聚乙二醇或低聚丙二醇、长链醇、甲醇、三乙胺为反应原料、以甲苯为反应溶剂、以1H-四氮唑为催化剂,经过三步反应,粗产物经硅胶柱层析分离提纯(洗脱剂：丙酮/二氯甲烷),螯合剂的最终收率为22-47%。1H-NMR、13C-NMR、APCI-MS和元素分析等表征结果显示螯合剂分子结构正确。
采用静态浊点法测定了温度(313.15至333.15K)和压力(10至22MPa)范围内,螯合剂在超临界C02中的浊点压力和溶解度。在实验范围内,新螯合剂的摩尔分率溶解度均在10-3数量级,显示螯合剂具有良好的C02亲和能力。半经验Bartle模型对溶解度数据的拟合结果与实验结果能够良好吻合。另外,利用COSMO-RS计算了C02在以-(OCH2CH2)n-为桥链的螯合剂中的亨利常数(KH,298.15K),1/KH的大小顺序能够反映桥链长度对螯合剂溶解度的影响规律,即n越小,螯合剂在scCO2中的溶解度越高,1/KH越大。在此基础上,进一步计算发现,与含O的结构单元相比,含S的结构单元更有利于增强分子对CO2的亲和性；含N的硝基基团比乙酰基基团更有利于提高分子对CO2的亲和能力。这为设计亲CO2的分子提供了新的重要信息。
采用静态原位萃取的方式,在313K,20MPa条件下,初步考察了利用超临界CO2和新系列螯合剂从滤纸上萃取La3+、Gd3+和yb3+等三种镧系金属离子的效率。结果表明：(1)在不借助有机改性剂或含氟反离子的条件下,螯合剂萃取效率可达80%,与含氟的螯合剂萃取效率具有一定可比性,例如六氟乙酰丙酮(hfa)对La3+的萃取效率为70%(萃取条件：333K,15MPa,5%甲醇,静态与动态萃取耦合方式)；(2)桥链单元数量n=3或4的螯合剂萃取效率高于nn=2的螯合剂萃取效率；(3)此外,桥链对螯合剂的萃取选择性具有重要影响,如n=2时,螯合剂对La展现了高萃取选择性,而n=3或4时,螯合剂对镧系中部的Gd有一定选择性。金属螯合物的FT-IR光谱和量子化学计算结果表明,金属离子对螯合剂分子配位前的优势构象扰动越小,两者的亲和性越强,萃取选择性越高。
The control of heavy metal pollution and the recycling of precious metals have increasingly become a hot issue in the world. Supercritical CO2(scCO?) is a promising alternative to the traditional organic solvents in the treatments of metals, due to its green features. However, the CO2-philic chelating ligands are necessary for scCO2extraction of metal ions. Up to now, it has been acknowledged that the fluorinated chelating ligands are quite superior to the non-fluorinated ones. Unfortunately, the high cost and environmental toxicity hampered their large-scale application. As a result, it is highly desirable to develop new efficient non-fluorinated chelating ligands for scCO2, but it is still a challenge job in this field. It could afford CO2-philic ligands by simply attaching CO2-philic non-fluorinated groups to the chelating heads, however, which generally exhibited low scCO2extraction efficiency of metal ions, because of much more emphasis on the CO2affinity of the free ligands in the designing process. Therefore, the new design methodology is quite necessary.
A deeper insight into the impact of F-based groups on the interactions between the La((3-diketone)3chelates and CO2has been achieved by quantum chemistry and COSMO-RS calculations. It was clearly found that (1) the most negative F atoms can effectively disperse the trapped electrons in the highly polar chelation core, leading to the reduced polarity of the system;(2) the-CF3groups could enthapically enhance the CO2-philicity of metal chelates through the electrostatic interactions between the highly dipolar C-F bonds and the quadrupolar CO2. Subsequently, a new strategy for designing non-fluorinated ligands for scCO2was proposed by the combination of both concepts:(1) The positive charges on the central metal cation could be dispersed among the metal chelate system, avoiding highly-polar center;(2) The non-chelating donors could interact with CO2molecule, e.g. through the specific Lewis Acid (LA)-Lewis base (LB) interactions, energetically enhanced the CO2-philicity of the metal chelate. Accordingly, a series of new neutral organophosphorous open-chain crown ether analogues was designed,(MeO)(RO)P(O)-Xn-OP(O)(OR)(OMe), where the bridging chains X is-(OCH2CH2)n-or-(OCH(CH3)CH2)n-, n=2、3、4; R is the side chain of the phosphoryl group:n-Octyl,2-ethylhexyl and other long chains containing ether oxygen units. The COSMO-RS calculations suggested that the oxygenated bridging chains and the non-chelating O donors (P-O-C groups) in the new La(Ⅲ) chelate systems can provide the two favorable effects above, and subsequently the new ligands can enhance the CO2-philicity of metal chelates.
The new series of chelating ligands were prepared by a modified method involving the catalyst,1H-tetrazole. POCl3, oligo(ethylene glcol)(or oligo(propylene glycol)), long-chained alcohol, methanol and triethylamine were employed as the reactants and toluene was as the reaction solvent. After three reactions steps, the crude products were separated and purified by silica gel column chromatography (acetone/dichloromethane). The final yields of the yellow oils were22-47%. The molecules were characterized by1H-NMR,13C-NMR, APCI-MS and element analysis.
The cloud point pressures and solubilities of chelating ligands in SCCO2were determined by a static method at temperatures from (313.15to333.15) K and over a pressure range of (10to22) MPa. The solubilities of ligands were all high in the10-3orders of magnitude. The values calculated by the Bartle semi-empirical model exhibited good agreement with the experimental data. Additionally, the Henry's constants (KH) of CO2in the new chelating ligands as molecule solvents (298.15K) were calculated by COSMO-RS method. The order of the1/KH was the same with that of the number (n) of oxygenated units in the bridging chains of oligo(ethylene glycol), namely that the smaller n was, the bigger1/KH was, the more CO2-philic the ligands were. Based on the results, COSMO-RS calculations were further performed for the linear molecules containing O, N or S atoms. In terms of the enhancement of the CO2-philicity, the S-based groups were more favorable than O-based groups, and the N-based group,-NO2, was more effective than the acetyl group. This was new important information for designing CO2-philic molecules.
The extractability of the lanthanides (La3+, Gd3+and Yb3+) from the filter paper using scCO2and the new chelating ligands was preliminarily investigated at313K,20MPa by the static in-situ manner. These ligands exhibited high extraction efficiencies (close to80%) even without organic modifiers or fluorinated counter anions, which were much higher than that of tetraethylene glycol, tributyl phosphate and15-crown-5, encouragely, which reached the level of the fluorinated ones, e.g. the extraction efficiency of La3+by hexafluoroacetone (hfa) was70%under the condition:333K,15MPa,5%methanol by the static-dynamic coupling manner. In addition, these ligands showed different selectivities for lanthanide ions, e.g. X=-(OCH2CH2)n-, when n=2, the higher affinity for La3+; when n=3or4, the moderately higher selectivity for Gd3+. The results of quantum chemistry calculations and FT-IR spectroscopy analysis for the metal chelates demonstrated that if the perturbation effect for the pre-organized conformation of ligand caused by the metal ion was weaker, the ligand would present stronger affinity to the corresponding metal ion.
引文
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