离子液体酸性气体吸收剂的合成、表征及吸收性能研究
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摘要
工业的飞速发展给人类带来巨大便利的同时,也引发了严重的环境污染问题。在各种行业中,化工以及能源相关产业对环境的污染程度最严重。为了有效地控制并治理因化工生产而造成的污染,绿色化学应运而生,并逐渐成为化工领域的发展趋势。绿色化学的核心内容就是从源头上减少和消除污染物,合理地利用资源和能源并提高循环利用率。
脱除二氧化碳、二氧化硫等酸性气体是一项关乎环境保护、能源利用和化工生产的关键技术。目前,工业上广泛使用有机胺水溶液法、热钾碱法以及石灰石等方法脱除酸性气体。这些工艺技术成熟、成本低、处理量大,但都面临设备腐蚀严重、解吸能耗高、因溶剂挥发而引起二次污染等弊端。离子液体作为绿色化学的重要分支之一,是在室温或相近温度下完全由离子组成的液体物质。离子液体具有几乎无蒸汽压,热稳定性好,分子结构可设计等独特的优势,并在催化、有机合成、萃取分离等众多应用领域逐渐成为研究的热点。若将离子液体作为酸性气体的吸收剂,最大的优势是没有蒸汽压。这将使得离子液体在吸收过程中,不会进入气相。一方面,离子液体不会因为自身的挥发而导致吸收剂的损失；另一方面,解吸后的气体也不会含有吸收液组分。此外,离子液体的结构可设计性特点使其可以按照实际的需求和特殊的目标,设计并合成专用于吸收酸性气体的功能化离子液体。因此,科学界普遍认为离子液体是绿色的、具有光明应用前景的酸性气体吸收剂。
在前人工作的基础上,本文的主要工作是设计并合成了专用于吸收酸性气体的功能化离子液体。分析了离子液体的结构与物理化学性质的规律后,本文选择性地合成了四烷基季胺氨基酸离子液体,其中四乙基季胺L丙氨酸是当时粘度最低的功能化离子液体,且具有良好的CO2吸收性能。在此基础上,继续合成了一系列低粘度的非对称四烷基季胺有机酸离子液体。实验结果表明,全取代有机酸离子液体吸收CO2的容量(以质量比计)高于其他所有功能化离子液体。同时,一取代有机酸离子液体也是首次发现的吸收SO2容量最高、吸收速度最快的功能化离子液体。这些发现证明了从分子结构的角度设计并合成功能化离子液体思路的正确性,极大地推动了离子液体作为绿色高效酸性气体吸收剂的应用。随后,本文选择了合成路线短、粘度低、吸收速率大的功能化离子液体与工业中广泛使用的有机胺—一N-甲基二乙醇胺复配为混合液；研究混合液的物理化学性质与温度的关系以及混合液的吸收性能。希望通过将离子液体作为活化剂使用以减低工业应用成本,并加快离子液体作为酸性气体可逆吸收剂的产业化进程。通过这些工作,本文得到以下结论：
(1)离子液体的粘度与结构的变化规律：通常,增长阳离子的烷基侧链会导致粘度的增高。当烷基链的碳原子数相同时,增多碳链分支将会加大粘度。此外,咪唑环阳离子2号位的甲基化、阳离子侧链的氟化以及阳离子对称性的提高都会增大粘度。阴离子对离子液体的粘度有明显的影响。一般情况下,平面结构的阴离子构成的离子液体粘度较低；而非平面构型、对称性好的阴离子构成的离子液体粘度相对较高。与阳离子类似,增大阴离子的体积和摩尔质量,增长阴离子的侧链长度,也会升高离子液体的粘度。残留的水或有机溶剂也会降低离子液体的粘度,而残余的卤素则会升高粘度。
(2)低粘度的氨基酸离子液体吸收速率大：选择空间伸展性好的四烷基季胺作为阳离子和氨基酸阴离子构成氨基酸功能化离子液体。因阴阳离子之间的空间间隙大,氨基酸阴离子的摩尔质量和体积小,合成的氨基酸离子液体的粘度较文献已报道的功能化离子液体低。其中四乙基季胺L-丙氨酸([N2222][L-Ala])离子液体在25℃时粘度仅为81mPa·s,是当时粘度最低的功能化离子液体。将其作为吸收剂进行CO2吸收的实验结果表明：该离子液体吸收CO2的机理与有机伯胺(如MEA)和仲胺(DEA)以及其他含氨基功能化离子液体(如3-丙胺基-甲基咪唑四氟硼酸盐)类似,均是两分子的吸收剂与一分子的CO2生成氨基甲酸盐类化合物。低粘度的氨基酸离子液体吸收CO2的速率大,是有机胺的2至5倍。高吸收速率是因为离子液体较低的粘度,有利于CO2在液相中的扩散和传质。并且,合成氨基酸离子液体属于酸碱中和一步反应法,合成过程简单,成本较低,纯度较高。因此,该类型的离子液体在酸性气体吸收领域有潜在的应用价值。
(3)全取代有机酸离子液体具有较高的CO2吸收容量：根据阳离子结构与离子液体粘度的规律,选择非对称四烷基季胺—丁基三乙基季胺([N2224])为阳离子,以合成粘度更低的离子液体；选择有机酸作为阴离子,以降低合成成本。本文有目标地合成了非对称性四烷基季胺有机酸([N2224][carboxylate])离子液体。该离子液体易和水结合,处于盐-水复合物的状态。因为水的存在,全取代有机酸离子液体的粘度较低,但热稳定性较差。研究结果表明：水和阴离子有一定的作用力,水与盐的摩尔配比越小,相互作用力越大。吸收CO2的实验结果表明：全取代有机酸离子液体表现出较强的CO2亲和力,[N2224][CH3COO]的吸收容量比其他以有机酸为阴离子的所有离子液体高。此外,吸收实验结果还表明：有机酸阴离子的摩尔质量越大,有机官能团越多,吸收CO2的能力越弱；温度越高,吸收容量越低；水含量越高,吸收容量越低。
(4)一取代有机酸离子液体具有优异的SO2吸收性能：选择二元有机酸作为阴离子时,若只中和阴离子中的一个活性氢,就可获得非对称四烷基季胺一取代有机酸([N2224][H-carboxylate])离子液体。该离子液体的粘度比全取代有机酸离子液体高,但其热稳定性好。吸收SO2的实验结果表明：[N2224][H-carboxylate]是目前吸收SO2耗时最短、吸收容量最高的功能化离子液体。吸收机理的研究结果表明：SO2破坏了离子液体中原本的分子间氢键,并作为媒介帮助两个羧基形成一个以分子内氢键为主体的八元环结构,该环结构在高温和真空条件下不稳定,故而SO2的解吸率高,离子液体重复吸收性能优良。虽然一取代有机酸离子液体具有较强的SO2亲和力,但由于其本身的弱酸性,该离子液体吸收CO2的能力很弱(甚至比普通离子液体还低),这一研究表明了一取代有机酸离子液体具有应用于分离SO2和CO2的潜在优势。
(5)离子液体与MDEA混合液的物理性质独特,吸收C02性能优良：本文选择了三类离子液体作为添加剂与MDEA复配为混合吸收液,分别是[emim][BF4],[N1111][Gly]知[N2222][L-Ala]。按照不同摩尔配比制备的混合液物理化学性质独特,表现出与纯MDEA或是纯离子液体不同的变化规律。首先,混合液的密度并非随温度的升高而线性地下降；混合吸收液的体积膨胀系数较小,表明了温度对混合液的体积影响较弱；不同配方混合液的超额摩尔体积均为负值,表明了各组分之间发生了有效地分子结构堆积。其次,不同于纯有机溶剂,混合液的粘度随温度的变化规律并不符合阿仑尼乌斯公式,而符合Vogel-Tammann-Fulchers公式。最后,即使纯离子液体与混合液所表现出相似的表面张力值,但表面张力受温度的影响却不相同。MDEA与离子液体混合液的表面张力受温度的影响更小。且添加离子液体可以一定程度上抑制MDEA水溶液的挥发性。
离子液体在混合液中起到活化剂的作用：一方面,可提供活性质子氢,参与到化学反应中,提高混合液的吸收容量和吸收速率；另一方面,离子液体可以抑制MDEA和水的挥发性,提高生产过程中的绿色性,降低设备腐蚀程度和解吸能耗。吸收实验结果表明：[emim][BF4]作为普通离子液体与纯MDEA混合后,混合液吸收性能类似于MDEA水溶液的吸收性能,证明了[emim][BF4]作为物理溶剂和MDEA复配应用于工业吸收的前景；添加[N1111][Gly]和[Nzzzz][L-Ala]氨基酸功能化离子液体在低压条件下(小于0.3MPa)可以促进混合液的吸收容量；升高温度使得混合液的吸收容量略有下降,却可以极大地提高混合液的吸收速率；无论添加何种离子液体,均可有效地增大吸收速率；添加氨基酸功能化离子液体更易提高混合液的吸收速率。
Although benefiting from fast development of economy, we unfortunately also had to face up the serious environmental pollution problems. Among all kinds of industries, chemical and energy-related ones make the most important contributions to the pollution. In order to control and fix the pollution from the chemical and energy-related industries, the concept of green chemistry, which focuses on avoiding pollutants before they are produced and using resource reasonably and reversibly, has been proposed and attracted significant interest in the decades.
The removal of acidic gases, such as carbon dioxide (CO2), sulfur dioxide (SO2) is of significant importance for environmental protection, effective fuel utilization and chemical processes. Nowadays, technologies of trapping CO2using aqueous organic amines, inorganic base solutions and limestone as absorbents have extensively carried out in the chemical plants. However, these technologies often accompanied with resource consumption due to the irreversible reaction of absorbents with CO2(in case of inorganic base solutions and limestone) or organic pollutants releasing to the atmosphere and aqua-sphere (in case of aqueous organic amines). Additionally, high operation costs and large consumption of energy are also drawbacks of these processes. As an alternative to traditional organic solvents, ionic liquids (ILs) provoke a wide interest in scientific community and industrial fields, involving its applications in organic synthesis, catalysis, supercritical fluid reaction and gas separation due to their outstanding characteristics such as negligible vapor pressure, high thermal stability and so on. Comparing to the volatile amines as sequestering agents, ILs possess the non-volatile and thermal stable characteristics that make them environmentally benign gas absorbents without causing concurrent loss of the liquid into the gas and then polluting the environment. Some pioneering works have shown that ILs could reversibly trap acidic gases with high capacities. Inspired by these works, this paper designed and synthesized novel task-specific ionic liquids in order to capture acidic gases. For the first time, novel TSILs (such as [N2222][L-Ala]) with the low viscosity were prepared, which have shown good peformance of trapping CO2. Then, TSILs composed of asymmetric tetraalkylammnoium and carboxylic acid were synthesized. It is interesting to find that the full-deprotonted carboxylate ILs have the largest absorption capacity of CO2, while the half-deprotonted ones can effetively trap SO2even though they are weak acidic. These results have proved that the idea of designing and preparing TSILs for the separation of the acidic gases is worth to study in the future and the TSILs with amino acid or carboxylate anions are very attractive for industrial applications. After characterization of the physical chemical parameters and the determination of the absorption properties, ILs with advantages such as easy to prepare, low viscosity and high absorption rate were chosen to be additive species blended with aqueous organic amines (MDEA). Then, the physical chemical parameters such as density, viscosity and surface tension of the blended absorbents were determined as well as the absorption properties. Experimental results have shown that adding ILs into MDEA is a promising way to utilize ILs in the industry without large operation cost. Several important conclusions have been obtained and summarized as follows:
(1) The relation between the viscosity and the structure of the ILs:normally, the addition of carbon atoms and brunches in the cation, as well as methyl group on the2-C in imidazolium cation and fluorination of the carbon atoms can enlarge the viscosity. The structure of anions has most important effects on the viscosity. The symmetric anions will arise the viscosity, while the two dimensional ones can decrease the viscosity. Assembling to the cation, large volume and molar mass of the anions as well as the enlargement of the carbon length will cause high viscosity. The viscosity will be diminished when water and other organic solvents are present in ILs, whereas reverse effects occur due to the remaining halide.
(2) Amino acid ILs with low viscosity have large absorption rate. After consideration of the relation between the structure of the ions and the viscosity, we chose tetraalkylammonium and amino acid to construct ILs. Because of the large space between the cation and anion, and small size of the anions, the amino acid ILs have smaller viscosities than other functionalized ILs. The lowest viscosity of81mPa s at25℃belongs to [N2222][L-Ala] which has been chosen to determine the absorption prosperities. The absorption results have shown that the reaction mechanism between [N2222][L-Ala] and CO2was similar to that of organic amines (MEA or DEA) and amino-functionalized ILs ([p-NH2mim][BF4]), but with about2to5times larger absorption rate than the amines. Large absorption rate is the result of the low viscosity, which can improve the mass transfer of CO2in the liquid phase. In addition, the synthesis of amino acid ILs was simple and the final products were of high purity. In this case, amino acid ILs are considered as green, effective absorbents of potential use for CO2separation.
(3) Full-deprotonated dicarboxylic acid ILs have large CO2absorption capacity. In order to have ILs with lower viscosity and lower cost, asymmetric tetraalkylammonium cation ([N2224]) and carboxylic acids were used to synthesis carboxylate ILs. It is found that these type anions have the hydrophilic nature and the water interacts with the anions. Because of the water, the ILs have low viscosity but suffer poor thermal stability. Experimental absorption results have shown that the carboxylate ILs have large CO2affinity and have almost the highest capacity than any other ILs based on carboxylic acids. It is further proved that the large molar mass of the anion, high water content, high absorption temperature, and other functional groups are negative effects to the absorption capacity.
(4) Half-deprotonated dicarboxylic acid ILs have excellent SO2absorption properties. If one proton H atom in the dicarboxylic acid is merely neutralized, half-deprotonated carboxylic acid (H-carboxylate) ILs can be prepared. Experimental results have shown that these ILs have higher viscosities and more stable at high temperature than the full-deprotonated ones. It is interestingly found that H-carboxylate ILs have more attractive SO2absorption properties than any other TSILs. The reaction mechanism between ILs and SO2indicated that the SO2interruptted the original inter-molecular hydrogen bond and helped to form intra-molecular hydrogen bond through an octatomic ring, which also made the viscosity diminished after absorption. Additionally, this kind of ILs has low CO2affinity because of the weak acidic nature. These results strongly confirm that H-carboxylate ILs will be of significant importance for the separation of acidic gases from each other.
(5) The mixture of MDEA and ILs show unique physical chemical properties and good performance of absorbing CO2. After thoughtful consideration, three ILs [emim][BF4],[N1111][Gly] and [N2222][L-Ala] have been chosen to blend with MDEA. The physical chemical properties such as density, viscosity and surface tension of the mixtures are quite different from neither pure MDEA nor pure ILs. The densities of the mixtures decreased not linearly with the rising temperature. Small coefficient of expansion indicates that the temperature has minor effect on the volume of mixture. At the same time, the excess molar volumes of all mixtures are negative values, implying that MDEA and the ILs have strong interaction and the molecular cumulated effectively. Unlike pure organic solvents, the relation between the viscosity of the mixture and the temperature can not be correlated by Arrhenius Equation but can be fitted to Vogel-Tammann-Fulchers Equation. Although the values of the surface tension is very close between the mixture and pure ILs, the temperature shows less importance to affect the surface tension of the mixture, making the mixture more attractive to the industrial applications. The ILs play a role as accelerant in the mixture from two aspects. Firstly, ILs take part in the chemical absorption process by providing active hydrogen which can accelerate the absorption rate. Secondly, ILs have no vapor pressure which can restrain the volatility of the MDEA and water, making the process more environmental benign. The experimental results have shown that the mixture composed by [emim][BF4] and MDEA act almost like aqueous MDEA mixtures, which proves the possibility of [emim][BF4] application as physical solvent but with outstanding ILs advantages. Task-specific ionic liquids, such as [N1111][Gly] and [N2222][L-Ala] can enlarge the absorption capacity at low partial pressure of CO2, and accelerate the absorption process significantly. Although the mixture trap less CO2at higher temperature, but the absorption rate would be very large due to the rising temperature.
脱除二氧化碳、二氧化硫等酸性气体是一项关乎环境保护、能源利用和化工生产的关键技术。目前,工业上广泛使用有机胺水溶液法、热钾碱法以及石灰石等方法脱除酸性气体。这些工艺技术成熟、成本低、处理量大,但都面临设备腐蚀严重、解吸能耗高、因溶剂挥发而引起二次污染等弊端。离子液体作为绿色化学的重要分支之一,是在室温或相近温度下完全由离子组成的液体物质。离子液体具有几乎无蒸汽压,热稳定性好,分子结构可设计等独特的优势,并在催化、有机合成、萃取分离等众多应用领域逐渐成为研究的热点。若将离子液体作为酸性气体的吸收剂,最大的优势是没有蒸汽压。这将使得离子液体在吸收过程中,不会进入气相。一方面,离子液体不会因为自身的挥发而导致吸收剂的损失；另一方面,解吸后的气体也不会含有吸收液组分。此外,离子液体的结构可设计性特点使其可以按照实际的需求和特殊的目标,设计并合成专用于吸收酸性气体的功能化离子液体。因此,科学界普遍认为离子液体是绿色的、具有光明应用前景的酸性气体吸收剂。
在前人工作的基础上,本文的主要工作是设计并合成了专用于吸收酸性气体的功能化离子液体。分析了离子液体的结构与物理化学性质的规律后,本文选择性地合成了四烷基季胺氨基酸离子液体,其中四乙基季胺L丙氨酸是当时粘度最低的功能化离子液体,且具有良好的CO2吸收性能。在此基础上,继续合成了一系列低粘度的非对称四烷基季胺有机酸离子液体。实验结果表明,全取代有机酸离子液体吸收CO2的容量(以质量比计)高于其他所有功能化离子液体。同时,一取代有机酸离子液体也是首次发现的吸收SO2容量最高、吸收速度最快的功能化离子液体。这些发现证明了从分子结构的角度设计并合成功能化离子液体思路的正确性,极大地推动了离子液体作为绿色高效酸性气体吸收剂的应用。随后,本文选择了合成路线短、粘度低、吸收速率大的功能化离子液体与工业中广泛使用的有机胺—一N-甲基二乙醇胺复配为混合液；研究混合液的物理化学性质与温度的关系以及混合液的吸收性能。希望通过将离子液体作为活化剂使用以减低工业应用成本,并加快离子液体作为酸性气体可逆吸收剂的产业化进程。通过这些工作,本文得到以下结论：
(1)离子液体的粘度与结构的变化规律：通常,增长阳离子的烷基侧链会导致粘度的增高。当烷基链的碳原子数相同时,增多碳链分支将会加大粘度。此外,咪唑环阳离子2号位的甲基化、阳离子侧链的氟化以及阳离子对称性的提高都会增大粘度。阴离子对离子液体的粘度有明显的影响。一般情况下,平面结构的阴离子构成的离子液体粘度较低；而非平面构型、对称性好的阴离子构成的离子液体粘度相对较高。与阳离子类似,增大阴离子的体积和摩尔质量,增长阴离子的侧链长度,也会升高离子液体的粘度。残留的水或有机溶剂也会降低离子液体的粘度,而残余的卤素则会升高粘度。
(2)低粘度的氨基酸离子液体吸收速率大：选择空间伸展性好的四烷基季胺作为阳离子和氨基酸阴离子构成氨基酸功能化离子液体。因阴阳离子之间的空间间隙大,氨基酸阴离子的摩尔质量和体积小,合成的氨基酸离子液体的粘度较文献已报道的功能化离子液体低。其中四乙基季胺L-丙氨酸([N2222][L-Ala])离子液体在25℃时粘度仅为81mPa·s,是当时粘度最低的功能化离子液体。将其作为吸收剂进行CO2吸收的实验结果表明：该离子液体吸收CO2的机理与有机伯胺(如MEA)和仲胺(DEA)以及其他含氨基功能化离子液体(如3-丙胺基-甲基咪唑四氟硼酸盐)类似,均是两分子的吸收剂与一分子的CO2生成氨基甲酸盐类化合物。低粘度的氨基酸离子液体吸收CO2的速率大,是有机胺的2至5倍。高吸收速率是因为离子液体较低的粘度,有利于CO2在液相中的扩散和传质。并且,合成氨基酸离子液体属于酸碱中和一步反应法,合成过程简单,成本较低,纯度较高。因此,该类型的离子液体在酸性气体吸收领域有潜在的应用价值。
(3)全取代有机酸离子液体具有较高的CO2吸收容量：根据阳离子结构与离子液体粘度的规律,选择非对称四烷基季胺—丁基三乙基季胺([N2224])为阳离子,以合成粘度更低的离子液体；选择有机酸作为阴离子,以降低合成成本。本文有目标地合成了非对称性四烷基季胺有机酸([N2224][carboxylate])离子液体。该离子液体易和水结合,处于盐-水复合物的状态。因为水的存在,全取代有机酸离子液体的粘度较低,但热稳定性较差。研究结果表明：水和阴离子有一定的作用力,水与盐的摩尔配比越小,相互作用力越大。吸收CO2的实验结果表明：全取代有机酸离子液体表现出较强的CO2亲和力,[N2224][CH3COO]的吸收容量比其他以有机酸为阴离子的所有离子液体高。此外,吸收实验结果还表明：有机酸阴离子的摩尔质量越大,有机官能团越多,吸收CO2的能力越弱；温度越高,吸收容量越低；水含量越高,吸收容量越低。
(4)一取代有机酸离子液体具有优异的SO2吸收性能：选择二元有机酸作为阴离子时,若只中和阴离子中的一个活性氢,就可获得非对称四烷基季胺一取代有机酸([N2224][H-carboxylate])离子液体。该离子液体的粘度比全取代有机酸离子液体高,但其热稳定性好。吸收SO2的实验结果表明：[N2224][H-carboxylate]是目前吸收SO2耗时最短、吸收容量最高的功能化离子液体。吸收机理的研究结果表明：SO2破坏了离子液体中原本的分子间氢键,并作为媒介帮助两个羧基形成一个以分子内氢键为主体的八元环结构,该环结构在高温和真空条件下不稳定,故而SO2的解吸率高,离子液体重复吸收性能优良。虽然一取代有机酸离子液体具有较强的SO2亲和力,但由于其本身的弱酸性,该离子液体吸收CO2的能力很弱(甚至比普通离子液体还低),这一研究表明了一取代有机酸离子液体具有应用于分离SO2和CO2的潜在优势。
(5)离子液体与MDEA混合液的物理性质独特,吸收C02性能优良：本文选择了三类离子液体作为添加剂与MDEA复配为混合吸收液,分别是[emim][BF4],[N1111][Gly]知[N2222][L-Ala]。按照不同摩尔配比制备的混合液物理化学性质独特,表现出与纯MDEA或是纯离子液体不同的变化规律。首先,混合液的密度并非随温度的升高而线性地下降；混合吸收液的体积膨胀系数较小,表明了温度对混合液的体积影响较弱；不同配方混合液的超额摩尔体积均为负值,表明了各组分之间发生了有效地分子结构堆积。其次,不同于纯有机溶剂,混合液的粘度随温度的变化规律并不符合阿仑尼乌斯公式,而符合Vogel-Tammann-Fulchers公式。最后,即使纯离子液体与混合液所表现出相似的表面张力值,但表面张力受温度的影响却不相同。MDEA与离子液体混合液的表面张力受温度的影响更小。且添加离子液体可以一定程度上抑制MDEA水溶液的挥发性。
离子液体在混合液中起到活化剂的作用：一方面,可提供活性质子氢,参与到化学反应中,提高混合液的吸收容量和吸收速率；另一方面,离子液体可以抑制MDEA和水的挥发性,提高生产过程中的绿色性,降低设备腐蚀程度和解吸能耗。吸收实验结果表明：[emim][BF4]作为普通离子液体与纯MDEA混合后,混合液吸收性能类似于MDEA水溶液的吸收性能,证明了[emim][BF4]作为物理溶剂和MDEA复配应用于工业吸收的前景；添加[N1111][Gly]和[Nzzzz][L-Ala]氨基酸功能化离子液体在低压条件下(小于0.3MPa)可以促进混合液的吸收容量；升高温度使得混合液的吸收容量略有下降,却可以极大地提高混合液的吸收速率；无论添加何种离子液体,均可有效地增大吸收速率；添加氨基酸功能化离子液体更易提高混合液的吸收速率。
Although benefiting from fast development of economy, we unfortunately also had to face up the serious environmental pollution problems. Among all kinds of industries, chemical and energy-related ones make the most important contributions to the pollution. In order to control and fix the pollution from the chemical and energy-related industries, the concept of green chemistry, which focuses on avoiding pollutants before they are produced and using resource reasonably and reversibly, has been proposed and attracted significant interest in the decades.
The removal of acidic gases, such as carbon dioxide (CO2), sulfur dioxide (SO2) is of significant importance for environmental protection, effective fuel utilization and chemical processes. Nowadays, technologies of trapping CO2using aqueous organic amines, inorganic base solutions and limestone as absorbents have extensively carried out in the chemical plants. However, these technologies often accompanied with resource consumption due to the irreversible reaction of absorbents with CO2(in case of inorganic base solutions and limestone) or organic pollutants releasing to the atmosphere and aqua-sphere (in case of aqueous organic amines). Additionally, high operation costs and large consumption of energy are also drawbacks of these processes. As an alternative to traditional organic solvents, ionic liquids (ILs) provoke a wide interest in scientific community and industrial fields, involving its applications in organic synthesis, catalysis, supercritical fluid reaction and gas separation due to their outstanding characteristics such as negligible vapor pressure, high thermal stability and so on. Comparing to the volatile amines as sequestering agents, ILs possess the non-volatile and thermal stable characteristics that make them environmentally benign gas absorbents without causing concurrent loss of the liquid into the gas and then polluting the environment. Some pioneering works have shown that ILs could reversibly trap acidic gases with high capacities. Inspired by these works, this paper designed and synthesized novel task-specific ionic liquids in order to capture acidic gases. For the first time, novel TSILs (such as [N2222][L-Ala]) with the low viscosity were prepared, which have shown good peformance of trapping CO2. Then, TSILs composed of asymmetric tetraalkylammnoium and carboxylic acid were synthesized. It is interesting to find that the full-deprotonted carboxylate ILs have the largest absorption capacity of CO2, while the half-deprotonted ones can effetively trap SO2even though they are weak acidic. These results have proved that the idea of designing and preparing TSILs for the separation of the acidic gases is worth to study in the future and the TSILs with amino acid or carboxylate anions are very attractive for industrial applications. After characterization of the physical chemical parameters and the determination of the absorption properties, ILs with advantages such as easy to prepare, low viscosity and high absorption rate were chosen to be additive species blended with aqueous organic amines (MDEA). Then, the physical chemical parameters such as density, viscosity and surface tension of the blended absorbents were determined as well as the absorption properties. Experimental results have shown that adding ILs into MDEA is a promising way to utilize ILs in the industry without large operation cost. Several important conclusions have been obtained and summarized as follows:
(1) The relation between the viscosity and the structure of the ILs:normally, the addition of carbon atoms and brunches in the cation, as well as methyl group on the2-C in imidazolium cation and fluorination of the carbon atoms can enlarge the viscosity. The structure of anions has most important effects on the viscosity. The symmetric anions will arise the viscosity, while the two dimensional ones can decrease the viscosity. Assembling to the cation, large volume and molar mass of the anions as well as the enlargement of the carbon length will cause high viscosity. The viscosity will be diminished when water and other organic solvents are present in ILs, whereas reverse effects occur due to the remaining halide.
(2) Amino acid ILs with low viscosity have large absorption rate. After consideration of the relation between the structure of the ions and the viscosity, we chose tetraalkylammonium and amino acid to construct ILs. Because of the large space between the cation and anion, and small size of the anions, the amino acid ILs have smaller viscosities than other functionalized ILs. The lowest viscosity of81mPa s at25℃belongs to [N2222][L-Ala] which has been chosen to determine the absorption prosperities. The absorption results have shown that the reaction mechanism between [N2222][L-Ala] and CO2was similar to that of organic amines (MEA or DEA) and amino-functionalized ILs ([p-NH2mim][BF4]), but with about2to5times larger absorption rate than the amines. Large absorption rate is the result of the low viscosity, which can improve the mass transfer of CO2in the liquid phase. In addition, the synthesis of amino acid ILs was simple and the final products were of high purity. In this case, amino acid ILs are considered as green, effective absorbents of potential use for CO2separation.
(3) Full-deprotonated dicarboxylic acid ILs have large CO2absorption capacity. In order to have ILs with lower viscosity and lower cost, asymmetric tetraalkylammonium cation ([N2224]) and carboxylic acids were used to synthesis carboxylate ILs. It is found that these type anions have the hydrophilic nature and the water interacts with the anions. Because of the water, the ILs have low viscosity but suffer poor thermal stability. Experimental absorption results have shown that the carboxylate ILs have large CO2affinity and have almost the highest capacity than any other ILs based on carboxylic acids. It is further proved that the large molar mass of the anion, high water content, high absorption temperature, and other functional groups are negative effects to the absorption capacity.
(4) Half-deprotonated dicarboxylic acid ILs have excellent SO2absorption properties. If one proton H atom in the dicarboxylic acid is merely neutralized, half-deprotonated carboxylic acid (H-carboxylate) ILs can be prepared. Experimental results have shown that these ILs have higher viscosities and more stable at high temperature than the full-deprotonated ones. It is interestingly found that H-carboxylate ILs have more attractive SO2absorption properties than any other TSILs. The reaction mechanism between ILs and SO2indicated that the SO2interruptted the original inter-molecular hydrogen bond and helped to form intra-molecular hydrogen bond through an octatomic ring, which also made the viscosity diminished after absorption. Additionally, this kind of ILs has low CO2affinity because of the weak acidic nature. These results strongly confirm that H-carboxylate ILs will be of significant importance for the separation of acidic gases from each other.
(5) The mixture of MDEA and ILs show unique physical chemical properties and good performance of absorbing CO2. After thoughtful consideration, three ILs [emim][BF4],[N1111][Gly] and [N2222][L-Ala] have been chosen to blend with MDEA. The physical chemical properties such as density, viscosity and surface tension of the mixtures are quite different from neither pure MDEA nor pure ILs. The densities of the mixtures decreased not linearly with the rising temperature. Small coefficient of expansion indicates that the temperature has minor effect on the volume of mixture. At the same time, the excess molar volumes of all mixtures are negative values, implying that MDEA and the ILs have strong interaction and the molecular cumulated effectively. Unlike pure organic solvents, the relation between the viscosity of the mixture and the temperature can not be correlated by Arrhenius Equation but can be fitted to Vogel-Tammann-Fulchers Equation. Although the values of the surface tension is very close between the mixture and pure ILs, the temperature shows less importance to affect the surface tension of the mixture, making the mixture more attractive to the industrial applications. The ILs play a role as accelerant in the mixture from two aspects. Firstly, ILs take part in the chemical absorption process by providing active hydrogen which can accelerate the absorption rate. Secondly, ILs have no vapor pressure which can restrain the volatility of the MDEA and water, making the process more environmental benign. The experimental results have shown that the mixture composed by [emim][BF4] and MDEA act almost like aqueous MDEA mixtures, which proves the possibility of [emim][BF4] application as physical solvent but with outstanding ILs advantages. Task-specific ionic liquids, such as [N1111][Gly] and [N2222][L-Ala] can enlarge the absorption capacity at low partial pressure of CO2, and accelerate the absorption process significantly. Although the mixture trap less CO2at higher temperature, but the absorption rate would be very large due to the rising temperature.
引文
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