离子液体中分子筛催化环已烷氧化反应研究
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摘要
环己烷的氧化在化工生产中具有十分重要的价值。目前,国内外环己烷氧化制备环己醇(酮)的生产工艺中,环己烷的转化率为3.5～4.2%,环己酮和环己醇的总选择性为76～81%。该技术资源利用率低,残渣排放量大。因此,发展一种更为高效和环境友好的催化体系已显得十分重要。近年来开发出的新型催化剂如ZSM-5、钛硅分子筛等在环己烷氧化反应中表现出优异的催化性能,但此类催化剂用于环己烷氧化反应时多采用乙腈、丙酮、乙二酸等挥发性有毒有害溶剂作为反应介质,没有从根本上解决清洁条件下的环己烷氧化反应。以新型绿色溶剂离子液体作为反应介质替代传统溶剂,有望实现温和条件下高转化率及产物高选择性的环己烷氧化反应,最终达到清洁生产的目的。
本文以应用面较宽的咪唑类离子液体作为研究对象。在对离子液体的合成及其物化性质认识的基础上,首次尝试将ZSM-5及TS-1分子筛、叔丁基过氧化氢(TBHP)、离子液体结合组成新的“环境友好”催化氧化体系,即“分子筛—离子液体—TBHP”催化氧化体系。并将此体系用于催化环己烷氧化反应研究,实现了清洁、温和条件下环己烷的高效、高选择性催化氧化反应。
以氮甲基咪唑为原料采用两步法合成了系列1-烷基-3-甲基咪唑四氟硼酸盐([C_(2～7)mim]BF_4)及六氟磷酸盐([C_(4～7)mim]PF_6)室温离子液体,并通过核磁氢谱、红外光谱、质谱等手段对其结构进行了分析及确认。对[C_(2～7)mim]BF_4及[C_(4～7)mim]PF_6系列离子液体的饱和吸水性及表面张力进行了测定,结果表明:[C_(2～7)mim]BF_4系列离子液体的吸水性随着1位氮上取代基碳链的增长而减小,其饱和含水量以[C_2mim]BF_4最多,室温下高达8.114%。[C_(4～7)mim]PF_6系列离子液体的吸水性较差,其饱和含水量均低于0.9%以下;[C_(2～7)mim]BF_4及[C_(4～7)mim]PF_6系列离子液体表面张力γ均随温度的升高而线性下降,同种离子液体的表面张力呈现出较宽的变化范围,如298K下,表面张力值从[C_2mim]BF_4的50.4 mJ/m~2到[C_7mim]BF_4的36.1 mJ/m~2。在相同温度下,两类离子液体的表面张力均随着阳离子咪唑环1位氮上的取代基碳链n的增长而减小。
以系列离子液体为反应介质,TBHP为氧化剂,不同硅铝比ZSM-5分子筛为催化剂进行环己烷氧化,得到了较传统分子溶剂丙酮高的环己烷的氧化活性。同一种离子溶剂中,随着分子筛HZSM-5硅铝比的增加环己烷催化氧化活性逐渐降低。硅铝比为25的ZSM-5分子筛在离子液体介质中显示了最高环己烷催化氧化活性。环己烷转化率最高达15.8%,产物总选择性为97.0%。而在传统分子溶剂丙酮中环己烷转化率为2～4%,产物选择性大幅下降,仅在70.2～74.7%范围之内。与非水溶性离子液体相比,水溶性离子液体中分子筛的氧化活性要高。四氟硼酸盐离子液体中,对同一催化剂来说,随着咪唑环1位氮上取代基链长的增加,其催化活性逐渐降低,其活性顺序为:[C_2mim]~+＞[C_3mim]~+＞[C_4mim]~+＞[C_5mim]~+＞[C_6mim]~+＞[C_7mim]~+。环己烷转化率由[C_2mim]BF_4的15.8%降低为[C_7mim]BF_4的3.10%。
采用等体积浸渍和离子交换两种方法制备的系列不同金属改性的ZSM-5分子筛,并对其进行了XRD、EDX、N_2吸附表征。并以离子液体[C_2mim]BF_4为反应介质,考察了改性ZSM-5分子筛对环己烷氧化反应的影响。结果表明,对于负载量相同的不同金属来说,用等体积浸渍法制备的分子筛的环己烷氧化反应活性相差较大,产物的总收率在9.5～20.5%范围之内,而用离子交换法制备的分子筛的环己烷氧化反应活性相差较小,产物的总收率在15.0～16.5%之间。对于负载量相同的同一种金属来说,不同制备方法得到的金属改性ZSM-5分子筛的环己烷氧化反应活性不同,等体积浸渍法制备的载Ni、Cu、Co金属的ZSM-5的活性要低于相对应的离子交换法制备的分子筛的活性。
以系列离子液体为反应介质,TS-1分子筛为催化剂进行环己烷氧化,得到了较高的环己烷的转化率以及产物的选择性。四氟硼酸盐离子液体溶剂中TS-1催化剂的催化活性均高于分子溶剂丙酮或没有溶剂时的活性。在[C_4mim]PF_6离子液体溶剂中,TS-1的催化活性高于无溶剂时的活性而却低于丙酮溶剂中的催化活性。[C_2mim]BF_4离子液体中,TS-1的催化活性最好,环己烷氧化产物的总收率高达14.9%。
机理研究表明,离子液体中ZSM-5及TS-1分子筛催化环己烷氧化均为自由基链锁反应历程。离子液体/TS-1体系中,离子液体溶剂中高的活性与其能够活化分子筛的活性位有关,即咪唑阳离子2位上酸性的氢与钛氧键相互作用导致Ti-O键的极化,提高催化剂上活性位的Lewis酸性,使过骨架钛与环己基过氧化氢生成的过氧化物物种对环己烷上C-H键的活化作用增强进而提高了环己烷氧化反应活性。
以TS-1、ZSM-5及金属改性ZSM-5分子筛为催化剂,离子液体为溶剂的环己烷氧化反应具有分离过程简单、反应条件温和、离子液体/分子筛的重复使用性好、产物选择性及收率较高、无环境污染等突出特点。因此,“TS-1分子筛—离子液体—TBHP”体系催化氧化环己烷反应比传统分子溶剂体系更具有优势。
Oxidation of cyclohexane is significant and economical to the chemical industry. In the present industrial oxidation process, cyclohexane conversion is about 3.5～4.2% and the selectivity to cyclohexanol and cyclohexanone is 76～81%. The obvious drawback of this process is the high energetic demand and the large volume of effluents. Therefore, it is very important to develop an effective and environmentally benign catalytic system. Recently, molecular sieves such as ZSM-5, titanium silicalite 1 (TS-1) has attracted great interest in the selective oxidation of cyclohexane due to their redox ability, shape-selectivity and recyclable properties. However, most of these reported procedures used volatile organic compounds such as acetonitrile, acetone and acetic acid as molecular solvents. The development of clean catalytic method to performed cyclohexane oxidation selectively has received increasing. Ionic liquids are new generation solvents, which have received great attention as promising substitutes for traditional organic solvents. An effectively and environmentally friendly oxidative conversion of cyclohexane might be realized in ionic liquids compared with in molecular solvents.
In this paper, the most widely used alkylimdazolium-based ionic liquids were synthesized. On the basis of study on their physiochemical properties, ionic liquids were firstly used as solvents in the catalytic oxidation system of "molecular sieves- tert-butyl-hydroperoxide". The new combinations of "molecular sieves-ionic liquid-TBHP" system were firstly applied to the cyclohexane oxidation reaction and the highly effective, environment-friendly oxidation reaction of cyclohexane, which has a high yield and selectivity, was obtained.
A series of room temperature ionic liquids based on 1-alkyl-3-methylimidazolium tetrafluoroborate ([C_(2～7)mim]BF_4) and 1-alkyl-3-methylimidazolium hexafluorophosphate ([C_(4～7)mim]PF_6) were synthesized, and the structures were characterized and confirmed by ~1H NMR, IR and MS. Water adsorption properties and surface tension of the series of ionic liquids were measured. The results show that the amount of saturated water adsorbed in series [C_(2～7)mim]BF_4 ionic liquids drops with increasing alkyl chain length n. Among them, the [C_2mim]BF_4 possessed the highest water adsorption properties and the highest amount of adsorptive water was 8.114% at room temperature. While there is a little amount of saturated water in the series of [C(4～7)mim]PF_6 ionic liquids and they are all lower than 0.9%. There is a linear decrease of surface tension with increasing temperature. The values of surface tension span an unusually wide range for compounds of similar structure, from 50.4 mJ/m~2 ([C_2mim]BF_4) to 36.1 mJ/m~2 ([C_7mim]BF_4) at 298 K. In the sametemperature, the surface tension decreases as the alkyl chain in the 1-position of the cation is lengthened for the two series of ionic liquids.
ZSM-5 molecular sieves with different Si/Al ratio were first applied to catalyze the oxidation of cyclohexane with tert-butyl-hydroperoxide in ionic liquids and acetone. Higher oxidation activities were obtained in ionic liquids than in molecular solvent. In the same ionic solvent, the activity of cyclohexane oxidation decreases with the increase of Si/Al ratio of ZSM-5. the molecular sieves with a Si/Al ratio of 25 shows the highest catalytic activity in [C_2mim]BF_4 and a conversion of 15.8% and a selectivity of 97.0 % of desired products were obtained. While in acetone, the selectivity was sharply decreased and only in the range of 70.2～74.7%. In contrast to the reaction in water-immicible ionic liquids, the cyclohexane oxidation in water-miscible ionic liquids shows higher activity. In the case of tetrafluoroborate ionic liquids, a reduction of activity occurs with increasing cation size for a specific molecular sieve. The order of activity is as follows: [C_2mim]~+ > [C_3mim]~+ > [C_4mim]~+ > [C_5mim]~+ > [C_6mim]~+ > [C_7mim]~+. The conversion of cyclohexane decreases from 15.8% to 3.10%.
Two series of modified ZSM-5 with different metals were prepared by using ion-exchange and incipient wetness impregnation method. The synthesized metal-containing molecular sieves were characterized by XRD, EDX and N_2 adsorption. In ionic liquid [C_2mim]BF_4 media, cyclohexane oxidation reactions were studied using the obtained two series metal-containing ZSM-5 as catalysts. Results indicate that the activities span a relatively wide range for the catalysts prepared by using incipient wetness impregnation method and the total yield was in the range of 9.5～20.5%. While for the catalysts synthesized by ion-exchange, a different results were obtained, and the total yields were in a narrow range of 15.0～16.5%. For the specific metal with the same amount of loading, different preparation method have different influence on their catalytic activity. The activities of ZSM-5 loading Ni、Cu and Co prepared by incipient wetness impregnation method were lower than those of ZSM-5 loading Ni、Cu and Co prepared by ion-exchange method.
The oxidations of cyclohexane with tert-butyl-hydroperoxide catalyzed by TS-1 in series of ionic liquids were performed. A higher cyclohexane conversion and higher selectivity of products were found in the ionic liquid compared with in acetone. The catalytic activities of TS-1 in tetrafluoroborate ionic liquids are higher than those in either molecular solvent acetone or no solvent. In the case of [C_4mim]PF_6, the catalytic activity of TS-1 is higher than that no solvent and lower than that in acetone. There has the highest catalytic activity of TS-1 in ionic liquid [C_2mim]BF_4 and the total yield of oxidation products reaches 14.9%. Cyclohexane oxidation reaction with ZSM-5 and TS-1 molecular sieves in ionic liquids proceeds by free-radical mechanism. For TS-1 catalyst, the higher activity of the ionic liquid compared with the organic solvent may suggest that it can activate the active site on the catalyst and the activation can be understood from consideration of the acidity of 2-H of the imidazolium cation. This interaction induces a polarization of the Ti-0 bond, increasing the overall Lewis acidity of the catalytic site, and, as a consequence, the activity of the peroxo species toward the cyclohexane increases.
The process of cyclohexane oxidation catalyzed by ZSM-5, metal-containing ZSM-5 and TS-1 in ionic liquids has a series of advantages. The mild reaction conditions and the simple product isolation combined with increased reaction rates, ease of recovery and reuse of ZSM-5/ionic liquid system make this procedure useful and attractive for cyclohexane oxidation.
本文以应用面较宽的咪唑类离子液体作为研究对象。在对离子液体的合成及其物化性质认识的基础上,首次尝试将ZSM-5及TS-1分子筛、叔丁基过氧化氢(TBHP)、离子液体结合组成新的“环境友好”催化氧化体系,即“分子筛—离子液体—TBHP”催化氧化体系。并将此体系用于催化环己烷氧化反应研究,实现了清洁、温和条件下环己烷的高效、高选择性催化氧化反应。
以氮甲基咪唑为原料采用两步法合成了系列1-烷基-3-甲基咪唑四氟硼酸盐([C_(2～7)mim]BF_4)及六氟磷酸盐([C_(4～7)mim]PF_6)室温离子液体,并通过核磁氢谱、红外光谱、质谱等手段对其结构进行了分析及确认。对[C_(2～7)mim]BF_4及[C_(4～7)mim]PF_6系列离子液体的饱和吸水性及表面张力进行了测定,结果表明:[C_(2～7)mim]BF_4系列离子液体的吸水性随着1位氮上取代基碳链的增长而减小,其饱和含水量以[C_2mim]BF_4最多,室温下高达8.114%。[C_(4～7)mim]PF_6系列离子液体的吸水性较差,其饱和含水量均低于0.9%以下;[C_(2～7)mim]BF_4及[C_(4～7)mim]PF_6系列离子液体表面张力γ均随温度的升高而线性下降,同种离子液体的表面张力呈现出较宽的变化范围,如298K下,表面张力值从[C_2mim]BF_4的50.4 mJ/m~2到[C_7mim]BF_4的36.1 mJ/m~2。在相同温度下,两类离子液体的表面张力均随着阳离子咪唑环1位氮上的取代基碳链n的增长而减小。
以系列离子液体为反应介质,TBHP为氧化剂,不同硅铝比ZSM-5分子筛为催化剂进行环己烷氧化,得到了较传统分子溶剂丙酮高的环己烷的氧化活性。同一种离子溶剂中,随着分子筛HZSM-5硅铝比的增加环己烷催化氧化活性逐渐降低。硅铝比为25的ZSM-5分子筛在离子液体介质中显示了最高环己烷催化氧化活性。环己烷转化率最高达15.8%,产物总选择性为97.0%。而在传统分子溶剂丙酮中环己烷转化率为2～4%,产物选择性大幅下降,仅在70.2～74.7%范围之内。与非水溶性离子液体相比,水溶性离子液体中分子筛的氧化活性要高。四氟硼酸盐离子液体中,对同一催化剂来说,随着咪唑环1位氮上取代基链长的增加,其催化活性逐渐降低,其活性顺序为:[C_2mim]~+＞[C_3mim]~+＞[C_4mim]~+＞[C_5mim]~+＞[C_6mim]~+＞[C_7mim]~+。环己烷转化率由[C_2mim]BF_4的15.8%降低为[C_7mim]BF_4的3.10%。
采用等体积浸渍和离子交换两种方法制备的系列不同金属改性的ZSM-5分子筛,并对其进行了XRD、EDX、N_2吸附表征。并以离子液体[C_2mim]BF_4为反应介质,考察了改性ZSM-5分子筛对环己烷氧化反应的影响。结果表明,对于负载量相同的不同金属来说,用等体积浸渍法制备的分子筛的环己烷氧化反应活性相差较大,产物的总收率在9.5～20.5%范围之内,而用离子交换法制备的分子筛的环己烷氧化反应活性相差较小,产物的总收率在15.0～16.5%之间。对于负载量相同的同一种金属来说,不同制备方法得到的金属改性ZSM-5分子筛的环己烷氧化反应活性不同,等体积浸渍法制备的载Ni、Cu、Co金属的ZSM-5的活性要低于相对应的离子交换法制备的分子筛的活性。
以系列离子液体为反应介质,TS-1分子筛为催化剂进行环己烷氧化,得到了较高的环己烷的转化率以及产物的选择性。四氟硼酸盐离子液体溶剂中TS-1催化剂的催化活性均高于分子溶剂丙酮或没有溶剂时的活性。在[C_4mim]PF_6离子液体溶剂中,TS-1的催化活性高于无溶剂时的活性而却低于丙酮溶剂中的催化活性。[C_2mim]BF_4离子液体中,TS-1的催化活性最好,环己烷氧化产物的总收率高达14.9%。
机理研究表明,离子液体中ZSM-5及TS-1分子筛催化环己烷氧化均为自由基链锁反应历程。离子液体/TS-1体系中,离子液体溶剂中高的活性与其能够活化分子筛的活性位有关,即咪唑阳离子2位上酸性的氢与钛氧键相互作用导致Ti-O键的极化,提高催化剂上活性位的Lewis酸性,使过骨架钛与环己基过氧化氢生成的过氧化物物种对环己烷上C-H键的活化作用增强进而提高了环己烷氧化反应活性。
以TS-1、ZSM-5及金属改性ZSM-5分子筛为催化剂,离子液体为溶剂的环己烷氧化反应具有分离过程简单、反应条件温和、离子液体/分子筛的重复使用性好、产物选择性及收率较高、无环境污染等突出特点。因此,“TS-1分子筛—离子液体—TBHP”体系催化氧化环己烷反应比传统分子溶剂体系更具有优势。
Oxidation of cyclohexane is significant and economical to the chemical industry. In the present industrial oxidation process, cyclohexane conversion is about 3.5～4.2% and the selectivity to cyclohexanol and cyclohexanone is 76～81%. The obvious drawback of this process is the high energetic demand and the large volume of effluents. Therefore, it is very important to develop an effective and environmentally benign catalytic system. Recently, molecular sieves such as ZSM-5, titanium silicalite 1 (TS-1) has attracted great interest in the selective oxidation of cyclohexane due to their redox ability, shape-selectivity and recyclable properties. However, most of these reported procedures used volatile organic compounds such as acetonitrile, acetone and acetic acid as molecular solvents. The development of clean catalytic method to performed cyclohexane oxidation selectively has received increasing. Ionic liquids are new generation solvents, which have received great attention as promising substitutes for traditional organic solvents. An effectively and environmentally friendly oxidative conversion of cyclohexane might be realized in ionic liquids compared with in molecular solvents.
In this paper, the most widely used alkylimdazolium-based ionic liquids were synthesized. On the basis of study on their physiochemical properties, ionic liquids were firstly used as solvents in the catalytic oxidation system of "molecular sieves- tert-butyl-hydroperoxide". The new combinations of "molecular sieves-ionic liquid-TBHP" system were firstly applied to the cyclohexane oxidation reaction and the highly effective, environment-friendly oxidation reaction of cyclohexane, which has a high yield and selectivity, was obtained.
A series of room temperature ionic liquids based on 1-alkyl-3-methylimidazolium tetrafluoroborate ([C_(2～7)mim]BF_4) and 1-alkyl-3-methylimidazolium hexafluorophosphate ([C_(4～7)mim]PF_6) were synthesized, and the structures were characterized and confirmed by ~1H NMR, IR and MS. Water adsorption properties and surface tension of the series of ionic liquids were measured. The results show that the amount of saturated water adsorbed in series [C_(2～7)mim]BF_4 ionic liquids drops with increasing alkyl chain length n. Among them, the [C_2mim]BF_4 possessed the highest water adsorption properties and the highest amount of adsorptive water was 8.114% at room temperature. While there is a little amount of saturated water in the series of [C(4～7)mim]PF_6 ionic liquids and they are all lower than 0.9%. There is a linear decrease of surface tension with increasing temperature. The values of surface tension span an unusually wide range for compounds of similar structure, from 50.4 mJ/m~2 ([C_2mim]BF_4) to 36.1 mJ/m~2 ([C_7mim]BF_4) at 298 K. In the sametemperature, the surface tension decreases as the alkyl chain in the 1-position of the cation is lengthened for the two series of ionic liquids.
ZSM-5 molecular sieves with different Si/Al ratio were first applied to catalyze the oxidation of cyclohexane with tert-butyl-hydroperoxide in ionic liquids and acetone. Higher oxidation activities were obtained in ionic liquids than in molecular solvent. In the same ionic solvent, the activity of cyclohexane oxidation decreases with the increase of Si/Al ratio of ZSM-5. the molecular sieves with a Si/Al ratio of 25 shows the highest catalytic activity in [C_2mim]BF_4 and a conversion of 15.8% and a selectivity of 97.0 % of desired products were obtained. While in acetone, the selectivity was sharply decreased and only in the range of 70.2～74.7%. In contrast to the reaction in water-immicible ionic liquids, the cyclohexane oxidation in water-miscible ionic liquids shows higher activity. In the case of tetrafluoroborate ionic liquids, a reduction of activity occurs with increasing cation size for a specific molecular sieve. The order of activity is as follows: [C_2mim]~+ > [C_3mim]~+ > [C_4mim]~+ > [C_5mim]~+ > [C_6mim]~+ > [C_7mim]~+. The conversion of cyclohexane decreases from 15.8% to 3.10%.
Two series of modified ZSM-5 with different metals were prepared by using ion-exchange and incipient wetness impregnation method. The synthesized metal-containing molecular sieves were characterized by XRD, EDX and N_2 adsorption. In ionic liquid [C_2mim]BF_4 media, cyclohexane oxidation reactions were studied using the obtained two series metal-containing ZSM-5 as catalysts. Results indicate that the activities span a relatively wide range for the catalysts prepared by using incipient wetness impregnation method and the total yield was in the range of 9.5～20.5%. While for the catalysts synthesized by ion-exchange, a different results were obtained, and the total yields were in a narrow range of 15.0～16.5%. For the specific metal with the same amount of loading, different preparation method have different influence on their catalytic activity. The activities of ZSM-5 loading Ni、Cu and Co prepared by incipient wetness impregnation method were lower than those of ZSM-5 loading Ni、Cu and Co prepared by ion-exchange method.
The oxidations of cyclohexane with tert-butyl-hydroperoxide catalyzed by TS-1 in series of ionic liquids were performed. A higher cyclohexane conversion and higher selectivity of products were found in the ionic liquid compared with in acetone. The catalytic activities of TS-1 in tetrafluoroborate ionic liquids are higher than those in either molecular solvent acetone or no solvent. In the case of [C_4mim]PF_6, the catalytic activity of TS-1 is higher than that no solvent and lower than that in acetone. There has the highest catalytic activity of TS-1 in ionic liquid [C_2mim]BF_4 and the total yield of oxidation products reaches 14.9%. Cyclohexane oxidation reaction with ZSM-5 and TS-1 molecular sieves in ionic liquids proceeds by free-radical mechanism. For TS-1 catalyst, the higher activity of the ionic liquid compared with the organic solvent may suggest that it can activate the active site on the catalyst and the activation can be understood from consideration of the acidity of 2-H of the imidazolium cation. This interaction induces a polarization of the Ti-0 bond, increasing the overall Lewis acidity of the catalytic site, and, as a consequence, the activity of the peroxo species toward the cyclohexane increases.
The process of cyclohexane oxidation catalyzed by ZSM-5, metal-containing ZSM-5 and TS-1 in ionic liquids has a series of advantages. The mild reaction conditions and the simple product isolation combined with increased reaction rates, ease of recovery and reuse of ZSM-5/ionic liquid system make this procedure useful and attractive for cyclohexane oxidation.
引文
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