五氟碘乙烷的气相催化合成研究
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摘要
五氟碘乙烷(C2F5I)具有很高的反应活性和特殊的物理化学性能,它是制备多种合成树脂单体、憎水剂、憎油剂、调聚剂、药品和农用化学品的关键合成中间体。传统生产C2F5I的工艺存在工艺安全性差,生产成本高,原材料毒性大等不足。近年来国际上有人开始研究以五氟乙烷(C2F5H)和碘(12)为原料的高效、安全、绿色环保、工艺简单的“直接法”工艺,但有关研究的报道很少。本文重点针对C2F5I“直接法”合成工艺,开展以C2F5H为起始原料,对气相催化合成C2F5I的合成路线、反应机理、催化剂技术和工艺规律等进行了相关研究。
确定了理想气体C2F5I的热力学数据的最佳估算方法为Joback法,其次是键贡献法,得出C2F5I的热力学数据△Gf(?),298、ΔHf(?),298和Sf(?),298分别为-1060.31kJ·mol-1,-1005.79kJ-mol-1和388.34J·mol-1·K-1;对六种不同路线制备C2F5I的吉布斯自由能进行了计算,确立以C2F5H和12为原料制备C2F5I为最佳合成路线；热力学计算表明随着反应温度的升高,反应的标准自由焓变逐渐减小,平衡常数逐渐变大,在一定温度范围内升高温度在热力学上对C2F5I的生成有利；最后利用设计出的反应装置进行该催化反应,GC和GC-MS分析确认产物为C2F5I,表明该路线能合成出C2F5I。
在管式反应器中对C2F5H进行热裂解,用气相色谱-质谱仪、气相色谱仪对热解气体进行分析。结果发现：C2F5H在600-1000℃空管裂解时主要发生脱HF反应生成C2F4;C2F5H在催化剂Rb-K/AC条件下高温裂解主产物为C3F8和C4F10,而不是C2F4。根据均裂的化学键类型提出9个初级反应路径,通过密度泛函理论B3LY/6-31G*计算C2F5H各化学键离解能,发现H转移反应所需活化能最低,C-C键断裂反应次之,分别为211.73和380.10kJ/mol,表明C2F5H空管裂解时最易发生H转移反应脱去HF。生成活性中间体CF3CF:和CF2：的离解能分别为426.61和943.21kJ/mol,表明C2F5H在催化剂作用下最易生成CF3CF:卡宾。结合气体产物证实在催化剂裂解过程中生成了以CF3CF卡宾为主,CF2：卡宾为辅的活性中间体；采用H2作为捕捉剂,空管裂解C2F5H得到C2H2F4,当有催化剂存在时得到C2F6,表明CF3CF卡宾在催化剂表面吸附形成较强的结合。利用XPS对裂解后催化剂C1s进行分析发现结合能为282.2eV的C1s对应游离碳的特征峰,结合裂解主产物表明CF3CF:卡宾发生歧化反应,生成CF3CF2自由基和不同于石墨结构的单质C,CF3CF2自由基与I·自由基结合生成C2F5I。
第四章系统地研究了气相催化合成C2F5I的催化剂活性组分和载体对催化活性的影响。结果发现,碱金属盐作为催化剂活性组分具有较高的催化活性,尤其是负载量为20w%,质量比为2：1的KF和RbNO3的活性组分复配时催化剂催化活性最好。TG-DTA、 FTIR、XPS和XRD分析表明反应前催化剂活性组分RbNO3主要以Rb20存在,反应过程中的副产物HF使活性组分RbNO3以RbF和部分Rb2O形式存在。比表面积较大、灰分少、呈弱碱性的活性炭(AC)作为催化剂载体时,C2F5H的转化率较高；金属氟化物如多孔氟化铝和多孔氟化镁对O2和HF惰性,作为催化剂载体具有工业应用潜力。
对AC进行酸处理能够改变表面含氧官能团,从而加强金属前驱体与活性炭载体的锚固作用,改变催化剂的分散度和表面碱性。第四章采用HCl, HNO3或HF分别对AC进行处理,制得一系列AC负载的Rb-K催化剂,考察了它们在气相合成C2F5I反应中的催化性能。结果表明,HCl处理的AC负载的Rb-K/AC催化剂具有较高的分散度和适中的弱碱性,有利于气相催化合成C2F5I。各催化剂上活性组分分散度大小顺序为：Rb-K/AC-HNO3>Rb-K/AC-HF>Rb-K/AC-HCl>Rb-K/AC,该大小顺序与相应载体表面酸性和表面官能团变化趋势一致,但与催化剂表面碱性并无对应关系。酸处理对AC表面含氧官能团和表面碱性的变化能够很好地解释这一点。
在消除内外扩散的情况下,第五章利用气相催化合成C2F5I热力学和反应机理的研究结果对温度、空速、投料比等工艺条件进行优化研究,确定最佳工艺条件为：反应温度550℃～600℃,空速110130h-1,C2F5H:O2摩尔投料比为21.7：4。在优化条件下,催化剂Rb-K/AC使用寿命得到大幅度提高。
为了进一步提高催化剂的使用寿命,利用BET、SEM、XPS和TG-DTA等方法对反应前后催化剂进行了表征。结果表明,催化剂表面积炭导致催化剂孔道堵塞、活性中心覆盖是催化剂失活的主要原因。进一步研究表明该积碳为CF3CF：卡宾歧化生成的不同于活性炭载体石墨结构的单质碳和反应过程中产生的CF,CF2,CF3碎片；另外在反应体系中通入适量的O2能消除部分积碳,该积碳的氧化分解温度范围为150～350℃。
Pentafluoroethyl iodide (C2F5I) has higher reaction activity as well as the special physical chemistry function, which makes it for various applications, such as telogen for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides, a raw material of resins, functional materials and an intermediate for medicines and agrochemicals. However the traditional methods for the preparation of C2F5I have poor safety, high production cost and great toxicity of raw material. In recent years, a direct method process for the synthesis of C2F5I by the reaction of pentafluoroethane (C2F5H) and iodine (I2) has been developed successfully, which makes the green production become possible. But to the best of our knowledge, in the open literature, little information about it was reported. In this dissertation, a vapor-phase catalytic process for preparation of C2F5I from C2F5H was studied, especially the synthetic routes, reaction mechanism, catalytic technique and technological conditions.
Studies confirmed that Joback's group contribution was the best method to estimate the thermodynamic data of ideal gas C2F5I, and then the group bond contribution method. The thermodynamic data such as ΔGf,298(?),ΔAf,298(?) and Sf,298(?) is-1060.31kJ·mol-1,-1005.79kJ·mol-1and388.34J·mol-1·K-1respectively. According to the Gibbs free energy of the six different synthetic routes, the reaction between C2F5H with I2is an appropriate synthetic route. Thermodynamic calculation also showed that the equilibrium constants increase with the temperature increasing, and temperature rising was beneficial to the synthesis of C2F5I within a proper range. Over the experimental line system, the gas-phase catalytic reaction for the synthesis of C2F5I by the reaction of C2F5H and I2was conducted. The GC and GC-MS showed that C2F5I could be synthesis by this synthetic route.
The thermal decomposition properties of C2F5H were studied in a tubular reactor. The decomposed gas was characterized by gas chromatography-mass spectrometry (GC-MS), gas chromatography (GC). The results showed that the hydrogen fluoride eliminated to produce C2F4from C2F5H was the main reaction between600～1000℃, while in the pyrolysis of C2F5H over catalyst Rb-K/AC at550℃, the main products contained C4F10and C3F8,but no C2F4was detected. Nine primary reaction pathways were proposed based on the chemical bond types of the hemolytic cleavage. Using the DFT-(U)B3LYP/6-31G*method, the bond dissociation energies for all kinds of bonds were calculated. It was found that the activation energy of the H-transfer reaction and the C-C bond fission reaction, which are211.73kJ/mol and380.10kJ/mol, the activation energy of the production of CF3CF:and CF2:carbine were426.61kJ/mol and943.21kJ/mol. The result illustrated that the hydrogen fluoride elimination was the most feasible reaction in pyro lysis of C2F5H through empty reactor, but over catalyst Rb-K/AC, the formation of CF3CF: carbine was. H2as capture agent, was fed into reactor with C2F5H over catalysts or non-catalyst. It was found that in pyrolysis of C2F5H through empty reactor in the presence of H2, C2H2F4was obtained via the reaction of C2F4carbene with H2. But over catalyst, the formed CF3CF: carbene was adsorbed on the surface of AC. Moreover, the X-ray photoelectron spectroscopy (XPS) studies confirmed that the Cls signal around282.1eV could be assigned to C. It is proposed that in high temperature, catalyst Rb-K/AC promotes the dehydrofluorination of C2F5H to form CF3CF:carbene, and CF3CF: disproportionates to generate CF3CF2-radical and a new carbonaceous carbon which has different structure to graphite, at last CF3CF2-radical reacts with I-to form C2F5I.
The catalytic technique, including the active component and the carrier in the catalyst was investigated in detail. It was found that alkali metal salts as the active component showed a higher catalytic activity, especially the combined active substance having20wt%loading and2:1mass ratio of RbNO3and KF. The Rb-K/AC catalyst was characterized by TG-DTA, FTIR, XPS and XRD, and the results indicated that the species of the active component RbNO3before the reaction was Rb2O, and during the reaction process were Rb2O and RbF due to the reaction of Rb2O with the by-product HF. Activated carbon (AC), as the catalytic carrier, showed higher activity due to its high surface area, low ash content and slightly alkaline. And porous metal fluoride, such as porous aluminum fluoride and porous magnesium fluoride, as carriers showed medium activity and stable properties in the presence of O2and HF. So, Porous metal fluoride processed industrial potential application as carrier for this reaction.
Modification of AC with different acid solution might result in various surface oxygen groups, which can enhance the anchoring interaction between AC supports and metal precursors and change the dispersion and basicity of the catalyst. The influence of HCl, HNO3, and HF treatments on AC used as a support for Rb-K catalysts in the synthesis of C2F5I by reacting C2F5H with I2was studied. It was found that after the HCl treatment, the Rb-KF/AC-HCl catalyst with a high dispersion and moderately basicity was helpful for the enhancement of catalytic activity for C2F5I synthesis. The order of catalyst dispersion was as follows:Rb-K/AC-HNO3> Rb-K/AC-HF> Rb-K/AC-HCl>Rb-K/AC. The same sequence was also observed for the amount of the acid surface oxygen groups on AC, but not for the basicity of the catalyst. The key role of acid treatment on AC surface chemistry and the basic sites, which are closely related to catalyst dispersion and basicity, is examined to rationalize these findings.
Based on the thermodynamic analysis and catalytic mechanism, the reaction conditions such as reaction temperature, space velocity and the molar ratio were optimized after eliminating the influence of internal and external diffusion. The appropriate reaction temperature was550～600℃, space velocity was110～130h-1and the molar ratio of C2F5H and O2was21.7:4. Under the optimum conditions mentioned above, the catalyst life of Rb-K/AC was enhanced remarkably.
To improve further the catalyst life, the variations of catalysts after reaction and the deposited carbon over the catalysts were analyzed and characterized by XPS, TEM and TG-DTG etc. The results of the experiment indicated that the deactivation was caused mainly by the deposition of coke formation which led the pore blocking and active site coverage. Further investigation revealed that the coke species over Rb-K/AC catalyst include CF, CF2, CF3and carbonaceous carbon, and the mechanism of the coke formation is the disproportionation of C2HF5and CF3CF:carbene. The addition of O2to the reaction system could prevent the catalyst deactivation by burning off the coke during150～350℃.
确定了理想气体C2F5I的热力学数据的最佳估算方法为Joback法,其次是键贡献法,得出C2F5I的热力学数据△Gf(?),298、ΔHf(?),298和Sf(?),298分别为-1060.31kJ·mol-1,-1005.79kJ-mol-1和388.34J·mol-1·K-1;对六种不同路线制备C2F5I的吉布斯自由能进行了计算,确立以C2F5H和12为原料制备C2F5I为最佳合成路线；热力学计算表明随着反应温度的升高,反应的标准自由焓变逐渐减小,平衡常数逐渐变大,在一定温度范围内升高温度在热力学上对C2F5I的生成有利；最后利用设计出的反应装置进行该催化反应,GC和GC-MS分析确认产物为C2F5I,表明该路线能合成出C2F5I。
在管式反应器中对C2F5H进行热裂解,用气相色谱-质谱仪、气相色谱仪对热解气体进行分析。结果发现：C2F5H在600-1000℃空管裂解时主要发生脱HF反应生成C2F4;C2F5H在催化剂Rb-K/AC条件下高温裂解主产物为C3F8和C4F10,而不是C2F4。根据均裂的化学键类型提出9个初级反应路径,通过密度泛函理论B3LY/6-31G*计算C2F5H各化学键离解能,发现H转移反应所需活化能最低,C-C键断裂反应次之,分别为211.73和380.10kJ/mol,表明C2F5H空管裂解时最易发生H转移反应脱去HF。生成活性中间体CF3CF:和CF2：的离解能分别为426.61和943.21kJ/mol,表明C2F5H在催化剂作用下最易生成CF3CF:卡宾。结合气体产物证实在催化剂裂解过程中生成了以CF3CF卡宾为主,CF2：卡宾为辅的活性中间体；采用H2作为捕捉剂,空管裂解C2F5H得到C2H2F4,当有催化剂存在时得到C2F6,表明CF3CF卡宾在催化剂表面吸附形成较强的结合。利用XPS对裂解后催化剂C1s进行分析发现结合能为282.2eV的C1s对应游离碳的特征峰,结合裂解主产物表明CF3CF:卡宾发生歧化反应,生成CF3CF2自由基和不同于石墨结构的单质C,CF3CF2自由基与I·自由基结合生成C2F5I。
第四章系统地研究了气相催化合成C2F5I的催化剂活性组分和载体对催化活性的影响。结果发现,碱金属盐作为催化剂活性组分具有较高的催化活性,尤其是负载量为20w%,质量比为2：1的KF和RbNO3的活性组分复配时催化剂催化活性最好。TG-DTA、 FTIR、XPS和XRD分析表明反应前催化剂活性组分RbNO3主要以Rb20存在,反应过程中的副产物HF使活性组分RbNO3以RbF和部分Rb2O形式存在。比表面积较大、灰分少、呈弱碱性的活性炭(AC)作为催化剂载体时,C2F5H的转化率较高；金属氟化物如多孔氟化铝和多孔氟化镁对O2和HF惰性,作为催化剂载体具有工业应用潜力。
对AC进行酸处理能够改变表面含氧官能团,从而加强金属前驱体与活性炭载体的锚固作用,改变催化剂的分散度和表面碱性。第四章采用HCl, HNO3或HF分别对AC进行处理,制得一系列AC负载的Rb-K催化剂,考察了它们在气相合成C2F5I反应中的催化性能。结果表明,HCl处理的AC负载的Rb-K/AC催化剂具有较高的分散度和适中的弱碱性,有利于气相催化合成C2F5I。各催化剂上活性组分分散度大小顺序为：Rb-K/AC-HNO3>Rb-K/AC-HF>Rb-K/AC-HCl>Rb-K/AC,该大小顺序与相应载体表面酸性和表面官能团变化趋势一致,但与催化剂表面碱性并无对应关系。酸处理对AC表面含氧官能团和表面碱性的变化能够很好地解释这一点。
在消除内外扩散的情况下,第五章利用气相催化合成C2F5I热力学和反应机理的研究结果对温度、空速、投料比等工艺条件进行优化研究,确定最佳工艺条件为：反应温度550℃～600℃,空速110130h-1,C2F5H:O2摩尔投料比为21.7：4。在优化条件下,催化剂Rb-K/AC使用寿命得到大幅度提高。
为了进一步提高催化剂的使用寿命,利用BET、SEM、XPS和TG-DTA等方法对反应前后催化剂进行了表征。结果表明,催化剂表面积炭导致催化剂孔道堵塞、活性中心覆盖是催化剂失活的主要原因。进一步研究表明该积碳为CF3CF：卡宾歧化生成的不同于活性炭载体石墨结构的单质碳和反应过程中产生的CF,CF2,CF3碎片；另外在反应体系中通入适量的O2能消除部分积碳,该积碳的氧化分解温度范围为150～350℃。
Pentafluoroethyl iodide (C2F5I) has higher reaction activity as well as the special physical chemistry function, which makes it for various applications, such as telogen for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides, a raw material of resins, functional materials and an intermediate for medicines and agrochemicals. However the traditional methods for the preparation of C2F5I have poor safety, high production cost and great toxicity of raw material. In recent years, a direct method process for the synthesis of C2F5I by the reaction of pentafluoroethane (C2F5H) and iodine (I2) has been developed successfully, which makes the green production become possible. But to the best of our knowledge, in the open literature, little information about it was reported. In this dissertation, a vapor-phase catalytic process for preparation of C2F5I from C2F5H was studied, especially the synthetic routes, reaction mechanism, catalytic technique and technological conditions.
Studies confirmed that Joback's group contribution was the best method to estimate the thermodynamic data of ideal gas C2F5I, and then the group bond contribution method. The thermodynamic data such as ΔGf,298(?),ΔAf,298(?) and Sf,298(?) is-1060.31kJ·mol-1,-1005.79kJ·mol-1and388.34J·mol-1·K-1respectively. According to the Gibbs free energy of the six different synthetic routes, the reaction between C2F5H with I2is an appropriate synthetic route. Thermodynamic calculation also showed that the equilibrium constants increase with the temperature increasing, and temperature rising was beneficial to the synthesis of C2F5I within a proper range. Over the experimental line system, the gas-phase catalytic reaction for the synthesis of C2F5I by the reaction of C2F5H and I2was conducted. The GC and GC-MS showed that C2F5I could be synthesis by this synthetic route.
The thermal decomposition properties of C2F5H were studied in a tubular reactor. The decomposed gas was characterized by gas chromatography-mass spectrometry (GC-MS), gas chromatography (GC). The results showed that the hydrogen fluoride eliminated to produce C2F4from C2F5H was the main reaction between600～1000℃, while in the pyrolysis of C2F5H over catalyst Rb-K/AC at550℃, the main products contained C4F10and C3F8,but no C2F4was detected. Nine primary reaction pathways were proposed based on the chemical bond types of the hemolytic cleavage. Using the DFT-(U)B3LYP/6-31G*method, the bond dissociation energies for all kinds of bonds were calculated. It was found that the activation energy of the H-transfer reaction and the C-C bond fission reaction, which are211.73kJ/mol and380.10kJ/mol, the activation energy of the production of CF3CF:and CF2:carbine were426.61kJ/mol and943.21kJ/mol. The result illustrated that the hydrogen fluoride elimination was the most feasible reaction in pyro lysis of C2F5H through empty reactor, but over catalyst Rb-K/AC, the formation of CF3CF: carbine was. H2as capture agent, was fed into reactor with C2F5H over catalysts or non-catalyst. It was found that in pyrolysis of C2F5H through empty reactor in the presence of H2, C2H2F4was obtained via the reaction of C2F4carbene with H2. But over catalyst, the formed CF3CF: carbene was adsorbed on the surface of AC. Moreover, the X-ray photoelectron spectroscopy (XPS) studies confirmed that the Cls signal around282.1eV could be assigned to C. It is proposed that in high temperature, catalyst Rb-K/AC promotes the dehydrofluorination of C2F5H to form CF3CF:carbene, and CF3CF: disproportionates to generate CF3CF2-radical and a new carbonaceous carbon which has different structure to graphite, at last CF3CF2-radical reacts with I-to form C2F5I.
The catalytic technique, including the active component and the carrier in the catalyst was investigated in detail. It was found that alkali metal salts as the active component showed a higher catalytic activity, especially the combined active substance having20wt%loading and2:1mass ratio of RbNO3and KF. The Rb-K/AC catalyst was characterized by TG-DTA, FTIR, XPS and XRD, and the results indicated that the species of the active component RbNO3before the reaction was Rb2O, and during the reaction process were Rb2O and RbF due to the reaction of Rb2O with the by-product HF. Activated carbon (AC), as the catalytic carrier, showed higher activity due to its high surface area, low ash content and slightly alkaline. And porous metal fluoride, such as porous aluminum fluoride and porous magnesium fluoride, as carriers showed medium activity and stable properties in the presence of O2and HF. So, Porous metal fluoride processed industrial potential application as carrier for this reaction.
Modification of AC with different acid solution might result in various surface oxygen groups, which can enhance the anchoring interaction between AC supports and metal precursors and change the dispersion and basicity of the catalyst. The influence of HCl, HNO3, and HF treatments on AC used as a support for Rb-K catalysts in the synthesis of C2F5I by reacting C2F5H with I2was studied. It was found that after the HCl treatment, the Rb-KF/AC-HCl catalyst with a high dispersion and moderately basicity was helpful for the enhancement of catalytic activity for C2F5I synthesis. The order of catalyst dispersion was as follows:Rb-K/AC-HNO3> Rb-K/AC-HF> Rb-K/AC-HCl>Rb-K/AC. The same sequence was also observed for the amount of the acid surface oxygen groups on AC, but not for the basicity of the catalyst. The key role of acid treatment on AC surface chemistry and the basic sites, which are closely related to catalyst dispersion and basicity, is examined to rationalize these findings.
Based on the thermodynamic analysis and catalytic mechanism, the reaction conditions such as reaction temperature, space velocity and the molar ratio were optimized after eliminating the influence of internal and external diffusion. The appropriate reaction temperature was550～600℃, space velocity was110～130h-1and the molar ratio of C2F5H and O2was21.7:4. Under the optimum conditions mentioned above, the catalyst life of Rb-K/AC was enhanced remarkably.
To improve further the catalyst life, the variations of catalysts after reaction and the deposited carbon over the catalysts were analyzed and characterized by XPS, TEM and TG-DTG etc. The results of the experiment indicated that the deactivation was caused mainly by the deposition of coke formation which led the pore blocking and active site coverage. Further investigation revealed that the coke species over Rb-K/AC catalyst include CF, CF2, CF3and carbonaceous carbon, and the mechanism of the coke formation is the disproportionation of C2HF5and CF3CF:carbene. The addition of O2to the reaction system could prevent the catalyst deactivation by burning off the coke during150～350℃.
引文
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