共沸精馏提纯乙酰丙酮过程中水相后处理工艺的研究
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摘要
乙酰丙酮是一种重要的有机化工产品,有着广泛的工业应用。我国工业上乙酰丙酮的生产主要采用醋酸异丙烯酯异构化。由于异构化产物中醋酸,醋酐等副产物与乙酰丙酮的沸点相近,高纯度乙酰丙酮的分离提纯变得困难。上海华谊吴泾化工有限公司1000t/a乙酰丙酮的中试项目采用加水作为共沸剂共沸精馏方法生产高纯度乙酰丙酮,使乙酰丙酮的纯度达到99.5%以上。该工艺使用大量的水作为共沸剂,造成该工艺能耗很大,脱酸塔塔底产生大量含少量醋酸和乙酰丙酮的废水,直接排放不仅会造成AA的损失而且会对环境造成很大污染。针对这些问题,本文从两方面对废水处理工艺进行研究。第一,研究加碱中和醋酸、醋酐生成醋酸盐以去除废水中的醋酸、醋酐,对饱和的醋酸钠溶液进行结晶析出,并将盐水作为共沸剂循环使用的工艺。第二,对采用有机溶剂萃取方法回收废水中乙酰丙酮做了研究,并对回收萃取剂的精馏过程进行了模拟计算和实验研究,提出了适合该体系的萃取分离工艺,从而达到降低操作成本,节约能耗,回收有用物质的目的。
本文主要研究了以下内容：
(1)对醋酸钠对乙酰丙酮-水体系的液液平衡以及对乙酰丙酮-醋酸-水体系的汽液平衡的盐效应进行了研究,醋酸钠的加入降低了乙酰丙酮在水中的溶解度,增大了乙酰丙酮和水的不互溶区；醋酸钠对乙酰丙酮和醋酸都有盐析作用,增大了醋酸和乙酰丙酮在汽相中的含量,对乙酰丙酮的盐析效应大于对醋酸的盐析效应,分别用改进的Furter方程和Setschenow方程对汽液平衡数据和液液平衡数据进行了关联,关联系数都接近1。
(2)对加碱中和-降温结晶-盐水循环的工艺流程进行了实验研究,结晶温度对乙酰丙酮产品纯度的影响较大,结晶温度为5℃时,产品中醋酸含量小于0.1%,结晶温度为25℃时最终产品中醋酸的含量接近0.2%。循环废水PH值对乙酰丙酮产品质量的影响较小。经过连续140小时的连续实验,工艺操作的连续性和稳定性较好,产品的纯度也保持在很高的水平。
(3)对常压状态下水-乙酰丙酮-环己烷,水-乙酰丙酮-乙酸乙酯,水-乙酰丙酮-乙酸正丙酯三元体系在多个温度下的液液平衡数据进行了测定。得到各体系在288.15 K,298.15 K和313.15 K下的溶解度和节点数据。并用Bachman和Othmer-Tobias方程对实验数据进行了检验,关联效果较好。对不同萃取剂对乙酰丙酮的分配系数和选择性做了计算,比较了温度对萃取效果的影响,对于乙酸乙酯和乙酸正丙酯,低温情况下的分配系数更高,对于三种萃取剂都是低温下对乙酰丙酮的选择性更高。选用NRTL,UNIQUAC方程对实验数据进行了关联,得到各体系相应的二元交互作用参数,将实验结果和关键结果进行了比较,两个方程对三个体系的关联效果都很好。
(4)对环己烷-乙酰丙酮、环己烷-醋酸、乙酸乙酯-乙酰丙酮、水-乙酰丙酮二元体系在常压下,以及醋酸-乙酰丙酮在60.0 kPa下的恒压汽液平衡数据进行了测定。用Herington方程对热力学一致性进行检验,各数据均满足热力学一致性标准。对于含醋酸体系,由于醋酸存在强缔合作用,第二维里系数计算用化学理论和Hayden-O'Connell方程来表示其非理想性。实验发现环己烷-醋酸和水-乙酰丙酮体系存在最低共沸点,选用Wilson, NRTL,UNIQUAC方程对实验数据进行关联,三个方程对关联效果都很好,关联结果为后续的精馏分离提供设计依据。
(5)通过实验考察了乙酸乙酯和环己烷萃取醋酸和乙酰丙酮的效果,环己烷对醋酸的萃取效果极差,两种萃取剂对乙酰丙酮有很大的选择性,且在低温下选择性更大。由此设计了一条先萃取乙酰丙酮后处理含醋酸废水的工艺路线。根据液液平衡数据对各萃取剂萃取乙酰丙酮的级数进行了计算。用改进的转盘塔对乙酰丙酮进行了萃取研究,以环己烷为萃取剂,转盘塔转速对萃取结果的影响比相比要大,在200 r/min时萃取率不足10%,而在800 r/min时萃取率超过60%；以乙酸乙酯为萃取剂,萃取效果比环己烷要好,在大于600 r/min时,萃取相中己检测不到乙酰丙酮。
(6)在汽液平衡基础上,用ASPEN PLUS对萃取液的分离过程进行了模拟计算,确定了达到一定分离效果对塔工艺参数的要求,并对塔的灵敏度进行模拟分析。对精馏过程进行实验研究,建立了常压精馏分离环己烷与乙酰丙酮、醋酸以及乙酸乙酯与乙酰丙酮、醋酸的工艺流程,用于回收乙酰丙酮,实现萃取剂环己烷的循环利用,最终塔顶环己烷和乙酸乙酯的纯度分别达到99.2%和96.6%。收率超过99%。
Acetyl acetone is an important reagent in analytical and coordination chemistry, which is widely used in many industrial production units. Acetyl acetone is mainly produced by isomerization reaction of isopropenyl acetate. Acetic acid and acetic anhydride are main by-products in reaction product which are difficult to separate by using traditional distillation for their closed boiling points with acetyl acetone. Azeotropic distillation is used in the separation process with water as entrainer. In this process, large quantity of water was fed into the distillation column which increases energy consumption. Meanwhile masses of wastewater with small quantity of acetyl acetone and acetic acid were left at the bottom of the column. Direct emissions would cause significant pollution and loss of acetyl acetone. Focusing on solving those problems, two kinds of process of wastewater treatment were investigated. One process was neutralizing wastewater by adding alkaline and recycling saline water into the column after removing crystal salt. In another work, the process of recycling acetyl acetone from waste water by extraction was investigated systematically. Simulation and experiment of the distillation of extraction phase were both studied and a feasible process was developed.
The main contents of this thesis are as follows:
(1) Salt effects of sodium acetate on VLE of water+acetyl acetone+acetic acid and in LLE of water+acetyl acetone were investigated. Adding of sodium acetate increased immiscible area of water and acetyl acetone. The salt exhibited salting-out effects on acetyl acetone and acetic acid and the efficiency on acetyl acetone was a little greater than that of acetic acid.
(2) The process was neutralizing wastewater by adding alkaline and recycling saline water was studied with experiment. The influence of Ph value and crystallization temperature of saline water on the quality of product was studied. The experiment continued for 140 h, all the operation condition and product quality were stable, indicating the feasibility of this process.
(3) Liquid-liquid equilibrium data of the solubility curves and the tie-line compositions for ternary systems of water+acetyl acetone+ethyl acetate and water+acetyl acetone+propyl acetate, together with the tie-line compositions for ternary systems of water+acetyl acetone+ cyclohexane were determined. Distribution and selectivity coefficients were evaluated for the immiscibility region, which were found to be bigger at lower temperature. The reliability of the experimental tie-lines was confirmed by using Bachman and Othmer-Tobias correlation.
The experimental data were fitted using the NRTL and UNIQUAC equations, parameters of these two models were regressed.
(4) Isobaric vapor-liquid equilibrium (VLE) data for the binary systems of cyclohexane+ acetyl acetone, acetic acid+cyclohexane, water+acetyl acetone and acetyl acetate+acetyl acetone were determined at 101.3 kPa, and those for acetic acid+acetyl acetone system were determined at 60.0 kPa. A minimum boiling azeotrope was found in acetic acid+cyclohexane and water+acetyl acetone system. The non-ideality of the vapor phase of the acetic acid+ acetyl acetone and acetic acid+cyclohexane system were investigated by using Hayden-O'Connell equation. Thermodynamic consistency was tested for all of the VLE data by using Herington method. The experimental data were correlated satisfactorily by the Wilson, NRTL, UNIQUAC models. Correlation results were in good agreement with experimental data which provided the basic data for rectifying process design of the relevant components.
(5) The extraction of acetyl acetone and acetic acid from aqueous by cyclohexane and ethyl acetate were experimental studied. The extraction ability of ethyl acetate on acetyl acetone and acetic acid was better than cyclohexane and the distribution of acetyl acetone were both much bigger than that of acetic acid. The increasing of temperature significantly increased the distribution of acetic acid with cyclohexane as extractant. The temperature effect was not so obvious for ethyl acetate. The extraction process with modified rotating disc column was experimental studied. For cyclohexane, extraction efficiency was deeply affected by rotation speed rather than the phase ratio. The extraction percent of acetyl acetone was less than 10% at a rotation speed of 200 r/min but more than 60% at a rotation speed of 800 r/min. The extraction effect of ethyl acetate was far better than cyclohexane, there was no acetyl acetone left in residual extracted water at a rotation speed of 600 r/min.
(6) Based on the VLE data, simulation and experiment of the distillation of extraction phase were both studied; sensitivity analysis of distillation column was investigated. It was found that solvents were easy to be separated from extraction phase and recycling used in the extraction process. The optimal parameters of distillation column were obtained. The purity of cyclohexane and ethyl acetate were more than 99.2% and 96.6% respectively. The recovery percent of both solvents was more than 99%.
本文主要研究了以下内容：
(1)对醋酸钠对乙酰丙酮-水体系的液液平衡以及对乙酰丙酮-醋酸-水体系的汽液平衡的盐效应进行了研究,醋酸钠的加入降低了乙酰丙酮在水中的溶解度,增大了乙酰丙酮和水的不互溶区；醋酸钠对乙酰丙酮和醋酸都有盐析作用,增大了醋酸和乙酰丙酮在汽相中的含量,对乙酰丙酮的盐析效应大于对醋酸的盐析效应,分别用改进的Furter方程和Setschenow方程对汽液平衡数据和液液平衡数据进行了关联,关联系数都接近1。
(2)对加碱中和-降温结晶-盐水循环的工艺流程进行了实验研究,结晶温度对乙酰丙酮产品纯度的影响较大,结晶温度为5℃时,产品中醋酸含量小于0.1%,结晶温度为25℃时最终产品中醋酸的含量接近0.2%。循环废水PH值对乙酰丙酮产品质量的影响较小。经过连续140小时的连续实验,工艺操作的连续性和稳定性较好,产品的纯度也保持在很高的水平。
(3)对常压状态下水-乙酰丙酮-环己烷,水-乙酰丙酮-乙酸乙酯,水-乙酰丙酮-乙酸正丙酯三元体系在多个温度下的液液平衡数据进行了测定。得到各体系在288.15 K,298.15 K和313.15 K下的溶解度和节点数据。并用Bachman和Othmer-Tobias方程对实验数据进行了检验,关联效果较好。对不同萃取剂对乙酰丙酮的分配系数和选择性做了计算,比较了温度对萃取效果的影响,对于乙酸乙酯和乙酸正丙酯,低温情况下的分配系数更高,对于三种萃取剂都是低温下对乙酰丙酮的选择性更高。选用NRTL,UNIQUAC方程对实验数据进行了关联,得到各体系相应的二元交互作用参数,将实验结果和关键结果进行了比较,两个方程对三个体系的关联效果都很好。
(4)对环己烷-乙酰丙酮、环己烷-醋酸、乙酸乙酯-乙酰丙酮、水-乙酰丙酮二元体系在常压下,以及醋酸-乙酰丙酮在60.0 kPa下的恒压汽液平衡数据进行了测定。用Herington方程对热力学一致性进行检验,各数据均满足热力学一致性标准。对于含醋酸体系,由于醋酸存在强缔合作用,第二维里系数计算用化学理论和Hayden-O'Connell方程来表示其非理想性。实验发现环己烷-醋酸和水-乙酰丙酮体系存在最低共沸点,选用Wilson, NRTL,UNIQUAC方程对实验数据进行关联,三个方程对关联效果都很好,关联结果为后续的精馏分离提供设计依据。
(5)通过实验考察了乙酸乙酯和环己烷萃取醋酸和乙酰丙酮的效果,环己烷对醋酸的萃取效果极差,两种萃取剂对乙酰丙酮有很大的选择性,且在低温下选择性更大。由此设计了一条先萃取乙酰丙酮后处理含醋酸废水的工艺路线。根据液液平衡数据对各萃取剂萃取乙酰丙酮的级数进行了计算。用改进的转盘塔对乙酰丙酮进行了萃取研究,以环己烷为萃取剂,转盘塔转速对萃取结果的影响比相比要大,在200 r/min时萃取率不足10%,而在800 r/min时萃取率超过60%；以乙酸乙酯为萃取剂,萃取效果比环己烷要好,在大于600 r/min时,萃取相中己检测不到乙酰丙酮。
(6)在汽液平衡基础上,用ASPEN PLUS对萃取液的分离过程进行了模拟计算,确定了达到一定分离效果对塔工艺参数的要求,并对塔的灵敏度进行模拟分析。对精馏过程进行实验研究,建立了常压精馏分离环己烷与乙酰丙酮、醋酸以及乙酸乙酯与乙酰丙酮、醋酸的工艺流程,用于回收乙酰丙酮,实现萃取剂环己烷的循环利用,最终塔顶环己烷和乙酸乙酯的纯度分别达到99.2%和96.6%。收率超过99%。
Acetyl acetone is an important reagent in analytical and coordination chemistry, which is widely used in many industrial production units. Acetyl acetone is mainly produced by isomerization reaction of isopropenyl acetate. Acetic acid and acetic anhydride are main by-products in reaction product which are difficult to separate by using traditional distillation for their closed boiling points with acetyl acetone. Azeotropic distillation is used in the separation process with water as entrainer. In this process, large quantity of water was fed into the distillation column which increases energy consumption. Meanwhile masses of wastewater with small quantity of acetyl acetone and acetic acid were left at the bottom of the column. Direct emissions would cause significant pollution and loss of acetyl acetone. Focusing on solving those problems, two kinds of process of wastewater treatment were investigated. One process was neutralizing wastewater by adding alkaline and recycling saline water into the column after removing crystal salt. In another work, the process of recycling acetyl acetone from waste water by extraction was investigated systematically. Simulation and experiment of the distillation of extraction phase were both studied and a feasible process was developed.
The main contents of this thesis are as follows:
(1) Salt effects of sodium acetate on VLE of water+acetyl acetone+acetic acid and in LLE of water+acetyl acetone were investigated. Adding of sodium acetate increased immiscible area of water and acetyl acetone. The salt exhibited salting-out effects on acetyl acetone and acetic acid and the efficiency on acetyl acetone was a little greater than that of acetic acid.
(2) The process was neutralizing wastewater by adding alkaline and recycling saline water was studied with experiment. The influence of Ph value and crystallization temperature of saline water on the quality of product was studied. The experiment continued for 140 h, all the operation condition and product quality were stable, indicating the feasibility of this process.
(3) Liquid-liquid equilibrium data of the solubility curves and the tie-line compositions for ternary systems of water+acetyl acetone+ethyl acetate and water+acetyl acetone+propyl acetate, together with the tie-line compositions for ternary systems of water+acetyl acetone+ cyclohexane were determined. Distribution and selectivity coefficients were evaluated for the immiscibility region, which were found to be bigger at lower temperature. The reliability of the experimental tie-lines was confirmed by using Bachman and Othmer-Tobias correlation.
The experimental data were fitted using the NRTL and UNIQUAC equations, parameters of these two models were regressed.
(4) Isobaric vapor-liquid equilibrium (VLE) data for the binary systems of cyclohexane+ acetyl acetone, acetic acid+cyclohexane, water+acetyl acetone and acetyl acetate+acetyl acetone were determined at 101.3 kPa, and those for acetic acid+acetyl acetone system were determined at 60.0 kPa. A minimum boiling azeotrope was found in acetic acid+cyclohexane and water+acetyl acetone system. The non-ideality of the vapor phase of the acetic acid+ acetyl acetone and acetic acid+cyclohexane system were investigated by using Hayden-O'Connell equation. Thermodynamic consistency was tested for all of the VLE data by using Herington method. The experimental data were correlated satisfactorily by the Wilson, NRTL, UNIQUAC models. Correlation results were in good agreement with experimental data which provided the basic data for rectifying process design of the relevant components.
(5) The extraction of acetyl acetone and acetic acid from aqueous by cyclohexane and ethyl acetate were experimental studied. The extraction ability of ethyl acetate on acetyl acetone and acetic acid was better than cyclohexane and the distribution of acetyl acetone were both much bigger than that of acetic acid. The increasing of temperature significantly increased the distribution of acetic acid with cyclohexane as extractant. The temperature effect was not so obvious for ethyl acetate. The extraction process with modified rotating disc column was experimental studied. For cyclohexane, extraction efficiency was deeply affected by rotation speed rather than the phase ratio. The extraction percent of acetyl acetone was less than 10% at a rotation speed of 200 r/min but more than 60% at a rotation speed of 800 r/min. The extraction effect of ethyl acetate was far better than cyclohexane, there was no acetyl acetone left in residual extracted water at a rotation speed of 600 r/min.
(6) Based on the VLE data, simulation and experiment of the distillation of extraction phase were both studied; sensitivity analysis of distillation column was investigated. It was found that solvents were easy to be separated from extraction phase and recycling used in the extraction process. The optimal parameters of distillation column were obtained. The purity of cyclohexane and ethyl acetate were more than 99.2% and 96.6% respectively. The recovery percent of both solvents was more than 99%.
引文
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