毕业论文-离子液体催化合成苯甲酸甲酯的研究.doc

石家庄学院毕业论文毕 业 设 计（论 文）题 目：离子液体催化合成苯甲酸甲酯的研究院 系：化工学院专 业：制药工程班 级：姓 名：学 号：指导教师：2015年3月22日- 1 -离子液体催化合成苯甲酸甲酯的研究【摘要】苯甲酸甲酯，又名安息香酸甲酯，是一种重要的化工原料，可作为有机合成中间体、溶剂和香料，也可用于食品工业中。目前，工业上合成苯甲酸甲酯的主要方法是用浓硫酸作催化剂，该方法存在设备腐蚀严重、副反应多等缺点。本课题以苯甲酸和甲醇为原料，离子液体（吡啶和浓硫酸）为催化剂，对苯甲酸甲酯的合成进行研究。通过进行正交实验，探究催化剂的使用量，原料酸醇摩尔比，反应温度，反应时间对酯化反应产率的影响。实验结果表明，苯甲酸和甲醇的摩尔比为1：5，离子液体用量占总重10%，反应时间为4小时，温度为70时，苯甲酸甲酯的产率达到 76.8%。与传统催化剂浓硫酸相比，离子液体作为催化剂具有更好的催化效果。【关键词】离子液体；催化剂；合成；苯甲酸甲酯；产率Research on ionic liquids catalyzed synthesis of benzoic acid methyl ester【Abstract】Benzoic acid methyl ester was used as intermediates in organic synthesis, solvent and spices and used in the food industry. Benzoic acid methyl ester is an important chemical raw materials also known as methyl benzoic acid. The industrial use of concentrated sulfuric acid as catalyst for synthesis of methyl benzoate has many side reactions, serious corrosion of equipment etc. The research and study were carried out with benzoic acid and methanol as raw materials, ionic liquids (pyridine and sulfuric acid) as catalyst for the synthesis of methyl benzoate. Through orthogonal experiment to explore the influence about catalyst dosage, molar ratio, reaction temperature, reaction time on the esterification reaction yield. The experimental results show that the highest yield of methyl benzoate reached 76.8% when the molar ratio of benzoic acid and methanol was 1:5, the amount of ionic liquids for a total weight of 10%, reaction time was 4 hours, the temperature was 70 degrees centigrade. Compared with the traditional sulfuric acid catalyst, the catalytic effect of ionic liquid as catalyst has better.【Key Words】Ionic liquids; 催化剂catalyst; 合成synthesis; benzoic acid methyl benzene; productivity目 录1 引言12 实验部分22.1 仪器与试剂22.1.1 仪器22.1.2 试剂22.2 苯甲酸甲酯的合成22.2.1 实验原理22.2.2 实验步骤32.3 苯甲酸甲酯纯度检测分析32.3.1 苯甲酸甲酯气相检测条件32.3.2 苯甲酸甲酯红外检测33 结果与讨论43.1 催化剂用量对产物收率的影响43.2 酸醇摩尔比对产物收率的影响53.3 反应时间对产物收率的影响53.4 反应温度对产物收率的53.5 优化放大实验对产物纯度和收率的影响6结论6参考文献8附录9致谢10- 9 -石家庄学院毕业论文1 引言苯甲酸甲酯，又名安息香酸甲酯，是一种较为重要的酯类化合物，化学上可视为苯甲酸或苯甲酸酐或苯甲酰氯用甲醇醇解的产物。苯甲酸甲酯是一种不溶于水但能与甲醇、乙醚等混溶的透明液体,具有浓郁的冬青油和尤南迦油香气，可用于配制草莓、菠萝、樱桃等香味的食品保鲜剂、香水香精和人造精油等；苯甲酸甲酯还是一种重要的化工原料，工业上可用作有机合成中间体、作为合成纤维素酯、纤维素醚、树脂、橡胶等的溶剂13。目前，工业上合成苯甲酸甲酯的主要方法是用传统酸性催化剂浓硫酸作催化剂，但是此做法存在副反应多，产物分离复杂，设备腐蚀严重，废液污染环境等缺点，因而需要选择新的工艺路线进行苯甲酸甲酯的合成，相关报道也对多种催化剂进行了研究，但存在催化剂合成较为复杂，不利于工业化实施4。酸催化反应在化工行业中占有十分重要的地位。传统的酸性液体催化剂主要是硫酸和一些Lewis 酸，虽然它们的催化活性高，但是具有较强的腐蚀性，后处理也及其复杂，环境污染更为严重。所以，鉴于上述问题，为替代传统强腐蚀、强污染性的浓硫酸等无机酸，开发绿色的酸性催化剂很有必要，人们开始广泛开展对酸性离子液体催化剂的研究5。近年来，离子液体用于酸催化过程发展十分迅速，可用于烷基化、酰化、齐聚、酯化、缩合、醚化、酯交换等多种反应过程，在绿色催化和清洁合成等方面取得了很大的研究进展6。离子液体作为一种室温下熔融的盐、新型反应介质和绿色溶剂，具有液态范围宽、溶解范围广、蒸汽压为零、稳定性好、酸碱性可调、产品易分离和可循环利用等一系列独特性质，被认为是继水和超临界二氧化碳后的又一大类在现代有机合成中具有良好应用前景的反应介质和新型绿色溶剂，目前某些离子液体已经成功应用于对羟基苯甲酸乙酯的合成7。酸性离子液体作为一种新型的环境友好液体催化剂，拥有液体酸催化剂的高密度反应活性位，具有低挥发性，其结构和酸性具有可调变性8。与浓硫酸等传统催化剂相比，离子液体作为催化剂具有较高的催化活性和选择性，对环境的污染较小，产物易分离、还可循环利用，具有更好的催化效果，对于取代传统工业无机酸催化剂的潜力不可估量。本课题设计以苯甲酸和甲醇为原料，用离子液体(吡啶和浓硫酸)做催化剂制备苯甲酸甲酯，通过进行正交实验，探究催化剂用量，原料摩尔比，反应温度对酯化反应产率的影响，寻找最佳反应条件。2 实验部分2.1 仪器与试剂2.1.1 仪器YP402N电子天平，JJ-1精密定时电动搅拌器，DK-98-11电热恒温水浴锅，RE-52A旋转蒸发器，SHZ-D（）循环水式真空泵， DF-101S集热式恒温加热磁力搅拌器，101-2型电热鼓风干燥箱， GN-300A高纯氮发生器，GCD-300G高纯氢气发生器，9790气相色谱仪，Spectrum 100 FT-IR Spectrometer。2.1.2 试剂表2-1 部分实验试剂试剂名称生产厂家规格苯甲酸天津市恒兴化学试剂制造有限公司分析纯无水甲醇分析纯吡啶天津市美华泰克科技有限公司分析纯浓硫酸H2SO4分析纯饱和碳酸氢钠NaHCO3分析纯乙酸乙酯天津市永大化学试剂有限公司分析纯饱和氯化钠NaCl分析纯无水硫酸钠天津市永大化学试剂有限公司分析纯2.2 苯甲酸甲酯的合成2.2.1 实验原理催化剂2.2.2 实验步骤在装有温度计、搅拌器和回流冷凝管的四口烧瓶中，加入12.2g苯甲酸、过量的甲醇和一定量的催化剂，逐渐升温，在回流温度下维持温度反应一段时间。酯化反应结束后，进行旋转蒸发，蒸出过量的甲醇,分去催化剂。酯化反应完毕后, 待反应液的温度降至室温, 油箱以饱和NaHCO3水溶液调溶液的pH至中性。下层残留液冷却后倒入分液漏斗中，每次用10mL乙酸乙酯洗涤2 次、然后用10mL饱和氯化钠水溶液洗涤2次。分液后下层水相再用10mL乙酸乙酯萃取2次，合并有机相，得到粗苯甲酸甲酯。将粗品苯甲酸甲酯移入盛有无水硫酸钠的干燥锥形瓶中，干燥过夜。滤液进行蒸馏收集120150的馏分，即得产品苯甲酸甲酯。2.3苯甲酸甲酯的纯度检测分析2.3.1 苯甲酸甲酯气相检测条件色谱柱：毛细管柱，长30m，内经0.53mm；载气为氮气，纯度99.999%，流量为1.0 ml/min；固定相：二甲基聚硅氧醚；进样口温度：220 ，检测器温度：280 ；采用直接升温，温度10，分流比为1：40；进样量：0.2ul12, 13。检测表明，最终产品苯甲酸甲酯含量稳定在99.5%左右，产品纯度达到要求。2.3.2 苯甲酸甲酯红外检测对产物进行红外光谱分析，在1725cm-1和1279cm-1处分别有酯基的C=O和C-O的特征吸收峰，在1601 cm-1和1452 cm-1出现苯环骨架的特征吸收峰，因此，说明产物为苯甲酸甲酯。3 结果与讨论3.1 催化剂用量对产物收率的影响酯化反应条件：酸醇摩尔比1：5，反应温度70，反应时间4小时，改变催化剂用量，所得产物苯甲酸甲酯的产率变化如表3-1所示。表3-1 催化剂用量对产物收率的影响催化剂用量（g）2%6%10%14%产物收率（%）55.375.673.873.6由表3-1可知，当催化剂用量占所有原料的6%时，产率达到75.6%，降低催化剂用量到2%时，反应不完全，产率降至55.3%，但当催化剂用量升至10%和14%时，产率稳定在73.7%左右。随着催化剂使用量的增加，产品收率也随之增加，但增加到一定值后，随着催化剂使用量的增加，产物收率无明显变化。所以，结果表明产物收率最高时即在酸醇摩尔比1：5，反应温度70，反应时间4小时的条件下，催化剂最佳用量为6%。3.2 酸醇摩尔比对产物收率的影响酯化反应条件：催化剂用量为6%，反应温度70，反应时间4小时，改变酸醇摩尔比，所得产物苯甲酸甲酯的产率变化如表3-2所示。表3-2 酸醇摩尔比对产物收率的影响醇酸摩尔比3456产物收率（%）43.758.376.874.9由表3-2可知，酸醇摩尔比达到5之前，甲醇用量的增大有利于反应向生成酯的方向移动，产物的收率随摩尔比的增大而增加，当酸醇摩尔比达到5时，产物的收率增至76.8%，当摩尔比增至6时，产物收率降至74.9%，这是因为随着甲醇用量的增加，反应体系的回流量也在增加，使得原料酸醇的浓度均会降低。随着醇酸摩尔比的增加，产品收率首先增加，但增加到一定值后，随着醇酸摩尔比的增加，产物收率无明显变化甚至降低。所以，结果表明产物收率最高时即在催化剂用量为6%，反应温度70，反应时间4小时的条件下，最佳酸醇摩尔比为1：5。3.3 反应时间对产物收率的影响酯化反应条件：酸醇摩尔比1：5, 催化剂用量为6%，反应温度70，改变反应时间，所得产物苯甲酸甲酯的产率变化如表3-3所示。表3-3 反应时间对产物收率的影响反应时间（h）33.544.5产物收率（%）55.668.775.974.2由表3-3可知，在4小时之前，产率随时间的增加而增加，反应时间增至4小时，产率达到75.9 %，当反应时间增至4.5小时后，产率降至74.2 %。随着反应时间的增加，产品收率首先增加，但增加到一定值后，随着反应时间的增加，产物收率无明显变化甚至下降，而且增加副产物和能耗。所以，结果表明产物收率最高时即在酸醇摩尔比1：5， 催化剂用量为6%，反应温度70的条件下，最佳反应时间为4小时。3.4 反应温度对产物收率的影响酯化反应条件：酸醇摩尔比1：5，催化剂用量为6%，反应时间4小时,改变反应温度，所得产物苯甲酸甲酯的产率变化如表3-4所示。表3-4 反应温度对产物收率的影响反应温度（）60657075产物收率（%）53.668.774.874.2由表3-4可知，在反应温度达到70之前，随着反应温度的升高，产物的收率也随之增加，达到70时，产率达到74.8%，当反应温度升到75时，产率降至74.2%，随着反应温度的增加，产品收率首先增加，但增加到一定值后，随着反应温度的增加，产物收率无明显变化甚至下降，而且增加副产物和能耗。所以，结果表明产物收率最高时即在酸醇摩尔比1：5，催化剂用量为6%，反应时间4小时的条件下,最佳反应温度为70小时。3.5 优化放大实验对纯度和收率的影响根据以上各组实验，选择酸醇摩尔比1：5，催化剂用量为6%，反应时间4小时,反应温度70条件下的实验组作为优化组与其放大四倍后的优化放大组对比。优化组各试剂用量为：苯甲酸12.2g，无水甲醇21.1ml，离子液体成品1.8g，采用反应温度70，反应时间4小时。优化放大组各试剂用量为：苯甲酸48.8g，无水甲醇84.4ml，离子液体成品7.2g，采用反应温度70，反应时间4小时,实验后所得苯甲酸甲酯粗品质量、产品纯度和收率变化如表3-5所示。表3-5优化放大实验对纯度和收率的影响实验组 m（苯甲酸） V（无水甲醇） m（离子液体） 纯度 收率优化组 12.2g 21.1ml 1.8g 99.48% 75.60%优化放大组 48.8g 84.4ml 7.2g 99.51% 78.33%由表3-5可见，根据以前做过的各实验组所得苯甲酸甲酯粗品质量、碘液用量、产品纯度和收率数据的综合分析，酸醇摩尔比1：5，催化剂用量为6%，反应温度70，反应时间4小时条件下实验组的各项数据最佳。将该组放大四倍后，收率较高。结果表明，优化组各项数据效果比较好，优化放大后数据波动不大。4 结论以苯甲酸和甲醇为原料，离子液体（吡啶和浓硫酸）为催化剂，合成苯甲酸甲酯的最佳反应条件为：酸醇摩尔比1：5，反应温度70，反应时间4小时，产物收率可达75%以上。与传统催化剂浓硫酸相比，吡啶与浓硫酸的离子液体催化合成苯甲酸甲酯的有效催化剂之一，作为催化剂具有腐蚀性小、反应条件温和、污染小，且易于分离回收，能多次重复使用等特点，有更好的催化效果。参考文献1 殷树梅复合催化剂催化合成苯甲酸甲酯J. 精细石油化工进展，2009，10(7)： 5-6.2 李兑，黄先胜，李平，等.催化合成苯甲酸甲酯的研究J. 化工，2013，39(3)：25-26.3 战宇，宁正祥. 苯甲酸甲酯的合成及抑菌效果研究J. 华南农业大学学报，2012，23(1)：82-84.4 尚海燕，王宏伟. 氯化铝催化合成苯甲酸甲酯J. 内蒙古石油化工，2002，27：7-8.5 王敬娴，吴芹，黎汉生，等. 酸性离子液体及其在催化反应中的应用研究进展J. 化工进展，2008，27(10)：1574-1592.6 谢辉，陈卓，王永芹，等. 室温离子液体催化对羟基苯甲酸乙酯的合成研究J. 安徽农业科学，2011，39( 15)：91299130.7 刘晓庚. 室温离子液体及其在香料工业中的应用D. 南京：南京财经大学，2004.8 顾彦龙，彭家建，乔琨，等. 室温离子液体及其在催化和有机合成中的应用J.化学进展，2003，15(3)：222-241.9 阮华屹，张旺喜，徐保明，等. 3-氰基苯甲酸甲酯的绿色合成J. 石油化工，2013，42(1)：59-63.10 资爱平，唐刚，晏彩先，等. 对溴甲基苯甲酸甲酯的合成研究J. 广州化工，2012，40(4)：21-23.11 叶天旭，刘京燕，张斌，等. 磷钨酸拟薄水铝石负载催化剂合成对羟基苯甲酸乙酯J. 应用化学，2009，26( 9)：114-116.12 王凤霞. 气相色谱在食品分析中的应用D. 山东：烟台大学，2013.13 周晶，戴发荣，李拥军. 食品中对羟基苯甲酸甲酯和对羟基苯甲酸丙酯的气相色谱同时测定法J. 职业与健康，2005，21(1)：41-42.14 付林林. 吡啶类离子液体的合成及其对纤维素溶解性能的研究D. 河北：河北科技大学，2012.15 何绍群，赵锁奇，孙学文，等. 吡啶离子液体的热分析研究J. 天然气化工，2006，31(1)：25-28.附录吡啶浓硫酸离子液体的制备离子液体是适应时代发展要求，继水和超临界二氧化碳应运而生的又一高效绿色催化剂，主要由有机阳离子和无机离子构成，在室温或室温附近呈液态的盐类化合物,具有不可挥发等较高的稳定性，已被成功应用于有机合成等各项领域14。将吡啶与浓硫酸按1:1的比例混合均匀, 放入烧瓶中, 常温下在磁力搅拌器上搅拌加热, 熔融大约3小时，直至得到无色清亮液体即可, 停止加热, 然后在真空干燥箱里70 干燥24 h, 取出后冷却, 放在干燥器中备用。合成的吡啶浓硫酸离子液体在室温下为液体，易溶于强极性溶剂，如水、乙醇等；不溶于弱极性溶剂，如乙醚、甲苯等15。气相检测注意事项本次气相色谱检测的进样方法采用的是手动进样，使用微量注射器进行手动进样时，操作的数量程度取决于精密度，各项操作应尽量一致。要注意以下几点：选用恰当的注射器，常用的是10ul微量注射器，进样量不能小于1uL；注射速度必须要快，注射速度过慢会延长样品的气化过程，导致样品进入色谱柱的初始谱带变宽；避免样品之间相互干扰，取样之前要用样品溶剂洗针不少于3次，再用样品溶液洗针不少于3次，这样基本上能够消除样品间的相互干扰；减少注射歧视，不管注射速度多快，不同组分沸点不同，汽化速度也会不同，从而造成定量分析的误差，所以取样前先将注射针插入汽化室预热一定时间，或者取样前先在注射器中抽取一定量的溶剂。正确的注射方法应当是：取样后，一只手拿注射器，并把食指放在针芯的束端(以防汽化室的高气压把针芯吹出)，同时另一只手要保护针尖(防止插入时受到隔垫阻挡弯曲)，小心地将注射针头插入隔垫，此时要以最快的速度将注射器插到底，与此同时迅速地将样品注射入汽化室(注意不要弯曲针芯)，最后快速拔除掉注射器。注射样品时所需的时间以及注射器在汽化室中停留的时间越短越好，而且每次注射的过程越重现越好。分析完毕，待组分流出后，先关闭氢气和空气，再进行降温操作。将进样口、柱温箱、检测器以及顶空进样器的温度均设为40，待各组件的温度不高于40以后，依次关闭载气，工作站和气相色谱仪。如果要取下色谱柱，则取下后柱两端应用盲堵堵上并放在盒内，妥善保存。收率的计算公式收率=M实际/M理论*100% M理论=M苯甲酸/122*136致谢随着论文完成，四年的大学生活也即将结束，感慨万千！从选题的开始到论文的顺利完成，老师、同学、朋友们不管是在学习上还是生活中都给了我数不尽的帮助，在这里，请接受我发自内心的谢意！感谢我的导师贾鹏飞和王娟老师。从课题选择、开题，到进行实验、论文写作、整理的整个过程，贾老师和王老师都倾注了大量的心血，给了我很多受用终生的指导。在这里我要再次向我的老师们表示深深的敬意和感谢！ 感谢我的辅导员韩老师，他为我们的日常课程和学习尽心尽力，为我们组织考研、论文写作、工作，再辛苦也无怨言。感谢各位校领导和化工学院的老师们，是你们让学校充满治学之风，使我们能够更好的学习知识和完成学业！也要感谢2011级制药工程专业的同学们，他们在生活和学习上给了我很多帮助和关怀。更要感谢我的父亲、母亲，感谢他们对我的养育、教诲和支持。最后，请允许我再次说一声，谢谢大家！您好，为你提供优秀的毕业论文参考资料，请您删除以下内容，O(_)O谢谢！A large group of tea merchants on camels and horses from Northwest Chinas Shaanxi province pass through a stop on the ancient Silk Road, Gansus Zhangye city during their journey to Kazakhstan, May 5, 2015. The caravan, consisting of more than 100 camels, three horse-drawn carriages and four support vehicles, started the trip from Jingyang county in Shaanxi on Sept 19, 2014. It will pass through Gansu province and Xinjiang Uygur autonomous region, and finally arrive in Almaty, formerly known as Alma-Ata, the largest city in Kazakhstan, and Dungan in Zhambyl province. The trip will cover about 15,000 kilometers and take the caravan more than one year to complete. The caravan is expected to return to Jingyang in March 2016. Then they will come back, carrying specialty products from Kazakhstan A small art troupe founded six decades ago has grown into a household name in the Inner Mongolia autonomous region. In the 1950s, Ulan Muqir Art Troupe was created by nine young musicians, who toured remote villages on horses and performed traditional Mongolian music and dances for nomadic families. The 54-year-old was born in Tongliao, in eastern Inner Mongolia and joined the troupe in 1975.He says there are 74 branch troupes across Inner Mongolia and actors give around 100 shows every year to local nomadic people. I can still recall the days when I toured with the troupe in the early 80s. We sat on the back of pickup trucks for hours. The sky was blue, and we couldnt help but sing the folk songs, Nasun says. The vastness of Inner Mongolia and the lack of entertainment options for people living there, made their lives lonely. The nomadic people were very excited about our visits, Nasun recalls. We didnt have a formal stage. The audience just sat on the grass. Usually, the performances became a big party with local people joining in. For him, the rewarding part about touring isnt just about sharing art with nomadic families but also about gaining inspiration for the music and dance. Ulan Muqir literally translates as red burgeon, and todays performers of the troupe still tour the regions villages and entertain nomadic families, but their fame has spread around the world. On May 16 and 17, nearly 100 singers and dancers from the troupe performed at Beijings Poly Theater. Their show, titled Ulan Muqir on the Grassland, depicted the history and development of the art troupe. Being from the region allowed me to embrace the culture of Inner Mongolia and being a member of the troupe showed me where I belonged, Nasun, the art troupes president, who is also a renowned tenor, tells China Daily. During a tour in 1985, he went to a village and met an elderly local man, who told him a story about his friendship with a solider from Shenyang, capital of Northeast Chinas Liaoning province, decades ago. The solider gave the old man a handmade saddle when they bid farewell. The story inspired Nasun to write Carved Saddle, a song that later became one of his most popular numbers. Now, every year, Nasun recruits young singers and dancers for the troupe. The troupe has also designed a new repertoire, which is mostly based on the daily lives of Mongolian people, especially the lives of nomadic families, and has combined contemporary musical elements with folk songs of the region. Haimu, a 25-year-old khoomei (a local variant of overtone singing) singer, joined the troupe three years ago. Along with a six-member band, he performs fast songs and soft ones that he writesall while playing the horse-head fiddle.Although I learned the piano since childhood and grew up listening to various kinds of music, to me, the folk music of Inner Mongolia is the root, he says. Performing in remote villages is pleasant. I feel at home on the boundless grasslands, and the warm people there make me feel fulfilled. The first round of spring auction season in Beijing ended last week, but it failed to create much spring in the art market. Although two pieces of Chinese painting fetched more than 100 million yuan, the decline in trading volume and sale rate showed a downturn this year. In the “Grand View: Chinese Painting Highlight” session at China Guardian 2015 spring auctions, Pan Tianshous representative work Eagle, Rock and Flora hit a record auction price of 279 million yuan, while Li Kerans masterwork Jinggang Mountain fetched 126.5 million yuan, an unexpected high in recent years. However, the trading volume fells to 1.87 billion yuan from 2.22 billion yuan in the same period the year before. The Huangchen 2015 Spring Auctions, which recorded 42.5 million yuan in total sales, experienced the same. The section number went down to 5 from 12 compared to last year. According to expert Shao Jianwu, the art market did not attract much excitement this year due to the booming stock market and the persistent problems of forgery and fake deals. The two pieces of Chinese painting notched up high price this spring due to their own value not due to a revival in the market. The successful transaction of two works with a hammer price of more than 100 million yuan once again confirms that valuable and rare works of high quality always earn the long-lasting high price. Chinese painting and calligraphy is still the pillar of the market. However, the overall sales rate has dropped slightly, which reflects the demand for the ordinary auction goods has weakened,” said the president of China Guardians Hu Yanyan. Besides, the entry of new buyers also makes certain changes to the direction of purchasing. In a word, the overall market trend is very unpredictable. Although China Guardian 2015 Spring Auctions has achieved remarkable results, it does not mean that the market has walked out of the predicament. We still have to wait for the big economic boom to invigorate the art market.” Even so, the hot pursuit of some special items appeared this spring. A special session of China Guardian Spring Auctions titled “Fine GiltBronze Buddhist Images” achieved a great deal with total sales volume of 41.89 million yuan and 92 percent sale rate. The 5th Shamar Rinpoche Statue from 16-17th century of Tibet was sold for 5.06 million yuan. The Beijing Chengxuan Auctions featured almost 2,800 items of coins and stamps in three sessions with good sale rate. The Huachen Auctions also set a special session of photographs under the condition of large-scale decline of auction sessions. There was a palpable dull thud of disappointment that accompanied the return of the imperial entourage of Zhen Huan to her homeland. It followed a couple years of hushed excitement as Chinese fans were fed tidbits about their proud concubine who was supposed to conquer the high ground of the North American market. Zhen Huan is, of course, the title character of The Legend of Zhen Huan, a 2011 television series that swept China off its feet and later took other Asian countries by storm. Two years ago, it was reported that HBO, a premium cable service headquartered in the United States, was going to air it in North America after some modification. Now, a condensed version that provides English subtitles but no dubbing has finally been made available on Netflix for online streaming. This version, highly anticipated as a milestone in Chinas cultural foray overseas, has been widely panned by its home audience. Retitled Empresses in the Palace, the American version has been shortened from its original 76 episodes at 45 minutes each, to six 90-minute episodes. The quick pacing threw off many native viewers, who are accustomed to a more leisurely daytime-soap-style narrative rhythm. (Chinese TV stations would run two or three episodes every day.) I did not finish the full-length version and found the truncated one not difficult to follow. Whats lost, I believe, are the interesting setups and pauses that illuminate the Chinese art of storytelling. Much of the plot is still there. It is the flavor that was sacrificed. The American edition uses the framework of the Empress Dowager in her senior years reminiscing at the beginning and the end of each episode, hinting at whats to come and recapping the key points. This device, not used in the original, is culturally understandable but artistically mediocre. What puzzles me is the two new songs for the opening and end credits. They were written in English, but sung by Chinese with an uncomfortable accent. They were obviously designed to appeal to an English-speaking base, but do not jibe with the Chinese dialogue. Speaking of the dialogue, the English translation, picked apart by some Chinese, is too literal for my taste. I can imagine a typical American hit by a flurry of royal ranks, addresses and greetings, even multiple names and titles for the same person. The first half hour must be a swamp to wade through, very much like my experience of getting through a Tolstoy tome with its endless inflections of names transliterated into lengthy Chinese. I see the choice of verbatim translation as an effort for conveying exotica. It is fairly competent, with no error tha