CN108530249A - 苯和异丙苯生产正丙苯的方法 - Google Patents

苯和异丙苯生产正丙苯的方法 Download PDF

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CN108530249A
CN108530249A CN201710122128.9A CN201710122128A CN108530249A CN 108530249 A CN108530249 A CN 108530249A CN 201710122128 A CN201710122128 A CN 201710122128A CN 108530249 A CN108530249 A CN 108530249A
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benzene
isopropylbenzene
proplbenzene
production
molecular sieve
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王高伟
高焕新
魏伦
魏一伦
胥明
尤陈佳
顾瑞芳
方华
季树芳
姚辉
刘远林
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China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
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Sinopec Shanghai Research Institute of Petrochemical Technology
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Abstract

本发明涉及一种苯和异丙苯生产正丙苯的方法，包括苯和异丙苯在有效反应条件下与催化剂接触得到正丙苯的步骤；其特征在于，所述有效反应条件包括温度至少大于200℃。所述方法可用于正丙苯的工业生产中。

Description

苯和异丙苯生产正丙苯的方法
技术领域
本发明涉及一种苯和异丙苯生产正丙苯的方法。
背景技术
丙基苯是重要的化工产品，可直接作为溶剂，也是合成其它重要化工原料的中间体。丙基苯主要有两种同分异构体，异丙苯和正丙苯。异丙苯是生产苯酚、丙酮和α-甲基苯乙烯的重要中间体，也可用作提高燃料油辛烷值的添加剂、合成香料和聚合引发剂的原料等。正丙苯可用于纺织染料、印刷、醋酸纤维溶剂。目前最新的用途是用做合成山梨醇类聚丙烯成核剂。山梨醇类成核剂是由醇醛缩合反应生成，通过山梨醇分子上引入丙基或烯丙基，苯甲醛母体结构引入丙基、乙基或丙氧基基团合成。山梨醇类成核剂与聚丙烯有很好的相容性，且能明显改善制品的透明性、刚性、表面光泽度及其他热力学性能，是销量最大、使用最广泛的有机成核剂。2009年美国Milliken公司研发出了NX8000产品，结构式为
该成核剂是两分子正丙基苯甲醛与正丙基山梨醇的缩合产物，具有成核效率高、透明度大、生物适应性好和气味小等优点。NX8000的推广和使用将会极大促进正丙苯的工业产能。
郑行行等(石油化工2012年第9期1056页)报导了以苯和丙酸为起始原料，经酰氯化、Freidel-Crafts酰基化和基斯内尔-沃尔夫-黄鸣龙还原反应合成了正丙苯。该反应步骤繁琐不适宜工业生产。
目前以丙烯、卤代丙烷或异丙醇为烷基化试剂与苯反应时，烷基化试剂在酸催化作用下形成的碳正离子易发生重排，得到的产物通常以异丙苯为主，而正丙苯是极微量的，只有300mg/Kg左右。其主要原因是：从反应机理的角度看仲碳正离子的稳定性远高于伯碳正离子，生成异丙苯的活化能更低，因此在动力学上生成异丙苯是更有利的。
发明内容
本发明旨在提供一种苯和异丙苯生产正丙苯的方法。该方法具有正丙苯选择性高的特点。
为实现上述发明目的，本发明采取的技术方案如下：一种苯和异丙苯生产正丙苯的方法，包括苯和异丙苯在有效反应条件下与催化剂接触得到正丙苯的步骤；其特征在于，所述有效反应条件包括温度至少大于200℃。
上述技术方案中，所述温度优选为220～500℃，更优选为250～400℃，最优选为270～350℃。
上述技术方案中，所述催化剂以重量百分比计，包括以下组份：a)40～90％的沸石分子筛；b)10～60％的粘结剂；所述沸石分子筛选自具有MFI、MWW、BEA、MOR和FAU拓扑结构分子筛中的至少一种。
上述技术方案中，优选地，所述沸石分子筛具有MFI拓扑结构；更优选地，所述沸石分子筛为ZSM-5分子筛。
上述技术方案中，所述沸石分子筛SiO2/Al2O3摩尔比为10～50。
上述技术方案中，所述粘结剂选自氧化铝、氧化钛、氧化锌和氧化锆中的至少一种。
上述技术方案中，所述有效反应条件还包括：压力0.5～5.0MPa，优选1.0～4.0MPa；苯和异丙苯摩尔比0.1～10，优选1～8；异丙苯重时空速为0.1～10小时-1，优选0.2～5小时-1。
本发明方法工艺流程简单，生产成本低，采用至少大于200℃的反应温度，使得苯和异丙苯在较高的反应温度下进行异构化反应，发生丙基的重排获得了正丙苯，正丙苯收率可高达40％，取得了较好的技术效果。
下面通过实施例对本发明作进一步阐述。
具体实施方式
【实施例1】
合成具有MFI拓扑结构的ZSM-5分子筛。
首先制备胶态晶种，将710.3g H2O，13.8g NaOH与117.0g TPAOH(20％溶液)溶液充分溶解混合至均匀，再在搅拌下将158.9g硅酸逐步加入上述溶液中，在室温下充分振荡1h后，在100℃下陈化16h；将867.8g H2O，8.8g NaOH与10.3g铝酸钠充分混合相溶，将113.1g硅酸在充分搅拌下逐步加入上述混合溶液中并猛烈振荡1h，将制备的胶态晶种50g加入至上述混合溶液中振荡1h，然后将物料转移至不锈钢反应釜中。在180℃下晶化40h后过滤、洗涤、干燥结晶产物。经XRD粉末衍射分析所得的结晶产品为ZSM-5分子筛，其硅铝比＝12～13.5。
取50g干燥后的粉末样品，用1M的硝酸铵交换4次，过滤、干燥。之后与20g氧化铝充分混合，并加入5wt％硝酸捏合、挤条成型为 的条状物，120℃干燥12小时，500℃焙烧6小时，制备成需要的催化剂。
【实施例2】
合成具有FAU拓扑结构的Y型分子筛。
首先制备胶态导向剂，将20.0g H2O，4.0g NaOH与2.1g铝酸钠(20％溶液)溶液充分溶解混合至均匀，再在搅拌下将22.7g硅酸逐步加入上述溶液中，在室温下充分振荡1h后，在室温下陈化过夜；将261.9g H2O，0.28g NaOH与20.6g铝酸钠充分混合相溶，将284.8g硅酸在充分搅拌下逐步分批加入至上述混合溶液中并猛烈振荡1h，将制备的导向剂50g加入至上述混合溶液中振荡1h。然后将物料转移至不锈钢反应釜中。在100℃下晶化10h后过滤、洗涤、干燥结晶产物。经XRD粉末衍射分析所得的结晶产品为Y型分子筛。
取50g干燥后的粉末样品，用1M的硝酸铵交换4次，过滤、干燥。之后与20g氧化铝充分混合，并加入5wt％硝酸捏合、挤条成型为 的条状物，120℃干燥12小时，500℃焙烧6小时，制备成需要的催化剂。
【实施例3】
合成具有BEA拓扑结构的Beta分子筛。
将600g 40wt.％硅溶胶，38.9g铝酸钠(氧化铝含量42wt.％)，70.6g 25wt.％四乙基氢氧化铵(TEAOH)，5.0g二乙胺(DEA)，168.0g四乙基溴化铵(TEABr)，16.0g氢氧化钠，136.0g 25wt.％的氢氧化铵，925.1g水混合，常温下搅拌均匀。然后转入不锈钢高压釜中，晶化温度155℃，反应50小时。反应结束后，过滤、洗涤、干燥结晶产物。经XRD粉末衍射分析所得的结晶产品为Beta沸石。
取50g干燥后的粉末样品，用1M的硝酸铵交换4次，过滤、干燥。之后，与20g氧化铝充分混合，并加入5wt％硝酸捏合、挤条成型为 的条状物，120℃干燥12小时，500℃焙烧6小时，制备成需要的催化剂。
【实施例4】
合成具有MOR拓扑结构的丝光沸石型分子筛。
将19gNaOH在搅拌下溶入40g H2O中，将14.3铝酸钠与上述NaOH溶液混合，搅拌至全溶。将上述混合溶液在加入497gH2O稀释，将245.5g 40wt.％硅溶胶加入上述溶液中搅拌30min后将溶液后转入不锈钢高压釜中，晶化温度170℃，反应24小时。反应结束后，过滤、洗涤、干燥结晶产物。经XRD粉末衍射分析所得的结晶产品为丝光沸石。
取50g干燥后的粉末样品，用1M的硝酸铵交换4次，过滤、干燥。之后，与20g氧化铝充分混合，并加入5wt％硝酸捏合、挤条成型为 的条状物，120℃干燥12小时，500℃焙烧6小时，制备成需要的催化剂。
【实施例5】
合成具有MWW拓扑结构的MCM-22分子筛。
将铝酸纳(Al2O3 35.21wt％，Na2O 31.12wt％)14.5g溶于990g水中，加入氢氧化钠6.18g使之溶解，然后在搅拌的情况下加入有机胺模板剂六亚甲基亚胺49.5g，再加入硅溶胶(SiO2 40wt％)150g，待搅拌均匀后装入不锈钢反应釜中，在搅拌情况下于150℃晶化50小时。然后冷却，过滤结晶的固体产物，并回收结晶母液。上述固体结晶产物再经过滤、洗涤、干燥。X射线衍射仪测得所得晶体为MCM-22。经化学分析得SiO2/Al2O3摩尔比为18。
取50g干燥后的粉末样品，用1M的硝酸铵交换4次，过滤、干燥。之后，与20g氧化铝充分混合，并加入5wt％硝酸捏合、挤条成型为 的条状物，120℃干燥12小时，500℃焙烧6小时，制备成需要的催化剂。
【实施例6】
将【实施例1-5】的催化剂4.0g分别装填在固定床反应器中，然后通入异丙苯和苯的混合物料，混合物中苯异丙苯摩尔比为5。反应条件为：异丙苯重量空速为0.4h-1，反应温度为280℃，反应压力为3.0MPa。连续运转100小时，反应结果见表1。
表1
【实施例7】
将【实施例1-5】的催化剂4.0g分别装填在固定床反应器中，然后通入异丙苯和苯的混合物料，混合物中苯异丙苯摩尔比为5。反应条件为：异丙苯重量空速为0.4h-1，反应温度为300℃，反应压力为3.0MPa。连续运转100小时，反应结果见表2。
表2
【比较例1】
同【实施例6】，只是反应温度为170℃。连续运转100小时，反应结果见表3。
表3

Claims (11)

1.一种苯和异丙苯生产正丙苯的方法，包括苯和异丙苯在有效反应条件下与催化剂接触得到正丙苯的步骤；其特征在于，所述有效反应条件包括温度至少大于200℃。
2.根据权利要求1所述苯和异丙苯生产正丙苯的方法，其特征在于，所述温度为220～500℃。
3.根据权利要求2所述苯和异丙苯生产正丙苯的方法，其特征在于，所述温度为250～400℃。
4.根据权利要求3所述苯和异丙苯生产正丙苯的方法，其特征在于，所述温度为270～350℃。
5.根据权利要求1所述苯和异丙苯生产正丙苯的方法，其特征在于，所述催化剂以重量百分比计，包括以下组份：a)40～90％的沸石分子筛；b)10～60％的粘结剂；所述沸石分子筛选自具有MFI、MWW、BEA、MOR和FAU拓扑结构分子筛中的至少一种。
6.根据权利要求5所述苯和异丙苯生产正丙苯的方法，其特征在于，所述沸石分子筛具有MFI拓扑结构。
7.根据权利要求6所述苯和异丙苯生产正丙苯的方法，其特征在于，所述沸石分子筛为ZSM-5分子筛。
8.根据权利要求5所述苯和异丙苯生产正丙苯的方法，其特征在于，所述沸石分子筛SiO2/Al2O3摩尔比为10～50。
9.根据权利要求5所述苯和异丙苯生产正丙苯的方法，其特征在于，所述粘结剂选自氧化铝、氧化钛、氧化锌和氧化锆中的至少一种。
10.根据权利要求1所述苯和异丙苯生产正丙苯的方法，其特征在于，所述有效反应条件还包括压力0.5～5.0MPa，苯和异丙苯摩尔比0.1～10，异丙苯重时空速为0.1～10小时-1。
11.根据权利要求10所述苯和异丙苯生产正丙苯的方法，其特征在于，压力为1.0～4.0MPa，苯和异丙苯摩尔比为1～8，异丙苯重时空速为0.2～5小时-1。
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* Cited by examiner, † Cited by third party
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US3894104A (en) * 1973-08-09 1975-07-08 Mobil Oil Corp Aromatization of hetero-atom substituted hydrocarbons
JPS59141525A (ja) * 1983-02-02 1984-08-14 Toray Ind Inc ノルマルアルキルベンゼン類の製造方法
CN85101896A (zh) * 1983-10-17 1987-01-17 阿莫科公司 在结晶硅铝酸盐沸石为基础的催化剂中加入钼化物改进烃类转化的过程
CN1037097A (zh) * 1987-12-15 1989-11-15 环球油品公司 通过用含氟盐类处理使Cr和/或Sn取代分子筛骨架中的铝
CN1170396A (zh) * 1994-11-23 1998-01-14 埃克森化学专利公司 应用沸石结合沸石催化剂的烃转化过程
US6462248B1 (en) * 1998-09-09 2002-10-08 Toray Industries, Inc. Method for producing aromatic compounds having alkyl group with at least three carbon atoms

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3894104A (en) * 1973-08-09 1975-07-08 Mobil Oil Corp Aromatization of hetero-atom substituted hydrocarbons
JPS59141525A (ja) * 1983-02-02 1984-08-14 Toray Ind Inc ノルマルアルキルベンゼン類の製造方法
CN85101896A (zh) * 1983-10-17 1987-01-17 阿莫科公司 在结晶硅铝酸盐沸石为基础的催化剂中加入钼化物改进烃类转化的过程
CN1037097A (zh) * 1987-12-15 1989-11-15 环球油品公司 通过用含氟盐类处理使Cr和/或Sn取代分子筛骨架中的铝
CN1170396A (zh) * 1994-11-23 1998-01-14 埃克森化学专利公司 应用沸石结合沸石催化剂的烃转化过程
US6462248B1 (en) * 1998-09-09 2002-10-08 Toray Industries, Inc. Method for producing aromatic compounds having alkyl group with at least three carbon atoms

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