Friedel-Crafts Reaction of Anthracene with tert-Butanol

doi::0.3969/j.issn.1672-6952.2017.01.003

Journal of Liaoning Petrochemical University ›› 2017, Vol. 37 ›› Issue (1): 14-17.DOI: :0.3969/j.issn.1672-6952.2017.01.003

Previous Articles Next Articles

Friedel-Crafts Reaction of Anthracene with tert-Butanol

Received:2016-04-13 Revised:2016-05-21 Published:2017-02-24 Online:2017-03-16

蒽与叔丁醇Friedel-Crafts烷基化反应

叶金鑫,孙京,王欣,周明东

辽宁石油化工大学化学与材料科学学院,辽宁抚顺11300

通讯作者: 周明东(1980-),女,博士,教授,从事金属催化和有机合成化学的研究;E-mail:mingdong.zhou@hotmail.com。
作者简介:叶金鑫(1989-),男,硕士研究生,从事催化化学及有机合成化学的研究;E-mail:598559591@qq.com。
基金资助:
国家自然科学基金项目(21101085)。

Abstract

Abstract:

Zeolite is an efficient, environment friendly, green and specific space structure solid acid catalyst, which is widely used in petrochemical and organic synthesis. The acidic property of the Hβ zeolite was prepared by using ion-exchange. The Friedel-Crafts reaction of anthracene with tert-butanol catalyzed by the zeolite catalyst was investigated. The products were fully characterized and analyzed by GC-MS, FT-IR, H-NMR and element analysis. The mechanism of this reaction was also proposed. The results showed that the isotcane not only acted as a solvent, but also formed the tert-butyl cation to accelerate the transformation; the zeolite catalyst exhibited high catalytic activity to afford the 2-(tert-butyl)anthracene and 2,6-di-tert-butytylanthracene which had a good industrial application prospects.

Key words: Anthracene, Zeolite, Friedel-Crafts alkylation

摘要： 分子筛催化剂是一种高效、环保、绿色的具有特定空间结构的固体酸催化剂,被广泛应用于石油化工和有机合成等领域。利用离子交换方法合成了一种酸性微孔β分子筛催化剂,并且研究了该分子筛催化剂催化蒽与叔丁醇的Friedel-Crafts烷基化反应,通过GC-MS、FT-IR、1H-NMR、元素分析等手段对反应产物进行了细致的表征。在此基础上,对蒽与叔丁醇的Friedel-Crafts烷基化反应机理进行了初步的探讨。结果表明,所合成的酸性分子筛催化剂具有较高的催化活性,异辛烷不仅仅作为反应溶剂,还能与分子筛形成叔丁基碳正离子促进反应进行,反应主要生成2-叔丁基蒽和2,6-二叔丁基蒽两种产物,具有很好的工业应用前景。

关键词: 蒽, 酸性分子筛, Friedel-Crafts烷基化

YeJinxin, SunJing, WangXin, ZhouMingdong. Friedel-Crafts Reaction of Anthracene with tert-Butanol[J]. Journal of Liaoning Petrochemical University, 2017, 37(1): 14-17.

叶金鑫, 孙京, 王欣, 周明东. 蒽与叔丁醇Friedel-Crafts烷基化反应[J]. 辽宁石油化工大学学报, 2017, 37(1): 14-17.

[1]	Xiangbo Sun, Yu Hui, Jingwei Zhang, Zhiying Li, Yucai Qin, Lijuan Song. Study on Mechanism of Thiophene Alkylation Reaction on Hβ Zeolites by In⁃Situ Infrared Spectroscopy [J]. Journal of Liaoning Petrochemical University, 2023, 43(4): 66-71.
[2]	Tong Fengwei， Wang Xin， Chen Ping. lkylation of p⁃Cresol with tert⁃Butanol Catalyzed by HY Zeolite under Microwave Irradiation [J]. Journal of Liaoning Petrochemical University, 2020, 40(5): 13-17.
[3]	Cui Fuxu，Zhang Jing，Zhang Bo，Yang Liangdong，Wang Yingying，Pan Liwei. Metal⁃Loaded ZSM⁃5 Molecular Sieve Catalyzed Ozonation of Phenol Wastewater [J]. Journal of Liaoning Petrochemical University, 2019, 39(2): 10-14.
[4]	Wang Erze，Wang Xin，Chen Ping. Progress in Synthesis of Anthraquinone [J]. Journal of Liaoning Petrochemical University, 2019, 39(2): 15-20.
[5]	Xia Jiajia，Zhou Ming,Li Tiansong,Wang Xiaoning，Liu Shu,Cui Chang. Research Progress in the Nature of Adsorption and Diffusion on Molecular Sieve [J]. Journal of Liaoning Petrochemical University, 2018, 38(03): 35-39.
[6]	Li Danyang, Liu Shu Wang Xiaoning, Meng Fanli. Research Status of C₄ Olefin Oligomerization and Catalysts [J]. Journal of Liaoning Petrochemical University, 2016, 36(5): 1-5.
[7]	Lin Wei, Yi Hao, Wang Jingyun, Wang Qiang, Ye Jinxin, Zang Shuliang. Preparation of Supported Perrhenate Ionic Liquids [J]. Journal of Liaoning Petrochemical University, 2016, 36(3): 12-14.
[8]	Cheng Yun,Yang Ying,Luo Genxiang. Green Synthesis of Methyl Oleate Catalyzed by H3PWl2O40/Yβ [J]. Journal of Liaoning Petrochemical University, 2014, 34(5): 11-14.
[9]	Jin Cong， Shen Jian. Processing Conditions of Alkylation of  Thiophene with Laurylene over USY Zeolite [J]. Journal of Liaoning Petrochemical University, 2014, 34(2): 29-32.
[10]	LIU Chun-sheng， LUO Gen-xiang. Synthesis of Cyclohexyl Acetate Catalyzed by Y-β Composite Zeolite Supported Phosphotungstic Acid [J]. Journal of Liaoning Petrochemical University, 2012, 32(4): 24-27.
[11]	ZHU Jin-zhu， FENG Rui-jiang, SHEN Jian. Removal of Basic Nitrogen Compounds FromOil by Adsorption With RE/Y Zeolite [J]. Journal of Liaoning Petrochemical University, 2012, 32(2): 12-15.
[12]	LIU Li-ming,WANG Hong-guo, JIN Ling-ling, JU Xiu-fang, SONG Li-juan. Adsorptive Desulfurization of Different Sulfur Compounds on Cu(Ⅰ)Y Zeolites [J]. Journal of Liaoning Petrochemical University, 2009, 29(3): 1-4.
[13]	DUAN Lin - hai,SONG Li - juan,et al. Simulation and Ex periment of Thiophene and Benzene Adsorpt ion on Y - Zeoli tes [J]. Journal of Liaoning Petrochemical University, 2007, 27(1): 1-3.
[14]	WANG Li,WANG Hai -y an,CHEN Jin -peng. Macrokinetics Studying on Catalyic Sy nthesis of TAME by β Zeolite [J]. Journal of Liaoning Petrochemical University, 2006, 26(1): 45-47.

Friedel-Crafts Reaction of Anthracene with tert-Butanol

蒽与叔丁醇Friedel-Crafts烷基化反应

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 14

Recommended Articles

Metrics