对甲酚烷基化反应催化剂的研究进展

doi:10.16085/j.issn.1000-6613.2016.01.016

化工进展 ›› 2016, Vol. 35 ›› Issue (01): 125-130.DOI: 10.16085/j.issn.1000-6613.2016.01.016

对甲酚烷基化反应催化剂的研究进展

张吕鸿¹, 王江涛¹, 肖晓明¹, 罗铭芳², 朱桃月², 张荣亚¹

1 天津大学化工学院, 天津 300072;
2 精馏技术国家工程研究中心, 天津 300072

收稿日期:2015-04-22 修回日期:2015-06-02 出版日期:2016-01-05 发布日期:2016-01-05
通讯作者: 肖晓明,工程师。E-mail:xmxiao@tju.edu.cn。
作者简介:张吕鸿(1966-),女,博士,教授,从事化工传质与分离的研究。E-mail:zhanglvh@tju.edu.cn。

Research progress of catalysts used in the alkylation reaction of p-cresol

ZHANG Lühong¹, WANG Jiangtao¹, XIAO Xiaoming¹, LUO Mingfang², ZHU Taoyue², ZHANG Rongya¹

1 School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 National Engineering Research Centre of Distillation Technology, Tianjin 300072, China

Received:2015-04-22 Revised:2015-06-02 Online:2016-01-05 Published:2016-01-05

摘要/Abstract

摘要： 主要从酸性催化剂的发展历程全面综述了分子筛、固体超强酸、离子交换树脂、杂多酸、离子液体等多种酸性催化剂的优点和缺点,并总结出对甲酚在不同催化剂作用下反应产物区域选择性的结果。通过对多种催化剂的特性和反应结果对比着重介绍了离子液体催化剂,离子液体同时拥有液体酸高密度酸性和固体酸易分离不挥发的优点,在保持着浓硫酸酸性强度的同时,还具有低蒸气压、热稳定性高、对环境无污染、功能化设计的优良特性,这为今后对甲酚烷基化反应绿色催化剂的发展提供了重要的研究方向,避免了目前工业上常用液体酸催化剂存在的污染环境设备和安全隐患等重大问题。

关键词: 对甲酚, 烷基化反应, 催化剂, 催化作用, 化学反应

Abstract: Various novel acidic catalysts in the development history of catalysts, such as molecular sieves, super solid acids, heteropoly acids, ion exchange resins, ionic liquids, are introduced.The products' regioselectivity of p-cresol under the acidic catalysts are also summarized. Through comparing the characteristics of various catalysts and reaction results, ionic liquids are introduced as key points which show both high density acidity by liquid acids and easy separation by non-volatile solid acids. Apart from the acidity of similar to sulfuric acid, ionic liquids also have good features of low consumption, stability to water and air, no pollution and functional design which provide an important research direction for development of the catalysts of p-cresol alkylation reaction. Also, problems of liquid acid catalysts used in industrial such as corrosion and safety can be avoided.

Key words: p-cresol, the alkylation reaction, catalyst, catalysis, chemical reaction

中图分类号:

TQ032.4

张吕鸿, 王江涛, 肖晓明, 罗铭芳, 朱桃月, 张荣亚. 对甲酚烷基化反应催化剂的研究进展[J]. 化工进展, 2016, 35(01): 125-130.

ZHANG Lühong, WANG Jiangtao, XIAO Xiaoming, LUO Mingfang, ZHU Taoyue, ZHANG Rongya. Research progress of catalysts used in the alkylation reaction of p-cresol[J]. Chemical Industry and Engineering Progree, 2016, 35(01): 125-130.

参考文献

[1] MhOHAN D, PITTMAN C U, STEELE P H. Pyrolysis of wood/biomass for bio-oil:a critical review[J]. Energy & Fuels,2006, 20(3):848-889.
[2] 杨续来,朱锡锋. 固体酸催化烯烃改性生物油酚类化合物研究[J]. 高等学校化学学报,2010(7):1398-1404.
[3] 李杰,时凯,李惜,等. 塑料制品的安全和环保要求与抗氧剂的选择和应用[J]. 塑料助剂,2014(4):21-26.
[4] JIN H, ANSARI M B, PARK S. Chemoselective O-versus C-alkylation of substituted phenols with cyclohexene over mesoporous ZSM-5[J]. Applied Catalysis A:General,2014,472:184-190.
[5] HUSTON R C,LEWIS W C. Action of aromatic alcohols on aromatic compounds in the presence of aluminum chloride. Ⅶ condensation of benzyl alcohol with para-cresol[J]. Journal of the American Chemical Society,1931,53(6):2379-2382.
[6] ISAGULYANTS V I,BELOV P S. Alkylation of p-cresol with isobutylene and isobutyl alcohol in the presence of cation-exchange resin KU-2[J]. Zh Prikl Khim,1964,37(8):1.
[7] MANORANJAN S,GHOSH S K. Synthesis of 2-tert-butyl-4-methylphenol[J]. Dhaka Univ Stud Part B,1990,38(2):197-198.
[8] 林富荣,颉林,周永生. Lewis酸催化对甲酚与异丁烯合成对叔丁氧基甲苯[J]. 化学试剂,2012(8):31.
[9] KRUGER J S,CHOUDHARY V,NIKOLAKIS V. Elucidating the roles of zeolite H-BEA in aqueous-phase fructose dehydration and HMF rehydration[J]. ACS Catalysis,2013,3(6):1279-1291.
[10] 张长福,张丹,李君华,等. 介孔沸石材料合成研究进展[J]. 天津化工,2015,29(1):1-6.
[11] 周治峰,石宇. ZSM-5沸石分子筛催化剂的研究进展[J]. 辽宁化工,2015,44(4):32-34.
[12] 于心玉,高珊,刘彩华,等. Hβ沸石催化合成2-叔丁基对甲酚[J]. 聚合物与助剂,2006(5):14.
[13] 李文凤,王茜,董燕飞,等. 改性Hβ沸石上对甲酚与异丁烯的烷基化反应[J]. 化学工业与工程,2007,24(3):254-257.
[14] BUTTERSACK C,WIDDECKE H,KLEIN J. The concept of variable active centres in acid catalysis:Part I. Alkylation of benzene with olefins catalyzed by ion-exchange resins[J]. Journal of Molecular Catalysis,1986,38(3):365-381.
[15] 于鲁汕,王金旺. 2-叔丁基对甲酚合成条件研究[J]. 精细石油化工, 1995(5):57-59.
[16] SANTACESARIA E,SILVANI R,WILKINSON P,et al. Alkylation of p-cresol with isobutene catalyzed by cation-exchange resins:a kinetic study[J]. Industrial & Engineering Chemistry Research,1988, 27(4):541-548.
[17] 邓廷昌,陈军,赵义军,等. MTBE合成抗氧剂T501的研究[J]. 甘肃科技,2007(1):38.
[18] 黄艳,尚宇,周健,等. 离子交换树脂在工业废水处理中的研究进展[J]. 煤炭与化工,2014,37(1):48-50.
[19] 于心玉,刘彩华,程文萍,等. Al-MCM-41介孔分子筛催化对甲酚叔丁基化反应的研究[J]. 燃料化学学报,2007,34(6):757-760.
[20] 赵昕,沈健,刘殿钊,等. 介孔分子筛SBA-15-SO₃H催化合成2-叔丁基对甲酚[J]. 化工进展,2008,27(3):404-406,411.
[21] SELVARAJ M, SINHA P K. Highly selective synthesis of t-butyl-p-cresol (TBC) by t-butylation of p-cresol with t-butyl alcohol over microporous and mesoporous catalysts[J]. Journal of Molecular Catalysis A:Chemical,2007,264(1):44-49.
[22] DEVASSY B M,SHANBHAG G V,LEFEBVRE F,et al. Alkylation of p-cresol with tert-butanol catalyzed by heteropoly acid supported on zirconia catalyst[J]. Journal of Molecular Catalysis A:Chemical, 2004,210(1):125-130.
[23] 吴冰,沈健,李会鹏,等. HPWA/SBA-15催化合成对叔丁基苯酚[J]. 工业催化,2008,16(2):41-44.
[24] KUMBAR S M,SHANBHAG G V,LEFEBVRE F,et al. Heteropoly acid supported on titania as solid acid catalyst in alkylation of p-cresol with tert-butanol[J]. Journal of Molecular Catalysis A:Chemical,2006,256(1):324-334.
[25] BHATT N, PATEL A. Liquidphase tert-butylation of cresols catalysed by 12-tungstophosphoricacid and 12-tungstosilicicacid supported onto neutral alumina[J]. Catalysis Letters,2007,113(3-4):99-103.
[26] 李三喜,徐妍如,王松. SO₄^2-/TiO₂-HZSM-5固体超强酸催化剂的制备及酯化性能[J]. 化工进展,2015,34(3):745-750.
[27] GAO Y H. Synthesize biodiesel through SO₄^2-/ZrO₂ for use as solid super acid catalyst in biodiesel production[J]. Advanced Materials Research,2014,919:2105-2108.
[28] SARISH S,DEVASSY B M,HALLIGUDI S B. tert-Butylation of p-cresol over WO_x/ZrO₂ solid acid catalysts[J]. Journal of Molecular Catalysis A:Chemical,2005,235(1):44-51.
[29] LIU X,ZHOU J,GUO X,et al. SO₃H-functionalized ionic liquids for selective alkylation of p-cresol with tert-butanol[J]. Industrial & Engineering Chemistry Research,2008,47(15):5298-5303.
[30] KONDAMUDI K,ELAVARASAN P,DYSON P J,et al. Alkylation of p-cresol with tert-butyl alcohol using benign Bronsted acidic ionic liquid catalyst[J]. Journal of Molecular Catalysis A:Chemical,2010, 321(1):34-41.
[31] 李宪昭,周立贤,李大昌,等. 在SO₃H-功能化离子液体催化下对甲酚叔丁基化反应机理[J]. 当代化工,2015,43(10):1981-1984.
[32] ZHOU J,LIU X,ZHANG S,et al. Ab initio study of the selective alkylation of m-cresol with tert-butanol catalyzed by SO₃H functionalized ionic liquids[J]. Catalysis Today,2010,149(1):232-237.
[33] BAO S H,QUAN N N,ZHANG J,et al. Alkylation of p-cresol with tert-butanol catalyzed by novel multiple-SO₃H functioned ionic liquid[J]. Chinese Journal of Chemical Engineering,2011,19(1):64-69.
[34] LI X,CAO R,LIN Q. Long-chain double SO₃H-functionalized Brønsted acidic ionic liquids catalyzed selective alkylation of phenol and p-cresol with tert-butanol[J]. Green Chemistry Letters and Reviews,2014,7(2):179-183.
[35] ALAMDARI R F,ZAMANI F G,ZEKRI N. An efficient and highly selective ortho-tert-butylation of p-cresol with methyl tert-butyl ether catalyzed by sulfonated ionic liquids[J]. Journal of the Serbian Chemical Society,2014,79(11):1337-1346.

对甲酚烷基化反应催化剂的研究进展

Research progress of catalysts used in the alkylation reaction of p-cresol

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	张明焱, 刘燕, 张雪婷, 刘亚科, 李从举, 张秀玲. 非贵金属双功能催化剂在锌空气电池研究进展[J]. 化工进展, 2023, 42(S1): 276-286.
[2]	时永兴, 林刚, 孙晓航, 蒋韦庚, 乔大伟, 颜彬航. 二氧化碳加氢制甲醇过程中铜基催化剂活性位点研究进展[J]. 化工进展, 2023, 42(S1): 287-298.
[3]	谢璐垚, 陈崧哲, 王来军, 张平. 用于SO₂去极化电解制氢的铂基催化剂[J]. 化工进展, 2023, 42(S1): 299-309.
[4]	杨霞珍, 彭伊凡, 刘化章, 霍超. 熔铁催化剂活性相的调控及其费托反应性能[J]. 化工进展, 2023, 42(S1): 310-318.
[5]	王乐乐, 杨万荣, 姚燕, 刘涛, 何川, 刘逍, 苏胜, 孔凡海, 朱仓海, 向军. SCR脱硝催化剂掺废特性及性能影响[J]. 化工进展, 2023, 42(S1): 489-497.
[6]	邓丽萍, 时好雨, 刘霄龙, 陈瑶姬, 严晶颖. 非贵金属改性钒钛基催化剂NH₃-SCR脱硝协同控制VOCs[J]. 化工进展, 2023, 42(S1): 542-548.
[7]	徐晨阳, 都健, 张磊. 基于图神经网络的化学反应优劣评价[J]. 化工进展, 2023, 42(S1): 205-212.
[8]	程涛, 崔瑞利, 宋俊男, 张天琪, 张耘赫, 梁世杰, 朴实. 渣油加氢装置杂质沉积规律与压降升高机理分析[J]. 化工进展, 2023, 42(9): 4616-4627.
[9]	王鹏, 史会兵, 赵德明, 冯保林, 陈倩, 杨妲. 过渡金属催化氯代物的羰基化反应研究进展[J]. 化工进展, 2023, 42(9): 4649-4666.
[10]	张启, 赵红, 荣峻峰. 质子交换膜燃料电池中氧还原反应抗毒性电催化剂研究进展[J]. 化工进展, 2023, 42(9): 4677-4691.
[11]	王伟涛, 鲍婷玉, 姜旭禄, 何珍红, 王宽, 杨阳, 刘昭铁. 醛酮树脂基非金属催化剂催化氧气氧化苯制备苯酚[J]. 化工进展, 2023, 42(9): 4706-4715.
[12]	葛亚粉, 孙宇, 肖鹏, 刘琦, 刘波, 孙成蓥, 巩雁军. 分子筛去除VOCs的研究进展[J]. 化工进展, 2023, 42(9): 4716-4730.
[13]	吴海波, 王希仑, 方岩雄, 纪红兵. 3D打印催化材料开发与应用进展[J]. 化工进展, 2023, 42(8): 3956-3964.
[14]	向阳, 黄寻, 魏子栋. 电催化有机合成反应的活性和选择性调控研究进展[J]. 化工进展, 2023, 42(8): 4005-4014.
[15]	王耀刚, 韩子姗, 高嘉辰, 王新宇, 李思琪, 杨全红, 翁哲. 铜基催化剂电还原二氧化碳选择性的调控策略[J]. 化工进展, 2023, 42(8): 4043-4057.