Efficient sulfonic acid type ionic liquid catalyst for synthesis of methyl 4-tert-butylbenzoate
WU Qin1, CHENG Ya-ran1, SONG Shu-fen1, LI Han-sheng1, SHI Da-xin1, ZHANG Yao-yuan1, ZHAO Yun1, JIAO Qing-ze1,2
1. School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China; 2. School of Materials and Environment, Zhuhai Campus, Beijing Institute of Technology, Zhuhai 519085, China
Abstract: In the catalytic synthesis reaction of p-tert-butyl methyl benzoate (MPTBBA),the catalyst may cause damage to equipment due to common shortcomings,and is difficult to be separated,which will cause certain troubles to subsequent processing.Sulfonic acid type ionic liquid is taken as the catalyst,and its acidity is characterized.The catalytic reaction performance is studied under different catalyst structures,reaction temperatures,catalyst dosages and molar ratios between feedstocks.It is found that the conversion rate of p-tert-butylbenzoic acid (PTBBA) can reach 90% after 2.5 h of reaction by using pyridine 1,4-butane sulfolactone hydrogen sulfate ionic liquid as catalyst when reaction temperature is at 140℃,and the molar ratio of methanol,PTBBA and ionic liquid is 1 000∶100∶1.It is shown from characterization on the acidity of sulfonic acid type ionic liquid that the catalytic activity of ionic liquid is related to its amount of acid.The higher the amount of acid,the higher the catalytic activity of sulfonic acid type ionic liquid.
[1] Bleckmann A,Wille C,Scherner C,et al.Cosmetic composition used for UV-protection sunscreen agent,comprises ethanol,1,4-dioxacycloheptadecane-5,17-dione and 1-(4-methoxyphenyl)ethenyl 4-tert-butylbenzoate compound:WO2017036662-A1[P].2017-03-09. [2] Zhang Y.Modifying vinyl acetate/ethylene emulsion and vinyl 4-tert-butylbenzoate comprises e.g.adding vinyl acetate/ethylene emulsion into the reaction kettle,adding emulsifier and deionized water,and adding liquid 4-tert-butylbenzoate:CN108383947-A[P].2018-08-10. [3] Katayama A,Senboku H,Hara S.Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in the presence of carbon dioxide[J].Tetrahedron,2016,72(31):4626-4636. [4] Shen J,Ikai T,Shen X,et al.Synthesis and immobilization of amylose derivatives bearing a 4-tert-butylbenzoate group at the 2-position and 3,5-dichlorophenylcarbamate/3-(triethoxysilyl)propylcarbamate groups at 3- and 6-positions as chiral packing material for HPLC[J].Chemistry Letters,2010,39(5):442-444. [5] De Polo K F.4-Tert.-butyl-4'-methoxy-di:Benzoyl-methane-useful as UV A filter for sun screen cosmetics:US4387089[P].1983-06-07. [6] 程建华,汪晓军,吴崇财,等.防晒剂丁基甲氧基二苯甲酰甲烷(巴松1789)的合成工艺研究[J].香料香精化妆品,2002,(3):8-10. [7] 丁成荣,谢思泽,张翼,等.紫外线吸收剂丁基甲氧基二苯甲酰甲烷(巴松1789)的合成[J].浙江工业大学学报,2011,39(1):21-23. [8] 王敏,宋志国,姜恒,宫红.甲基磺酸催化合成对叔丁基苯甲酸甲酯的新工艺[J].香料香精化妆品,2007,(5):11-13. [9] 何慧红.对叔丁基苯甲酸甲酯的硫酸钛催化反应研究[J].上海应用技术学院学报,2008,8(4):14-15. [10] 胡智燕,罗书平,许丹倩.酸性离子液体催化合成N-(3-亚戊基)-3,4-二甲基苯胺[J].现代农药,2011,10(5):32-33,47. [11] 胡为民,赵英红,等.无水三氯化铁催化合成对叔丁基苯甲酸甲酯[J].河南科学,2002,20(5):508-510. [12] 罗荣.4-叔丁基苯甲酸甲酯的合成[J].江西医学院学报,2003,(6):150. [13] 魏丹,李敏谊.对叔丁基苯甲酸甲酯的合成研究[J].应用化工,2008,(6):670-672. [14] 柴小超.离子液体催化合成中长碳链结构酯的研究[D].郑州:河南工业大学,2014. [15] 张星辰.离子液体-从理论基础到研究进展[M].北京:化学工业出版社,2009:1-9. [16] 李贺,赵地顺.磷酸酯类离子液体对纤维素溶解性能的研究[J].材料导报:研究篇,2012,26(4):89-92. [17] 赵地顺,刘猛帅.离子液体对纤维素溶解性能的研究进展[J].材料导报:综述篇,2011,25(6):84-87. [18] 黎良枝,龚润曾,顾敏娜.吡啶丙基磺酸离子液体催化乙酸与苯酚反应的研究[J].化学教学,2010,12(7):12-13. [19] Fang D,Yang J M,Liu Z L.Eco-friendly synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by ionic liquid in squeous media[J].Journal of Heterocyclic Chemistry,2011,48(2):468-472. [20] Fang D,Fei Z H,Liu Z L.Functionalized ionic liquid as the recyclable catalyst for mannich-type reaction in aqueous media[J].Catalysis Communications,2009,10(8):1267-1270. [21] Zhu W S,Ding Y X,Li H M,et al.Application of a self-emulsifiable task-specific ionic liquid in oxidative desulfurization of fuels[J].RSC Advances,2013,3(12):3893-3898. [22] Cybulski J,Wisniewska A,Kulig-Adamiak A,et al.Mandelate and prolinate ionic liquids:Synthesis,characterization,catalytic and biological activity[J].Tetrahedron Letters,2011,52(12):1325-1328. [23] Suppes G,Goff M J.Transesterification of soybean oil with zeolite and metal catalysts[J].Applied Catalysis A:General,2004,257(2):213-223. [24] 郝羽.磺酸类离子液体催化制备聚甲氧基甲缩醛的研究[D].北京:北京理工大学,2012. [25] 宋淑芬.酸催化酯化反应合成对叔丁基苯甲酸甲酯的研究[D].北京:北京理工大学,2017. [26] 高伟.新型Brφnsted-Lewis双酸性离子液体的合成及表征[D].天津:河北工业大学,2010. [27] 刘秀梅.SO3-H功能化离子液体的合成及其催化性能的研究[D].大连:大连理工大学,2008. [28] 郭小婷.酸性功能化离子液体催化合成生物柴油[D].福州:福州大学,2016. [29] 何慧红.对叔丁基苯甲酸甲酯的硫酸钛催化反应研究[J].上海应用技术学院学报:自然科学版,2008,(4):290-292.