杯芳烃磺酸催化合成环氧化合物
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摘要
以对叔丁基杯芳烃为原料,合成了杯[4]芳烃磺酸和杯[6]芳烃磺酸;分别以杯[6]芳烃磺酸和杯[4]芳烃磺酸为催化剂,催化苯乙烯和多聚甲醛在无溶剂条件下发生缩合反应生成4-苯基-1,3-二氧六环;以30%H_2O_2为氧源,催化环辛烯环氧化合成环氧环辛烷,产物结构经~1H NMR确证。并对催化剂的热稳定性和循环利用性能进行了研究,对反应条件进行了优化。
p-Sulfonic acid calix[6]arene and calix[4]arene were prepared from calixarene and used to catalyze the condensation of styrene with paraformaldehyde to afford 4-phenyl-1,3-dioxane,and the epoxidation of cyclooctene with 30% H_2O_2 as source of oxygen to afford epoxy cyclooctane.The structures were confirmed by ~1H NMR.The thermal stabilities and reusabilities were studied.The reaction conditions were optimized.
p-Sulfonic acid calix[6]arene and calix[4]arene were prepared from calixarene and used to catalyze the condensation of styrene with paraformaldehyde to afford 4-phenyl-1,3-dioxane,and the epoxidation of cyclooctene with 30% H_2O_2 as source of oxygen to afford epoxy cyclooctane.The structures were confirmed by ~1H NMR.The thermal stabilities and reusabilities were studied.The reaction conditions were optimized.
引文
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[2]RAYATI S,ABDOLALIAN P.Sonochemical syntheses of nano-sized dioxomolybdenum complexes:An efficient,selective and reusable heterogeneous nanocatalyst for oxidation of alkenes[J].Applied Catalysis A:General,2013,456:240-248.
[3]胡红定,葛倩,朱明乔.双氧水环氧化环己烯用含钨催化剂研究新进展[J].合成纤维工业,2014,37(3):43-47.
[4]MARAKATTI V S,SHANBHAG G V,HALGERI A B.Sulfated zirconia:An efficient and reusable acid catalyst for the selective synthesis of 4-phenyl-1,3-dioxane by Prins cyclization of styrene[J].Applied Catalysis A:General,2013,451:71-78.
[5]安颖,张万东,李忠波,等.杂多酸催化烯烃环氧化的研究进展[J].化学工业与工程,2005,22(4):300-304.
[6]夏洋峰,姜翠玉,安高军,等.Prins反应的研究和应用现状[J].化工进展,2016,35(S2):11-19.
[7]AMRUTE A P,SAHOO S,BORDOLOI A,et al.Mo O3/Si O2:An efficient and selective catalyst for the synthesis 1,3-dioxolane and 1,3-dioxane[J].Catalysis Communications,2009,10(10):1404-1409.
[8]REDDY S S,RAJU B D,KUMAR V S,et al.Sulfonic acid functionalized mesoporous SBA-15 for selective synthesis of 4-phenyl-1,3-dioxane[J].Catalysis Communications,2007,8(3):261-266.
[9]MORE G P,RANE M,BHAT S V.Efficient Prins cyclization in environmentally benign method using ion exchange resin catalyst[J].Green Chemistry Letters and Reviews,2012,5(1):13-17.
[10]高腾,宋河远,陈静.负载型离子液体催化芳香烯和甲醛的Prins缩合反应[J].分子催化,2016,30(3):199-206.
[11]王以轩,刘育.磺化杯芳烃的超分子组装体构筑及其功能[J].化学学报,2015,73(10):984-991.
[12]GAWHALE S,JADHAV A,RATHOD N,et al.Inclusion complex formation of ternary system:Fluoroscein-p-sulfonato calix[4]arene-Cu2+by cooperative binding[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2015,148:382-388.
[13]COSTA C,FRANCISCO V,SILVA S G,et al.Supramolecular self-assembly between an amino acidbased surfactant and a sulfonatocalixarene driven by electrostatic interactions[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2015,480:71-78.
[14]DE SOUSA S M R,FERNANDES S A,DE ALMEIDA W B,et al.Theoretical investigation on the molecular inclusion process of prilocaine into p-sulfonic acid calix[6]arene[J].Chemical Physics Letters,2016,646:52-55.
[15]刘丽梅,张岱良,宋立鹏,等.杯[4]芳烃四磺酸的合成及电化学行为[J].辽宁石油化工大学学报,2014,34(3):1-4.
[16]XIE Y,MAO L,LI L.Calix[6]arene sulfonic acids catalysed Michael reactions of indoles withα,β-unsaturated ketones in water assisted by microwave radiation[J].Journal of Chemical Research,2013,37(8):476-479.
[17]刘丽梅,张岱良,陈平.杯[4]芳烃磺酸钠催化合成乙酸正丁酯[J].石油化工高等学校学报,2014,27(3):25-28.
[18]SATHICQ A G,LIBERTO N A,FERNáNDES S A,et al.Solvent-free multicomponent synthesis of 2-arylpyridines using p-sulfonic acid calix[6]arene as a reusable catalyst[J].Comptes Rendus Chimie,2015,18(4):374-378.
[19]GUTSCHE C D,IQBAL M.Para-tert-butylcalix[4]arene[J].Organic Syntheses,1990,68:234-237.
[20]李建森,陈远荫.对叔丁基杯芳烃合成方法的改进[J].化学试剂,2000,22(3):178-183.
[21]张卫红,刘平,王军.水相体系中磷钨酸催化Prins缩合反应合成4-苯基-1,3-二氧六环[J].石油化工,2013,42(1):64-68.