Highly selective synthesis of acetylferrocene by acylation of ferrocene over zeolites

被引：28
作者：
Bejblova, Martina
Zones, Stacey I.
Cejka, Jiri
机构：
[1] Acad Sci Czech Republic, J Heyrovsky Inst Phys Chem, CZ-18223 Prague 8, Czech Republic
[2] Chevron Energy & Technol Co, Richmond, CA 94802 USA
来源：
APPLIED CATALYSIS A-GENERAL | 2007年 / 327卷 / 02期
关键词：
acetylferrocene; acylation; zeolites; structural types;
D O I：
10.1016/j.apcata.2007.05.023
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Zeolites with different structure and concentration of acid sites were investigated in a liquid phase acylation of ferrocene with acetic anhydride. It was found that the conversion of ferrocene increased in the order: medium pore zeolites < 1D large pore zeolites < 3D large pore zeolites. Zeolite SSZ-33 with interconnecting 10 and 12-membered rings exhibited a slightly lower conversion compared with mordenite. The increase in the conversion of ferrocene was observed with decreasing Si/Al ratio for the given zeolite structure. Both Broensted and Lewis acid sites contribute to the catalytic activity of zeolites in ferrocene acylation. Mono-acylated ferrocene (acetylferrocene) was synthesized by this reaction with almost 100% selectivity. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码：255 / 260
页数：6
相关论文
共 27 条
[11]   Acylation of 2-methoxynaphthalene in the presence of modified zeolite HBEA [J].
Heinichen, HK ;
Hölderich, WF .
JOURNAL OF CATALYSIS, 1999, 185 (02) :408-414
[12]   Novel solid acid catalyst, bentonite-supported polytrifluoromethanesulfosiloxane for Friedel-Crafts acylation of ferrocene [J].
Hu, RJ ;
Li, BG .
CATALYSIS LETTERS, 2004, 98 (01) :43-47
[13]   A convenient synthesis of E-alkenylferrocenes [J].
Jary, WG ;
Mahler, AK ;
Purkathofer, T ;
Baumgartner, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 629 (1-2) :208-212
[14]   Reactions of m-xylene on zeolites with intersecting medium and large pores -: Part 2:: aluminum population in structures with CON topology [J].
Jones, CW ;
Zones, SI ;
Davis, ME .
MICROPOROUS AND MESOPOROUS MATERIALS, 1999, 28 (03) :471-481
[15]   On the role of zeolite structure and acidity in toluene acylation with isobutyric acid derivatives [J].
Klisáková, J ;
Cerveny, L ;
Cejka, J .
APPLIED CATALYSIS A-GENERAL, 2004, 272 (1-2) :79-86
[16]   The Friedel-Crafts reactivity of (eta(5)-cyclopentadienyl)dicarbonylcobalt [J].
Mabrouk, ST ;
Hart, WP ;
Rausch, MD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 527 (1-2) :43-49
[17]  
Metivier P., 2001, FINE CHEM HETEROGENE, P161
[18]   ACETYLATION OF FERROCENE - A STUDY OF THE FRIEDEL-CRAFTS ACYLATION MECHANISM AS MEASURED BY HPLC USING AN INTERNAL STANDARD [J].
NEWIRTH, TL ;
SROUJI, N .
JOURNAL OF CHEMICAL EDUCATION, 1995, 72 (05) :454-456
[19]   Structure activity of 3-aryl-1,3-diketo-containing compounds as HIV-1 integrase inhibitors [J].
Pais, GCG ;
Zhang, XC ;
Marchand, C ;
Neamati, N ;
Cowansage, K ;
Svarovskaia, ES ;
Pathak, VK ;
Tang, Y ;
Nicklaus, M ;
Pommier, Y ;
Burke, TR .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (15) :3184-3194
[20]   Selective monoacylation of ferrocene - An eco-friendly procedure on the solid phase of alumina [J].
Ranu, BC ;
Jana, U ;
Majee, A .
GREEN CHEMISTRY, 1999, 1 (01) :33-34
123