A new, alternative, halogen-free synthesis for the fragrance compound Melonal using zeolites and mesoporous materials as oxidation catalysts

被引:39
作者
Corma, A [1 ]
Iborra, S [1 ]
Mifsud, M [1 ]
Renz, M [1 ]
机构
[1] Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Valencia 46022, Spain
关键词
Baeyer-Villiger oxidation; citral; melonal; solid Lewis acid; tin centre;
D O I
10.1016/j.jcat.2005.06.006
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
At present Melonal (2,6-dimethyl-5-hepten-1-al) fragrance is industrially produced by a Darzens reaction from 6-methyl-5-hepten-2-one, with ethylchloroacetate as reagent. We present here a novel halogen-free synthesis strategy that involves the chemoselective oxidation of Citral (3,7-dimethyl-6-octen-1-al), a common compound in the fragrance industry, with H(2)O(2) and Sn-Beta or Sn-MCM-41 as catalysts. The performance of tin Lewis acid sites is compared with other potential catalytic sites, and it is found that aluminium Bronsted acid sites and zirconium or titanium Lewis acid sites are less efficient and selective than Sn. In the case of Ti, epoxidation by-products could be found. The re-usability of Sn-Beta zeolite is discussed, as is the heterogeneity of the reaction. (c) 2005 Elsevier Inc. All rights reserved.
引用
收藏
页码:96 / 100
页数:5
相关论文
共 19 条
[1]  
BAUER K, 1997, COMMON FRAGRANCE FLA, P35
[2]  
BAUER K, 1997, COMMON FRAGRANCE FLA, P15
[3]  
Behr A, 2000, EUR J LIPID SCI TECH, V102, P212, DOI 10.1002/(SICI)1438-9312(200003)102:3<212::AID-EJLT212>3.0.CO
[4]  
2-2
[5]  
BORONAT M, IN PRESS CHEM EUR J
[6]   A new environmentally benign catalytic process for the asymmetric synthesis of lactones:: Synthesis of the flavouring δ-decalactone molecule [J].
Corma, A ;
Iborra, S ;
Mifsud, M ;
Renz, M ;
Susarte, M .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :257-262
[7]   One-pot synthesis of phenols from aromatic aldehydes by Baeyer-Villiger oxidation with H2O2 using water-tolerant Lewis acids in molecular sieves [J].
Corma, A ;
Fornés, V ;
Iborra, S ;
Mifsud, M ;
Renz, M .
JOURNAL OF CATALYSIS, 2004, 221 (01) :67-76
[8]   Water-resistant solid Lewis acid catalysts: Meerwein-Ponndorf-Verley and Oppenauer reactions catalyzed by tin-beta zeolite [J].
Corma, A ;
Domine, ME ;
Valencia, S .
JOURNAL OF CATALYSIS, 2003, 215 (02) :294-304
[9]   Sn-MCM-41 - a heterogeneous selective catalyst for the Baeyer-Villiger oxidation with hydrogen peroxide [J].
Corma, A ;
Navarro, MT ;
Nemeth, L ;
Renz, M .
CHEMICAL COMMUNICATIONS, 2001, (21) :2190-2191
[10]   Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer-Villiger oxidations [J].
Corma, A ;
Nemeth, LT ;
Renz, M ;
Valencia, S .
NATURE, 2001, 412 (6845) :423-425