Tr-liquid system in the synthesis of dialkyl peroxides using tetraalkylammonium salts as phase-transfer catalysts

被引:14
作者
Baj, Stefan [1 ]
Siewniak, Agnieszka [1 ]
机构
[1] Silesian Tech Univ, Chair Chem Organ Technol & Petrochem, PL-44100 Gliwice, Poland
关键词
Dialkyl peroxides; Hydroperoxides; Phase-transfer catalysts; Liquid-liquid-liquid PTC; BENZYL-CHLORIDE; 3RD-LIQUID PHASE; ETHER SYNTHESIS; SODIUM SULFIDE; O-ALKYLATION; SELECTIVITY; KINETICS; 3RD-PHASE; RATES; INTENSIFICATION;
D O I
10.1016/j.apcata.2010.07.015
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
A highly effective method to synthesise dialkyl peroxides from alkyl hydroperoxides and alkyl bromides in a liquid-liquid-liquid system using tetraalkylammonium salts as phase-transfer catalysts is reported. This process was conducted in the presence of highly concentrated aqueous KOH solutions and cyclohexane as an organic solvent. In a liquid-liquid-liquid system, the phase-transfer catalyst forms an insoluble third-liquid phase between the organic and aqueous phases that enables the catalyst to be recycled multiple times. Dialkyl peroxides were obtained in high yields and with 100% selectivity. (c) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:208 / 213
页数:6
相关论文
共 31 条
[11]   Characteristics of third phase for reaction of benzyl chloride with sodium sulfide in phase transfer catalytic system [J].
Ido, T ;
Susaki, T ;
Jin, G ;
Goto, S .
APPLIED CATALYSIS A-GENERAL, 2000, 201 (01) :139-143
[12]   Formation of a third liquid phase and its reuse for dibenzyl ether synthesis in a tetraalkylammonium salt phase transfer catalytic system [J].
Jin, G ;
Morgner, H ;
Ido, T ;
Goto, S .
CATALYSIS LETTERS, 2003, 86 (04) :207-210
[13]   Effect of third-phase properties on benzyl-n-butyl ether synthesis in phase transfer catalytic system [J].
Jin, G ;
Ido, T ;
Goto, S .
CATALYSIS TODAY, 2001, 64 (3-4) :279-287
[14]   THE CHEMISTRY OF HYDROPEROXIDES .6. THE THERMAL DECOMPOSITION OF ALPHA-CUMYL HYDROPEROXIDE [J].
KHARASCH, MS ;
FONO, A ;
NUDENBERG, W .
JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (01) :113-127
[15]  
LANDINI D, 1993, GAZZ CHIM ITAL, V123, P19
[16]   Kinetics for etherification of sodium o-nitrophenoxide via third-liquid phase-transfer catalysis [J].
Lin, PJ ;
Yang, HM .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 235 (1-2) :293-301
[17]   Phase transfer catalysis (Reprinted from Interfacial Catalysis, pg 159-201, 2003) [J].
Makosza, M ;
Fedorynski, M .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2003, 45 (3-4) :321-367
[18]   Remarks on the mechanism of phase-transfer catalyzed carbanion generation in two-phase systems [J].
Makosza, M ;
Krylowa, I .
TETRAHEDRON, 1999, 55 (20) :6395-6402
[19]   ROLE OF A 3RD LIQUID-PHASE IN PHASE-TRANSFER CATALYSIS [J].
MASON, D ;
MAGDASSI, S ;
SASSON, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7229-7232
[20]   HYDROXIDE ION INITIATED REACTIONS UNDER PHASE-TRANSFER CATALYSIS CONDITIONS - MECHANISMS AND IMPLICATIONS [J].
RABINOVITZ, M ;
COHEN, Y ;
HALPERN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :960-970