Highly effective tandem hydroformylation-acetalization of olefins using a long-life Bronsted acid-Rh bifunctional catalyst in ionic liquid-alcohol systems

被引：25

作者：

Jin, Xin ^{[1
,2
]}

Zhao, Kun ^{[1
]}

Cui, Feifei ^{[1
]}

Kong, Fangfang ^{[1
]}

Liu, Qiangqiang ^{[1
]}

机构：

[1] Qingdao Univ Sci & Technol, Coll Chem Engn, Qingdao 266042, Peoples R China

[2] Xinjiang Univ, Minist Educ, Key Lab Oil & Gas Fine Chem, Urumqi 830046, Peoples R China

来源：

GREEN CHEMISTRY | 2013年 / 15卷 / 11期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC HYDROFORMYLATION; ARYL ALKENES; ACETALS; COMPLEXES; 1-HEXENE; HYDROESTERIFICATION;

D O I：

10.1039/c3gc41231h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A robust and highly effective tandem hydroformylation-acetalization of olefins using a Bronsted acid-Rh bifunctional catalyst (ARBC) in ionic liquid alcohol systems is reported. The key feature of the ARBC is its use of a zwitterionic phosphine ligand bearing an amino acid tag. This novel ARBC shows an excellent catalytic efficiency and a long service life without a significant drop in both the hydroformylation efficiency and the acetalization efficiency or Rh loss for more than seventeen cycles. We believe that the long-term high activity and acetal selectivity mainly benefit from the synergy between the acidic active site and the Rh active site on the ARBC and the highly effective immobilization and recycling of ARBC in ionic liquid alcohol systems due to the strong affinity of ARBC for the ionic liquid.

引用

页码：3236 / 3242

页数：7

共 28 条

[1] Hydroformylation of styrene catalyzed by a rhodium thiolate binuclear catalyst supported on a cationic exchange resin [J].

Balué, J ;

Bayón, JC .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 137 (1-3) :193-203

[2] Selection process of new solvents in temperature-dependent multi-component solvent systems and its application in isomerising hydroformylation [J].

Behr, A ;

Henze, G ;

Obst, D ;

Turkowski, B .

GREEN CHEMISTRY, 2005, 7 (09) :645-649

[3] Water soluble phosphines -: Part XIII.: Chiral phosphine ligands with amino acid moieties [J].

Brauer, DJ ;

Schenk, S ;

Rossenbach, S ;

Tepper, M ;

Stelzer, O ;

Häusler, T ;

Sheldrick, WS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 598 (01) :116-126

[4] SN[CO(CO)4]4, A BIFUNCTIONAL CATALYST OF THE HYDROFORMYLATION-ACETALIZATION REACTION [J].

CABRERA, A ;

MORTREUX, A ;

PETIT, F .

JOURNAL OF MOLECULAR CATALYSIS, 1988, 47 (01) :11-15

[5] Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals [J].

Climent, Maria J. ;

Corma, Avelino ;

Iborra, Sara .

CHEMICAL REVIEWS, 2011, 111 (02) :1072-1133

[6] Hydrocarbonylation of prop-2-en-1-ol catalysed by zeolite-encapsulated rhodium species: Chemoselectivity effects imposed by the zeolite support [J].

Currie, AWS ;

Andersen, JAM .

CATALYSIS LETTERS, 1997, 44 (1-2) :109-111

[7] Formation of Acetals under Rhodium-Catalyzed Hydroformylation Conditions in Alcohols [J].

Diebolt, Olivier ;

Cruzeuil, Clement ;

Muller, Christian ;

Vogt, Dieter .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (04) :670-677

[8] Hydroformylation of 1-hexene using Rh/TPPTS complex exchanged on anion exchange resin: kinetic studies [J].

Diwakar, MM ;

Deshpande, RM ;

Chaudhari, RV .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 232 (1-2) :179-186

[9] Tandem reaction sequences under hydroformylation conditions:: New synthetic applications of transition metal catalysis [J].

Eilbracht, P ;

Bärfacker, L ;

Buss, C ;

Hollmann, C ;

Kitsos-Rzychon, BE ;

Kranemann, CL ;

Rische, T ;

Roggenbuck, R ;

Schmidt, A .

CHEMICAL REVIEWS, 1999, 99 (11) :3329-3365

[10] Rh(I) or Rh(III) supported on MCM-41-catalyzed selective hydroformylation-acetalization of aryl alkenes: Effect of the additives [J].

El Ali, B ;

Tijani, J ;

Fettouhi, M .

APPLIED CATALYSIS A-GENERAL, 2006, 303 (02) :213-220

← 1 2 3 →