Premium
Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis
Author(s) -
Ferreira Michel,
Bricout Hervé,
Azaroual Nathalie,
Landy David,
Tilloy Sébastien,
Hapiot Frédéric,
Monflier Eric
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100837
Subject(s) - chemistry , micelle , hydroformylation , catalysis , ionic liquid , aqueous solution , stoichiometry , ionic bonding , amphiphile , rhodium , regioselectivity , aldehyde , decantation , cyclodextrin , organic chemistry , inorganic chemistry , combinatorial chemistry , ion , copolymer , polymer
When mixed with a water‐soluble phosphane capable of self‐assembling into micelles, native or modified β‐cyclodextrins (β‐CDs) show very contrasting behavior depending on their neutral or ionic nature. In the post‐micellar region, neutral β‐CDs led to a micelle destructuring. Conversely, micelles remained stable over a well‐defined range of ionic β‐CD concentrations. In that case, the micelle destruction was only observed when using a large excess of ionic β‐CDs. The catalytic performances of these micellar systems have been evaluated in a rhodium‐catalyzed hydroformylation reaction of 1‐decene. We showed that, using ionic β‐CDs, the catalytic activity could be improved without a detrimental impact upon the regioselectivity. A linear/branched aldehyde ratio as high as 8.6 could be achieved. The best results were obtained with stoichiometric quantities of ionic randomly methylated β‐CDs with respect to the phosphane with a beneficial effect on the decantation at the end of the reaction.