Tenside Phosphines and Amines

Hydroformylation Reactions Catalyzed by Transition Metal Surfactant -Phosphine Complexes 

The fact that water-soluble sulfonated phosphines may combine the properties of a ligand and a surfactant in the same molecule was first mentioned in 1978 by Wilkinson etal. [11] in their study of the hydroformylation of 1-hexene using rhodium and ruthenium catalysts modified with TPPMS (triphenylphosphine mono- 

RVR2 = -PPh2/ -0(CH2CH20)nCH3 R1/R2 = -0(CH2CH20)nCH3 /-PPh2 

The first water-soluble system specifically designed to combine both functions of a ligand and a surfactant in one molecule and applied in transition-metal-cata-lyzed conversions of highly water-insoluble substrates in micellar systems is the zwitterionic tenside trisulfoalkylated tris(2-pyridyl)phosphine, 2 (n = 0, 3, 5, 7, 9, 11) [4, 14, 72, 74]. Turnover frequencies (TOF) up to 340 h-1 were achieved in the micellar hydroformylation of 1-tetradecene to pentadecanals, according to Eq. (1), using Rh/2 catalysts at 125 °C, by fine tuning of the hydrophilic/lipophilic properties of the tenside system 2 [4, 14]. In sharp contrast, Rh/TPPTS catalysts gave only traces of pentadecanals under the same biphasic conditions. 

Surrounding the core is the Stem layer where the charged head groups (SO3) of the surfactant 2 are located together with the counterions (Na+) in a compact region a few angstroms wide. The rhodium atom of the catalyst is probably located 

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