Sj. Froehner et al., MICELLAR-MEDIATED GENERAL ACID-CATALYZED ACETAL HYDROLYSIS - REACTIONS IN COMICELLES, Perkin transactions. 2, (4), 1996, pp. 673-676
Anionic micelles of sodium dodecyl sulfate (SDS) increase the rates of
acid hydrolyses of dibutyl and di-tert-butyl benzaldehyde acetal (BBA
and BTBA, respectively), The rate surfactant profiles are fitted by a
pseudophase, ion-exchange, model and second-order rate constants in t
he micellar pseudophase are slightly lower than in water. In both medi
a BTBA is considerably more reactive than BBA, The reaction of BTBA is
general acid catalysed and with micellar-bound BTBA the first-order r
ate constant of hydrolysis in comicelles of SDS and sodium decyl hydro
genphosphate increases linearly with increasing mole fraction of the p
hosphate surfactant, which is a general acid catalyst in the micellar
pseudophase. However, the rate constant of the specific hydrogen ion c
atalysed hydrolysis of BBA is independent of the mole fraction of the
phosphate surfactant.