Effect of alkyl chain length, head group and nature of the surfactant on the hydrolysis of 1,3-benzoxazine-2,4-dione and its derivatives

Al‐Ayed, Abdullah Sulaiman; Ali, Mushir; Al‐Lohedan, Hamad A.; Al-Sulaim, A. M.; Issa, Zuheir A.

doi:10.1016/j.jcis.2011.05.005

Cited by 19 publications

(12 citation statements)

References 29 publications

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“…These results may be compared with experimental observations of the larger micellar binding constant of PSa -, (K S ) in CTABr (K S = 7000 M -1 ) than that in TTABr (K S = 3660 M -1 ) obtained under the same experimental conditions. Several studies have reported that for the surfactants of the same headgroups, decrease in hydrophobic chain length will decrease the values of micellar binding constant of substrate, K S [57][58][59]. Shorter hydrophobic chain length will cause a smaller aggregation number of micelles [60], which reflects the decrease in micellar size for the surfactant of the same head group [61].…”

Section: Resultsmentioning

confidence: 99%

Counterion‐Induced Cationic Flexible Nanoparticle Catalytic of Piperidinolysis of Phenyl Salicylate

Noh

Khalid

Ariffin

et al. 2017

J Surfact & Detergents

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The removal of PSa− from bulk aqueous phase to the pseudo‐micellar phase by halobenzoate counterion X is responsible for the monotonic increase in kobs (pseudo first‐order rate constants) with the increase in the values of [MX] where MX = sodium salts of 2‐, and 4‐halobenzoic acids. The values of ion exchange constants, KnormalXBr or RnormalXBr for X = 2‐ and 4‐halobenzoate ions in the presence of tetradecyltrimethylammonium bromide (TTABr) were calculated from the apparent catalytic rate constants, Xkcat which represent the catalytic effect of CFN. Larger values of KnormalXBr or RnormalXBr were observed for X = 4‐halobenzoate ions than that for X = 2‐halobenzoate ions due to isomeric factors. The values of KnormalXBr or RnormalXBr determined in the presence of TTABr were compared with previously determined KnormalXBr or RnormalXBr values in the presence of cetyltrimethylammonium bromide (CTABr). The values of KnormalXBr or RnormalXBr are nearly 8 ~ 9‐fold larger for 4‐IBz−, 4‐BrBz− and 4‐ClBz− compared to the respective values of X = 2‐IBz−, 2‐BrBz− and 2‐ClBz−. The values of KnormalXBr or RnormalXBr for X = 4‐FBz− is nearly 3‐fold larger than that for X = 2‐FBz−. The values of KnormalXBr or RnormalXBr for X = 2‐ and 4‐halobenzoates are significantly smaller in the presence of TTABr than these in the presence of CTABr nanoparticles.

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Section: Resultsmentioning

confidence: 99%

Counterion‐Induced Cationic Flexible Nanoparticle Catalytic of Piperidinolysis of Phenyl Salicylate

Noh

Khalid

Ariffin

et al. 2017

J Surfact & Detergents

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“…Again, the conductivity versus profile shows the increase in conductivity with increase in the which is also associated with viscosity of microemulsions and reverse micelles of CTAB. At > 50, the CTAB/water micelles of sufficient numbers collide and produce a channel that carries ions leading to increase in conductivity and viscosity increases due to the presence of micelle core [30]. At < 20, the CTAB/1-butanol reverse micelles are formed that allow transport of ions through the water that filled cores and the viscosity slightly increases due to the interaction of water droplets [39].…”

Section: Correlations Of Physicochemical Properties Of Ctab/ Cyclohexmentioning

confidence: 99%

“…At pH 13, curcumin undergoes rapid degradation by alkaline hydrolysis in the SDS micelles whereas it is greatly suppressed in the presence of either CTAB or dodecyltrimethylammonium bromide micelle [29]. The effect of cationic surfactants with varying hydrophobic chains and with different head groups and anionic surfactant (SDS) on the rate of alkaline hydrolysis of the carsalam and its -substituted derivatives have been investigated by Al-Ayed et al [30]. The plots of observed rate constant ( obs ) versus [surfactants] for degradation of indomethacin under alkaline condition were curved with negative slopes for ethoxylated lanolin, polysorbate 80; but, with the cetrimonium bromide, the plots showed a marked positive change in obs as the [surfactant] passed through the CMC [31].…”

Section: Introductionmentioning

confidence: 99%

Acid Hydrolysis of Bromazepam Catalyzed by Micelles, Reverse Micelles, and Microemulsions

Begum¹,

Mollah²,

Rahman³

et al. 2015

Journal of Chemistry

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Kinetics of the acid hydrolysis of bromazepam (Bz) has been investigated in micelles, reverse micelles, and microemulcions of cetyltrimethylammonium bromide (CTAB) by spectrophotometric method. The rate of the acid hydrolysis of Bz was found to be enhanced both below and above the critical micelle concentration (CMC) of CTAB in aqueous solution. The pseudo-first-order rate constant ( ) shows an initial decrease for both low and high H + concentrations. With further increase in [CTAB], at low [H + ], the attains an almost constant value, while, at high [H + ], the passes through a maximum and then decreases. The kinetic data for catalysis by micelles of CTAB was interpreted with the pseudophase ion exchange (PIE) model. In CTAB/cyclohexane/1-butanol/water microemulsions, as the water to surfactant ratio ( ) increases, the physicochemical properties and droplet sizes of microemulsions significantly change and distinct changes in reaction environment can be marked. The rate of the hydrolysis reaction exhibits excellent correlation with the physicochemical properties and droplet sizes of the microemulsions and reverse micelles of CTAB. At [H + ] = 0.001 M, in reverse micelles and microemulsions of CTAB, the of the acid hydrolysis of Bz decreases sharply followed by a slight increase with increasing .

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“…The alkaline hydrolysis of acetylsalicylic acid in cationic micelles was studied by different authors and values of k m2 approximately 100-140 times smaller than k w were found [14] and [25]. The hydrolysis of 1,3-benzoxazine-2,4-dione and its derivatives yielded k m2 values 300-600 times smaller than k w [26].…”

Section: Reaction In Micelles Functionalized With Oh −mentioning

confidence: 99%

Micellar effects on aromatic esters hydrolysis

Brandariz¹,

Iglesias²

2014

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Highlights Cationic surfactants catalyze the alkaline hydrolysis of aromatic esters.  Variation of counter-ions association degree to micelles explains experimental data.  Adsorption equilibrium constants of esters do not depend on micelle counter-ion. AbstractThe alkaline hydrolysis of two aromatic esters, 2-naphthyl acetate (2NA) and phenyl acetate (PhA) has been tackled in this work. The reaction has been followed in water and in the presence of cationic surfactants with different chain lengths: dodecyltrimethylammonium bromide (DTABr), tetradecyltrimethylammonium bromide (TTABr), and hexadecyltrimethylammonium bromide (CTABr) and the corresponding hydroxides (DTAOH, TTAOH and CTAOH) at 25 °C. The pseudo-first order rate constants increase with surfactant concentration in the presence of surfactants with reactive counter-ions, while a maximum is reached for bromide surfactants with a constant concentration of hydroxyl ion. Both, the association equilibrium constants of 2NA and PhA with micelles and the rate constant in this medium were determined. The degree of counter-ion association to micelles was considered as a variable parameter, using the adsorption equilibrium of bromide and hydroxide ions to the micelle. Graphical abstract Keywords Hydrolysis; Ion-exchange equilibrium; Micelles; Mass action model; Pseudo-phase model Corresponding author. Tel.: +34 981 167000x2068; fax: +34 981 167065.

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Effect of alkyl chain length, head group and nature of the surfactant on the hydrolysis of 1,3-benzoxazine-2,4-dione and its derivatives

Cited by 19 publications

References 29 publications

Counterion‐Induced Cationic Flexible Nanoparticle Catalytic of Piperidinolysis of Phenyl Salicylate

Counterion‐Induced Cationic Flexible Nanoparticle Catalytic of Piperidinolysis of Phenyl Salicylate

Acid Hydrolysis of Bromazepam Catalyzed by Micelles, Reverse Micelles, and Microemulsions

Micellar effects on aromatic esters hydrolysis

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