Synthesis of branched cores by poly-O-alkylation reaction under phase transfer conditions. A systematic study

Landeros, José M.; Silvestre, Hugo A.; Guadarrama, Patricia

doi:10.1016/j.molstruc.2013.01.034

Cited by 2 publications

(4 citation statements)

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“…From Table 5, it is clear that both TBAB and TBPB catalysts show higher activity. The order catalytic reactivity of PTC's are TBPB > TBAB > TBAI approximately equal to TBAHS > TBAC [35,36]. This indicates that a more lipophilic quaternary cation more easily solvates the solid reactant anion, thus a faster initial reaction rate was obtained.…”

Section: Effect Of Different Phase-transfer Catalystsmentioning

confidence: 94%

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Abimannan¹,

Rajendran²

2016

Bull. Chem. React. Eng. Catal.

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In this paper, the synthesis of ethyl 2-(naphthalen-2-yloxy)acetate from β-naphthol and ethyl 2-bromoacetate under ultrasound and catalyzed by quaternary ammonium salt in solid-liquid heterogeneous condition was described. Trace amount of water play a major role in this solid-liquid reaction. The reaction follows pseudo first order rate law. The apparent rate constant of the organic phase reaction was obtained form the experimental data. The combination of small amount of tetrabutylammonium bromide (TBAB) and ultrasound (kapp = 25.22×10 -3 min -1 ) shows several fold enhanced rate of the reaction than the conventional operation (kapp = 6.42×10 -3 min -1 for TBAB only). The rate constant increases (0.05 to 0.3 g) with increase in the concentration of catalyst (from kapp = 10.12×10 -3 min -1 to kapp = 34.46×10 -3 min -1 ). The other kinetic effects such as, effect of agitation speed, kind of frequency of ultrasound, kind of various quantity of K2CO3, quantity of water, temperature, different quaternary ammonium salts, solvents and volume of organic solvents on the conversion of ethyl 2-bromoacetate and apparent rate constant were investigated in detail and rational explanations are provided.

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Section: Effect Of Different Phase-transfer Catalystsmentioning

confidence: 94%

Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Abimannan¹,

Rajendran²

2016

Bull. Chem. React. Eng. Catal.

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“…conditions (0.5 equiv. tetrabutylammonium bromide, NaOH 50%) 25 achieved a rich mixture of addition products. After purification, 1,2,3-tri-(t-butoxycarbonylethyl)glycerol 6 was obtained with only 12% yield.…”

Section: Study Of the Reactivity Of Glycerol And Alcohols To Acrylatesmentioning

confidence: 99%

“…3-[2-Hydroxy-1-(hydroxymethyl)ethoxy]-propanenitrile (11b). GC-MS (EI, 70 eV): t R = 13.40 min, m/z (%): 114 (12), 97 (25), 86 (30), 73 (10), 54(100), 43(55), 31(40).…”

Section: Identification Of Productsmentioning

confidence: 99%

“…22 Moreover, very few examples of the nucleophilic addition of polyol to acrylic derivatives are presented: tetraalkylation of pentaerythritol was accomplished using AN in the presence of NaOH 23 or KOH 24 as a catalyst, or more recently using t-butyl acrylate with a phase transfer catalyst. 25 To our knowledge, only two publications focus on the addition of glycerol to acrylic derivatives: Bruson 26,27 in 1943 carried out the reaction between polyol and AN in the presence of 2-4% sodium methylate or 5-7% by weight of aqueous 40% potassium hydroxide solution to yield after 6-18 h 70-95% of polycyanoethylation products (74% of tricyanoethylglycerol TCEG was obtained after HCl neutralization and ethylene dichloride extraction 27 ). More recently, Trinadh et al 28 used Amberlyst A21 resin as a catalyst and TCEG was obtained with 8% yield.…”

Section: Introductionmentioning

confidence: 99%

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