Alkaline hydrolysis of acrylic and methacrylic esters in 60% aqueous ethanol

Mallik, K. L.; Das, Moumita

doi:10.1007/bf00622580

Cited by 7 publications

(8 citation statements)

References 2 publications

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“…The hydrolysis rate measurements were carried out using an HPLC method at 20 °C. Also, the alkaline hydrolysis rate constant k 2 (second-order rate constant) for MA, EA, MMA and EMA at 30 °C was taken from Mallik and Das [ 2 ]. Furthermore, the second-order rate constant (k3) data for base-catalyzed acrylates (MA, EA, BA) and methacrylates (MMA) obtained using a diffusion method were taken from Sharma and Sharma [ 4 ].…”

Section: Methodsmentioning

confidence: 99%

“… a For abbreviations see the text; b Taken from Reference [ 11 ]; c Taken from Reference [ 20 ]; d Taken from Reference [ 6 ]; e Taken from Reference [ 2 ]. …”

Section: Figurementioning

confidence: 99%

“…Acrylate and methacrylate esters are more highly hydrolyzed with a base than with an acid [ 1 , 6 , 9 ], but their hydrolysis rate constants have been reported to be considerably small under alkaline conditions at 20 °C or 30 °C [ 1 – 4 , 6 ]. There are a few QSPRs for acid- or base-catalyzed ester hydrolysis of methacrylates [ 2 , 4 , 6 ], however the limited number of monomers have been chosen for QSARs study [ 1 – 4 , 6 ] because the hydrolysis rate for many hydrophobic homologous acrylate and methacrylate esters may be below the detection limit of assays. We previously reported that the glutathione (GSH) reactivity of acrylates and methacrylates was significantly related to their δC β , possibly due to the high reactivity of GS − with C β of these monomers [ 10 – 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…Mallik and Das [ 2 ] previously investigated the kinetics of alkaline hydrolysis for methyl and ethyl acrylates and their corresponding methacrylates, and revealed a possible relationship between the hydrolysis rate constants and the experimentally determined activation energy for these compounds. Also, Nakajima et al .…”

Section: Introductionmentioning

confidence: 99%

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Relationships Between Base-Catalyzed Hydrolysis Rates or Glutathione Reactivity for Acrylates and Methacrylates and Their NMR Spectra or Heat of Formation

Fujisawa

Kadoma

2012

IJMS

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The NMR chemical shift, i.e., the π-electron density of the double bond, of acrylates and methacrylates is related to the reactivity of their monomers. We investigated quantitative structure-property relationships (QSPRs) between the base-catalyzed hydrolysis rate constants (k1) or the rate constant with glutathione (GSH) (log kGSH) for acrylates and methacrylates and the 13C NMR chemical shifts of their α,β-unsaturated carbonyl groups (δCα and δCβ) or heat of formation (Hf) calculated by the semi-empirical MO method. Reported data for the independent variables were employed. A significant linear relationship between k1 and δCβ, but not δCα, was obtained for methacrylates (r2 = 0.93), but not for acrylates. Also, a significant relationship between k1 and Hf was obtained for both acrylates and methacrylates (r2 = 0.89). By contrast, log kGSH for acrylates and methacrylates was linearly related to their δCβ (r2 = 0.99), but not to Hf. These findings indicate that the 13C NMR chemical shifts and calculated Hf values for acrylates and methacrylates could be valuable for estimating the hydrolysis rate constants and GSH reactivity of these compounds. Also, these data for monomers may be an important tool for examining mechanisms of reactivity.

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Section: Methodsmentioning

confidence: 99%

“… a For abbreviations see the text; b Taken from Reference [ 11 ]; c Taken from Reference [ 20 ]; d Taken from Reference [ 6 ]; e Taken from Reference [ 2 ]. …”

Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Relationships Between Base-Catalyzed Hydrolysis Rates or Glutathione Reactivity for Acrylates and Methacrylates and Their NMR Spectra or Heat of Formation

Fujisawa

Kadoma

2012

IJMS

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“…Despite the relatively limited literature available, it is still widely accepted that methacrylate-based polymers are significantly more stable to hydrolysis than their acrylate-based equivalents. [26][27][28] Recently, Monteiro and co-workers carried out an in-depth study into the self-catalyzed hydrolysis of linear homopolymers of the amino-functionalized monomer, N,N′-(dimethylamino) ethyl acrylate (DMAEA). 29 The self-catalyzed nature of the hydrolysis, in which the rate of catalysis is further accelerated by the carboxylic acid by-product, forms poly(acrylic acid) and a small molecule of N,N′-dimethylaminoethanol.…”

Section: Introductionmentioning

confidence: 99%

The hydrolytic behavior of N,N′-(dimethylamino)ethyl acrylate-functionalized polymeric stars

2017

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Independent and Synergistic Modulations of Viscoelasticity and Stiffness of Dynamically Cross-Linked Cell-Encapsulating ClickGels by Covalently Tethered Polymer Brushes

Tan

Song

2021

Biomacromolecules

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We report independent and synergistic modulations of the stiffness and viscoelasticity of ClickGels, formed by a combination of the bio-orthogonal covalent and dynamic noncovalent cross-linking, by covalently incorporating nonionic, zwitterionic, or anionic polymer brushes. Tethering nonionic and zwitterionic brushes at the cost of noncovalent cross-linking increased stiffness and slowed stress relaxation, respectively, without altering the other properties. Meanwhile, tethering anionic brushes significantly increased ClickGel stiffness, while also slowing its stress relaxation. ClickGels with faster stress relaxation, not reduced stiffness, promoted short-term (24 h) viability and YAP/TAZ nuclear localization of encapsulated bone marrow-derived stromal cells (BMSCs). In contrast, ClickGel stiffness, not viscoelasticity, inversely correlated to the short-term dehydrogenase activity of encapsulated BMSCs. This work highlights the role of the ionic state of polymer brushes in modulating the hydrogel elastic modulus and viscoelasticity and establishes the brush-modified ClickGel as a facile and reproducible tool for manipulating mechanical cues of the synthetic cellular niche.

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Alkaline hydrolysis of acrylic and methacrylic esters in 60% aqueous ethanol

Cited by 7 publications

References 2 publications

Relationships Between Base-Catalyzed Hydrolysis Rates or Glutathione Reactivity for Acrylates and Methacrylates and Their NMR Spectra or Heat of Formation

Relationships Between Base-Catalyzed Hydrolysis Rates or Glutathione Reactivity for Acrylates and Methacrylates and Their NMR Spectra or Heat of Formation

The hydrolytic behavior of N,N′-(dimethylamino)ethyl acrylate-functionalized polymeric stars

Independent and Synergistic Modulations of Viscoelasticity and Stiffness of Dynamically Cross-Linked Cell-Encapsulating ClickGels by Covalently Tethered Polymer Brushes

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