Solubility of 5-Nitro- and 3-Nitrosalicylic Acids in an Acetic Acid/Nitric Acid Mixture

Andreozzi, Roberto; Canterino, Marisa; Caprio, V.; Somma, Ilaria Di; Sanchirico, Roberto

doi:10.1021/je060281b

Cited by 6 publications

(8 citation statements)

References 4 publications

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“…The fluid was considered as an incompressible homogeneous liquid mixture. Precipitation of the product and reactant is avoided by employing acetic acid as a solvent in sufficient excess 26, 27. It is also assumed that the CO 2 generated in the decarboxylation reaction gets fully dissolved in the liquid phase.…”

Section: Model Descriptionmentioning

confidence: 99%

Evaluation of Multipoint Dosing Strategy in a Miniaturized Tubular Reactor: Nitration of Salicylic Acid

2014

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A 2D non-isothermal reaction engineering model for a tubular reactor was developed for a complex reaction network of salicylic acid nitration. The influence of different operating and design parameters was studied to minimize the amount of secondary nitration products and limit the maximum temperature inside the reactor. Critical temperature effects were observed for larger reaction tubes, whereas close to isothermal conditions were perceived in smaller tubes. With single-point dosing of both reactants, complete conversion can be achieved but formation of secondary nitration products cannot be avoided. For a given number of dosing points, a suitable combination of the operating parameters allowed to achieve complete conversion and better yield of the desired product.

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Section: Model Descriptionmentioning

confidence: 99%

Evaluation of Multipoint Dosing Strategy in a Miniaturized Tubular Reactor: Nitration of Salicylic Acid

2014

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“…It is worthwhile stressing that the availability of a reliable model may be of great help in the prevention of the occurrence of hazardous events such as runaway phenomena. This upgrading is done by inserting in the model the solubility correlations, for 5-nitro and 3-nitrosalicylic acid, upon temperature and nitric acid concentrations [6] and choosing a proper regime of "dissolution with reaction". The resulting model may in principle account for the successive nitration of the two mononitroderivatives even when they are present as solids suspended in the reacting medium.…”

Section: -Nitrosalicylic Acid Is An Important Intermediate For the Pmentioning

confidence: 99%

“…in which the values for the parameters, obtained in a previous investigation [6], are reported in Table 5.…”

Section: Upgraded Modelmentioning

confidence: 99%

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Batch salicylic acid nitration by nitric acid/acetic acid mixture under isothermal, isoperibolic and adiabatic conditions

Andreozzi

Canterino

Caprio

et al. 2006

Journal of Hazardous Materials

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“…It is unfortunate that 3nitrosalicylic acid solubility in different solvent systems has not yet been systemically studied. The solubility of 3-nitrosalicylic acid only in an acetic acid/nitric acid mixture 13 and in water 14 has been reported until now.…”

Section: ■ Introductionmentioning

confidence: 99%

Equilibrium Solubility and Solvent Effect Study of 3-Nitrosalicylic Acid in Different Monosolvents Covering Temperatures from 278.15 to 323.15 K

2021

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The measurement of equilibrium solubility for 3-nitrosalicylic acid in 13 monosolvents such as methanol, N,N-dimethylformamide (DMF), isobutanol, ethanol, ethylene glycol (EG), N-methyl-2-pyrrolidinone (NMP), n-propanol, ethyl acetate, isopropanol, water, n-butanol, acetonitrile, and 1,4-dioxane was made by the saturation shake-flask technique covering temperatures from 278.15 to 323.15 K under p = 101.2 kPa. As the studied temperature increased, the mole fraction solubility of 3-nitrosalicylic acid increased and had a decreasing tendency in the following order: NMP > DMF > ethyl acetate > methanol > ethanol > n-propanol > acetonitrile > isopropanol > n-butanol > EG > isobutanol > 1,4-dioxane > water. The solvent effects, such as solvent–solute and solvent–solvent molecular interactions, were further examined by the linear solvation energy relationships. Then, the equilibrium solubility magnitudes were correlated with thermodynamic models and semiempirical equations, namely, Wilson, Apelblat, λh, and NRTL. The calculated maximum value of root-mean-square deviation was 182.0 × 10–4, and the maximum value of relative average deviation was 7.24 × 10–2. In general, the obtained relative average deviation values with the Apelblat equation were smaller than those with the other equation/models for a fixed monosolvent. Finally, the mixing solution properties, activity coefficient, and partial molar excess enthalpy at infinite dilution were determined with the help of the Wilson equation.

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Solubility of 5-Nitro- and 3-Nitrosalicylic Acids in an Acetic Acid/Nitric Acid Mixture

Cited by 6 publications

References 4 publications

Evaluation of Multipoint Dosing Strategy in a Miniaturized Tubular Reactor: Nitration of Salicylic Acid

Evaluation of Multipoint Dosing Strategy in a Miniaturized Tubular Reactor: Nitration of Salicylic Acid

Batch salicylic acid nitration by nitric acid/acetic acid mixture under isothermal, isoperibolic and adiabatic conditions

Equilibrium Solubility and Solvent Effect Study of 3-Nitrosalicylic Acid in Different Monosolvents Covering Temperatures from 278.15 to 323.15 K

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