Related Experiment Video
Updated: Jan 1, 2026
12:55
Millifluidics for Chemical Synthesis and Time-resolved Mechanistic Studies
Published on: November 27, 2013
11.6K
Hydrolysis data for bis(4-cyanophenyl) phenyl phosphate including rate constants and activation parameters
V E Terekhov1, V V Aleshkevich1, E S Afanaseva1
1Lomonosov Moscow State University, Department of Chemistry, 119991, Leninskie Gory, 1-3, Moscow, Russia.
Data in Brief
|December 25, 2019
Summary
This study details the hydrolysis of Bis(4-cyanophenyl) phenyl phosphate (CPP) under varying pH and temperature conditions. Hydrolysis rate constants and activation parameters were determined, providing key data for its application as a reactive diluent.
Area of Science:
- Organic Chemistry
- Polymer Science
Background:
- Bis(4-cyanophenyl) phenyl phosphate (CPP) is utilized as a reactive diluent in phthalonitrile monomer systems.
- Understanding the hydrolysis behavior of CPP is crucial for predicting its stability and performance in various applications.
Purpose of the Study:
- To investigate the hydrolysis kinetics of CPP under different pH conditions (4, 7, and 10).
- To determine the influence of temperature on CPP hydrolysis rates.
- To calculate activation parameters for the hydrolysis reaction.
Main Methods:
- High-Performance Liquid Chromatography (HPLC) was employed to monitor the conversion of CPP over time.
- Nuclear Magnetic Resonance (NMR) spectroscopy was used to identify the substrate and reaction products.
- Pseudo-first order rate constants were determined at 25, 50, and 80 °C.
- The Arrhenius equation was applied to calculate activation parameters.
Main Results:
- Hydrolysis rate constants for CPP were successfully determined at pH 4, 7, and 10 across a temperature range of 25-80 °C.
- Typical chromatograms and NMR spectra confirmed the reaction pathway and product formation.
- Activation parameters were calculated, offering insights into the reaction mechanism.
Conclusions:
- The hydrolysis of CPP is dependent on pH and temperature.
- The kinetic data and activation parameters provide a quantitative understanding of CPP stability.
- This research supports the effective utilization of CPP in phthalonitrile-based materials.
Related Concept Videos
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
3.8K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.8K
02:36Acidity and Basicity of Alcohols and Phenols
21.8K
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
21.8K
02:14SN2 Reaction: Kinetics
10.0K
Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
10.0K
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
7.2K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.2K
01:27Benzene to Phenol via Cumene: Hock Process
4.0K
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
4.0K
02:34Arrhenius Plots
46.3K
The Arrhenius equation relates the activation energy and the rate constant, k, for chemical reactions. In the Arrhenius equation, k = Ae−Ea/RT, R is the ideal gas constant, which has a value of 8.314 J/mol·K, T is the temperature on the kelvin scale, Ea is the activation energy in J/mole, e is the constant 2.7183, and A is a constant called the frequency factor, which is related to the frequency of collisions and the orientation of the reacting molecules.
The Arrhenius equation can be used...
The Arrhenius equation can be used...
46.3K