Synthesis of 4-Chloro-3-nitrobenzotrifluoride: Industrial thermal runaway simulation due to cooling system failure

Copelli, Sabrina; Derudi, Marco; Cattaneo, Carlo Sala; Nano, Giuseppe; Raboni, Massimo; Torretta, Vincenzo; Rota, Renato

doi:10.1016/j.psep.2013.11.006

Cited by 37 publications

(21 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Finally, because of the huge amount of heat released when the reaction mass (mainly consisting of concentrated sulfuric acid) is diluted with water, an inert cooling fluid e.g. of the paraffinic type should be employed instead of water, in order to prevent dangerous incidental scenarios arising from a cooling fluid leakage into the reactor, which would cause an overheating of the reaction mass and a further triggering of the thermal runaway 27 .…”

Section: Reaction Systemmentioning

confidence: 99%

Kinetic-Free Safe Optimization of a Semibatch Runaway Reaction: Nitration of 4-Chloro Benzotrifluoride

Maestri

Rota

2016

Ind. Eng. Chem. Res.

Self Cite

View full text Add to dashboard Cite

In this work the general Ψ number criterion for the safe operation of semibatch runaway reactions has been applied to the optimization of a nitration process of primary importance in the agrochemical industry, that is the nitration through mixed acids of 4-chloro benzotrifluoride to produce a widely employed class of fluorinated herbicides. Such a reaction, as almost all the organic nitrations, belongs to the most critical class of exothermic reaction processes, for which the maximum temperature of the synthesis reaction under adiabatic conditions overcomes the decomposition temperature of the system, without any tempering effect due to a solvent evaporation. It has been verified that higher productivity operating conditions can be easily implemented through the general Ψ number criterion, even without a kinetic characterization of the system, but just elaborating information already available at the laboratory scale, where the chemical recipe is developed. The results obtained have been further validated through the boundary and temperature diagrams criterion, which however requires a previous estimation of the reaction kinetic parameters, with a much higher experimental effort.

show abstract

Section: Reaction Systemmentioning

confidence: 99%

Kinetic-Free Safe Optimization of a Semibatch Runaway Reaction: Nitration of 4-Chloro Benzotrifluoride

Maestri

Rota

2016

Ind. Eng. Chem. Res.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Nitro derivatives are well known to have a limited thermal stability with temperature 19,20 . Moreover the final nitration mixture with mixed acids is known to decompose through the transient generation of highly unstable sulfonated intermediates of the nitro compound, produced through its reaction with the sulfuric acid excess 21 .…”

Section: Reaction System Characterizationmentioning

confidence: 99%

Simple Monitoring of Fine Chemical Runaway Reactions in Multipurpose Plants: Nitration of 2,4-Dichloro Benzotrifluoride

Maestri

Curti

Rota

2018

Ind. Eng. Chem. Res.

Self Cite

View full text Add to dashboard Cite

In the fine chemical industry new production processes are often implemented in multipurpose existing plants with minimum adaptation investments. When the new process involves a potential runaway reaction, a full thermodynamic and kinetic characterization of the system should be performed to evaluate whether the reaction can be safely scaled-up in the selected plant. However, a detailed kinetic characterization is often unsuited because of the huge development rate of new products. In this work a potential runaway reaction of the agrochemical industry, that is, the nitration of 2,4-dichloro benzotrifluoride through mixed acids, is investigated with the aim of implementing it with a minimum experimental effort in an existing plant already dedicated to a similar reaction, that is, the nitration of 4-chloro benzotrifluoride. It has been shown that, even performing very similar reactions, the Ψ number criterion cannot be implemented in a univocal way to monitor the multipurpose SBR operation. Such a goal can instead be reached through the general procedure based on the Ψ, X and MTSRad set of process indicators, which was previously applied to the monitoring of polymerization processes.

show abstract

“…All information related to both the desired reaction and decomposition kinetics can be found in literature (Copelli et al 2011, 2013d, Maestri et al 2009b. In particular, the microkinetic parameters of reaction (1) are: A 1 = 3.228 × 10 12 m 3 s/kmol and E att,1 = 87260 kJ/kmol, respectively.…”

Section: Reacting Systemmentioning

confidence: 99%

“…In this work, a previously validated model (Copelli et al 2013d) has been suitably modiefied and used to simulate a dosing error in an industrial isoperibolic SBR (9 m 3 ) where the nitration of 4-Chlorobenzotrifluoride (4-Cl BTF) to 4-Chloro-3-nitrobenzotrifluoride (4-Cl-3-nitroBTF-a chemical intermediate) by the means of mixed acids is carried out. Its implementation has been realized using MATLAB ® .…”

Section: Introductionmentioning

confidence: 99%

Case study of tank explosion caused by wastewater without flash point

Copelli¹,

Torretta²,

Derudi³

et al. 2013

Safety, Reliability and Risk Analysis

View full text Add to dashboard Cite

In fine chemical industries, potentially runaway reactions are often carried out in semibatch reactors to better control the heat evolution. For such processes, an uncontrolled temperature increase can trigger secondary undesired reactions or, worse, decompositions of the reacting mixture with consequent reactor pressurization and, eventually, physical explosion. For this reason, during years, it has been tried to simulate how a runaway phenomenon evolves as a consequence of a number of upset operating conditions: e.g. dosing errors, cooling system failure or external fire. In this work, a dedicated software has been developed and used to simulate a dosing error occurring during an industrial synthesis. Particularly, it has been analyzed the effect of the different industrial temperature control modes (isoperibolic and isothermal) and their related controller parameters onto the time evolution of the main process variables. Theoretical simulations have shown that different scenarios can arise as a function of these control features.

show abstract

Synthesis of 4-Chloro-3-nitrobenzotrifluoride: Industrial thermal runaway simulation due to cooling system failure

Cited by 37 publications

References 27 publications

Kinetic-Free Safe Optimization of a Semibatch Runaway Reaction: Nitration of 4-Chloro Benzotrifluoride

Kinetic-Free Safe Optimization of a Semibatch Runaway Reaction: Nitration of 4-Chloro Benzotrifluoride

Simple Monitoring of Fine Chemical Runaway Reactions in Multipurpose Plants: Nitration of 2,4-Dichloro Benzotrifluoride

Case study of tank explosion caused by wastewater without flash point

Contact Info

Product

Resources

About