Runaway Reaction During Production of an Azo Dye Intermediate

Partington, Steven M.; Waldram, S.P.

doi:10.1205/095758202753502398

Cited by 29 publications

(10 citation statements)

References 2 publications

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“…The case study presented here is based on published information about a runaway reaction incident 7. The process to be discussed involved the diazotization of an aromatic amine, followed by decomposition of the diazonium compound to produce a phenol.…”

Section: Case Studymentioning

confidence: 99%

Generating innovative process designs using limited data

Sharratt

Wall

Borland

2003

J of Chemical Tech & Biotech

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Key constraints in process innovation are the time and cost spent obtaining data to identify and verify novel processes. Businesses are under increasing pressure to deliver products in shorter times; pressure which restricts and often prevents access to innovative and intensive processing options. The Britest project has identified key decisions in process design and the associated minimum data requirements. These involve identification and manipulation of the relevant rate processes and consideration of the phases of matter that are (or could be) present. By use of qualitative and semiquantitative reasoning it is possible to produce a range of possible process options very early in design. This is particularly useful in the low-tonnage chemicals sectors (fine and effect chemicals) where process design is primarily an empirical activity. It also helps to deal rationally with the complex chemistry prevalent in those industries. The early identification of options allows timely development of experimental programmes to evaluate the options. An illustrative example based on a diazotisation and the associated decomposition reaction is presented.

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Section: Case Studymentioning

confidence: 99%

Generating innovative process designs using limited data

Sharratt

Wall

Borland

2003

J of Chemical Tech & Biotech

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“…2 For example, in 1996, an explosion accident occurred in Holliday Company, which was engaged in dye production. 3 This accident was triggered by the decomposition of diazonium compounds. Diazotization reactions are commonly strongly exothermic, 4,5 and the reaction temperature is generally controlled at about 0−5 °C to inhibit the decomposition of DS.…”

Section: Introductionmentioning

confidence: 99%

“…However, DS may be violently decomposed due to the influence of external forces like heat and friction and cause serious explosions . For example, in 1996, an explosion accident occurred in Holliday Company, which was engaged in dye production . This accident was triggered by the decomposition of diazonium compounds.…”

Section: Introductionmentioning

confidence: 99%

Green and Low-Cost Synthesis of Thermally Stable Cation-Exchange Resin-Supported Diazonium Salt: An Example of Weakly Basic p-Nitroaniline Diazotization

Liu,

Feng,

Yan

et al. 2023

Org. Process Res. Dev.

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Wide applications of diazonium salts (DS) are limited due to their nature of poor thermal stability and explosive hazards. In this work, strong acid cation-exchange resin (Amberlyst-15), as an acid and anion provider, was used to synthesize the corresponding diazonium salt of weakly basic p-nitroaniline (p-NA). The thermal stability of raw materials (p-nitroaniline, Amberlyst 15) and cation-exchange resin-supported DS (CER-supported DS) was characterized by DSC and ARC, respectively. The synthesis conditions were optimized, and the exothermicity of the diazotization reaction was characterized by reaction calorimetry. Diazonium salts of p-NA were demonstrated to be obtained and chemisorbed on the cation-exchange resin surface. The optimal yield of CERsupported DS reached up to 80%. The initial decomposition temperature and decomposition energy of the CER-supported DS were about 55 °C and 183 J/g, respectively. The decomposition process of the CER-supported DS followed a single n-order reaction model, and the main decomposition product was p-nitrophenol. The merits of this synthesis method include being free of environmentally harmful inorganic acids and high-cost of tert-butyl nitrites and having good storage stability.

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“…Looking at the diazotization reaction, instances of decomposition of diazonium salts subsequently causing explosions [27] have been reported. This clearly indicates the adverse effect of this reaction in industry and justifies the need for the generation and in-situ use of these compounds so as to avoid their isolation.…”

Section: Introductionmentioning

confidence: 99%

A Facile Optimization of Diazotization and Phase Transfer Catalyzed Azo-Coupling Reactions in Microreactors

Akwi¹,

Bosma²,

Watts³

2016

J Flow Chem

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Herein, we illustrate how microreactor technology can be used as a tool for reaction screening and optimization, in addition to improving the reaction chemistry. We report the in-situ generation of azo compounds by reactive quenching of diazonium intermediates in microreactors. This involves an electrophilic aromatic substitution reaction, namely, an azo-coupling reaction performed in continuous-flow systems in the presence of a phase transfer catalyst with great emphasis on compounds that do not easily couple. Capitalizing on the benefits of a large surface area and the short molecular diffusion distances observed in microreactors, in-situ phase transfer catalyzed azo-coupling reaction of diphenylamine to p-nitroaniline was investigated. A rapid and easy optimization protocol was established which yielded a 99%, 22%, and 33% conversion of diphenylamine, carbazole, and triphenylamine, respectively, in approximately 2.4 min.

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Runaway Reaction During Production of an Azo Dye Intermediate

Cited by 29 publications

References 2 publications

Generating innovative process designs using limited data

Generating innovative process designs using limited data

Green and Low-Cost Synthesis of Thermally Stable Cation-Exchange Resin-Supported Diazonium Salt: An Example of Weakly Basic p-Nitroaniline Diazotization

A Facile Optimization of Diazotization and Phase Transfer Catalyzed Azo-Coupling Reactions in Microreactors

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