A convenient approach to arenediazonium tosylates

Mihelač, Mateja (author), Siljanovska, Ana (author), Košmrlj, Janez (author)

Herein we present a mild, simple and environmentally friendly diazotization protocol of aromatic and hetero-aromatic anilines into stable diazonium salts that surpass previously reported procedures. The reaction proceeds with tert-butyl nitrite in the presence of an equimolar amount or small excesses of p toluenesulfonic acid in ethyl acetate, at room temperature. o-Phenylenediamines yield benzotriazolium tosylates. The resulting diazonium tosylates proved to be bench stable over a long period of time. In selected examples, diazonium salts were let to react with activated aromatic compounds including 2-naphthol and aniline derivatives into the corresponding azo dyes.

• Language: English
• Keywords: diazotization, diazonium salts, azo compounds, p-toluenesulfonic acid
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2021
• Number of pages: 7 str.
• Numbering: Vol. 184, art. 108726
• PID: 20.500.12556/RUL-125379
• UDC: 54-304.4
• ISSN on article: 0143-7208
• DOI: 10.1016/j.dyepig.2020.108726
• COBISS.SI-ID: 26340867
• Publication date in RUL: 12.03.2021

Record is a part of a journal

• Title: Dyes and pigments
• Shortened title: Dyes pigm.
• Publisher: Elsevier
• ISSN: 0143-7208
• COBISS.SI-ID: 25357056

Licences

• License: CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
• Link: http://creativecommons.org/licenses/by-nc-nd/4.0/
• Description: The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.

Secondary language

• Language: Slovenian
• Keywords: diazotiranje, diazonijeve soli, azo spojine, p-toluensulfonska kislina