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A convenient approach to arenediazonium tosylates
ID Mihelač, Mateja (Author), ID Siljanovska, Ana (Author), ID Košmrlj, Janez (Author)

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Abstract
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 This link opens in a new window
UDC:54-304.4
ISSN on article:0143-7208
DOI:10.1016/j.dyepig.2020.108726 This link opens in a new window
COBISS.SI-ID:26340867 This link opens in a new window
Publication date in RUL:12.03.2021
Views:962
Downloads:264
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Record is a part of a journal

Title:Dyes and pigments
Shortened title:Dyes pigm.
Publisher:Elsevier
ISSN:0143-7208
COBISS.SI-ID:25357056 This link opens in a new window

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

Projects

Funder:ARRS - Slovenian Research Agency
Project number:P1-0230
Name:Organska kemija: sinteza, struktura in aplikacija

Funder:ARRS - Slovenian Research Agency
Project number:J1-8147
Name:Ligandi s tzNHC strukturo v organokovinski kemiji in homogeni katalizi: tvorba vezi C-C in C-N v vodi

Funder:ARRS - Slovenian Research Agency
Project number:J1-9166
Name:Redefinicija in razširitev uporabe Sonogashirove reakcije pripajanja brez bakra

Funder:Other - Other funder or multiple funders
Funding programme:Ministry of Education, Science and Sport, Republic of Slovenia
Name:PhD Scholarship

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