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Tecnología segura y eficiente de nitración de compuestos aromáticos

Resumen

Tipo:
Oferta Tecnológica
Referencia:
TOSI20160629001
Publicado:
06/07/2016
Caducidad:
06/07/2017
Resumen:
Un instituto de investigación esloveno ha desarrollado un método de nitración de compuestos aromáticos que se emplea para producir compuestos aromáticos nitrados con ácido nítrico acuoso sin utilizar ácido sulfúrico concentrado. Se trata de un proceso más seguro, selectivo y respetuoso con el medioambiente. El proceso se vende como secreto industrial. El instituto busca socios industriales, principalmente en el sector químico, interesados en licenciar la tecnología.

Details

Tittle:
Safe and efficient nitration of aromatic compounds
Summary:
A Slovenian research institute has developed a method for nitration of aromatic compounds. The method can be used to produce nitrated aromatic compounds with aqueous nitric acid without the use of concentrated sulphuric acid, making the process safer, more selective and environmentally friendly. The procedure is marketed as secret know-how. The institute is looking for business partners, primarily in chemical industry, interested in licensing the technology.
Description:
Nitration is a chemical process introducting nitro groups into organic compounds, including aromatic compounds, yielding nitroaromatic compounds such as nitrobenzene. Nitration reactions are notably used for the production of explosives, but they are of wide importance as chemical intermediates and precursors as well. Millions of tons of nitroaromatics are produced annually. Traditionally, nitration is performed with nitric acid in concentrated sulphuric acid, and research is driven towards the use of alternative reaction media or reagents (such as acids or ionic liquids), as well as new catalytic processes and catalysts (such as alumosilicates).

In the presented technology, aromatic compounds such as benzene and its derivatives may be nitrated with medium activation of the aromatic ring, at room temperature. For example, 1,3-dimethylbenzene may be nitrated to 2,4-dimethyl-nitrobenzene. Likewise, naphthalene may be nitrated to 1-nitronaphthalene. Other compounds suitable for nitration include, but are not limited to, benzene, iodobenzene, toluene, bromotoluene, butyltoluene, xylene, mesitylene, durene, butylbenzene, anisole, butylanisole, butylphenol, butylaniline, and dimethoxybenzene.

The presented technology solves the problem with a nitration process with nitric acid that does not depend on sulphuric acid, with equal or improved yields, efficiency, and regioselectivity of nitration and suppressed additional nitration. Reactions are conducted in such a way that use of strong secondary acid is avoided. Details of the procedure are part of the institute´s know-how.

Industrial partners are sought to license in the technology. License agreements will enable the researchers to maintain their focus on the research behind the technology whereas up-scaling to industrial level will be carried out in the industrial partner´s setting.

The researchers from a leading Slovenian research institute are among the leading scientists in their respective departments, and regulary publish in high-impact scientific journals. They are experts in halogenation and oxidation reactions with the emphasis on green "chemistry".


Advantages and Innovations:
Innovation.
In existing procedures, reactive species frequently used for nitration are nitronium ions. Secondary strong acids such as concentrated sulphuric acid are used to promote the formation of nitronium ions in reaction mass. The formation of the nitronium ion is accelerated by raising the concentration or amount of sulphuric acid, and the addition of hygroscopic substances for water removal. Reactions are conducted by addition of substrate to sulphuric acid and further addition of a mixture of nitric and sulphuric acid. Occurring exothermic reactions lead to local surplus of heat, resulting in side reactions. Such processes also result in vast amounts of nitrogen oxides and waste acids known to be harmful for the environment, and regeneration of sulphuric acid is energetically demanding as it includes vacuum vaporization and oxidation of organic compounds followed by concentration of sulphuric acid at high temperatures with application of the nitric acid for discolouration.
The presented technology solves this problem with a nitration process with nitric acid that does not depend on sulphuric acid, with equal or improved yields, efficiency, and regioselectivity of nitration and suppressed additional nitration. Reactions are conducted in such a way that use of strong secondary acid is avoided. Details of the procedure are part of the institute´s know-how.

Advantages.
In the presented technology, the solvent employed may easily be regenerated by distillation at lower pressure and reused in further processes. Waste side products of the nitration process are minimized. There are thus benefits with regard to energy demands, as production costs and the impact on the environment are reduced. Elimination of strong secondary acids (i.e. sulphuric acid) makes the process more user-friendly, wider range of substrates can be used and it eliminates harmful waste products.
Stage of Development:
Available for demonstration
IPs:
Secret Know-how

Partner sought

Type and Role of Partner Sought:
Chemical, pharmaceutical and agrochemical industry

The institute is looking for business partners, primarily in chemical industry, with the capacity for testing and optimization, interested in licensing the technology and upscaling production to industrial levels

Client

Type and Size of Client:
R&D Institution
Already Engaged in Trans-National Cooperation:
Si
Languages Spoken:
English
Slovenian

Keywords

Technology Keywords:
03004001 Agro chemicals
02007004 Colorantes y barnices
02007006 Fine Chemicals, Dyes and Inks
03004006 Organic Substances
03004010 Special chemicals, intermediates