Nitration of Aromatic Compounds by Zn(NO3)2 · 2N2O4and Its Charcoal‐Supported System

Iranpoor, Nasser; Firouzabadi, Habib; Heydari, R.; Shiri, Morteza

doi:10.1081/scc-200048450

Cited by 23 publications

(6 citation statements)

References 28 publications

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“…More recently (post-2002) work has been reported using scarce or otherwise unsatisfactory reagents either homogeneously (eg. TFAA [38], zinc nitrate-N 2 O 4 [39] or ionic liquids [40]) or heterogeneously (ammonium nitrate-perchloric acid on montmorillonite clay [41], nitric acid-P 2 O 5 on silica gel [42] or tetramethylammonium nitrate-sulfuric acid on silica gel [43]) or required the used of microreactors [44]. Unfortunately, none of these systems is well suited to scale-up.…”

Section: Toluene Nitration -Initial Stagesmentioning

confidence: 99%

Annual Industrial Capabilities Report to Congress

Farnborough¹

2008

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The US Department of Defense requires an environmentally benign synthesis route for the manufacture of military grade trinitrotoluene (TNT) which eliminates the production of redwater arising from the sulfiting process for removing unsymmetrical trinitrotoluene isomers. QinetiQ has found that by using a novel nitrating system, N2O5 in dichloromethane, the proportion of meta-substituted nitrotoluenes can be reduced to 1.3-1.5%, instead of the 4-5% levels in current processes. Additional improvements have been made to the following di-and tri-nitration steps by using alternatives to traditional mixed (sulfuric-nitric) acid systems, namely 100% nitric acid and N2O5-sulfuric acid respectively, resulting in reduced emissions of pollutants (NOx offgas and tetranitromethane). As a result, TNT with a set point within 0.3 deg. C of the Mil. Spec. (80.2 deg. C) can be made by the QinetiQ process, without the need for sulfite washing; one recrystallization raises this figure to 80.6 deg. C. A study of the process economics has shown that the cost (at 4.5 million lb per annum scale) is not disproportionately greater than current processes.

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Section: Toluene Nitration -Initial Stagesmentioning

confidence: 99%

Annual Industrial Capabilities Report to Congress

Farnborough¹

2008

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“…Furthermore, nitrations are usually associated with heat which in turn may cause secondary reactions or decomposition of the final product which consequently leads to low purity and yields [16]- [19]. Moreover, redox sensitive compounds and acid-hydrolysable groups are not eligible under these conditions [20]- [24].…”

Section: Introductionmentioning

confidence: 99%

Zinc Chloride Catalyzed Regioselective Nitration of Aromatic Hydrocarbons Using Tetrachlorosilane-Sodium Nitrate Homogeneous System

Elmorsy

Shaaban²,

Eldesoky³

et al. 2015

IJOC

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The development of a new silane reagent derived from tetrachlorosilane (TCS) was applied in the present work. TCS-sodium nitrate (NaNO 3) binary reagent and zinc chloride (ZnCl 2) were reported here as a homogeneous nitrating system. The later was used for the efficient mono nitration, in most cases, with high para-regioselectivity. The nitration proceeded smoothly under mild condition, fairly clean and in good yields. This readily available and inexpensive system is superior to other methods by avoidance of the use of corrosive nitrating reagents and therefore considered to be convenient in terms of risk reduction, economic advantages and environment protection. The present protocol was convenient and applicable to a variety of aromatic hydrocarbons and could be amenable to high throughput synthesis of combinatorial libraries for potential drug development, which needs to be studied as part of future investigations.

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“…Apart from difficulties in handling the poisonous and corrosive dinitrogen tetroxide, a serious disadvantage of utilizing gaseous N 2 O 4 in organic reactions, for example, its high reactivity which usually causes undesired side reactions. In order to overcome the above mentioned limitations, some reports have been published on the use of N 2 O 4 complexes of organic [2], polymeric [3] and inorganic compounds [4] as useful reagents in organic reactions.…”

Section: Introductionmentioning

confidence: 99%

N2O4/SiO2 system as an efficient reagent for rapid and chemoselective conversion of trimethylsilyl ethers to the parent alcohols under nonaqueous conditions

Zolfigol

Mohammadpoor‐Baltork

Shiri

2008

JICS

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N 2 O 4 was easily impregnated on silica gel to give a stable heterogeneous reagent N 2 O 4 /SiO 2 (I). Chemoselective deprotection of trimethylsilyl ethers to the corresponding alcohols was achieved in the presence of I in CH 2 Cl 2 in excellent yields. The stability, easy preparation and high selectivity of the reagent make this method as a useful procedure for the selective deprotection of TMS ethers at room temperature.

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Nitration of Aromatic Compounds by Zn(NO₃)₂ · 2N₂O₄and Its Charcoal‐Supported System

Cited by 23 publications

References 28 publications

Annual Industrial Capabilities Report to Congress

Annual Industrial Capabilities Report to Congress

Zinc Chloride Catalyzed Regioselective Nitration of Aromatic Hydrocarbons Using Tetrachlorosilane-Sodium Nitrate Homogeneous System

N2O4/SiO2 system as an efficient reagent for rapid and chemoselective conversion of trimethylsilyl ethers to the parent alcohols under nonaqueous conditions

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