• Title, Summary, Keyword: Aromatic Nitration

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Nitration of Toluene with NO2-O3 (이산화질소-오존을 이용한 톨루엔의 니트로화 반응)

  • Cho, Jin-Ku;Kim, Young-Tae;Kim, Young Gyu;Lee, Yoon-Sik
    • Applied Chemistry for Engineering
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    • v.9 no.7
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    • pp.1085-1089
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    • 1998
  • The well-established nitric acid-sulfuric acid mixed acid process for the nitration of aromatic compounds has serious problems due to the large amount of waste acids and severe reaction conditions. Nitration of toluene can be conducted using nitrogen dioxide and ozone instead of mixed acid. We found that conc. nitric acid increased the reactivity as catalyst and the amount of nitrogen dioxide controlled the extent of nitration. Dinitration proceeded to more than 92 mole % conversion within 2 hr at $0^{\circ}C$ with 6 eq. of nitrogen dioxide and 2 eq./hr of ozone flow. Toluene completed mononitration within 30 min using 3 eq. of nitrogen dioxide, 3 eq. of nitric acid, and 1.5 eq./hr of ozone flow. As a clean process of aromatic nitration, this method is expected to replace the present process which causes the environmental problems.

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A Study on the Scale-up Test for the Nitration Process using NO2-O3 (이산화질소-오존을 이용한 니트로화 반응의 Scale-up 연구)

  • Cho, Jin-Ku;Kim, Young-Tae;Sung, Si-Young;Chung, Kyoo-Hyun;Lee, Bon-Su;Kim, Young Gyu;Lee, Yoon-Sik
    • Applied Chemistry for Engineering
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    • v.10 no.7
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    • pp.1092-1095
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    • 1999
  • The well-known mixed-acid process for the aromatic nitration requires subsequent separation of spent acid, mainly dilute sulfuric acid. A novel nitration process using $HNO_3-NO_2-O_3$ was tested in a small pilot scale with 3 mol of p-nitrotoluene. Nitrogen dioxide(14.3 mol) was added three times in parts into the solution of p-nitrotoluene and $HNO_3$(6 mol) in dichloroethane. The nitration proceeded to more than 97% conversion within 5.5 h using 0.871 mol/h of ozone. As a clean process of aromatic nitration, this method is expected to replace the present process which causes the environmental problems.

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Nitration of Chlorobenzenes with NO2-O3 (이산화질소-오존을 이용한 클로로벤젠들의 니트로화 반응)

  • Lee, Bon-Su;Chung, Kyoo-Hyun;Lee, Won-Heui;Kim, Young-Su;Kim, Tae-Hyoung
    • Applied Chemistry for Engineering
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    • v.7 no.3
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    • pp.530-535
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    • 1996
  • Nitrochlorobenezenes are used as intermediates for dyes, pharmaceuticals and perfumes. By far the most common industrial nitration process employs a mixture of nitric acid and sulfuric acid. Due to water formed in the reaction, the mixed acid nitration requires subsequent separation of spent acid, mainly dilute sulfuric acid. In the stream of ozone, nitrogen dioxide can be used as a nitrating agent for the nitration of chlorobenzene. With 6eq of $NO_2$ and 1.0eq/hr of ozone flow, the mononitration of chlorobenzene ended within 3hr at $0^{\circ}C$ while the dinitration of chlorobenzene did in 12hr. This method can be employed for the nitration of some aromatic compounds to reduce pollutants from the present mixed-acid process.

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Reusable and Efficient Polystryrene-supported Acidic Ionic Liquid Catalyst for Mononitration of Aromatic Compounds

  • Li, Li Xia;Ling, Qi Long;Liu, Zu Liang;Xing, Xiao Dong;Zhu, Xiao Qin;Meng, Xiao
    • Bulletin of the Korean Chemical Society
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    • v.33 no.10
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    • pp.3373-3377
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    • 2012
  • A series of polystyrene-supported 1-(propyl-3-sulfonate)-3-methyl-imidazolium hydrosulfate acidic ionic liquid (PS-$[SO_3H-PMIM][HSO_4]$) catalysts were prepared and tested for mononitration of simple aromatics compounds with nitric acid. It was found that the reactivity of the catalysts increased with increasing $[SO_3H-PMIM][HSO_4]$ content. The para-selectivity was not only related to the $[SO_3H-PMIM][HSO_4]$ content but also the substituent groups in aromatics. A reaction mechanism of nitration over this new catalyst was proposed. The catalytic activity of this catalyst decreased slightly after fifth runs in the synthesis of nitrotoluene.

Changes in Concentration Levels of Polycyclic Aromatic Compounds Associated with Airborne Particulate Matter in Downtown Tokyo after Introducing Government Diesel Vehicle Controls

  • Kojima, Yuki;Inazu, Koji;Hisamatsu, Yoshiharu;Okochi, Hiroshi;Baba, Toshihide;Nagoya, Toshio
    • Asian Journal of Atmospheric Environment
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    • v.4 no.1
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    • pp.1-8
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    • 2010
  • The effectiveness of the government regulation on tail-pipe emission for diesel vehicles issued in 2003 in Tokyo was evaluated in this study. Variations in annual average concentrations of polycyclic aromatic hydrocarbons (PAHs) and nitro-PAHs associated with airborne particulate matter were investigated in connection with the variation in airborne elemental carbon (EC) concentration in downtown Tokyo, Japan in 2006-2007 and in 1997-1998. The annual average concentrations of EC, seven different PAHs, and 1-nitropyrene were found to have decreased significantly from 1997-1998 to 2006-2007. The most prominent decrease in atmospheric concentration was observed for 1-nitropyrene, which is a representative nitro-PAH originating from diesel vehicles. This indicated that the government control has worked to considerably reduce both atmospheric mutagens and airborne particulate matter. In contrast, the concentrations of two nitro-PAHs, 2-nitrofluoranthene and 2-nitropyrene, remained the same. These nitro-PAHs are known to be formed by atmospheric nitration of their parent PAHs, and this result suggested factors other than the concentration of parent PAHs and $NO_2$ affects the degree of atmospheric formation of nitro-PAHs.