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Nitration of aromatic compounds

A technology of aromatic compounds and nitrating agents, applied in the field of nitration of aromatic compounds, can solve problems such as not easy to contain, easy to explode, and harmful to the environment, and achieve the effects of easy packing, high yield and selectivity

Inactive Publication Date: 2009-05-06
CYTEC CANADA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chlorinated organic solvents are also used in these processes, such as methylene chloride, which are not easy to contain and are harmful to the environment if they leak
Not to mention that many of the nitrating agents used in these processes, such as alkyl or acyl nitrates, are explosive

Method used

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  • Nitration of aromatic compounds
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  • Nitration of aromatic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Nitration of Benzene in Bis(trifluoromethanesulfonamide)trihexyl(tetradecyl)phosphonium

[0054] Put 2.0g of bis(trifluoromethanesulfonamide)trihexyl(tetradecyl)phosphonium and 1.56g of benzene into a 50ml round bottom flask, then slowly add 1.50g of 100% nitric acid for more than 5 minutes. The contents of the flask were then heated at 80°C for 2 hours.

[0055] After 2 hours of reaction at 80°C, the contents of the flask were worked up in the usual manner. Then by weighing, gas chromatography and nuclear magnetic resonance analysis, it is known that quantitative nitrobenzene is basically generated.

Embodiment 2

[0056] Example 2 Nitration of various aromatic compounds in bis(trifluoromethanesulfonate)trihexyl(tetradecyl)phosphonium at a temperature of 80°C

[0057] The following aromatic compounds were nitrated essentially as described in Example 2: benzene, toluene, o-xylene, m-xylene, p-xylene and naphthalene. The aromatic compound to be nitrated is dissolved in trihexyl(tetradecyl)phosphonium bis(trifluoromethanesulfonate), and fuming nitric acid is added. The equivalent ratio of aromatic compounds to nitric acid is 1:1.2. The contents of the flask are then heated at 80°C for up to 6 hours.

[0058] After 6 hours of reaction, the contents of each flask were processed and the product analyzed for conversion and product distribution. Product distribution was obtained by gas chromatography and NMR methods. See Table 1 for the analysis results. No polynitroaromatic compounds were detected in the reaction product.

[0059] Table 1

[0060]

Embodiment 3

[0061] Embodiment 3: (used as contrast)

[0062] In this comparative example without the use of the phosphorus ionic liquid solvent, nitric acid and toluene were reacted at a temperature of 80°C for one day. The results showed that the conversion of mononitrotoluene was only 48%.

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Abstract

Aromatic compounds are mononitrated by reaction with a nitrating agent, preferably nitric acid, in a phosphonium salt ionic liquid.

Description

Field of invention: [0001] The present invention relates to the nitration of aromatic compounds. Background of the invention: [0002] The nitration reaction of aromatic compounds is very important in industry, and the nitration products of aromatic compounds can be used as dyes, explosives, pharmaceuticals, spices, plastics and solvents. A mixture of nitric and sulfuric acids is used in the nitration process (hence the name "mixed acid method") with sulfuric acid as the catalyst. Unfortunately, this process produces large amounts of spent dilute sulfuric acid, and the disposal or recycling of this spent acid creates serious environmental concerns. Sulfuric acid is diluted by the water produced during the nitrification process, so recovery of sulfuric acid involves an energy and costly sulfuric acid reconcentration process. The mixed acid method also produces by-products such as nitrocresols and cyanides, the removal of which requires costly wastewater treatment technologi...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/06C07C205/12C07C205/36C07C205/37
CPCC07C205/12C07C205/37C07C205/06C07C201/08
Inventor A·拉马尼M·J·厄尔A·J·罗伯特森
Owner CYTEC CANADA
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