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Preparation of 4-nitro-1,8-naphthalic acid

A technology of naphthalene dicarboxylic acid and nitro, which is applied in the field of compound preparation, can solve problems such as environmental pollution and equipment corrosion, and achieve the effects of shortening reaction time, simple operation, and reducing production costs

Inactive Publication Date: 2008-12-17
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method seriously corrodes the equipment and pollutes the environment

Method used

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  • Preparation of 4-nitro-1,8-naphthalic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Add 1.542g (10mmol) acenaphthene, 40mL90% acetic acid (volume fraction), 0.223g (0.56mmol) polyethylene glycol-400, 13.710g (25mmol) cerium ammonium nitrate in the Erlenmeyer flask, install a reflux device, and heat to 30°C, reacted for 2.0 hours, wherein, TLC traced, the developer was acetone-petroleum ether (volume ratio 1:5), the reaction product was poured into ice water, a yellow precipitate was precipitated, filtered by suction, and the solid was washed 2-3 times with water. 30 mL each time, 3.901 g of crude product was obtained, which was recrystallized with 15 mL of 95% ethanol, and dried to obtain 4-nitro-1,8-naphthalene dicarboxylic acid. Weight: 2.060g, yield: 78.9%, mp: 151°C-153°C, literature value (140°C-150°C decomposition), IR: Vmax (KBr tablet, cm -1 ), 3127 (-OH), 1623 (C=O), 1595, 1508, 1400 (naphthalene ring skeleton vibration), 1508, 1325 (-NO 2 ), 818, 777 (=C-H), MS: m / z (M+H) + 260.9, 1 HNMR (DMSO-d 6 )δ: 8.60(s, 1H), 8.58(s, 1H), 7.48(d, 1H)...

Embodiment 2

[0014] Add 154.2g (1mol) acenaphthene, 0.5L90% acetic acid (volume fraction) in the reaction flask, 282.1g (0.705mol) polyethylene glycol-400, 1644.0g (3mol) cerium ammonium nitrate, heat to 50 ℃, react 1.6h, wherein TLC tracked, the developer was acetone-petroleum ether (volume ratio 1:5), the reaction product was poured into ice water to obtain a yellow precipitate, filtered by suction, and the solid was washed 2-3 times with 30mL each time to obtain crude The product was 388.4g. The crude product was recrystallized with 1L of 95% ethanol and dried to obtain 4-nitro-1,8-naphthalene dicarboxylic acid. Weight: 203.8g, yield: 78.1%, mp: 151°C-152.7°C, literature value (decomposition at 140°C-150°C), IR: Vmax (KBr tablet, cm -1 ), 3125 (-OH), 1628 (C=O), 1597, 1510, 1400 (naphthalene ring skeleton vibration), 1510, 1327 (-NO 2 ), 820, 779 (=C-H), MS: m / z (M+H) + 260.5, 1 HNMR (DMSO-d 6 )δ: 8.61(s, 1H), 8.58(s, 1H), 7.48(d, 1H), 8.52(d, 1H), 7.47(d, 1H), 7.76(m, 1H) 7.36(d, 1...

Embodiment 3

[0016] Add 154.2g (1mol) acenaphthene, 0.5L90% acetic acid (volume fraction) in the reaction flask, 282.1g (0.705mol) polyethylene glycol-400, 1644.0g (3mol) cerium ammonium nitrate, heat to 70 ℃, react 1.5h, wherein TLC tracked, the developer was acetone-petroleum ether (volume ratio 1:5), the reaction product was poured into ice water to obtain a yellow precipitate, filtered by suction, and the solid was washed 2-3 times with 30 mL each time to obtain crude The product was 388.4g. The crude product was recrystallized with 1L of 95% ethanol and dried to obtain 4-nitro-1,8-naphthalene dicarboxylic acid. Weight: 203.8g, yield: 78.1%, mp: 151°C-152.7°C, literature value (decomposition at 140°C-150°C), IR: Vmax (KBr tablet, cm -1 ), 3125 (-OH), 1628 (C=O), 1597, 1510, 1400 (naphthalene ring skeleton vibration), 1510, 1327 (-NO 2 ), 820, 779 (=C-H), MS: m / z (M+H) + 260.5, 1 HNMR (DMSO-d 6 )δ: 8.61(s, 1H), 8.58(s, 1H), 7.48(d, 1H), 8.52(d, 1H), 7.47(d, 1H), 7.76(m, 1H) 7.36(d, ...

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Abstract

The invention discloses a preparation method of 4-nitryl-1, 8-naphthalene bimethanoic acid. The preparation method of the invention selects ammonium ceric nitrate to react with acenaphthylene so as to obtain the 4-nitryl-1, 8-naphthalene bimethanoic acid, wherein, acetic acid is a solvent, polyethylene glycol-400 is a phase-transfer catalyst, the ammonium ceric nitrate is a nitrating agent and an oxidant, and the mole ratio of the acenaphthylene: the ammonium ceric nitrate: the polyethylene glycol-400 is 1: 1.0 to 3.0: 0.14 to 2.8. The preparation method of the invention, by selecting the ammonium ceric nitrate to react with the acenaphthylene to obtain the target product at one step, simplifies operation, shortens reaction time, eliminates pollution, saves energy and protects environment.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of 4-nitro-1,8-naphthalene dicarboxylic acid. Background technique [0002] 4-Nitro-1,8-naphthalene dicarboxylic acid is an organic synthesis intermediate, which can be used as an intermediate for acid bright yellow FF, disperse fluorescent yellow dyes, etc., and occupies an important position in the field of fine organic chemicals. At present, 4-nitro-1,8-naphthalenedicarboxylic acid is mainly obtained from acenaphthene as raw material, nitrated by nitric acid, and then oxidized by sodium dichromate. This method requires two steps to complete. This method seriously corrodes the equipment and pollutes the environment. It can also be obtained by oxidation of 5-nitroacenaphthene as a raw material through sodium dichromate oxidation. Contents of the invention [0003] The object of the present invention is to: provide the preparation method of 4-nitro-1...

Claims

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Application Information

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IPC IPC(8): C07C205/57C07C201/10
Inventor 朱惠琴周建峰朱凤霞孙小军
Owner HUAIYIN TEACHERS COLLEGE
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