Industrialized preparation method of 1,4,5,8-naphthalene tetracarboxylic acid

A technology of naphthalenetetracarboxylic acid and acylation, applied in 1 field, can solve the problems of many three wastes, long steps, low yield and the like

Inactive Publication Date: 2016-11-23
朱婧瑶
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the existing methods for preparing 1,4,5,8-naphthalene tetracarboxylic acid with long steps, low yield, severe reaction conditions and more wastes, the purpose of the present invent...

Method used

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  • Industrialized preparation method of 1,4,5,8-naphthalene tetracarboxylic acid
  • Industrialized preparation method of 1,4,5,8-naphthalene tetracarboxylic acid
  • Industrialized preparation method of 1,4,5,8-naphthalene tetracarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] step one:

[0020] To naphthalene (40 g, 0.31 mol) in carbon disulfide (2 L) was added AlCl in portions at 0 °C 3 (206.6g, 1.55mol), then warmed up to 10°C and stirred for 20min. Oxalyl chloride (78.7 g, 0.62 mol) was slowly added dropwise to the solution, and after the dropwise addition was completed, it was raised to room temperature and stirred for 6 h. The temperature was lowered to 0°C, 150mL of concentrated hydrochloric acid and 2L of chloroform were added to the reaction solution, and the organic phase was washed with water, washed with saturated brine, and dried to obtain compound 1 (63.7g), with a yield of 87%. Proton NMR spectrum (400MHz, DMSO-d 6 )δ: 8.28 (4H, s), Calcd for C 14 h 4 o 4 : 236.0110, Found: 236.0102.

[0021] Step two:

[0022] After a mixed solution of compound 1 (50 g, 0.21 mol), NaOH (33.6 g, 0.84 mol) in 1,4-dioxane (240 mL) and water (90 mL) was warmed to 60 ° C, slowly added dropwise H 2 o 2 (35.7 mL, 30%, 0.315 mol) was added dr...

Embodiment 2

[0024] step one:

[0025] To naphthalene (40 g, 0.31 mol) in carbon disulfide (2 L) was added AlBr in portions at 0 °C 3 (413.4g, 1.55mol), then warmed up to 10°C and stirred for 20min. Oxalyl bromide (133.8 g, 0.62 mol) was slowly added dropwise to the solution, and after the dropwise addition was completed, it was raised to room temperature and stirred for 6 h. The temperature was lowered to 0°C, 150mL of concentrated hydrochloric acid and 2L of chloroform were added to the reaction solution, the organic phase was washed with water, washed with saturated brine, and dried to obtain compound 1 (58.5g), with a yield of 80%. Proton NMR spectrum (400MHz, DMSO-d 6 )δ: 8.28 (4H, s), Calcd for C 14 h 4 o 4 : 236.0110, Found: 236.0102.

[0026] Step two:

[0027] After a mixed solution of compound 1 (50 g, 0.21 mol), NaOH (33.6 g, 0.84 mol) in 1,4-dioxane (240 mL) and water (90 mL) was warmed to 60 ° C, slowly added dropwise H 2 o 2 (35.7 mL, 30%, 0.315 mol) was added dropwi...

Embodiment 3

[0029] step one:

[0030] To naphthalene (40 g, 0.31 mol) in carbon disulfide (2 L) was added AlCl in portions at 0 °C 3 (206.6g, 1.55mol), then warmed up to 10°C and stirred for 20min. Oxalyl chloride (78.7 g, 0.62 mol) was slowly added dropwise to the solution, and after the dropwise addition was completed, it was raised to room temperature and stirred for 6 h. The temperature was lowered to 0°C, 150mL of concentrated hydrochloric acid and 2L of chloroform were added to the reaction solution, and the organic phase was washed with water, washed with saturated brine, and dried to obtain compound 1 (63.7g), with a yield of 87%. Proton NMR spectrum (400MHz, DMSO-d 6 )δ: 8.28 (4H, s), Calcd for C 14 h4 o 4 : 236.0110, Found: 236.0102.

[0031] Step two:

[0032] To a mixed solution of compound 1 (50 g, 0.21 mol), NaOH (33.6 g, 0.84 mol) in 1,4-dioxane (240 mL) and water (90 mL) was added m-chloroperoxybenzene in portions at room temperature After the addition of formic aci...

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PUM

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Abstract

The invention is an industrialized preparation method of 1,4,5,8-naphthalene tetracarboxylic acid. The invention uses cheap and easy-to-obtain naphthalene as a starting material, and undergoes Friedel-Crafts acylation reaction, Baeyer-Villiger oxidation-hydrolysis "one 1,4,5,8-naphthalene tetracarboxylic acid is obtained after the pot method "reaction. Wherein the Friedel-Crafts acylation reaction yield is 87%, the Baeyer-Villiger oxidation-hydrolysis yield is 91%, and the total reaction yield is 79%. The present invention emphasizes the characteristics of short steps, simple reaction, high yield, simple purification method, easy operation and the like from the chemical point of view.

Description

technical field [0001] The invention relates to a high-efficiency preparation method of 1,4,5,8-naphthalene tetracarboxylic acid, which belongs to the preparation technology of dye intermediates. Background technique [0002] Naphthalene tetracarboxylic acid is an important intermediate for the preparation of reduced brilliant orange GR, bordeaux 2R, dispersed brilliant yellow HRL, H7GL, orange HFFG, pigment orange and pigment red. Among them, the mixed dye formed after dehydration and ring closure of 1,4,5,8-naphthalene tetracarboxylic acid and o-phenylenediamine in glacial acetic acid is called vat red GG, which can be separated with ethanol solution of potassium hydroxide to obtain vat orange GR and Bordeaux 2R, both dyes have good fastnesses across the board. Brilliant orange is the brightest of the orange vat dyes, and it is an advanced vat dye. Pigment orange 43 obtained by pigmentation of brilliant orange is a high-grade pigment with excellent heat resistance, solve...

Claims

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Application Information

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IPC IPC(8): C07C51/087C07C63/40
CPCC07C51/087C07C45/46C07D493/06
Inventor 朱婧瑶
Owner 朱婧瑶
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