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Process for preparing c.i. Pigment Red 179

A compound and polar technology, applied in the direction of naphthalene dicarboxamide dyes/phthalimide dyes, etc., can solve the problems of complex equipment, lengthy reaction steps, and many types of chemical raw materials

Active Publication Date: 2017-05-24
LIAONING LIANGANG PIGMENT & DYESTUFF CHEM +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The defects of this manufacturing process are: ①The alkali fusion reaction of 1,8-naphthalimide to generate 3,4,9,10-perylene tetracarboxylic acid diimide in molten KOH needs to be carried out at 250°C
②Because the alkali fusion reaction needs to be carried out at a higher temperature, side reactions will inevitably occur during the reaction, so the yield of 3,4,9,10-perylenetetracarboxylic acid diimide is less than 50 %
③ After 3,4,9,10-perylenetetracarboxylic acid diimide is oxidized and converted into perylene anhydride, its quality cannot meet the requirements for subsequent production of pigments, and it needs to be refined by "alkali dissolution-acid precipitation method". Therefore, a large amount of acid and alkali will be consumed at this stage
It can be seen that the traditional method for preparing 3,4,9,10-perylenetetracarboxylic acid diimide has defects such as lengthy reaction steps, complex equipment required for the reaction, many types of chemical raw materials consumed, and unfriendly to the environment.

Method used

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  • Process for preparing c.i. Pigment Red 179
  • Process for preparing c.i. Pigment Red 179
  • Process for preparing c.i. Pigment Red 179

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In a 500mL round bottom flask, add cesium hydroxide monohydrate (50.4g, 0.30mol), 1,8-diazabicycloundec-7-ene (76.0g, 0.50mol) and o-dichlorobenzene (180g ), under nitrogen protection, heated to 100°C under stirring, and then added N-methyl-1,8-naphthalimide (25.5g, 0.60mol) when the solid was completely dissolved. Thin-plate chromatography (TLC) tracked until the raw material point completely disappeared (about 12 hours), stopped heating, naturally cooled to room temperature, added methanol to dilute and then filtered, and the filter cake was washed with methanol until there was no o-dichlorobenzene smell. After drying, a dark red solid (21.5 g) was obtained, yield 80%.

[0034]Adopt TOF-SIMS mass spectrometer (ION-TOF GmbH company) to measure the mass spectrum data of this dark red solid and the attribution of each ion peak as follows: M=418, molecular ion peak; M=404, [M-14] - (M-CH 2 ); M=390, [M-28] - (M-2xCH 2 ); M=375, [M-43] - (M-2xCH 2 –O+H); M=345, [M-73...

Embodiment 2

[0036] Add cesium hydroxide monohydrate (67.2g, 0.40mol), 1,8-diazabicycloundec-7-ene (60.8g, 0.40mol) and 1,2,4- Trichlorobenzene (200g), under nitrogen protection, heated to 100°C under stirring, and then added N-methyl-1,8-naphthoimide (25.5g, 0.60mol) after the solid was completely dissolved. After adding, the temperature was raised to React at 190°C, follow TLC until the raw material point disappears (about 10 hours), stop heating, cool to room temperature naturally, add ethanol to dilute and filter, and wash the filter cake with ethanol until there is no 1,2,4-trichlorobenzene smell. After drying, a dark red solid (22.0 g) was obtained with a yield of 80%. The mass spectral data of the dark red solid measured by a TOF-SIMS mass spectrometer is the same as in Example 1.

Embodiment 3

[0037] Embodiment 3 (comparative example)

[0038] Refer to the literature The Journal of organic chemistry, 2001, 66(1):94-98. The method described in the preparation of N,N'-dimethyl-3,4,9,10-perylenetetracarboximide.

[0039] In a 100 mL round-bottomed flask, potassium tert-butoxide (8.08 g, 0.072 mol), 1,5-dioxabicyclo[4.3.0]non-5-ene (12.0 g, 0.096 mol) and diethylene glycol di Methyl ether (25mL), under the protection of nitrogen, heated to 130°C, when the solid was completely dissolved, add N-methyl-1,8-naphthoimide (5.08g, 0.12mol), after the addition, react for 3h, stop Heated, cooled to room temperature, diluted with DMF and filtered, and the filter cake was washed with DMF. After drying, a dark red solid (3.7 g) was obtained, yield 72%.

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Abstract

The invention relates to a method for preparing N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide (C.I. pigment red 179). A reaction is conducted on N-methyl-1,8-naphthalimide in a system composed of a mixed base composed of caesium hydroxide or hydrate thereof and DBU and polar aryl halide at 140 DEG C-190 DEG C, and N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide can be obtained. After pigment-based processing is conducted on N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide, the crystal form of N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide is the same as that of a C.I. pigment red 179 product.

Description

technical field [0001] The present invention relates to a kind of preparation method of the red organic pigment that is used for automobile paint, specifically, relate to a kind of preparation N,N'-dimethyl-3,4,9,10-perylenetetracarboximide ( C.I. Pigment Red 179) method. Background technique [0002] C.I. Pigment Red 179 (chemical composition is N,N'-dimethyl-3,4,9,10-perylenetetracarboximide) is the most widely used variety of perylene pigments, specially used in automotive paint modulation. [0003] The traditional method of preparing C.I. Pigment Red 179 is to first synthesize N,N'-dimethyl-3,4,9,10-perylenetetracarboximide, and then process it to obtain commercialized Organic pigments, among them, the manufacturing process of N,N'-dimethyl-3,4,9,10-perylenetetracarboximide is as follows: 1,8-naphthalimide is melted at 250℃ Alkali fusion reaction in KOH makes it into 3,4,9,10-perylenetetracarboxylic diimide, which is then converted into 3,4,9,10-perylenetetracarboxyli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/08
CPCC09B57/08
Inventor 沈永嘉邹盼盼张伟候嘉祺张志刚张顺
Owner LIAONING LIANGANG PIGMENT & DYESTUFF CHEM
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