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Preparation method of phthaloyl azo dye

A technology of phthalimide-based azo and dyes, which is applied in the preparation of phthalimide-based azo dyes, two asymmetric structure nitro compounds in the field of preparing azo dyes, can solve a large number of problems Inorganic salts, waste water, environmental impact and other issues, to achieve the effect of high safety, low energy consumption, and short synthesis process

Active Publication Date: 2013-01-16
ZHEJIANG WANFENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest disadvantage of preparing azo dyes with diazotization coupling reaction is that a large amount of nitrite is required to form diazonium salts, which will produce a large amount of inorganic salts and waste water, which have a great impact on the environment

Method used

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  • Preparation method of phthaloyl azo dye
  • Preparation method of phthaloyl azo dye
  • Preparation method of phthaloyl azo dye

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preparation example Construction

[0018] A method for preparing a phthalimide-based azo dye, comprising mixing a compound of formula (II) and a compound of formula (III) in equimolar proportions, adding them to a solvent containing alkali, and passing hydrogen gas in the presence of a catalyst , react at room temperature to 98°C for 4 to 24 hours under low pressure (0.1 to 0.2 MPa) or normal pressure to directly prepare the compound of formula (I) with azo structure.

[0019]

[0020] Among them, in formula (I), formula (II) and formula (III), n=1, 2 or 3; X is -H, -CH 3 、-C 2 h 5 , -Cl, -Br; Y is -H, -Cl, -Br; R 1 -H, -CH 3 , -NHCOCH 3 , -NHCOC 2 h 5 ; 2 -H, -CH 3 ; 3 with R 4 Same as -C 2 h 4 OCH 3 、-C 2 h 4 OC 2 h 5 、-C 2 h 4 OCOCH 3 、-C 2 h 4 OCOC 2 h 5 ;

[0021] The catalyst is one of Pt nanomaterials, Pd nanomaterials or a mixture of both.

[0022] The diameter of the catalyst is 2nm-3nm.

[0023] Preferably, the amount of the catalyst accounts for 0.01wt%-1wt% of the compo...

Embodiment 1

[0029] Synthesis of platinum nanowires: Platinum acetylacetonate was reduced in oleylamine at 160°C while iron pentacarbonyl was thermally decomposed to obtain Fe / Pt nanowires with a diameter of 2nm to 3nm (see Angew.Chem.Int.Ed.46(2007), 6333 -6335), and then heated and stirred under acidic conditions to corrode the Fe wrapped on the outside of the Pt nanowires to obtain platinum nanowires. Scanning the obtained nanowires with an electron microscope, the results are shown in the attached figure 2 , from attached figure 2 It can be seen that the diameter of the platinum nanowires is 2 nm to 3 nm.

Embodiment 2

[0031] In a reaction flask of 20g m-xylene, 2.85g compound (IIA) and 3.09g compound (IIIA) were firstly added, and then 0.4g sodium hydroxide and 1.4mg platinum nano-compound were added respectively. Put the system into an autoclave, cool, vacuumize, release hydrogen, cycle 3 to 4 times, put in hydrogen, and return to room temperature. The system was kept in an oil bath at 80°C with a hydrogen pressure of 0.2Mpa, and the product (IA) was obtained after heating for 15h with a yield of 78%.

[0032]

[0033]

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Abstract

The invention discloses a preparation method of phthaloyl azo dye, which comprises the following steps of: mixing N-alkyl-4-nitrol-phthalimide with nitrobenzene compounds according to equal molar ratio, adding the mixture into alkali-containing solvent, feeding hydrogen into the solvent under the existence of catalyst, and conducting reaction for 4-24h at room temperature being approximately 98DEG C under low pressure or normal pressure to directly prepare the phthaloyl azo dye. Compared with the existing disclosed technique, the method provided by the invention has the advantages that the synthesis process flow is short and the defects of classic synthesis method of diazotization-coupling are avoided; the safety is high and only low-pressure or normal-pressure catalytic hydrogenation for coupling is needed; the energy consumption is low and the reaction is conducted at room temperature being approximately 98DEG C; the separation and the purification are simple to conduct and the intermediates are not needed to be purified or separated by using a great quantity of solvent; the quantity of the discharged sewage is less and the secondary environmental pollution is avoided.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and relates to a preparation method of a phthalimide-based azo dye, in particular to a method for preparing an azo dye from two asymmetric structure nitro compounds. Background technique [0002] Azo dyes are a class of important compounds in the chemical industry. Phthalimide-based azo dyes are a class of disperse dyes with excellent performance. The preparation method of phthalimide-based azo dyes has long been published. As disclosed in invention patents CN1069670C, CN1289607C, CN1326945C, CN1249171C, CN100379825C, it is all adopted to first reduce N-alkyl-4-nitro-phthalimide to N-alkyl-4-amino-o- Phthalimide, then diazotized, and then coupled with the coupling component in the system. The biggest disadvantage of preparing azo dyes with diazotization coupling reaction is that a large amount of nitrite is needed to form diazonium salt, which will produce a large amount of inorganic salts and wast...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B27/00
Inventor 顾宏伟姚晨华曹雪琴朱亚伟胡磊俞啸天
Owner ZHEJIANG WANFENG CHEM
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