Method for synthesizing metal phthalocyanine from phthalonitrile under catalysis of urea-choline chloride

A technology of choline chloride and phthalonitrile, which is applied in the direction of organic chemistry, can solve the problems of application limitations, poor solubility of phthalocyanine compounds, etc., and achieve the effect of ensuring the reaction temperature

Pending Publication Date: 2019-10-25
石家庄搏澳增塑材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In recent years, metal phthalocyanine has become a research hotspot in the fields of functional materials, chemistry, physics and medicine, but its application is limited due to the poor solubility of phthalocyanine compounds in solvents.

Method used

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  • Method for synthesizing metal phthalocyanine from phthalonitrile under catalysis of urea-choline chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0014] With 10 kilograms of 4-amino-phthalonitrile, urea and choline chloride mol ratio are 80 kilograms of urea-choline chloride deep eutectic solvent DES of 2.2:1, zinc chloride 2.6 kilograms, put into reactor 1 , heated to 120°C with steam, and reacted for 2 hours. After the material is diluted and washed with an appropriate amount of water in the washing tank 2, it is filtered in the filter 3, and the material containing urea-choline chloride deep eutectic solvent DES, etc. is dehydrated under negative pressure in the dehydration tank 4, and then sent back to the reaction kettle 1 is recycled; the filter cake is further purified in the refining equipment 5 to finally obtain 6.9 kilograms of cobalt phthalocyanine product.

Embodiment 2

[0016] 10 kilograms of 4-hydroxyl-phthalonitrile, urea and choline chloride mol ratio are 82 kilograms of urea-choline chloride deep eutectic solvent DES of 2:1, cobalt chloride 2.4 kilograms, drop into reactor 1 , heated to 115°C with steam, and reacted for 3 hours. After the material is diluted and washed with an appropriate amount of water in the washing tank 2, it is filtered in the filter 3, and the material containing urea-choline chloride deep eutectic solvent DES, etc. is dehydrated under negative pressure in the dehydration tank 4, and then sent back to the reaction kettle 1 is recycled; the filter cake is further purified in the refining equipment 5 to finally obtain 7.2 kilograms of cobalt phthalocyanine product.

Embodiment 3

[0018] 10 kilograms of 3-isoamyloxy-phthalonitrile, urea and choline chloride mol ratio are 84 kilograms of urea-choline chloride deep eutectic solvent DES of 1.8:1, copper chloride 2.6 kilograms, drop into In reactor 1, heat to 125° C. by steam, and react for 2 hours. After the material is diluted and washed with an appropriate amount of water in the washing tank 2, it is filtered in the filter 3, and the material containing urea-choline chloride deep eutectic solvent DES, etc. is dehydrated under negative pressure in the dehydration tank 4, and then sent back to the reaction kettle 1 is recycled; the filter cake is further purified in the refining equipment 5 to finally obtain 6.8 kilograms of copper phthalocyanine product.

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Abstract

The invention provides a clean method for synthesizing metal phthalocyanine from phthalonitrile or a phthalonitrile derivative substituted by different functional groups and a metal chloride or nitrate under catalysis of a urea-choline chloride eutecticevaporate green solvent. Multiple functional metal phthalocyanine compounds such as cobalt, copper, zinc, nickel, iron and manganese are synthesized under a gentle condition, the yield is high, and in addition, toxic and organic solvents such as amyl alcohol and expensive DBU (diazabicyclo) organic alkali catalysts which are used in a conventional process are not used. The urea-choline chloride eutecticevaporate solvent DES is adopted as a solvent for dissolving and dispersing reactants, meanwhile, a function of catalyzing formation of a phthalocyanine cycle is also achieved, and the reaction temperature for forming the phthalocyanine cycle is 110-130 DEG C. The low reaction temperature also ensures the uniformity, completeness and highpurity of a phthalocyanine product structure. The synthesis process is green, remarkable environment benefits can be made, the energy can be saved, and meanwhile, environment protection can be achieved.

Description

technical field [0001] The invention belongs to the field of green chemical synthesis, and specifically relates to a method for using urea-choline chloride deep eutectic green solvent to catalyze phthalonitrile or phthalonitrile substituted with different functional groups and metal ions to synthesize metal phthalocyanine series compounds. Background technique [0002] Phthalocyanine is a class of macrocyclic conjugated complexes with a carbon-nitrogen conjugated double bond, a 16-centre 18π-electron aromatic conjugated system composed of 8 N atoms and 8 C atoms. The distribution of electrons in the molecule is uniform, the lengths of all C-N bonds are approximately equal, and the four benzene rings in the molecule are difficult to deform, so phthalocyanine has very good thermal and chemical stability. In addition, phthalocyanine is heat-resistant, light-resistant, water-resistant, and resistant to acid, alkali and various organic solvents. Its molecular structure has the ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 冯树波宋丽英宋弥新
Owner 石家庄搏澳增塑材料科技有限公司
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