Preparation method of 1,2,7,8-4-nitrile perylene
A technology of nitrile-based perylene and acetonitrile, which is applied in the field of 1,2,7,8-tetranitrile-based perylene and its preparation, can solve the problems of difficult handling, high price, environmental hazards and the like, and achieves low cost, high synthesis efficiency, Environmentally friendly effect
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[0017] Preparation Example of 1,2,7,8-perylenetetracarboxylic acid
[0018] 1,2,7,8-perylenetetracarboxylic acid can be obtained by hydrolyzing 3,4,9,10-perylenetetracarboxylic dianhydride according to conventional methods. Add 3,4,9,10-perylenetetracarboxylic dianhydride to NaOH aqueous solution, heat and reflux for 3 hours, cool to room temperature, add hydrochloric acid to acidify, evaporate solvent to concentrate, cool to room temperature, and precipitate 1,2,7,8- Perylenetetracarboxylic acid crystals.
Embodiment 1
[0020] Add 10 mmol of 1,2,7,8-perylenetetracarboxylic acid and 40 mmol of ethyl carbamate into 100 mL of acetonitrile, and control the temperature of the reaction system at 65 o C, add 40 mmol SOCl dropwise 2 , and reacted for 2 hours under stirring conditions to obtain a reaction mixture. The reaction mixture was at normal pressure, 70 o Under the condition of C, the low-boiling point organic matter was distilled off to obtain the residue A. Stop heating when the temperature of Residue A drops to 40 o C, change to a vacuum distillation unit. At 3 mm Hg, 80 o Under the condition of C, high-boiling point organic matter was distilled off under reduced pressure to obtain residue B. The residue B was recrystallized from acetonitrile to obtain 2.68 g of red solid with a yield of 76.1%. The reaction equation is as figure 1 .
[0021] The red solid is characterized by the following spectrum, 1 HNMR (D 6 C 6 ): δ = 7.95 (d, 4H), 8.10 (d, 4H), MS (FI): 352.2; elemental anal...
Embodiment 2
[0023] Add 10 mmol of 1,2,7,8-perylenetetracarboxylic acid and 50 mmol of ethyl carbamate into 100 mL of acetonitrile, and control the temperature of the reaction system at 65 o C, add 40 mmol SOCl dropwise 2 , and reacted for 2 hours under stirring conditions to obtain a reaction mixture. The reaction mixture was heated at normal pressure, 80 o Under the condition of C, low-boiling point organic matter is distilled off to obtain residue A. When the temperature of residue A drops to 40 o C, replaced by a vacuum distillation device, at 3 mm Hg, 90 o Under C, the high-boiling point organic matter was distilled off under reduced pressure to obtain residue B. The residue B was recrystallized from acetonitrile to obtain 2.75 g of a red solid with a yield of 78.1%. using thin layer chromatography and 1 HNMR spectrum proved that the red solid was 1,2,7,8-tetranitrile perylene.
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