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Preparation process of aromatic nitrile compound

A preparation process and compound technology, which is applied in the field of preparation of aromatic nitrile compounds, can solve problems such as environmental pollution, inconvenient treatment, and heavy metal pollution, and achieve the effect of simple feeding and post-processing, and easy recovery of catalysts

Inactive Publication Date: 2012-10-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, NaCN and KCN are highly toxic; Zn(CN) 2 CuCN and CuCN are highly toxic, and because of the need for stoichiometric use, they will cause serious heavy metal pollution; TMSCN is easy to absorb moisture and is inconvenient to handle. 3 ) 2 C(OH)CN will release highly toxic hydrogen cyanide gas in the reaction process, causing serious environmental pollution [Tetrahedron, 1984, 40(9), 1433; J. Org. Chem., 1979, 44(24) ,4443; JACS, 2003, 125(100, 2890, Org. lett. 2004, 6(170, 2837]

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 100-liter reactor, add 30 liters of xylene, 30 moles of p-methylbromobenzene, 6 moles of potassium ferrocyanide, 0.573 kg (3 moles, 0.1 equivalent) of cuprous iodide, and 1 kg of potassium iodide in sequence under nitrogen protection. (6 moles, 0.2 equivalents), 2.64 kg of N,N'-dimethylethylenediamine (30 moles, 1.0 equivalents), stirred and reacted at 145°C for 50 hours under nitrogen protection, ended the reaction, cooled to room temperature, and filtered Recover the inorganic salt, recover the solvent xylene from the filtrate under reduced pressure, carry out fractional distillation on the residue to recover N,N'-dimethylethylenediamine, and obtain p-toluonitrile, the yield is 91%, white solid, mp 25- 26°C; 1 H NMR (CDCl3): 2.42 (s, 3H), 7.27 (d, J = 8.0 Hz, 2H), 7.54 (d, J = 8.2 Hz, 2H); 13 C NMR (CDCl3): 21.8, 109.3, 119.1, 129.8, 132.0, 143.6; IR (KBr): (CN) 2226 cm -1 ; EI-MS m / z : 117 (M+, 100).

Embodiment 2

[0020] In a 100-liter reactor, add 50 liters of xylene, 30 moles of p-bromobiphenyl, 5.5 moles of potassium ferrocyanide, 0.573 kilograms (3 moles, 0.1 equivalent) of cuprous iodide, and 1 kilogram of potassium iodide ( 6 moles, 0.2 equivalents), 2.64 kg of N,N'-dimethylethylenediamine (30 moles, 1.0 equivalents), stirred and reacted at 150°C for 48 hours under nitrogen protection, ended the reaction, cooled to room temperature, and recovered by suction filtration Inorganic salt, the filtrate was decompressed to recover the solvent xylene and N,N'-dimethylethylenediamine, the residue was recrystallized from ethanol to obtain p-cyanobiphenyl, the yield was 71%, white solid, mp 81-82 °C ; 1 H NMR (CDCl3): 7.39-7.53 (m, 3H), 7.56-7.62 (m, 2H), 7.66-7.75 (m, 4H); 13 C NMR (CDCl3): 110.8, 118.9, 127.2. 127.7, 128.6, 129.1, 132.6, 139.1, 145.6; IR (KBr): (CN) 2225 cm-1; EI-MS m / z : 179 (M + , 100).

Embodiment 3

[0022] In a 100-liter reactor, under nitrogen protection, add 40 liters of mesitylene, 30 moles of 4-bromo-4'-ethylbiphenyl, 6 moles of potassium ferrocyanide, 2.5 moles of cuprous iodide, and 5 moles of potassium iodide , 24 moles of N,N'-dimethylethylenediamine, stirred and reacted at 165°C for 48 hours under nitrogen protection, ended the reaction, cooled to room temperature, recovered inorganic salts by suction filtration, and recovered solvent mesitylene and N , N'-dimethylethylenediamine, the residue was subjected to high-vacuum fractional distillation to obtain liquid crystal intermediate 4-cyano-4'-ethylbiphenyl, the yield was 85%, mp73~74 ℃, clearing point 22 ℃, 1 H NMR ( 400 MHz CDCl 3 ): 1. 28 (m ,3 H ,-CH3 ) , 2. 74 (m ,2H ,-CH2-) ,7.36~7. 85 (m ,8H ,-Ar-)ppm.

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PUM

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Abstract

The invention discloses a preparation process of an aromatic nitrile compound. According to the preparation process, alkylbenzene is used as a reaction solvent, copper iodide, potassium iodide and N, N'- dimethyl ethylenediamine are used as a combined catalyst, bromo-aromatic hydrocarbon reacts with potassium ferrocyanide in nitrogen at 120-170 DEG C for 24-60 hours to obtain a mixture, and then the mixture is cooled to room temperature to be filtered. After the solvent is recovered, a filtrate is processed through decompression fractionation or recrystallized to obtain the corresponding aromatic nitrile compound. An obtained product has the advantage of high yield and purity. Compared with the existing synthetic method, the preparation process has the advantages of mild reaction condition, short reaction process, utilization of cheap nontoxic cyano chemical reagent, simplicity in feeding and post treatment, easiness in recovery of the catalyst, and easiness in realization of industrial production.

Description

technical field [0001] The invention relates to a preparation method of an organic synthesis intermediate, in particular to a preparation process of an aromatic nitrile compound. Background technique [0002] Aromatic nitrile compounds are important fine chemical intermediates, which can be hydrolyzed to prepare acids or reduced to amines, and are widely used in the fields of pharmaceuticals, pesticides, dyes, plastic additives and fine organic chemicals; important aromatic nitrile fine chemical intermediates The body includes the key intermediate of antidepressant citalopram 5-cyanophthalide, the key intermediate of antihypertensive drug sartan biphenyl, the intermediate of hydralazine drugs o-cyanobenzaldehyde, and the liquid crystal material 4'-alkyl -4-cyanobiphenyl and so on. [0003] At present, there are three main process routes in the production of aromatic nitrile compounds at home and abroad: (1) elimination method; (2) ammoxidation method; (3) substitution metho...

Claims

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Application Information

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IPC IPC(8): C07C253/14C07C255/50
Inventor 毛侦军全丽丽屈海军林旭锋
Owner ZHEJIANG UNIV
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