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Monomer preparation method of dihalide and binitro triaryl methyl-1, 3, 5-triazine

A dinitrotriaryl and dinitrotriphenyl technology, applied in the field of dihalogenation and dinitrotriaryl-1, can solve the problems of long cycle, complex operation, long reaction route, etc., and achieve by-product suppression , high yield, easy product effect

Inactive Publication Date: 2014-04-02
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction route of the three-step method and the four-step method is long, the cycle is long, the experimental steps are cumbersome, and the final yield and purity are not high
In the three-step process, a strongly acidic catalyst such as SO 3 , a large amount of waste acid is produced, which makes the operation complicated and the post-treatment difficult
Although the one-step method is to simplify the synthesis steps, the yield is still not high, and the reaction selectivity is poor. When generating dihalogenated products, it is accompanied by derivatives of monohalogenated and trihalogenated, which are difficult to separate

Method used

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  • Monomer preparation method of dihalide and binitro triaryl methyl-1, 3, 5-triazine

Examples

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example 1

[0023] Example 1: Synthesis of 2,4-(4-dichlorophenyl)-6-phenyl-1,3,5-s-triazine (BCPT)

[0024] Sodium methoxide (0.54g, 0.01mol) was dissolved in 100mL of anhydrous methanol at room temperature, p-chlorobenzonitrile (13.76g, 0.1mol) was added, stirred for 10h, ammonium chloride (5.4g, 0.1mol) was added, and the Temperature to reflux temperature for 3 hours, the reaction was stopped, the reaction solution was acidified, the solvent methanol was evaporated under reduced pressure, the unreacted raw material p-chlorobenzonitrile was recovered with ether, and the crude product of p-chlorobenzamidine hydrochloride was recrystallized with acidic deionized water Finally, filtered and dried, the yield was 92%. IR (KBr): 3459cm -1 -3054cm -1 (N-H), 1679cm -1 (C=N stretching vibration peak), 1595cm -1 , 1529cm -1 , 1480cm -1 (stretching vibrations generated by the benzene ring skeleton), 1089 cm -1 (δ(C-H)), 846cm -1 (γ(=C-H)). 1 H NMR (d 6 -DMSO, δ): 9.53 (2H, s), 9.35 (2H, s...

Embodiment 2

[0026] Example 2: Synthesis of 2,4-(4-difluorophenyl)-6-phenyl-1,3,5-s-triazine (BFPT)

[0027] The method is as in Example 1, and the raw material is changed to p-fluorobenzonitrile. Other steps are basically the same as Example 1. The melting point is 260.2-260.8°C (DSC test). GC / MS (M+calcd as C 21 h 13 N 2 f 2 345.1078) m / z: 345.1067 (M+).

Embodiment 3

[0028] Example 3: Synthesis of 2,4-(4-difluorophenyl)-6-phenyl-1,3,5-s-triazine (BCPT) using Lewis acid catalysis

[0029] The synthetic method of p-chlorobenzamidine hydrochloride is as embodiment 1. 0.01 mol of p-chlorobenzamidine hydrochloride, 10 mL of benzoyl chloride, a reaction temperature of 150° C., an amount of zinc chloride of 2.5 mmol, a reaction time of 4 hours, and a crude product yield of 85%. Wherein the content of trisubstituted derivatives is 2%, and the main product of disubstituted is 98%.

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Abstract

The invention relates to a monomer preparation method of dihalide and binitro triaryl methyl-1, 3, 5-triazine, which is used for synthesizing a polyarylether polymer which contains a triaryl methyl s-triazine structure. The preparation process comprises two steps of: taking halide or nitrobenzonitrile as a starting material, generating imido ester in alcoholic solution under the catalysis of sodium alkoxide after addition reaction, producing halide or nitro amidine hydrochloride after ammonia which is released by heating ammonium chloride replaces alkoxy, and obtaining dihalide or binitro triphenyl s-triazine monomer after the high temperature cyclization reaction of purified amidine salt and benzoyl chloride. The halide or binitro triphenyl s-triazine monomer derivative which is prepared through the two steps is mainly disubstituted and trisubstituted, the mono-substituted byproduct is restrained, so during the purification process of the product, the solubility differences of the disubstituted and trisubstituted derivatives in the benzene derivative are mainly used, so the polymerized disubstituted halide or nitro triphenyl s-triazine monomer is produced at high yield. The reaction characteristics are high yield, reduced pollution and saved cost.

Description

technical field [0001] The present invention relates to a kind of synthesis method of dihalogenated and dinitrotriaryl-1,3,5-triazine monomer, specifically refers to a kind of method for synthesizing polyarylene ether polymer containing triaryl-s-triazine structure Monomer preparation of dihalogenated and dinitrotriaryl-1,3,5-triazines. Background technique [0002] Poly(triaryl-1,3-5-s-triazine) has excellent comprehensive properties due to its special aromatic ring and s-triazine ring planar conjugated structure, such as excellent heat resistance, high strength, high modulus , flame retardant, chemical corrosion resistance, etc., so it has important applications in aerospace, national defense, electronics and other industrial fields. At the same time, triphenyl-s-triazine and its derivatives are important organic intermediates. Due to its unique photoelectric properties and crystal properties, and can be applied to fields such as optoelectronic devices and flat-panel disp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/24
Inventor 蹇锡高王锦艳刘程张守海卢冬明
Owner DALIAN UNIV OF TECH