Synthetic method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine

A technology of tetrahydroxypiperazine and diformyl, which is applied in the synthesis field of piperazine compounds, can solve the problems of long synthesis period, product loss, and product purity can only reach 98%, so as to shorten the synthesis period and simplify the operation process , save the effect of the refining process

Inactive Publication Date: 2015-01-07
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The product yield of this synthetic method is low (68%), needs to be through complicated refining and purifying, and product loss is serious, and product purity also can only reach 98%, and synthetic period is long (3 hours), and the amount of catalyst NaOH in synthetic process passes through Adjusting PH is difficult to control, and the reaction needs external heating to complete

Method used

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  • Synthetic method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine
  • Synthetic method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine
  • Synthetic method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine

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Experimental program
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Embodiment 1

[0015] Add 145g 40% (1.0mol) glyoxal aqueous solution and 45g (1.0mol) formamide to a 500ml three-neck round bottom flask, stir to make it fully mixed, then add 10ml (0.075mol) triethylamine dropwise, control the temperature At 45°C, after 8 minutes of dropwise addition, a white precipitate appeared immediately, filtered while hot, washed with water and ethanol, and dried to obtain 82.5 g of a white powdery solid with a purity of 99.5% and a yield of 80%.

[0016] Melting point: 192~195°C (reported value 196°C).

[0017] Structure Identification:

[0018] 1 HNMR (DMSO-d 6 , δ / ppm): δ8.26(s, 2H), δ6.04(s, 2H), δ5.92(s, 2H), δ5.46(s, 2H), δ4.98(s, 2H) .

[0019] 13 CNMR (DMSO-d 6 , δ / ppm), δ: 164.4, 164.3, 79.3, 78.9, 72.5, 72.2.

[0020] Elemental analysis (C 6 h 10 N 2 o 6 ):

[0021]

[0022] Mass Spectrum: MS(m / e)206(M + ).

[0023] The above structural identification data prove that the substance obtained by this synthesis method is indeed 1,4-diformyl-2,3,...

Embodiment 2

[0025] Add 145g 40% (1.0mol) glyoxal aqueous solution and 45g (1.0mol) formamide to a 500ml three-neck round bottom flask, stir to make it fully mixed, then add 12ml (0.09mol) triethylamine dropwise, control the temperature At 45°C, after 10 minutes of dropwise addition, a white precipitate appeared immediately, which was filtered while hot, washed with water and ethanol, and dried to obtain 78.2 g of a white powdery solid with a purity of 99% and a yield of 75.9%.

Embodiment 3

[0027] Add 145g 40% (1.0mol) glyoxal aqueous solution and 45g (1.0mol) formamide to a 500ml three-neck round bottom flask, stir to make it fully mixed, then add 8ml (0.06mol) triethylamine dropwise, and control the temperature At 45°C, after 5 minutes of dropwise addition, a white precipitate appeared immediately, which was filtered while hot, washed with water and ethanol, and dried to obtain 75.2 g of a white powdery solid with a purity of 99.2% and a yield of 73%.

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Abstract

The invention discloses a synthetic method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine. The 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine is shown in structural formula in the specification. The synthetic method comprises the following steps: adding glyoxal aqueous solution and formamide in a reaction vessel according to the molar ratio of 1: (0.5-2), stirring and fully mixing; dropwise adding organic alkali in which the molar ratio of water to glyoxal is 100: (6-15), controlling the temperature within 30-60 DEG C and immediately generating white precipitates after the completion of dropwise adding within 5-10 minutes, filtering, washing the precipitates with water and an organic solvent and drying to obtain the 1,4-diformyl,3,5,6-tetrahydroxypiperazine. The synthetic method is used for the preparation of the 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine.

Description

technical field [0001] The invention relates to a synthesis method of piperazine compounds, in particular to a synthesis method of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine. Background technique [0002] 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5,5,0,0 5.9 0 3.11 ] Dodecane (TEX) is a typical cage insensitive high-energy explosive. The multi-ring structure makes TEX extremely high in energy, and its high detonation and insensitivity make it of great application value in casting and pressing explosives. TEX can be obtained by nitration of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine (THDFP). Literature [Cui Kejian, Xu Zhibin, Shi Yuhui, etc. 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5,5,0,0 5.9 0 3.11 ] Synthesis of dodecane [J]. Journal of Beijing Institute of Technology, 2013, 33 (4): 413-415.] The synthesis method of THDFP reported is to use 40% glyoxal aqueous solution and formamide as raw materials, and NaOH as catalyst , first add NaOH soluti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/04
CPCC07D241/04
Inventor 张创军王友兵周杰文张蒙蒙黄凤臣胡琳琳席伟汪强
Owner XIAN MODERN CHEM RES INST
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