Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine

A technology of aminocaproic acid and carboxylate, which is applied in 2 fields, can solve the problems such as not being found, and achieve the effect of simple and easy reaction operation, short time and mild reaction conditions

Inactive Publication Date: 2011-02-16
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, we have not checked the literature reports about the synthesis method of 2,4,6-tris(aminocaproic acid)-1,3,5-triazine

Method used

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  • Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine
  • Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine
  • Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add sodium hydroxide (32.8g, 0.82mol), caprolactam (92.6g, 0.82mol) and 400mL water respectively in a 1000mL three-neck round bottom flask equipped with a magnet, reflux condenser and thermometer, start stirring and control the temperature at 60 °C for 30 minutes. After the reaction, cyanuric chloride (50.4 g, 0.27 mol) was added, the temperature was raised to 70° C., and maintained for 120 minutes, during which the reaction progress was monitored by TLC, and ethanol was used as a developing solvent. Cool down to 30°C, add concentrated hydrochloric acid (82g, 0.82mol) with a concentration of 36.5%, precipitate a wet cake-like white solid, stir for 30 minutes, filter with suction, and dry at 80°C to obtain 54 grams of product, yield 88.7%. m.p.181-183℃.IR: v=3300, 2942, 2364, 1710, 1567, 1413, 1344, 1257, 1186, 843, 785, 742cm -1 . 1 H NMR (DMSO, 300MHz): δ=1.25(t, J=6.9Hz, 6H), 1.37-1.60(m, 12H), 2.14-2.28(m, 12H), 6.20-6.69(t, J=6.3Hz , 3H).Anal.Calcd for C 21 h 3...

Embodiment 2

[0023] Add sodium hydroxide (43.7g, 1.1mol), caprolactam (92.6g, 0.82mol) and 400mL water respectively in a 1000mL three-neck round bottom flask equipped with a magnet, reflux condenser and thermometer, start stirring and control the temperature at 70 °C for 40 minutes. After the reaction, cyanuric chloride (50.4 g, 0.27 mol) was added, the temperature was raised to 75° C., and maintained for 100 minutes, during which the reaction progress was monitored by TLC, and ethanol was used as a developing solvent. Cool down to 35°C, add concentrated hydrochloric acid (164g, 1.64mol) with a concentration of 36.5%, precipitate a wet cake-like white solid, stir for 50 minutes, filter with suction, and dry at 80°C to obtain 54 g of the product with a yield of 88.4%. m.p.181-183℃.IR: v=3300, 2942, 2364, 1710, 1567, 1413, 1344, 1257, 1186, 843, 785, 742cm -1 . 1 H NMR (DMSO, 300MHz): δ=1.25(t, J=6.9Hz, 6H), 1.37-1.60(m, 12H), 2.14-2.28(m, 12H), 6.20-6.69(t, J=6.3Hz , 3H).Anal.Calcd for C...

Embodiment 3

[0025] Add sodium hydroxide (54.6g, 1.37mol), caprolactam (92.6g, 0.82mol) and 400mL water respectively into a 1000mL three-neck round bottom flask equipped with a magnet, reflux condenser and thermometer, start stirring and control the temperature at 65 °C for 30 minutes. After the reaction, cyanuric chloride (50.4 g, 0.27 mol) was added, the temperature was raised to 75° C., and maintained for 90 minutes, during which the reaction progress was monitored by TLC, and ethanol was used as a developing solvent. Cool down to 40°C, add concentrated hydrochloric acid (219g, 2.19mol) with a concentration of 36.5%, precipitate a wet cake-like white solid, stir for 60 minutes, filter with suction, and dry at 80°C to obtain 53 g of the product, with a yield of 87%. m.p.181-183℃.IR: v=3300, 2942, 2364, 1710, 1567, 1413, 1344, 1257, 1186, 843, 785, 742cm -1 . 1 H NMR (DMSO, 300MHz): δ=1.25(t, J=6.9Hz, 6H), 1.37-1.60(m, 12H), 2.14-2.28(m, 12H), 6.20-6.69(t, J=6.3Hz , 3H).Anal.Calcd for ...

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Abstract

The invention discloses a method for preparing an organic ternary polycarboxylic acid dustless antirust additive 2,4,6-tri(amino caproyl)-1,3,5-triazine by adopting a one-pot method, which comprises the following steps of: ring-opening caprolactam with alkali to generate carboxylate of aminocaproic acid first; then performing a substitution reaction by the carboxylate of aminocaproic acid and cyanuric chloride; and finally, acidizing with hydrochloric acid to prepare derivatives of organic ternary polycarboxylic acid. The preparation method is free from a toxic organic solvent and employs common water as a solvent for reaction. The preparation method ha the advantages of simple process operation, low production cost and low environmental pollution and is more suitable for large scale industrial production.

Description

[0001] This invention is funded by Tianjin Normal University Development Fund (52X09042). technical field [0002] The invention belongs to the technical field of organic synthesis and relates to a preparation method of 2,4,6-tris(aminocaproyl)-1,3,5-triazine. Background technique [0003] 2,4,6-tris(aminocaproic acid)-1,3,5-triazine is a very important water-based rust inhibitor. It has superior performance, mainly including: it can be used to protect various metals from rusting, and it works better with Irgamet 42; excellent hard water stability; extremely low foaming tendency, good air release; its triethanolamine Sodium salt will not affect the performance of extreme pressure antiwear agent; it can replace sodium nitrite when used in conjunction with AMINE O, and the anti-rust effect of adding 0.5% is equivalent to adding 6% sodium nitrite; there is no tendency to form nitrosamines; Chlorine-free and extremely low toxicity. In conclusion, 2,4,6-tris(aminocaproic acid)-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/70
Inventor 刘巨艳王广辉曹改娥王敬凤刘海旺
Owner TIANJIN NORMAL UNIVERSITY
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