CN101973949A - Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine - Google Patents
Method for preparing 2,4,6-tri(amino caproyl)-1,3,5-triazine Download PDFInfo
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- CN101973949A CN101973949A CN 201010546770 CN201010546770A CN101973949A CN 101973949 A CN101973949 A CN 101973949A CN 201010546770 CN201010546770 CN 201010546770 CN 201010546770 A CN201010546770 A CN 201010546770A CN 101973949 A CN101973949 A CN 101973949A
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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
The present invention subsidizes (52X09042) by Tianjin Normal University's development fund.
Technical field
The invention belongs to technical field of organic synthesis, relate to 2,4,6-three (hexosamine base)-1,3,5-triazines preparation method.
Background technology
2,4,6-three (hexosamine base)-1,3,5-triazines is a kind of very important water-based antirust agent.It has superior performance, mainly comprises: can be applied to protect multiple metal and get rusty, and better with Irgamet 42 fiting effects; Splendid hard water stability; Extremely low foam tendency, good air release property; The sodium salt of its trolamine can not influence the performance of extreme pressure anti-wear additives; Be used with AMINE O and can replace Sodium Nitrite, each adds 0.5% rust-proof effect and is equal to and adds 6% Sodium Nitrite; Do not form the trend of nitrosamine; Not chloride, toxicity is extremely low.In a word, 2,4,6-three (hexosamine base)-1,3,5-triazines is a class superior performance that is applicable to all water based lubrications and cleaning system, the Ashless stain-resistant agent of environmental protection.
Up to now, we do not find about 2,4, the bibliographical information of 6-three (hexosamine base)-1,3,5-triazines synthetic method.Almost the whole world 90% 2,4,6-three (hexosamine base)-1,3,5-triazines comes from same manufacturer-Ciba (Ciba Specialty Chemicals), and Ciba is maintained secrecy about this technique for synthesizing compounds.
Summary of the invention
The objective of the invention is to break through 2,4, the synthetic technology barrier of 6-three (hexosamine base)-1,3,5-triazines provides a kind of 2,4, the preparation method of 6-three (hexosamine base)-1,3,5-triazines.
The inventor is surprised to find in test: with hexanolactam, cyanuric chloride, sodium hydroxide, hydrochloric acid is main raw material(s), be solvent with common tap water in the reaction, cut off and have toxic organic solvent, controlled temperature in the time of 25-80 ℃, but stable by the carboxylate salt of hexosamine and the substitution reaction preparation quality between the cyanuric chloride, yield high 2,4,6-three (hexosamine base)-1,3,5-triazines.The inventor provides following technical scheme for this reason:
A kind of organic ternary poly carboxylic acid derivative's preparation method is characterized in that, in polar solvent, make the hexanolactam hydrolysis generate the carboxylate salt of hexosamine with alkali earlier, then the carboxylate salt of hexosamine again with cyanuric chloride generation substitution reaction, the method for last acid out prepares this organic ternary poly carboxylic acid derivative.Promptly in polar solvent, adopt " one kettle way ", make the carboxylate salt (II) of hexanolactam (I) open loop generation hexosamine earlier with alkali, and then substitution reaction takes place, separate out with hcl acidifying at last with cyanuric chloride (III);
Polar solvent of the present invention is a water.Described alkali is sodium hydroxide.Sodium hydroxide wherein: hexanolactam: cyanuric chloride: the mol ratio of hydrochloric acid is 3-6: 3: 0.8-1: 3-9; The temperature of reaction 25-70 of hexanolactam hydrolysis ℃, reaction times 30-60 minute; The temperature of the carboxylate salt of hexosamine and cyanuric chloride generation substitution reaction is 25-80 ℃, reaction times 60-180 minute; The temperature of reaction of acid out is 25-50 ℃, and the reaction times is 30-180 minute.
The present invention prepares 2,4, and 6-three (hexosamine base)-1,3,5-triazines mainly adopts TLC monitoring reaction process, uses ethanol as developping agent.
2,4,6-three (hexosamine base)-the 1,3,5-triazines compound is as follows:
Disclosed by the invention 2,4, the advantage that the preparation method had and the characteristics of 6-three (hexosamine base)-1,3,5-triazines are:
(1) operation is simple and easy to do, the reaction conditions gentleness.
(2) solvent for use is a water, and is cheap and easy to get and environmentally friendly, is difficult for causing environmental pollution.
(3) the reaction required time is short, yield height, the purity height of products obtained therefrom, superior performance.
(4) the prepared organic ternary poly carboxylic acid Ashless stain-resistant agent of the present invention goes for all water based lubrications and cleaning system.Its production cost is low, and profit margin is big, is more suitable for large-scale industrial production.
Embodiment
The present invention is described further below in conjunction with embodiment, and embodiment only is indicative, means that never it limits the scope of the invention by any way.
All raw materials all are to buy from chemical reagents corporation both domestic and external, through continue purifying but directly use.The fusing point of product is to be X in model
4Measure on the fusing point instrument of Micro;
1H NMR be deuterium for DMSO in, be to measure on the instrument of Bruker Avance 300 in model; Infrared spectra is the method with the KBr compressing tablet, in model is to measure on the infrared spectrometer of Jasco FT/IR-620v.More than test gained data all contrast with the actual value of standard model.
Embodiment 1
In three mouthfuls of round-bottomed flasks of the 1000mL that magneton, reflux exchanger and thermometer are housed, add respectively sodium hydroxide (32.8g, 0.82mol), hexanolactam (92.6g, 0.82mol), 400mL water, start stir and temperature control in 60 ℃ of reactions 30 minutes.After reaction finishes, add cyanuric chloride (50.4g 0.27mol), is warming up to 70 ℃, kept 120 minutes, during with TLC monitoring reaction process, with ethanol as developping agent.Be cooled to 30 ℃, add concentration and be 36.5% concentrated hydrochloric acid (82g 0.82mol), separates out wet pie white solid, stirred 30 minutes, suction filtration, in 80 ℃ of oven dry, 54 restrain products, yield 88.7%.m.p.181-183℃.IR：v＝3300，2942，2364，1710，1567，1413，1344，1257，1186，843，785，742cm
-1.
1H?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
21H
36N
6O
6：C，53.83；H，7.74；N，17.94.Found：C，53.91；H，7.64；N，17.93.
Embodiment 2
In three mouthfuls of round-bottomed flasks of the 1000mL that magneton, reflux exchanger and thermometer are housed, add respectively sodium hydroxide (43.7g, 1.1mol), hexanolactam (92.6g, 0.82mol), 400mL water, start stir and temperature control in 70 ℃ of reactions 40 minutes.After reaction finishes, add cyanuric chloride (50.4g 0.27mol), is warming up to 75 ℃, kept 100 minutes, during with TLC monitoring reaction process, with ethanol as developping agent.Be cooled to 35 ℃, add concentration and be 36.5% concentrated hydrochloric acid (164g 1.64mol), separates out wet pie white solid, stirred 50 minutes, suction filtration, in 80 ℃ of oven dry, 54 restrain products, yield 88.4%.m.p.181-183℃.IR：v＝3300，2942，2364，1710，1567，1413，1344，1257，1186，843，785，742cm
-1.
1H?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
21H
36N
6O
6：C，53.83；H，7.74；N，17.94.Found：C，53.91；H，7.64；N，17.93.
Embodiment 3
In three mouthfuls of round-bottomed flasks of the 1000mL that magneton, reflux exchanger and thermometer are housed, add respectively sodium hydroxide (54.6g, 1.37mol), hexanolactam (92.6g, 0.82mol), 400mL water, start stir and temperature control in 65 ℃ of reactions 30 minutes.After reaction finishes, add cyanuric chloride (50.4g 0.27mol), is warming up to 75 ℃, kept 90 minutes, during with TLC monitoring reaction process, with ethanol as developping agent.Be cooled to 40 ℃, add concentration and be 36.5% concentrated hydrochloric acid (219g 2.19mol), separates out wet pie white solid, stirred 60 minutes, suction filtration, in 80 ℃ of oven dry, 53 restrain products, yield 87%.m.p.181-183℃.IR：v＝3300，2942，2364，1710，1567，1413，1344，?1257，1186，843，785，742cm
-1.
1H?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
21H
36N
6O
6：C，53.83；H，7.74；N，17.94.Found：C，53.91；H，7.64；N，17.93.
Embodiment 4
In three mouthfuls of round-bottomed flasks of the 1000mL that magneton, reflux exchanger and thermometer are housed, add respectively sodium hydroxide (54g, 1.35mol), hexanolactam (114.13g, 1.01mol), 400mL water, start stir and temperature control in 70 ℃ of reactions 35 minutes.After reaction finishes, add cyanuric chloride (50.4g 0.27mol), is warming up to 70 ℃, kept 120 minutes, during with TLC monitoring reaction process, with ethanol as developping agent.Be cooled to 40 ℃, add concentration and be 36.5% concentrated hydrochloric acid (304g 3.04mol), separates out wet pie white solid, stirred 70 minutes, suction filtration, in 80 ℃ of oven dry, 51.78 restrain products, yield 85%.m.p.181-183℃.IR：v＝3300，2942，2364，1710，1567，1413，1344，1257，1186，843，785，742cm
-1.
1H?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
21H
36N
6O
6：C，53.83；H，7.74；N，17.94.Found：C，53.91；H，7.64；N，17.93.
Embodiment 5
In three mouthfuls of round-bottomed flasks of the 1000mL that magneton, reflux exchanger and thermometer are housed, add respectively sodium hydroxide (37.8g, 0.945mol), hexanolactam (91.53g, 0.81mol), 400mL water, start stir and temperature control in 70 ℃ of reactions 35 minutes.After reaction finishes, add cyanuric chloride (50.4g 0.27mol), is warming up to 70 ℃, kept 120 minutes, during with TLC monitoring reaction process, with ethanol as developping agent.Be cooled to 40 ℃, add concentration and be 36.5% concentrated hydrochloric acid (162g 1.62mol), separates out wet pie white solid, stirred 160 minutes, suction filtration, in 80 ℃ of oven dry, 51.66 restrain products, yield 84%.m.p.181-183℃.IR：v＝3300，2942，2364，1710，1567，1413，1344，1257，1186，843，785，742cm
-1.
1H?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
21H
36N
6O
6：C，53.83；H，7.74；N，17.94.Found：C，53.91；H，7.64；N，17.93.
After the preferred embodiment that describes in detail, being familiar with this technology personage can be well understood to, can carry out various variations and modification not breaking away under above-mentioned claim and the spirit, all foundations technical spirit of the present invention all belongs to the scope of technical solution of the present invention to any simple modification, equivalent variations and modification that above embodiment did.And the present invention also is not subjected to the restriction of the embodiment that gives an actual example in the specification sheets.
Claims (5)
1. one kind 2,4,6-three (hexosamine base)-1,3, the preparation method of 5-triazine is characterized in that in polar solvent, adopt " one kettle way ", make the carboxylate salt (II) of hexanolactam (I) open loop generation hexosamine earlier with alkali, and then substitution reaction takes place, separate out with hcl acidifying at last with cyanuric chloride (III);
2. the described preparation method of claim 1, wherein said polar solvent is a water.
3. the described preparation method of claim 1, wherein said alkali is sodium hydroxide.
4. the described preparation method of claim 1, wherein sodium hydroxide: hexanolactam: cyanuric chloride: the mol ratio of hydrochloric acid is 3-6: 3: 0.8-1: 3-9; The temperature of reaction 25-70 of hexanolactam hydrolysis ℃, reaction times 30-60 minute; The temperature of the carboxylate salt of hexosamine and cyanuric chloride generation substitution reaction is 25-80 ℃, reaction times 60-180 minute; The temperature of reaction of acid out is 25-50 ℃, and the reaction times is 30-180 minute.
5. preparation method as claimed in claim 4, wherein sodium hydroxide: hexanolactam: cyanuric chloride: the mol ratio of hydrochloric acid is 3.5: 3: 1: 3-9.
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250027A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine |
| CN102659701A (en) * | 2012-04-14 | 2012-09-12 | 修建东 | Synthesis of azacyclo-containing aminohexanoic acid |
| CN102659700A (en) * | 2012-03-05 | 2012-09-12 | 浙江金科过氧化物股份有限公司 | Production process of granular 2,4,6-tri(amino caproyl)-1,3,5-triazine having low chlorine content |
| CN102764610A (en) * | 2012-07-05 | 2012-11-07 | 陕西科技大学 | Chelating surfactants containing triazine rings and preparation method thereof |
| CN104213124A (en) * | 2014-09-04 | 2014-12-17 | 徐立庶 | Method for manufacturing water-based metal antirust agents |
| CN104649990A (en) * | 2013-11-26 | 2015-05-27 | 修建东 | Triazinyl triamine ethanol glutarate and preparation method thereof |
| CN104818077A (en) * | 2015-03-11 | 2015-08-05 | 洛阳绿帆功能化学有限公司 | Water-based antirust multifunctional additive with high hard water resistance, preparation method and application thereof |
| CN105732530A (en) * | 2016-01-28 | 2016-07-06 | 陕西省石油化工研究设计院 | 2,4,6-tri(amino acid)-1,3,5-triazine hydramine salts, and preparation method and application thereof |
| CN106146422A (en) * | 2016-08-16 | 2016-11-23 | 甘肃金盾化工有限责任公司 | A kind of production technology of 2,4,6 3 (amino caproyl) 1,3,5 triazine |
| CN108358862A (en) * | 2018-02-28 | 2018-08-03 | 大丰跃龙化学有限公司 | A kind of new 2,4,6- tri-（Aminocaproic Acid base）The synthetic method of -1,3,5- triazines |
| CN108912383A (en) * | 2018-07-20 | 2018-11-30 | 西能化工科技(上海)有限公司 | Superhigh temperature expandable thermoplastic microspheres and its application |
| CN110042397A (en) * | 2019-05-24 | 2019-07-23 | 南京工业大学 | A kind of water-based antirust agent and preparation method thereof |
| CN110638750A (en) * | 2019-10-28 | 2020-01-03 | 深圳市贝美药业有限公司 | Preparation method of desloratadine medicine and preparation thereof |
| CN111718306A (en) * | 2019-03-18 | 2020-09-29 | 南京工业大学 | Process for producing 2,4, 6-tri (aminocaproyl) -1,3, 5-triazine by one-pot method |
| CN114230536A (en) * | 2021-12-28 | 2022-03-25 | 诺泰生物科技(合肥)有限公司 | Triazine-nitrogen heterocyclic binary carboxylic acid-based waterborne antirust corrosion inhibitor and preparation method and application thereof |
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| US4402907A (en) * | 1980-08-13 | 1983-09-06 | Ciba-Geigy Corporation | Triazine carboxylic acids as corrosion inhibitors for aqueous systems |
| US6060580A (en) * | 1995-05-03 | 2000-05-09 | Dsm N. V. | Star-shaped branched polyamide |
| DE10208591A1 (en) * | 2002-02-27 | 2003-11-20 | Degussa | Crystallization of melamine tris-alkanoic acid for use, e.g., as corrosion inhibitor involves precipitation from alkaline aqueous solution by adding acid at elevated temperature |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250027B (en) * | 2011-05-16 | 2015-09-30 | 烟台恒迪克能源科技有限公司 | A kind of preparation method of 2,4,6-tri-(caproyl aminomethyl sulfo)-s-triazine |
| CN102250027A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine |
| CN102659700A (en) * | 2012-03-05 | 2012-09-12 | 浙江金科过氧化物股份有限公司 | Production process of granular 2,4,6-tri(amino caproyl)-1,3,5-triazine having low chlorine content |
| CN102659700B (en) * | 2012-03-05 | 2014-04-09 | 浙江金科过氧化物股份有限公司 | Production process of granular 2,4,6-tri(amino caproyl)-1,3,5-triazine having low chlorine content |
| CN102659701A (en) * | 2012-04-14 | 2012-09-12 | 修建东 | Synthesis of azacyclo-containing aminohexanoic acid |
| CN102764610A (en) * | 2012-07-05 | 2012-11-07 | 陕西科技大学 | Chelating surfactants containing triazine rings and preparation method thereof |
| CN102764610B (en) * | 2012-07-05 | 2013-12-18 | 陕西科技大学 | Chelating surfactants containing triazine rings and preparation method thereof |
| CN104649990A (en) * | 2013-11-26 | 2015-05-27 | 修建东 | Triazinyl triamine ethanol glutarate and preparation method thereof |
| CN104649990B (en) * | 2013-11-26 | 2018-01-16 | 烟台恒鑫化工科技有限公司 | A kind of triazine triamido glutaric acid alcohol amine salt and preparation method thereof |
| CN104213124A (en) * | 2014-09-04 | 2014-12-17 | 徐立庶 | Method for manufacturing water-based metal antirust agents |
| CN104818077B (en) * | 2015-03-11 | 2017-03-29 | 洛阳理工学院 | A kind of aqueous rustproof multifunction additive of anti-high hardness and its production and use |
| CN104818077A (en) * | 2015-03-11 | 2015-08-05 | 洛阳绿帆功能化学有限公司 | Water-based antirust multifunctional additive with high hard water resistance, preparation method and application thereof |
| CN105732530A (en) * | 2016-01-28 | 2016-07-06 | 陕西省石油化工研究设计院 | 2,4,6-tri(amino acid)-1,3,5-triazine hydramine salts, and preparation method and application thereof |
| CN106146422A (en) * | 2016-08-16 | 2016-11-23 | 甘肃金盾化工有限责任公司 | A kind of production technology of 2,4,6 3 (amino caproyl) 1,3,5 triazine |
| CN108358862A (en) * | 2018-02-28 | 2018-08-03 | 大丰跃龙化学有限公司 | A kind of new 2,4,6- tri-（Aminocaproic Acid base）The synthetic method of -1,3,5- triazines |
| CN108912383A (en) * | 2018-07-20 | 2018-11-30 | 西能化工科技(上海)有限公司 | Superhigh temperature expandable thermoplastic microspheres and its application |
| CN111718306A (en) * | 2019-03-18 | 2020-09-29 | 南京工业大学 | Process for producing 2,4, 6-tri (aminocaproyl) -1,3, 5-triazine by one-pot method |
| CN110042397A (en) * | 2019-05-24 | 2019-07-23 | 南京工业大学 | A kind of water-based antirust agent and preparation method thereof |
| CN110638750A (en) * | 2019-10-28 | 2020-01-03 | 深圳市贝美药业有限公司 | Preparation method of desloratadine medicine and preparation thereof |
| CN110638750B (en) * | 2019-10-28 | 2021-08-27 | 深圳市贝美药业有限公司 | Preparation method of desloratadine medicine and preparation thereof |
| CN114230536A (en) * | 2021-12-28 | 2022-03-25 | 诺泰生物科技(合肥)有限公司 | Triazine-nitrogen heterocyclic binary carboxylic acid-based waterborne antirust corrosion inhibitor and preparation method and application thereof |
| CN114230536B (en) * | 2021-12-28 | 2022-12-27 | 诺泰生物科技(合肥)有限公司 | triazine-N-heterocyclic dicarboxylic acid-based waterborne antirust corrosion inhibitor and preparation method and application thereof |
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Open date: 20110216 |