CN108840831A - A kind of synthetic method of novel quaternary ammonium salt organic fire-retardant - Google Patents
A kind of synthetic method of novel quaternary ammonium salt organic fire-retardant Download PDFInfo
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- CN108840831A CN108840831A CN201810825287.XA CN201810825287A CN108840831A CN 108840831 A CN108840831 A CN 108840831A CN 201810825287 A CN201810825287 A CN 201810825287A CN 108840831 A CN108840831 A CN 108840831A
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- melamine
- ammonium salt
- quaternary ammonium
- organic fire
- retardant
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
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Abstract
The present invention relates to a kind of chemical synthesis process of novel quaternary ammonium salt organic fire-retardant, with melamine (MA) and 2,3- epoxypropyltrimethylchloride chloride (GTA) is raw material, 4- pyrollidinopyridine is catalyst, and the pH of deionized water is reacted and adjusted with dilute sulfuric acid in water phase.After the completion of reaction, post-treated, be refining to obtain melamine quaternary ammonium salt (MA/GTA), it is 41.5% that when pH=1, which reaches highest yield,.By the way that melamine quaternary ammonium salt obtained by the reacting of epoxy group on 2,3- epoxypropyltrimethylchloride chloride and the amino on melamine, decomposition temperature with higher can be used as a kind of organic fire-retardant.In addition melamine introduces activity functional groups through chemical modification, is of great significance to exploitation melamine application performance.
Description
Technical field：
The invention belongs to chemosynthesis technical fields, and in particular to the preparation method of melamine quaternary ammonium salt.
Background technique：
Melamine is a kind of organic fire-retardant, but dissolubility in water is very poor.And the function on melamine
Group only has amino, this limits the application of melamine to a certain extent.Currently, improving trimerization about using chemical means
The solubility property of cyanamide and the report for introducing functional group are fewer.For this purpose, we have proposed a kind of chemically synthesized methods to change
Into the correlated performance of melamine.
Summary of the invention
The purpose of the present invention is to provide a kind of simple processes, melamine season that is environmentally protective, being suitble to industrialized production
The preparation method of ammonium salt.It improves the solubility property of melamine and active group is introduced to melamine, improve melamine
The application performance of amine.
A kind of novel quaternary ammonium salt organic fire-retardant synthetic method of the invention, includes the following steps, melamine and 2,
The reaction of 3- epoxypropyltrimethylchloride chloride, 4- pyrollidinopyridine are catalyst, and addition adjusts the deionization of pH with dilute sulfuric acid
Water heating reflux reaction, reaction were refining to obtain melamine quaternary ammonium salt after 12 hours, i.e., a kind of novel quaternary ammonium salt is organic
Fire retardant.
Further, melamine and 2, the molar ratio of 3- epoxypropyltrimethylchloride chloride are 1:(wherein, melamine when 6
For 2g), the deionized water after adjusting pH value used is 130mL.
Further, the deionized water back flow reaction after adjusting pH value is added, reaction temperature is 90 DEG C, reaction time 12h.
As a further preference, the deionized water back flow reaction after adjusting pH value is added, catalyst 4- pyrollidinopyridine is used
Amount is every 100mL solvent 0.1g.
With melamine and 2,3- epoxypropyltrimethylchloride chloride is raw material, and synthetic route principle of the invention is as follows：
Detailed description of the invention
Fig. 1 is influence of the pH value to product yield.
Fig. 2 is melamine quaternary ammonium salt1H NMR figure.
Fig. 3 is the IR figure of melamine, 2,3- epoxypropyltrimethylchloride chloride, melamine quaternary ammonium salt.
Fig. 4 is the TG figure of melamine, 2,3- epoxypropyltrimethylchloride chloride, melamine quaternary ammonium salt；
Fig. 5 is the DTG figure of melamine, 2,3- epoxypropyltrimethylchloride chloride, melamine quaternary ammonium salt.
Specific embodiment
Below with reference to one embodiment, the chemical synthesis process of melamine quaternary ammonium salt provided by the invention is carried out detailed
Explanation.
Embodiment
The chemical synthesis process of the melamine quaternary ammonium salt of the present embodiment, includes the following steps：
(1) it is 90 DEG C, reaction time 12h that experiment, which starts the temperature of control reaction, is added by the catalyst of every 100mL solvent 0.1g
Enter 4- pyrollidinopyridine.Mol ratio is 1 in experiment：3,1：4,1：5,1：6, and suitable deionized water conduct is added and urges
Agent.It finds that its yield is no more than 10% after experiment, is found after reaction mixture is cooling, 1：Reaction solution when 6
The precipitating of precipitation is minimum, illustrates the progress for being more advantageous to reaction；
(2) in molar ratio 1：6 weigh melamine and 2,3- epoxypropyltrimethylchloride chloride (wherein, melamine 2g).It will
Melamine is added in 500ml three-necked flask, and 2,3- epoxypropyltrimethylchloride chlorides are put into beaker, is measured and is adjusted with graduated cylinder
The deionized water 130mL of good pH makees solvent.Partial solvent is dissolved into 2,3- epoxypropyltrimethylchloride chloride, another part solvent
It pours into three-necked flask；
(3) catalyst for pressing every 100mL solvent 0.1g, weighs 4- pyrollidinopyridine in three-necked flask.Three-necked flask is pressed from both sides
In thermostat water bath, adjusting reaction temperature is 90 DEG C, erects agitating device and condensation reflux unit.After stirring 15min, it is added
2,3- epoxypropyltrimethylchloride chloride reactant aqueous solution 12h；
(4) after reaction, reaction mixture is cooling, filtering, then carry out vacuum distillation and remove most solvents.It will concentration
Liquid filters again, is later put into the concentrate of filtering in 80 DEG C of baking oven and water is gone to obtain thick liquid as far as possible, is added suitable
The stirring of amount n-butanol, immersion 1h obtain white paste.Then suitable ethyl alcohol dissolution dispersion paste is added, adds half
The ethyl acetate of volume obtains white powder and is scattered in solvent, and stratification removes supernatant.Add 1:1 volume ratio
The washing of the mixed liquor of ethyl alcohol and ethyl acetate, stratification remove supernatant.It dries in 60 DEG C of baking ovens to constant weight, obtains white
Color powder weighs, and calculates yield.
Test result is as follows through Nuclear Magnetic Resonance for molecular structure of compounds in the present embodiment：
1H NMR(D2O), δ (ppm) 3.109 (s, 9), 3.185-3.461 (m, 4), 3.896-3.958 (m, 1), 4.409-
4.418(s,1).
Test result is as follows through infrared spectrometer for molecular structure of compounds in the present embodiment：
IR (KBr), σ (cm-1):2960,1640,1480,1130,930,3466,3417,1560.
The chemical synthesis process simple possible of melamine quaternary ammonium salt, without cumbersome post-processing, and also it is environmentally friendly
Pollution-free, process flow is easy to implement, realizes the industrialized production of product.
Claims (5)
1. a kind of synthetic method of novel quaternary ammonium salt organic fire-retardant, it is characterised in that melamine and 2,3- glycidyl three
Ammonio methacrylate reaction, 4- pyrollidinopyridine are catalyst, and addition is heated to reflux instead with the deionized water that dilute sulfuric acid adjusts pH
It answers, reaction was refining to obtain melamine quaternary ammonium salt after 12 hours.
2. a kind of synthetic method of novel quaternary ammonium salt organic fire-retardant according to claim 1, it is characterised in that trimerization
The molar ratio of cyanamide and 2,3- epoxypropyltrimethylchloride chloride is 1:When 6, wherein melamine 2g, adjusting pH used
Deionized water after value is 130mL.
3. a kind of synthetic method of novel quaternary ammonium salt organic fire-retardant according to claim 1, it is characterised in that be added
Deionized water back flow reaction after adjusting pH value, reaction temperature are 90 DEG C.
4. a kind of synthetic method of novel quaternary ammonium salt organic fire-retardant according to claim 1, it is characterised in that be added
Deionized water back flow reaction after adjusting pH value, reaction time 12h.
5. a kind of synthetic method of novel quaternary ammonium salt organic fire-retardant according to claim 1, it is characterised in that be added
Deionized water back flow reaction after adjusting pH value, catalyst 4- pyrollidinopyridine dosage are every 100mL solvent 0.1g.
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| CN201810825287.XA CN108840831B (en) | 2018-07-25 | 2018-07-25 | Synthesis method of novel quaternary ammonium salt organic flame retardant |
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| CN108840831B CN108840831B (en) | 2021-07-30 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111635339A (en) * | 2020-06-02 | 2020-09-08 | 安徽理工大学 | Quaternary ammonium type guanidine sulfonate, and preparation method and application thereof |
| CN112744811A (en) * | 2021-02-07 | 2021-05-04 | 李永锋 | Large-sheet-diameter graphene oxide and preparation method thereof |
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| CN111635339A (en) * | 2020-06-02 | 2020-09-08 | 安徽理工大学 | Quaternary ammonium type guanidine sulfonate, and preparation method and application thereof |
| CN111635339B (en) * | 2020-06-02 | 2023-04-14 | 安徽理工大学 | Quaternary ammonium type guanidine sulfonate, and preparation method and application thereof |
| CN112744811A (en) * | 2021-02-07 | 2021-05-04 | 李永锋 | Large-sheet-diameter graphene oxide and preparation method thereof |
| CN112744811B (en) * | 2021-02-07 | 2023-01-17 | 常州精瑞斯新材料科技有限公司 | Large-sheet-diameter graphene oxide and preparation method thereof |
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| CN108840831B (en) | 2021-07-30 |
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