CN110317138A - A kind of preparation method of tetramethylethylenediamine - Google Patents
A kind of preparation method of tetramethylethylenediamine Download PDFInfo
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- CN110317138A CN110317138A CN201910689056.5A CN201910689056A CN110317138A CN 110317138 A CN110317138 A CN 110317138A CN 201910689056 A CN201910689056 A CN 201910689056A CN 110317138 A CN110317138 A CN 110317138A
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- paraformaldehyde
- tetramethylethylenediamine
- ethylenediamine
- organic solvent
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
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Abstract
The present invention provides a kind of preparation methods of tetramethylethylenediamine, comprising the following steps: paraformaldehyde is dissolved in organic solvent, obtains paraformaldehyde solution；In the presence of a catalyst and hydrogen, paraformaldehyde solution and ethylenediamine are subjected to methylation hydrogenation reaction, obtained reaction solution rectifying obtains tetramethylethylenediamine.The present invention dissolves paraformaldehyde using paraformaldehyde as raw material, with organic solvent, avoids using formalin, or avoids using dichloroethanes as the salt waste water of the reluctant sodium chloride-containing generated after raw material；The simple process, it is easy to operate, it is at low cost, and the yield of tetramethylethylenediamine is higher.Water content is 16.2~19.9% in crude product after reaction；Raw material ethylenediamine residual mass content is 0.15~0.23% in crude product, and the residual mass content of paraformaldehyde is 0.11~0.21%；The yield of tetramethylenthanediol is 96.1~98.3%；Purity is 99.37% or more.
Description
Technical field
The invention belongs to compound synthesis technical field more particularly to a kind of preparation methods of tetramethylethylenediamine.
Background technique
Tetramethylethylenediamine is mainly used as biochemical reagents, epoxy resin cross-linking agent, and prepares the centre of quaternary ammonium compound
The demand of body etc., market is bigger.
All the time, the production technology of tetramethylethylenediamine in the market is all using dichloroethanes and excessive dimethylamine
Then reaction carries out processing by excessive liquid alkaline and recycles excessive dimethylamine, steams the crude product of tetramethylethylenediamine, then pass through
Drying and dehydrating is crossed, product is obtained.The salt waste water of a large amount of sodium chloride-containing can be generated in the process, it is difficult to be handled.Secondly
It is exactly using liquid formaldehyde and reacting ethylenediamine, since product methylation number is more, the formalin amount needed is very
Greatly, it while also resulting in that the wastewater flow rate containing formaldehyde during post-reaction treatment is excessive, the clean manufacturing of country's proposition cannot be reached
It is required that.
Therefore, the new production work be badly in need of searching out that a kind of environmental pollution is small, and can produced in accordance with enterprise scale
Skill.
Summary of the invention
In view of this, this method can be kept away the purpose of the present invention is to provide a kind of preparation method of tetramethylethylenediamine
Exempt to generate a large amount of reluctant brine wastes, and the yield of tetramethylethylenediamine is higher.
The present invention provides a kind of preparation methods of tetramethylethylenediamine, comprising the following steps:
Paraformaldehyde is dissolved in organic solvent, paraformaldehyde solution is obtained；
In the presence of a catalyst and hydrogen, paraformaldehyde solution and ethylenediamine are subjected to methylation hydrogenation reaction, obtained
Reaction solution rectifying, obtains tetramethylethylenediamine.
Preferably, the preparation method of tetramethylethylenediamine, comprising the following steps:
Paraformaldehyde is dissolved in organic solvent, paraformaldehyde solution is obtained；
In the presence of a catalyst and hydrogen, paraformaldehyde solution and ethylenediamine are subjected to methylation hydrogenation reaction, obtained
Reaction solution rectifying, obtains tetramethylethylenediamine.
Preferably, the time of the heat preservation is 1~3 hour.
Preferably, the organic solvent is selected from one of methanol, ethyl alcohol, ethylenediamine and tetramethylethylenediamine or a variety of.
Preferably, the organic solvent be selected from methanol, ethyl alcohol, tetramethylethylenediamine, mass ratio 1:1~4:1 methanol and
The mixed solvent of the mixed solvent of ethylenediamine or the tetramethylethylenediamine of mass ratio 1:1~4:1 and ethylenediamine.
Preferably, the catalyst is selected from palladium-carbon catalyst.
Preferably, the temperature of the methylation hydrogenation reaction is 120~130 DEG C；The pressure for the hydrogenation reaction that methylates is 2.8
~3.2MPa.
Preferably, the mass ratio of the organic solvent, paraformaldehyde, ethylenediamine and catalyst be 1:1~9:0.95~
1.05:0.009~0.011.
Preferably, the paraformaldehyde solution is in a manner of being pumped into and reacting ethylenediamine；The speed being pumped into be 40g/h~
100g/h。
The present invention provides a kind of preparation methods of tetramethylethylenediamine, comprising the following steps: is dissolved in paraformaldehyde
In organic solvent, paraformaldehyde solution is obtained；In the presence of a catalyst and hydrogen, paraformaldehyde solution and ethylenediamine are subjected to first
Base hydrogenation reaction, obtained reaction solution rectifying, obtains tetramethylethylenediamine.The present invention is using paraformaldehyde as raw material, with organic
Solvent dissolves paraformaldehyde, avoids using formalin, or avoids using dichloroethanes from being difficult to locate as what is generated after raw material
The salt waste water of the sodium chloride-containing of reason；The simple process, it is easy to operate, it is at low cost, and the yield of tetramethylethylenediamine is higher, purity compared with
It is high.The results showed that water content is 16.2~19.9% in crude product after reaction；Raw material ethylenediamine residual mass content in crude product
It is 0.15%~0.23%, the residual mass content of paraformaldehyde is 0.11~0.21%；The yield of tetramethylenthanediol is
96.1~98.3%；Purity is 99.37% or more.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of tetramethylethylenediamine prepared by the embodiment of the present invention 1.
Specific embodiment
The present invention provides a kind of preparation methods of tetramethylethylenediamine, comprising the following steps:
Paraformaldehyde is dissolved in organic solvent, paraformaldehyde solution is obtained；
In the presence of a catalyst and hydrogen, paraformaldehyde solution and ethylenediamine are subjected to methylation hydrogenation reaction, obtained
Reaction solution rectifying, obtains tetramethylethylenediamine.
The present invention dissolves paraformaldehyde using paraformaldehyde as raw material, with organic solvent, avoids using formalin, or keep away
Exempt to use dichloroethanes as the salt waste water of the reluctant sodium chloride-containing generated after raw material；The simple process, it is easy to operate, at
This is low, and the yield of tetramethylethylenediamine is higher.
Paraformaldehyde is dissolved in organic solvent by the present invention, obtains paraformaldehyde solution.In the present invention, the poly
The molecular formula of formaldehyde is (HCHO)n, wherein the value of n is 8~100.
In the present invention, the organic solvent is preferably selected from one of methanol, ethyl alcohol, ethylenediamine and tetramethylethylenediamine
Or it is a variety of；The mixing for being more preferably selected from methanol, ethyl alcohol, tetramethylethylenediamine, the methanol of mass ratio 1:1~4:1 and ethylenediamine is molten
The in the mixed solvent of the tetramethylethylenediamine and ethylenediamine of agent and mass ratio 1:1~4:1 it is one or more.It is being embodied
In example, the organic solvent is selected from methanol, ethyl alcohol, tetramethylethylenediamine, the tetramethylethylenediamine of mass ratio 3:1 and ethylenediamine
The mixed solvent of the methanol and ethylenediamine of mixed solvent or mass ratio 3:1.If organic solvent is selected from ethylenediamine and/or tetramethyl second
When diamines, ethylenediamine is both reactant and solvent, and tetramethylethylenediamine is both reaction dissolvent and reaction product, reaction system
Substance is few, and reaction dissolvent is easy to recovery of applied, environment-protecting clean.
The paraformaldehyde is dissolved in organic solvent, is obtained paraformaldehyde solution and is specifically included:
Organic solvent is warming up to after 30~80 DEG C, paraformaldehyde is added, insulated and stirred dissolution is cooled to 20~25 DEG C, obtains
To paraformaldehyde solution.
Organic solvent is preferably warming up to 40~60 DEG C by the present invention, is more preferably warming up to 45~55 DEG C.The heat preservation when
Between preferably 1~3h.
After obtaining paraformaldehyde solution, the present invention in the presence of a catalyst and hydrogen, by the paraformaldehyde solution and second
Diamines carries out methylation hydrogenation reaction, and obtained reaction solution rectifying obtains tetramethylethylenediamine.In the present invention, the catalysis
Agent is preferably selected from palladium-carbon catalyst, is more preferably selected from 5% palladium-carbon catalyst.
The present invention carries out methylation hydrogenation reaction preferably in autoclave；It is described methylation hydrogenation reaction temperature be preferably
120~130 DEG C；The pressure for the hydrogenation reaction that methylates is preferably 2.8~3.2MPa.
In the present invention, main reaction in the methylation hydrogenation process are as follows:
NH2CH2CH2NH2+(HCHO)n+H2→(CH3)2NCH2CH2N(CH3)2+H2O；
Side reaction are as follows:
NH2CH2CH2NH2+(HCHO)n+H2→CH3NHCH2CH2NH2+H2O；
NH2CH2CH2NH2+(HCHO)n+H2→CH3NHCH2CH2NHCH3+H2O；
NH2CH2CH2NH2+(HCHO)n+H2→(CH3)2NCH2CH2NHCH3+H2O；
(HCHO)n+H2→CH3OH。
In the present invention, the mass ratio of the organic solvent, paraformaldehyde, ethylenediamine and catalyst is preferably 1:1~9:
0.95~1.05:0.009~0.011, more preferably 1:1~9:1:0.01.
The paraformaldehyde solution is in a manner of being pumped into and reacting ethylenediamine；The speed being pumped into is preferably 40g/h~100g/
H, more preferably 60g/h~80g/h；In a specific embodiment, the speed being pumped into is 70g/h.The time being pumped into is excellent
It is selected as 7~8 hours.
In order to further illustrate the present invention, below with reference to embodiment to a kind of system of tetramethylethylenediamine provided by the invention
Preparation Method is described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
200g methanol is weighed, temperature is raised to 45 DEG C, 130g paraformaldehyde is added, organic solvent is warming up to 45 DEG C of heat preservations 1
Hour, then stirring and dissolving is cooled to 20 DEG C~25 DEG C, obtains mixed liquor, as reaction raw materials for tetramethylethylenediamine
Synthetic reaction.60g ethylenediamine is added in autoclave, 5% palladium-carbon catalyst of 0.3g, nitrogen and hydrogen are replaced, is warming up to
Lead to hydrogen after 120 DEG C, pressure to 2.8~3.2Mpa is pumped into mixed liquor in autoclave, and being pumped into rate is 70g/h, methylation plus hydrogen
Reaction, after reaction, carries out rectifying, isolated tetramethylethylenediamine 114g, product content 99.64% for reaction solution.It surveys
Water content and feed stock conversion in system.Detection data is shown in Table 1.
The present invention carries out nuclear magnetic resonance spectroscopy test to tetramethylethylenediamine prepared by embodiment 1, as a result as Fig. 1, Fig. 1 are
The hydrogen nuclear magnetic resonance spectrogram of tetramethylethylenediamine prepared by the embodiment of the present invention 1.As can be seen from Figure 1: 1 rectifying of embodiment separation
Obtained product is tetramethylethylenediamine.
Embodiment 2
260g tetramethylethylenediamine is weighed, temperature is raised to 55 DEG C, 130g paraformaldehyde is added, organic solvent is warming up to 60
DEG C heat preservation 1 hour, then stirring and dissolving is cooled to 20 DEG C~25 DEG C, obtains mixed liquor, as reaction raw materials be used for tetramethyl second
The synthetic reaction of diamines.60g ethylenediamine, 5% palladium-carbon catalyst of 0.3g are added in autoclave, nitrogen and hydrogen are replaced, and are risen
Temperature is pumped into mixed liquor in pressure to 2.8~3.2MPa autoclave to hydrogen is led to after 120 DEG C, and being pumped into rate is 70g/h, methylation
Reaction solution is carried out rectifying, isolated tetramethylethylenediamine 371.8g, product content after reaction by hydrogenation reaction
99.43.Water content and feed stock conversion in survey system.Detection data is shown in Table 1.
Embodiment 3
150g tetramethylethylenediamine and the mixing of 50g ethylenediamine are weighed, temperature is raised to 45 DEG C, 130g paraformaldehyde is added,
Organic solvent is warming up to 45 DEG C and keeps the temperature 1 hour, then stirring and dissolving is cooled to 20 DEG C~25 DEG C, mixed liquor is obtained, as reaction
Raw material is used for the synthetic reaction of tetramethylethylenediamine.10g ethylenediamine, 5% palladium-carbon catalyst of 0.3g, nitrogen are added in autoclave
It is replaced with hydrogen, logical hydrogen after being warming up to 120 DEG C, pressure to 2.8~3.2Mpa, is pumped into mixed liquor in autoclave, is pumped into
Rate is 70g/h, and reaction solution is carried out rectifying, isolated tetramethylethylenediamine after reaction by methylation hydrogenation reaction
260g, product content 99.51%.Water content and feed stock conversion in survey system.Detection data is shown in Table 1.
Embodiment 4
150g methanol and 50g ethylenediamine are weighed, temperature is raised to 45 DEG C, 130g paraformaldehyde, organic solvent heating is added
1 hour is kept the temperature to 45 DEG C, then stirring and dissolving is cooled to 20 DEG C~25 DEG C, obtains mixed liquor, be used for tetramethyl as reaction raw materials
The synthetic reaction of base ethylenediamine.60g ethylenediamine is added in autoclave, 5% palladium-carbon catalyst of 0.3g, nitrogen and hydrogen are set
It changes, hydrogen is led to after being warming up to 120 DEG C, is pumped into mixed liquor in pressure to 2.8~3.2Mpa autoclave, being pumped into rate is 70g/h, first
Reaction solution is carried out rectifying, isolated tetramethylethylenediamine 112g, product content after reaction by base hydrogenation reaction
99.58%.Water content and feed stock conversion in survey system.Detection data is shown in Table 1.
Embodiment 5
200g ethyl alcohol is weighed, temperature is raised to 45 DEG C, 130g paraformaldehyde is added, organic solvent is warming up to 45 DEG C of heat preservations 1
Hour, then stirring and dissolving is cooled to 20 DEG C~25 DEG C, obtains mixed liquor, as reaction raw materials for tetramethylethylenediamine
Synthetic reaction.60g ethylenediamine is added in autoclave, 5% palladium-carbon catalyst of 0.3g, nitrogen and hydrogen are replaced, is warming up to
Lead to hydrogen after 120 DEG C, mixed liquor is pumped into pressure to 2.8~3.2Mpa autoclave, methylate hydrogenation reaction, after reaction,
Reaction solution is subjected to rectifying, isolated tetramethylethylenediamine 111.5g, product content 99.37%.Water content in survey system
And feed stock conversion.Detection data is shown in Table 1.
Comparative example 1
The dimethylamine agueous solution of 262.5g60% concentration is weighed, is added in autoclave, stirring is warming up to 80 DEG C, pressure
1MPa is pumped into 99g dichloroethanes, and control temperature is reacted at 80 DEG C, and insulation reaction 2 hours, is added after discharging after having pumped
220g40% liquid alkaline adjusts pH value, until strong basicity.Normal pressure steams product and unreacted dimethylamine, obtains 220g's aqueous 20%
Mixed liquor, residue are added the dilution of 100g tap water, obtain 461g brine waste.The mixture steamed is dried again by piece alkali,
Rectifying obtains 105g tetramethylethylenediamine, product content 99.44%.Water content and feed stock conversion in survey system.Examine data
It is shown in Table 1.
Water content and feed stock conversion in the system of 1 embodiment of the present invention 1~5 of table and comparative example 1
It can be seen that from 1 result of table, embodiment 1-5 is the technology of the present invention technique, and product yield is 96% or more, comparative example
1 is traditional handicraft, product yield 90.4%, therefore present invention process has obvious yield advantage, and present invention process crude product
Water content is few, and waste water is few.
As seen from the above embodiment, the present invention provides a kind of preparation methods of tetramethylethylenediamine, comprising the following steps:
Paraformaldehyde is dissolved in organic solvent, paraformaldehyde solution is obtained；In the presence of a catalyst and hydrogen, paraformaldehyde is molten
Liquid and ethylenediamine carry out methylation hydrogenation reaction, and obtained reaction solution rectifying obtains tetramethylethylenediamine.The present invention is with poly first
Aldehyde is raw material, dissolves paraformaldehyde with organic solvent, avoids using formalin, or avoid using dichloroethanes as raw material
The salt waste water of the reluctant sodium chloride-containing generated afterwards；The simple process, it is easy to operate, it is at low cost, and tetramethylethylenediamine
Yield is higher.The results showed that water content is 16.2~19.9% in crude product after reaction；Raw material ethylenediamine remains matter in crude product
Measuring content is 0.15%~0.23%, and the residual mass content of paraformaldehyde is 0.11~0.21%；The receipts of tetramethylethylenediamine
Rate is 96.1~98.3%；99.37% or more purity.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (9)
1. a kind of preparation method of tetramethylethylenediamine, which comprises the following steps:
Paraformaldehyde is dissolved in organic solvent, paraformaldehyde solution is obtained；
In the presence of a catalyst and hydrogen, the paraformaldehyde solution and ethylenediamine are subjected to methylation hydrogenation reaction, obtained
Reaction solution rectifying, obtains tetramethylethylenediamine.
2. preparation method according to claim 1, which is characterized in that the paraformaldehyde is dissolved in organic solvent, is obtained
It is specifically included to paraformaldehyde solution:
Organic solvent is warming up to after 30~80 DEG C, paraformaldehyde is added, insulated and stirred dissolution is cooled to 20~25 DEG C, obtains more
Polyformaldehyde solution.
3. preparation method according to claim 2, which is characterized in that the time of the heat preservation is 1~3 hour.
4. preparation method according to claim 1, which is characterized in that the organic solvent is selected from methanol, ethyl alcohol, ethylenediamine
With one of tetramethylethylenediamine or a variety of.
5. the preparation method according to claim 4, which is characterized in that the organic solvent is selected from methanol, ethyl alcohol, tetramethyl
The tetramethylethylenediamine of ethylenediamine, the mixed solvent of the methanol of mass ratio 1:1~4:1 and ethylenediamine or mass ratio 1:1~4:1
With the mixed solvent of ethylenediamine.
6. preparation method according to claim 1, which is characterized in that the catalyst is selected from palladium-carbon catalyst.
7. preparation method according to claim 1, which is characterized in that it is described methylation hydrogenation reaction temperature be 120~
130℃；The pressure for the hydrogenation reaction that methylates is 2.8~3.2MPa.
8. preparation method according to claim 1, which is characterized in that the organic solvent, paraformaldehyde, ethylenediamine and urge
The mass ratio of agent is 1:1~9:0.95~1.05:0.009~0.011.
9. preparation method according to claim 1, which is characterized in that the paraformaldehyde solution is in a manner of being pumped into and second
Diamine reactant；The speed being pumped into is 40g/h~100g/h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763295A (en) * | 2020-07-02 | 2020-10-13 | 安徽喜宝高分子材料有限公司 | Preparation method of epoxy resin curing agent |
| CN114933541A (en) * | 2022-06-10 | 2022-08-23 | 枣阳市福星化工有限公司 | Method for preparing 2-methylamino-5-chlorobenzophenone |
| CN115724747A (en) * | 2022-11-07 | 2023-03-03 | 华南理工大学 | Preparation method of ethylenediamine compound |
-
2019
- 2019-07-29 CN CN201910689056.5A patent/CN110317138B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| XIN GE等: "RANEY® nickel-catalyzed reductive N-methylation of amines with paraformaldehyde: theoretical and experimental study", 《RSC ADV.》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763295A (en) * | 2020-07-02 | 2020-10-13 | 安徽喜宝高分子材料有限公司 | Preparation method of epoxy resin curing agent |
| CN114933541A (en) * | 2022-06-10 | 2022-08-23 | 枣阳市福星化工有限公司 | Method for preparing 2-methylamino-5-chlorobenzophenone |
| CN114933541B (en) * | 2022-06-10 | 2024-05-03 | 枣阳市福星化工有限公司 | Method for preparing 2-methylamino-5-chlorobenzophenone |
| CN115724747A (en) * | 2022-11-07 | 2023-03-03 | 华南理工大学 | Preparation method of ethylenediamine compound |
| CN115724747B (en) * | 2022-11-07 | 2024-03-15 | 华南理工大学 | Preparation method of ethylenediamine compound |
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