CN100591659C - A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor - Google Patents
A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor Download PDFInfo
- Publication number
- CN100591659C CN100591659C CN200610154984A CN200610154984A CN100591659C CN 100591659 C CN100591659 C CN 100591659C CN 200610154984 A CN200610154984 A CN 200610154984A CN 200610154984 A CN200610154984 A CN 200610154984A CN 100591659 C CN100591659 C CN 100591659C
- Authority
- CN
- China
- Prior art keywords
- pipeline reactor
- dimethylamine
- reactor
- ethylene diamine
- tetramethyl ethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesizing method of N,N,N',N'-methyl ethanediamine, which comprises the following steps: adopting 1, 2-dichloroethane, sodium hydroxide solution and dimethylamine as raw material with the molar rate at 1.000:1.025:2.500-1.000:1.025:20.000; reacting in the pipe reactor under 0.1-2.0Mpa at 100-250 Deg C for 5-30min; setting the molar rate of 1, 2-dichloroethane and solvent at 1: 1-1: 10; rectifying the N,N,N',N'-methyl ethanediamine solution; separating dimethylamine from solvent; circulating solvent; rectifying again to obtain the product.
Description
Technical field
The present invention relates to a kind of chemical synthesis process, particularly a kind of pipeline reactor that utilizes synthesizes N, N, N ', the method for N '-Tetramethyl Ethylene Diamine.
Background technology
N,N,N (another name:, also be the quaternary ammonium compound intermediate Tetramethyl Ethylene Diamine) mainly as biochemical reagents, epoxy resin cross-linking agent.
This material can utilize Eschweiler, W.-Clark, and the H.T synthesis method is produced, and this also is that the most traditional method promptly is total to heat with quadrol with formaldehyde, excessive formic acid, and the N-methylation reaction can take place, and generates N, N, N ', N '-Tetramethyl Ethylene Diamine.
H
2NCH
2CH
2NH
2+4HCHO+4HCOOH→(H
3C)
2NCH
2CH
2N(CH
3)
2+4CO
2+4H
2O
Though this method synthesis condition is relatively gentleer, can produce at normal temperatures and pressures, maximum shortcoming is that yield is too low.This is because this method is bad to the selectivity of want product, product in synthetic is the mixture of monomethyl quadrol, dimethyl-ethylenediamine, trimethylammonium quadrol and Tetramethyl Ethylene Diamine, and the boiling point of these four products differs very little, also is difficult to separate in industrial method with rectifying.And reaction finishes the excessive acid in back will be with a large amount of alkaline purifications, and disposal of pollutants is serious.
United States Patent (USP) U.S.Pat.No 5,811,584 has reported another kind of synthetic N, N, N ', the method for N '-Tetramethyl Ethylene Diamine, utilize 2,3-dimethyl-2,3-dinitrobenzene butane shortening obtains product N, N, N ', N '-Tetramethyl Ethylene Diamine, this reacts with methylethylketone as solvent, under the catalysis of Reynolds cobalt, carry out
Summary of the invention
At the problem that prior art exists, the invention provides that a kind of cost is low, yield is high, easy-operating N, N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine.
For reaching above purpose, the present invention realizes by such technical scheme: provide a kind of N, N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine, with 1,2-ethylene dichloride, sodium hydroxide solution and dimethylamine are raw material, under the solvent existence condition, reacting a step in pipeline reactor makes product N, N, N ', N '-Tetramethyl Ethylene Diamine.1,2-ethylene dichloride: sodium hydroxide: dimethylamine=1.000: 1.025: 2.500～1.000: 1.025: 20.000 (ratio of amount of substance), 1,2-ethylene dichloride and solvent=1: 1～1: 10 (ratio of quality).Reaction solvent can be methyl alcohol, ethanol, benzene or toluene.Raw material and solvent are squeezed in the pipeline reactor according to material proportion with volume pump, and the system pressure in pipeline reactor is 0.1～2.0Mpa, and temperature is 100～250 ℃, 5～30 minutes residence time.To gained N, N, N ', N '-Tetramethyl Ethylene Diamine solution carries out rectifying, and dimethylamine and solvent are split, and solvent cycle is used, and rectifying promptly gets product once more.
Dimethylamine of the present invention can be the pure dimethylamine or the aqueous solution, and the concentration of the aqueous solution is 10～50%.
Pipeline reactor of the present invention is a kind of novel reactor that adopts the static mixing technology, and the different fluid that enters pipeline is well mixed, and its internals is to make of thinner tubing.Tubule inside can lead to heating agent or refrigerant, so it has the characteristic of the mixing and two aspects of conducting heat simultaneously.It not only can the realization response process serialization, and can in time take away a large amount of heats that reaction process produces, thereby guarantee that temperature of reaction is unlikely to too high.
With synthetic N of the present invention, N, N ', the effect that N '-Tetramethyl Ethylene Diamine is useful is:
At first, present method has adopted pipeline reactor, can make of low pressure or normal pressure being originally that highly compressed reacts, and compares the following advantage of performance with traditional tank reactor:
1. compare with tank reactor, the security of static mixer formula pipeline reactor is fabulous.Compare with tank reactor, the material lagging amount of static mixer formula pipeline reactor is much smaller, and many urgent discharge valves can be installed on the pipeline reactor, just in case the temperature of reactor or pressure surpass the maximum value that allows, urgent discharge valve is opened immediately automatically, danger is dropped to minimum.
2. be used for the chemical reaction process under the condition of high voltage, the still wall of tank reactor and flange are all very thick, invest also very big.Along with the increase of tank reactor volume, investment is risen especially significantly.By contrast, the investment of static mixer formula pipeline reactor economizes, and industrial scale is big more, and the ratio of saving is also just big more.
3. say from management view that the tank reactor that is used for chemical reaction process under the condition of high voltage must manage according to the relevant regulations of pressurized vessel, and pipeline reactor only requires that the relevant regulations according to pressure pipeline manage.
4. in tank reactor, the back-mixing of material is very severe, and in static mixer formula pipeline reactor, because the mobile piston flow (plug flow) that is similar to of material, so material back-mixing seldom.For some chemical reaction process, the back-mixing of material will cause the aggravation of side reaction, and the aggravation of side reaction will cause increasing of by product, finally influences the yield of product.
5. tank reactor is generally speaking as periodical operation, and several reactor series connection also can realize operate continuously.The reactor series connection realizes operate continuously, and not only trouble but also equipment volume Pang are big.Static mixer formula pipeline reactor realizes easily that not only operate continuously but also equipment volume are little by contrast.
6. except the stirring tank of magnetic force driving, difficulty is all compared in general stirring tank sealing, and leakage phenomenon takes place sometimes.Static mixer formula pipeline reactor connects with flange, does not have moving parts, and sealing property is fine, can not leak, and helps environment protection, can accomplish to carry out production strictly in line with rules and regulations.
Secondly, present method has that raw material is cheap and easy to get, and production cost is low, and disposal of pollutants is few, and technology is simple, realizes suitability for industrialized production easily, yield height advantages such as (reaching as high as 90%).
Description of drawings:
Fig. 1 is the pipeline reactor that uses of the present invention and the wiring layout of mixing tank;
Description of reference numerals: threeway sparger 1, static mixer 2, bend pipe 3, chuck 4, mixture intake N1, mixture outlet N2, chuck import N3, Jacket outlet N4, temperature-measuring port N5, pressure tap N6, thief hole N7, pump entry N8.
Embodiment:
Below in conjunction with embodiment the present invention is further described, embodiment will help to understand the present invention better, but the present invention is not limited only to following embodiment.
Pipeline reactor of the present invention is a kind of novel reactor that adopts the static mixing technology, and the different fluid that enters pipeline is well mixed, and its internals is to make of thinner tubing.Tubule inside can lead to heating agent or refrigerant, so it has the characteristic of the mixing and two aspects of conducting heat simultaneously.It not only can the realization response process serialization, and can in time take away a large amount of heats that reaction process produces, thereby guarantee that temperature of reaction is unlikely to too high.Its member and explanation are referring to following Fig. 1 explanation.
The visible threeway sparger 1 from the figure bottom, two media is entered (if the operational characteristic of medium is special by mixture intake N1 respectively, need to design especially sparger so), the back pipeline reactor is in series by many groups of static mixers 2 usually, can connect with common taper(ed)pipe between each group, also can connect, discharge by mixture outlet N2 with bend pipe 3.Static mixer 2 can also be provided with chuck 4, and chuck import N3 and Jacket outlet N4 are arranged on the chuck 4.On bend pipe 3, be provided with temperature-measuring port N5, also be provided with pressure tap N6 on the static mixer 2, thief hole N7, pump entry N8.Each group static mixer is all formed by two sections, and the front is that the mixing section back is a conversion zone.Mixing section select generally speaking to adapt static mixer and nominal diameter is smaller, and such static mixer has very good dispersion/mixed performance.Mixing section makes reaction mass disperse separately well to be mixed with each other, and excellent contact has guaranteed that reaction process can carry out smoothly.But because the nominal diameter of mixing section is smaller, in mixing section the residence time of material shorter, often can not provide the enough reaction times, so be provided with conversion zone.Static mixer formula pipeline reactor adopts the JHF type bigger as conversion zone and nominal diameter, and conversion zone provides the enough reaction times.Different with its alloytype, JHF type static mixer is made internal element with tubule, and it can not only make the material intermingling that flows through, and very big specific volume heat transfer area also is provided.The inside tubule of JHF type feeds heat-eliminating medium, just can take away a large amount of heats that reaction process produces, also can feed heating medium, for reaction process provides heat to the inside of JHF type tubule, if the exothermic heat of reaction amount is little, it is just passable directly to add chuck on mixing section.
Embodiment 1: a kind of N, and N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine, reaction process is as follows:
Get 1,2-ethylene dichloride 989.7g (1mol), sodium hydroxide 410g, dimethylamine 4508g (10mol), benzene 1950g.Reactor adopts pipeline reactor, and volume pump is adopted in charging.Keeping reactor jacket temperature is 180 ℃, regulates flow, divides two groups to squeeze into simultaneously in the pipeline reactor above raw material, system pressure 0.82Mpa, reaction time 10 minutes.Liquid is synthesized in rectifying, and 119～121 ℃ of cuts of extraction get product 1005g, yield 86.50%.
Embodiment 2: a kind of N, and N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine, reaction process is as follows:
Get 1,2-ethylene dichloride 989.7g (1mol), sodium hydroxide 410g, dimethylamine 3606g (8mol), toluene 1800g.Reactor adopts pipeline reactor, and volume pump is adopted in charging.Keeping reactor jacket temperature is 150 ℃, regulates flow, divides two groups to squeeze into simultaneously in the pipeline reactor above raw material, system pressure 0.68Mpa, reaction time 8 minutes.Liquid is synthesized in rectifying, and 119～121 ℃ of cuts of extraction get product 1018g, yield 87.60%.
Embodiment 3: a kind of N, and N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine, reaction process is as follows:
Get 1,2-ethylene dichloride 989.7g (1mol), sodium hydroxide 410g, dimethylamine 2704g (6mol), methyl alcohol 1500g.Reactor adopts pipeline reactor, and volume pump is adopted in charging.Keeping reactor jacket temperature is 120 ℃, regulates flow, divides two groups to squeeze into simultaneously in the pipeline reactor above raw material, system pressure 0.46Mpa, reaction time 12 minutes.Liquid is synthesized in rectifying, and 119～121 ℃ of cuts of extraction get product 1048g, yield 90.10%.
Embodiment 4: a kind of N, and N, N ', the synthetic method of N '-Tetramethyl Ethylene Diamine, reaction process is as follows:
Get 1,2-ethylene dichloride 98.97g (1mol), sodium hydroxide 410g, massfraction are 33% dimethylamine agueous solution 6830g (5mol), ethanol 1200g.Reactor adopts pipeline reactor, and volume pump is adopted in charging.Keeping reactor jacket temperature is 100 ℃, regulates flow, divides two groups to squeeze into simultaneously in the pipeline reactor above raw material, system pressure 0.20Mpa, reaction time 20 minutes.Liquid is synthesized in rectifying, and 119～121 ℃ of cuts of extraction get product 1030g, yield 88.10%.
It is also noted that at last what more than enumerate only is a specific embodiment of the present invention.Obviously, the invention is not restricted to above embodiment, a lot of distortion can also be arranged.Those of ordinary skill in the art can go out all distortion from direct derivation of content disclosed by the invention or association, all thinks protection scope of the present invention.
Claims (4)
1, a kind of pipeline reactor that utilizes synthesizes N, N, and N ', the method for N '-Tetramethyl Ethylene Diamine is characterized in that:
With 1,2-ethylene dichloride, sodium hydroxide solution and dimethylamine are raw material, under the solvent existence condition, in JHF type static mixer pipeline reactor, react one the step make product N, N, N ', N '-Tetramethyl Ethylene Diamine; In pipeline reactor, system pressure is 0.1～2.0Mpa, temperature is 100～250 ℃, 5～30 minutes residence time, 1,2-ethylene dichloride: sodium hydroxide: the ratio of the amount of substance of dimethylamine is=1.000: 1.025: 2.500～1.000: 1.025: 20.000, and 1, the mass ratio of 2-ethylene dichloride and solvent is 1: 1～1: 10.
2, the pipeline reactor that utilizes according to claim 1 synthesizes N, N, and N ', the method for N '-Tetramethyl Ethylene Diamine is characterized in that:
Described dimethylamine is the pure dimethylamine or the aqueous solution, and the concentration of the aqueous solution is 10～50%.
3, the pipeline reactor that utilizes according to claim 1 synthesizes N, N, and N ', the method for N '-Tetramethyl Ethylene Diamine is characterized in that:
Described solvent is methyl alcohol, ethanol, benzene or toluene.
4, the pipeline reactor that utilizes according to claim 1 synthesizes N, N, and N ', the method for N '-Tetramethyl Ethylene Diamine is characterized in that:
Described pipeline reactor comprises that is used for the threeway sparger (1) that two media enters respectively, the back pipeline reactor is in series by many groups of JHF type static mixers (2), connect with bend pipe (3) between each group, static mixer (2) is provided with chuck (4).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200610154984A CN100591659C (en) | 2006-11-29 | 2006-11-29 | A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200610154984A CN100591659C (en) | 2006-11-29 | 2006-11-29 | A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1962606A CN1962606A (en) | 2007-05-16 |
| CN100591659C true CN100591659C (en) | 2010-02-24 |
Family
ID=38081854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200610154984A Active CN100591659C (en) | 2006-11-29 | 2006-11-29 | A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100591659C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012164B (en) * | 2012-12-26 | 2014-12-31 | 上海安诺芳胺化学品有限公司 | Method for continuously producing m-diethylaminophenol through channelization |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1410416A (en) * | 2002-11-13 | 2003-04-16 | 南京红宝丽股份有限公司 | Production method of isopropanolamine |
| CN1594279A (en) * | 2004-06-29 | 2005-03-16 | 浙江大学 | Process and apparatus for producing o-phenylenediamine |
-
2006
- 2006-11-29 CN CN200610154984A patent/CN100591659C/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1410416A (en) * | 2002-11-13 | 2003-04-16 | 南京红宝丽股份有限公司 | Production method of isopropanolamine |
| CN1594279A (en) * | 2004-06-29 | 2005-03-16 | 浙江大学 | Process and apparatus for producing o-phenylenediamine |
Non-Patent Citations (2)
| Title |
|---|
| 关于卤代烷与氨反应制备胺的方程式. 蒋达荣.内江师范学院学报，第17卷第4期. 2002 |
| 关于卤代烷与氨反应制备胺的方程式. 蒋达荣.内江师范学院学报，第17卷第4期. 2002 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1962606A (en) | 2007-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104693038B (en) | A kind of method and its device for preparing propane diamine as raw material using propane diols and liquefied ammonia | |
| CN103936559B (en) | The method of continuous prodution Resorcinol | |
| CN105107442A (en) | Intelligent industrialized micro-channel flow reactor | |
| CN107501042B (en) | Method for preparing isopropanol by hydrolyzing isopropyl acetate | |
| CN100591659C (en) | A method for synthesizing N, N, N', N'-tetramethylethylenediamine by utilizing a pipeline reactor | |
| CN102276479A (en) | Method and device for producing p-phenylenediamine by using liquid phase continuous hydrogenation method | |
| CN101497572A (en) | Method for producing tert-butylamine based on coupling reaction-separation | |
| CN106892790B (en) | Method for preparing deuterated aniline compound by using microchannel reaction device | |
| CN205164690U (en) | Intelligence industrialization microchannel continuous reactor | |
| CN113877494A (en) | Multifunctional flowing microtube reaction device and operation method | |
| CN110026134A (en) | A method of series connection and prepares methanol using it at synthetic tower | |
| CN110862293A (en) | Continuous method for preparing dihalogenated alkane from diol compound | |
| CN109896996A (en) | Organic carboxyl acid is continuously synthesizing to method | |
| CN1962607A (en) | Method for synthesizing allylamine using transfer line reactor | |
| CN101104580B (en) | Production method for continuous synthesizing vinylmethylketone by one-step and device thereof | |
| CN213032467U (en) | Industrial multifunctional micro-channel reactor production system | |
| CN112979476B (en) | Process for producing mixed phenylenediamine | |
| WO2021227137A1 (en) | External micro-interface strengthening system and method for preparing cyclohexanone by esterification method | |
| CN202099218U (en) | Device for producing ursol by liquid phase continuous hydrogenation method | |
| CN112430188A (en) | Method for preparing isopropyl aniline by novel hydrogenation technology | |
| CN111744452A (en) | 2-chlorobenzoic acid continuous flow synthesis device and method for synthesizing 2-chlorobenzoic acid | |
| CN101817752A (en) | Preparation method of 1, 3-propanediamine | |
| CN218654350U (en) | Micro-channel reactor for producing paranitroaniline | |
| CN211303052U (en) | Cyclopentadiene dimerization reaction device | |
| CN104418696A (en) | Method for synthesizing PVC (Polyvinyl Chloride) or vinyl acetate by taking CO or methanol as raw material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180605 Address after: 311607 No. 909 Xin'An River Road, Yangxi street, Jiande, Hangzhou, Zhejiang Co-patentee after: Jiangsu Xinhua Chemical Co., Ltd. Patentee after: Zhejiang Xinhua Chemical Co., Ltd. Address before: 311600 90 Jiande Road East Xin'An River Road, Hangzhou, Zhejiang Patentee before: Xincheng Chemistry Co., Ltd., Hangzhou |
|
| TR01 | Transfer of patent right |