CN105198754A - Method for preparing N,N-dimethyl-1,3-diaminopropane - Google Patents
Method for preparing N,N-dimethyl-1,3-diaminopropane Download PDFInfo
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- CN105198754A CN105198754A CN201510584409.7A CN201510584409A CN105198754A CN 105198754 A CN105198754 A CN 105198754A CN 201510584409 A CN201510584409 A CN 201510584409A CN 105198754 A CN105198754 A CN 105198754A
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- propylene diamine
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Abstract
The invention relates to a method for preparing N,N-dimethyl-1,3-diaminopropane. The method comprises the steps that acrylonitrile is added into a synthesis kettle, and dimethylamine is added and then removed through decompressing rectifying to prepare N,N-dimethyl amine acrylonitrile; a hydrogenation catalyst is added, liquid ammonia is introduced into the high-pressure kettle, hydrogen is introduced, reacting is performed, settling is performed, then prefractionation is performed, and rectifying is performed to obtain the N,N-dimethyl-1,3-diaminopropane. According to the method for preparing the DMAPA, the technology is simple, improvement of the selectivity is guaranteed, the yield per unit of double slag is greatly decreased, and a large amount of dangerous waste treatment charge is saved; consumption of the raw materials of the acrylonitrile and the dimethylamine is reduced, the raw material consumption cost of a DMAPA synthesis device is saved, that is, the production cost is saved, and the enterprise benefits are increased.
Description
Technical field
The invention belongs to field of fine chemical, relate to one and prepare N, the method for N-dimethyl-1,3-propylene diamine.
Background technology
Diamines is the important chemical substance of a class, and be widely used as raw material, intermediate or product, such as diamines is the important feature unit in synthesizing polyamides process and in other polycondensations.
N, N-dimethyl-1,3-propylene diamine (DMAPA) is a kind of important intermediate, prepared by the industry for such as lubricant, and in addition, DMAPA is as the raw material preparing setting accelerator, and itself should have antiseptic property.
The synthetic method of patent CN102617356A to DMAPA is summarized, but different with domestic production synthetic method.Major cause is domestic main to produce for the purpose of DMAPA, and the synthetic method that this patent provides is effectively to utilize for the purpose of corresponding nitrile raw material.
At present, the production technique of domestic main flow is vinyl cyanide and dimethylamine synthesis N, N-dimethyl propionitrile, again by N, N-dimethyl propionitrile is solvent, also be raw material, at the temperature examined and appropriate liquefied ammonia as under inhibitor, under the effect of Raney's nickel catalyst, high-pressure hydrogenation prepares thick propylene diamine, and current domestic propionitrile prepares the selectivity of propylene diamine at 95-96%, the heavy constituent impurity of 2-3% is wherein had to produce, make domestic DMAPA device produce a large amount of heavy slags every year and need process, for professional production propylene diamine device beyond doubt one very worried and have and waste raw material and the problem of production cost, Some Enterprises is made to have to reclaim secondary amine, but due to the ratio of secondary amine very low, heavy slag viscosity is larger, reclaim separating difficulty very large, need extra increase Technical investment and set up rectifying device to reclaim, greatly increase investment and the production operating cost of DMAPA device.
Summary of the invention
The object of the invention is in order to solve existing DMAPA synthesizer produce every year a large amount of heavy slags need process, not only waste raw material but also increase the defect of production and operation product basis and provide one to be convenient to large-scale industry preparation, and in preparation process, effectively improve the selectivity that propionitrile prepares DMAPA, reduce synthesis material, especially the consumption of vinyl cyanide, also the content of secondary amine in product is greatly reduced, avoid in product containing too much heavy slag, reduce the investment of DMAPA and apparatus for converting and the preparation N of production operating cost, the method of N-dimethyl-1,3-propylene diamine.
To achieve these goals, the present invention is by the following technical solutions:
One prepares N, and the method for N-dimethyl-1,3-propylene diamine, said method comprising the steps of:
A) vinyl cyanide is joined in synthesis reactor, control temperature 120-140 DEG C, under the condition of stirring, cooling water circulation cooling, add dimethylamine, remove dimethylamine through rectification under vacuum and obtain N, N-dimethylaminopropionitrile;
B) by the N that step a) is obtained, N-dimethylaminopropionitrile adds autoclave, adds hydrogenation catalyst, in autoclave, pass into liquefied ammonia, be warming up to 80-95 DEG C, pressure remains on 2.5-3MPa, pass into hydrogen, stir and keep temperature 80-95 DEG C simultaneously, reaction, fore-running after sedimentation, rectifying obtains N, N-dimethyl-1,3-propylene diamine, then basin packaging.In the technical program, nitrile reactive chemistry equation processed: (CH
3)
2nH+CH
2=CHCN → (CH
3)
2nCH
2cH
2cN
Hydrogenation reaction chemical equation: (CH
3)
2nCH
2cH
2cN+2H
2→ (CH
3)
2nCH
2cH
2cH
2nH
2
Side reaction: CH
2=CHCN+3H
2→ CH
3cH
2cH
2nH
2.
As preferably, in step a), the mol ratio of vinyl cyanide and dimethylamine is 1:1.
As preferably, the mol ratio of hydrogenation catalyst and N, N-dimethyl propionitrile is 10:1.
As preferably, during fore-running, temperature is greater than the cut feeding rectifying of 134 DEG C.
As preferably, the preparation method of hydrogenation catalyst is as follows: take 65-70 part Ni, 55-60 part Al and 10-12 part supplementary additive by weight, cool after melting at 3200-3300 DEG C, pulverize 300-400 mesh sieve and obtain powdered alloy, powdered alloy is activated in alkali lye, apply the magnetic field of 1.5-1.8T while activation in outside, then washing to pH value is 10.2-11.3, and products therefrom is hydrogenation catalyst.
In the technical program, the high catalytic activity of Raney's nickel comes from the catalytic property of nickel itself and the structure of its porous, and namely vesicular structure stems from the aluminium in strong caustic removing alumel, this process is called as leaching, and the Leaching reaction after simplification is as follows:
2Al+2NaOH+6H2O→2Na[Al(OH)4]+3H2
Because Leaching reaction brings the activity of catalyzer, the hydrogen storage simultaneously produced has been entered in catalyzer, therefore is also referred to as activation.The surface-area of finished product is measured by the adsorption experiment of gas (as hydrogen) usually.Experiment finds that nearly all contact area all also exists nickel.The average nickel contact area of business-like Raney's nickel is 100 ㎡/g.
As preferably, described supplementary additive is Graphene, nano titanium oxide, lanthanum trioxide or nano silicon.In the technical program, the existence of supplementary additive is active in order to improve to Raney's nickel, because the active height of Raney's nickel is relevant with the quantity of Active sites, active centre surface density large person catalytic activity is high, and the material that supplementary additive Selection radio surface-area is large, Active sites quantity is increased, thus improve the catalytic activity of Raney's nickel, and in preparation process, add magnetic field, make the sequence in active centre more smooth and easy, thus further increase its catalytic activity.
As preferably, described alkali lye is the sodium hydroxide solution of massfraction 38-40%.
As preferably, mix according to the solid-liquid ratio of 1g:40-50mL:15-20mL with the dimethyl formamide solution of mass concentration 30-50% and acid solution before powdered alloy activation, 60-75min is uniformly mixed at control temperature 95-100 DEG C, filter, use water and absolute ethanol washing respectively, at 160-180 DEG C, vacuum-drying 15-20min obtains elementary modified alloy powder; Mixed with the solid-liquid ratio of chemical shearing liquid according to 1g:45-55mL by elementary modified alloy powder, be heated to 280-320 DEG C, hydro-thermal reaction 2-3h, cooling, washing, obtains secondary modified alloy powder; Secondary modified alloy powder mixes according to the solid-liquid ratio of 1g:35-45mL with the perchloric acid of mass concentration 50-60%, is heated to 180-220 DEG C and keeps 10 hours, cooling, filter, washing, obtain modified alloy powder after vacuum-drying.In the technical program, the dimethyl formamide solution of powdered alloy and mass concentration 30-50% and acid solution are mixed, be aided with stirring simultaneously, to expand the contact surface of powdered alloy and liquid, powdered alloy is uniformly dispersed, the dimethyl formamide solution of mass concentration 30-50% and the specific solvent combined system of acid solution, powdered alloy can be made to disperse in system evenly, effectively avoid powdered alloy to reunite.
First by even for nm inorganic compound Granular composite, be beneficial to follow-up shearing like this, by finely dispersed nm inorganic compound particle and the present invention's specific chemical shearing liquid hydro-thermal reaction, effectively can cut off powdered alloy, obtain the homogenization powdered alloy of length more homogeneous (length is greatly about 100-150nm) left and right.
Then by homogenization powdered alloy hydro-thermal reaction in perchloric acid, perchloric acid molecule can intercalation, swelling powdered alloy, powdered alloy is separated from each other and is come out by its surperficial high reaction activity, thus realizing selectively functionalized.
As preferably, acid solution is the concentrated nitric acid of mass concentration 70% and the vitriol oil of mass concentration 98% mixture according to the volume ratio of 2.5-3.2:1.
As preferably, chemical shearing liquid is the sodium molybdate solution of concentration 0.9-1.2moL/L and the silicomolybdic acid solution of the concentration 0.6-0.8moL/L mixture according to the volume ratio of 1:1.
Beneficial effect of the present invention:
1) the invention provides a kind of method preparing DMAPA, technique is simple, ensure that and optionally improves, greatly reduce the output of unit weight slag, has saved the processing costs that a large amount of danger is useless;
2) method of the present invention reduces the consumption of raw material propylene nitrile and dimethylamine, has saved the raw material consumption cost of DMAPA synthesizer, has namely saved production cost, improve company interest;
3) method of the present invention is convenient to large-scale industry preparation, and in preparation process, effectively improve the selectivity that propionitrile prepares DMAPA, reduce the content that synthesis material also greatly reduces secondary amine in product, avoid containing too much heavy slag in product, reduce investment and the production operating cost of DMAPA and apparatus for converting.
Accompanying drawing explanation
Fig. 1 is that one of the present invention prepares N, the process flow sheet of the method for N-dimethyl-1,3-propylene diamine.
Embodiment
Below by specific embodiment, explanation is further described to technical scheme of the present invention.
If without specified otherwise, the raw material adopted in embodiments of the invention is the conventional raw material in this area, and the method adopted in embodiment, is the ordinary method of this area.
Embodiment 1
With reference to Fig. 1, one prepares N, and the method for N-dimethyl-1,3-propylene diamine, said method comprising the steps of:
A) vinyl cyanide is joined in synthesis reactor, control temperature 120 DEG C, under the condition of stirring, cooling water circulation cooling, add dimethylamine, remove dimethylamine through rectification under vacuum, pressure 0.03MPa, obtained N, N-dimethylaminopropionitrile; The mol ratio of vinyl cyanide and dimethylamine is 1:1;
B) by the N that step a) is obtained, N-dimethylaminopropionitrile adds autoclave, adds hydrogenation catalyst, in autoclave, pass into liquefied ammonia, be warming up to 80 DEG C, pressure remains on 2.5MPa, pass into hydrogen, stir and keep temperature 80 DEG C simultaneously, reaction, fore-running after sedimentation, rectifying obtains N, N-dimethyl-1,3-propylene diamine, then basin packaging; The mol ratio of hydrogenation catalyst and N, N-dimethyl propionitrile is 10:1; Cut during fore-running, temperature being greater than 134 DEG C sends into rectifying. and get reaction solution in autoclave and detect, DMAPA content 99.4%, propionitrile residual volume 0.01%, light constituent foreign matter content 0.15%, heavy constituent foreign matter content 0.61%, wherein secondary amine 0.37%.
The preparation method of hydrogenation catalyst is as follows: take 65 parts of Ni, 55 parts of Al and 10 part of supplementary additive nano silicons by weight, cool after melting at 3200 DEG C, pulverize 300 mesh sieves and obtain powdered alloy, powdered alloy is activated in alkali lye, apply the magnetic field of 1.5T in outside while activation, then washing to pH value is 10.2, and products therefrom is hydrogenation catalyst.Described alkali lye is the sodium hydroxide solution of massfraction 38%.
Mix according to the solid-liquid ratio of 1g:40mL:15mL with the dimethyl formamide solution of mass concentration 30% and acid solution before powdered alloy activation, 60min is uniformly mixed at control temperature 95 DEG C, filter, use water and absolute ethanol washing respectively, at 160 DEG C, vacuum-drying 15min obtains elementary modified alloy powder; Mixed with the solid-liquid ratio of chemical shearing liquid according to 1g:45mL by elementary modified alloy powder, be heated to 280 DEG C, hydro-thermal reaction 2h, cooling, washing, obtains secondary modified alloy powder; Secondary modified alloy powder mixes according to the solid-liquid ratio of 1g:35mL with the perchloric acid of mass concentration 50%, is heated to 180 DEG C and keeps 10 hours, cooling, filter, washing, obtain modified alloy powder after vacuum-drying.
Acid solution is the concentrated nitric acid of mass concentration 70% and the vitriol oil of mass concentration 98% mixture according to the volume ratio of 2.5:1.Chemical shearing liquid is the sodium molybdate solution of concentration 0.9moL/L and the silicomolybdic acid solution of the concentration 0.6moL/L mixture according to the volume ratio of 1:1.
Embodiment 2
With reference to Fig. 1, one prepares N, and the method for N-dimethyl-1,3-propylene diamine, said method comprising the steps of:
A) join in synthesis reactor by vinyl cyanide, control temperature 130 DEG C, add dimethylamine under the condition of stirring, cooling water circulation cooling, remove dimethylamine through rectification under vacuum, pressure is 0.04MPa, obtained N, N-dimethylaminopropionitrile; The mol ratio of vinyl cyanide and dimethylamine is 1:1;
B) by the N that step a) is obtained, N-dimethylaminopropionitrile adds autoclave, adds hydrogenation catalyst, in autoclave, pass into liquefied ammonia, be warming up to 90 DEG C, pressure remains on 2.8MPa, pass into hydrogen, stir and keep temperature 90 DEG C simultaneously, reaction, fore-running after sedimentation, rectifying obtains N, N-dimethyl-1,3-propylene diamine, then basin packaging; The mol ratio of hydrogenation catalyst and N, N-dimethyl propionitrile is 10:1; Cut during fore-running, temperature being greater than 134 DEG C sends into rectifying.Get reaction solution in autoclave to detect, DMAPA content 99.2%, propionitrile residual volume 0.01%, light constituent foreign matter content 0.08%, heavy constituent foreign matter content 0.51%, wherein secondary amine 0.16%.
The preparation method of hydrogenation catalyst is as follows: take 68 parts of Ni, 58 parts of Al and 11 part of supplementary additive Graphenes by weight, cool after melting at 3250 DEG C, pulverize 350 mesh sieves and obtain powdered alloy, powdered alloy is activated in alkali lye, apply the magnetic field of 1.7T in outside while activation, then washing to pH value is 10.8, and products therefrom is hydrogenation catalyst.
Described alkali lye is the sodium hydroxide solution of massfraction 39%.
Mix according to the solid-liquid ratio of 1g:45mL:18mL with the dimethyl formamide solution of mass concentration 45% and acid solution before powdered alloy activation, 70min is uniformly mixed at control temperature 98 DEG C, filter, use water and absolute ethanol washing respectively, at 180 DEG C, vacuum-drying 18min obtains elementary modified alloy powder; Mixed with the solid-liquid ratio of chemical shearing liquid according to 1g:50mL by elementary modified alloy powder, be heated to 300 DEG C, hydro-thermal reaction 2.5h, cooling, washing, obtains secondary modified alloy powder; Secondary modified alloy powder mixes according to the solid-liquid ratio of 1g:40mL with the perchloric acid of mass concentration 55%, is heated to 200 DEG C and keeps 10 hours, cooling, filter, washing, obtain modified alloy powder after vacuum-drying.
Acid solution is the concentrated nitric acid of mass concentration 70% and the vitriol oil of mass concentration 98% mixture according to the volume ratio of 3:1.Chemical shearing liquid is the sodium molybdate solution of concentration 1moL/L and the silicomolybdic acid solution of the concentration 0.7moL/L mixture according to the volume ratio of 1:1.
Embodiment 3
With reference to Fig. 1, one prepares N, and the method for N-dimethyl-1,3-propylene diamine, said method comprising the steps of:
A) vinyl cyanide is joined in synthesis reactor, control temperature 140 DEG C, under the condition of stirring, cooling water circulation cooling, add dimethylamine, remove dimethylamine through rectification under vacuum, pressure 0.05MPa, obtained N, N-dimethylaminopropionitrile; The mol ratio of vinyl cyanide and dimethylamine is 1:1;
B) by the N that step a) is obtained, N-dimethylaminopropionitrile adds autoclave, adds hydrogenation catalyst, in autoclave, pass into liquefied ammonia, be warming up to 95 DEG C, pressure remains on 3MPa, pass into hydrogen, stir and keep temperature 95 DEG C simultaneously, reaction, fore-running after sedimentation, rectifying obtains N, N-dimethyl-1,3-propylene diamine, then basin packaging; The mol ratio of hydrogenation catalyst and N, N-dimethyl propionitrile is 10:1; Cut during fore-running, temperature being greater than 134 DEG C sends into rectifying.Get reaction solution in autoclave to detect, DMAPA content 98.9%, propionitrile residual volume 0.01%, light constituent foreign matter content 0.12%, heavy constituent foreign matter content 0.87%, wherein secondary amine 0.23%.
The preparation method of hydrogenation catalyst is as follows: take 70 parts of Ni, 60 parts of Al and 12 part of supplementary additive nano titanium oxides by weight, cool after melting at 3300 DEG C, pulverize 400 mesh sieves and obtain powdered alloy, powdered alloy is activated in alkali lye, apply the magnetic field of 1.8T in outside while activation, then washing to pH value is 11.3, and products therefrom is hydrogenation catalyst.Described alkali lye is the sodium hydroxide solution of massfraction 40%.
Mix according to the solid-liquid ratio of 1g:50mL:20mL with the dimethyl formamide solution of mass concentration 50% and acid solution before powdered alloy activation, 75min is uniformly mixed at control temperature 100 DEG C, filter, use water and absolute ethanol washing respectively, at 180 DEG C, vacuum-drying 20min obtains elementary modified alloy powder; Mixed with the solid-liquid ratio of chemical shearing liquid according to 1g:55mL by elementary modified alloy powder, be heated to 320 DEG C, hydro-thermal reaction 3h, cooling, washing, obtains secondary modified alloy powder; Secondary modified alloy powder mixes according to the solid-liquid ratio of 1g:45mL with the perchloric acid of mass concentration 60%, is heated to 220 DEG C and keeps 10 hours, cooling, filter, washing, obtain modified alloy powder after vacuum-drying.
Acid solution is the concentrated nitric acid of mass concentration 70% and the vitriol oil of mass concentration 98% mixture according to the volume ratio of 3.2:1.Chemical shearing liquid is the sodium molybdate solution of concentration 1.2moL/L and the silicomolybdic acid solution of the concentration 0.8moL/L mixture according to the volume ratio of 1:1.
Claims (10)
1. prepare a N, the method for N-dimethyl-1,3-propylene diamine, is characterized in that, said method comprising the steps of:
A) vinyl cyanide is joined in synthesis reactor, control temperature 120-140 DEG C, under the condition of stirring, cooling water circulation cooling, add dimethylamine, remove dimethylamine through rectification under vacuum and obtain N, N-dimethylaminopropionitrile;
B) by the N that step a) is obtained, N-dimethylaminopropionitrile adds autoclave, adds hydrogenation catalyst, in autoclave, pass into liquefied ammonia, be warming up to 80-95 DEG C, pressure remains on 2.5-3MPa, pass into hydrogen, stir and keep temperature 80-95 DEG C simultaneously, reaction, fore-running after sedimentation, rectifying obtains N, N-dimethyl-1,3-propylene diamine, then basin packaging.
2. one according to claim 1 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, in step a), the mol ratio of vinyl cyanide and dimethylamine is 1:1.
3. one according to claim 1 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, the mol ratio of hydrogenation catalyst and N, N-dimethyl propionitrile is 10:1.
4. one according to claim 1 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, cut during fore-running, temperature being greater than 134 DEG C sends into rectifying.
5. one according to claim 1 prepares N, N-dimethyl-1, the method of 3-propylene diamine, it is characterized in that, the preparation method of hydrogenation catalyst is as follows: take 65-70 part Ni, 55-60 part Al and 10-12 part supplementary additive by weight, cool after melting at 3200-3300 DEG C, pulverize 300-400 mesh sieve and obtain powdered alloy, powdered alloy is activated in alkali lye, apply the magnetic field of 1.5-1.8T in outside while activation, then washing to pH value is 10.2-11.3, and products therefrom is hydrogenation catalyst.
6. one according to claim 5 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, described supplementary additive is Graphene, nano titanium oxide, lanthanum trioxide or nano silicon.
7. one according to claim 5 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, described alkali lye is the sodium hydroxide solution of massfraction 38-40%.
8. one according to claim 5 prepares N, N-dimethyl-1, the method of 3-propylene diamine, it is characterized in that, mix according to the solid-liquid ratio of 1g:40-50mL:15-20mL with the dimethyl formamide solution of mass concentration 30-50% and acid solution before powdered alloy activation, at control temperature 95-100 DEG C, be uniformly mixed 60-75min, filter, use water and absolute ethanol washing respectively, at 160-180 DEG C, vacuum-drying 15-20min obtains elementary modified alloy powder; Mixed with the solid-liquid ratio of chemical shearing liquid according to 1g:45-55mL by elementary modified alloy powder, be heated to 280-320 DEG C, hydro-thermal reaction 2-3h, cooling, washing, obtains secondary modified alloy powder; Secondary modified alloy powder mixes according to the solid-liquid ratio of 1g:35-45mL with the perchloric acid of mass concentration 50-60%, is heated to 180-220 DEG C and keeps 10 hours, cooling, filter, washing, obtain modified alloy powder after vacuum-drying.
9. one according to claim 8 prepares N, and the method for N-dimethyl-1,3-propylene diamine, is characterized in that, acid solution is the concentrated nitric acid of mass concentration 70% and the vitriol oil of mass concentration 98% mixture according to the volume ratio of 2.5-3.2:1.
10. one according to claim 8 prepares N, N-dimethyl-1, the method of 3-propylene diamine, is characterized in that, chemical shearing liquid is the sodium molybdate solution of concentration 0.9-1.2moL/L and the silicomolybdic acid solution of the concentration 0.6-0.8moL/L mixture according to the volume ratio of 1:1.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106223068A (en) * | 2016-08-12 | 2016-12-14 | 浙江真爱时尚家居有限公司 | A kind of production technology of TR spandex fabric woollen mixed blanket |
| CN110252322A (en) * | 2019-07-05 | 2019-09-20 | 安徽天择化工有限公司 | A kind of quaternary Raney nickel, preparation method and its application |
| CN113200870A (en) * | 2021-05-07 | 2021-08-03 | 大连理工大学 | Process for continuously preparing N, N-dimethyl-1, 3-propane diamine by using micro-mixing and fixed bed reactor |
| CN113501761A (en) * | 2021-07-16 | 2021-10-15 | 万华化学集团股份有限公司 | Method for continuously producing N, N-diethyl-1, 3-propane diamine by one-step method |
| CN116199588A (en) * | 2023-01-10 | 2023-06-02 | 大连理工大学 | Method for preparing N- (2-hydroxyethyl) -1, 3-propanediamine in semi-continuous mode by combining Y-type micro-mixing reactor and high-pressure reaction kettle |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2877113A (en) * | 1955-07-23 | 1959-03-10 | Siemens Planiawerke Ag | Method of producing sintered nickelaluminum articles |
| EP0913388A1 (en) * | 1997-10-30 | 1999-05-06 | Air Products And Chemicals, Inc. | Hydrogenation of nitriles to produce amines |
| US20120029225A1 (en) * | 2010-07-29 | 2012-02-02 | Basf Se | DMAPN Having a Low DGN Content and a Process for Preparing DMAPA from DMAPN Having a Low DGN Content |
| CN104084219A (en) * | 2014-07-08 | 2014-10-08 | 赛鼎工程有限公司 | Preparation method and application of Raney Ni catalyst suitable for methanation of fixed bed |
| CN104492449A (en) * | 2014-12-08 | 2015-04-08 | 九江天赐高新材料有限公司 | Preparation method of hydrogenation catalyst and method for synthesizing DMAPA (dimethyl amionopropylamine) by applying catalyst |
-
2015
- 2015-09-15 CN CN201510584409.7A patent/CN105198754B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2877113A (en) * | 1955-07-23 | 1959-03-10 | Siemens Planiawerke Ag | Method of producing sintered nickelaluminum articles |
| EP0913388A1 (en) * | 1997-10-30 | 1999-05-06 | Air Products And Chemicals, Inc. | Hydrogenation of nitriles to produce amines |
| US20120029225A1 (en) * | 2010-07-29 | 2012-02-02 | Basf Se | DMAPN Having a Low DGN Content and a Process for Preparing DMAPA from DMAPN Having a Low DGN Content |
| CN104084219A (en) * | 2014-07-08 | 2014-10-08 | 赛鼎工程有限公司 | Preparation method and application of Raney Ni catalyst suitable for methanation of fixed bed |
| CN104492449A (en) * | 2014-12-08 | 2015-04-08 | 九江天赐高新材料有限公司 | Preparation method of hydrogenation catalyst and method for synthesizing DMAPA (dimethyl amionopropylamine) by applying catalyst |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106223068A (en) * | 2016-08-12 | 2016-12-14 | 浙江真爱时尚家居有限公司 | A kind of production technology of TR spandex fabric woollen mixed blanket |
| CN110252322A (en) * | 2019-07-05 | 2019-09-20 | 安徽天择化工有限公司 | A kind of quaternary Raney nickel, preparation method and its application |
| CN113200870A (en) * | 2021-05-07 | 2021-08-03 | 大连理工大学 | Process for continuously preparing N, N-dimethyl-1, 3-propane diamine by using micro-mixing and fixed bed reactor |
| CN113501761A (en) * | 2021-07-16 | 2021-10-15 | 万华化学集团股份有限公司 | Method for continuously producing N, N-diethyl-1, 3-propane diamine by one-step method |
| CN113501761B (en) * | 2021-07-16 | 2023-08-11 | 万华化学集团股份有限公司 | Method for continuously producing N, N-diethyl-1, 3-propanediamine by one-step method |
| CN116199588A (en) * | 2023-01-10 | 2023-06-02 | 大连理工大学 | Method for preparing N- (2-hydroxyethyl) -1, 3-propanediamine in semi-continuous mode by combining Y-type micro-mixing reactor and high-pressure reaction kettle |
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|---|---|
| CN105198754B (en) | 2017-06-23 |
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Denomination of invention: A method for preparing N, n-dimethyl-1,3-propanediamine Effective date of registration: 20201223 Granted publication date: 20170623 Pledgee: Zhejiang Jiangshan rural commercial bank Limited by Share Ltd. Pledgor: ZHEJIANG HILL CHEMICAL Co.,Ltd. Registration number: Y2020330001267 |