CN101684073B - Method for producing isopropylamine - Google Patents
Method for producing isopropylamine Download PDFInfo
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- CN101684073B CN101684073B CN 200810223639 CN200810223639A CN101684073B CN 101684073 B CN101684073 B CN 101684073B CN 200810223639 CN200810223639 CN 200810223639 CN 200810223639 A CN200810223639 A CN 200810223639A CN 101684073 B CN101684073 B CN 101684073B
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Abstract
The invention discloses a method for producing isopropylamine, which belongs to the technical field of amine. To solve the problem that the prior isopropylamine industrial production device cannot effectively convert diisopropylamine into the isopropylamine, a reactor for an acetone hydroamination reaction performs the sectional control of the reaction temperature, the reaction temperature of a first section positioned at an inlet of the reactor is between 110 and 150 DEG C, and the reaction temperature of a downstream section is 5 to 30 DEG C higher than that of an upstream section which is adjacent to the downstream section. Along with the gradual reduction of the concentration of acetone along a bed, the reaction temperature is improved section by section, which is favorable for converting the diisopropylamine and isopropanol into the isopropylamine, thereby reducing the circulation of the diisopropylamine and the isopropanol, reducing energy consumption, and preventing the diisopropylamine from being gradually accumulated in a system so as not to need operating a diisopropylamine rectification system with difficult operation. The method is simple, feasible and easy to realize, and has considerable industrial application value and economic benefit.
Description
Technical field
The present invention relates to a kind of method of producing amine, more particularly, the present invention relates to a kind of method of producing Isopropylamine.
Background technology
Isopropylamine is the important source material of production Multiple Pesticides such as G-30027, isofenphos_methyl and Buprofezin etc.; Also can be used for producing washing composition such as Witco 1298 Soft Acid isopropyl amine salt etc.; Also widespread use in rubber industry and medicine industry.
The production method of people's p-isopopylaniline has been carried out large quantity research, and some also is applied in the industry maturely.Wherein mainly contain: (1) Virahol gas phase ammoniation process, the method is take Virahol as raw material, in the presence of copper, nickel or cobalt catalyst, Virahol and ammonia react under hydro condition and generate Isopropylamine, disclosed such as No. 2349461, United States Patent (USP), No. 2636902, reaction conditions is: 180～250 ℃ of temperature, pressure 1.0～2.5MPa, volume space velocity are 0.2h
-1(2) acetone hydrogen ammonating process, the method are take acetone as raw material, use the Ni catalyzer, and acetone and hydrogen, ammonia carry out the hydrogen aminating reaction, generate Isopropylamine.As the nickel catalyzator that uses the Beijing Chemical Research Institute to produce, in fixed-bed reactor, make acetone carry out the hydrogen aminating reaction, this catalyst technology is ripe, uses for many years industrial.
Although acetone hydrogen ammonating process is very ripe,, in fixed-bed reactor, acetone 100% ground can not be changed into Isopropylamine, generate inevitably Diisopropylamine, Virahol.Mode commonly used is Diisopropylamine, Virahol to be looped back reactor continue reaction generation Isopropylamine, cause energy consumption to increase, the reactor for treatment amount strengthens, and a large amount of Diisopropylamines that circulate easily produce coking, reduce catalyst activity, reactor and pipeline also can result in blockage.Thereby circulate in a large number Diisopropylamine, Virahol are not basic terms of settlement.For this reason, CN95102074.9 proposes to increase an auxiliary reactor in technical process, and the temperature of reaction of auxiliary reactor is 140～150 ℃, and main reactor adopts sectional temperature-controlled, and the epimere temperature is 90～150 ℃, and the hypomere temperature is 50～90 ℃.Adopting sectional temperature-controlled purpose is to carry out gas-solid phase reaction in epimere, and the hypomere temperature of reaction reduces, and makes reaction be converted into gas-liquid-solid phase reaction, can improve like this purity and the yield of product.Diisopropylamine, iso-propanol conversion with unreacted acetone, generation in auxiliary reactor become Isopropylamine.This patent adopts two reactors of major-minor, does not need Diisopropylamine, Virahol are recycled to main reactor.But owing to using two reactors, facility investment increases, and running cost also strengthens, thereby does not also have industrial application at present.
At present industrially still use a reactor, carry out single hop control, not segmentation control loops back reactor with Diisopropylamine and the Virahol that generates, and fresh acetone together with hydrogen, ammonia react, generate Isopropylamine.But because reactor adopts single hop control, the hydrogen aminating reaction of applicable acetone, temperature of reaction is still lower concerning the reaction of Diisopropylamine generation Isopropylamine, thereby the Diisopropylamine that loops back can not change into Isopropylamine ideally, thereby cause the concentration of Diisopropylamine in production equipment more and more higher, namely there is accumulation, at least need to open termly the distillation system of separation Diisopropylamine with the Diisopropylamine concentration in the reduction system, but the separation of Diisopropylamine is to use Diisopropylamine, the isopropyl alcohol and water forms the principle of ternary azeotrope, thereby the distillation system operation that separates Diisopropylamine is very difficult, be easy to cause general tower, thereby increase manufacturing cost.
In sum, existing Isopropylamine industrial installation exists the problem that Diisopropylamine can not be converted into Isopropylamine effectively.
Summary of the invention
The present invention is for the problems referred to above, and considers industrial easy realization, proposes reactor sectional temperature-controlled, and the temperature of reaction of tract is higher than the temperature of reaction of Upstream section.
Concrete technical scheme is as follows.
The method of production Isopropylamine of the present invention, in fixed-bed reactor, in the presence of nickel-base catalyst, acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate Isopropylamine, Diisopropylamine and Virahol, wherein Diisopropylamine is recycled to described reactor with Virahol after separating, it is characterized in that, described reactor is carried out segmentation control temperature of reaction, the temperature of reaction that is positioned at the first paragraph of reactor inlet is 110～150 ℃, and the tract temperature of reaction is higher 5～30 ℃ than the Upstream section temperature of reaction that is adjacent.
Preferably, the tract temperature of reaction is higher 10～20 ℃ than the Upstream section temperature of reaction that is adjacent.
For the ease of industrialization, more preferably described fixed-bed reactor divide 2～3 sections control temperature of reaction, and the tract temperature of reaction is higher 10～20 ℃ than the Upstream section temperature of reaction that is adjacent.
Particularly, the method for production Isopropylamine of the present invention may further comprise the steps:
(1) temperature of reaction that acetone and the Diisopropylamine, Virahol and the hydrogen that loop back and ammonia is heated to first paragraph, send into the fixed-bed reactor that nickel-base catalyst is housed and carry out the hydrogen aminating reaction, acetone in the charging: hydrogen: the mol ratio of ammonia is 1:2～4:2～4, and the liquid acetone volume space velocity is 0.1～0.5h
-1, described reactor is sectional temperature-controlled as carrying out as described in each in the claim 1～3;
(2) gas-liquid separation is carried out in the in the future material of autoreactor cooling, and the compressed machine recirculated compressed of gas is returned reactor, and liquid is sent into deammoniation tower, isolates ammonia from cat head, delivers to reactor, is rich in the material of Isopropylamine from the tower reactor extraction;
(3) will be incorporated into from the material of deamination tower reactor the Isopropylamine tower, the process refinery distillation is from overhead extraction Isopropylamine product in the Isopropylamine tower, and the tower reactor extraction contains the material of Diisopropylamine, isopropyl alcohol and water;
(4) material with the Isopropylamine tower reactor is incorporated into dehydration tower, isolates the material as leading take Diisopropylamine and Virahol at cat head, loops back reactor, and tower reactor is discharged waste water.
Preferably, the deammoniation tower cat head does not arrange condenser, and the raw materials ammonia of adding is directly sent into the deammoniation tower top as low-temperature receiver, and the component except ammonia is condensed and forms liquid phase stream at reflux in tower, and liquid ammonia gasification is that gas ammonia is from overhead extraction and deliver to reactor.More preferably, deammoniation tower has 20～40 number of theoretical plates, and tower top temperature is 25～40 ℃, and tower top pressure is 1.1～1.4MPa.
Reactor of the present invention can adopt atmospheric operation, also can pressurized operation, and for example working pressure is 0.6～1.0MPa.The upper feeding mode can be, also lower feeding manner can be.
In the method for the invention, cooling comes basic identical in water cooler, gas-liquid separator, Isopropylamine tower and the dehydration tower of material of autoreactor and the existing full scale plant.The disclosed content of CN95102074.9 is all introduced reference.
Originally, the rectifying tower that designs in the Isopropylamine industrial production flow process is very complete, except previously described knockout tower, also comprises Diisopropylamine tower, Virahol tower etc.For simple flow, it is Isopropylamine with Diisopropylamine and the iso-propanol conversion that generates that CN95102074.9 proposes to increase an auxiliary reactor, with cancellation Diisopropylamine tower, Virahol tower etc.But, since in full scale plant many reactors, cost of investment and running cost all can strengthen, thereby industrially do not use two reactors, remain circulation Diisopropylamine and Virahol.Thereby, also need in the full scale plant at present the distillation system that separates Diisopropylamine is set, when treating that the concentration of Diisopropylamine in system is higher, open this system and separate catalyst deactivation and the system jams of Diisopropylamine to prevent from causing because of Diisopropylamine.The contriver is through intensive research, finding that Diisopropylamine is converted into the temperature of reaction of Isopropylamine need to be higher than acetone hydrogen aminating reaction temperature, thereby in existing full scale plant, reactor is carried out the single hop temperature control can not transform Diisopropylamine ideally, but the temperature that improves reactor is unfavorable for again the selectivity of acetone hydrogen aminating reaction, it is more and more higher thereby the concentration of Diisopropylamine in system to occur, need to move termly the distillation system of Diisopropylamine.
The contriver is in order fundamentally to address this problem, the opposite technical scheme that proposition is sectional temperature-controlled with the disclosed main reactor of CN95102074.9 and the hypomere temperature of reaction is lower than epimere temperature of reaction, be that a reactor only is set in the Production Flow Chart, reactor is sectional temperature-controlled, but the tract temperature of reaction is higher than Upstream section temperature of reaction.Carrying out along with acetone hydrogen aminating reaction, acetone content is more and more lower along beds, at this moment improve temperature of reaction, selectivity impact on acetone hydrogen aminating reaction is little, and temperature of reaction is conducive to Diisopropylamine and iso-propanol conversion is Isopropylamine and improve, thereby reduces the internal circulating load of Diisopropylamine and Virahol, reduce energy consumption, be conducive to improve the processing power of device, prevent that simultaneously Diisopropylamine from accumulating in system, can completely abolish the Diisopropylamine distillation system.
In addition, the liquefied ammonia of adding adds system at the deammoniation tower top, omitted the overhead condenser of deammoniation tower, the deamination overhead condenser does not need lower low-temperature receiver on the one hand, the liquefied ammonia of adding on the other hand gasifies in deammoniation tower and has saved the heat of gasification liquefied ammonia, thereby has reduced energy consumption and the production cost of device.
The method simple possible of generation Isopropylamine of the present invention, only need a reactor, in whole device, do not build the Diisopropylamine distillation system, to control temperature of reaction just passable as long as be divided into several sections with regard to reactor, namely shell side is divided into several sections, and the temperature of reaction of controlling respectively each section with the water of differing temps gets final product, thereby method of the present invention easily realizes, yet method of the present invention can be omitted the Diisopropylamine distillation system, greatly reduces cost of investment and running cost, and convenient operation.Therefore, method is simple, but has considerable economic benefit.
Description of drawings
Fig. 1 is the schematic flow sheet of the method for production Isopropylamine of the present invention.
Nomenclature:
1. preheater; 2. reactor; 3. water cooler; 4. gas-liquid separator; 5. deammoniation tower; 6. Isopropylamine tower; 7. dehydration tower.
Embodiment
Further explain the method for production Isopropylamine of the present invention below in conjunction with accompanying drawing.
As shown in Figure 1, the calandria type fixed bed reactor that nickel-base catalyst is housed is carried out sectional temperature-controlled mode.Reactor shown in Figure 1 is the Flow of Goods and Materials mode of upper entering and lower leaving, minute three sections temperature controls.The temperature of reaction that is arranged in the first paragraph of entrance is controlled at 110～150 ℃ of scopes, for example 120～125 ℃.The temperature of reaction of second segment is higher 5～30 ℃ than first paragraph, preferred 10～20 ℃, for example is controlled in 135～140 ℃ of scopes.The 3rd section temperature of reaction is higher 5～30 ℃ than second segment, preferred 10～20 ℃, for example is controlled in 145～150 ℃ of scopes.The temperature of reaction that the above provides and adjacent two sections temperature head only are schematically, can regulate according to use initial stage, mid-term and the latter stage of catalyzer.In order to prevent from generating polymkeric substance, the temperature of reaction that is positioned at the back segment of reactor outlet also should not be too high, for example is no more than 190 ℃.
Acetone, the hydrogen of adding, from the circulation gas of gas-liquid separator, from the gas ammonia of deamination cat head with after preheater 1 preheating, enter sectional temperature-controlled fixed-bed reactor 2 from the circulation fluid of dehydration cat head and carry out the hydrogen aminating reaction.Through supercooler 3 coolings, be separated into gas and liquid from reactor 2 material out in gas-liquid separator 4, gas uses as the compressed machine compression of circulation gas Returning reactor, and liquid is sent into deammoniation tower 5.Material process in deammoniation tower 5 from deammoniation tower 5 stills is separated, isolate gas ammonia from cat head, the deamination cat head does not arrange condenser, add the low-temperature receiver of liquefied ammonia to push up as deammoniation tower 5 that to add at the top, the liquid ammonia gasification of adding enters reactor 2 with isolated gas ammonia from the material from gas-liquid separator 4, and the material of Isopropylamine is rich in deammoniation tower 5 still extraction.The material that is rich in Isopropylamine is incorporated into Isopropylamine tower 6, and from overhead extraction Isopropylamine product, tower reactor is discharged the material that contains Diisopropylamine, Virahol, water and micro-Isopropylamine.The material that Isopropylamine tower 6 stills are discharged is incorporated into dehydration tower 7, separates water outlet from tower reactor, contains the circulation fluid of Diisopropylamine, Virahol and micro-Isopropylamine from overhead extraction, and this circulation fluid is delivered to reactor.
The present embodiment is used for illustrating that acetone, Diisopropylamine, iso-propanol conversion are the temperature of reaction difference of Isopropylamine.
In testing laboratory, adopt fixed-bed reactor, the catalyst for isopropylamine that uses the Beijing Chemical Research Institute to produce, loadings is 50 milliliters, carries out gas-phase reaction.
Test 1: carry out hydrogen aminating reaction synthesizing isopropamide take acetone as raw material, reaction conditions is: the liquid acetone volume space velocity is 0.5h
-1, pressure is normal pressure, temperature of reaction is 152 ℃, acetone: hydrogen: the mol ratio of ammonia is 1:3:3.Test-results is listed in the table 1.
Test 2: for the material in the analoging industrial device, take the mixture of Diisopropylamine and each 50wt% of Virahol as raw material, in the presence of hydrogen, they and ammonia react are converted into Isopropylamine, mass ratio according to fresh acetone in the full scale plant and circulation fluid is about 3/1, thereby in the present embodiment, the liquid volume air speed of the mixture of Diisopropylamine and Virahol is set as 0.17h
-1, other reaction conditions is: pressure is normal pressure, temperature of reaction is 152 ℃ or 170 ℃, (Diisopropylamine+Virahol): hydrogen: the mol ratio of ammonia is 1:3:3.Test-results is listed in the table 1.
Table 1
Can find out from the data of table 1, under the condition of liquid air speed analoging industrial device, namely acetone is 0.5h
-1, circulation fluid is 0.17h
-1, under same reaction temperature was 152 ℃, the transformation efficiency of acetone was higher than the transformation efficiency of Diisopropylamine and Virahol.If the raising temperature of reaction, the transformation efficiency of Diisopropylamine and Virahol also increases.Thereby under at present industrial reactor implementation single hop temperature control, the transformation efficiency of circulation fluid is than the low conversion rate of acetone.Therefore in actual industrial production, the amount of circulation fluid can get more and more, and needs to move at least termly or continuously the Diisopropylamine distillation system.
The present embodiment is used for explaining sectional temperature-controlled hydrogen aminating reaction of the present invention.
Sectional temperature-controlled for reactor in the analoging industrial device, in testing laboratory, reactor is divided into two sections, i.e. two sections beds, each section load respectively the catalyst for isopropylamine that 50 milliliters of Beijing Chemical Research Institute produce, and two sections temperature controls respectively carry out gas-phase reaction.
Charging is the mixture that contains 75wt% acetone, 12.5wt% Diisopropylamine and 12.5wt% Virahol, and the liquid volume air speed of acetone is 0.5h
-1The temperature of reaction of first paragraph bed is controlled at 152 ℃, and the temperature of reaction of second segment bed is controlled at 170 ℃, and pressure is normal pressure, (acetone+Diisopropylamine+Virahol): hydrogen: the mol ratio of ammonia is 1:3:3.The content of each component in the reaction product is listed in table 2.
In addition, the temperature of reaction of two sections beds all is controlled at 152 ℃, carries out identical test, content and the transformation efficiency of each component in the reaction product are listed in table 2.
The content of each component and transformation efficiency in table 2 reaction product
As can be seen from Table 2, divide two sections but the identical single hop bed bioreactor that namely is equivalent to of two-stage reaction temperature to compare with reactor, the temperature of reaction that reactor is divided into two sections beds and hypomere bed is during than high 18 ℃ of the temperature of reaction of epimere bed, the transformation efficiency of acetone improves a little, Diisopropylamine and Virahol change positive transformation efficiency into by negative transformation efficiency, namely are converted into minimizing by increase.Therefore, method of the present invention can prevent that Diisopropylamine and Virahol from accumulating in system, can completely abolish the Diisopropylamine distillation system, and easily realizes.
Claims (4)
1. method of producing Isopropylamine, in fixed-bed reactor, in the presence of nickel-base catalyst, acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate Isopropylamine, Diisopropylamine and Virahol, wherein Diisopropylamine is recycled to described reactor with Virahol after separating, it is characterized in that, described reactor is carried out minute 2～3 sections control temperature of reaction, the temperature of reaction that is positioned at the first paragraph of reactor inlet is 110～150 ℃, and the tract temperature of reaction is higher 10～20 ℃ than the Upstream section temperature of reaction that is adjacent.
2. the method for production Isopropylamine as claimed in claim 1 is characterized in that, said method comprising the steps of:
(1) temperature of reaction that acetone and the Diisopropylamine, Virahol and the hydrogen that loop back and ammonia is heated to first paragraph, send into the fixed-bed reactor that nickel-base catalyst is housed and carry out the hydrogen aminating reaction, acetone in the charging: hydrogen: the mol ratio of ammonia is 1:2～4:2～4, and the liquid acetone volume space velocity is 0.1～0.5h
-1, described reactor is carried out sectional temperature-controlled as claimed in claim 1;
(2) gas-liquid separation is carried out in the in the future material of autoreactor cooling, and the compressed machine recirculated compressed of gas is returned reactor, and liquid is sent into deammoniation tower, isolates ammonia from cat head, delivers to reactor, is rich in the material of Isopropylamine from the tower reactor extraction;
(3) will be incorporated into from the material of deamination tower reactor the Isopropylamine tower, the process refinery distillation is from overhead extraction Isopropylamine product in the Isopropylamine tower, and the tower reactor extraction contains the material of Diisopropylamine, isopropyl alcohol and water;
(4) material with the Isopropylamine tower reactor is incorporated into dehydration tower, isolates the material as leading take Diisopropylamine and Virahol at cat head, loops back reactor, and tower reactor is discharged waste water.
3. the method for production Isopropylamine as claimed in claim 2, it is characterized in that, the deammoniation tower cat head does not arrange condenser, the raw materials ammonia of adding is directly sent into the deammoniation tower top as low-temperature receiver, component except ammonia is condensed and forms liquid phase stream at reflux in tower, and liquid ammonia gasification is that gas ammonia is from overhead extraction and deliver to reactor.
4. the method for production Isopropylamine as claimed in claim 2 is characterized in that, deammoniation tower has 20～40 number of theoretical plates, and tower top temperature is 25～40 ℃, and tower top pressure is 1.1～1.4MPa.
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| CN 200810223639 CN101684073B (en) | 2008-09-28 | 2008-09-28 | Method for producing isopropylamine |
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| CN 200810223639 CN101684073B (en) | 2008-09-28 | 2008-09-28 | Method for producing isopropylamine |
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| CN101684073B true CN101684073B (en) | 2013-01-02 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103420846B (en) * | 2012-05-14 | 2015-02-11 | 浙江新化化工股份有限公司 | Production method of isopropylamine |
| US9884805B2 (en) * | 2014-02-18 | 2018-02-06 | Basf Antwerpen Nv | Method for producing N-ethyl-diisopropylamine |
| CN106349085A (en) * | 2016-08-26 | 2017-01-25 | 安徽昊源化工集团有限公司 | Separation and purification method of crude isopropyl amine |
| CN108997142B (en) * | 2018-08-20 | 2021-01-12 | 浙江建业化工股份有限公司 | Method for removing residual ketone in production of fatty amine by ketone method |
| CN115819246B (en) * | 2022-11-30 | 2024-03-19 | 中国科学院大连化学物理研究所 | Preparation method of diisopropylamine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1130621A (en) * | 1995-03-06 | 1996-09-11 | 化学工业部北京化工研究院 | Process for producing isopropyl amine |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1130621A (en) * | 1995-03-06 | 1996-09-11 | 化学工业部北京化工研究院 | Process for producing isopropyl amine |
Non-Patent Citations (2)
| Title |
|---|
| 殷振海.异丙胺生产工艺.《河北化工》.1998,(第4期),第37-38页. * |
| 邢晓东等.合成异丙胺新工艺的研究.《精细石油化工》.1992,(第4期),第31-33页. * |
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