CN103420846A - Production method of isopropylamine - Google Patents
Production method of isopropylamine Download PDFInfo
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- CN103420846A CN103420846A CN201210150940XA CN201210150940A CN103420846A CN 103420846 A CN103420846 A CN 103420846A CN 201210150940X A CN201210150940X A CN 201210150940XA CN 201210150940 A CN201210150940 A CN 201210150940A CN 103420846 A CN103420846 A CN 103420846A
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Abstract
The invention relates to a production method of isopropylamine, and puts forward that: segmentally loading a fixed bed reactor with catalysts of different properties, loading an entrance end with a spherical nickel-base catalyst of moderate activity, loading an outlet end with a strip-type nickel-based catalyst of higher activity, under suitable reaction conditions, performing an hydrogen ammoniation reaction of acetone to produce the isopropylamine, and thus obtaining a isopropylamine product via necessary separation and refining. Through use of the production method of the isopropylamine, circulation of diisopropylamine and isopropyl alcohol can be avoided, energy consumption can be reduced, and a diisopropylamine distillation system inconvenient to operate can be omitted; and the production method of the isopropylamine is simple, feasible and easy to implement, 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.
Technical background
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 industry maturely.Wherein mainly contain: (1) Virahol gas phase ammoniation process, the method be take Virahol as raw material, under copper, nickel or cobalt catalyst exist, Virahol and ammonia react and generate Isopropylamine under hydro condition, as disclosed as No. 2349461, United States Patent (USP), No. 2636902, reaction conditions is: 180～250 ℃ of temperature, pressure 1.0～2.5MPa, and volume space velocity is 0.2h-1; (2) acetone hydrogen ammonating process, the method is to take acetone as raw material, uses the Ni catalyzer, acetone and hydrogen, ammonia carry out the hydrogen aminating reaction, generate Isopropylamine.As the nickel catalyzator that uses Beijing Chemical Research Institute to produce, in fixed-bed reactor, make acetone carry out the hydrogen aminating reaction, this catalyst technology maturation, used for many years industrial.
Although acetone hydrogen ammonating process is very ripe,, acetone 100% ground can not be changed into to Isopropylamine in fixed-bed reactor, inevitably generate Diisopropylamine, Virahol.Mode commonly used is Diisopropylamine, Virahol to be looped back to 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, CN 95102074.9 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.In auxiliary reactor, the Diisopropylamine of unreacted acetone, generation, iso-propanol conversion are become to 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 also there is no industrial application at present.
At present industrially still use a reactor, carry out single hop and control, segmentation is not controlled, and the Diisopropylamine of generation and Virahol are looped back to reactor, with together with fresh acetone with hydrogen, ammonia react, generate Isopropylamine.But because adopting single hop, reactor controls, the hydrogen aminating reaction of applicable acetone, temperature of reaction is still lower concerning the reaction of Diisopropylamine generation Isopropylamine, thereby the Diisopropylamine looped 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 undesirable problem of selectivity that generates Isopropylamine.
Summary of the invention
The present invention is in order to overcome the defect of prior art, and considers industrial easy realization, proposes two kinds of catalyzer that performance is different of filling in fixed-bed reactor, for the building-up reactions of Isopropylamine.
Concrete technical scheme is as follows:
The method of production Isopropylamine of the present invention is: in fixed-bed reactor, load spherical nickel-base catalyst near inlet end, near exit end filling bar shaped nickel-base catalyst, the specific surface area of described spherical nickel-base catalyst and pore volume are respectively 170～220m2/g and 0.5～0.8ml/g, the specific surface area of described bar shaped nickel-base catalyst and pore volume are respectively 140～170m2/g and 0.3～0.5ml/g, the loading height of described spherical nickel-base catalyst is 1/4～1/2 of fixed-bed reactor bed height, under the existence of described two kinds of catalyzer, acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate the reaction product that Isopropylamine is the master, temperature of reaction is 80～150 ℃, reaction pressure is 0.7～1.6MPa, the acetone solution hourly space velocity is 0.1～1.2h-1, acetone: hydrogen: the mol ratio of ammonia is 1: 1～4: 1～6.
It is an exothermic process that acetone hydrogen aminating reaction is produced Isopropylamine, and thermal discharge is larger.Adopt the single higher catalyzer of activity, at the reactor inlet end, violent thermopositive reaction occurs, be difficult to liberated heat is shifted out, cause like this local reaction temperature higher, side reaction is more, and the Diisopropylamine amount of generation is more.In the present invention, at the active moderate spherical nickel-base catalyst of reactor inlet end filling, make the response intensity of inlet end moderate, reaction heat can be shifted out in time, thereby can effectively control temperature of reaction, correspondingly reduce side reaction.Through reaction to a certain degree, acetone concentration reduces, and speed of reaction reduces, and at this moment enters active higher bar shaped nickel-base catalyst bed, thereby improves conversion rate, enhances productivity.The catalyst for isopropylamine BC-A-30 that the preferred Beijing Chemical Research Institute of described spherical nickel-base catalyst produces, the XH-3 catalyzer that the preferred ZheJiang XinHua Chemical Engineering Co., Ltd of described bar shaped nickel-base catalyst produces.
The conversion rate of acetone is not only relevant to temperature of reaction, and be subject to the activity influence of catalyzer, for the production efficiency that improves whole reactor with control reaction conditions to improve reaction preference, the loading height of described spherical nickel-base catalyst is preferably 1/4～1/3 of fixed-bed reactor bed height.
Acetone generates Isopropylamine through the hydrogen aminating reaction, for obtaining the Isopropylamine product, needs, through essential separation and refining, to said method comprising the steps of:
(1) Isopropylamine is synthetic:
In fixed-bed reactor, load spherical nickel-base catalyst near inlet end, near exit end filling bar shaped nickel-base catalyst, the specific surface area of described spherical nickel-base catalyst and pore volume are respectively 170～220m2/g and 0.5～0.8ml/g, the specific surface area of described bar shaped nickel-base catalyst and pore volume are respectively 140～170m2/g and 0.3～0.5ml/g, the loading height of described spherical nickel-base catalyst is 1/4～1/2 of fixed-bed reactor bed height, under the existence of described two kinds of catalyzer, raw material acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate the reaction product that Isopropylamine is the master, reaction conditions is: temperature of reaction is 80～150 ℃, and reaction pressure is 0.7～1.6MPa, and the acetone solution hourly space velocity is 0.1～1.2h-1, acetone: hydrogen: the mol ratio of ammonia is 1: 1～4: 1～6,
(2) material of self-retaining bed bioreactor is cooling in the future, carries out gas-liquid separation, and the compressed machine recirculated compressed of gas is returned reactor, and liquid is sent into deammoniation tower, from tower top, isolates ammonia, delivers to reactor, is rich in the material of Isopropylamine from the tower reactor extraction;
(3) will be incorporated into the Isopropylamine tower from the material that is rich in Isopropylamine of deamination tower reactor, pass through refinery distillation from overhead extraction Isopropylamine product in the Isopropylamine tower, the material that the tower reactor extraction contains Diisopropylamine, isopropyl alcohol and water;
(4) material that the Isopropylamine tower reactor is contained to Diisopropylamine, isopropyl alcohol and water is introduced film separating system, and the organic phase containing Virahol, Diisopropylamine after the dehydration of film separating system film is used as the raw material of producing Diisopropylamine.
Reactor of the present invention can be the upper feeding mode, can be also lower feeding manner.
In the method for the invention, basic identical in water cooler, gas-liquid separator, Isopropylamine tower and the dehydration tower of the cooling material that carrys out autoreactor and existing full scale plant.The disclosed content of CN 95102074.9 is all introduced to reference.
The method simple possible of synthesizing isopropamide of the present invention, only need a reactor, do not build the Diisopropylamine distillation system in whole device, as long as the different catalyzer of segmentation filling performance just can improve the selectivity of reaction greatly in fixed-bed reactor, thereby method of the present invention easily realizes, and can omit the Diisopropylamine distillation system, greatly reduce cost of investment and running cost, and convenient operation, method is simple, has considerable economic benefit.
Embodiment
Below in the mode of embodiment, further explain and illustrate the method for production Isopropylamine of the present invention, but method of the present invention is not limited to cited embodiment.
Embodiment 1
Fixed-bed reactor are 32 * 3mm, the stainless steel reactor of length 1350mm.The stainless steel temperature-measuring casing of ∮ 8 * 1mm is set in reactor, the trade mark that loads successively from top to bottom Beijing Chemical Research Institute's production is that the trade mark that BC-A-30 ball-type catalyst for isopropylamine and ZheJiang XinHua Chemical Engineering Co., Ltd produce is XH-3 stripe shape catalyzer, the catalyst loading total height is 960mm, wherein the ball shape catalyst loading height is that 270mm, stripe shape catalyst packing height are 690mm, and loaded catalyst is 510ml.Reaction raw materials is upper entering and lower leaving, and the material flowed out from reactor bottom enters in separator after condensing cooling, and vapor phase ammonia, hydrogen are discharged from the separator top, the bottom liquid phases timing sampling.
Temperature of reaction is 105 ℃, and reaction pressure is 0.8MPa, and the acetone liquid hourly space velocity is 0.5L acetone/(L catalyzer hour), and acetone: hydrogen: the mol ratio of ammonia is 1: 3: 3.Reaction result: acetone conversion 99%, the Isopropylamine selectivity is about 95%, Diisopropylamine selectivity approximately 3.3%, Virahol selectivity approximately 1.7%.
Embodiment 2
Fixed-bed reactor are 32 * 3mm, the stainless steel reactor of length 1350mm.The stainless steel temperature-measuring casing of ∮ 8 * 1mm is set in reactor, the trade mark that loads successively from top to bottom Beijing Chemical Research Institute's production is that the trade mark that BC-A-30 ball-type catalyst for isopropylamine and ZheJiang XinHua Chemical Engineering Co., Ltd produce is XH-3 stripe shape catalyzer, the catalyst loading total height is 960mm, wherein the ball shape catalyst loading height is that 305mm, stripe shape catalyst packing height are 655mm, and loaded catalyst is 510ml.Reaction raw materials is upper entering and lower leaving, and the material flowed out from reactor bottom enters in separator after condensing cooling, and vapor phase ammonia, hydrogen are discharged from the separator top, the bottom liquid phases timing sampling.
Temperature of reaction is 105 ℃, and reaction pressure is 0.8MPa, and the acetone liquid hourly space velocity is 0.5L acetone/(L catalyzer hour), and acetone: hydrogen: the mol ratio of ammonia is 1: 3: 3.Reaction result: acetone conversion 99%, the Isopropylamine selectivity is about 96%, Diisopropylamine selectivity approximately 2.4%, Virahol selectivity approximately 1.6%.
Embodiment 3
The catalyst loading pattern of embodiment 3-5 is as embodiment 2.
Temperature of reaction is 115 ℃, and reaction pressure is 1.0MPa, and the acetone liquid hourly space velocity is 0.7L acetone/(L catalyzer hour), and acetone: hydrogen: the mol ratio of ammonia is 1: 3: 3.Reaction result: acetone conversion 100%, the Isopropylamine selectivity is 98.6%, Diisopropylamine selectivity approximately 1.0%, Virahol selectivity approximately 0.4%.
Embodiment 4
Temperature of reaction is 125 ℃, and reaction pressure is 1.2MPa, and the acetone liquid hourly space velocity is 0.9L acetone/(L catalyzer hour), and acetone: hydrogen: the mol ratio of ammonia is 1: 3: 3.Reaction result: acetone conversion 100%, the Isopropylamine selectivity is more than 99.3%, Diisopropylamine selectivity approximately 0.52%, Virahol selectivity approximately 0.18%.
Embodiment 5
Temperature of reaction is 140 ℃, and reaction pressure is 1.5MPa, and the acetone liquid hourly space velocity is 1.1L acetone/(L catalyzer hour), and acetone: hydrogen: the mol ratio of ammonia is 1: 3: 3.Reaction result: acetone conversion 100%, the Isopropylamine selectivity is about 98.7%, Diisopropylamine selectivity approximately 1.1%, Virahol selectivity approximately 0.2%.
Claims (5)
1. a method of producing Isopropylamine, it is characterized in that, in fixed-bed reactor, load spherical nickel-base catalyst near inlet end, near exit end filling bar shaped nickel-base catalyst, the specific surface area of described spherical nickel-base catalyst and pore volume are respectively 170～220m2/g and 0.5～0.8ml/g, the specific surface area of described bar shaped nickel-base catalyst and pore volume are respectively 140～170m2/g and 0.3～0.5ml/g, the loading height of described spherical nickel-base catalyst is 1/4～1/2 of fixed-bed reactor bed height, under the existence of described two kinds of catalyzer, raw material acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate the reaction product that Isopropylamine is the master, reaction conditions is: temperature of reaction is 80～150 ℃, and reaction pressure is 0.7～1.6MPa, and the acetone solution hourly space velocity is 0.1～1.2h-1, acetone: hydrogen: the mol ratio of ammonia is 1:1～4:1～6.
2. the method for production Isopropylamine according to claim 1, it is characterized in that, described spherical nickel-base catalyst is that the trade mark that Beijing Chemical Research Institute produces is the BC-A-30 catalyst for isopropylamine, and described bar shaped nickel-base catalyst is that the trade mark that ZheJiang XinHua Chemical Engineering Co., Ltd produces is the XH-3 catalyzer.
3. the method for production Isopropylamine according to claim 1, is characterized in that, the loading height of described spherical nickel-base catalyst is 1/4～1/3 of fixed-bed reactor bed height.
4. the method for production Isopropylamine according to claim 1, is characterized in that, reactor may optionally be the upper feeding mode, or lower feeding manner.
5. according to the method for the described production Isopropylamine of claim, it is characterized in that, described method comprises the steps:
(1) Isopropylamine is synthetic:
In fixed-bed reactor, load spherical nickel-base catalyst near inlet end, near exit end filling bar shaped nickel-base catalyst, the specific surface area of described spherical nickel-base catalyst and pore volume are respectively 170～220m2/g and 0.5～0.8ml/g, the specific surface area of described bar shaped nickel-base catalyst and pore volume are respectively 140～170m2/g and 0.3～0.5ml/g, the loading height of described spherical nickel-base catalyst is 1/4～1/2 of fixed-bed reactor bed height, under the existence of described two kinds of catalyzer, raw material acetone, hydrogen and ammonia carry out the hydrogen aminating reaction and generate the reaction product that Isopropylamine is the master, reaction conditions is: temperature of reaction is 80～150 ℃, and reaction pressure is 0.7～1.6MPa, and the acetone solution hourly space velocity is 0.1～1.2h-1, acetone: hydrogen: the mol ratio of ammonia is 1:1～4:1～6,
(2) material of self-retaining bed bioreactor is cooling in the future, carries out gas-liquid separation, and the compressed machine recirculated compressed of gas is returned reactor, and liquid is sent into deammoniation tower, from tower top, isolates ammonia, delivers to reactor, is rich in the material of Isopropylamine from the tower reactor extraction;
(3) will be incorporated into the Isopropylamine tower from the material that is rich in Isopropylamine of deamination tower reactor, pass through refinery distillation from overhead extraction Isopropylamine product in the Isopropylamine tower, the material that the tower reactor extraction contains Diisopropylamine, isopropyl alcohol and water;
(4) material that the Isopropylamine tower reactor is contained to Diisopropylamine, isopropyl alcohol and water is introduced film separating system, and the organic phase containing Virahol, Diisopropylamine after the dehydration of film separating system film is used as the raw material of producing Diisopropylamine.
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| CN103965055A (en) * | 2014-05-26 | 2014-08-06 | 浙江建业化工股份有限公司 | Synthesis method of isopropyl amine |
| CN106397219A (en) * | 2016-08-26 | 2017-02-15 | 安徽昊源化工集团有限公司 | Method used for synthesizing isopropylamine via acetone hydrogenation ammoniation |
| CN110066223A (en) * | 2018-01-22 | 2019-07-30 | 北京颖泰嘉和生物科技股份有限公司 | The preparation method of 1- methoxyl group -2- propylamine |
| CN110152714A (en) * | 2018-03-20 | 2019-08-23 | 浙江建业化工股份有限公司 | A kind of catalyst and its application method producing isobutyl amine and di-iso-butylmanice |
| CN110302790A (en) * | 2019-07-26 | 2019-10-08 | 山东达民化工股份有限公司 | The n-hexylamine production technology of catalyst and preparation method thereof and application catalyst |
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| CN110152714A (en) * | 2018-03-20 | 2019-08-23 | 浙江建业化工股份有限公司 | A kind of catalyst and its application method producing isobutyl amine and di-iso-butylmanice |
| CN110152714B (en) * | 2018-03-20 | 2022-04-01 | 浙江建业化工股份有限公司 | Catalyst for producing isobutylamine and diisobutylamine and use method thereof |
| CN110302790A (en) * | 2019-07-26 | 2019-10-08 | 山东达民化工股份有限公司 | The n-hexylamine production technology of catalyst and preparation method thereof and application catalyst |
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