CN102432538A - Integrated industrial production method for producing iminostilbene by continuous catalytic deamination and catalytic dehydrogenation of 2,2'-diamino-bibenzyl - Google Patents
Integrated industrial production method for producing iminostilbene by continuous catalytic deamination and catalytic dehydrogenation of 2,2'-diamino-bibenzyl Download PDFInfo
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Abstract
The invention provides a continuous integrated industrial production method for producing iminostilbene by the catalytic deamination and catalytic dehydrogenation reaction of 2,2'-diamino-bibenzyl. The method comprises the following process flows of: mixing the 2,2'-diamino-bibenzyl with high-temperature water vapor; adding the mixture into a catalytic deamination reactor; after reaction, performing heat exchange on a reaction material through an intermediate heat exchanger; adding the reaction material into a catalytic dehydrogenation reactor; and treating the material which is taken out of the reactor to obtain the iminostilbene. The method is a continuous integrated process of the catalytic deamination and catalytic dehydrogenation reaction, and has the characteristics of simple reaction process, low energy consumption, small equipment investment and the like.
Description
Technical field
The invention belongs to the chemical reaction engineering technical field, specifically, relate to the catalysis deamination and the catalytic dehydrogenation serialization industrial process that prepare a kind of medicine intermediate iminostilbene.
Background technology
Iminostilbene (5H-dibenzo [b, f] azepine is called for short IS) is a kind of important medicinal intermediates, is mainly used in the synthetic of Carbamzepine and O'Casey equality medicine.
With the synthetic imido stilbene of iminodibenzyl (10,11-dihydro-5H-dibenzo [b, f] azepine is called for short IDB) is that the method that extensively adopts is gone up in industry, mainly contains bromination method, liquid-phase catalysis dehydriding and vapor catalytic dehydrogenation method.Bromination method is the commercial run of production iminostilbene the earliest; Iminodibenzyl prepares the method for iminostilbene through multisteps such as acidylate, bromination, dehydrobromination, deacylated tRNAs; There are drawbacks such as transformation efficiency is low, dopant species is many, waste time and energy in this method, and quality product is not high.Catalytic dehydrogenation prepares the imido stilbene under the iminodibenzyl liquid-phase condition, and temperature of reaction is low, and product yield is higher, but exist to adopt noble metal catalyst and loss serious, hydrogen consuming acceptor, defective such as product postprocessing is more loaded down with trivial details.The iminodibenzyl vapor catalytic dehydrogenation prepares imido stilbene method, and it is simple to have a technical process, and the by product kind is few, easily separated, and quality product is high, can be used for producing advantages such as no bromine Carbamzepine, is the best approach of production iminostilbene.
With 2; 2 '-the synthetic iminodibenzyl of diamino-bibenzyl (being called for short DADB) is that the method that extensively adopts is gone up in industry; Mainly contain 2,2 '-the pyrolysis deamination, 2,2 of diamino-bibenzyl diacid salt '-diamino-bibenzyl liquid-phase catalysis deamination, 2; 2 '-the SPA deamination and 2,2 of diamino-bibenzyl '-diamino-bibenzyl gas phase catalysis deamination method.2,2 '-the pyrolysis deamination method of diamino-bibenzyl diacid salt is the method for synthetic iminodibenzyl the earliest, this method technology is simple, but raw material and product decompose seriously in the reaction engineering, cause yield lower, and quality product is relatively poor.2,2 '-diamino-bibenzyl liquid-phase catalysis deamination method quality product is better, but yield is lower.2,2 '-the SPA deamination method quality of diamino-bibenzyl is better, and yield is also higher, but higher to equipment requirements.2,2 '-diamino-bibenzyl gas phase catalysis deamination method, it is simple to have a technical process, and yield is high, and quality product is high, and production unit is required advantages such as low, is the best approach of producing iminodibenzyl.
Disclose a kind of 2 in the document JP 53098984; 2 '-the diamino-bibenzyl prepares the iminodibenzyl working method, uses internal diameter 22mm, the fixed-bed reactor of long 1000mm; Select for use H2, CO2, water vapor etc. as diluents; With the toluene dissolving raw material, after vaporization, get into the catalytic bed reaction, reaction is after condenser condenses is separated out product.But belong to laboratory testing rig.
The chemical synthesis process that a kind of iminodibenzyl prepares iminostilbene is disclosed among the document CN 101307021A; Adopt fixed-bed reactor; Electrically heated makes the catalytic bed temperature be increased to 400-600 ℃; The fused iminodibenzyl is brought catalytic bed into through high-pressure water vapor, and the reaction back gets into the device that water coolant is housed, and recrystallization obtains product behind the mixed solution evaporate to dryness moisture content that obtains.This method adopts the electrically heated catalytic bed, and energy consumption is very high when using in the industry; Adopt water vapor to carry raw material and advance reactor drum, the raw material inlet amount is regulated difficulty; Reactor diameter 30mm only can't directly apply to industrial production in addition.
Disclose the production technique that a kind of iminodibenzyl prepares iminostilbene in the document US 3531466, proposed the base metal dehydrogenation catalyst, adopted tubular reactor; Temperature of reaction is between 300～700 ℃; Normal pressure or negative-pressure operation utilize water vapor to carry raw material, and through adding the dividing potential drop of nitrogen reduction iminodibenzyl; The whole condensations of reaction after product, mixed solution obtains product through recrystallization.This method employing water vapor carries raw material and advances reactor drum, and the raw material inlet amount is regulated difficulty; Adopt nitrogen conditioned reaction thing dividing potential drop, caused the dehydrogenated tail gas calorific value significantly to descend, and under the negative-pressure operation condition, make the load of tail-gas compressor increase; Reactor diameter 30mm only belongs to laboratory testing rig in addition.
Disclose the working method that a kind of iminodibenzyl prepares the imido stilbene in the document JP 55017330, prepared the compound metal oxide catalyst, use temperature 350-650 ℃, reaction system can be carried out under normal pressure or reduced pressure.Reactor diameter 16mm adopts electrically heated, only belongs to laboratory testing rig.
Disclose a kind of iminodibenzyl catalytic dehydrogenation among the document CN 102120729A and produced the industrial method of iminostilbene.The technical process of this method be reaction mass through heat fused with get into dehydrogenation reactor after high-temperature water vapor mixes; Dehydrogenation reaction is to comprise axially or in the radial fixed-bed reactor carrying out of at least two catalytic bed at one; Indirect or the direct heating reaction mass of high-temperature water vapor is set between two catalytic bed; The material that comes out from reactor drum carries out heat exchange recovery heat through an interchanger; Get into the absorption tower have interchanger subsequently, itself or bubble absorbing tower or spray absorber, the solvent that has absorbed reaction product is through acquisition product iminostilbenes such as evaporation, crystallizations.
In the method for above-mentioned production iminostilbene, do not find as yet by 2,2 in sum, '-continuous integrated industrial working method that diamino-bibenzyl continuous catalysis deamination, catalytic dehydrogenation are produced iminostilbene; Simultaneously; Iminodibenzyl prepare imido stilbene and 2,2 '-the diamino-bibenzyl prepares water vapor that iminodibenzyl all adopted high molar ratio as thinner and thermal barrier, the preparation method of its stepwise reaction; Water vapor is only participated in primary first-order equation; Utilization ratio is not high, causes energy consumption high, and many etc. the deficiencies of utility appliance.
Summary of the invention
The present inventor is through research, for 2,2 '-diamino-bibenzyl catalysis deamination and dehydrogenation production iminostilbene; Find a kind of continuous incorporate industrial process, the technical process of this method is: reaction mass 2,2 '-the diamino-bibenzyl is through heat fused; Deliver to mixing tank by volume pump and mix, get into the deamination reaction device then, 2 with high-temperature water vapor; 2 '-transformation efficiency of diamino-bibenzyl is 90%～99%, generates iminodibenzyl and minor by-products, reacted reaction mass is through the intermediate heat heat exchange; Get into dehydrogenation reactor subsequently; Iminodibenzyl has 60%～90% transformation efficiency, generates product iminostilbene and by products such as acridine, methylacridine, and the material that comes out from reactor drum obtains product iminostilbene, intermediate product iminodibenzyl and other sub product after condensation-crystallization or solvent absorbing etc. are handled.
Therefore, primary and foremost purpose of the present invention just be to provide a kind of 2,2 '-continuous incorporate industrial process that iminostilbene is produced in diamino-bibenzyl gas phase catalysis deamination and catalytic dehydrogenation.
The technical issues that need to address of the present invention are: supply in a kind of industry feasible; More compact simple 2; 2 '-diamino-bibenzyl gas phase catalysis deamination and catalytic dehydrogenation produce the continuous integral manufacturing technique of iminostilbene; Realize the catalyzed reaction of highly selective, cut down the consumption of energy the accords with production actual needs simultaneously;
Design of the present invention is such:
1, adopting water vapor is thermal barrier, helps reducing the dividing potential drop effect of reactant, promotes catalysis deamination and these two enforcements that increase volumetric reaction of catalytic dehydrogenation; Reduced the variation significantly of catalysis deamination and catalytic dehydrogenating reaction temperature simultaneously, helped reaction and carry out.In addition, the adding of water vapor can effectively advance water-gas reaction, has avoided the knot charcoal of catalyzer, significantly improves life of catalyst;
2, adopt the continuous reaction process of catalysis deamination and catalytic dehydrogenation, water vapor through deamination catalyzer and dehydrogenation catalyst, is participated in reaction process twice continuously, has improved the utilization ratio of water vapor, thereby has significantly reduced system-wide energy consumption;
3, adopt the radial reactor technology; Or adopt thin bed axial flow reactor technology, and effectively reduce bed pressure drop, help under low pressure more; Promote the above-mentioned enforcement that increases the volumetric reaction process, more meet catalysis deamination and the catalytic dehydrogenation integral process requirement of connecting continuously;
4, the deamination catalyzer adopts the alumina series catalyzer, and it is that Primary Catalysts, potassium oxide are the Fe-series catalyst of promotor that dehydrogenation catalyst adopts red stone;
5, the intermediate product iminodibenzyl can recycle, and gets into the dehydrogenation reactor reaction again.
According to above-mentioned design, the present invention proposes following technical scheme:
A kind of 2,2 '-diamino-bibenzyl continuous catalysis deamination, dehydrogenation produce the industrialized preparing process of iminostilbene.This technical process is 2; 2 '-the diamino-bibenzyl is through heat fused; Deliver to mixing tank by volume pump and mix with high-temperature water vapor, get into the deamination reaction device then, reacted reaction mass improves temperature through intermediate heat; Get into dehydrogenation reactor subsequently, the material that comes out from dehydrogenation reactor obtains product iminostilbene, intermediate product iminodibenzyl and other sub product after condensation-crystallization or solvent absorbing etc. are handled.The intermediate product iminodibenzyl can recycle, and mixes with the deamination reaction product, after intermediate heat promotes temperature, gets into dehydrogenation reactor.
Of the present invention 2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce in the method for iminostilbene; The deamination reaction device adopts radial reactor or axial flow reactor, to use radial reactor preferable, fills the deamination catalyzer of aluminum oxide series in the bed.Reaction mass is got into by reactor head, flows out from reactor bottom.Deamination reaction of the present invention can adopt the deamination catalyzer of alumina series.
Of the present invention 2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce in the method for iminostilbene; Dehydrogenation reactor adopts radial reactor or axial flow reactor; To use radial reactor preferable, filling with the red stone in the bed is the base metal dehydrogenation catalyst of main active ingredient.Reaction mass is got into by reactor head, flows out from reactor bottom.It is that main active component, potassium oxide are the dehydrogenation catalyst of ancillary component that dehydrogenation reaction of the present invention can adopt with the red stone.
Of the present invention 2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce in the technology of iminostilbene; Between deamination reaction device and the dehydrogenation reactor intermediate heat is set; The deamination reaction product gets into dehydrogenation reactor then through improving the reaction mass temperature with the high-temperature water vapor heat exchange.
Of the present invention 2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce in the method for iminostilbene, water vapor and 2,2 '-mol ratio of diamino-bibenzyl is 200～400; 2,2 '-weight space velocity of diamino-bibenzyl in the deamination reaction device is 0.01～1.00h
-1, the deamination reaction temperature is 300～500 ℃, reaction pressure is 50～300kPa, 2,2 '-scope of the transformation efficiency 90%～99% of diamino-bibenzyl, the selectivity of intermediate product iminodibenzyl is 95%～98%; The weight space velocity of iminodibenzyl in dehydrogenation reactor is 0.02～2.0h
-1, the dehydrogenation reaction temperature is 380～600 ℃, and reaction pressure is 30～250kPa, and the transformation efficiency of iminodibenzyl is 60%～90%, and the selectivity of reaction product iminostilbene is 65%～90%.
Present method adopts 2,2 '-the continuous incorporate industrial manufacture process of diamino-bibenzyl catalysis deamination and dehydrogenation production iminostilbene, reaction process is simple; Through continuous catalysis deamination and catalytic dehydrogenation technology, water vapor is participated in two secondary responses, and its utilization ratio is doubled, and greatly reduces energy consumption; Adopt incorporate continuous production processes, reduced a process furnace and a cover finishing apparatus, significantly reduced facility investment.
Description of drawings
Fig. 1 is of the present invention 2,2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce the schematic flow sheet of iminostilbene.
Fig. 2 intermediate product iminodibenzyl of the present invention round-robin 2,2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce the schematic flow sheet of iminostilbene.
Among the figure: 1, DADB head tank 2, DADB volume pump 3, DADB mixing tank 4, process furnace 5, deamination reaction device 6, intermediate heat 7, dehydrogenation reactor 8, IDB head tank 9, IDB volume pump 10, IDB mixing tank
The practical implementation method
Below in conjunction with accompanying drawing the present invention is done further explanation.
In Fig. 1: 2,2 '-the diamino-bibenzyl sends into DADB head tank 1, and fusing is transported to DADB mixing tank 3 through DADB volume pump 2 with it then under the heating of water vapor; Water or water vapor are heated to be high-temperature water vapor in process furnace 4, at first deliver to the product of heating deamination reaction in the intermediate heat 6, deliver to DADB mixing tank 3 after the heat exchange.In DADB mixing tank 3; 2; 2 '-after mixing, diamino-bibenzyl and high-temperature water vapor reach 300～500 ℃ deamination reaction temperature, and get into deamination reaction device 5 then and carry out the catalysis deamination reaction, reaction product gets into intermediate heat 6 and is heated to 380～600 ℃ dehydrogenation reaction temperature by high-temperature water vapor; Get into dehydrogenation reactor 7 and carry out catalytic dehydrogenating reaction; Reaction product gets into aftertreatment, through processes such as condensation-crystallization or solvent absorbing obtain raw material 2,2 '-diamino-bibenzyl, product iminostilbene, intermediate product iminodibenzyl and other sub product.
Fig. 2 flow process with like Fig. 1 basically identical, only increased recycling of dehydrogenation by product iminodibenzyl.The dehydrogenation by product that obtains is sent into IDB head tank 8 after aftertreatment is reclaimed; Under the heating of water vapor, be melted; Through IDB volume pump 9 it is transported to IDB mixing tank 10 then; Mix with the deamination product that deamination reaction device 5 comes out, after intermediate heat 6 improves temperature, get into reaction in the dehydrogenation reactor 7 then.
In the present invention, the deamination catalyzer can adopt the catalyzer of the gama-alumina series of reporting like document, the serial catalyzer of red stone that dehydrogenation catalyst can adopt market to sell.2,2 '-weight space velocity of diamino-bibenzyl in deamination reaction device 5 is 0.01～1.0h
-1, the weight space velocity of iminodibenzyl in dehydrogenation reactor 7 is 0.02～2.0h
-1
[embodiment 1]
2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce iminostilbene and carry out with the technical process of Fig. 1, water vapor and 2,2 '-mol ratio of diamino-bibenzyl is 300; 2; 2 '-the diamino-bibenzyl sends into DADB head tank 1, and fusing is transported to DADB mixing tank 3 through DADB volume pump 2 with it then under the heating of water vapor; Water is heated to 580 ℃ in process furnace 4, deliver to the product of heating deamination reaction in the intermediate heat 6, delivers to DADB mixing tank 3 after the heat exchange.In DADB mixing tank 3,2,2 '-after mixing, diamino-bibenzyl and high-temperature water vapor reach 420 ℃ deamination reaction temperature; Get into deamination reaction device 5 then and carry out the catalysis deamination reaction; Deamination reaction device 5 inlet pressures are 250kPa, and reaction product gets into intermediate heat 6 and is heated to 550 ℃ dehydrogenation reaction temperature by high-temperature water vapor, gets into dehydrogenation reactor 7 and carries out catalytic dehydrogenating reaction; Dehydrogenation reactor 7 inlet pressures are 200kPa, and reaction product gets into treatment and finishing section subsequently.Deamination reaction device 5 is the radial reactor pattern with dehydrogenation reactor 7, and the deamination catalyzer adopts gamma-alumina catalyst, and dehydrogenation catalyst adopts the C105 dehydrogenation catalyst.2,2 '-weight space velocity of diamino-bibenzyl in deamination reaction device 5 is 0.07h
-1, the weight space velocity of iminodibenzyl in dehydrogenation reactor 7 is 0.15h
-1Reaction result is seen table 2.
[embodiment 2]
2; 2 '-diamino-bibenzyl gas phase catalysis deamination, catalytic dehydrogenation produce iminostilbene and carry out with the technical process of Fig. 2, water vapor and 2,2 '-mol ratio of diamino-bibenzyl is 400; 2; 2 '-the diamino-bibenzyl sends into DADB head tank 1, and fusing is transported to DADB mixing tank 3 through DADB volume pump 2 with it then under the heating of water vapor; Water vapor is heated to 540 ℃ in process furnace 4, deliver to the product of heating deamination reaction in the intermediate heat 6, delivers to DADB mixing tank 3 after the heat exchange.In DADB mixing tank 3; 2,2 '-after mixing, diamino-bibenzyl and high-temperature water vapor reach 400 ℃ deamination reaction temperature, and get into deamination reaction device 5 then and carry out the catalysis deamination reaction; Deamination reaction device 5 inlet pressures are 90kPa; Reaction product is mixed with the intermediate product iminostilbene of recovery, gets into intermediate heat 6 again and is heated to 520 ℃ dehydrogenation reaction temperature by high-temperature water vapor, gets into dehydrogenation reactor 7 and carries out catalytic dehydrogenating reaction; Dehydrogenation reactor 7 inlet pressures are 60kPa, and reaction product gets into treatment and finishing section subsequently.The intermediate product iminodibenzyl is sent into IDB head tank 8, under the heating of water vapor, is melted, and through IDB volume pump 9 it is transported to IDB mixing tank 10 then and mixes with the deamination product that deamination reaction device 5 comes out.Deamination reaction device 5 is the radial reactor pattern with dehydrogenation reactor 7, and the deamination catalyzer adopts gamma-alumina catalyst, and dehydrogenation catalyst adopts Styromax 5 type dehydrogenation catalysts.2,2 '-weight space velocity of diamino-bibenzyl in deamination reaction device 5 is 0.02h
-1, the weight space velocity of iminodibenzyl in dehydrogenation reactor 7 is 0.08h
-1Reaction result is seen table 2.
Table 2:
Adopt method of the present invention, compared with prior art have the following advantages:
1. adopt 2,2 '-continuous incorporate industrial process that iminostilbene is produced in diamino-bibenzyl catalysis deamination and dehydrogenation, reaction process is more compact simply;
2. comprehensive energy consumption is low, adopts the continuous processing of catalysis deamination reaction, catalytic dehydrogenating reaction, and water vapor is participated in two secondary responses, and its utilization ratio is doubled, and energy consumption reduces greatly;
3. facility investment is few, adopts the continuous processing of catalysis deamination reaction and catalytic dehydrogenating reaction, has saved a cover process furnace and a separation system, has significantly reduced facility investment.
Claims (4)
1. one kind 2; 2 '-diamino-bibenzyl catalysis deamination and catalytic dehydrogenation produce the continuous integrated industrial working method of iminostilbene, it is characterized in that 2; 2 '-the diamino-bibenzyl is through heat fused; Deliver to mixing tank (3) by volume pump (2) and mix with high-temperature water vapor, get into deamination reaction device (5) then, reacted reaction mass is through intermediate heat (6) heat exchange; Get into dehydrogenation reactor (7) subsequently, the material that comes out from dehydrogenation reactor (7) obtains product iminostilbene, intermediate product iminodibenzyl and other sub product through aftertreatment.
2. the method for claim 1 is characterized in that, described water vapor is participated in catalysis deamination reaction and catalytic dehydrogenating reaction continuously.
3. the method for claim 1; It is characterized in that the deamination processing condition are: water vapor and 2,2 '-mol ratio of diamino-bibenzyl is 200～400; The temperature in of deamination reaction device (5) is 300～500 ℃; Reaction pressure is 300～50kPa, 2,2 '-weight space velocity of diamino-bibenzyl in deamination reaction device (5) is 0.01～1.0h
-1
4. the method for claim 1 is characterized in that, the dehydrogenating technology condition is: the temperature in of dehydrogenation reactor (7) is 380～600 ℃, and reaction pressure is 250～30kPa, and iminodibenzyl weight space velocity of (7) in dehydrogenation reactor is 0.02～2.0h
-1
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Cited By (3)
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| CN103275006A (en) * | 2013-05-29 | 2013-09-04 | 陈建国 | Method for synthesizing iminostilbene intermediate of carbamazepine |
| CN105439954A (en) * | 2014-09-25 | 2016-03-30 | 中国石油化工股份有限公司 | One-step synthesis method of iminostilbene |
| CN106588774A (en) * | 2016-11-12 | 2017-04-26 | 兰州大学 | Method for catalytic synthesis of iminodibenzyl |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103275006A (en) * | 2013-05-29 | 2013-09-04 | 陈建国 | Method for synthesizing iminostilbene intermediate of carbamazepine |
| CN103275006B (en) * | 2013-05-29 | 2014-12-03 | 陈建国 | Method for synthesizing iminostilbene intermediate of carbamazepine |
| CN105439954A (en) * | 2014-09-25 | 2016-03-30 | 中国石油化工股份有限公司 | One-step synthesis method of iminostilbene |
| CN106588774A (en) * | 2016-11-12 | 2017-04-26 | 兰州大学 | Method for catalytic synthesis of iminodibenzyl |
| CN106588774B (en) * | 2016-11-12 | 2019-05-14 | 兰州大学 | A method of catalyzing and synthesizing iminodibenzyl |
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Application publication date: 20120502 |