CN106146345B - The method that adipic acid liquid phase method produces adiponitrile - Google Patents
The method that adipic acid liquid phase method produces adiponitrile Download PDFInfo
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Abstract
A kind of method of adipic acid liquid phase method production adiponitrile, catalyst is solid phosphoric acid catalyst, puts into adipic acid and diluent into reaction kettle, and when reaction heats and stirs raw material, is passed through ammonia after reaching certain temperature, product is generated after reacting after a while.The present invention is a kind of novel green synthetic method of adiponitrile production development, and catalytic effect is improved while a variety of disadvantages that traditional catalyst brings are avoided using solid phosphoric acid catalyst.
Description
Technical field
The present invention relates to a kind of technology of adipic acid liquid phase ammoniation process production adiponitrile, a kind of green solid is used in production
Phosphoric acid catalyst.
Background technology
Adiponitrile is the important source material of nylon66 fiber, there is the substantial amounts of market demand at home.Wherein, adipic acid catalytic ammoniation method
It is an essential industry chemical industry skill in adiponitrile production.Adipic acid catalytic ammoniation method is adipic acid and ammonia in dehydration catalyst
The lower reaction of effect generates thick adiponitrile, the technique that finished product is obtained after rectifying.According to the difference of adipic acid physical state, the technique is again
It is divided into adipic acid liquid phase method and adipic acid vapor phase method.Wherein, generally at 280 DEG C or so, vapor phase method is the reaction temperature of liquid phase method
350℃-420℃.It is different from vapor phase method, in order to reduce the generation of accessory substance and tar in liquid phase method, also additionally to add dilution
Agent maintains the uniformity of temperature of reaction system.In addition, liquid phase method, since technological process is relatively simple, ring-type impurity is less, energy consumption
It is low, more by industrial favor.But due to adipic acid selling at exorbitant prices, do not possess cost advantage, in the gradual quilt nineties in last century
Industrial quarters is eliminated.However, with the falling of adipic acid price, following adipic acid liquid phase method but also with the possibility restarted, on
The green high-efficient catalyst research of the technique causes the attention of people again.
The reaction of adipic acid liquid phase method is roughly divided into two step of neutralization reaction and dehydration, as follows：
HOOC(CH2)4COOH+2NH3→H4NOC(CH2)4CONH4
H4NOC(CH2)4CONH4→NC(CH2)4CN+4H2O
Wherein dehydration is a process being progressively dehydrated, and has many intermediate product generations.Specific reaction process
Complex and academia is still disputable, is just no longer discussed in detail herein.
Common catalyst is the liquid catalysts such as phosphoric acid, phosphate in adipic acid liquid phase method.But this kind of catalyst has
Many disadvantages.First, substantial amounts of phosphoric acid, phosphate can produce reactor certain corrosiveness, influence normal production.
Secondly, this kind of liquid catalyst is soluble in reaction system, with the progress of reaction, is easily lost in, is needed continually in production
Ground supplements, and adds production cost.In addition, according to U.S.Pat.5, described in 202,455, in the reaction, phosphoric acid and phosphate are all
Polyphosphoric acid can be generated, is deposited in wall of reactor, influences the heat transfer of external heat source.In order to solve the problems, such as to conduct heat, DE734,
558 have been mixed into a certain amount of adsorbent in phosphoric acid.Adsorbent can be from diatomite, silica, alumina, clay, molecular sieve
In arbitrarily select.After the addition, there is no polyphosphoric acid to be deposited in wall of reactor.But due to unknown, the catalysis
Agent so far there are no all industrial applications.Simultaneously as adipic acid liquid phase method in the nineties in last century just progressively by industrial quarters institute
Eliminate, the research on its catalyst has been at dead state, rarely seen to be reported in research.
Compared to liquid catalysts such as traditional phosphoric acid, phosphates, solid phosphoric acid catalyst has similar catalytic effect,
In addition it can also overcome the various disadvantages of liquid catalyst.Solid phosphoric acid catalyst can slowly discharge phosphoric acid in reaction, and phosphoric acid exists
Concentration in system is low, and the corrosion to reactor is smaller.Polyphosphoric acid growing amount is less at the same time, and heat transfer can also be carried out preferably.
After reaction, catalyst filtration is come out, is also used multiple times after fired.It is worth noting that, solid phosphoric acid catalyst
So far only applied, be not yet present in adipic acid liquid phase method in adipic acid gas-phase process.
The content of the invention
It is an object of the invention to provide a kind of a kind of novel green production skill of adipic acid liquid phase method production adiponitrile technology
Art, avoids the disadvantages such as polymerization, coking that traditional liquid phosphoric acid catalyst brings, while improves product yield, and because of catalyst
Recyclable recycling, better economy.
The present invention provides a kind of method of adipic acid liquid phase method production adiponitrile, and catalyst is solid phosphoric acid catalyst, to
Put into adipic acid and diluent in reaction kettle, when reaction heats and stirs raw material, ammonia is passed through after reaching certain temperature, by one
Product is generated after section time response.
The method of adipic acid liquid phase method production adiponitrile of the present invention, these, it is preferred to which the solid phosphoric acid is urged
Agent preparation method is：After dry 1-2h, dry diatomite is soaked under 100-140 DEG C of baking oven for a certain amount of diatomite
Stain stirs 6-12h, then in the excessive phosphoric acid solution of 55%-95% and the aluminum sulfate solution mixed solution of 15-25wt%
Stand 6-12h；Mixed solution is centrifuged after standing, when obtained sediment dry 6-12 in 100-140 DEG C of baking oven is small；It is dry
Sediment is placed in pipe type calciner afterwards, N2In 300 DEG C of -700 DEG C of roasting 1-2h under protective condition；By its tabletting after cooling
Shaping, obtains the particle of 10-50 mesh after sieve screens, and forms solid phosphoric acid catalyst.
The method of adipic acid liquid phase method production adiponitrile of the present invention, wherein, diluent is preferably adiponitrile, penta 2
One or more in nitrile and pimelic dinitrile, diluent are more preferably adiponitrile.
The method of adipic acid liquid phase method production adiponitrile of the present invention, wherein, phosphoric acid solution and diatomaceous quality
Than being the 10%-15% of diatomite quality for 10-15, the addition of sulfate.
The method of adipic acid liquid phase method production adiponitrile of the present invention, wherein, the mass ratio of adipic acid and diluent
Preferably 1:2.
The method of adipic acid liquid phase method of the present invention production adiponitrile, wherein, solid phosphoric acid dosage be preferably oneself two
The 1%-2.5% of acid and diluent gross mass.
The method of adipic acid liquid phase method of the present invention production adiponitrile, wherein, speed of agitator is preferably during reaction
1000-2000r/min。
The method of adipic acid liquid phase method of the present invention production adiponitrile, wherein, heating-up temperature is preferably 260 during reaction
℃-280℃。
The method of adipic acid liquid phase method of the present invention production adiponitrile, wherein, the ammonia flow that when reaction is passed through is excellent
Elect 150L/h-400L/h as.
The method of adipic acid liquid phase method production adiponitrile of the present invention, wherein, the reaction time is preferably 0.5-2h.
The effect of the present invention：
The present invention during the application of solid phosphoric acid catalyst, by ammonia from reaction kettle can be brought into by the water of dehydration generation
Condenser system, and then be collected.Since ammonia flow is significantly excessive in appraisement system, even if not adding catalyst, neutralize
Also quickly, when proceeding to 60min, neutralization reaction fundamental reaction is complete for the speed of reaction.At this time, dehydrating amount is bigger represents that dehydration is anti-
Should be more complete, the yield of adiponitrile is higher.Therefore, the dehydration rate (ratio of actual dehydrating amount and theoretical dehydrating amount of 60min is chosen
Value) size characterize the catalytic effect of catalyst.
Experiment finds that when not adding catalyst, dehydration rate only has 18%-41%；Adding traditional liquid phosphoric acid catalysis
After agent, dehydration rate lifting to 46%-85%；When adding solid phosphoric acid, dehydration rate has reached 57%-95%.
Embodiment
Elaborate below to the embodiment of the present invention：The present embodiment is carried out lower premised on technical solution of the present invention
Implement, give detailed embodiment and process, but protection scope of the present invention is not limited to following embodiments, following implementation
The experimental method of actual conditions is not specified in example, usually according to normal condition.
Diatomite support drying condition
In the present invention, diatomite drying condition is not particularly limited, usually by a certain amount of diatomite in 100-140
DEG C dry 1-2h, preferably carrier is in 120 DEG C of dry 2h；
If drying temperature is less than 100 DEG C, since drying temperature is too low, causes dry insufficient, or extend drying time；
And drying temperature is more than 140 DEG C, since drying temperature is excessive, the wasting of resources is caused, has no other beneficial effects.
If drying time is less than 1h, since drying time is too short, cause to dry insufficient, residual moisture；And when drying
Between be more than 2h, since drying time is long, cause the wasting of resources, have no other beneficial effects.
Phosphoric acid solution concentration
In the present invention, phosphoric acid solution concentration is not particularly limited, usual phosphoric acid solution is 55-95wt%, preferably
That phosphoric acid solution is 65-85wt%, if phosphoric acid solution is less than 55wt%, since phosphoric acid concentration is too low, cause to impregnate it is insufficient,
Dipping effect is bad, and phosphoric acid solution since phosphoric acid concentration is excessive, causes dipping to generate non-targeted product more than 95wt%, right
Catalytic effect impacts, have no other beneficial effects.
Aluminum sulfate solution concentration
In the present invention, aluminum sulfate solution concentration is not particularly limited, usual aluminum sulfate solution is 15-25wt%, such as
Fruit aluminum sulfate solution is less than 15wt%, since sulfuric acid aluminum concentration is too low, causes dipping effect undesirable, load capacity is low, and sulfuric acid
Aluminum solutions due to aluminum sulfate excessive concentration, impact phosphate impregnation effect, have no other beneficial effects more than 25wt%.
Metallic element aluminium is introduced in dipping solution, catalyst forms the phosphate of definite composition after high-temperature roasting,
Each element is intermolecular synergistic effect.In addition, after introducing a certain amount of metallic element aluminium, the acid content of high acid strength in catalyst
Increase, reactivity increase.
The mixing time of mixed solution
In the present invention, the mixing time of mixed solution is not particularly limited, usually stirs 6-12h；If step (1)
In mixing time be less than 6h, since the time is too short, cause to stir insufficient, reaction is incomplete, and during the stirring of mixed solution
Between more than 12h, cause the time to waste, have no other beneficial effects.
The time of repose of mixed solution
In the present invention, the time of repose in mixed solution is not particularly limited, usually stands 6-12h；If step
(1) time of repose in is less than 6h, since the time is too short, causes the reaction time insufficient, influences catalytic effect, and in mixed solution
Time of repose more than 12h, cause the time to waste, have no other beneficial effects.
The drying precipitate condition obtained after centrifugation
The drying precipitate condition obtained after centrifugation is not particularly limited in the present invention, what is usually obtained after centrifugation is heavy
Starch drying condition is in 100-140 DEG C of dry 6-12h；
If drying temperature is less than 100 DEG C, since drying temperature is too low, cause dry insufficient；And drying temperature is more than
140 DEG C, since drying temperature is excessive, the wasting of resources is caused, has no other beneficial effects.
If drying time is less than 6h, since drying time is too short, cause dry insufficient；And drying time is more than 12h,
Since drying time is long, the wasting of resources is caused, has no other beneficial effects.
Roasting condition
Roasting condition is not particularly limited in the present invention, usually in 300 DEG C of -700 DEG C of roasting 1-2h；
If calcination temperature is less than 300 DEG C, since calcination temperature is too low, cause decomposition reaction insufficient；And calcination temperature
More than 700 DEG C, since calcination temperature is excessive, the wasting of resources is caused, and easily generates other accessory substances, has no other beneficial to effect
Fruit.
If roasting time is less than 1h, since roasting time is too short, cause decomposition reaction insufficient；And roasting time is more than
2h, since roasting time is long, causes the wasting of resources, and easily generates other accessory substances, has no other beneficial effects.
Solid phosphoric acid catalyst particle
In the present invention, solid phosphoric acid catalyst particle is not particularly limited, the particle for usually screening 10-50 mesh is formed
Solid phosphoric acid catalyst；
If solid phosphoric acid catalyst is less than 10 mesh, due to too small, cause to be not easily recycled after the reaction；And solid phosphoric acid is urged
Agent is more than 50 mesh, due to excessive, cause effectively to be catalyzed area reduction, has no other beneficial effects.
Diluent
In the present invention, the species of diluent is not particularly limited, the usual diluent can be enumerated as adiponitrile,
One or more in glutaronitrile and pimelic dinitrile.
Phosphoric acid and sulfuric acid salt quality amount ratio in mixed solution
In the present invention, phosphoric acid in mixed solution and sulfuric acid salt quality amount ratio are not particularly limited, usual phosphoric acid is molten
Liquid is 10-15 with diatomaceous mass ratio, and the addition of sulfate is the 10%-15% of diatomite quality.
The mass ratio of adipic acid and diluent
In the present invention, the mass ratio of adipic acid and diluent is not particularly limited, usual adipic acid and diluent
Mass ratio is 1:2；
If the mass ratio of adipic acid and diluent is less than 1:2, since the dosage of adipic acid is very few, cause reactant to subtract
Few, yield reduces, and the mass ratio of adipic acid and diluent is more than 1:2, since adipic acid dosage is excessive, cause to waste, and instead
Answer that thing concentration is higher, and dispersion effect is bad, have no other beneficial effects.
Solid phosphoric acid dosage
In the present invention, solid phosphoric acid dosage is not particularly limited, usual solid phosphoric acid dosage is adipic acid and dilution
The 1%-2.5% of agent gross mass；
If solid phosphoric acid dosage is less than the 1% of adipic acid and diluent gross mass, since solid phosphoric acid dosage is too small, make
Bad into catalytic effect, reaction yield reduces, and solid phosphoric acid dosage is more than the 2.5% of adipic acid and diluent gross mass, by
It is excessive in solid phosphoric acid dosage, cause to waste, have no other beneficial effects.
Speed of agitator during reaction
Speed of agitator is not particularly limited when in the present invention, to reaction, and speed of agitator is 1000- when usually reacting
2000r/min；
Speed of agitator is less than 1000r/min during reaction, and speed of agitator is too small during due to reaction, causes the used time long, and instead
Thing is answered to be uniformly distributed；And speed of agitator is more than 2000r/min when reacting, due to reaction when speed of agitator it is excessive, cause
The wasting of resources, has no other beneficial effects.
Heating-up temperature during reaction
Heating-up temperature is not particularly limited when in the present invention, to reaction, and heating-up temperature is 260 DEG C -280 when usually reacting
℃；
If reaction when heating-up temperature be less than 260 DEG C, due to reaction when heating-up temperature it is too low, cause reaction temperature inadequate,
React insufficient；And when reacting heating-up temperature be more than 280 DEG C, due to reaction when heating-up temperature it is excessive, side reaction may be generated, and
Without other beneficial effects.
The ammonia flow being passed through during reaction
In the present invention, the ammonia flow being passed through during reaction is not particularly limited, the ammonia flow being passed through when usually reacting
Measure as 150L/h-400L/h.
If the ammonia flow being passed through during reaction is less than 150L/h, since the ammonia flow being passed through during reaction is too small, cause
Reaction speed slows down；, can since the ammonia flow being passed through during reaction is excessive and the ammonia flow being passed through when reacting is more than 400L/h
A part of heat can be taken away, cause system unstable, and wasted raw material, have no other beneficial effects.
Reaction time
In the present invention, the reaction time is not particularly limited, the usual reaction time is 0.5-2h；If the reaction time is small
In 0.5h, since the reaction time is too short, cause to react insufficient；And the reaction time is more than 2h, since the reaction time is long, cause
The wasting of resources, and accessory substance is easily generated, have no other beneficial effects.
【Embodiment 1】
10g diatomite is dried into 2h under 120 DEG C of baking oven；Then it is 75% to be impregnated in 120g mass percent concentrations
In phosphoric acid solution, the aluminum sulfate solution that 6g mass percent concentrations are 20% is added, forms mixed solution；Mixed solution is stirred
12h is stood after 12h；Mixed solution is centrifuged, obtained sediment be placed in 120 DEG C of baking ovens dry 12 it is small when；After dry
Sediment be placed in pipe type calciner, be continually fed into N2, and 2h is roasted at 400 DEG C, ultimately form solid phosphoric acid catalysis
Agent；By the solid phosphoric acid catalyst compression molding after roasting, the particle of 20-40 mesh is obtained after sieve screens.
Solid phosphoric acid catalyst is in adipic acid liquid phase method using as follows：
In foregoing adipic acid liquid phase method technique, the input amount of adipic acid is 73g, and the input amount of adiponitrile is 146g,
Solid phosphoric acid input amount accounts for the 1.4% of the total input amount of reactant, ammonia flow 150L/h, speed of agitator 1500r/min, instead
It is 270 DEG C to answer temperature.It was found that after reaction 60min, dehydration rate reaches 73.6%.
【Embodiment 2】
Phosphoric acid concentration in the preparation process of 1 solid phosphoric acid of embodiment is changed to mass percent concentration 75%, phosphoric acid is molten
Liquid addition is 100g, and the copper-bath addition of mass percent concentration 20% is 5g, and drying temperature is 100 DEG C, stirring
6h is stood after 6h, calcination temperature is changed to 600 DEG C, and other conditions are constant, obtains solid phosphoric acid catalyst.
In foregoing adipic acid liquid phase method technique, solid phosphoric acid input amount accounts for the 1.0% of the total input amount of reactant, stirring
Rotating speed is 1000r/min, other process conditions are identical with example 1.It was found that after reaction 60min, dehydration rate reaches 69.8%.
【Embodiment 3】
Phosphoric acid concentration in the preparation process of 1 solid phosphoric acid of embodiment is changed to mass percent concentration 65%, phosphoric acid is molten
The addition of liquid is 150g, and the addition of aluminum sulfate solution is 7.5g, and calcination temperature is changed to 400 DEG C, and drying temperature is 140 DEG C,
Other conditions are constant, obtain solid phosphoric acid catalyst.
In foregoing adipic acid liquid phase method technique, the input amount of adipic acid is 200g, and the input amount of adiponitrile is 400g,
Solid phosphoric acid input amount accounts for the 2.1% of the total input amount of reactant, ammonia flow 400L/h, speed of agitator 2000r/min, instead
It is 280 DEG C to answer temperature.It was found that after reaction 60min, dehydration rate reaches 91.6%.
【Embodiment 4】
Phosphoric acid concentration in the preparation process of 1 solid phosphoric acid of embodiment is changed to mass percent concentration 85%, phosphoric acid is molten
The addition of liquid is 150g, and the addition of aluminum sulfate solution is 7.5g, and 500 DEG C of calcination temperature, other conditions are constant, obtains solid
Phosphoric acid catalyst.
In foregoing adipic acid liquid phase method technique, the input amount of adipic acid is 200g, and the input amount of adiponitrile is 400g,
Solid phosphoric acid input amount accounts for the 2.5% of the total input amount of reactant, ammonia flow 400L/h, speed of agitator 1500r/min, instead
It is 280 DEG C to answer temperature.It was found that after reaction 60min, dehydration rate reaches 94.7%.
【Embodiment 5】
Phosphoric acid concentration in the preparation process of 1 solid phosphoric acid of embodiment is changed to mass percent concentration 55%, phosphoric acid is molten
Liquid addition is 100g, copper sulphate and the ferric sulfate (mass ratio 1 of mass percent concentration 20%:1) solution addition is 5g,
Calcination temperature is changed to 500 DEG C, and other conditions are constant, obtains solid phosphoric acid catalyst.
In foregoing adipic acid liquid phase method technique, the input amount of adipic acid is 100g, and the input amount of adiponitrile is 200g,
Solid phosphoric acid input amount accounts for the 1.7% of the total input amount of reactant, ammonia flow 200L/h, speed of agitator 1500r/min, instead
It is 260 DEG C to answer temperature.It was found that after reaction 60min, dehydration rate reaches 56.6%.
【Comparative example 1】
Any catalyst is added without, other process conditions and embodiment 1 are identical, and after reacting 60min, dehydration rate is
26.7%.
【Comparative example 2】
It is industrial to use according to Zhang Yingnian, the report of peak et al. " researchs of Adiponitrile reaction macrokinetics "
Liquid phosphoric acid catalyst concn at 0.2%, reaction effect is optimal.In process conditions reaction system same as Example 3
In, solid phosphoric acid catalyst is replaced with suitable liquid phosphoric acid catalyst, phosphoric acid concentration is controlled after 0.2%, reaction 60min,
Dehydration rate is 85.3%.
【Comparative example 3】
Reaction condition is same as Example 3, but is not added with aluminum sulfate, and after reacting 60min, dehydration rate reaches 89.3%.
Claims (9)
1. the method for a kind of adipic acid liquid phase method production adiponitrile, it is characterised in that catalyst is solid phosphoric acid catalyst, to anti-
Answer and adipic acid and diluent are put into kettle, when reaction heats and stirs raw material, ammonia is passed through after reaching certain temperature, by one section
Product is generated after time response；
The diluent is the one or more in adiponitrile, glutaronitrile and pimelic dinitrile.
2. the method for adipic acid liquid phase method production adiponitrile according to claim 1, it is characterised in that the solid phosphoric acid
Method for preparing catalyst is：By a certain amount of diatomite under 100-140 DEG C of baking oven after dry 1-2h, by dry diatomite
It is impregnated in the phosphoric acid solution of excessive 55%-95% and the aluminum sulfate solution mixed solution of 15-25wt%, stirs 6-12h, so
After stand 6-12h；Mixed solution is centrifuged after standing, when obtained sediment dry 6-12 in 100-140 DEG C of baking oven is small；It is dry
Sediment is placed in pipe type calciner after dry, N2In 300 DEG C of -700 DEG C of roasting 1-2h under protective condition；Pressed after cooling
Sheetmolding, obtains the particle of 10-50 mesh after sieve screens, and forms solid phosphoric acid catalyst.
3. the method for adipic acid liquid phase method production adiponitrile according to claim 2, it is characterised in that the phosphoric acid solution
It is 10-15 with diatomaceous mass ratio, the addition of aluminum sulfate is the 10%-15% of diatomite quality.
4. the method for adipic acid liquid phase method according to claim 1 or 2 production adiponitrile, it is characterised in that it is described oneself two
The mass ratio of acid and diluent is 1:2.
5. the method for adipic acid liquid phase method production adiponitrile according to claim 1 or 2, it is characterised in that solid phosphoric acid
Dosage is adipic acid and the 1%-2.5% of diluent gross mass.
6. the method for adipic acid liquid phase method production adiponitrile according to claim 1 or 2, it is characterised in that stirred during reaction
Mix rotating speed is 1000-2000r/min.
7. the method for adipic acid liquid phase method production adiponitrile according to claim 1 or 2, it is characterised in that add during reaction
Hot temperature is 260 DEG C -280 DEG C.
8. the method for adipic acid liquid phase method production adiponitrile according to claim 1 or 2, it is characterised in that lead to during reaction
The ammonia flow entered is 150L/h-400L/h.
9. the method for adipic acid liquid phase method production adiponitrile according to claim 1 or 2, it is characterised in that reaction time
For 0.5-2h.
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| CN108821997B (en) * | 2018-06-01 | 2021-03-16 | 重庆华峰聚酰胺有限公司 | Preparation method of adiponitrile and product thereof |
| CN108409606B (en) * | 2018-06-01 | 2019-03-29 | 重庆华峰化工有限公司 | A kind of production system of adiponitrile |
| CN109678756B (en) * | 2018-12-25 | 2021-09-17 | 上海交通大学 | Reaction device and method for producing adiponitrile |
| CN111054436B (en) * | 2019-12-16 | 2021-04-23 | 中国科学院大连化学物理研究所 | Application of plasma modified phosphotungstic heteropoly acid in synthesis of adiponitrile from adipic acid |
| CN111056972B (en) * | 2019-12-16 | 2021-06-08 | 中国科学院大连化学物理研究所 | Application of alkyl quaternary phosphonium salt ionic liquid in synthesis of adiponitrile from adipic acid |
| CN113264848A (en) * | 2020-01-29 | 2021-08-17 | 英威达纺织（英国）有限公司 | Production of adiponitrile |
| CN115433104B (en) * | 2022-08-22 | 2024-02-06 | 沈阳开拓利思科技有限公司 | Preparation method of sebaconitrile |
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| US5202455A (en) * | 1990-12-17 | 1993-04-13 | Huels Aktiengesellschaft | Process for the liquid-phase preparation of nitriles from aliphatic dicarboxylic acids |
| CN102239139A (en) * | 2008-12-04 | 2011-11-09 | 罗地亚经营管理公司 | Method for manufacturing compounds including nitrile functions |
| CN103896805A (en) * | 2012-12-27 | 2014-07-02 | 鞍山市国锐化工有限公司 | Method and equipment for production of adiponitrile from adipic acid |
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| US5202455A (en) * | 1990-12-17 | 1993-04-13 | Huels Aktiengesellschaft | Process for the liquid-phase preparation of nitriles from aliphatic dicarboxylic acids |
| CN102239139A (en) * | 2008-12-04 | 2011-11-09 | 罗地亚经营管理公司 | Method for manufacturing compounds including nitrile functions |
| CN103896805A (en) * | 2012-12-27 | 2014-07-02 | 鞍山市国锐化工有限公司 | Method and equipment for production of adiponitrile from adipic acid |
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