CN109438256A - A kind of production method and production system of hexamethylene diamine - Google Patents
A kind of production method and production system of hexamethylene diamine Download PDFInfo
- Publication number
- CN109438256A CN109438256A CN201811345575.1A CN201811345575A CN109438256A CN 109438256 A CN109438256 A CN 109438256A CN 201811345575 A CN201811345575 A CN 201811345575A CN 109438256 A CN109438256 A CN 109438256A
- Authority
- CN
- China
- Prior art keywords
- sent
- tower
- reactor
- removing column
- lightness
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 261
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 77
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- 235000019441 ethanol Nutrition 0.000 claims abstract description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000007789 gas Substances 0.000 claims abstract description 31
- 238000004064 recycling Methods 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000007864 aqueous solution Substances 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 230000018044 dehydration Effects 0.000 claims abstract description 5
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims description 26
- 230000005494 condensation Effects 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 20
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 12
- 239000000470 constituent Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000002351 wastewater Substances 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000011265 semifinished product Substances 0.000 claims description 3
- 239000002918 waste heat Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 2
- 230000006835 compression Effects 0.000 claims 2
- 238000007906 compression Methods 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 18
- 238000007086 side reaction Methods 0.000 abstract description 3
- 108091006146 Channels Proteins 0.000 description 15
- 102000010637 Aquaporins Human genes 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GODRGSBJTFNCPC-UHFFFAOYSA-N n'-ethylhexane-1,6-diamine Chemical compound CCNCCCCCCN GODRGSBJTFNCPC-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- 108010063290 Aquaporins Proteins 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
Abstract
The invention discloses the production method of hexamethylene diamine and production systems.The production method of hexamethylene diamine the following steps are included: raw material is mixed in premixer after be sent into reactor, hydrogen is passed through into reactor and is reacted;The water and ethyl alcohol of reactor head gas phase flow back into reactor after gas phase condenser condenses, and the hydrogen of reactor head gas phase, which is fed again into reactor after being compressed, participates in reaction;The material that reactor bottom contains catalyst is sent into catalyst recycling can and is handled;The material that reactor obtains is sent into dealcoholysis tower preheater after being filtered;Material enters dealcoholysis tower after dealcoholysis tower preheater, material is sent into phase separator through dealcoholysis tower preheater after dealcoholysis tower sloughs ethyl alcohol, in phase separator, material is separated with sodium hydrate aqueous solution, and the material isolated obtains finished product after dehydration and a series of de- weight, de- light processing.Method reaction yield of the invention improves, and side reaction is few, and system operation time is long.
Description
Technical field
The present invention relates to the production methods and production system of chemical technology field more particularly to a kind of hexamethylene diamine.
Background technique
Hexamethylene diamine is the important source material of chemical industry synthesis, mainly for the production of nylon66 fiber and 610 resins.The production work of hexamethylene diamine
Skill mainly has caprolactam method, butadiene process and adiponitrile catalytic hydrogenation method.Caprolactam method and butadiene process are only applicable to small
Large-scale production, and be gradually eliminated because production cost is higher, adiponitrile catalytic hydrogenation prepares hexamethylene diamine method because of simple process, production
Quality is high, production cost is low and is widely used.
The method that adiponitrile catalytic hydrogenation prepares hexamethylene diamine, is industrially divided into high-pressure process and low-pressure process.Wherein, low-pressure process
Using nickel-base catalyst, reaction temperature is about 70~100 DEG C, pressure about 1.8~2.7MPa, and the selectivity of hexamethylene diamine is up to 99%.
But in the production process of hexamethylene diamine, some side reactions also occur, Main By product has azepan, amino-capronitrile, 1,2-
Diaminocyclohexane, N- ethyl hexamethylene diamine, aminomethylcyclopentane etc., wherein azepan, 1,2- diaminocyclohexane, N-
Ethyl hexamethylene diamine etc. with hexamethylene diamine is more difficult separates, there are also superfluous ethyl alcohol, sodium hydroxide and nickel-base catalysts etc. in mixture
Component, the presence of above-mentioned substance will will affect the product quality of final products high-quality essence hexamethylene diamine and downstream user, as coloration,
The indexs such as purity.In addition the phenomenon that adipic dinitrile hydrogenation reactor recurrent canal leads to blocking because of catalyst unsmooth flowing frequent occurrence,
The daily operating reacted to adipic dinitrile hydrogenation brings very big pressure.The main reason for reactor plugs is catalyst grain size change
Small, viscosity is big, mobile performance is deteriorated, in decanter caused by catalyst wall built-up, accumulation.Once reactor blocks, processing is not
It will seriously affect the daily operating of adipic dinitrile hydrogenation reaction in time, the hexamethylene diamine that blocking causes adipic dinitrile hydrogenation reaction to generate is miscellaneous
Matter increases.
Summary of the invention
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide a kind of production method of hexamethylene diamine and lifes
Production system, reaction yield improve, and can effectively remove the impurity and solid particle in product, and maximumlly reduce the energy of system
Consumption.
According to an aspect of the present invention, a kind of production method of hexamethylene diamine is provided, comprising the following steps:
Premixer is added in a certain amount of adiponitrile, ethyl alcohol, water, catalyst, sodium hydroxide, is obtained uniformly mixed anti-
Answer mixture;
The reaction mixture is sent into reactor, and is passed through hydrogen into the reactor and is reacted, after reaction
Material is obtained in the reactor head, further includes the gaseous substance at top and the object that catalyst is contained in bottom in the reactor
Material;
The water and ethyl alcohol of the reactor head gas phase are flowed back into after gas phase condenser condenses in the reactor, are returned
At least part liquid flowed in the reactor flows to lower end, the reactor top from the upper end of the reactor interior conduit
The hydrogen of portion's gas phase enters hydrogen gas compressor by the gas phase condenser, is fed again into the reactor and participates in after being compressed
Reaction;
The material that the reactor bottom contains catalyst is sent into catalyst recycling can and is handled, the catalysis recycled
Agent is used as raw material to be sent into the premixer again, and the material recycled is imported into system again;
The material that the reactor obtains is filtered, and the catalyst being obtained by filtration is sent into the catalyst recycling can
It is inside handled, the material of filtered material and catalyst recycling can recycling is sent into dealcoholysis tower preheater after converging;
Material enters dealcoholysis tower after the dealcoholysis tower preheater, and material is after the dealcoholysis tower sloughs ethyl alcohol by institute
The material for stating dealcoholysis tower preheater and non-dealcoholysis carries out heat exchange, is then fed into phase separator, in the phase separator, material
It is layered with sodium hydrate aqueous solution, the sodium hydrate aqueous solution isolated is discharged from below, the material isolated is by dehydration
And finished product is obtained after a series of de- weight, de- light processing.
Further, be added the adiponitrile of the premixer, ethyl alcohol, water, catalyst, sodium hydroxide mass ratio be
(100~200): (100~200): (10~50): (0.5~15): 1, the premixer control temperature is at 10~40 DEG C.
Further, the material that the reactor obtains first is sent into material buffer tank, then before being sent into filter
The filter is sent by the material buffer tank again, is equipped with agitating device, the material buffer tank in the material buffer tank
Temperature control at 50~70 DEG C, pressure is normal pressure.
Further, material enters dealcoholysis tower after the dealcoholysis tower preheater, and the temperature control of the dealcoholysis tower exists
80~140 DEG C, ethyl alcohol is separated from the tower top of the dealcoholysis tower, and is sent into the premixing as raw material again after condensation
Device, the material after sloughing ethyl alcohol is sent into after the dealcoholysis tower preheater carries out heat exchange with the material of non-dealcoholysis mutually to be separated
Device.
Further, pans, object are sent into from the material that the phase separator is isolated from the top of the phase separator
When expecting to stand certain into after the pans, so that remaining sodium hydrate aqueous solution and feed separation, are isolated
Sodium hydrate aqueous solution is discharged from the bottom of the pans, and the material on the pans top is sent into dehydrating tower and is dehydrated.
Further, material is dehydrated in the dehydrating tower, and the dehydrating tower control temperature is vacuum at 40~150 DEG C
Operation, the waste water of overhead condensation are expelled directly out, and kettle material is sent into the first weight-removing column;Material passes through in first weight-removing column
Separation, tower top material are sent into the first lightness-removing column, and kettle material is sent into third weight-removing column, and the first weight-removing column control temperature exists
120~150 DEG C, be vacuumizing;Material is in first lightness-removing column by separation, the condensed low-boiling-point substance row of tower top material
Out, kettle material is sent into the second lightness-removing column, and the first lightness-removing column control temperature is vacuumizing at 85~130 DEG C;Material exists
By separation in second lightness-removing column, tower top material is sent into first lightness-removing column and is recycled, and kettle material is sent into finished product
Tower, the second lightness-removing column control temperature are vacuumizing at 80~170 DEG C;Material is in the finishing column by separation, tower
Second lightness-removing column to be sent into after the material condensation of top to recycle, and finished product is produced in the middle part of tower, kettle material is sent into the second weight-removing column,
The finishing column control temperature is vacuumizing at 90~170 DEG C;Material is in second weight-removing column by separation, tower top
It is sent into second lightness-removing column after material condensation to recycle, kettle material is sent into third weight-removing column, the second weight-removing column control
Temperature processed is vacuumizing at 80~170 DEG C;Material, by separation, is sent in the third weight-removing column after the condensation of tower top material
Enter first lightness-removing column or the pans recycle, the discharge of kettle material heavy constituent, the third weight-removing column control temperature
Degree is vacuumizing at 100~170 DEG C.
According to another aspect of the present invention, a kind of production system of hexamethylene diamine is provided, including premixer, reactor,
Gas phase condenser, hydrogen gas compressor, catalyst recycling can, material buffer tank, filter, dealcoholysis tower preheater, dealcoholysis tower, phase point
It is de- from device, pans, dehydrating tower, the first weight-removing column, the first lightness-removing column, the second lightness-removing column, finishing column, the second weight-removing column, third
Weight tower;
The premixer is for mixing adiponitrile, ethyl alcohol, water, catalyst and sodium hydroxide, and by mixed raw material
It is sent into the reactor;
It is suitable for being passed through hydrogen in the reactor, the raw material being sent into hydrogen and the premixer reacts, obtains
Semi-finished product hexamethylene diamine;
The gas phase condenser is used to condense the gaseous substance of the reactor head, and the liquid condensed is logical through flowing back
Road flows back to the reactor, and the return flow line allows at least part condensed fluid to enter the upper of the reactor interior conduit
Side, when condensate liquid flows downward above pipeline, suitable for rinsing the inner wall of the pipe of the reactor;
Compressed hydrogen is sent by the hydrogen gas compressor for compressing the hydrogen being discharged through the gas phase condenser
The reactor;
The catalyst recycling can is used to recycle catalyst and the filter mistake in the reactor bottom material
Filter obtained catalyst;
Material is sent into the filtering for temporarily storing the material that the reactor obtains by the material buffer tank
Device;
The filter is used for filter material, and filtered material is sent into the dealcoholysis tower preheater;
The dealcoholysis tower preheater utilizes the waste heat from the material after the dealcoholysis that the dealcoholysis tower is discharged, described de- to entering
The material of alcohol tower is preheated, and the material after preheating is sent into the dealcoholysis tower;
The dealcoholysis tower is used to slough the ethyl alcohol in material, and the material after sloughing ethyl alcohol is sent into the phase knockout tower;
The phase knockout tower is used to that the material generation after dealcoholysis to be made mutually to separate, and sodium hydrate aqueous solution is separated from material
Out, the material isolated is sent into the pans;
The pans for isolating remaining sodium hydrate aqueous solution from material, be sent into de- by the material isolated
Water tower;
The dehydrating tower is used to slough the moisture in material, and dewatered material is sent into first weight-removing column;
The tower top material of first weight-removing column is sent into first lightness-removing column, and kettle material is sent into the de- weight of the third
Tower;
The condensed low-boiling-point substance discharge of the tower top material of first lightness-removing column, it is de- light that kettle material is sent into described second
Tower;
The tower top material of second lightness-removing column is sent into first lightness-removing column and is recycled, kettle material be sent into it is described at
Product tower;
Second lightness-removing column is sent into after the tower top material condensation of the finishing column to recycle, and finished product is produced in the middle part of tower,
Kettle material is sent into second weight-removing column;
It is sent into the second lightness-removing column after the tower top material condensation of second weight-removing column to recycle, described in kettle material feeding
Third weight-removing column;
First lightness-removing column is sent into after the tower top material condensation of the third weight-removing column or the pans recycle,
The discharge of kettle material heavy constituent.
Compared with prior art, the beneficial effects of the present invention are:
(1) proportion of each raw material (adiponitrile, ethyl alcohol, water, sodium hydroxide) of present invention synthesis hexamethylene diamine is reasonable, on the one hand
It ensure that sodium hydroxide plays the effect that it inhibits by-product to generate, on the other hand reduce the dosage of sodium hydroxide, reduce
The risk of system slagging as caused by sodium hydroxide, by designing reasonable raw material proportioning, so that generating the reaction of hexamethylene diamine
Yield improves, and side reaction is few, and system operation time is long;
(2) in the system of present invention synthesis hexamethylene diamine, gas phase condenser is directly set at the top of reactor, is eliminated often
The hydrogen alcohol knockout tower of rule, simplifies process, while can use solution in the second alcohol and water continuous flushing reactor condensed out
The pipeline of blocking solves the problems, such as that reactor solution is blocked, further, since the present invention is new without increasing to the dredging of pipeline
Material, therefore the balance of system will not be destroyed;
(3) present invention rationally recycles the various raw materials that each step is isolated from material, on the one hand improves product
Purity, on the other hand reduce the waste of raw material.
Detailed description of the invention
Fig. 1 is that (hexamethylene diamine production system be a complete, company for the schematic diagram of hexamethylene diamine production system first part of the invention
Continuous system, here for the convenience of display, by the first part of hexamethylene diamine production system and second part be divided into two parts into
Row display);
Fig. 2 is the schematic diagram of hexamethylene diamine production system second part of the invention;
In figure: 101, premixer;1011, circulating water channel;102, reactor;103, gas phase condenser;104, hydrogen
Compressor;105, catalyst recycling can;106, material buffer tank;1061, surge tank circulating water channel;107, filter;108,
Dealcoholysis tower preheater;109, dealcoholysis tower;110, phase separator;111, pans;112, dehydrating tower;113, the first weight-removing column;
114, the first lightness-removing column;115, the second lightness-removing column;116, finishing column;117, the second weight-removing column;118, third weight-removing column;201, into
Expect channel;202, mixed material channel;203, hydrogen paths;204, return flow line;205, catalyst recovery approach;206, first
Catalyst channels;207, second material channel;208, first material channel;209, third material channel;210, the second catalyst
Channel.
Specific embodiment
In the following, being described further in conjunction with specific embodiment to the present invention, it should be noted that is do not collided
Under the premise of, new embodiment can be formed between various embodiments described below or between each technical characteristic in any combination.
In the description of the present invention, it should be noted that " transverse direction ", " vertical if any term " center " for the noun of locality
To ", " length ", " width ", " thickness ", "upper", "lower", "front", "rear", "left", "right", "vertical", "horizontal", "top",
The indicating positions such as "bottom", "inner", "outside", " clockwise ", " counterclockwise " and positional relationship are orientation based on the figure or position
Relationship is set, the narration present invention is merely for convenience of and simplifies description, rather than the device or element of indication or suggestion meaning are necessary
It constructs and operates with specific orientation, with particular orientation, should not be understood as limiting specific protection scope of the invention.
It should be noted that the term " first ", " second " etc. in the description and claims of this application are to be used for
Similar object is distinguished, without being used to describe a particular order or precedence order.It should be understood that the data used in this way are suitable
It can be interchanged in the case of, so as to embodiments herein described herein.In addition, term " includes " and " having " and they
Any deformation, it is intended that cover it is non-exclusive include, for example, containing the process, method of a series of steps or units, being
System, product or equipment those of are not necessarily limited to be clearly listed step or unit, but may include be not clearly listed or
For the intrinsic other step or units of these process, methods, product or equipment.
As shown in Figure 1, 2, the present invention provides a kind of production system of hexamethylene diamine comprising premixer 101, reactor
102, gas phase condenser 103, hydrogen gas compressor 104, catalyst recycling can 105, material buffer tank 106, filter 107, dealcoholysis
Tower preheater 108, dealcoholysis tower 109, phase separator 110, pans 111, dehydrating tower 112, the first weight-removing column 113, first are de- light
Tower 114, the second lightness-removing column 115, finishing column 116, the second weight-removing column 117, third weight-removing column 118.
Premixer 101 is for mixing each reaction raw materials, to obtain reaction mixture.The reaction of premixer 101 is added
Raw material includes adiponitrile, ethyl alcohol, water, catalyst and sodium hydroxide.In some preferred embodiments, premixer 101 is added
Adiponitrile, ethyl alcohol, water, catalyst, sodium hydroxide mass ratio be (100~200): (100~200): (10~50): (0.5~
15): 1.
Further, multiple feeding-passages 201 are equipped at the top of premixer 101, each reaction raw materials pass through each feeding-passage
201 enter in premixer 101.There is agitating device, agitating device will be each anti-in premixer 101 in premixer 101
Raw material is answered to be uniformly mixed.The outside of premixer 101 have circulating water channel 1011, circulating water channel 1011 have water inlet with
And water return outlet, the material in premixer 101 is preheated or kept the temperature using the liquid recycled in circulating water channel 1011.
The temperature of premixer 101 is controlled at 10~40 DEG C.
Reactor 102 is for carrying out hydrogenation reaction.Mixed material channel is equipped between reactor 102 and premixer 101
202, the uniformly mixed reaction mixture of premixer 101 enters reactor 102 by mixed material channel 202.Reactor 102
Bottom be also connected to hydrogen paths 203, for participate in reaction hydrogen by hydrogen paths 203 enter reactor 102 in.Into
The hydrogen and reaction mixture for entering reactor 102 react, and obtain semi-finished product hexamethylene diamine.Preferably, in the temperature of reactor 102
Degree remains 70~90 DEG C, and pressure is passed through hydrogen under conditions of remaining 1.9~2.5MPa.
One end of gas phase condenser 103 is connected to the top of reactor 102, between gas phase condenser 103 and reactor 102
It is additionally provided with return flow line 204, the gaseous component at 102 top of reactor enters gas phase condenser 103, and the liquid condensed passes through
Return flow line 204 flows back into reactor 102.The gaseous component at the top of reactor 102 includes hydrogen, second alcohol and water, wherein second
Alcohol and water flows back into reactor 102 after the condensation of gas phase condenser 103, and hydrogen is discharged from the top of gas phase condenser 103
Into hydrogen gas compressor 104.103 top exit temperature of gas phase condenser is maintained at 25~55 DEG C.
Further, return flow line 204 allows at least part condensed fluid to enter the upper of 102 internal pipeline of reactor
Side, when condensate liquid flows downward above pipeline, can rinse the inner wall of the pipe in reactor 102, so as to prevent from being catalyzed
Agent particle blocks pipeline.
Hydrogen gas compressor 104 is used to compress the hydrogen being discharged from gas phase condenser 103, and compressed hydrogen is passed through
Hydrogen paths 203, which are sent in reactor 102, continues to participate in reaction.
Catalyst recycling can 105 is used to recycle the catalyst granules in reactor 102.Catalyst recycling can 105 with react
Catalyst recovery approach 205 is connected between the bottom of device 102, the material that catalyst granules is contained in 102 bottom of reactor passes through
Catalyst recovery approach 205 is sent into catalyst recycling can 105.Catalyst recycling can 105 is by the material containing catalyst granules
It is separated into catalyst, material and waste material, is urged wherein isolated catalyst imports conveying by the first catalyst channels 206
The feeding-passage 201 of agent, isolated material are sent into dealcoholysis tower preheater 108 by second material channel 207, are isolated
Waste material be discharged catalyst recycling can 105.
The top material of reactor 102 is sent into material buffer tank 106 by first material channel 208.Material buffer tank 106
It is interior to be equipped with agitating device, for stirring the material in material surge tank 106.The outside of material buffer tank 106 is followed with surge tank
Ring aquaporin 1061, surge tank circulating water channel 1061 have water inlet and water return outlet, utilize surge tank circulating water channel
The liquid recycled in 1061 is heated or is kept the temperature to the material in material buffer tank 106.The temperature of material buffer tank 106 controls
At 50~70 DEG C, pressure is normal pressure.
The interior material of material buffer tank 106 is sent into filter 107 by third material channel 209 and is filtered.Filter
107 separate the catalyst in material, and the material after removing catalyst is sent into dealcoholysis tower preheater 108, and that isolates urges
Agent is sent into catalyst recycling can 105.
The material and the material in second material channel 207 that catalyst is removed in filter 107 are sent into dealcoholysis tower after converging
Preheater 108.The second catalyst channels 210 are equipped between the bottom and catalyst recycling can 105 of filter 107.
After into the material and the material-heat-exchanging from 109 tower reactor of dealcoholysis tower of dealcoholysis tower preheater 108, it is sent into dealcoholysis tower
In 109.Dealcoholysis tower preheater 108 can use the waste heat of 109 kettle material of dealcoholysis tower to the material before entering dealcoholysis tower 109
It is preheated, energy consumption can be effectively reduced.
After material enters dealcoholysis tower 109, ethyl alcohol is isolated at the top of dealcoholysis tower 109, and the ethyl alcohol isolated is from overhead condensation
The feeding-passage 201 for conveying ethyl alcohol is imported after recycling, forms recycling for ethyl alcohol.The temperature control of dealcoholysis tower 109 exists
80~140 DEG C, pressure is normal pressure.
Material after sloughing ethyl alcohol enters phase separator 110 after the heat exchange of dealcoholysis tower preheater 108.Phase separator 110
The separation of material and sodium hydrate aqueous solution, light component after separation are realized using the density contrast of material and sodium hydrate aqueous solution
Material is sent into pans 111 at the top of phase separator 110, and the sodium hydrate aqueous solution of 110 bottom of phase separator is arranged as waste liquid
Out.
There is also a small amount of sodium hydroxides for the material of feeding pans 111, after the standing of pans 111, sodium hydroxide water
Solution further with material layering, sodium hydrate aqueous solution is discharged from the bottom of pans 111, the material on top is sent into dehydration
Tower 112.
Material is dehydrated in dehydrating tower 112, and the waste water that overhead condensation obtains is expelled directly out, and kettle material is sent into the first de- weight
Tower 113.Dehydrating tower 112 controls temperature at 40~150 DEG C, is vacuumizing.
Material isolates heavy constituent in the first weight-removing column 113, and tower top material is sent into the first lightness-removing column 114, tower reactor object
Material is sent into third weight-removing column 118, and it is vacuumizing that the first weight-removing column 113, which controls temperature at 120~150 DEG C,.
Material isolates light component in the first lightness-removing column 114, the condensed low-boiling-point substance discharge of tower top material, tower reactor object
Material is sent into the second lightness-removing column 115, and it is vacuumizing that the first lightness-removing column 114, which controls temperature at 85~130 DEG C,.
Material isolates light component in the second lightness-removing column 115, and tower top material is sent into the first lightness-removing column 114 and recycles benefit
With kettle material is sent into finishing column 116, and it is vacuumizing that the second lightness-removing column 115, which controls temperature at 80~170 DEG C,.
Material separates again in finishing column 116, and the recycling of the second lightness-removing column 115, tower are sent into after the condensation of tower top material
Middle part produces finished product, and kettle material is sent into the second weight-removing column 117, and finishing column 116 controls temperature at 90~170 DEG C, grasps for vacuum
Make.
Material isolates heavy constituent in the second weight-removing column 117, is sent into the second lightness-removing column 115 after the condensation of tower top material and returns
It receives and utilizes, kettle material is sent into third weight-removing column 118, and it is vacuumizing that the second weight-removing column 117, which controls temperature at 80~170 DEG C,.
Material isolates heavy constituent in third weight-removing column 118, tower top material condensation after be sent into the first lightness-removing column 114 or
Pans 111 recycle, and kettle material heavy constituent discharge, third weight-removing column 118 controls temperature at 100~170 DEG C, are vacuum
Operation.
The present invention also provides a kind of production methods of hexamethylene diamine, comprising the following steps:
Premixer 101 is added in a certain amount of adiponitrile, ethyl alcohol, water, catalyst, sodium hydroxide, is uniformly mixed
Reaction mixture;
Above-mentioned reaction mixture is sent into reactor 102, and is passed through hydrogen into reactor 102 and is reacted, is reacted
Material is obtained at the top of reactor 102 afterwards, further includes the gaseous substance at top and the object that catalyst is contained in bottom in reactor 102
Material;
The water and ethyl alcohol of 102 top gas phase of reactor flow back into reactor 102 after the condensation of gas phase condenser 103,
At least part liquid flowed back into reactor 102 flows to lower end from the upper end of 102 interior conduit of reactor, and reactor 102 pushes up
The hydrogen of portion's gas phase enters hydrogen gas compressor 104 by gas phase condenser 103, is fed again into reactor 102 and joins after being compressed
With react;
The material that catalyst is contained in 102 bottom of reactor is sent into catalyst recycling can 105 and is handled, and that recycles urges
Agent is used as raw material to be sent into premixer 101 again, and the material recycled is imported into system again;
The material that reactor 102 obtains is filtered through filter 107, and the catalyst being obtained by filtration is sent into catalyst recycling can
It is handled in 105, the material that filtered material and catalyst recycling can 105 recycle is sent into dealcoholysis tower preheater after converging
108;
Material enters dealcoholysis tower 109 after dealcoholysis tower preheater 108, after that sends out from dealcoholysis tower 109 sloughs ethyl alcohol
Material is sent into phase separator 110 after dealcoholysis tower preheater 108 and the material of non-dealcoholysis carry out heat exchange, in phase separator
In 110, material and sodium hydrate aqueous solution are layered, and the sodium hydrate aqueous solution isolated are discharged from below, the object isolated
Material obtains finished product after dehydration and a series of de- weight, de- light processing.
Further, be added the adiponitrile of premixer 101, ethyl alcohol, water, catalyst, sodium hydroxide mass ratio be
(100~200): (100~200): (10~50): (0.5~15): 1, premixer 101 controls temperature at 10~40 DEG C.
Further, the material that reactor 102 obtains first is sent into material buffer tank before being sent into filter 107
106, filter 107 is then sent by material buffer tank 106 again, is equipped with agitating device, material buffer tank in material buffer tank 106
106 temperature is controlled at 50~70 DEG C, and pressure is normal pressure.
Further, material enters dealcoholysis tower 109 after dealcoholysis tower preheater 108, and the temperature control of dealcoholysis tower 109 exists
80~140 DEG C, ethyl alcohol is separated from the tower top of dealcoholysis tower 109, and is sent into premixer as raw material again after condensation
101, the material after sloughing ethyl alcohol is sent into phase separator after dealcoholysis tower preheater 108 and the material of non-dealcoholysis carry out heat exchange
110。
Further, pans 111, object are sent into from the material that phase separator 110 is isolated from the top of phase separator 110
When expecting to stand certain into after pans 111, so that remaining sodium hydrate aqueous solution and feed separation, the hydrogen isolated
Aqueous solution of sodium oxide is discharged from the bottom of pans 111, and the material on 111 top of pans is sent into dehydrating tower 112 and is dehydrated.
Further, material is dehydrated in dehydrating tower 112, and dehydrating tower 112 controls temperature at 40~150 DEG C, is grasped for vacuum
Make, the waste water of overhead condensation is expelled directly out, and kettle material is sent into the first weight-removing column 113;Material passes through in the first weight-removing column 113
Separation, tower top material are sent into the first lightness-removing column 114, and kettle material is sent into third weight-removing column 118, and the first weight-removing column 113 controls temperature
Degree is vacuumizing at 120~150 DEG C;Material is in the first lightness-removing column 114 by separation, the condensed low boiling of tower top material
Object discharge, kettle material are sent into the second lightness-removing column 115, and it is vacuumizing that the first lightness-removing column 114, which controls temperature at 85~130 DEG C,;
Material is by separation in the second lightness-removing column 115, and tower top material is sent into the first lightness-removing column 114 and is recycled, and kettle material is sent into
Finishing column 116, the second lightness-removing column 115 control temperature at 80~170 DEG C, are vacuumizing;Material is in finishing column 116 through excessive
From tower top material is sent into the recycling of the second lightness-removing column 115 after condensing, finished product is produced in the middle part of tower, and kettle material is sent into second and is taken off
Weight tower 117, finishing column 116 control temperature at 90~170 DEG C, are vacuumizing;Material is in the second weight-removing column 117 through excessive
From, the second lightness-removing column 115, which is sent into, after the condensation of tower top material recycles, kettle material feeding third weight-removing column 118, the second de- weight
Tower 117 controls temperature at 80~170 DEG C, is vacuumizing;For material by separation in third weight-removing column 118, tower top material is cold
It is sent into the first lightness-removing column 114 after solidifying or pans 111 recycle, kettle material heavy constituent discharge, third weight-removing column 118 controls
Temperature is vacuumizing at 100~170 DEG C.
In a specific embodiment, using Fig. 1 of the present invention, production system shown in Fig. 2, premixer 101 is added
Adiponitrile, ethyl alcohol, water, catalyst, sodium hydroxide mass ratio be 180:140:25:4:1, the reaction temperature in reactor 102
It is 70~90 DEG C, pressure is 1.9~2.5MPa, and the yield of hexamethylene diamine is up to 99.5%.
The above embodiment is only the preferred embodiment of the present invention, and the scope of protection of the present invention is not limited thereto,
The variation and replacement for any unsubstantiality that those skilled in the art is done on the basis of the present invention belong to institute of the present invention
Claimed range.
Claims (7)
1. a kind of production method of hexamethylene diamine, which comprises the following steps:
Premixer is added in a certain amount of adiponitrile, ethyl alcohol, water, catalyst, sodium hydroxide, it is mixed to obtain uniformly mixed reaction
Close object;
The reaction mixture is sent into reactor, and is passed through hydrogen into the reactor and is reacted, in institute after reaction
It states reactor head and obtains material, further include the gaseous substance at top and the material that catalyst is contained in bottom in the reactor;
The water and ethyl alcohol of the reactor head gas phase are flowed back into after gas phase condenser condenses in the reactor, are flowed back into
At least part liquid in the reactor flows to lower end, the reactor head gas from the upper end of the reactor interior conduit
The hydrogen of phase enters hydrogen gas compressor by the gas phase condenser, is fed again into the reactor and is participated in instead after being compressed
It answers;
The material that the reactor bottom contains catalyst is sent into catalyst recycling can and is handled, and the catalyst recycled is again
Secondary that raw material is used as to be sent into the premixer, the material recycled is imported into system again;
The material that the reactor obtains is filtered, the catalyst that is obtained by filtration be sent into the catalyst recycling can into
The material of row processing, filtered material and catalyst recycling can recycling is sent into dealcoholysis tower preheater after converging;
Material enters dealcoholysis tower after the dealcoholysis tower preheater, and material is after the dealcoholysis tower sloughs ethyl alcohol by described de-
Alcohol tower preheater and the material of non-dealcoholysis carry out heat exchange, are then fed into phase separator, in the phase separator, material and hydrogen
Aqueous solution of sodium oxide layering, the sodium hydrate aqueous solution isolated is discharged from below, the material isolated by dehydration and
Finished product is obtained after a series of de- weight, de- light processing.
2. the production method of hexamethylene diamine according to claim 1, which is characterized in that be added the premixer oneself two
Nitrile, ethyl alcohol, water, catalyst, sodium hydroxide mass ratio be (100~200): (100~200): (10~50): (0.5~15):
1, the premixer control temperature is at 10~40 DEG C.
3. the production method of hexamethylene diamine according to claim 1, which is characterized in that the material that the reactor obtains is being sent
It before entering filter, is first sent into material buffer tank, the filter, the material is then sent by the material buffer tank again
Agitating device is equipped in surge tank, the temperature of the material buffer tank is controlled at 50~70 DEG C, and pressure is normal pressure.
4. the production method of hexamethylene diamine according to claim 1, which is characterized in that material passes through the dealcoholysis tower preheater
Entering dealcoholysis tower afterwards, at 80~140 DEG C, ethyl alcohol is separated from the tower top of the dealcoholysis tower for the temperature control of the dealcoholysis tower, and
Be sent into the premixer as raw material again after condensation, the material after sloughing ethyl alcohol by the dealcoholysis tower preheater with
The material of non-dealcoholysis is sent into phase separator after carrying out heat exchange.
5. the production method of hexamethylene diamine according to claim 1, which is characterized in that the object isolated from the phase separator
Material is sent into pans from the top of the phase separator, and material enters after the pans when stand certain, so that remaining
Sodium hydrate aqueous solution and feed separation, the sodium hydrate aqueous solution isolated from the bottom of the pans be discharged, it is described
The material on pans top is sent into dehydrating tower and is dehydrated.
6. the production method of hexamethylene diamine according to claim 5, which is characterized in that material is dehydrated in the dehydrating tower,
The dehydrating tower control temperature is vacuumizing at 40~150 DEG C, and the waste water of overhead condensation is expelled directly out, and kettle material is sent into
First weight-removing column;For material by separation in first weight-removing column, tower top material is sent into the first lightness-removing column, and kettle material is sent into
Third weight-removing column, the first weight-removing column control temperature are vacuumizing at 120~150 DEG C;Material is in first lightness-removing column
Middle by separation, the condensed low-boiling-point substance of tower top material is discharged, kettle material the second lightness-removing column of feeding, the first lightness-removing column control
Temperature processed is vacuumizing at 85~130 DEG C;Material passes through in second lightness-removing column to be separated, described in tower top material feeding
First lightness-removing column recycles, and kettle material is sent into finishing column, and the second lightness-removing column control temperature is true at 80~170 DEG C
Do-nothing operation;Material, by separation, is sent into second lightness-removing column after the condensation of tower top material and is recycled in the finishing column, tower
Middle part produces finished product, and kettle material is sent into the second weight-removing column, and the finishing column control temperature is vacuumizing at 90~170 DEG C;
Material, by separation, is sent into second lightness-removing column after the condensation of tower top material and is recycled in second weight-removing column, tower reactor
Material is sent into third weight-removing column, and the second weight-removing column control temperature is vacuumizing at 80~170 DEG C;Material is described
By separation in three weight-removing columns, it is sent into first lightness-removing column after the condensation of tower top material or the pans recycle, tower reactor
The discharge of material heavy constituent, the third weight-removing column control temperature are vacuumizing at 100~170 DEG C.
7. a kind of production system of hexamethylene diamine, which is characterized in that including premixer, reactor, gas phase condenser, hydrogen compression
Machine, catalyst recycling can, material buffer tank, filter, dealcoholysis tower preheater, dealcoholysis tower, phase separator, pans, dehydrating tower,
First weight-removing column, the first lightness-removing column, the second lightness-removing column, finishing column, the second weight-removing column, third weight-removing column;
Mixed raw material is sent by the premixer for mixing adiponitrile, ethyl alcohol, water, catalyst and sodium hydroxide
The reactor;It is suitable for being passed through hydrogen in the reactor, the raw material being sent into hydrogen and the premixer reacts, obtains
To semi-finished product hexamethylene diamine;The gas phase condenser is used to condense the gaseous substance of the reactor head, the liquid condensed
The reactor is flowed back to through return flow line, the return flow line allows at least part condensed fluid to enter the reactor inner tube
The top in road, when condensate liquid flows downward above pipeline, suitable for rinsing the inner wall of the pipe of the reactor;The hydrogen compression
Machine is sent into the reactor for compressing the hydrogen being discharged through the gas phase condenser, and by compressed hydrogen;The catalysis
Agent recycling can is used to recycle the catalyst that catalyst and the filter in the reactor bottom material are obtained by filtration;Institute
Material buffer tank is stated for temporarily storing the material that the reactor obtains, and material is sent into the filter;The filtering
Device is used for filter material, and filtered material is sent into the dealcoholysis tower preheater;The dealcoholysis tower preheater is utilized from institute
The waste heat of material after stating the dealcoholysis of dealcoholysis tower discharge preheats the material for entering the dealcoholysis tower, the material after preheating
It is sent into the dealcoholysis tower;The dealcoholysis tower is used to slough the ethyl alcohol in material, and the material after sloughing ethyl alcohol is sent into the phase separation
Tower;The phase knockout tower is used to that the material generation after dealcoholysis to be made mutually to separate, and sodium hydrate aqueous solution is isolated from material, point
The material separated out is sent into the pans;The pans are used to isolate remaining sodium hydrate aqueous solution from material,
The material isolated is sent into dehydrating tower;The dehydrating tower is used to slough moisture in material, and dewatered material is sent into described the
One weight-removing column;The tower top material of first weight-removing column is sent into first lightness-removing column, and kettle material is sent into the de- weight of the third
Tower;The condensed low-boiling-point substance discharge of the tower top material of first lightness-removing column, kettle material are sent into second lightness-removing column;It is described
The tower top material of second lightness-removing column is sent into first lightness-removing column and is recycled, and kettle material is sent into the finishing column;It is described at
Second lightness-removing column is sent into after the tower top material condensation of product tower to recycle, finished product is produced in the middle part of tower, and kettle material is sent into institute
State the second weight-removing column;It is sent into the recycling of the second lightness-removing column after the tower top material condensation of second weight-removing column, kettle material is sent
Enter the third weight-removing column;First lightness-removing column or the pans are sent into after the tower top material condensation of the third weight-removing column
It recycles, the discharge of kettle material heavy constituent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811345575.1A CN109438256A (en) | 2018-11-13 | 2018-11-13 | A kind of production method and production system of hexamethylene diamine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811345575.1A CN109438256A (en) | 2018-11-13 | 2018-11-13 | A kind of production method and production system of hexamethylene diamine |
Publications (1)
Publication Number | Publication Date |
---|---|
CN109438256A true CN109438256A (en) | 2019-03-08 |
Family
ID=65552089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811345575.1A Pending CN109438256A (en) | 2018-11-13 | 2018-11-13 | A kind of production method and production system of hexamethylene diamine |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109438256A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110237570A (en) * | 2019-07-18 | 2019-09-17 | 重庆华峰化工有限公司 | A kind of hexamethylene diamine lye separation system |
CN111233703A (en) * | 2020-02-24 | 2020-06-05 | 山东金石新材料有限公司 | Primary diamine production equipment and method for producing primary diamine by adopting same |
CN112321438A (en) * | 2020-11-25 | 2021-02-05 | 重庆华峰化工有限公司 | Synthesis method of hexamethylene diamine |
CN112812020A (en) * | 2021-02-08 | 2021-05-18 | 陈天然 | Method and device for producing hexamethylene diamine from caprolactam |
CN113105340A (en) * | 2021-04-15 | 2021-07-13 | 重庆华峰化工有限公司 | Production system and method of 2-hexanetriamine |
CN113248389A (en) * | 2021-05-20 | 2021-08-13 | 重庆华峰化工有限公司 | Production system and method of 1, 2-cyclohexanediamine |
CN114249655A (en) * | 2021-12-24 | 2022-03-29 | 无锡殷达尼龙有限公司 | Method for separating alkali from hydrogenation product of decanedinitrile |
CN114618394A (en) * | 2022-03-17 | 2022-06-14 | 北京道思克矿山装备技术有限公司 | Hexamethylene diamine synthesis system |
CN115368224A (en) * | 2022-08-10 | 2022-11-22 | 北京化工大学 | System device and method for preparing hexamethylene diamine from butadiene |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3487621A (en) * | 1966-05-25 | 1970-01-06 | Rhone Poulenc Sa | Gas-liquid contact apparatus |
CN101516825A (en) * | 2006-09-19 | 2009-08-26 | 罗地亚管理公司 | Method for producing amines by the hydrogenation of nitrile compounds |
CN101855197A (en) * | 2007-10-04 | 2010-10-06 | 罗地亚管理公司 | Method for producing amines by nitrile compound hydrogenation |
CN204151265U (en) * | 2014-08-25 | 2015-02-11 | 中国石油天然气集团公司 | Hexanediamine production system |
CN106334469A (en) * | 2016-11-02 | 2017-01-18 | 中国天辰工程有限公司 | Static-state pipeline three-phase mixer and application thereof |
CN107537407A (en) * | 2017-09-28 | 2018-01-05 | 河南神马尼龙化工有限责任公司 | The method that adipic dinitrile hydrogenation reaction system and the system treatment reactor severe block |
CN207512105U (en) * | 2017-11-02 | 2018-06-19 | 河南神马尼龙化工有限责任公司 | A kind of hexamethylene diamine distillation system |
WO2018121042A1 (en) * | 2016-12-27 | 2018-07-05 | 河南神马尼龙化工有限责任公司 | Production method for high-quality pure hexanediamine |
CN209555114U (en) * | 2018-11-13 | 2019-10-29 | 中国化学赛鼎宁波工程有限公司 | A kind of production system of hexamethylene diamine |
-
2018
- 2018-11-13 CN CN201811345575.1A patent/CN109438256A/en active Pending
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3487621A (en) * | 1966-05-25 | 1970-01-06 | Rhone Poulenc Sa | Gas-liquid contact apparatus |
CN101516825A (en) * | 2006-09-19 | 2009-08-26 | 罗地亚管理公司 | Method for producing amines by the hydrogenation of nitrile compounds |
CN101855197A (en) * | 2007-10-04 | 2010-10-06 | 罗地亚管理公司 | Method for producing amines by nitrile compound hydrogenation |
CN204151265U (en) * | 2014-08-25 | 2015-02-11 | 中国石油天然气集团公司 | Hexanediamine production system |
CN106334469A (en) * | 2016-11-02 | 2017-01-18 | 中国天辰工程有限公司 | Static-state pipeline three-phase mixer and application thereof |
WO2018121042A1 (en) * | 2016-12-27 | 2018-07-05 | 河南神马尼龙化工有限责任公司 | Production method for high-quality pure hexanediamine |
CN107537407A (en) * | 2017-09-28 | 2018-01-05 | 河南神马尼龙化工有限责任公司 | The method that adipic dinitrile hydrogenation reaction system and the system treatment reactor severe block |
CN207512105U (en) * | 2017-11-02 | 2018-06-19 | 河南神马尼龙化工有限责任公司 | A kind of hexamethylene diamine distillation system |
CN209555114U (en) * | 2018-11-13 | 2019-10-29 | 中国化学赛鼎宁波工程有限公司 | A kind of production system of hexamethylene diamine |
Non-Patent Citations (2)
Title |
---|
宋胜豪;: "降低催化剂单耗的措施", 内江科技, no. 01, 25 January 2009 (2009-01-25), pages 84 * |
魏文德: "《有机化工原料大全(第三卷)》", vol. 1, 31 August 1990, 化学工业出版社, pages: 59 - 62 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110237570A (en) * | 2019-07-18 | 2019-09-17 | 重庆华峰化工有限公司 | A kind of hexamethylene diamine lye separation system |
CN111233703A (en) * | 2020-02-24 | 2020-06-05 | 山东金石新材料有限公司 | Primary diamine production equipment and method for producing primary diamine by adopting same |
CN112321438A (en) * | 2020-11-25 | 2021-02-05 | 重庆华峰化工有限公司 | Synthesis method of hexamethylene diamine |
CN112321438B (en) * | 2020-11-25 | 2024-04-16 | 重庆华峰化工有限公司 | Synthesis method of hexamethylenediamine |
CN112812020A (en) * | 2021-02-08 | 2021-05-18 | 陈天然 | Method and device for producing hexamethylene diamine from caprolactam |
CN113105340A (en) * | 2021-04-15 | 2021-07-13 | 重庆华峰化工有限公司 | Production system and method of 2-hexanetriamine |
CN113248389A (en) * | 2021-05-20 | 2021-08-13 | 重庆华峰化工有限公司 | Production system and method of 1, 2-cyclohexanediamine |
CN114249655A (en) * | 2021-12-24 | 2022-03-29 | 无锡殷达尼龙有限公司 | Method for separating alkali from hydrogenation product of decanedinitrile |
CN114618394A (en) * | 2022-03-17 | 2022-06-14 | 北京道思克矿山装备技术有限公司 | Hexamethylene diamine synthesis system |
CN115368224A (en) * | 2022-08-10 | 2022-11-22 | 北京化工大学 | System device and method for preparing hexamethylene diamine from butadiene |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109438256A (en) | A kind of production method and production system of hexamethylene diamine | |
CN209555114U (en) | A kind of production system of hexamethylene diamine | |
CN107522602B (en) | Process and system for preparing DMM2 | |
CN104387236B (en) | A kind of propilolic alcohol, 1,4-butynediols and methenamine three coproduction continuous producing method | |
CN102241558A (en) | Reaction device and process for preparing cyclohexene by selectively hydrogenating benzene | |
CN114702375B (en) | Separation system and method for acetaldehyde product prepared from ethanol | |
CN107522601B (en) | Polyoxymethylene dimethyl ether separation device and process | |
CN110237570A (en) | A kind of hexamethylene diamine lye separation system | |
CN108774100A (en) | A kind of tert-butyl alcohol and methanol prepare the integrated processes of methyl tertiary butyl ether(MTBE) and isobutene | |
CN102796011A (en) | Preparation method for p-aminodiphenylamine | |
CN111056903B (en) | Process and device for recovering benzene partial hydrogenation catalyst | |
CN111892525A (en) | N-methyl pyrrolidone for liquid crystal panel and production process thereof | |
CN109721469A (en) | A kind of preparation method of cyclopentanone | |
CN104693166B (en) | A kind of preparation method of metaformaldehyde | |
CN203862234U (en) | Multifunctional reaction system | |
CN217568658U (en) | Entrained catalyst treatment system for cyclohexene hydration reaction | |
CN110028385A (en) | A kind of method and apparatus of separating isopropanol diisopropyl ether aqueous solution | |
CN208762430U (en) | The anti-corrosive apparatus of methyl acetate hydrolysis and acetic acid refining during polyvinyl alcohol disposing mother liquor | |
CN103502200B (en) | For the production of the technique of the improvement of hexamethylene-diamine | |
CN202047018U (en) | Device for preparing cyclohexene from benzene through selective hydrogenation | |
CN114874083A (en) | Olefin hydroformylation method and system | |
CN104968638A (en) | Method for removing acrolein from the process gas of a heterogeneously catalysed oxidation of propene | |
CN101443310A (en) | Process for continuously preparing n- ethyl-2-pyrrolidone (NEP) | |
CN112409181A (en) | Dimethyl oxalate rectifying device for coal chemical industry | |
CN100366602C (en) | Method for avoiding corrosion |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |