CN108610261A - A kind of synthetic method improving phenylenediamine yields - Google Patents
A kind of synthetic method improving phenylenediamine yields Download PDFInfo
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- CN108610261A CN108610261A CN201810393439.3A CN201810393439A CN108610261A CN 108610261 A CN108610261 A CN 108610261A CN 201810393439 A CN201810393439 A CN 201810393439A CN 108610261 A CN108610261 A CN 108610261A
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- phenylenediamine
- reaction kettle
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
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- 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
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- 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
- C07C209/86—Separation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D2009/0086—Processes or apparatus therefor
Abstract
The present invention relates to a kind of synthetic methods improving phenylenediamine yields, the synthetic method is using nitroaniline as raw material, vulcanized sodium is reducing agent, and reduction reaction occurs at high temperature, and phenylenediamine solution, hypo solution and sodium hydroxide solution are generated in the first reaction kettle；By the vacuum distillation under vacuum of the material in the first reaction kettle, hypo solution is distilled out under vacuum condition；Continue to carry out vacuum distillation to remaining material in the first reaction kettle, distills out phenylenediamine solution under vacuum；P-phenylenediamine solution carries out crystallization treatment in the second reaction kettle, and phenylenediamine crude product is made；Phenylenediamine crude product is subjected to rectifying in third reaction kettle again, you can be sliced, packed.Wherein, the second reaction unit includes autoclave body, kettle cover, chuck.The synthetic method of the raising phenylenediamine yields of the present invention, effectively reduces the cooling time in phenylenediamine crystallization process so that the yields of phenylenediamine reaches 90% or more.
Description
Technical field
The present invention is a kind of synthetic method of phenylenediamine, belongs to field of fine chemical, specially a kind of raising phenylenediamine is good
The synthetic method of product rate.
Background technology
Phenylenediamine is a kind of widely used organic chemical industry's intermediate, including three kinds of isomers, i.e. m-phenylene diamine (MPD), adjacent benzene two
Amine, p-phenylenediamine.P-phenylenediamine can be used for producing azo dyes, high molecular polymer, it can also be used to produce fur dyeing agent, rubber
Glue anti-aging agent and photo development agent, in addition p-phenylenediamine or the commonly sensitive reagents of inspection iron and copper.
It is p-phenylenediamine essence that finished product p-phenylenediamine product available on the market, which mainly has sheet and blocky two states, sheet,
Rear fine work condensation is evaporated to be sliced.Relative to bulk product, the phenylenediamine of sheet is because of its large contact area with air, radiating rate
Soon, so the ratio aoxidized during High-temperature cooling is smaller；But during conventional storage, the phenylenediamine of sheet is easy
Slowly oxidation influences the shelf life of product to gradually become grey, black by white in air.Therefore, the benzene of sheet
Diamines should be discharged air after dress use of unpacking and reseal, and be finished as early as possible.Block-like phenylenediamine product is relative to piece
Shape p-phenylenediamine, density bigger, thermal coefficient is low, while the contact area of block-like phenylenediamine and air is small, main oxidation
Process is all on surface, comparatively more resistant to storage.
The main production of domestic production bulk p-phenylenediamine is using paranitroanilinum as raw material, also by akali sulphide at present
It is former and obtain.Existing process has the following disadvantages：The yields of product is low, and yields is less than 80%；It is produced after reduction reaction
The raw a large amount of red water of sulfur compound, environmental pollution are serious；Reaction solution is difficult to take the method for rectifying, yield relatively low.It is existing
With the presence of the following disadvantage of reaction kettle：Traditional cooling means generally uses large volume of crystallization kettle, leads in external jacket
Enter low temperature, the mode of saturated salt solution (coolant liquid) cools down, but since blocky phenylenediamine contacts only on surface with air, and
Phenylenediamine density is big, and heat conductivility is poor, causes p-phenylenediamine liquid center cooling rate extremely slow, the oxidizable hair of the center portion thereof point
It is black, while causing non-defective unit phenylenediamine yield to reduce, also add the difficulty of non-defective unit screening.
In conclusion from storage with using in angle, block-like phenylenediamine product is more suitable for conventional use, storage,
Shelf-life is longer, but the synthesis technology of the prior art and the equal existing defects of equipment, causes the yields of finished product low.Meanwhile by
It condenses and is sliced after being by blocky phenylenediamine rectifying in sheet phenylenediamine, so sheet phenylenediamine can be regarded as by blocky benzene two
Amine increases the product that slice process obtains.Accordingly, it is desirable to provide a kind of synthetic method improving phenylenediamine yields and reaction are set
It is standby.
Invention content
To overcome the deficiencies of existing technologies, the present invention provides one kind effectively improving phenylenediamine yields, reduces waste liquid gives up
Gas pollutes, reduces the synthetic method of the p-phenylenediamine of labor intensity.
The purpose of the present invention is what is be achieved through the following technical solutions：
A kind of synthetic method improving p-phenylenediamine yields, includes the following steps：
(1) sodium sulfide solution is pumped into the first reaction kettle, cold water will be injected in the chuck of the first reaction kettle, then first
Paranitroanilinum is added in the autoclave body of reaction kettle, carries out reduction reaction；
(2) it is added in the autoclave body of the first reaction kettle and is restored anti-with step (1) equivalent nitroaniline, progress reduction reaction
Should after generate phenylenediamine solution, hypo solution and sodium hydroxide solution；
(3) analysis is sampled to the material in the first reaction kettle, when nitroaniline content is less than 1%, by reaction kettle
Interior temperature is down to 30 DEG C；
(4) by the vacuum distillation under vacuum of the material in the first reaction kettle, thio sulphur is distilled out under vacuum
Hypo solution is concentrated purified treatment by acid sodium solution；
(5) by the vacuum distillation under vacuum of remaining material in the first reaction kettle, benzene is distilled out under vacuum
Diamine solution；
(6) phenylenediamine solution that step (5) distills out is placed in the second reaction kettle and carries out crystallization treatment, phenylenediamine is made
Crude product；
(7) by made from step (6) phenylenediamine crude product carry out rectifying so that in phenylenediamine crude product phenylenediamine distillation and
The kettle top condenser of third reaction kettle is sublimated, and the phenylenediamine for the high-purity being collected into is sliced, is packed.
To further realize the present invention, the portion rate of vulcanized sodium and nitroaniline is 1.5~1.55 in the step (1):
1.15~1.25.
To further realize the present invention, reaction temperature is 55 DEG C in the step (1), and the reaction time is 1 hour.
To further realize the present invention, reaction temperature is 95 DEG C in the step (2), and the reaction time is 8 hours.
To further realize the present invention, material in the step (4) in the first reaction kettle is at a temperature of 95 DEG C of 85-
Vacuum distillation.
To further realize the present invention, in the step (5) in the first reaction kettle remaining material at 165-170 DEG C
At a temperature of vacuum distillation.
To further realize the present invention, the second reaction unit includes autoclave body, kettle cover, chuck, the kettle in the step (6)
Body is in flat cuboid, and removably facility is used to store the pallet of phenylenediamine liquid, the kettle cover and kettle in the autoclave body
Sealing rubber ring is equipped between body；Described to press from both sides the underface for being set on autoclave body, one end of the chuck is equipped with medium entrance, chuck
The other end be equipped with media outlet；The interior baffle being staggered equipped with multigroup parallel interval of the chuck so that in chuck
The S-shaped flowing of medium flows out media outlet from medium entrance detour.
To further realize the present invention, liquid level of the phenylenediamine solution in the second reaction kettle is in the step (6)
3-10cm。
To further realize the present invention, liquid level of the phenylenediamine solution in the second reaction kettle is in the step (6)
5-7cm。
To further realize the present invention, phenylenediamine crude product is 0 DEG C of 165-17, vacuum condition in temperature in the step (7)
Lower carry out rectifying.
Beneficial effects of the present invention：
(1) synthetic method of raising phenylenediamine yields of the invention, the synthetic method is using nitroaniline as raw material, vulcanization
Sodium is reducing agent, and reduction reaction occurs at high temperature, and nitroaniline is added in the first reaction kettle at twice so that reaction is more
Fully, be conducive to improve the yields in phenylenediamine building-up process.To generating phenylenediamine solution, thiosulfuric acid in the first reaction kettle
Sodium solution and sodium hydroxide solution vacuum distillation under vacuum, distill out hypo solution and phenylenediamine are molten successively
Liquid, then phenylenediamine solution crystallized, rectifying so that the impurity in the phenylenediamine of finished product is less, and precision is high, the benzene two of finished product
The yields of amine is high, by the phenylenediamine yields of the prior art less than 80%, is promoted to 90% or more.
(2) synthetic method of a kind of raising phenylenediamine yields of the invention, the second reaction unit packet in step (6)
Including autoclave body, kettle cover, chuck, wherein, autoclave body is in flat rectangular shape, and chuck is in flat rectangular shape, and the one of chuck
End is equipped with medium entrance, and the other end is equipped with media outlet；The interior baffle being staggered equipped with multigroup parallel interval of chuck so that
The S-shaped flowing of medium in chuck flows out media outlet from medium entrance detour.The setting of chuck Internal baffle effectively extends Jie
Flowing time of the matter in chuck, increases the contact area of medium and autoclave body bottom so that the area of heat exchange is big, and cooling is more
Add uniformly.It avoids corner when "-" type flow flows through reaction kettle to be easy to form vacuum, causes subregion heat exchange effect poor,
The inhomogeneous cooling for avoiding phenylenediamine solution phenylenediamine in crystallization process causes the problem that yields is low.
(3) synthetic method of a kind of raising phenylenediamine yields of the invention, vacuum distillation, distills out under vacuum
Sodium thiosulfate solution send to purification section and handled；There is a small amount of residue in distillation process, as dangerous solid
Waste is uniformly handled, and is not only reduced the impurity of finished product phenylenediamine, is improved yields, moreover, waste liquid focuses on
It avoids and pollutes the environment, recycling may be recovered to waste liquid.At exhaust gas centralized collection unification in second reaction kettle
Reason avoids the discharge pollution air of exhaust gas in autoclave body.
(4) synthetic method of a kind of raising phenylenediamine yields of the invention, in crystallization process, the liquid level of phenylenediamine is high
Degree control is 3-10cm, it is preferable that liquid level 5-7cm.The too low phenylenediamine crystal thickness for being easy to cause finished product of liquid level is not
It is enough, become the phenylenediamine of slabbing, oxidizable blackening during storage；Liquid level is too high, then the middle section heat of phenylenediamine liquid is handed over
It is low to change efficiency.It is easily aoxidized in cooling procedure.Therefore, in the level range of 3-10cm, the cooling velocity of phenylenediamine is ideal,
Black product rate is low；The bulk phenylenediamine being formed simultaneously can be further broken up into fritter packing, convenient for finished product phenylenediamine storage and make
With.
(5) synthetic method of a kind of raising phenylenediamine yields of the invention, it is in step (6) and set in the second reaction kettle
It is useful for the pallet of storage phenylenediamine liquid, convenient for the taking-up of final blocky phenylenediamine fine work after cooling, which reduce workers
Labor intensity, efficiency is high.
Description of the drawings
Fig. 1 is the structural schematic diagram of the crystallization kettle of the present invention；
Fig. 2 is sectional views of the Fig. 1 along AA ' tangent lines.
Specific implementation mode
Technical scheme of the present invention is illustrated With reference to embodiment.
A kind of synthetic method improving phenylenediamine yields, includes the following steps：
(1) first sodium sulfide solution is pumped into the first reaction kettle, cold water will be injected in the chuck of the first reaction kettle, then
Nitroaniline is added in the autoclave body of one reaction kettle, the first reaction kettle is to slowly warm up to 55 DEG C, it is small to be stirred reduction reaction 1
When；Wherein, the portion rate of vulcanized sodium and nitroaniline is 1.5~1.55:1.15~1.25；
(2) after reacting 1 hour, stop stirring and be added and step (1) equivalent nitrobenzene in the autoclave body of the first reaction kettle
Amine so that the portion rate of vulcanized sodium and nitroaniline is 1.5~1.55:2.3~2.5；The temperature in the first reaction kettle is delayed again
Slowly 95 DEG C are warming up to, stir and keep the temperature 8 hours；Phenylenediamine solution, thio sulphur are generated after reduction reaction occurs in first reaction kettle
Acid sodium solution and sodium hydroxide solution；
(3) analysis is sampled to the material in the first reaction kettle, when nitroaniline content is less than 1%, by reaction kettle
Interior temperature is down to 30 DEG C；
(4) conduction oil is added in the chuck of the first reaction kettle so that the first material in reactor is warming up to 85-95 DEG C；
Vacuum distillation is carried out to the material in the first reaction kettle under vacuum, sodium thiosulfate (100 DEG C of boiling point) is directly distilled
To receiving slit, the sodium thiosulfate solution that distills out, which is sent to purification section, to be handled；
(5) after the completion of sodium thiosulfate distillation, continue remaining temperature of charge in the first reaction kettle being promoted to 165-170
DEG C, phenylenediamine liquid is distilled out under vacuum；There is a small amount of residue in distillation process, unites as dangerous solid waste
One is handled；
(6) phenylenediamine solution that step (5) distills out is placed in the second reaction kettle and carries out crystallization treatment, phenylenediamine is made
Crude product；Wherein, liquid level of the phenylenediamine solution in the second reaction kettle is 3-10cm, it is preferable that the liquid level of phenylenediamine solution
Height is 5-7cm；
(7) phenylenediamine crude product made from step (6) is 165-170 DEG C, carries out rectifying under vacuum condition in temperature so that
Phenylenediamine in phenylenediamine crude product distils and sublimates in the kettle top condenser of third reaction kettle；By the benzene two for the high-purity being collected into
Amine is sliced, is packed, and a small amount of residue generated after rectifying unifies collection processing as danger.
As shown in Figs. 1-2, the synthetic method of a kind of raising phenylenediamine yields of the invention, second in step (6)
Reaction unit reaction kettle, the reaction kettle include autoclave body 1, kettle cover 2 and chuck 3, wherein：
Autoclave body 1 provides for the synthesis of phenylenediamine and space occurs for containing reaction solution.Autoclave body 1 is in flat rectangular
The bodily form, autoclave body 1 are made of stainless steel, and autoclave body 1 is realized using the prior art.Further, it is removably set in autoclave body
The pallet 11 for storing phenylenediamine liquid is set, facilitates taking-up and the stripping and slicing processing of blocky phenylenediamine after cooling, reduces labor
Fatigue resistance so that efficiency higher.
Kettle cover 2 is used to close the opening portion of autoclave body 1, and cooperation autoclave body 1 provides the space of sealing for the synthesis of phenylenediamine.Kettle cover
2 are equipped with charge door 21, and charge door 21 is equipped with charging valve, and pipeline is placed in by charge door in autoclave body 1 by when charging so that pipeline
At 2-3cm above pallet, liquid splash is avoided.Sealing rubber ring is equipped between kettle cover 2 and autoclave body 1, for preventing in autoclave body 1
The leakage of liquid/gas.Kettle cover 2 selects high temperature resistant, pressure resistance, iron covering or stainless steel cover not easy to crack.It is equipped in kettle cover 2 anti-
Corrosion protection layer effectively avoids corrosion of the corrosive gas to kettle cover 2；Wherein, corrosion protective layer is plastic coating of fluoride, preferably
Ground, fluoroplastics are polytetrafluoroethylene (PTFE), perfluoroethylene-propylene or PFA plastics.
Chuck 3 is for coordinating autoclave body 1 to realize the functions such as heating in chemical reaction process, cooling.Chuck 3 is arranged in autoclave body 1
Underface, chuck 3 is in flat rectangular shape, and one end of chuck 3 is equipped with medium entrance 31, and the other end is equipped with media outlet
32；The interior baffle 33 being staggered equipped with multigroup parallel interval of chuck 3 so that the S-shaped flowing of medium in chuck 3, from Jie
31 detour of matter import flows out media outlet 32.When the setting of 3 Internal baffle 33 of chuck extends flowing of the medium in chuck 3
Between, increase the contact area of medium and 1 bottom of autoclave body so that the area of heat exchange is big, and condensation/heat conduction is uniform.
The foregoing is merely the better embodiments of the present invention, and the invention is not limited in the above embodiments, are implementing
There may be the small structural modifications in part in the process, if the various changes or modifications of the present invention are not departed from the essence of the present invention
God and range, and belong within the scope of the claim and equivalent technologies of the present invention, then the present invention is also intended to comprising these changes
And modification.
Claims (10)
1. a kind of synthetic method improving phenylenediamine yields, which is characterized in that include the following steps：
(1) sodium sulfide solution is pumped into the first reaction kettle, cold water will be injected in the chuck of the first reaction kettle, then in the first reaction
Nitroaniline is added in the autoclave body of kettle, carries out reduction reaction；
(2) it is added in the autoclave body of the first reaction kettle and step (1) equivalent paranitroanilinum, progress reduction reaction, reduction reaction
Phenylenediamine solution, hypo solution and sodium hydroxide solution are generated afterwards；
(3) analysis is sampled to the material in the first reaction kettle, it, will be in reaction kettle when p-nitrophenyl amine content is less than 1%
Temperature is down to 30 DEG C；
(4) by the vacuum distillation under vacuum of the material in the first reaction kettle, sodium thiosulfate is distilled out under vacuum
Hypo solution is concentrated purified treatment by solution；
(5) by the vacuum distillation under vacuum of remaining material in the first reaction kettle, phenylenediamine is distilled out under vacuum
Solution；
(6) phenylenediamine solution that step (5) distills out is placed in the second reaction kettle and carries out crystallization treatment, it is thick that phenylenediamine is made
Product；
(7) phenylenediamine crude product made from step (6) is subjected to rectifying so that p-phenylenediamine distillation in phenylenediamine crude product and the
The kettle top condenser of three reaction kettles is sublimated, and the phenylenediamine for the high-purity being collected into is sliced, is packed.
2. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(1) portion rate of vulcanized sodium and nitroaniline is 1.5~1.55 in:1.15~1.25.
3. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(1) reaction temperature is 55 DEG C in, and the reaction time is 1 hour.
4. a kind of synthetic method improving p-phenylenediamine yields according to claim 1, which is characterized in that the step
(2) reaction temperature is 95 DEG C in, and the reaction time is 8 hours.
5. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(4) material in the first reaction kettle vacuum distillation at a temperature of 85-95 DEG C.
6. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(5) remaining material vacuum distillation at a temperature of 165-170 DEG C in the first reaction kettle in.
7. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(6) the second reaction unit includes autoclave body, kettle cover, chuck in, and the autoclave body is in flat cuboid, in the autoclave body removably
Facility is used to store the pallet of phenylenediamine liquid, and sealing rubber ring is equipped between the kettle cover and autoclave body；The folder is set on kettle
One end of the underface of body, the chuck is equipped with medium entrance, and the other end of chuck is equipped with media outlet；It is set in the chuck
There is the baffle that multigroup parallel interval is staggered so that the S-shaped flowing of medium in chuck flows out medium from medium entrance detour
Outlet.
8. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(6) liquid level of the phenylenediamine solution in the second reaction kettle is 3-10cm in.
9. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(6) liquid level of the phenylenediamine solution in the second reaction kettle is 5-7cm in.
10. a kind of synthetic method improving phenylenediamine yields according to claim 1, which is characterized in that the step
(7) phenylenediamine crude product is 165-170 DEG C, carries out rectifying under vacuum condition in temperature in.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117486729A (en) * | 2023-11-02 | 2024-02-02 | 定远县尚时新材料有限公司 | Production method and production device for p-phenylenediamine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491905A (en) * | 2011-11-18 | 2012-06-13 | 江苏科圣化工装备工程有限公司 | Method and device for co-production of o-phenylenediamine and p-phenylenediamine |
| CN102531921A (en) * | 2010-12-24 | 2012-07-04 | 中国石油化工股份有限公司 | Refining and shaping process of p-phenylenediamine |
| CN106316863A (en) * | 2016-08-13 | 2017-01-11 | 安徽东至广信农化有限公司 | Efficient o-phenylenediamine recovery method |
-
2018
- 2018-04-27 CN CN201810393439.3A patent/CN108610261B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102531921A (en) * | 2010-12-24 | 2012-07-04 | 中国石油化工股份有限公司 | Refining and shaping process of p-phenylenediamine |
| CN102491905A (en) * | 2011-11-18 | 2012-06-13 | 江苏科圣化工装备工程有限公司 | Method and device for co-production of o-phenylenediamine and p-phenylenediamine |
| CN106316863A (en) * | 2016-08-13 | 2017-01-11 | 安徽东至广信农化有限公司 | Efficient o-phenylenediamine recovery method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117486729A (en) * | 2023-11-02 | 2024-02-02 | 定远县尚时新材料有限公司 | Production method and production device for p-phenylenediamine |
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