CN106938973B - A kind of method of the separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture - Google Patents
A kind of method of the separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture Download PDFInfo
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- CN106938973B CN106938973B CN201710190933.5A CN201710190933A CN106938973B CN 106938973 B CN106938973 B CN 106938973B CN 201710190933 A CN201710190933 A CN 201710190933A CN 106938973 B CN106938973 B CN 106938973B
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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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Abstract
The present invention relates to a kind of methods that single column heterogeneous azeotropic rectification detaches aniline and ethylene glycol azeotropic mixture.This method is using hexamethylene as entrainer, hexamethylene is passed through azeotropy rectification column top, it is come into full contact with the aniline and ethylene glycol azeotropic mixture entered in the middle part of tower, bottom of tower produces high purity product aniline, the heterogeneous azeotrope that hexamethylene is formed with ethylene glycol is steamed from tower top, by being thermally integrated technique, overhead vapours is preheated as heat source to raw material first, then enter phase-splitter split-phase after being condensed by auxiliary condenser, lower layer's product ethylene glycol directly produces in phase-splitter, and upper layer hexamethylene returns to azeotropy rectification column and recycles.The present invention solves the problems, such as that aniline glycol system forms minimum azeotropic mixture and difficult separation under normal pressure, using single column separating azeotrope, and realizes and is thermally integrated, and has many advantages, such as that low energy consumption, product yield is high, simple for process.
Description
【Technical field】
Field is isolated and purified the invention belongs to chemical industry, and in particular to a kind of single column heterogeneous azeotropic rectification Separation of Benzene
The method of amine and ethylene glycol azeotropic mixture.
【Background technology】
Aniline, be a hydrogen atom in benzene molecular replaced by amino and the compound that generates, physical property is colourless
Or yellowish oily liquids, have an overpowering odor, have alkalinity in terms of chemical property, can with acidified symphysis hydrochloric acid salt, with sulfuric acid
It is combined to sulfate.Aniline is one of most important intermediate in dye industry, and dyestuff nigrosine is used in printing and dyeing industry；
For producing many insecticides, fungicide, such as DDV, nitrofen, propachlor in pesticide industry；Aniline is the weight of rubber chemicals
Raw material is wanted, for manufacturing anti-aging agent etc.；Also can be used as the raw material of medical sulfa drug, at the same be also production fragrance, plastics, varnish,
The intermediate etc. of film etc..Ethylene glycol is commonly called as glycol, is the viscous liquid of water white transparency at normal temperatures, as important basis
One of Organic Ingredients, mainly for the production of polyester fiber, unsaturated polyester resin, antifreezing agent, the lubricant of cosmetics, plasticising
Agent, nonionic surfactant and explosive etc. can be additionally used in the row such as coating, photograph developer solution, brake-fluid and ink in addition
Industry, purposes are very extensive.
Using aniline as the indoles of Material synthesis also known as benzopyrrole, it is usually used in the intermediate of medicine and pesticide, can manufactures
The drugs such as antipyretic-antalgic agent, excitant, blood pressure lowering and vasodilator, in pesticide can plant growth conditioning agent processed, fungicide etc.,
It is also widely used in perfumery.When using aniline as Material synthesis indoles, also need that a large amount of ethylene glycol are added, therefore in last handling process
The mixture of meeting a large amount of aniline and ethylene glycol, and aniline forms azeotropic mixture with ethylene glycol under normal pressure, conventional distillation method is difficult to
Separation reduces environmental pollution, need to be effectively separated to aniline and ethylene glycol to reduce production cost.
Patent (CN103396290A) discloses a kind of separation ethylene glycol and 1, and the technique of 2- butanediols, the technique is with first
Benzene, ethylbenzene, dimethylbenzene etc. are entrainer, and ethylene glycol and 1, the separation of 2- butanediols, the technique energy are realized using rectifying column single column
Consumption is high, and product purity only has 98%, and commercial Application is not implemented.
Patent (CN105130755A) discloses a kind of method of separation neopentyl glycol and ethylene glycol mixture, and this method is
Using dimethylbenzene as entrainer, the separation of neopentyl glycol and ethylene glycol, technique separation are realized using rectifying column and solvent recovery tower
Mode is complicated, high energy consumption, and product purity is not high.
Patent (CN106349107A) discloses a kind of method of separating acetonitrile and triethylamine mixture and suitable for should
The device of method, the technique realize point of acetonitrile and triethylamine using azeotropy rectification column and stripper using n-hexane as entrainer
From the technique separate mode is complicated, high energy consumption.
Document (azeotropic distillation separating alcohol-isopropanol, mythical bird like the phoenix etc., chemical industry progress, volume 31, the 10th phase, 2187-
Page 2190, publication date is on December 19th, 2012) disclose a kind of technique of separating alcohol and isopropanol, the technique be with 1- oneself
Alkene is entrainer, although carrying out the separation of ethyl alcohol and isopropanol using single column, which only isolates isopropanol, fail to realize
The separation of ethyl alcohol, and product purity is not high.
There are many article and patent in terms of in relation to azeotropic distillation, there is not yet the azeotropic distillation separation aniline and second published
Data in terms of glycol azeotropic mixture.The present invention realizes two components using hexamethylene as entrainer, using azeotropy rectification column, phase-splitter
Separation and entrainer recycle.The suitable aniline mass fraction of the method for the present invention accounts for aniline-ethylene glycol of 60%-80%
Azeotropic mixture system.The present invention detaches for single column, while cost-effective, realizes the high-purity separation of azeotropic mixture；Pass through what is be thermally integrated
Mode realizes the recycling of heat in technique, saves energy consumption；It is simple for process, it is easy to operate.
【Invention content】
[technical problems to be solved]
The object of the present invention is to provide a kind of methods that single column heterogeneous azeotropic rectification detaches aniline and ethylene glycol azeotropic mixture.
It is a further object to provide a kind of single column heterogeneous azeotropic rectification separation aniline and ethylene glycol azeotropic mixture
Device.
It is a further object to provide the methods to detach aniline and ethylene glycol in single column heterogeneous azeotropic rectification
Application in azeotropic mixture.
[technical solution]
The present invention is achieved through the following technical solutions.
A kind of method of the separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture, it is characterised in that for detaching
The device of aniline and ethylene glycol azeotropic mixture includes mainly with lower part：
Azeotropy rectification column (T1), reboiler (R1), heat exchanger (H1), auxiliary condenser (C1), phase-splitter (DEC), pump
(P1), (P2) is pumped；Wherein reboiler (R1) is connected to the bottom of tower azeotropy rectification column (T1), heat exchanger (H1) is connected to azeotropy rectification column
(T1) tower top, auxiliary condenser (C1) are connected with heat exchanger (H1), and phase-splitter (DEC) is connected with auxiliary condenser (C1).
Detaching aniline using single column heterogeneous azeotropic rectification, with the method for ethylene glycol mixture to detach the azeotropic system main
Include the following steps：
(1) aniline and ethylene glycol mixture are entered after heat exchanger (H1) preheating in azeotropy rectification column (T1), carries out benzene
The aniline product of the separation of amine and ethylene glycol, high-purity is directly produced from tower reactor, and ethylene glycol and hexamethylene azeotropic mixture are with gas phase
Form steams 4 entrance heat exchanger (H1) by the road from tower top, further into auxiliary condenser (C1) by pipeline 5 after heat exchange
Condensation, finally enters phase-splitter (DEC) split-phase；
(2) in phase-splitter (DEC), ethylene glycol is layered with hexamethylene, and upper layer hexamethylene is returned to by pipeline 7 through pump (P2)
It is recycled in azeotropy rectification column (T1), lower layer's product ethylene glycol is directly produced from phase-splitter (DEC)；
(3) it realizes and is thermally integrated in heat exchanger (H1), the gas phase azeotropic mixture ethylene glycol and hexamethylene that tower top steams are used as and change
The hot logistics of hot device (H1), to as cold logistics aniline and ethylene glycol mixture preheated；
In accordance with another preferred embodiment of the present invention, it is characterised in that：Azeotropy rectification column (T1) behaviour that the present invention uses
It is 1atm to make pressure, and theoretical cam curve is 15~25 pieces, and feed entrance point is the 5th~8 block of column plate, and recycle flows into material position and is set to the
1 block of column plate.
In accordance with another preferred embodiment of the present invention, it is characterised in that：Benzene in aniline and glycol system to be separated
The mass fraction of amine is 60%~80%.
In accordance with another preferred embodiment of the present invention, it is characterised in that：The azeotropy rectification column works under normal pressure,
Azeotropic distillation column overhead temperatures are 78.0 DEG C~83.0 DEG C, and bottom temperature is 180.0 DEG C~185.0 DEG C.
In accordance with another preferred embodiment of the present invention, it is characterised in that：After separation the purity of aniline be 99.95%~
99.99%, the yield of aniline is 99.95%~99.99%, and the purity of ethylene glycol is 99.95%~99.99%, ethylene glycol
Yield is 99.90%~99.99%.
The method of single column heterogeneous azeotropic rectification separation aniline-ethylene glycol mixture is described in detail below in the present invention：
Aniline and ethylene glycol azeotropic mixture are entered into heat exchanger (H1) by pipeline 1, it is defeated through pump (P1) by pipeline 2 after heat exchange
It send to azeotropy rectification column (T1)；In azeotropy rectification column (T1), high purity product aniline is produced from tower reactor, ethylene glycol and hexamethylene
Azeotropic mixture steams 4 entrance heat exchanger (H1) by the road in the form of gas phase from tower top, cold into assisting by pipeline 5 after heat exchange
Condenser (C1) further condenses, and finally enters phase-splitter (DEC)；In phase-splitter (DEC), azeotropic mixture ethylene glycol and hexamethylene point
Layer, hexamethylene is returned in azeotropy rectification column (T1) by pipeline 7 and is recycled at the middle and upper levels, lower layer's product ethylene glycol directly from point
Phase device (DEC) produces.
Azeotropy rectification column (T1) operating pressure that the present invention uses is 1atm, and theoretical cam curve is 15~25 pieces, feed position
It is set to the 5th~8 block of column plate, recycle flows into material position and is set to the 1st block of column plate.The tower top temperature of azeotropy rectification column be 78.0 DEG C~
83.0 DEG C, bottom temperature is 180.0 DEG C~185.0 DEG C.
The purity of aniline is 99.95%~99.99% after present invention separation, the yield of aniline is 99.95%~
99.99%, the purity of ethylene glycol is 99.95%~99.99%, and the yield of ethylene glycol is 99.90%~99.99%.
[advantageous effect]
The present invention compared with prior art, mainly there is following advantageous effect：
(1) it is successfully separated aniline and ethylene glycol binary system, obtains two kinds of high purity products, aniline and ethylene glycol yield
It is high.
(2) technique realization is thermally integrated, and reduces energy consumption.
(3) compared with traditional azeotropic distillation technique, single-tower operation of the present invention is simple for process, equipment investment expense is low.
【Description of the drawings】
Attached drawing 1 is the structural schematic diagram that single column heterogeneous azeotropic rectification detaches aniline and ethylene glycol azeotropic mixture.
In figure, T1 azeotropy rectification columns；R1 reboilers；C1 condensers；H1 heat exchangers；P1 is pumped；P2 is pumped；Each logistics of digital representation
Pipeline.
【Specific implementation mode】
Embodiment 1：
It is 1atm (absolute pressure) in operating pressure, the number of plates is in the azeotropy rectification column of 15 blocks of plates, by 1000kg aniline quality
Score accounts for 60% aniline-ethylene glycol mixture and enters the tower in the 5th block of column plate after preheating, and entrainer hexamethylene is from the 1st
Block column plate is recycled into the tower, and tower top temperature is 78.2 DEG C, and bottom temperature is 180.0 DEG C；After heat exchanger exchanges heat, ethylene glycol
Partial condensation, then through the further condensation temperature of auxiliary condenser be 30 DEG C.Aniline mass fraction after separation is 99.98%, is received
Rate is 99.95%；Quality of glycol score after separation is 99.97%, yield 99.93%.
Embodiment 2：
It is 1atm (absolute pressure) in operating pressure, the number of plates is in the azeotropy rectification column of 18 blocks of plates, by 1000kg aniline quality
Score accounts for 65% aniline-ethylene glycol mixture and enters the tower in the 6th block of column plate after preheating, and entrainer hexamethylene is from the 1st
Block column plate is recycled into the tower, and tower top temperature is 79.5 DEG C, and bottom temperature is 181.0 DEG C；After heat exchanger exchanges heat, ethylene glycol
Partial condensation, then through the further condensation temperature of auxiliary condenser be 30 DEG C.Aniline mass fraction after separation is 99.96%, is received
Rate is 99.95%；Quality of glycol score after separation is 99.97%, yield 99.95%.
Embodiment 3：
It is 1atm (absolute pressure) in operating pressure, the number of plates is in the azeotropy rectification column of 20 blocks of plates, by 1000kg aniline quality
Score accounts for 70% aniline-ethylene glycol mixture and enters the tower in the 7th block of column plate after preheating, and entrainer hexamethylene is from the 1st
Block column plate is recycled into the tower, and tower top temperature is 81.0 DEG C, and bottom temperature is 182.0 DEG C；After heat exchanger exchanges heat, ethylene glycol
Partial condensation, then through the further condensation temperature of auxiliary condenser be 30 DEG C.Aniline mass fraction after separation is 99.98%, is received
Rate is 99.98%；Quality of glycol score after separation is 99.97%, yield 99.98%.
Embodiment 4：
It is 1atm (absolute pressure) in operating pressure, the number of plates is in the azeotropy rectification column of 22 blocks of plates, by 1000kg aniline quality
Score accounts for 75% aniline-ethylene glycol mixture and enters the tower in the 6th block of column plate after preheating, and entrainer hexamethylene is from the 1st
Block column plate is recycled into the tower, and tower top temperature is 81.0 DEG C, and bottom temperature is 183.0 DEG C；After heat exchanger exchanges heat, ethylene glycol
Partial condensation, then through the further condensation temperature of auxiliary condenser be 30 DEG C.Aniline mass fraction after separation is 99.95%, is received
Rate is 99.98%；Quality of glycol score after separation is 99.97%, yield 99.98%.
Embodiment 5：
It is 1atm (absolute pressure) in operating pressure, the number of plates is in the azeotropy rectification column of 25 blocks of plates, by 1000kg aniline quality
Score accounts for 80% aniline-ethylene glycol mixture and enters the tower in the 8th block of column plate after preheating, and entrainer hexamethylene is from the 1st
Block column plate is recycled into the tower, and tower top temperature is 82.0 DEG C, and bottom temperature is 184.0 DEG C；After heat exchanger exchanges heat, ethylene glycol
Partial condensation, then through the further condensation temperature of auxiliary condenser be 30 DEG C.Aniline mass fraction after separation is 99.98%, is received
Rate is 99.97%；Quality of glycol score after separation is 99.97%, yield 99.97%.
Claims (5)
1. a kind of method of the separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture, it is characterised in that realize this method
Device mainly include with lower part：
Azeotropy rectification column (T1), reboiler (R1), heat exchanger (H1), auxiliary condenser (C1), phase-splitter (DEC), pump (P1), pump
(P2)；Wherein reboiler (R1) is connected to the bottom of tower azeotropy rectification column (T1), and heat exchanger (H1) is connected to azeotropy rectification column (T1) tower
Top, auxiliary condenser (C1) are connected with heat exchanger (H1), and phase-splitter (DEC) is connected with auxiliary condenser (C1)；
The azeotropic mixture is detached using the method for single column heterogeneous azeotropic rectification to mainly include the following steps that：
(1) aniline and ethylene glycol mixture are entered after heat exchanger (H1) preheating in azeotropy rectification column (T1), carry out aniline and
The product aniline of the separation of ethylene glycol, high-purity is directly produced from tower reactor, and ethylene glycol and hexamethylene azeotropic mixture are in the form of gas phase
It is steamed from tower top and enters heat exchanger (H1) by the road (4), it is further into auxiliary condenser (C1) by pipeline (5) after heat exchange
Condensation, finally enters phase-splitter (DEC) split-phase；
(2) in phase-splitter (DEC), ethylene glycol is layered with hexamethylene, and upper layer hexamethylene is returned to altogether by pipeline (7) through pump (P2)
It is recycled in boiling rectifying column (T1), lower layer's product ethylene glycol is directly produced from phase-splitter (DEC)；
(3) it realizes and is thermally integrated in heat exchanger (H1), the gas phase azeotropic mixture ethylene glycol and hexamethylene that tower top steams are as heat exchanger
(H1) hot logistics, to as cold logistics aniline and ethylene glycol mixture preheated；
Azeotropy rectification column (T1) operating pressure is 1atm, and theoretical cam curve is 15~25 pieces, and feed entrance point is the 5th~8 block of column plate,
Recycle flows into material position and is set to the 1st block of column plate.
2. the method for a kind of separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture according to claim 1,
It is characterized in that：Entrainer is done using hexamethylene, hexamethylene forms heterogeneous azeotrope with ethylene glycol, can directly pass through phase-splitter
The product ethylene glycol of isolated high-purity.
3. the method for a kind of separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture according to claim 1,
It is characterized in that：The ratio between entrainer and mixture quality flow to be separated are that solvent ratio is 15~25, aniline to be separated and second
The mass fraction of aniline is 60%~80% in diol system.
4. the method for a kind of separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture according to claim 1,
It is characterized in that：The azeotropy rectification column works under normal pressure, and the tower top temperature of azeotropy rectification column is 78.0 DEG C~83.0 DEG C,
Bottom temperature is 180.0 DEG C~185.0 DEG C.
5. the method for a kind of separation of single column heterogeneous azeotropic rectification aniline and ethylene glycol azeotropic mixture according to claim 1,
It is characterized in that：The product of two kinds of high-purities can be isolated using single column, after separation the purity of aniline be 99.95%~
99.99%, the yield of aniline is 99.95%~99.99%, and the purity of ethylene glycol is 99.95%~99.99%, ethylene glycol
Yield is 99.90%~99.99%.
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193594B (en) * | 2012-01-10 | 2015-01-07 | 中国石油化工股份有限公司 | Method for separating ethylene glycol and 1, 2-butanediol |
| CN102701994A (en) * | 2012-06-01 | 2012-10-03 | 中国科学院研究生院 | Process method for separating and refining rough aniline |
| CN103396290A (en) * | 2013-07-08 | 2013-11-20 | 吉林化工学院 | Novel process for separating ethylene glycol and 1,2-butanediol |
| CN104926608B (en) * | 2014-03-17 | 2017-04-12 | 中国石油化工股份有限公司 | Method for separating ethylene glycol and 1,2-butanediol |
| CN105130755A (en) * | 2015-07-24 | 2015-12-09 | 常州大学 | Method of separating mixture of neopentyl glycol and ethylene glycol |
| CN106554299A (en) * | 2015-09-29 | 2017-04-05 | 中国石油化工集团公司 | A kind of method of coproduction 3- methylindole and indole |
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