CN104230940B - The separation method of triethylene diamine - Google Patents
The separation method of triethylene diamine Download PDFInfo
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- CN104230940B CN104230940B CN201310236942.5A CN201310236942A CN104230940B CN 104230940 B CN104230940 B CN 104230940B CN 201310236942 A CN201310236942 A CN 201310236942A CN 104230940 B CN104230940 B CN 104230940B
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
The present invention relates to the separation method of a kind of triethylene diamine, the problem mainly separating difficulty present in solution prior art.The present invention continuously enters azeotropy rectification column by using triethylene diamine crystalline hydrate or triethylene diamine aqueous solution, entrainer joins azeotropy rectification column tower reactor, water and entrainer form azeotropic mixture and steam from tower top, after condensation split-phase, aqueous phase separation is to outside system, organic facies reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product;Described entrainer is selected from C6~C10In hydro carbons at least one and selected from C2~C8The technical scheme of the compositions that at least one in esters is formed preferably solves this problem, can be used in the commercial production of anhydrous triethylene diamine.
Description
Technical field
The present invention relates to triethylene diamine production field, the particularly separation of triethylene diamine-aqueous systems.
Background technology
Triethylene diamine is important fine chemical material, and purposes is extremely wide, is the kicker kind that in polyurethane industrial, usage amount is maximum, purposes is the widest.Its series of products are applicable to the various products such as polyurethane foam, elastomer and coating.It also is used as acrylonitrile, ethylene rolymerization catalyst and the polymerization catalyst of epoxyalkane hydrocarbon.
Triethylene diamine easily deliquescence, soluble in water, and forming crystalline hydrate six water triethylene diamine with water, crystalline hydrate and triethylene diamine aqueous solution dehydration are the most relatively difficult, and the dehydration the most effectively realizing this triethylene diamine-aqueous systems is the key issue faced.
Through retrieval, have no the pertinent literature report that triethylene diamine-aqueous mixtures system separates.
Summary of the invention
The technical problem to be solved is the problem that triethylene diamine present in prior art-aqueous mixtures separates difficulty, it is provided that a kind of new separate triethylene diamine and the method for water.It is short that the method has technological process, and equipment investment is few, simple to operate, and economical and effective is easy to control, product purity advantages of higher.
For solving above-mentioned technical problem, the technical solution used in the present invention is: the separation method of a kind of triethylene diamine, triethylene diamine crystalline hydrate or triethylene diamine aqueous solution continuously enter azeotropy rectification column, entrainer joins azeotropy rectification column tower reactor, water and entrainer form azeotropic mixture and steam from tower top, after condensation split-phase, outside aqueous phase separation to system, organic facies reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product;Described entrainer is selected from C6~C10In hydro carbons at least one and selected from C2~C8The compositions that at least one in esters is formed.
In technique scheme, in triethylene diamine crystalline hydrate or triethylene diamine aqueous solution, water: the mass ratio of triethylene diamine is preferably 1:99 ~ 99:1;The theoretical cam curve of azeotropy rectification column is preferably 20 ~ 60, and more preferably 20 ~ 45;Reflux ratio is preferably 0.4 ~ 5, and more preferably 0.4 ~ 2;The tower top operation pressure of azeotropy rectification column is preferably 30 ~ 100kPa, more preferably 30 ~ 90kPa;Tower top temperature is preferably 40 ~ 120 DEG C, more preferably 40 ~ 90 DEG C;Tower reactor operation pressure is preferably 50 ~ 130 kPa, and more preferably 50 ~ 110
kPa;Bottom temperature is preferably 120 ~ 200 DEG C, more preferably 140 ~ 180 DEG C;Entrainer is preferably by least one in benzene,toluene,xylene, normal octane, isobutyltrimethylmethane. and at least one compositions formed in methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate;In entrainer, at least one in benzene,toluene,xylene, normal octane, isobutyltrimethylmethane. is preferably 90:10 ~ 10:90 with the mass ratio of at least one in methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, more preferably 90:10 ~ 50:50;The mass ratio of the water in entrainer and piperazine crystalline hydrate or entrainer are preferably 3:1 ~ 15:1 with the mass ratio of the water in piperazine aqueous solution.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Hydro carbons such as toluene, dimethylbenzene uses as excellent entrainer particularly water entrainer always, but hydro carbons particularly benzene class material water amount is more than esters less than esters, the latent heat of vaporization, and has stronger toxicity.The toluene latent heat of vaporization is 362kJ/kg, and the benzene latent heat of vaporization is 390kJ/kg, and the sec-butyl acetate latent heat of vaporization is 313kJ/kg, and the n-butyl acetate latent heat of vaporization is 339kJ/kg.The feature that band outlet capacity is strong although n-butyl acetate, sec-butyl acetate have, the latent heat of vaporization is little, and be environment-friendly type solvent, but in water, dissolubility is big, loses bigger in phase process.Inventor has surprisingly found that in research process, if entrainer uses selected from C6~C10In hydro carbons at least one and selected from C2~C8The compositions that at least one in esters is formed, it is possible to obtain beyond thought technique effect, its separating effect and economy are better than and individually use C6~C10At least one in hydro carbons is as entrainer or individually uses selected from C2~C8At least one in esters is as entrainer, and effect is not individually to use C6~C10At least one in hydro carbons is as entrainer income effect and individually uses selected from C2~C8At least one in esters is as the simple superposition of entrainer income effect.
Triethylene diamine crystalline hydrate is six water triethylene diamines, forms the hydrogen bond of complexity between hydrone and triethylene diamine molecule.When the temperature increases, the kinetic energy of hydrone increases, water of crystallization breaks through the tendency of lattice constraint and increases, and the tendency returning to go in lattice reduces, so the hydration number of triethylene diamine crystalline hydrate molecule will reduce until all taking off, while hydrone departs from triethylene diamine, the present invention forms minimum point temperature azeotropic mixture by adding entrainer water with entrainer, removes from tower top, after condensation split-phase, organic facies reflux cycle band water, discharge.
Use technical scheme, easy to operate, it is easy to control, triethylene diamine product purity can reach 99.5wt% and more than, achieve preferable technique effect.
Below by embodiment, the invention will be further elaborated, but the scope of the present invention is in no case construed as limiting by these embodiments.
Accompanying drawing explanation
Fig. 1 is the process chart of separation of the present invention triethylene diamine-aqueous systems.
In Fig. 1,1 is azeotropy rectification column, and 2 is phase separator, and 3 feed for triethylene diamine aqueous solution, and 4 is azeotropy rectification column tower overhead gas, and 5 is overhead condensation liquid, and 6 is organic facies, and 7 is aqueous phase, and 8 is anhydrous triethylene diamine product.
Detailed description of the invention
[embodiment 1]
Three water triethylene diamine crystalline hydrates continuously enter azeotropy rectification column, entrainer toluene and n-propyl acetate mixture disposably join azeotropy rectification column tower reactor, water and entrainer form minimum point azeotropic mixture, steam from tower top, after condensation split-phase, outside aqueous phase to system, organic facies mainly contains entrainer, reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Three water triethylene diamine crystalline hydrate feed rates are 1000kg/h, and wherein the quality of water and triethylene diamine is 32.5:67.5, and feed pressure is 120kPa.In entrainer toluene and n-propyl acetate mixture and three water triethylene diamine crystalline hydrates, the mass ratio that mass ratio is 5.1:1, toluene and n-propyl acetate of water is 90:10, and azeotropy rectification column operating parameter is as shown in table 1.Logistics composition is as shown in table 2.
Table 1
Azeotropy rectification column | Operating parameter |
Tower top operation pressure/kPa (A) | 30 |
Tower reactor operation pressure/kPa (A) | 50 |
Tower top temperature/DEG C | 54 |
Bottom temperature/DEG C | 150 |
Reflux ratio | 0.55 |
Theoretical cam curve | 35 |
Table 2
Logistics (mass percent) | 7 | 8 |
Water | 99.8 | < 0. 1 |
Triethylene diamine | 0 | > 99.9 |
Toluene, n-propyl acetate | 0.2 | 0 |
Flow (kg/h) | 325.6 | 675 |
[embodiment 2]
Six water triethylene diamine crystalline hydrates continuously enter azeotropy rectification column, entrainer xylol and ethyl acetate mixture disposably join azeotropy rectification column tower reactor, water and entrainer form minimum point azeotropic mixture, steam from tower top, after condensation split-phase, outside aqueous phase to system, organic facies mainly contains entrainer, reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Six water triethylene diamine crystalline hydrate feed rates are 1000kg/h, and wherein the quality of water and triethylene diamine is 49.1:50.9, and feed pressure is 120kPa.In entrainer xylol and ethyl acetate mixture and three water triethylene diamine crystalline hydrates, the mass ratio that mass ratio is 3.5:1, xylol and ethyl acetate of water is 50:50, and azeotropy rectification column operating parameter is as shown in table 3.Logistics composition is as shown in table 4.
Table 3
Azeotropy rectification column | Operating parameter |
Tower top operation pressure/kPa (A) | 50 |
Tower reactor operation pressure/kPa (A) | 80 |
Tower top temperature/DEG C | 70 |
Bottom temperature/DEG C | 166 |
Reflux ratio | 0.38 |
Theoretical cam curve | 45 |
Table 4
Logistics (mass percent) | 7 | 8 |
Water | 98.0 | < 0.1 |
Triethylene diamine | 0 | 99.9 |
Xylol, ethyl acetate | 2.0 | 0 |
Flow (kg/h) | 501 | 509.3 |
[embodiment 3]
Triethylene diamine aqueous solution continuously enters azeotropy rectification column, entrainer toluene and sec-butyl acetate mixture disposably join azeotropy rectification column tower reactor, water and entrainer form minimum point azeotropic mixture, steam from tower top, after condensation split-phase, outside aqueous phase to system, organic facies mainly contains entrainer, reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Triethylene diamine aqueous solution feed rate is 1000kg/h, and wherein the mass ratio of water and triethylene diamine is 90:10, and feed pressure is 120kPa.In entrainer toluene and sec-butyl acetate mixture and three water triethylene diamine crystalline hydrates, the mass ratio that mass ratio is 4.5:1, toluene and sec-butyl acetate of water is 30:70, and azeotropy rectification column operating parameter is as shown in table 5.Logistics composition is as shown in table 6.
Table 5
Azeotropy rectification column | Operating parameter |
Tower top operation pressure/kPa (A) | 80 |
Tower reactor operation pressure/kPa (A) | 100 |
Tower top temperature/DEG C | 80 |
Bottom temperature/DEG C | 172 |
Reflux ratio | 0.50 |
Theoretical cam curve | 30 |
Table 6
Logistics (mass percent) | 7 | 8 |
Water | 99.3 | < 0.1 |
Triethylene diamine | 0 | > 99.9 |
Toluene, sec-butyl acetate | 0.7 | 0 |
Flow (kg/h) | 906.3 | 100.1 |
[embodiment 4]
Triethylene diamine aqueous solution continuously enters azeotropy rectification column, entrainer normal heptane and ethyl acetate mixture disposably join azeotropy rectification column tower reactor, water and entrainer form minimum point azeotropic mixture, steam from tower top, after condensation split-phase, outside aqueous phase to system, organic facies mainly contains entrainer, reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Triethylene diamine aqueous solution feed rate is 1000kg/h, and wherein the mass ratio of water and triethylene diamine is 70:30, and feed pressure is 120kPa.In entrainer normal heptane and ethyl acetate mixture and three water triethylene diamine crystalline hydrates, the mass ratio that mass ratio is 12:1, normal heptane and ethyl acetate of water is 30:70, and azeotropy rectification column operating parameter is as shown in table 7.Logistics composition is as shown in table 8.
Table 7
Azeotropy rectification column | Operating parameter |
Tower top operation pressure/kPa (A) | 70 |
Tower reactor operation pressure/kPa (A) | 90 |
Tower top temperature/DEG C | 68 |
Bottom temperature/DEG C | 170 |
Reflux ratio | 0.62 |
Theoretical cam curve | 42 |
Table 8
Logistics (mass percent) | 7 | 8 |
Water | 99.4 | < 0.1 |
Triethylene diamine | 0 | > 99.9 |
Normal octane, ethyl acetate | 0.6 | 0 |
Flow (kg/h) | 711 | 300.1 |
[embodiment 5]
Triethylene diamine aqueous solution continuously enters azeotropy rectification column, entrainer toluene and n-butyl acetate mixture disposably join azeotropy rectification column tower reactor, water and entrainer form minimum point azeotropic mixture, steam from tower top, after condensation split-phase, outside aqueous phase to system, organic facies mainly contains entrainer, reflux cycle uses, and tower reactor obtains anhydrous triethylene diamine product.Owing to can lose a small amount of entrainer in waste water, according to entrainer loss amount, interval supplements entrainer.
Triethylene diamine aqueous solution feed rate is 1000kg/h, and wherein the mass ratio of water and triethylene diamine is 80:20, and feed pressure is 120kPa.Entrainer toluene and n-butyl acetate mixture are 70:30 with the mass ratio that mass ratio is 3.8:1, toluene and n-butyl acetate of water in three water triethylene diamine crystalline hydrates, and azeotropy rectification column operating parameter is as shown in table 9.Logistics composition is as shown in table 10.
Table 9
Azeotropy rectification column | Operating parameter |
Tower top operation pressure/kPa (A) | 50 |
Tower reactor operation pressure/kPa (A) | 80 |
Tower top temperature/DEG C | 69 |
Bottom temperature/DEG C | 161 |
Reflux ratio | 0.45 |
Theoretical cam curve | 45 |
Table 10
Logistics (mass percent) | 7 | 8 |
Water | 99.9 | < 0.1 |
Triethylene diamine | 0 | > 99.9 |
Isobutyltrimethylmethane., ethyl acetate | 0.1 | 0 |
Flow (kg/h) | 491.2 | 509.4 |
[comparative example 1]
Using raw material same as in Example 5, technological process, entrainer the most therein is only with toluene.Logistics composition as shown in table 11, with embodiment 2 be relatively shown in Table 12.
Table 11
Logistics (mass percent) | 7 | 8 |
Water | 98.9 | 1.3 |
Triethylene diamine | 1.0 | 98.6 |
Toluene | 0.1 | 0.1 |
Flow (kg/h) | 491.0 | 509.4 |
Table 12
Embodiment 5 | Comparative example 1 | |
Entrainer usage amount (kg) | 1780 | 2214 |
Reboiler | 586 | 642 |
Entrainer loss amount (kg/h) | 0.54 | 0.51 |
[comparative example 2]
Using raw material same as in Example 5, technological process, entrainer the most therein is only with n-butyl acetate.Logistics composition as shown in table 13, with embodiment 2 be relatively shown in Table 14.
Table 13
Logistics (mass percent) | 7 | 8 |
Water | 98.24 | 0.3 |
Triethylene diamine | 0.71 | 98.2 |
Sec-butyl acetate | 1.05 | 1.5 |
Flow (kg/h) | 492 | 509.4 |
Table 14
Embodiment 5 | Comparative example 2 | |
Entrainer usage amount (kg) | 1780 | 1218 |
Reboiler | 586 | 542 |
Entrainer loss amount (kg/h) | 0.54 | 2.1 |
Claims (9)
1. a separation method for triethylene diamine, triethylene diamine crystalline hydrate or triethylene diamine water
Solution continuously enters azeotropy rectification column, and entrainer joins azeotropy rectification column tower reactor, water and entrainer and forms azeotropic
Thing steams from tower top, and after condensation split-phase, outside aqueous phase separation to system, organic facies reflux cycle uses, tower
Still obtains anhydrous triethylene diamine product;Wherein, described entrainer is selected from benzene,toluene,xylene, the most pungent
At least one in alkane, isobutyltrimethylmethane. with selected from methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate,
The compositions that at least one in n-butyl acetate is formed.
The separation method of triethylene diamine the most according to claim 1, it is characterised in that described triethylene two
In amine crystalline hydrate or triethylene diamine aqueous solution, water: the mass ratio of triethylene diamine is 1:99~99:
1。
The separation method of triethylene diamine the most according to claim 1, it is characterised in that described azeotropic distillation
The theoretical cam curve of tower is 20~60, and reflux ratio is 0.4~5.
The separation method of triethylene diamine the most according to claim 3, it is characterised in that described azeotropic distillation
The theoretical cam curve of tower is 20~45, and reflux ratio is 0.4~2.
The separation method of triethylene diamine the most according to claim 1, it is characterised in that described azeotropic distillation
The tower top operation pressure of tower is 30~100kPa, and tower top temperature is 40~120 DEG C;Tower reactor operation pressure is 50~130
KPa, bottom temperature is 120~200 DEG C.
The separation method of triethylene diamine the most according to claim 5, it is characterised in that described azeotropic distillation
The tower top operation pressure of tower is 30~90kPa, and tower top temperature is 40~90 DEG C;Tower reactor operation pressure is 50~110
KPa, bottom temperature is 140~180 DEG C.
The separation method of triethylene diamine the most according to claim 1, it is characterised in that in described entrainer
At least one in benzene,toluene,xylene, normal octane, isobutyltrimethylmethane. with selected from methyl acetate, acetic acid second
The mass ratio of at least one in ester, n-propyl acetate, isopropyl acetate, n-butyl acetate is 90:10~10:
90。
The separation method of triethylene diamine the most according to claim 7, it is characterised in that in described entrainer
At least one in benzene,toluene,xylene, normal octane, isobutyltrimethylmethane. with selected from methyl acetate, acetic acid second
The mass ratio of at least one in ester, n-propyl acetate, isopropyl acetate, n-butyl acetate is 90:10~50:
50。
The separation method of triethylene diamine the most according to claim 1, it is characterised in that described entrainer with
The mass ratio of the water in triethylene diamine crystalline hydrate or triethylene diamine aqueous solution is 3:1~15:1.
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CN103012411A (en) * | 2012-11-21 | 2013-04-03 | 西安近代化学研究所 | Method for separating and purifying triethylene diamine by reaction |
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2013
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US4911793A (en) * | 1987-08-05 | 1990-03-27 | Basf Aktiengesellschaft | Distillative isolation of N-ethylpiperazine in the presence of water |
CN102030755A (en) * | 2010-11-24 | 2011-04-27 | 西安近代化学研究所 | Method for preparing high-purity triethylene diamine |
CN102584834A (en) * | 2011-12-20 | 2012-07-18 | 西安近代化学研究所 | Separation method for mixture of triethylene-diamine and ethanolamine |
CN103012411A (en) * | 2012-11-21 | 2013-04-03 | 西安近代化学研究所 | Method for separating and purifying triethylene diamine by reaction |
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