CN105693446B - A kind of isopropanol triethylamine azeotropic mixture extraction rectifying method - Google Patents
A kind of isopropanol triethylamine azeotropic mixture extraction rectifying method Download PDFInfo
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- CN105693446B CN105693446B CN201610026615.0A CN201610026615A CN105693446B CN 105693446 B CN105693446 B CN 105693446B CN 201610026615 A CN201610026615 A CN 201610026615A CN 105693446 B CN105693446 B CN 105693446B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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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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- 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
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive 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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Abstract
A kind of isopropanol triethylamine azeotropic mixture extraction rectifying method, isopropanol of the present invention includes the successional mode of operation of normal pressure or atmosphere intermission mode of operation with triethylamine azeotropic mixture extraction rectifying method, by selecting a variety of extractants, the isopropanol and triethylamine product of high-purity are obtained, and extractant can be recycled.The maximum of the present invention is characterised by extraction except selecting conventional solvent, additionally use the mixed extractant that conventional solvent is constituted with ionic liquid, advantage is huge in terms of energy consumption, environmental pressure, product purity, it is particularly suitable for large-scale industrialization application, in particular for the separation of isopropanol triethylamine azeotropic system, current technology blank has been filled up.
Description
Technical field
Separation method provided by the present invention is directed to isopropanol-triethylamine azeotropic system, and ethylene glycol, 1 is respectively adopted,
The mixed solvent of 2- propane diols, 1,3-BDO, 1,3-PD and ethylene glycol and ionic liquid composition is used as extractant, category
In the extraction rectifying method of isopropanol-triethylamine azeotropic system.
Background technology
The raw material being related in the present invention is isopropanol and triethylamine, both material common in chemical industry.It is different
Propyl alcohol（C3H8O）, also known as dimethylcarbinol is important chemical products and raw material.It is mainly used in pharmacy, cosmetics, plastics, perfume (or spice)
Material, coating etc..Also act as antifreezing agent, cleaning agent, the additive of blended gasoline, the dispersant of pigment production, printing and dyeing industry
Fixative, the antifoggant of glass and transparent plastic, the diluent of adhesive, antifreezing agent, dehydrating agent etc..Triethylamine（C6H15N）, again
Name：N, N- diethyl ethanamine, triethylamine, solvent, catalyst and raw material are can be used as in organic synthesis industry.Triethylamine can use
It is special molten in the catalyst of phosgenation makrolon, the polymerization inhibitor of tetrafluoroethene, thiofide, paint stripper to produce
Agent, enamel anti-hardening agent, acid binding agent, surfactant, preservative, bactericide, ion exchange resin, dyestuff, spices, medicine,
High-energy fuel and liquid rocket propellant etc..
Isopropanol not only has important application with triethylamine in petrochemical industry, and also has inside other industry
Quite widely use.But there is azeotropism in two kinds of materials so that the difficulty for separating both is greatly increased.For organic
The recovery of solvent, it is industrial it is widely used be distillation or rectifying processing mode, but for azeotropic system, the country is used
More is azeotropic distillation method.But azeotropic distillation has the limitation of its own：In terms of energy consumption, cost is compared with other method more
Height, in equipment investment, also tends to bigger compared with other method, and product purity is difficult to ensure that.
In the separation method that chemical industry is commonly used, rectifying turns into the selection of numerous enterprises with the advantage of its own, still
Rectifying, which is meant that, needs energy consumption, therefore energy consumption cost also needs the problem of emphasis considers as enterprise.With reference to country " 13
Five " planning and presently relevant industrial policy, energy-conservation, emission reduction turn into the most important thing of the chemical enterprise coming years.Adopted in the present invention
With extraction rectification technique, compared with traditional azeotropic distillation, significantly improved on energy consumption problem, and product purity is higher.This
The extractant used in invention, is no longer simple organic solvent, but the mixing that selection organic solvent is constituted with ionic liquid
Extractant, can substantially reduce the loss of extractant.
Ionic liquid refers to the salt compounds being in a liquid state at room temperature being made up of organic cation and anion, has
Steam is forced down, fusing point is low, liquid journey is wide, easy to operate, soluble good and the advantages of stablize high, although ionic liquid has numerous excellent
Point, but be due to that existing market is expensive, and the large usage quantity of extractant, cause production cost very high, therefore utilization rate
It is relatively low.It was discovered by researchers that ionic liquid can constitute new ionic liquid with complexant, industrial applications can be effectively reduced
Cost, and have both advantages concurrently simultaneously, conventional complexant has ethylene glycol, glycerine etc., and the complexant that the present invention is selected is
Ethylene glycol, mixed solvent is constituted with ionic liquid.
The mixed liquor conduct of conventional organic solvents and ionic liquid can be used in advantage based on ionic liquid, rectification process
Extractant, can effectively reduce the loss of conventional solvent（Ionic liquid is non-volatile, loss late is extremely low, and recycles）, drop
Low production cost, while product quality can be improved.
Existing azeotropic system separation means are divided into two classes substantially：Azeotropic distillation and extracting rectifying.Extracting rectifying is in product
There is advantage compared with azeotropic distillation in terms of purity, energy consumption.And at present in the selection of extractant, substantially using conventional solvent conduct
Extractant directly uses ion liquid abstraction agent in other words, and a kind of continuous extractions of CN103193590A separate the side of mixed alcohol-water
A kind of technique of separation of extractive distillation Ethyl formate-alcohol-water of method, CN102627556A makees extractant using ethylene glycol；
The method of CN103193590A ion liquid abstractions rectifying separation Acetic Acid-Water uses ionic liquid as extractant.The former is in extraction
Take low in efficiency, and the latter is then much bigger in cost of investment.Sum it up, how to reduce loss of extractant and be produced into
Originally the problem of product purity is current rectification process urgent need to resolve, is improved.
At present, the separation on isopropanol-triethylamine azeotropic system, does not have related document and delivers or report.
The content of the invention
It is not enough present in existing process the invention aims to overcome, and for isopropanol-triethylamine azeotropic body
System, proposes that a kind of good separating effect, product purity height, energy consumption are low, and extractant easily reclaims, is easy to industrialized separation method.
Pass through T-x-y phasors, it can be seen that isopropanol-triethylamine has azeotropism（It can be seen that isopropanol-triethylamine in accompanying drawing 1
There is azeotropic point）.
In order to solve the above technical problems, the technical solution adopted by the present invention is：A kind of isopropanol-triethylamine azeotropic mixture
Extraction rectifying method, this method is operated or intermittent operation using continuity.
Extractant described in the invention is respectively ethylene glycol, 1,3- propane diols, 1,2- propane diols, 1,3 butylene glycol, second
Glycol and ionic liquid（40wt%~50wt%）Mixed extractant is formed, product purity and extraction efficiency can be effectively improved, is reduced
Production cost.The ionic liquid that invention is used is respectively N- ethylpyridine dimethyl phosphate salt（[epy][DMP]）, N- methyl pyrroles
Pyridine dimethyl phosphate salt（[mpy][DMP]）, N- butyl-pyridinium dimethyl phosphate salt（[bpy][DMP]）.
A kind of isopropanol of the present invention-triethylamine azeotropic mixture extraction rectifying method continuity operating procedure is such as
Under：
1）Isopropanol is continuously added to triethylamine mixture by T101 middle and lower parts by feed system, and extractant is from tower top
Add, feeding temperature is all normal temperature, T101 operating pressures are normal pressure；
2）T101 tower tops can obtain the isopropanol product of product purity more than 99.9%, and bottom of towe is triethylamine and extractant；
3）T101 tower base streams enter T102 middle part, and the triethylamine product of purity more than 99.9% is obtained in T102 tower tops,
Bottom of towe residue extractant and micro triethylamine and isopropanol, T102 operating pressures are normal pressure；
4）T102 tower base streams are incorporated to extractant feed pipeline, are supplemented as extractant.
Based on above-mentioned a kind of isopropanol-operation of triethylamine azeotropic mixture extraction rectifying method continuity, the continuity
Operation important technological parameters be：
1）T101 technical parameters：Theoretical cam curve=30 ~ 45；Reflux ratio=0.5:1~4:1, operating pressure=normal pressure；Extractant
With charge ratio=1.2 of raw material:1~6:1, feeding temperature=30 DEG C ~ 40 DEG C, pressure=0.11MPa, raw material is isopropanol（53wt%）
With triethylamine（47wt%）Nearly azeotropic composition, feeding temperature=30 DEG C ~ 40 DEG C, pressure=0.11MPa；Extracted feed position is 3 ~ 9
Block column plate, 27 ~ 37 blocks of feedstock position column plate；
2）T102 technical parameters：Theoretical cam curve=20 ~ 50；Reflux ratio=0.8:1~3:1, operating pressure=normal pressure；Feed position
It is set to 12 ~ 30 blocks of column plates.
A kind of isopropanol of the present invention-triethylamine azeotropic mixture extraction rectifying method intermittent operation step is such as
Under：
1）Isopropanol disposably squeezes into tower bottom of rectifying tower E1 with triethylamine mixture by raw material pump P2, opens heating；
2）When condensate liquid, total reflux operation occurs in tower top, and extractant is continuously added in tower by pump P1, and continues complete
Reflux operation；
3）When tower top temperature reaches 82 DEG C, detection, tower top isopropanol content is more than 99%, with reflux ratio（0.5~4）:1 extraction
Isopropanol product is to V3（With the rise of tower top temperature, reflux ratio is accordingly improved to 4:1）；
4）When tower top temperature is more than 85 DEG C, and detects isopropanol content and start reduction, close extraction, carry out infinite reflux behaviour
Make 0.5h, start afterwards with reflux ratio（2~4）:1 extraction isopropanol-triethylamine changeover portion to V2（With the rise of tower top temperature,
Reflux ratio is accordingly improved to 4:1）；
5）When tower top temperature reaches 88 DEG C, detection, tower top triethylamine content is more than 99%, with reflux ratio（0.8~3）:1 extraction
Triethylamine product is to V5（With the rise of tower top temperature, reflux ratio is accordingly improved to 3:1）；
6）When tower top temperature is more than 91 DEG C, and detects triethylamine content and start reduction, stop adding extractant and simultaneously close
Extraction, infinite reflux 0.2h, start afterwards with（2~4）:1 extraction triethylamine-extractant changeover portion to V4；
7）When tower top temperature is more than 120 DEG C, stops heating, after the cooling of tower reactor extractant, be discarded to V1 standby.
Based on above-mentioned a kind of isopropanol-triethylamine azeotropic mixture extraction rectifying method intermittent operation step, the operation
The main important technological parameters of step are
1）Extractive distillation column theoretical cam curve N=30 ~ 50；Full tower operating pressure is normal pressure；
2）The charge ratio R of extractant and raw material=(2 ~ 6):1.
Beneficial effects of the present invention：The present invention can make isopropanol-triethylamine azeotropism disappear by adding extractant
（Azeotropic point disappears in accompanying drawing 2）.
The novelty of the present invention is with advantage：
1）The separation of isopropanol and triethylamine azeotropic system, there is no separating technology to report or deliver at present；
3）Using a variety of extractants, selectivity is various；
3）Ionic liquid is being with the addition of in extractant, it is possible to increase the service efficiency of extractant, reduce cost；
4）Technique is simple, using double tower continuous rectification mode（T101 towers are extractive distillation column, and T102 towers are solvent recovery
Tower）Or single column batch fractionating mode, it can be selected according to product yield requirement, operation is flexible, while effectively reducing cost.
Brief description of the drawings
Fig. 1 is isopropanol-triethylamine T-x-y phasors.
Fig. 2 is the T-x-y phasors after isopropanol-triethylamine addition extractant.
Fig. 3 is continuity operation device of the present invention and flow chart.
Fig. 4 is intermittent operation device of the present invention and flow chart.
1.-extractant enters tower stream stock；2.-raw material enters tower stream stock；3. stock is flowed in extractive distillation column backflow；4.-extracting rectifying
Tower extraction stream stock；5.-solvent recovery tower enters stream stock；6.-solvent recovery tower backflow stream stock；7.-solvent recovery tower extraction stream
Stock；8.-extractant extraction stream stock.
Fig. 3 capital equipment explanations：T101-extractive distillation column；T102-solvent recovery tower；E101, E103-condenser；
E102, E103-reboiler；P101-material pump.
Fig. 4 symbol descriptions：P1-extractant feed pump；P2-feedstock pump；E1-tower reactor；E2-condenser（Containing catching
Storage）；V1 ~ V5 be respectively extractant recycling can, interim fraction tank 1., products pot 1., interim fraction tank 2., products pot 2..
Embodiment
It is that the invention will be further described for combination specific implementation case below, but does not limit the scope of protection of the invention.
Embodiment one
The implementation case is continuous extraction distillation operation mode, as shown in Figure 3, and extractant selects ethylene glycol and N- ethyls
Pyridine dimethyl phosphate salt（[epy][DMP]）, consumption is 500kg/h；Feed throughput is 100kg/h, and raw material composition is isopropyl
Alcohol（53wt%）With triethylamine（47wt%）.The T101 numbers of plates are 40, and extractant feed position is in the 5th block of column plate, feedstock position
Put in 32 blocks of column plates.Reflux ratio is set as 4:1, overhead extraction speed is 53kg/h, and obtained isopropanol purity is 99.9%.
The T102 numbers of plates are 30, and 5. feed entrance point is the 20th block of column plate to stream stock, and reflux ratio is 2:1, overhead extraction speed is 47kg/h, is obtained
The triethylamine purity arrived is 99.9%, the backflow of bottom of towe extractant, is used as the supplement of solvent.
Embodiment two
Extractant selects ethylene glycol, and consumption is 600kg/hr, and T101 reflux ratio is set into 3:1, T102 reflux ratio is set
For 1:1, other conditions such as embodiment one, obtained isopropanol is with triethylamine product purity more than 99.9%.
Embodiment three
Extractant selects 1,2-PD, other conditions such as embodiment one, and obtained isopropanol is with triethylamine product purity
More than 99.9%.
Example IV
The implementation case is batch extracting rectified mode of operation, as shown in Figure 4, and extractant selects ethylene glycol and N- methyl
Pyridine dimethyl phosphate salt（[mpy][DMP]）, consumption is 500kg；Feed throughput is 100kg, and raw material composition is isopropanol
（53wt%）With triethylamine（47wt%）.Theoretical cam curve is 40, and extractant feed position is in the 5th block of column plate.Isopropanol and three second
Amine blends disposably squeeze into tower bottom of rectifying tower E1 by raw material pump P2, open heating；When condensate liquid, infinite reflux behaviour occurs in tower top
Make, and extractant is continuously added in tower by pump P1, and continue total reflux operation；When tower top temperature reaches 82 DEG C, detection, tower
Push up isopropanol content and be more than 99%, with reflux ratio（0.5~4）:1 produces isopropanol product to V3（With the rise of tower top temperature, return
Stream is improved to 4 than corresponding:1）；When tower top temperature is more than 85 DEG C, and detects isopropanol content and start reduction, close extraction, enter
Row total reflux operation 0.5h, starts with reflux ratio afterwards（2~4）:1 extraction isopropanol-triethylamine changeover portion to V2（With tower top
The rise of temperature, reflux ratio is accordingly improved to 4:1）；When tower top temperature reaches 88 DEG C, detection, tower top triethylamine content is more than
99%, with reflux ratio（0.8~3）:1 produces triethylamine product to V5（With the rise of tower top temperature, reflux ratio is accordingly improved to 3:
1）；When tower top temperature is more than 91 DEG C, and detects triethylamine content and start reduction, stop adding extractant and simultaneously close extraction, entirely
Flow back 0.2h, start afterwards with（2~4）:1 extraction triethylamine-extractant changeover portion to V4；When tower top temperature is more than 120 DEG C, stop
Only heat, after the cooling of tower reactor extractant, be discarded to V1 standby.
Embodiment five
Extractant selects 1,3-BDO, and consumption is 400kg, other conditions such as example IV, and obtained isopropanol is with three
Ethamine product purity is more than 99%.
Embodiment six
Extractant selects 1,3-PD, other conditions such as example IV, and obtained isopropanol is with triethylamine product purity
More than 99%.
Described above is effect preferably case in the present invention, but the content is only presently preferred embodiments of the present invention, no
The practical range for being defined the present invention can be used for.
Claims (4)
1. a kind of isopropanol-triethylamine azeotropic mixture extraction rectifying method, it is characterised in that：This method is divided into continuity operation
Or intermittent operation, wherein continuity, which is operated, includes extractive distillation column (T101) and solvent recovery tower (T102), raw material isopropanol
Added with the mixture of triethylamine in extractive distillation column (T101) middle and lower part, extractant adds from extractive distillation column (T101) top
Enter, isopropanol is in extractive distillation column (T101) overhead extraction, and extractant is with triethylamine mixture by extractive distillation column (T101) tower
Enter after the extraction of bottom in the middle part of solvent recovery tower (T102), triethylamine is from solvent recovery tower (T102) overhead extraction, bottom of towe extractant
Posterior circle is produced to utilize；Intermittent operation includes isopropanol and disposably squeezes into tower bottom of rectifying tower E1 with triethylamine mixture material,
Extractant is continuously added to by tower top, first overhead extraction for isopropanol, it is different according to temperature afterwards, isopropyl is produced successively
Alcohol-triethylamine interim fraction, triethylamine, triethylamine-extractant interim fraction, tower reactor extraction extractant are recycled；
Continuity or interval row operate extractant to be ethylene glycol or 1,2- propane diols or 1,3 butylene glycol or 1,3- propane diols or second
The mixed extractant that glycol is constituted with ionic liquid；
Mixed extractant intermediate ion liquid be respectively N- picoline dimethyl phosphates salt, N- ethylpyridine dimethyl phosphates salt,
N- butyl-pyridinium dimethyl phosphate salt.
2. the method as described in claim 1, it is characterised in that：In the mixed extractant that ethylene glycol is constituted with ionic liquid, from
Sub- liquid mass fraction is 40wt%~50wt%.
3. the method as described in claim 1, it is characterised in that：Under continuity mode of operation, important technological parameters are：
1) extractive distillation column (T101) technical parameter：Theoretical cam curve is 30~45；Reflux ratio is 0.5:1~4:1, full tower operation
Pressure is normal pressure；The charge ratio 1.2 of extractant and raw material:1~6:1, feeding temperature is 30 DEG C~40 DEG C, pressure 0.11MPa；It is former
Expect for isopropanol and triethylamine, 30 DEG C~40 DEG C of feeding temperature, pressure 0.11MPa；Extracted feed position is 3~9 blocks of column plates, former
Expect 27~37 blocks of column plates of feed entrance point；
2) solvent recovery tower (T102) technical parameter：Theoretical cam curve is 20~50；Reflux ratio 0.8:1~3:1, full tower operation pressure
Power is normal pressure；Feed entrance point is 12~30 blocks of column plates.
4. the method as described in claim 1, it is characterised in that：Under intermittent operation mode, important technological parameters are：Extraction essence
It is 20~50 to evaporate tower theoretical cam curve；The charge ratio of extractant and raw material is 0.8:1~3:1；Full tower operating pressure is normal pressure.
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| CN106220532B (en) * | 2016-07-21 | 2018-06-22 | 青岛科技大学 | A kind of method of separation of extractive distillation acetonitrile and triethylamine |
| CN107021873A (en) * | 2017-05-05 | 2017-08-08 | 安庆市鑫祥瑞环保科技有限公司 | A kind of method that n-butanol is extracted from the mixture of n-butanol, triethylamine and water |
| CN106977409B (en) * | 2017-05-09 | 2019-06-25 | 浙江台州市联创环保科技有限公司 | A kind of separation method of triethylamine and water |
| CN107488103B (en) * | 2017-08-24 | 2020-06-05 | 王婵 | Extraction and rectification method for water-isopropanol azeotropic mixture |
| CN108658785B (en) * | 2017-09-08 | 2019-04-16 | 杭州九清科技有限公司 | The separation method of difficult separation system containing triethylamine |
| CN111495150A (en) * | 2020-04-20 | 2020-08-07 | 扬州天启新材料股份有限公司 | Organic waste gas recovery treatment process in industrial cyanate resin production |
| CN113461570B (en) * | 2021-06-24 | 2023-02-17 | 索闻特环保科技(上海)有限公司 | Method for treating mixed liquid containing isopropanol, acetonitrile, triethylamine and water |
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