CN103772329B - Method for simultaneous extraction and recovery of furfural and acetic acid from furfural stripping steam condensate - Google Patents
Method for simultaneous extraction and recovery of furfural and acetic acid from furfural stripping steam condensate Download PDFInfo
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- CN103772329B CN103772329B CN201210408427.6A CN201210408427A CN103772329B CN 103772329 B CN103772329 B CN 103772329B CN 201210408427 A CN201210408427 A CN 201210408427A CN 103772329 B CN103772329 B CN 103772329B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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Abstract
The invention relates to a method for recovery of furfural and acetic acid from a furfural stripping steam condensate, and the method is as follows: (1) countercurrent contact of the furfural stripping steam condensate and an extractant is performed in an extraction tower to obtain an extraction phase containing the extractant, the furfural and the acetic acid at the tower top, an extraction residue phase in a tower kettle is water containing trace of the furfural and the acetic acid; (2) the extraction phase enters into an extractant regeneration tower for separation to obtain the furfural and the acetic acid containing trace of the water at the tower top, the extractant is in the tower kettle, the extractant returns back to the extraction tower after cooling; (3) the furfural and the acetic acid containing trace of the water enter into a furfural refining tower for separation to obtain the furfural in the tower kettle and obtain the acetic acid containing the water at the tower top; (4) the acetic acid containing the water enters into an azeotropic distillation column for separation, a water and entrainer mixture is in a tower top phase splitter, the water is collected from the tower top, an entrainer returns back into the tower, and the acetic acid is in the tower kettle. The method can simultaneously recover the furfural and the acetic acid, the recovery rate is higher than 90%, the purity of products is higher than 99%, the extraction efficiency is high, and the unit energy consumption is less.
Description
Technical field
The invention belongs to Chemicals technical field of purification, particularly a kind of method simultaneously reclaiming furfural and acetic acid from furfural stripped vapor phlegma.
Background technology
Furfural has another name called furtural, is a kind of important heterocyclic organic compound.Be that the Chemicals that raw material directly or indirectly derives reach kind more than 1600 with furfural, be widely used in the industries such as medicine, agricultural chemicals, resin, daily use chemicals, casting, weaving, oil.Up to now, furfural can only be that raw material obtains with vegetable fibre, mainly corn cob, bagasse etc., is also several bio-based platform chemicals taking lignocellulose-like biomass as raw material large-scale commercial and produce few in number at present simultaneously.
Current furfural production state is mainly in developing countries such as China, Brazil, Dominica, Iran, and the developed country such as American-European, Japanese stopped furfural production substantially.Enter 21 century, skyrocketing along with oil price, the demand of furfural constantly increases, and the market value of current furfural has exceeded 10000 yuan/ton.Current, China's furfural production ability, more than 200,000 tons/year, is the country that furfural output is maximum in the world, is also maximum furfural export State in the world, mainly sells to the developed countries and regions such as America and Europe, Japan, Korea S.
Traditional furfural production is rich in the straw of hemicellulose for raw material (such as corn cob, bagasse etc.), first half fiber under the effect of sulfuric acid catalyst in lignocellulose is hydrolyzed and mainly generates pentose, and pentose generates furfural through dehydration cyclization again.Because furfural especially easily side reaction occurs under its reaction conditions, the industrial mode often through passing into water vapor continuously in reactor takes reaction system out of to improve furaldehyde yield the furfural that reaction generates.Under the condition that furfural generates; ethanoyl on hemicellulose molecule side chain is also easily oxidized to come off thus generates acetic acid; therefore the stripped vapor passing into reactor can take reaction system out of furfural and byproduct acetic acid simultaneously, that is both also contains acetic acid containing furfural in furfural stripped vapor phlegma.
In furfural stripped vapor phlegma, furfural content is about 5wt% ~ 8wt%, and acetate concentration is about 1wt% ~ 2wt %.Because furfural and water form azeotrope, in order to obtain finished product furfural, current industrial employing five tower process for refining extracts furfural product from furfural stripped vapor phlegma, and acetic acid remains in the furfural waste-water being formed in water and be rich in acetic acid.Due to organism such as the furfurals containing acetic acid and trace in furfural waste-water, COD value is up to more than 35000, if directly discharge, environmental pollution is serious, is also the waste of resource simultaneously.Recent year scholar successfully develops the technology adopting extraction process to reclaim acetic acid in furfural waste-water, both having reclaimed acetic acid and has created economic benefit, and made again the COD value of waste water decline to a great extent, and having created condition for processing furfural waste-water further.
In recent years, along with the further investigation to liquid-liquid extraction techniques, find that adopting liquid-liquid extraction method from furfural aqueous solution, extract energy consumption needed for furfural wants significantly lower than traditional five tower process for refining, the method is considered to a kind of has the furfural of industrial prospect to extract new technology most.But prior art when reclaiming furfural and acetic acid from furfural stripped vapor phlegma, need first to extract furfural, then extract acetic acid in furfural waste-water, there is separation efficiency lower, energy consumption is higher, the problem of complex process.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of method simultaneously reclaiming furfural and acetic acid from furfural stripped vapor phlegma, comprise the steps:
(1) furfural stripped vapor phlegma and extraction agent counter current contact in extraction tower, tower top obtains the extraction phase containing extraction agent, furfural and acetic acid, and the extracting phase that tower reactor obtains is the water containing micro-furfural and acetic acid;
(2) extraction phase in step (1) enters extractant regeneration tower and is separated, and tower top obtains furfural containing minor amount of water and acetic acid, and tower reactor is extracted agent, returns extraction tower after extraction agent cooling;
(3) furfural containing minor amount of water obtained in step (2) enters furfural treatment tower with acetic acid and is separated, and tower reactor obtains furfural, and its purity is greater than 99wt%, and tower top obtains water-containing acetic acid;
(4) the middle water-containing acetic acid of step (3) enters after azeotropy rectification column contacts with entrainer and is separated, and tower top phase splitter obtains water and entrainer mixture, and water is from overhead extraction, and entrainer returns in tower, and tower reactor obtains acetic acid, and its purity is greater than 99wt%.
In the inventive method, in step (1), extraction tower extraction agent used is composite extractant, described extraction agent is the tertiary amine of 12 ~ 16 carbon atoms, carbon number is greater than the alphanol (boiling point is higher than 180 DEG C) of 7 and the composition containing nitro-aromatic derivative, wherein, tertiary amine accounts for 10wt% ~ 60wt%, alphanol accounts for 10wt% ~ 30wt%, accounts for 10wt% ~ 60wt% containing nitro-aromatic derivative.Preferably, tertiary amine accounts for 20wt% ~ 40wt%, and alphanol accounts for 10wt% ~ 30wt%, accounts for 20wt% ~ 40wt% containing nitro-aromatic derivative.
In the inventive method, described can be specifically one or more in 2-meta-xylene, 3-meta-xylene, o-Nitrophenyl methyl ether, Ortho Nitro Toluene containing nitro-aromatic derivative.
In the inventive method, extraction tower used is Pulsed Packed Extraction Column, wherein inner-tower filling material height is equivalent to 5 ~ 20 blocks of theoretical trays, the operational condition of extraction tower is: extraction agent and furfural stripped vapor phlegma input material volume ratio are 3 ~ 6:1, extraction temperature is 30 ~ 50 DEG C, pressure is normal pressure, and pulse-repetition is 0.01 ~ 10s
-1, pulsating pressure is 100 ~ 500kPa.
In the inventive method, extractant regeneration tower is packing tower, and wherein inner-tower filling material height is equivalent to 5 ~ 30 blocks of theoretical trays, and working pressure is 5 ~ 90 kPa, and reflux ratio is 1 ~ 5, tower top temperature 60 ~ 100 DEG C, bottom temperature 140 ~ 220 DEG C.In the extraction agent of regeneration, furfural and acetate concentration sum are less than 0.05%.
In the inventive method, furfural treatment tower is packing tower, and wherein inner-tower filling material height is equivalent to 5 ~ 30 blocks of theoretical trays, and working pressure is 5 ~ 90 kPa, and reflux ratio is 1 ~ 5, tower top temperature 60 ~ 90 DEG C, bottom temperature 100 ~ 140 DEG C.Furfural product purity at the bottom of tower is greater than 99% (wt), tower top to be concentration be more than 80% thick acetic acid.
In the inventive method, described azeotropy rectification column is tray column, and wherein in tower, stage number is equivalent to 5 ~ 20 blocks of theoretical trays, atmospheric operation, and reflux ratio is 1 ~ 3, tower top temperature 60 ~ 110 DEG C, bottom temperature 105 ~ 130 DEG C.Entrainer and feedstock weight ratio are 0.1 ~ 2.Azeotropy rectification column entrainer used is the one in hexanaphthene, vinyl acetic monomer, Iso Butyl Acetate, n-butyl acetate.
The inventive method tool has the following advantages:
(1) in the inventive method, have employed high boiling double solvents as extraction agent, wherein, to furfural, there is very high selectivity containing nitro-aromatic derivative itself, but also the effect regulating whole extractant composition system viscosity can be played, the selectivity of extraction agent Dichlorodiphenyl Acetate can be improved further; Alphanol can promote the selectivity that can promote again tertiary amine Dichlorodiphenyl Acetate containing nitro-aromatic derivative to the selectivity of furfural, this extraction agent all has very high selectivity to furfural and acetic acid, furfural and acetic acid can be reclaimed through single extraction operation simultaneously, the furfural rate of recovery is greater than 92%, recovery rate is greater than 95%, and extracting phase can be used as oiler feed and also can directly discharge after simple process again.
(2) the inventive method, have employed the high boiling nitro-aromatic derivative that contains as extraction agent, extraction agent boiling point is higher than furfural boiling point, in furfural and extraction agent sepn process, the energy consumption of sepn process can be reduced, and it is high to be separated the furfural product purity obtained, and furfural waste-water intractability is reduced greatly, the efficiency extracting furfural and acetic acid from furfural stripped vapor phlegma is improved greatly.
(3) in the inventive method, described extraction agent wide material sources, pollution-free, technological process is simple, and product purity is high, and furfural and acetate products purity all can reach more than 99%;
Accompanying drawing explanation
Fig. 1 is present invention process schematic flow sheet.
Embodiment
Composition graphs 1, the inventive method technical process is further illustrated, furfural stripped vapor phlegma 2 and extraction agent 7 enter Pulsed Packed Extraction Column 1 respectively at the bottom of tower top and tower, pulse of air 3 is had to blast at the bottom of tower, furfural stripped vapor phlegma 2 and extraction agent 3 counter current contact in Pulsed Packed Extraction Column 1, after extracting and separating, extracting phase 4 and extraction phase 5 is obtained respectively at tower top and tower reactor, described extracting phase 4 can do oiler feed or directly discharge after simple process, extraction phase 5 enters extractant regeneration tower 6 and carries out regeneration separation, furfural containing minor amount of water and acetic acid 9 is obtained at tower top, tower reactor is extracted agent 7, extraction agent 7 returns Pulsed Packed Extraction Column 1 after water cooler 8 cools, furfural containing minor amount of water and acetic acid 9 enter furfural treatment tower 10 and are separated, tower reactor obtains furfural 11, tower top obtains water-containing acetic acid 12, water-containing acetic acid 12 enters azeotropy rectification column 13, and disposablely in tower adds entrainer, and overhead vapours 14 enters phase splitter 15 after condensation, and after being separated in phase splitter, aqueous phase 17 extraction, oil phase entrainer 16 returns azeotropy rectification column 13, and tower reactor obtains pure acetic acid 18.
Below by specific embodiment, the invention will be further described, but the scope of the invention is not limited to scope described in embodiment.
Embodiment 1:
In furfural stripped vapor phlegma, furfural content and acetate concentration are respectively 5.6% (wt) and 1.2% (wt).
Extraction agent is trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mixed solvent, and wherein, trialkyl tertiary amine accounts for 40wt%, and n-Octanol accounts for 20wt%, and Ortho Nitro Toluene accounts for 40wt%.
The in-built silk filling corrugated wire gauze packing of Pulsed Packed Extraction Column, virtual height 5 meters, is equivalent to 10 blocks of theoretical trays, and extraction agent and furfural stripped vapor phlegma charge ratio are 3:1, and extraction temperature 31 DEG C, pulse-repetition is 2s
-1, after stable operation, the temperature of extraction phase and extracting phase is respectively 36 DEG C and 40 DEG C.
The in-built silk filling corrugated wire gauze packing of extractant regeneration tower, virtual height 4 meters, is equivalent to 28 blocks of theoretical trays, feed entrance point is being equivalent to the 10th piece of column plate place, and reflux ratio is 2, and working pressure is 10 Kpa, after stable operation, the temperature of tower top and tower reactor is respectively 81 DEG C and 147 DEG C.
The in-built silk filling corrugated wire gauze packing of furfural treatment tower tower, virtual height 4 meters, is equivalent to 28 blocks of theoretical trays, and feed entrance point is at the 15th block of column plate, and reflux ratio is 2, and working pressure is 30Kpa, and after stable operation, the temperature of tower top and tower reactor is respectively 71 DEG C and 123 DEG C.
Be equivalent to 20 blocks of theoretical trays in azeotropy rectification column tower, feed entrance point is at the 10th block of column plate, and atmospheric operation, entrainer and charge-mass ratio are 2, and phase splitter temperature is 35 DEG C, after stable operation, and the temperature of tower top and tower reactor is respectively 99 DEG C and 118 DEG C.Specific experiment the results are shown in Table 1.
Embodiment 2:
Substantially the same manner as Example 1, but extraction agent and furfural stripped vapor phlegma charge ratio are 5:1.
Embodiment 3:
Substantially the same manner as Example 1, but extraction agent and furfural stripped vapor phlegma charge ratio are 6:1.
Embodiment 4:
Substantially the same manner as Example 1, but composite extractant composition becomes: trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mass ratio 3:1:1.
Embodiment 5:
Substantially the same manner as Example 1, but composite extractant composition becomes: trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mass ratio 1:1:3.
Embodiment 6:
Substantially the same manner as Example 1, but composite extractant composition becomes: trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mass ratio 1:0:1.
Embodiment 7:
Substantially the same manner as Example 1, but composite extractant composition becomes: trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mass ratio 0:1:1.
Embodiment 8:
Substantially the same manner as Example 1, but composite extractant composition becomes: trialkyl tertiary amine, n-Octanol, Ortho Nitro Toluene mass ratio 1:1:0.
Embodiment 9:
Substantially the same manner as Example 1, but extraction tower service temperature becomes 45 DEG C.
Embodiment 10:
Substantially the same manner as Example 1, but extraction tower service temperature becomes 55 DEG C.
Embodiment 11:
Substantially the same manner as Example 1, but extraction tower pulse-repetition becomes 1s
-1.
Embodiment 12:
Substantially the same manner as Example 1, but extraction tower pulse-repetition becomes 3s
-1.
Embodiment 13:
Substantially the same manner as Example 1, but extraction agent becomes 2-meta-xylene.
Embodiment 14:
Substantially the same manner as Example 1, but extraction agent becomes 3-meta-xylene.
Embodiment 15:
Substantially the same manner as Example 1, but extraction agent becomes o-Nitrophenyl methyl ether.
Table 1 embodiment result
| Embodiment | The furfural rate of recovery, % | Furfural purity, % | Recovery rate, % | Acetic acid purity, % |
| 1 | 88.0 | 99.3 | 90.1 | 99.5 |
| 2 | 91.0 | 99.5 | 93.3 | 99.3 |
| 3 | 92.5 | 99.6 | 95.5 | 99.6 |
| 4 | 83.5 | 99.6 | 96.5 | 99.6 |
| 5 | 93.5 | 99.6 | 86.5 | 99.6 |
| 6 | 86.0 | 99.0 | 83.4 | 99.2 |
| 7 | 82.1 | 99.1 | 45.9 | 99.5 |
| 8 | 69.3 | 99.5 | 80.0 | 99.6 |
| 9 | 83.9 | 99.2 | 81.6 | 99.3 |
| 10 | 79.5 | 99.3 | 75.5 | 99.2 |
| 11 | 84.8 | 99.2 | 85.2 | 99.4 |
| 12 | 90.1 | 99.4 | 91.0 | 99.5 |
| 13 | 86.5 | 99.4 | 90.2 | 99.5 |
| 14 | 87.5 | 99.3 | 90.7 | 99.6 |
| 15 | 90.1 | 99.5 | 91.2 | 99.6 |
Claims (8)
1. from furfural stripped vapor phlegma, reclaim a method for furfural and acetic acid simultaneously, comprise the steps:
(1) furfural stripped vapor phlegma and extraction agent counter current contact in extraction tower, tower top obtains the extraction phase containing extraction agent, furfural and acetic acid, and the extracting phase that tower reactor obtains is the water containing micro-furfural and acetic acid;
(2) extraction phase in step (1) enters extractant regeneration tower and is separated, and tower top obtains furfural containing minor amount of water and acetic acid, and tower reactor is extracted agent, returns extraction tower after extraction agent cooling;
(3) furfural containing minor amount of water obtained in step (2) enters furfural treatment tower with acetic acid and is separated, and tower reactor obtains furfural, and its purity is greater than 99wt%, and tower top obtains water-containing acetic acid;
(4) the middle water-containing acetic acid of step (3) enters after azeotropy rectification column contacts with entrainer and is separated, and tower top phase splitter obtains water and entrainer mixture, and water is from overhead extraction, and entrainer returns in tower, and tower reactor obtains acetic acid, and its purity is greater than 99wt%;
Wherein, extraction tower extraction agent used is composite extractant, comprise the tertiary amine of 12 ~ 16 carbon atoms, carbon number be greater than 7 alphanol and containing nitro-aromatic derivative, described is one or more in 2-meta-xylene, 3-meta-xylene, o-Nitrophenyl methyl ether, Ortho Nitro Toluene containing nitro-aromatic derivative.
2. in accordance with the method for claim 1, it is characterized in that: in described extraction agent, tertiary amine accounts for 10 ~ 60wt%, and alphanol accounts for 10 ~ 30wt%, account for 10 ~ 60wt% containing nitro-aromatic derivative.
3. in accordance with the method for claim 1, it is characterized in that: in described extraction agent, tertiary amine accounts for 20 ~ 40wt%, and alphanol accounts for 10 ~ 30wt%, account for 20 ~ 40wt% containing nitro-aromatic derivative.
4. in accordance with the method for claim 1, it is characterized in that: extraction tower is Pulsed Packed Extraction Column, wherein inner-tower filling material height is equivalent to 5 ~ 20 blocks of theoretical trays, the operational condition of extraction tower is: extraction temperature is 30 ~ 50 DEG C, pressure is normal pressure, extraction agent and furfural stripped vapor phlegma input material volume ratio are 3 ~ 6:1, and pulse-repetition is 0.01 ~ 10s
-1, pulsating pressure is 100 ~ 500kPa.
5. in accordance with the method for claim 1, it is characterized in that: extractant regeneration tower is packing tower, wherein inner-tower filling material height is equivalent to 5 ~ 30 blocks of theoretical trays, working pressure is 5 ~ 90 kPa, reflux ratio is 1 ~ 5, tower top temperature 60 ~ 100 DEG C, bottom temperature 140 ~ 220 DEG C.
6. in accordance with the method for claim 1, it is characterized in that: furfural treatment tower is packing tower, wherein inner-tower filling material height is equivalent to 5 ~ 30 blocks of theoretical trays, working pressure is 5 ~ 90 kPa, reflux ratio is 1 ~ 5, tower top temperature 60 ~ 90 DEG C, bottom temperature 100 ~ 140 DEG C.
7. in accordance with the method for claim 1, it is characterized in that: in azeotropy rectification column tower, stage number is 5 ~ 20 pieces, atmospheric operation, reflux ratio is 1 ~ 3, entrainer and feedstock weight ratio are 0.1 ~ 2, tower top temperature 60 ~ 110 DEG C, bottom temperature 105 ~ 130 DEG C.
8. in accordance with the method for claim 1, it is characterized in that: entrainer is hexanaphthene, vinyl acetic monomer, Iso Butyl Acetate or n-butyl acetate.
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| CN104771924B (en) * | 2015-04-15 | 2016-06-08 | 中国科学院广州能源研究所 | A kind of devices and methods therefor of furfural preparation coupling ethanol rectification |
| EP3645498B1 (en) | 2017-06-29 | 2021-08-04 | Nouryon Chemicals International B.V. | Process for recovering acetic acid from an aqueous stream comprising the same |
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| CN102107924A (en) * | 2009-12-29 | 2011-06-29 | 石家庄国华环保科技有限公司 | Method for comprehensively recovering and treating furfural industrial wastewater |
| CN102690248A (en) * | 2012-05-31 | 2012-09-26 | 天津大学 | Method utilizing continuous countercurrent reaction extraction of pentose solution to produce furfural |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102107924A (en) * | 2009-12-29 | 2011-06-29 | 石家庄国华环保科技有限公司 | Method for comprehensively recovering and treating furfural industrial wastewater |
| CN102690248A (en) * | 2012-05-31 | 2012-09-26 | 天津大学 | Method utilizing continuous countercurrent reaction extraction of pentose solution to produce furfural |
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