CN104387346A - Method for extracting furfural by means of multi-stage continuous countercurrent reaction of pentose - Google Patents
Method for extracting furfural by means of multi-stage continuous countercurrent reaction of pentose Download PDFInfo
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- CN104387346A CN104387346A CN201410711511.4A CN201410711511A CN104387346A CN 104387346 A CN104387346 A CN 104387346A CN 201410711511 A CN201410711511 A CN 201410711511A CN 104387346 A CN104387346 A CN 104387346A
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- C—CHEMISTRY; METALLURGY
- 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
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
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Abstract
The invention discloses a method for extracting furfural by means of a multi-stage continuous countercurrent reaction of pentose. Devices including a multi-stage reaction extractor and a rectifying device are adopted in the method; each stage of device of the multi-stage reaction extractor comprises a preheater, a reaction extraction kettle, a condenser and a phase splitter; the rectifying device comprises a rectification tower, a tower bottom heater and a tower top cooler. The method comprises the following steps: preheating an extracting agent and a pentose solution containing formic acid and ferric salt and feeding into the multi-stage reaction extractor in a countercurrent manner; performing a reaction process and an extraction process simultaneously in the reaction extractor; separating an extract phase obtained after the reaction and extraction are finished by using the rectifying device to obtain crude furfural and a regenerated extracting agent. The method disclosed by the invention has the advantages that by utilizing a multi-stage reaction and extraction process, the generated furfural can be added into the extracting agent in time, so that the possibility of side reaction of furfural is reduced, the extraction efficiency is improved, and the yield of the furfural obtained by using the method is above 75%.
Description
Technical field
The present invention relates to a kind of method being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction, belong to the production technical field of furfural.
Background technology
Furfural, has another name called furtural, is the important heterocyclic organic compound of a class.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 lignocellulose, mainly corn cob, bagasse etc.
Furfural generates and will generate pentose and dehydration of pentoses cyclisation generation furfural through hydrolysis of hemicellulose.Whether carry out in same reactor according to hydrolysis and cyclodehydration two reaction, furfural production technology is divided into one-step method production process and two-step approach production technique.Tradition furfural production adopts one-step method production process, and technique uses 4%-8% dilute sulphuric acid to make catalyzer, is shifted out by furfural by passing into steam continuously from reaction system.One-step technology less investment, technique is simple, but furaldehyde yield is low, energy consumption is high, Mierocrystalline cellulose cannot be utilized effectively, particularly seriously polluted, and therefore furfural production is subject to government and strictly controls at present.Two-step approach production technique, is be first certain density pentose solution by hydrolysis of hemicellulose in low temperature environment, then pentose solution is introduced further cyclodehydration in pyroreaction environment and generate furfural.By two-step reaction separately after, under gentle hydrolysis of hemicellulose condition, hydrolysis of hemicellulose completely and Mierocrystalline cellulose and lignin component intact, separated by solid matter by solid-liquid separation, pentose solution is used for second step reaction.The straw separated makes the easier enzymolysis of cellulose components owing to eliminating hemicellulose components, this has exactly agreed with the requirement of straw preprocessing process in cellulosic ethanol technology.Therefore two-step approach furfural production technology can make straw be fully used, and is the trend of future development.
Hydrolysis of hemicellulose process study in two-step approach production technique is ripe, and hemicellulose transformation efficiency is more than 95%, and pentose yield can reach 90%.And the research of dehydration of pentoses cyclization process is less, and only have about 50% due to the generation furaldehyde yield of side reaction.In existing research, the direct new technology being produced furfural by pentose that furfural technology is the most commercial viability of generally acknowledging at present is produced in solvent reaction extraction.It refers to and generates in the process of furfural in pentose generation dehydration reaction, add a kind of extraction agent not dissolving each other with water, furfural is had to highly selective, constantly the furfural that reaction generates is extracted into organic phase from water react system by extraction agent, to reduce side reaction thus to improve furaldehyde yield, extraction phase after having reacted obtains the extraction agent of pure furfural and regeneration by distillation technology, and extraction agent can recycle.This technology has that furaldehyde yield is high, energy consumption is low, can stop the advantages such as a large amount of furfural waste-water generations from source.
Within 1986, Sproull conducts in-depth research producing furfural technological process by wood sugar through reaction, extraction.Select sulfuric acid to be catalyzer in research, Ortho Nitro Toluene is extraction agent, in single-stage two-phase complete mixing flow reactor, carry out reaction, extraction process, reacts the furaldehyde yield that can to obtain 60% under temperature 170 DEG C, reaction times 70 min condition.Chinese patent CN102690248A discloses a kind of pentose produces furfural method through reaction, extraction, and the method uses acetic acid to be catalyzer, take Ortho Nitro Toluene as extraction agent, in Scheibel tower, carries out reaction, extraction process.Single-stage CSTR reactor efficiency is low, and extraction agent consumption is large; Scheibel tower improves extraction efficiency to a certain extent, but still maintains temperature of reaction due to phase-splitting section in tower, and this makes the furfural generated in aqueous phase that serious side reaction occur.The present invention includes reaction of high order extractor, pentose solution and extraction agent pass in reaction of high order extractor in a counter-current configuration continuously, every order reaction extractor all responds mixing process at temperature and cooled sepn process, by reaction of high order extraction process, while improve furaldehyde yield, decrease the consumption of extraction agent.
Summary of the invention
The object of the present invention is to provide a kind of method being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction.It is high that the method has furaldehyde yield, and used catalyst is little and recoverable to equipment corrosion, the feature that technological process is clean.
The present invention is realized by the following technical programs, a kind of method being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction, the device that the method adopts comprises reaction of high order extractor and rectifier unit, every further device of described reaction of high order extractor comprises preheater, reaction, extraction still, condenser and phase splitter, rectifier unit comprises well heater and overhead condenser at the bottom of rectifying tower, tower, it is characterized in that comprising the following steps:
(1) will be 0.5%-10% containing formic acid mass concentration, chloride containing iron, the concentration of ferric sulfate or iron nitrate is 0.01-1.0 mol/L and is heated to 130-220 DEG C containing the preheater of pentose solution in first step reaction, extraction device that pentose sugar concentration is 30-200 g/L, by extraction agent 2-isobutyl-phenol, 2, 4-toluene dichloride, peruscabin or the preheater of hemimellitol in last first order reaction extractor are heated to 130-220 DEG C, press pentose solution and extraction agent volume ratio 1:(1-5 afterwards), respectively and simultaneously pentose solution and extraction agent add in the reaction, extraction still in first step reaction, extraction device in reaction, extraction still and last first order reaction extractor by continuous countercurrent, be 130-220 DEG C with temperature in the reaction, extraction still of every one-level, pressure is 1-4 MPa and stirring velocity is that 100-1000 r/min carries out reaction, extraction, it is settlement separate that the outflow of every first order reaction extraction kettle enters this grade of phase splitter after this grade of condenser is cooled to 50-100 DEG C, the extracting phase of end one-level phase splitter is arranged outward, the extracting phase of all the other phase splitters at different levels is all considered as pentose solution and enters in the reaction, extraction still of next stage after the preheater of adjacent next stage is heated to 130-220 DEG C, the extraction phase of first step phase splitter enters rectifying tower and is separated, and the extraction phase of all the other phase splitters at different levels is all considered as extraction agent and enters in the reaction, extraction still of upper level after adjacent upper level preheater is heated to 130-220 DEG C,
(2) after adding rectifying tower continuously by the extraction phase of first step phase splitter output, this rectifying tower take pressure as 0.01-0.1 MPa, reflux ratio operates for 1-5, after cooling, enter chaff aldehyde storage tank by rectifying tower overhead extraction chaff aldehyde, at the bottom of rectifying tower, extraction extraction agent recycles after entering extraction agent storage tank.
The progression of above-mentioned reaction of high order extractor is 2-4 level.
Advantage of the present invention is, by reaction of high order extraction process, to effectively raise chemical reaction completeness and extraction efficiency, and in raw material, pentose transformation efficiency is more than 98%, and furaldehyde yield is more than 75%.In addition extraction agent is nontoxic and can regenerate, thus avoids the pollution to environment.Compare traditional inorganic acid catalyst as sulfuric acid, hydrochloric acid, lower concentration formic acid used is little to equipment corrosion, and side reaction is few and recyclablely reuse.Technique employs a small amount of molysite and does promotor, and that improves that pentose is degraded to furfural optionally reduces temperature of reaction simultaneously, reduces the reaction times, has saved production cost.
Accompanying drawing explanation
Accompanying drawing 1 prepares furfural schematic flow sheet for three grades of continuous countercurrents of the present invention by pentose reaction, extraction.
In figure: 1-1,2-1,3-1 are pentose solution preheater in every first order reaction extractor; 1-2,2-2,3-2 are reaction, extraction still in every first order reaction extractor; 1-3,2-3,3-3 are reaction, extraction still product water cooler in every first order reaction extractor; 1-4,2-4,3-4 are phase splitter in every first order reaction extractor; 1-5,2-5,3-5 are extraction agent preheater in every first order reaction extractor; 4 is rectifying tower.
Embodiment
Embodiment 1
In reaction of high order extractor used, every order reaction kettle amasss is 2 L, adopts turbine agitator to stir in still; Every grade of phase splitter adopts pot type structure, and single phase splitter volume is 1 L; Every grade of preheater and water cooler adopt coil arrangement, and the heat interchanging area of single preheater and water cooler is for being 0.1 m
2; Pipeline adopts Stainless steel 316 L material, and bore is 4 mm, wall thickness 2 mm; Rectifying tower is saved by four towers and forms, and long 300 mm of each tower joint, internal diameter is 22 mm, and packing layer total height is 1200 mm.
By pentose mass concentration 100 g/L, formic acid mass concentration 2%, ferric chloride concn 0.05 mol/L prepares pentose solution, and extraction agent is 2-isobutyl-phenol.Be passed in third order reaction extractor by pentose solution and extraction agent, wherein the volumetric flow rate of pentose solution is 50 mL/min simultaneously, passes into first step reactor after making it be preheated to 190 DEG C in first step preheater; The volumetric flow rate of extraction agent is 100 mL/min, passes into third stage reactor after making it be preheated to 190 DEG C in third stage preheater.In every order reaction extractor, temperature of reaction kettle is 190 DEG C, and pressure is 2.0 MPa, and stir speed (S.S.) is 600 r/min.The mixture flowed out in still enters phase splitter after being cooled to 80 DEG C, and the aqueous phase obtained after phase-splitting and organic phase enter next stage respectively and upper level continues reaction, extraction process.The extraction phase of extraction from third order reaction system enters vacuum rectification tower after cooling, and rectifying tower absolute pressure is 0.03 MPa, and reflux ratio is 3.The chaff aldehyde of rectifying tower top extraction is after overhead condenser cooling, and enter chaff aldehyde storage tank and treat follow-up refining, the extraction agent of rectifier bottoms extraction enters extraction agent storage tank Posterior circle and uses; Extracting phase storage tank is entered into after the extracting phase cooling of extraction.Be 98.6% by pentose transformation efficiency after this third order reaction extracting system, furaldehyde yield is 78.1%.
Embodiment 2
Equipment therefor is with embodiment 1.By pentose mass concentration 100 g/L, formic acid concn 2%, ferric chloride concn 0.05 mol/L prepares pentose solution, and extraction agent is 2-isobutyl-phenol.Be passed in third order reaction extractor by pentose solution and extraction agent, wherein the volumetric flow rate of pentose solution is 50 mL/min, and it passes into first step reactor be preheated to 200 DEG C in first step preheater after simultaneously; The volumetric flow rate of extraction agent is 150 mL/min, and it passes into third stage reactor be preheated to 200 DEG C in third stage preheater after.In every order reaction extractor, temperature of reaction kettle is 200 DEG C, and pressure is 2.0 MPa, and stir speed (S.S.) is 600 r/min.The mixture flowed out in still enters phase splitter after being cooled to 80 DEG C, and the aqueous phase obtained after phase-splitting and organic phase enter next stage respectively and upper level continues reaction, extraction process.The extraction phase of extraction from third order reaction system enters vacuum rectification tower after cooling, and rectifying tower absolute pressure is 0.03 MPa, and reflux ratio is 3.The chaff aldehyde of rectifying tower top extraction is after overhead condenser cooling, and enter chaff aldehyde storage tank and treat follow-up refining, the extraction agent of rectifier bottoms extraction enters extraction agent storage tank Posterior circle and uses; Enter into extracting phase storage tank after the extracting phase cooling of extraction, enter in stock liquid storage tank after supplementing pentose and recycle.Be 99.1% by pentose transformation efficiency after this third order reaction extracting system, furaldehyde yield is 80.1%.
Embodiment 3
Equipment therefor is with embodiment 1.By pentose mass concentration 150 g/L, formic acid concn 3%, ferric chloride concn 0.08 mol/L prepares pentose solution, and extraction agent is 2,4-DCT.Be passed in third order reaction extractor by pentose solution and extraction agent, wherein the volumetric flow rate of pentose solution is 50 mL/min, and it passes into first step reactor be preheated to 200 DEG C in first step preheater after simultaneously; The volumetric flow rate of extraction agent is 150 mL/min, and it passes into third stage reactor be preheated to 200 DEG C in third stage preheater after.In every order reaction extractor, temperature of reaction kettle is 200 DEG C, and pressure is 2.0 MPa, and stir speed (S.S.) is 600 r/min.The mixture flowed out in still enters phase splitter after being cooled to 80 DEG C, and the aqueous phase obtained after phase-splitting and organic phase enter next stage respectively and upper level continues reaction, extraction process.The extraction phase of extraction from fourth-order reaction system enters vacuum rectification tower after cooling, and rectifying tower absolute pressure is 0.04 MPa, and reflux ratio is 2.The chaff aldehyde of rectifying tower top extraction is after overhead condenser cooling, and enter chaff aldehyde storage tank and treat follow-up refining, the extraction agent of rectifier bottoms extraction enters extraction agent storage tank Posterior circle and uses; Enter into extracting phase storage tank after the extracting phase cooling of extraction, enter in stock liquid storage tank after supplementing pentose and recycle.Be 98.1% by pentose transformation efficiency after this fourth-order reaction extracting system, furaldehyde yield is 75.3%.
Embodiment 4
Equipment therefor is with embodiment 1.By pentose mass concentration 150 g/L, formic acid concn 3%, ferric sulfate concentration 0.08 mol/L prepares pentose solution, and extraction agent is peruscabin.Be passed in fourth-order reaction extractor by pentose solution and extraction agent, wherein the volumetric flow rate of pentose solution is 50 mL/min, and it passes into first step reactor be preheated to 200 DEG C in first step preheater after simultaneously; The volumetric flow rate of extraction agent is 150 mL/min, and it passes into fourth stage reactor be preheated to 200 DEG C in fourth stage preheater after.In every order reaction extractor, temperature of reaction kettle is 200 DEG C, and pressure is 2.0 MPa, and stir speed (S.S.) is 600 r/min.The mixture flowed out in still enters phase splitter after being cooled to 80 DEG C, and the aqueous phase obtained after phase-splitting and organic phase enter next stage respectively and upper level continues reaction, extraction process.The extraction phase of extraction from fourth-order reaction system enters vacuum rectification tower after cooling, and rectifying tower absolute pressure is 0.04 MPa, and reflux ratio is 2.The chaff aldehyde of rectifying tower top extraction is after overhead condenser cooling, and enter chaff aldehyde storage tank and treat follow-up refining, the extraction agent of rectifier bottoms extraction enters extraction agent storage tank Posterior circle and uses; Enter into extracting phase storage tank after the extracting phase cooling of extraction, enter in stock liquid storage tank after supplementing pentose and recycle.Be 97.1% by pentose transformation efficiency after this fourth-order reaction extracting system, furaldehyde yield is 75.1%.
Embodiment 5
Equipment therefor is with embodiment 1.By pentose mass concentration 50 g/L, formic acid concn 2%, ferric sulfate concentration 0.04 mol/L prepares pentose solution, and extraction agent is hemimellitol.Be passed in second order reaction extractor by pentose solution and extraction agent, wherein the volumetric flow rate of pentose solution is 50 mL/min, and it passes into first step reactor be preheated to 180 DEG C in first step preheater after simultaneously; The volumetric flow rate of extraction agent is 75 mL/min, and it passes into second stage reactor be preheated to 180 DEG C in the preheater of the second stage after.In every order reaction extractor, temperature of reaction kettle is 180 DEG C, pressure is 2.0 MPa, stir is passed in third order reaction extracting system by pentose solution and extraction agent simultaneously, wherein the volumetric flow rate of pentose solution is 50 mL/min, and it passes into first step reactor be preheated to 200 DEG C in first step preheater after; The volumetric flow rate of extraction agent is 150 mL/min, and it passes into third stage reactor be preheated to 200 DEG C in third stage preheater after.Rate is 600 r/min.The mixture flowed out in still enters phase splitter after being cooled to 80 DEG C, and the aqueous phase obtained after phase-splitting and organic phase enter next stage respectively and upper level continues reaction, extraction process.The extraction phase of extraction from second order reaction system enters vacuum rectification tower after cooling, and rectifying tower absolute pressure is 0.03 MPa, and reflux ratio is 4.The chaff aldehyde of rectifying tower top extraction is after overhead condenser cooling, and enter chaff aldehyde storage tank and treat follow-up refining, the extraction agent of rectifier bottoms extraction enters extraction agent storage tank Posterior circle and uses; Enter into extracting phase storage tank after the extracting phase cooling of extraction, enter in stock liquid storage tank after supplementing pentose and recycle.Be 99.2% by pentose transformation efficiency after this second order reaction extracting system, furaldehyde yield is 83.5%.
Claims (2)
1. prepared the method for furfural by pentose multiple stage continuous adverse current reaction, extraction for one kind, the device that the method adopts comprises reaction of high order extractor and rectifier unit, every further device of reaction of high order extractor comprises preheater, reaction, extraction still, condenser and phase splitter, rectifier unit comprises well heater and overhead condenser at the bottom of rectifying tower, tower, it is characterized in that comprising the following steps:
(1) will be 0.5%-10% containing formic acid mass concentration, chloride containing iron, the concentration of ferric sulfate or iron nitrate is 0.01-1.0 mol/L and is heated to 130-220 DEG C containing the preheater of pentose solution in first step reaction, extraction device that pentose sugar concentration is 30-200 g/L, by extraction agent 2-isobutyl-phenol, 2, 4-toluene dichloride, peruscabin or the preheater of hemimellitol in last first order reaction extractor are heated to 130-220 DEG C, press pentose solution and extraction agent volume ratio 1:(1-5 afterwards), respectively and simultaneously pentose solution and extraction agent add in the reaction, extraction still in first step reaction, extraction device in reaction, extraction still and last first order reaction extractor by continuous countercurrent, be 130-220 DEG C with temperature in the reaction, extraction still of every one-level, pressure is 1-4 MPa and stirring velocity is that 100-1000 r/min carries out reaction, extraction, it is settlement separate that the outflow of every first order reaction extraction kettle enters this grade of phase splitter after this grade of condenser is cooled to 50-100 DEG C, the extracting phase of end one-level phase splitter is arranged outward, the extracting phase of all the other phase splitters at different levels is all considered as pentose solution and enters in the reaction, extraction still of next stage after the preheater of adjacent next stage is heated to 130-220 DEG C, the extraction phase of first step phase splitter enters rectifying tower and is separated, and the extraction phase of all the other phase splitters at different levels is all considered as extraction agent and enters in the reaction, extraction still of upper level after adjacent upper level preheater is heated to 130-220 DEG C,
(2) after adding rectifying tower continuously by the extraction phase of first step phase splitter output, this rectifying tower take pressure as 0.01-0.1 MPa, reflux ratio operates for 1-5, after cooling, enter chaff aldehyde storage tank by rectifying tower overhead extraction chaff aldehyde, at the bottom of rectifying tower, extraction extraction agent recycles after entering extraction agent storage tank.
2., by the method being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction according to claim 1, it is characterized in that the progression of reaction of high order extractor is 2-4 level.
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| CN108721942A (en) * | 2018-06-04 | 2018-11-02 | 甘肃泓旭化工科技有限责任公司 | A kind of continuous flow upstream extraction of liquid phase mixture washes reaction process and application |
| CN109180617A (en) * | 2018-09-17 | 2019-01-11 | 中国科学院广州能源研究所 | A kind of two-phase biomass pretreatment coproduction chemical processes based on Furnan products extractant |
| CN110003149A (en) * | 2019-03-20 | 2019-07-12 | 肖兵 | With the method for glacial acetic acid catalysis xylose extraction production furfural under a kind of normal pressure |
| US20190256484A1 (en) * | 2016-11-01 | 2019-08-22 | Shell Oil Company | Process for the recovery of furfural |
| CN110437186A (en) * | 2019-08-01 | 2019-11-12 | 四川金象赛瑞化工股份有限公司 | A kind of technique preparing furfural using xylose mother liquid |
| CN110563675A (en) * | 2019-08-01 | 2019-12-13 | 四川金象赛瑞化工股份有限公司 | Method for preparing furfural by extracting xylose through steam explosion of cotton stalks and full utilization |
| CN112876435A (en) * | 2021-03-02 | 2021-06-01 | 安徽金轩科技有限公司 | Refining method of furfural |
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| US20190256484A1 (en) * | 2016-11-01 | 2019-08-22 | Shell Oil Company | Process for the recovery of furfural |
| US10899725B2 (en) * | 2016-11-01 | 2021-01-26 | Shell Oil Company | Process for the recovery of furfural |
| CN108721942A (en) * | 2018-06-04 | 2018-11-02 | 甘肃泓旭化工科技有限责任公司 | A kind of continuous flow upstream extraction of liquid phase mixture washes reaction process and application |
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| CN109180617A (en) * | 2018-09-17 | 2019-01-11 | 中国科学院广州能源研究所 | A kind of two-phase biomass pretreatment coproduction chemical processes based on Furnan products extractant |
| CN109180617B (en) * | 2018-09-17 | 2020-12-04 | 中国科学院广州能源研究所 | Two-phase biomass pretreatment co-production chemical method based on furfural compound extractant |
| CN110003149A (en) * | 2019-03-20 | 2019-07-12 | 肖兵 | With the method for glacial acetic acid catalysis xylose extraction production furfural under a kind of normal pressure |
| CN110437186A (en) * | 2019-08-01 | 2019-11-12 | 四川金象赛瑞化工股份有限公司 | A kind of technique preparing furfural using xylose mother liquid |
| CN110563675A (en) * | 2019-08-01 | 2019-12-13 | 四川金象赛瑞化工股份有限公司 | Method for preparing furfural by extracting xylose through steam explosion of cotton stalks and full utilization |
| CN110437186B (en) * | 2019-08-01 | 2021-05-11 | 四川金象赛瑞化工股份有限公司 | Process for preparing furfural by using xylose mother liquor |
| CN110563675B (en) * | 2019-08-01 | 2023-05-30 | 四川金象赛瑞化工股份有限公司 | Method for preparing furfural and fully utilizing xylose by cotton stalk steam explosion extraction |
| CN112876435A (en) * | 2021-03-02 | 2021-06-01 | 安徽金轩科技有限公司 | Refining method of furfural |
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