CN104387346B - Prepared the method for furfural by pentose multiple stage continuous adverse current reaction, extraction - Google Patents
Prepared the method for furfural by pentose multiple stage continuous adverse current reaction, extraction Download PDFInfo
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- CN104387346B CN104387346B CN201410711511.4A CN201410711511A CN104387346B CN 104387346 B CN104387346 B CN 104387346B CN 201410711511 A CN201410711511 A CN 201410711511A CN 104387346 B CN104387346 B CN 104387346B
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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 kind of method of being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction, the device that the method adopts is reaction of high order extractor and rectifier unit, each stage arrangement of reaction of high order extractor comprises preheater, reaction, extraction still, condenser and phase-splitter, and rectifier unit comprises heater and overhead condenser at the bottom of rectifying column, tower. Its process: will be passed into reaction of high order extractor in the mode of adverse current after the pentose solution that contain formic acid and molysite and extractant preheating, carry out course of reaction and extraction process simultaneously in reaction, extraction device. The extraction phase obtaining after reaction, extraction completes separates the extractant that obtains chaff aldehyde and regeneration by rectifier unit. The invention has the advantages that and utilize reaction of high order extraction process, can make the furfural generating enter in time in extractant, reduced the chance of furfural generation side reaction, improved extraction efficiency, the furaldehyde yield obtaining through this method can reach more than 75%.
Description
Technical field
The present invention relates to a kind of method of 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. The chemical products that directly or indirectly derive taking furfural as raw material reach kind more than 1600, are widely used in the industries such as medicine, agricultural chemicals, resin, daily use chemicals, casting, weaving, oil. Up to now, furfural can only make taking lignocellulosic as raw material, is mainly corncob, bagasse etc.
Furfural generates and will generate pentose and pentose cyclodehydration generation furfural through hydrolysis of hemicellulose. Whether in same reactor, carry out according to hydrolysis and two reactions of cyclodehydration, furfural production technology is divided into one-step method production process and two-step method production technology. Tradition furfural production adopts one-step method production process, and technique is used 4%-8% dilute sulfuric acid to make catalyst, by passing into continuously steam, furfural is shifted out from reaction system. One-step technology small investment, technique is simple, but furaldehyde yield is low, energy consumption is high, cellulose cannot be utilized effectively, and particularly seriously polluted, therefore at present furfural production is subject to government and strictly controls. Two-step method production technology, is to be first certain density pentose solution by hydrolysis of hemicellulose in low temperature environment, then pentose solution is introduced to further cyclodehydration in pyroreaction environment and is generated furfural. By two-step reaction separately after, under gentle hydrolysis of hemicellulose condition, hydrolysis of hemicellulose completely and cellulose and lignin composition intact, by Separation of Solid and Liquid, solid matter is separated, pentose solution is for second step reaction. The straw of separating makes the easier enzymolysis of cellulose components owing to having removed hemicellulose components, and this has exactly agreed with the requirement of straw preprocessing process in cellulosic ethanol technology. Therefore two-step method furfural production technology can make straw be fully used, and is the trend of future development.
Hydrolysis of hemicellulose process study maturation in two-step method production technology, hemicellulose conversion ratio is more than 95%, and pentose yield can reach 90%. And the process study of pentose cyclodehydration is less, and because the generation furaldehyde yield of side reaction only has 50% left and right. In existing research, the new technology of directly being produced furfural by pentose that furfural technology is the tool commercial viability of generally acknowledging is at present produced in solvent reaction extraction. It refers in pentose generation dehydration and generates in the process of furfural, add a kind of and water not dissolve each other, furfural is had the extractant of high selectivity, the furfural constantly reaction being generated by extractant is extracted into organic phase from aqueous phase reactions system, thereby improve furaldehyde yield to reduce side reaction, extraction phase after having reacted obtains the extractant of pure furfural and regeneration by distillation technology, extractant can recycle. This technology has that furaldehyde yield is high, energy consumption is low, can stop from source the advantages such as a large amount of furfural waste-water generations.
Within 1986, Sproull conducts in-depth research producing furfural technical process by wood sugar through reaction, extraction. In research, selecting sulfuric acid is catalyst, and ortho-methylnitrobenzene is extractant, in single-stage two-phase complete mixing flow reactor, carries out reaction, extraction process, and reaction can obtain 60% furaldehyde yield under 170 DEG C of temperature, reaction time 70min condition. Chinese patent CN102690248A discloses the method for a kind of pentose through reaction, extraction production furfural, and it is catalyst that the method is used acetic acid, taking ortho-methylnitrobenzene as extractant, carries out reaction, extraction process in Scheibel tower. Single-stage CSTR reactor efficiency is low, and extractant consumption is large; Scheibel tower has improved extraction efficiency to a certain extent, but because phase-splitting section in tower still maintains reaction temperature, this makes the furfural generating in water that serious side reaction occur. The present invention includes reaction of high order extractor, pentose solution and extractant pass in reaction of high order extractor continuously with reflux type, every order reaction extractor all respond mixed process and cooled separation process at temperature, by reaction of high order extraction process, in having improved furaldehyde yield, reduce the consumption of extractant.
Summary of the invention
The object of the present invention is to provide a kind of method of 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 technical process is clean.
The present invention is realized by the following technical programs, a kind of method of 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, each stage arrangement of described reaction of high order extractor comprises preheater, reaction, extraction still, condenser and phase-splitter, rectifier unit comprises heater and overhead condenser at the bottom of rectifying column, tower, it is characterized in that comprising the following steps:
(1) will contain formic acid mass concentration is 0.5%-10%, chloride containing iron, the concentration of ferric sulfate or ferric nitrate is 0.01-1.0mol/L and is 30-200g/L containing pentose concentration the preheater of pentose solution in first order reaction, extraction device is heated to 130-220 DEG C, by extractant 2-isobutyl group phenol, 2, 4-dichlorotoleune, Ergol or the hemimellitol preheater in last first order reaction extractor is heated to 130-220 DEG C, press afterwards pentose solution and extractant volume ratio 1:(1-5), respectively and simultaneously continuous flow upstream adds pentose solution and extractant in first order reaction, extraction device in the reaction, extraction still in reaction, extraction still and last first order reaction extractor, in the reaction, extraction still of every one-level taking temperature as 130-220 DEG C, pressure is that 1-4MPa and mixing speed are that 100-1000r/min carries out reaction, extraction, the outflow of every first order reaction extraction kettle enters this grade of phase-splitter sedimentation separation after this grade of condenser is cooled to 50-100 DEG C, the raffinate phase of end one-level phase-splitter is arranged outward, the raffinate phase of all the other phase-splitters at different levels is all considered as pentose solution and is heated to enter after 130-220 DEG C in the reaction, extraction still of next stage through the preheater of adjacent next stage, the extraction phase of first order phase-splitter enters rectifying column and separates, and the extraction phase of all the other phase-splitters at different levels is all considered as extractant and is heated to enter after 130-220 DEG C in the reaction, extraction still of upper level through adjacent upper level preheater,
(2) added continuously after rectifying column by the extraction phase of first order phase-splitter output, this rectifying column taking pressure as 0.01-0.1MPa, reflux ratio operates as 1-5, after cooling, enter chaff aldehyde storage tank by rectifying column tower top extraction chaff aldehyde, at the bottom of rectifying tower, extraction extractant recycles after entering extractant 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 degree of reacting completely and extraction efficiency, and in raw material, pentose conversion ratio is that more than 98% furaldehyde yield is more than 75%. In addition extractant is nontoxic and can regenerate, thereby has avoided the pollution to environment. Compare traditional inorganic acid catalyst as sulfuric acid, hydrochloric acid, low concentration formic acid used is little to equipment corrosion, few and recyclable the reusing of side reaction. Technique has been used a small amount of molysite to do co-catalyst, and that improves that pentose is degraded to furfural optionally reduces reaction temperature simultaneously, reduces the reaction time, has saved production cost.
Brief description of the drawings
Accompanying drawing 1 is prepared furfural schematic flow sheet for three grades of continuous flow upstreams of the present invention by pentose reaction, extraction.
In figure: 1-1,2-1,3-1 is pentose solution preheater in every first order reaction extractor; 1-2,2-2,3-2 is reaction, extraction still in every first order reaction extractor; 1-3,2-3,3-3 is reaction, extraction still product cooler in every first order reaction extractor; 1-4,2-4,3-4 is phase-splitter in every first order reaction extractor; 1-5,2-5,3-5 is extractant preheater in every first order reaction extractor; 4 is rectifying column.
Detailed description of the invention
Embodiment 1
In reaction of high order extractor used, every order reaction kettle amasss as 2L, adopts turbine stirrer to stir in still; Every grade of phase-splitter adopts pot type structure, and single phase-splitter volume is 1L; Every grade of preheater and cooler adopt coil arrangement, and the heat exchange area of single preheater and cooler is for being 0.1m2; Pipeline adopts Stainless steel 316 L material, and bore is 4mm, wall thickness 2mm; Rectifying column is made up of four tower joints, the long 300mm of each tower joint, and internal diameter is 22mm, packing layer total height is 1200mm.
Press pentose mass concentration 100g/L, formic acid mass concentration 2%, ferric chloride concn 0.05mol/L prepares pentose solution, and extractant is 2-isobutyl group phenol. Pentose solution and extractant are passed in third-order reaction extractor simultaneously, and wherein the volume flow of pentose solution is 50mL/min, passes into first order reactor after making it be preheated to 190 DEG C in first order preheater; The volume flow of extractant is 100mL/min, passes into third level reactor after making it be preheated to 190 DEG C in third level preheater. In every order reaction extractor, temperature of reaction kettle is 190 DEG C, and pressure is 2.0MPa, and stir speed (S.S.) is 600r/min. The mixture flowing out in still enters phase-splitter after being cooled to 80 DEG C, and the water obtaining after phase-splitting and organic phase enter respectively next stage and upper level continues reaction, extraction process. From third-order reaction system, the extraction phase of extraction enters rectification under vacuum tower after cooling, and rectifying column absolute pressure is 0.03MPa, and reflux ratio is 3. The chaff aldehyde of rectifying column top extraction, after overhead condenser is cooling, enters chaff aldehyde storage tank and treats follow-up refining, and the extractant of rectifier bottoms extraction recycles after entering extractant storage tank; After the raffinate phase of extraction is cooling, enter into raffinate phase storage tank. Be 98.6% by pentose conversion ratio after this third-order reaction extracting system, furaldehyde yield is 78.1%.
Embodiment 2
Equipment therefor is with embodiment 1. Press pentose mass concentration 100g/L, formic acid concn 2%, ferric chloride concn 0.05mol/L prepares pentose solution, and extractant is 2-isobutyl group phenol. Pentose solution and extractant are passed in third-order reaction extractor simultaneously, and wherein the volume flow of pentose solution is 50mL/min, and it passes into first order reactor be preheated to 200 DEG C in first order preheater after; The volume flow of extractant is 150mL/min, and it passes into third level reactor be preheated to 200 DEG C in third level preheater after. In every order reaction extractor, temperature of reaction kettle is 200 DEG C, and pressure is 2.0MPa, and stir speed (S.S.) is 600r/min. The mixture flowing out in still enters phase-splitter after being cooled to 80 DEG C, and the water obtaining after phase-splitting and organic phase enter respectively next stage and upper level continues reaction, extraction process. From third-order reaction system, the extraction phase of extraction enters rectification under vacuum tower after cooling, and rectifying column absolute pressure is 0.03MPa, and reflux ratio is 3. The chaff aldehyde of rectifying column top extraction, after overhead condenser is cooling, enters chaff aldehyde storage tank and treats follow-up refining, and the extractant of rectifier bottoms extraction recycles after entering extractant storage tank; After the raffinate phase of extraction is cooling, enter into raffinate phase storage tank, supplement after pentose and enter in material liquid storage tank and recycle. Be 99.1% by pentose conversion ratio after this third-order reaction extracting system, furaldehyde yield is 80.1%.
Embodiment 3
Equipment therefor is with embodiment 1. Press pentose mass concentration 150g/L, formic acid concn 3%, ferric chloride concn 0.08mol/L prepares pentose solution, and extractant is 2,4-DCT. Pentose solution and extractant are passed in third-order reaction extractor simultaneously, and wherein the volume flow of pentose solution is 50mL/min, and it passes into first order reactor be preheated to 200 DEG C in first order preheater after; The volume flow of extractant is 150mL/min, and it passes into third level reactor be preheated to 200 DEG C in third level preheater after. In every order reaction extractor, temperature of reaction kettle is 200 DEG C, and pressure is 2.0MPa, and stir speed (S.S.) is 600r/min. The mixture flowing out in still enters phase-splitter after being cooled to 80 DEG C, and the water obtaining after phase-splitting and organic phase enter respectively next stage and upper level continues reaction, extraction process. From fourth-order reaction system, the extraction phase of extraction enters rectification under vacuum tower after cooling, and rectifying column absolute pressure is 0.04MPa, and reflux ratio is 2. The chaff aldehyde of rectifying column top extraction, after overhead condenser is cooling, enters chaff aldehyde storage tank and treats follow-up refining, and the extractant of rectifier bottoms extraction recycles after entering extractant storage tank; After the raffinate phase of extraction is cooling, enter into raffinate phase storage tank, supplement after pentose and enter in material liquid storage tank and recycle. Be 98.1% by pentose conversion ratio after this fourth-order reaction extracting system, furaldehyde yield is 75.3%.
Embodiment 4
Equipment therefor is with embodiment 1. Press pentose mass concentration 150g/L, formic acid concn 3%, ferric sulfate concentration 0.08mol/L prepares pentose solution, and extractant is Ergol. Pentose solution and extractant are passed in fourth-order reaction extractor simultaneously, and wherein the volume flow of pentose solution is 50mL/min, and it passes into first order reactor be preheated to 200 DEG C in first order preheater after; The volume flow of extractant is 150mL/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 2.0MPa, and stir speed (S.S.) is 600r/min. The mixture flowing out in still enters phase-splitter after being cooled to 80 DEG C, and the water obtaining after phase-splitting and organic phase enter respectively next stage and upper level continues reaction, extraction process. From fourth-order reaction system, the extraction phase of extraction enters rectification under vacuum tower after cooling, and rectifying column absolute pressure is 0.04MPa, and reflux ratio is 2. The chaff aldehyde of rectifying column top extraction, after overhead condenser is cooling, enters chaff aldehyde storage tank and treats follow-up refining, and the extractant of rectifier bottoms extraction recycles after entering extractant storage tank; After the raffinate phase of extraction is cooling, enter into raffinate phase storage tank, supplement after pentose and enter in material liquid storage tank and recycle. Be 97.1% by pentose conversion ratio after this fourth-order reaction extracting system, furaldehyde yield is 75.1%.
Embodiment 5
Equipment therefor is with embodiment 1. Press pentose mass concentration 50g/L, formic acid concn 2%, ferric sulfate concentration 0.04mol/L prepares pentose solution, and extractant is hemimellitol. Pentose solution and extractant are passed in second order reaction extractor simultaneously, and wherein the volume flow of pentose solution is 50mL/min, and it passes into first order reactor be preheated to 180 DEG C in first order preheater after; The volume flow of extractant is 75mL/min, and it passes into second level reactor be preheated to 180 DEG C in the preheater of the second level after. In every order reaction extractor, temperature of reaction kettle is 180 DEG C, pressure is 2.0MPa, stir pentose solution and extractant are passed in third-order reaction extracting system simultaneously, wherein the volume flow of pentose solution is 50mL/min, and it passes into first order reactor be preheated to 200 DEG C in first order preheater after; The volume flow of extractant is 150mL/min, and it passes into third level reactor be preheated to 200 DEG C in third level preheater after. Rate is 600r/min. The mixture flowing out in still enters phase-splitter after being cooled to 80 DEG C, and the water obtaining after phase-splitting and organic phase enter respectively next stage and upper level continues reaction, extraction process. From second order reaction system, the extraction phase of extraction enters rectification under vacuum tower after cooling, and rectifying column absolute pressure is 0.03MPa, and reflux ratio is 4. The chaff aldehyde of rectifying column top extraction, after overhead condenser is cooling, enters chaff aldehyde storage tank and treats follow-up refining, and the extractant of rectifier bottoms extraction recycles after entering extractant storage tank; After the raffinate phase of extraction is cooling, enter into raffinate phase storage tank, supplement after pentose and enter in material liquid storage tank and recycle. Be 99.2% by pentose conversion ratio 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, each stage arrangement of reaction of high order extractor comprises preheater, reaction, extraction still, condenser and phase-splitter, rectifier unit comprises heater and overhead condenser at the bottom of rectifying column, tower, it is characterized in that comprising the following steps:
(1) will contain formic acid mass concentration is 0.5%-10%, chloride containing iron, the concentration of ferric sulfate or ferric nitrate is 0.01-1.0mol/L and is 30-200g/L containing pentose concentration the preheater of pentose solution in first order reaction, extraction device is heated to 130-220 DEG C, by extractant 2-isobutyl group phenol, 2, 4-dichlorotoleune, Ergol or the 1,2,3-trimethylbenzene preheater in last first order reaction extractor is heated to 130-220 DEG C, press afterwards pentose solution and extractant volume ratio 1:(1-5), respectively and simultaneously continuous flow upstream adds pentose solution and extractant in first order reaction, extraction device in the reaction, extraction still in reaction, extraction still and last first order reaction extractor, in the reaction, extraction still of every one-level taking temperature as 130-220 DEG C, pressure is that 1-4MPa and mixing speed are that 100-1000r/min carries out reaction, extraction, the outflow of every first order reaction extraction kettle enters this grade of phase-splitter sedimentation separation after this grade of condenser is cooled to 50-100 DEG C, the raffinate phase of end one-level phase-splitter is arranged outward, the raffinate phase of all the other phase-splitters at different levels is all considered as pentose solution and is heated to enter after 130-220 DEG C in the reaction, extraction still of next stage through the preheater of adjacent next stage, the extraction phase of first order phase-splitter enters rectifying column and separates, and the extraction phase of all the other phase-splitters at different levels is all considered as extractant and is heated to enter after 130-220 DEG C in the reaction, extraction still of upper level through adjacent upper level preheater,
(2) added continuously after rectifying column by the extraction phase of first order phase-splitter output, this rectifying column taking pressure as 0.01-0.1MPa, reflux ratio operates as 1-5, after cooling, enter chaff aldehyde storage tank by rectifying column tower top extraction chaff aldehyde, at the bottom of rectifying tower, extraction extractant recycles after entering extractant storage tank.
2. by the method for being prepared furfural by pentose multiple stage continuous adverse current reaction, extraction claimed in claim 1, the progression that it is characterized in that reaction of high order extractor is 2-4 level.
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| CA3039792A1 (en) * | 2016-11-01 | 2018-05-11 | Shell Internationale Research Maatschappij B.V. | Process for the recovery of furfural |
| CN108721942B (en) * | 2018-06-04 | 2024-01-26 | 甘肃泓旭化工科技有限责任公司 | Continuous countercurrent reaction process of liquid phase mixture and application |
| 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 |
| CN110003149B (en) * | 2019-03-20 | 2020-08-28 | 上海乔克科技有限公司 | Method for producing furfural by catalytic xylose extraction under normal pressure by glacial acetic acid |
| 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 |
| 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 |
| CN112876435B (en) * | 2021-03-02 | 2022-01-04 | 安徽金轩科技有限公司 | Refining method of furfural |
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