CN105777674B - A method of furfural, hydroxymethylfurfural, levulic acid are prepared using microchannel reaction unit - Google Patents
A method of furfural, hydroxymethylfurfural, levulic acid are prepared using microchannel reaction unit Download PDFInfo
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- CN105777674B CN105777674B CN201610231738.8A CN201610231738A CN105777674B CN 105777674 B CN105777674 B CN 105777674B CN 201610231738 A CN201610231738 A CN 201610231738A CN 105777674 B CN105777674 B CN 105777674B
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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
- C07D307/50—Preparation from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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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
Abstract
The invention discloses a kind of methods for preparing furfural, hydroxymethylfurfural, levulic acid using microchannel reaction unit, which comprises the steps of: (1) prepares soluble oligomeric sugar juice using lignocellulosic；(2) in the reaction unit of microchannel, furfural, hydroxymethylfurfural or levulic acid are converted into using the oligosaccharide in HCl catalysis soluble oligomeric sugar juice, when catalysis, the molar ratio of soluble oligosaccharide and HCl are 1:1~3, the temperature of catalysis reaction is 140~210 DEG C, catalysis reaction flow velocity is 1~6ml/min, and catalysis reaction retention time is 2~10min；(3) reaction solution is cooled down after reaction, extracts furfural, hydroxymethylfurfural, levulic acid in reaction solution.Conversion ratio using this method pentose is 90~97%, and furfural yield is up to 92%；The conversion ratio of hexose is the yield highest 85% of 83~92%, 5-HMF, and the yield of levulic acid is up to 87%.
Description
Technical field
The invention belongs to technical field of biochemical industry, and in particular to a kind of lignocellulosic combination microchannel reaction unit is high
The new technology that value utilizes
Background technique
To cope with increasingly serious energy crisis, the development and utilization of biomass resource are paid much attention in countries in the world in recent years.
Lignocellulosic is the most abundant renewable biomass resources on the earth, compared with other biomass resources such as starch, grease, wood
Matter cellulose has the unique advantage that do not strive grain with people, do not strive ground with grain.Biomass energy is prepared from lignocellulosic sources
Source and biological-based chemicals gradually establish biorefinery economic model, can alleviate dependence and reduction pair to petroleum industry
The pollution of environment.In the conversion process of lignocellulosic, the conversion technology based on sugared platform since reaction condition is mild,
Advantages of environment protection gains great popularity.But how efficiently to crack ingredient complicated in lignocellulosic and be still wooden fibre
Tie up the problem of plain biorefinery development.
Since the structure of wood fibre is more complicated, hemicellulose in cell wall and lignin by covalent bonding junction at
Network structure, cellulose are inlayed wherein.Moreover, there is cellulose itself the supramolecular structure of highly crystalline to make it have height water
Insoluble, each component in such lignocellulosic utilizes just extremely difficult.Therefore, natural lignocellulosic is located in advance
Reason, changes the structure of wood fibre, and appropriateness destroys cellulose, hemicellulose, the join domain between lignin, reduces cellulose
Crystallinity, increase the sponginess of raw material, the utilization efficiency of lignocellulosic can be improved.
Currently, the preprocess method of lignocellulosic is roughly divided into four kinds: physical method, chemical method, physical-chemical process and life
Object method.Physical method, which mainly passes through, is mechanically pulverized the means such as grinding, microwave radiation, steam blasting (CN 1952162A) to improve fibre
Plain enzyme enzymolysis efficiency is tieed up, is disadvantageous in that excessively high energy consumption, it is big to equipment investment.Chemical method using chemical reagent (acid, alkali,
Organic solvent) hydrolyzed hemicellulose or lignin (CN 101235605A), while changing lignocellulosic chemical composition
It will lead to the variation of its physical characteristic, such as crystallinity, internal surface area.Chemical method is since process is easy to operate, effect is obvious etc.
In the industrial production that advantage has been applied, but soda acid processing is stronger to the corrosivity of equipment, and energy consumption is also relatively high, therefore
Also many problems are encountered in practical application.Biological rule mainly uses white-rot fungi or lignin-degrading enzymes (CN 1884569)
Lignin in equal lignocellulose degradations raw material, to improve the enzymolysis efficiency of cellulase.But the enzymatic hydrolysis period is longer, it is high
The biological enzyme of effect needs development and application.Physical-chemical process (M.Ballesteros), which combines physical method with chemical method, to be taken
Some good effects, but be not widely used and industrial production.Currently, most preprocess methods are difficult simultaneously
It realizes the full constituent separation of lignocellulosic and efficiently digests.And traditional pretreatment thinking also tends to be confined to obtain and can convert
For the cellulose of ethyl alcohol, abundant attention is not given to the processing of hemicellulose, lignin.Therefore, in order to reduce production cost, energy
Preprocessing process should will be and then each inverting thirdly the separation of big component, purifying while realizing cellulose efficiently saccharifying
For useful products, just it is particularly important.Lignocellulosic is changed into soluble oligomeric by the inventions such as Roberto Rinaldi
It sugar and obtains lignin and achieves good progress.
Because of microchannel reaction unit short, microchannel large specific surface area, heat transfer and mass transfer with intermolecular diffusion length
Faster reaction rate may be implemented in the advantages that speed is fast.Simultaneously since whole process is flowing in its reaction process, so
Just largely reduce the humus that agglomerates into of compound, reduces products collection efficiency.Therefore microchannel reaction unit exists
In biomass chemical industry, it is extremely important.
Summary of the invention
The technical problem to be solved by the present invention is to provide and a kind of prepare furfural, methylol chaff using microchannel reaction unit
The method of aldehyde, levulic acid improves the efficiency that lignocellulosic prepares the compounds such as furfural, hydroxymethylfurfural, levulic acid.
Technical solution: a method of furfural, hydroxymethylfurfural, levulic acid being prepared using microchannel reaction unit,
It is characterized in that, includes the following steps:
(1) soluble oligomeric sugar juice is prepared using lignocellulosic；
(2) in the reaction unit of microchannel, chaff is converted into using the oligosaccharide in HCl catalysis soluble oligomeric sugar juice
Aldehyde, hydroxymethylfurfural or levulic acid, when catalysis, the molar ratio of soluble oligosaccharide and HCl are 1:1~3, are catalyzed the temperature of reaction
Degree is 140~210 DEG C, and catalysis reaction flow velocity is 1~6ml/min, and catalysis reaction retention time is 2~10min；
(3) reaction solution is cooled down after reaction, extracts furfural, hydroxymethylfurfural, levulic acid in reaction solution.
2, according to claim 1 to prepare furfural, hydroxymethylfurfural, levulic acid using microchannel reaction unit
Method, which is characterized in that in step (1), be prepared as follows soluble oligomeric sugar juice:
(1a) corn stover, corncob, straw, bagasse or sawdust are crushed to the wooden fibre that partial size is 100 mesh~1 centimetre
Tie up crude granule；
(2a) acid is mixed with organic solvent, obtains cracking mixed liquor, and investment 50g/L lignocellulosic particles crack mixed liquor
In, keeping the ratio of acid and lignocellulosic is 10~20mmol/g, stirs 1~3h；
(3a) is evaporated under reduced pressure under the conditions of 40~60 DEG C, and the organic solvent in removal cracking mixed liquor obtains impregnating wooden
Cellulose；
(4a) impregnates wooden cellulose grain and is placed in ball mill, and room-temperature ball-milling, ball milling temperature is lower than 45 DEG C, and Ball-milling Time is
2h, rotational speed of ball-mill 500rpm/min obtain soluble oligosaccharide and lignin mixture.
(5a) is soluble in water by mixture obtained in step 4a, removes insoluble matter, obtains soluble oligomeric sugar juice, no
Molten object is lignin.
In step (2a), the acid is the mixture of one or more of sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid, propionic acid,
The acid is preferably sulfuric acid.
In step (2a), the organic solvent is one or more of ether, acetone, MIBK, n-butanol, isobutanol
Mixture, the organic solvent is preferably ether.
In step (2a), the ratio of the acid and lignocellulosic is 10~20mmol/g, preferably 15mmol/g.
In step (2), the microchannel reaction unit includes: that the first raw material storage tank, the second raw material storage tank, micro-structure are mixed
Clutch, micro-structured reactor, extraction and stripping apparatus, the first raw material storage tank and the second raw material storage tank pass through constant flow pump and micro- knot respectively
Structure mixer is connected, and microstucture mixer, micro-structured reactor, extraction and stripping apparatus are sequentially communicated, the micro-structure reaction
Temperature control modules on device.
It answers the method for device reaction as follows using microchannel plate: soluble oligomeric sugar juice is placed in the first raw material storage tank
In, HCl solution is placed in the second raw material storage tank, and soluble oligomeric sugar juice and HCl solution mix in microstucture mixer, is mixed
It closes logistics to enter in micro-structured reactor to react, reaction temperature is 140~210 DEG C, and flow velocity is 1~6ml/min, retention time 2
~10min.
The utility model has the advantages that
Compared with prior art, main advantage of the invention:
Short processing time of the present invention, low energy consumption, low to the extent of corrosion of equipment, converts liquid for solid lignocellulosic
Oligosaccharide greatly improves lignocellulosic utilization efficiency.
Can efficiently hydrolyze in conjunction with microchannel reaction unit again can be by controllable item while oligosaccharide obtains monosaccharide
Part is directly dehydrated monosaccharide to obtain a series of platform chemicals.The conversion ratio of such method pentose is 90~95%,
Furfural yield is up to 92%；The conversion ratio of hexose is the yield highest 85% of 83~90%, 5-HMF, the production of levulic acid
Rate is up to 87%.
Detailed description of the invention
Fig. 1 is the schematic diagram of lignocellulosic pretreatment and microchannel reaction unit.
Fig. 2 is the ESI-Mass figure of soluble oligosaccharide after pretreatment.
Fig. 3 is to pass through the liquid phase figure after cellulase processing soluble oligosaccharide.
Fig. 4 is that product is furfural, hydroxymethylfurfural, the chromatogram of levulic acid after reacting.
Fig. 5 is the chromatogram that product is furfural and levulic acid after reacting.
Fig. 6 is the mass spectrogram of furfural.
Fig. 7 is the mass spectrogram of levulic acid.
Fig. 8 is the mass spectrogram of hydroxymethylfurfural.
Specific embodiment
According to following embodiments, the present invention may be better understood.However, as it will be easily appreciated by one skilled in the art that real
It applies content described in example and is merely to illustrate the present invention, without sheet described in detail in claims should will not be limited
Invention.
Instrument and model used in the present invention:
Blender: the mechanical agitator of big dragon, model OS20-S.
Ball mill: model FritschGMBH, Idar-Oberstein.
Heretofore described microchannel reaction unit includes: the first raw material storage tank, the second raw material storage tank, micro-structure mixing
Device, micro-structured reactor, extraction and stripping apparatus, the first raw material storage tank and the second raw material storage tank pass through constant flow pump and micro-structure respectively
Mixer is connected, and microstucture mixer, micro-structured reactor, extraction and stripping apparatus are sequentially communicated, the micro-structured reactor
Upper temperature control modules.
The microstucture mixer is slit plate mixer LH25 (Hastelloy C), is purchased from Ehrfeld
Mikrotechnik BTS GmbH, model 0109-4-0004-F；
The micro-structured reactor is meander reactor HC, sandwich reactor HC, fixed bed
Meander reactor HC, preferably sandwich reactor HC are purchased from Ehrfeld Mikrotechnik BTS
GmbH, model 0211-2-0314-F or 0222-2-2004-F.
The tubulose temperature control modules are purchased from Ehrfeld Mikrotechnik BTS GmbH, model 0501-
2-1004-F。
Embodiment 1:
The concentrated sulfuric acid of 9.2mmol is dissolved in 100ml ether, 10.0g corn stover (60 mesh) is taken to be distributed to ether sulfuric acid
In solution, after 300 turns of stirring 1h, ether is fallen in vacuum distillation.The corn stover of acid dip is put into ball milling in ball mill
(500rpm/min).Notice that temperature does not exceed 45 DEG C of intermittent ball millings.Then the taking-up of milled maize straw powder is weighed
To soluble lignocellulosic.It takes 1g solubility lignocellulosic to be distributed in 10ml water, shakes 5min, filter out insoluble substance i.e.
Obtain soluble oligosaccharide and lignin.The yield of soluble oligosaccharide is 95% or more.
The yield of soluble oligosaccharide is calculated as follows:
m0: the quality before soluble lignocellulosic dissolution；
M: the quality after soluble lignocellulosic dissolution after residual residue drying；
F: ratio shared by cellulose hemicellulose in lignocellulosic.
Embodiment 2:
The acetic acid of 9.2mmol is dissolved in 100ml ether, takes 10.0g corn stover (60 mesh) to be distributed to ether acetic acid molten
In liquid, after 300 turns of stirring 1h, ether is fallen in vacuum distillation.The corn stover of acid dip is put into ball milling (500rpm/ in ball mill
min).Notice that temperature does not exceed 45 DEG C of intermittent ball millings.Then milled maize straw powder is taken out into weighing and obtains solubility
Lignocellulosic.Take 1g solubility lignocellulosic to be distributed in 10ml water, shake 5min, filter out insoluble substance obtain it is solvable
Property oligosaccharide and lignin.The yield of soluble oligosaccharide is 85% or more.
Embodiment 3~5:
Using the identical condition of same embodiment 1, the difference is that embodiment 3 replaces ether with acetone；Embodiment 4 with
MIBK replaces ether；Embodiment 5 replaces ether with n-butanol；Yield is shown in Table 1.
1 embodiment of table, 3~5 testing result
| Embodiment number | Soluble oligomeric sugar yield |
| 3 | 92% |
| 4 | 87% |
| 5 | 80% |
Embodiment 6:
By soluble sugar solution (50% 1,2- dichloroethane solution) and hydrochloric acid solution 1:1 velocity ratio 1:1 in molar ratio
(overall flow rate 2ml/min) is injected separately into after microstucture mixer is sufficiently mixed by constant flow pump enters micro-structured reactor,
15min is stopped in micro-structured reactor at 140 DEG C to be reacted.Enter extraction and separation after the hot solution of microreactor is cooling
Device.Solution AUTOMATIC ZONING after into extraction equipment, upper layer are 1, the 2- dichloroethane solution of furfural and hydroxymethylfurfural, lower layer
For aqueous solution, upper solution is detected by GC-MS, and pentose conversion ratio is 88%, and furfural yield is 84%, the conversion of hexose
Rate is that 79%, 5-HMF yield is 73%, and levulic acid yield is 2%.Lower aqueous solution is detected by liquid phase, and remaining sugar can
With cycling and reutilization.
Embodiment 7~13:
Using the identical condition of same embodiment 6, the difference is that reaction temperature is changed to 150 DEG C by embodiment 7；Embodiment 8
Temperature is changed to 160 DEG C；Temperature is changed to 170 DEG C by embodiment 9；10 velocity ratio of embodiment is changed to 1:2 (overall flow rate 3ml/min)
Retention time is 10min；It is 7.5min that 11 velocity ratio of embodiment, which is changed to 1:3 (overall flow rate 4ml/min) retention time,；Embodiment
12 replace 1,2- dichloroethane solution with n-butanol；Embodiment 13 replaces 1,2- dichloroethane solution with ethyl acetate.As a result see
Table 2.
2 embodiment of table, 7~13 testing result
Embodiment 14:
By soluble sugar solution (50% 1,2- dichloroethane solution) and hydrochloric acid solution 1:1 velocity ratio 1:1 in molar ratio
(overall flow rate 2ml/min) is injected separately into after microstucture mixer is sufficiently mixed by constant flow pump enters micro-structured reactor, micro-
15min is stopped in structural response device at 190 DEG C to be reacted.Enter extraction and separation after the hot solution of microreactor is cooling to fill
It sets.Solution AUTOMATIC ZONING after into extraction equipment, upper layer are 1, the 2- dichloroethane solution of furfural and levulic acid, and lower layer is water
Solution, upper solution are detected by GC-MS, and pentose conversion ratio is 95%, and furfural yield is 93%, and the conversion ratio of hexose is
92%, 5-HMF yield are 4%, and levulic acid yield is 87%.Lower aqueous solution is detected by liquid phase, and remaining sugar can follow
Ring recycles.
Embodiment 15~21:
Using the identical condition of same embodiment 14, the difference is that reaction temperature is changed to 180 DEG C by embodiment 15；Implement
Temperature is changed to 200 DEG C by example 16；Temperature is changed to 210 DEG C by embodiment 17；18 velocity ratio of embodiment is changed to 1:2, and (overall flow rate is
3ml/min) retention time is 10min；19 velocity ratio of embodiment is changed to 1:3 (overall flow rate 4ml/min) retention time
7.5min；Embodiment 20 replaces 1,2- dichloroethane solution with n-butanol；Embodiment 21 replaces bis- chloroethene of 1,2- with ethyl acetate
Alkane solution.It the results are shown in Table 3.
Table 3
Claims (3)
1. a kind of method for preparing furfural, hydroxymethylfurfural, levulic acid using microchannel reaction unit, which is characterized in that packet
Include following steps:
(1) soluble oligomeric sugar juice is prepared using lignocellulosic；
(2) in the reaction unit of microchannel, furfural, hydroxyl are converted into using the oligosaccharide in HCl catalysis soluble oligomeric sugar juice
Methyl furfural or levulic acid, when catalysis, the molar ratio of soluble oligosaccharide and HCl are 1:1~3, and the temperature for being catalyzed reaction is
140~210 DEG C, catalysis reaction flow velocity is 1~6ml/min, and catalysis reaction retention time is 2~10min；
(3) reaction solution is cooled down after reaction, extracts furfural, hydroxymethylfurfural, levulic acid in reaction solution；
In step (1), it is prepared as follows soluble oligomeric sugar juice:
(1a) corn stover, corncob, straw, bagasse or sawdust are crushed to the wood fibre that partial size is 100 mesh~1 centimetre
Crude granule；
(2a) acid is mixed with organic solvent, obtains cracking mixed liquor, investment 50g/L lignocellulosic particles are in cracking mixed liquor
In, keeping the ratio of acid and lignocellulosic is 10~20mmol/g, stirs 1~3h；
(3a) is evaporated under reduced pressure under the conditions of 40~60 DEG C, and the organic solvent in removal cracking mixed liquor obtains dipping wood fibre
Element；
(4a) impregnates wooden cellulose grain and is placed in ball mill, and room-temperature ball-milling, ball milling temperature is lower than 45 DEG C, Ball-milling Time 2h,
Rotational speed of ball-mill is 500rpm/min, obtains soluble oligosaccharide and lignin mixture；
(5a) is soluble in water by mixture obtained in step 4a, removes insoluble matter, obtains soluble oligomeric sugar juice, insoluble
Object is lignin；
In step (2), the microchannel reaction unit includes: the first raw material storage tank, the second raw material storage tank, micro-structure mixing
Device, micro-structured reactor, extraction and stripping apparatus, the first raw material storage tank and the second raw material storage tank pass through constant flow pump and micro- knot respectively
Structure mixer is connected, and microstucture mixer, micro-structured reactor, extraction and stripping apparatus are sequentially communicated, the micro-structure reaction
Device is equipped with temperature control modules；
Soluble oligomeric sugar juice is placed in the first raw material storage tank, HCl solution is placed in the second raw material storage tank, soluble oligomeric
Sugar juice and HCl solution mix in microstucture mixer, and mixture flow, which enters in micro-structured reactor, reacts, and reaction temperature is
140~210 DEG C, flow velocity is 1~6ml/min, and retention time is 2~10min.
2. the side according to claim 1 for preparing furfural, hydroxymethylfurfural, levulic acid using microchannel reaction unit
Method, which is characterized in that in step (2a), the acid is one or more of sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid, propionic acid
Mixture.
3. the side according to claim 2 for preparing furfural, hydroxymethylfurfural, levulic acid using microchannel reaction unit
Method, which is characterized in that in step (2a), the organic solvent is ether, acetone, MIBK, n-butanol, one in isobutanol
Kind or several mixtures.
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| CN106977473B (en) * | 2017-04-14 | 2019-06-21 | 四川金象赛瑞化工股份有限公司 | A method of hemicellulose being prepared into furfural using continuous flow micro passage reaction |
| CN107163007B (en) * | 2017-06-02 | 2019-08-16 | 四川金象赛瑞化工股份有限公司 | A kind of method that continuous flow micro passage reaction hemicellulose two-step method prepares furfural |
| CN107267688B (en) * | 2017-07-03 | 2018-06-29 | 南京工业大学 | A kind of method that xylo-oligosaccharide or xylose are prepared using mill grinding |
| CN113956219A (en) * | 2021-11-01 | 2022-01-21 | 上海昶法新材料有限公司 | Process flow for producing furfural from papermaking wastewater |
| CN114315767B (en) * | 2021-11-29 | 2023-07-28 | 青岛三力本诺新材料股份有限公司 | Preparation method and preparation device of 5-hydroxymethylfurfural |
| CN115536619B (en) * | 2022-09-30 | 2023-11-03 | 中建安装集团有限公司 | Method for continuously synthesizing 5-hydroxymethylfurfural by utilizing microchannel reactor |
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